MiMeDB: Showing metabocard for Microcolin H (MMDBc0025336)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 15:03:35 UTC

Update Date

2025-10-07 16:07:31 UTC

Metabolite ID

MMDBc0025336

Metabolite Identification

Common Name

Microcolin H

Description

Microcolin H is a naturally occurring marine lipopeptide that belongs to the chemical class of metabolites. Its chemical structure features a unique arrangement of amino acids that facilitates its interaction with specific biological targets. Microcolin H functions primarily as an autophagy inducer, exhibiting potent antitumor activity by directly binding to phosphatidylinositol transfer proteins α and β (PITPα/β). This binding triggers a cascade of cellular events, including the conversion of LC3I to LC3II and a decrease in p62 levels, which ultimately leads to autophagic cell death in various tumor cell lines (PMID:37963877 ). Furthermore, Microcolin H has demonstrated significant antitumor efficacy in preclinical models, including nude mouse subcutaneous tumor models, while exhibiting low toxicity (PMID:37963877 ). The compound's ability to induce autophagic cell death highlights its potential as a therapeutic agent, particularly through the targeting of PITPα/β, which may serve as a promising avenue for cancer treatment (PMID:37963877 ). Overall, Microcolin H represents a valuable addition to the repertoire of compounds being investigated for their roles in cancer biology and therapeutic development (PMID:40710508 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152117032D          

 60 61  0  0  1  0            999 V2000
    9.9858    2.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9373    2.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4695    0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3136    5.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7813    6.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0395    3.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3615    7.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8082    3.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7436    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4427    3.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6523    4.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7654    1.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3890    2.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1686    2.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7922    2.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5718    2.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1596    9.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5016    9.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5341    2.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3497    8.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4375    7.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3136    1.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9373    6.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1954    2.8207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.8895    8.2837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1845    3.3608    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.1200    2.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5395    8.3102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3781    2.8207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.7483    7.7438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.8250    9.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4050    3.6309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.7168    5.7912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0018    3.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9750    2.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5670    7.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2491    4.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3404    6.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7813    3.0908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5986    3.0908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8727    4.9811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1845    7.1414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0647    8.2996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2759    1.4705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9372    8.8739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0454    9.3591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8459    4.1710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1309    1.7405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8879    6.8817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4695    4.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1200    6.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3404    2.5507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4159    3.0908    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.5009    7.5560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0286    4.1710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7638    8.0294    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1577    2.5507    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.0290    6.9680    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5609    2.8207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5609    6.6014    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 18 17  2  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22 19  1  0  0  0  0
 23  4  1  0  0  0  0
 23  5  1  0  0  0  0
 24  6  1  1  0  0  0
 24 16  1  0  0  0  0
 25  7  1  6  0  0  0
 25 17  1  0  0  0  0
 26  8  1  1  0  0  0
 27  9  1  0  0  0  0
 28 20  1  0  0  0  0
 28 21  1  0  0  0  0
 29 19  1  0  0  0  0
 30 20  1  0  0  0  0
 31 18  1  0  0  0  0
 32 26  1  0  0  0  0
 33 23  1  0  0  0  0
 34 29  1  0  0  0  0
 35 24  1  0  0  0  0
 30 36  1  1  0  0  0
 37 32  1  0  0  0  0
 38 33  1  0  0  0  0
 32 39  1  6  0  0  0
 39 34  2  0  0  0  0
 40 10  1  0  0  0  0
 29 40  1  1  0  0  0
 40 35  1  0  0  0  0
 41 11  1  0  0  0  0
 33 41  1  6  0  0  0
 41 37  1  0  0  0  0
 42 21  1  0  0  0  0
 42 30  1  0  0  0  0
 42 38  1  0  0  0  0
 43 25  1  0  0  0  0
 43 31  1  0  0  0  0
 43 36  1  0  0  0  0
 44 27  2  0  0  0  0
 28 45  1  1  0  0  0
 46 31  2  0  0  0  0
 34 47  1  4  0  0  0
 48 35  2  0  0  0  0
 49 36  2  0  0  0  0
 50 37  2  0  0  0  0
 51 38  2  0  0  0  0
 52 26  1  0  0  0  0
 52 27  1  0  0  0  0
 24 53  1  6  0  0  0
 25 54  1  1  0  0  0
 26 55  1  6  0  0  0
 28 56  1  6  0  0  0
 29 57  1  1  0  0  0
 30 58  1  6  0  0  0
 32 59  1  1  0  0  0
 33 60  1  6  0  0  0
M  END


  Mrv1652305152117032D          

 60 61  0  0  1  0            999 V2000
    9.9858    2.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9373    2.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4695    0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3136    5.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7813    6.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0395    3.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3615    7.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8082    3.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7436    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4427    3.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6523    4.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7654    1.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3890    2.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1686    2.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7922    2.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5718    2.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1596    9.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5016    9.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5341    2.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3497    8.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4375    7.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3136    1.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9373    6.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1954    2.8207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.8895    8.2837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1845    3.3608    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.1200    2.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5395    8.3102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3781    2.8207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.7483    7.7438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.8250    9.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4050    3.6309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.7168    5.7912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0018    3.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9750    2.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5670    7.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2491    4.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3404    6.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7813    3.0908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5986    3.0908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8727    4.9811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1845    7.1414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0647    8.2996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2759    1.4705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9372    8.8739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0454    9.3591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8459    4.1710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1309    1.7405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8879    6.8817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4695    4.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1200    6.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3404    2.5507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4159    3.0908    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.5009    7.5560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0286    4.1710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7638    8.0294    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1577    2.5507    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.0290    6.9680    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5609    2.8207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5609    6.6014    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 18 17  2  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22 19  1  0  0  0  0
 23  4  1  0  0  0  0
 23  5  1  0  0  0  0
 24  6  1  1  0  0  0
 24 16  1  0  0  0  0
 25  7  1  6  0  0  0
 25 17  1  0  0  0  0
 26  8  1  1  0  0  0
 27  9  1  0  0  0  0
 28 20  1  0  0  0  0
 28 21  1  0  0  0  0
 29 19  1  0  0  0  0
 30 20  1  0  0  0  0
 31 18  1  0  0  0  0
 32 26  1  0  0  0  0
 33 23  1  0  0  0  0
 34 29  1  0  0  0  0
 35 24  1  0  0  0  0
 30 36  1  1  0  0  0
 37 32  1  0  0  0  0
 38 33  1  0  0  0  0
 32 39  1  6  0  0  0
 39 34  2  0  0  0  0
 40 10  1  0  0  0  0
 29 40  1  1  0  0  0
 40 35  1  0  0  0  0
 41 11  1  0  0  0  0
 33 41  1  6  0  0  0
 41 37  1  0  0  0  0
 42 21  1  0  0  0  0
 42 30  1  0  0  0  0
 42 38  1  0  0  0  0
 43 25  1  0  0  0  0
 43 31  1  0  0  0  0
 43 36  1  0  0  0  0
 44 27  2  0  0  0  0
 28 45  1  1  0  0  0
 46 31  2  0  0  0  0
 34 47  1  4  0  0  0
 48 35  2  0  0  0  0
 49 36  2  0  0  0  0
 50 37  2  0  0  0  0
 51 38  2  0  0  0  0
 52 26  1  0  0  0  0
 52 27  1  0  0  0  0
 24 53  1  6  0  0  0
 25 54  1  1  0  0  0
 26 55  1  6  0  0  0
 28 56  1  6  0  0  0
 29 57  1  1  0  0  0
 30 58  1  6  0  0  0
 32 59  1  1  0  0  0
 33 60  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0025336

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](C)(CCCCCC)C(=O)N(C)[C@@]([H])(CC(C)C)C(O)=N[C@]([H])(C(=O)N(C)[C@@]([H])(C(C)C)C(=O)N1C[C@@]([H])(O)C[C@@]1([H])C(=O)N1C(=O)C=C[C@]1([H])C)[C@@]([H])(C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C38H63N5O9/c1-12-13-14-15-16-24(6)35(48)40(10)29(19-22(2)3)34(47)39-32(26(8)52-27(9)44)37(50)41(11)33(23(4)5)38(51)42-21-28(45)20-30(42)36(49)43-25(7)17-18-31(43)46/h17-18,22-26,28-30,32-33,45H,12-16,19-21H2,1-11H3,(H,39,47)/t24-,25+,26-,28+,29+,30+,32+,33+/m1/s1

> <INCHI_KEY>
VVVUQZUDSPOQAQ-PEYQGHOASA-N

> <FORMULA>
C38H63N5O9

> <MOLECULAR_WEIGHT>
733.948

> <EXACT_MASS>
733.462578629

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
115

> <JCHEM_AVERAGE_POLARIZABILITY>
79.72444274640131

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-N-[(1S,2R)-2-(acetyloxy)-1-{[(2S)-1-[(2S,4S)-4-hydroxy-2-[(2S)-2-methyl-5-oxo-2,5-dihydro-1H-pyrrole-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl](methyl)carbamoyl}propyl]-2-[(2R)-N,2-dimethyloctanamido]-4-methylpentanimidic acid

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
3.6439145116666682

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.48124841406039

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.647899659516926

> <JCHEM_PKA_STRONGEST_BASIC>
0.502233771933104

> <JCHEM_POLAR_SURFACE_AREA>
177.42999999999998

> <JCHEM_REFRACTIVITY>
195.6832000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-N-[(1S,2R)-2-(acetyloxy)-1-{[(2S)-1-[(2S,4S)-4-hydroxy-2-[(2S)-2-methyl-5-oxo-2H-pyrrole-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl](methyl)carbamoyl}propyl]-2-[(2R)-N,2-dimethyloctanamido]-4-methylpentanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      18.640   3.753   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      33.483   4.257   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.610   1.737   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.319  10.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.192  12.827   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.207   6.778   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.741  14.200   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      36.975   7.282   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      38.721   5.265   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.826   7.282   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.684   8.794   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.095   3.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.260   4.257   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.715   3.753   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.879   4.761   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.334   4.257   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      41.365  16.918   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      40.136  17.847   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.864   3.753   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.119  15.803   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.417  13.984   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.319   3.249   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      33.483  11.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.498   5.265   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      40.860  15.463   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      35.811   6.274   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      37.557   4.257   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      34.607  15.512   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.573   5.265   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      36.864  14.455   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      38.873  16.966   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      34.356   6.778   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      34.938  10.810   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      31.737   6.274   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      27.953   4.761   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      38.392  14.264   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      34.065   8.290   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      36.102  11.818   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0      33.192   5.769   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0      29.117   5.769   0.000  0.00  0.00           N+0
HETATM   41  N   UNK     0      35.229   9.298   0.000  0.00  0.00           N+0
HETATM   42  N   UNK     0      35.811  13.331   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      39.321  15.493   0.000  0.00  0.00           N+0
HETATM   44  O   UNK     0      37.848   2.745   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      33.483  16.565   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      37.418  17.470   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      31.446   7.786   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      28.244   3.249   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      38.991  12.846   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      32.610   8.794   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      37.557  11.314   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      36.102   4.761   0.000  0.00  0.00           O+0
HETATM   53  H   UNK     0      25.043   5.769   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0      40.135  14.105   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0      35.520   7.786   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0      33.159  14.988   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0      32.028   4.761   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0      37.388  13.007   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0      34.647   5.265   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0      34.647  12.323   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5   23                                                            
CONECT    6   24                                                            
CONECT    7   25                                                            
CONECT    8   26                                                            
CONECT    9   27                                                            
CONECT   10   40                                                            
CONECT   11   41                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   24                                                       
CONECT   17   18   25                                                       
CONECT   18   17   31                                                       
CONECT   19   22   29                                                       
CONECT   20   28   30                                                       
CONECT   21   28   42                                                       
CONECT   22    2    3   19                                                  
CONECT   23    4    5   33                                                  
CONECT   24    6   16   35   53                                             
CONECT   25    7   17   43   54                                             
CONECT   26    8   32   52   55                                             
CONECT   27    9   44   52                                                  
CONECT   28   20   21   45   56                                             
CONECT   29   19   34   40   57                                             
CONECT   30   20   36   42   58                                             
CONECT   31   18   43   46                                                  
CONECT   32   26   37   39   59                                             
CONECT   33   23   38   41   60                                             
CONECT   34   29   39   47                                                  
CONECT   35   24   40   48                                                  
CONECT   36   30   43   49                                                  
CONECT   37   32   41   50                                                  
CONECT   38   33   42   51                                                  
CONECT   39   32   34                                                       
CONECT   40   10   29   35                                                  
CONECT   41   11   33   37                                                  
CONECT   42   21   30   38                                                  
CONECT   43   25   31   36                                                  
CONECT   44   27                                                            
CONECT   45   28                                                            
CONECT   46   31                                                            
CONECT   47   34                                                            
CONECT   48   35                                                            
CONECT   49   36                                                            
CONECT   50   37                                                            
CONECT   51   38                                                            
CONECT   52   26   27                                                       
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   28                                                            
CONECT   57   29                                                            
CONECT   58   30                                                            
CONECT   59   32                                                            
CONECT   60   33                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  122    0
END

Synonyms

Not Available

Molecular Formula

C₃₈H₆₃N₅O₉

Average Mass

733.948

Monoisotopic Mass

733.462578629

IUPAC Name

(2S)-N-[(1S,2R)-2-(acetyloxy)-1-{[(2S)-1-[(2S,4S)-4-hydroxy-2-[(2S)-2-methyl-5-oxo-2,5-dihydro-1H-pyrrole-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl](methyl)carbamoyl}propyl]-2-[(2R)-N,2-dimethyloctanamido]-4-methylpentanimidic acid

Traditional Name

(2S)-N-[(1S,2R)-2-(acetyloxy)-1-{[(2S)-1-[(2S,4S)-4-hydroxy-2-[(2S)-2-methyl-5-oxo-2H-pyrrole-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl](methyl)carbamoyl}propyl]-2-[(2R)-N,2-dimethyloctanamido]-4-methylpentanimidic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](C)(CCCCCC)C(=O)N(C)[C@@]([H])(CC(C)C)C(O)=N[C@]([H])(C(=O)N(C)[C@@]([H])(C(C)C)C(=O)N1C[C@@]([H])(O)C[C@@]1([H])C(=O)N1C(=O)C=C[C@]1([H])C)[C@@]([H])(C)OC(C)=O

InChI Identifier

InChI=1S/C38H63N5O9/c1-12-13-14-15-16-24(6)35(48)40(10)29(19-22(2)3)34(47)39-32(26(8)52-27(9)44)37(50)41(11)33(23(4)5)38(51)42-21-28(45)20-30(42)36(49)43-25(7)17-18-31(43)46/h17-18,22-26,28-30,32-33,45H,12-16,19-21H2,1-11H3,(H,39,47)/t24-,25+,26-,28+,29+,30+,32+,33+/m1/s1

InChI Key

VVVUQZUDSPOQAQ-PEYQGHOASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
Valine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Pyrrolidine-2-carboxamide
Pyrrolidine carboxylic acid or derivatives
N-acylpyrrolidine
Carboxylic acid imide, n-substituted
N-acyl-amine
Tertiary carboxylic acid amide
Pyrroline
Pyrrolidine
Dicarboximide
Carboxylic acid imide
Secondary alcohol
Carboxylic acid ester
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	3.9	ALOGPS
logP	3.64	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	0.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	177.43 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	195.68 m³·mol⁻¹	ChemAxon
Polarizability	79.72 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	77.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	85.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	728.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	742.7
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	706.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	134.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3663.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	204.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	341.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	576.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	166.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	145.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	254.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	9.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	112.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	172.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	556.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2236.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1542.8

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Microcolin H_TMS_1	CCCCCC[C@@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=N[C@H](C(=O)N(C)[C@H](C(=O)N1C[C@@H](O)C[C@H]1C(=O)N1C(=O)C=C[C@@H]1C)C(C)C)[C@@H](C)OC(C)=O)O[Si](C)(C)C	standard non polar	2025-10-23	1879.62
Gas Chromatography	Microcolin H_TMS_2	CCCCCC[C@@H](C)C(=O)N(C)[C@@H](CC(C)C)C(O)=N[C@H](C(=O)N(C)[C@H](C(=O)N1C[C@@H](O[Si](C)(C)C)C[C@H]1C(=O)N1C(=O)C=C[C@@H]1C)C(C)C)[C@@H](C)OC(C)=O	standard non polar	2025-10-23	1110.3
Gas Chromatography	Microcolin H_TMS_3	CCCCCC[C@@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=N[C@H](C(=O)N(C)[C@H](C(=O)N1C[C@@H](O[Si](C)(C)C)C[C@H]1C(=O)N1C(=O)C=C[C@@H]1C)C(C)C)[C@@H](C)OC(C)=O)O[Si](C)(C)C	standard non polar	2025-10-23	1920.86
Gas Chromatography	Microcolin H_TMS_1	CCCCCC[C@@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=N[C@H](C(=O)N(C)[C@H](C(=O)N1C[C@@H](O)C[C@H]1C(=O)N1C(=O)C=C[C@@H]1C)C(C)C)[C@@H](C)OC(C)=O)O[Si](C)(C)C	standard polar	2025-10-23	2862.77
Gas Chromatography	Microcolin H_TMS_2	CCCCCC[C@@H](C)C(=O)N(C)[C@@H](CC(C)C)C(O)=N[C@H](C(=O)N(C)[C@H](C(=O)N1C[C@@H](O[Si](C)(C)C)C[C@H]1C(=O)N1C(=O)C=C[C@@H]1C)C(C)C)[C@@H](C)OC(C)=O	standard polar	2025-10-23	2956.94
Gas Chromatography	Microcolin H_TMS_3	CCCCCC[C@@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=N[C@H](C(=O)N(C)[C@H](C(=O)N1C[C@@H](O[Si](C)(C)C)C[C@H]1C(=O)N1C(=O)C=C[C@@H]1C)C(C)C)[C@@H](C)OC(C)=O)O[Si](C)(C)C	standard polar	2025-10-23	284.901

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Cyanobacteria	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

81163320

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139292112

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Microcolin H (MMDBc0025336)

MOL for #<Metabolite:0x00007f9acc00ed08>

3D MOL for #<Metabolite:0x00007f9acc00ed08>

3D SDF for #<Metabolite:0x00007f9acc00ed08>

3D-SDF for #<Metabolite:0x00007f9acc00ed08>

PDB for #<Metabolite:0x00007f9acc00ed08>

3D PDB for #<Metabolite:0x00007f9acc00ed08>

SMILES for #<Metabolite:0x00007f9acc00ed08>

INCHI for #<Metabolite:0x00007f9acc00ed08>

Structure for #<Metabolite:0x00007f9acc00ed08>

3D Structure for #<Metabolite:0x00007f9acc00ed08>