MiMeDB: Showing metabocard for Nidulanin A (MMDBc0028202)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 17:50:13 UTC

Update Date

2025-10-07 16:07:49 UTC

Metabolite ID

MMDBc0028202

Metabolite Identification

Common Name

Nidulanin A

Description

Nidulanin A is a cyclic tetrapeptide belonging to the class of nonribosomal peptides. Its biosynthesis involves a non-ribosomal peptide synthetase (NRPS) gene, which is regulated by genetic factors in the filamentous fungus Aspergillus nidulans. Research has shown that mutations can upregulate the transcription of this NRPS gene, enhancing nidulanin A production (PMID:27775185 ). Additionally, studies utilizing SILAAs (synthetic amino acid analogs) incorporated into cultivation media have confirmed their integration into nidulanin A, allowing for the analysis of its chemical structure through changes in observed mass-to-charge ratios (PMID:26020678 ). The compound has been linked to various biosynthetic gene clusters (BGCs), with significant similarities noted to other metabolites such as chaetoglobosin A and squalestatin S1 (PMID:38142242 ). Furthermore, data clustering approaches have identified cross-chemistry between distinct gene clusters, validating the involvement of specific synthases and prenyltransferases in nidulanin A production (PMID:2324 ...). Overall, nidulanin A exemplifies the intricate interplay of genetic regulation and chemical synthesis pathways in fungal metabolism.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152119502D          

 48 50  0  0  1  0            999 V2000
    8.3309    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9184    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    0.5230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3809    2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6184    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270    0.5230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7934    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.3480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    2.7770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.5230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    3.4914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    3.4914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.3645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.1914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  2  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 21  4  1  0  0  0  0
 21  5  1  0  0  0  0
 22 14  2  0  0  0  0
 22 15  1  0  0  0  0
 22 18  1  0  0  0  0
 23 16  2  0  0  0  0
 24 17  2  0  0  0  0
 24 23  1  0  0  0  0
 25 18  1  1  0  0  0
 26 19  1  1  0  0  0
 27 19  1  0  0  0  0
 27 23  1  0  0  0  0
 28 20  1  1  0  0  0
 29 21  1  6  0  0  0
 30 26  1  0  0  0  0
 31 25  1  0  0  0  0
 32 28  1  0  0  0  0
 33 29  1  0  0  0  0
 34  6  1  0  0  0  0
 34  7  1  0  0  0  0
 34  8  1  0  0  0  0
 35 25  1  0  0  0  0
 35 30  2  0  0  0  0
 36 26  1  0  0  0  0
 36 32  2  0  0  0  0
 37 29  1  0  0  0  0
 37 31  2  0  0  0  0
 38 28  1  0  0  0  0
 38 33  2  0  0  0  0
 39 24  1  0  0  0  0
 39 34  1  0  0  0  0
 40 27  2  0  0  0  0
 30 41  1  4  0  0  0
 31 42  1  4  0  0  0
 32 43  1  4  0  0  0
 33 44  1  4  0  0  0
 25 45  1  6  0  0  0
 26 46  1  6  0  0  0
 28 47  1  6  0  0  0
 29 48  1  1  0  0  0
M  END


  Mrv1652305152119502D          

 48 50  0  0  1  0            999 V2000
    8.3309    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9184    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    0.5230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3809    2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6184    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270    0.5230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7934    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.3480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    2.7770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.5230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    3.4914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    3.4914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.3645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.1914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  2  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 21  4  1  0  0  0  0
 21  5  1  0  0  0  0
 22 14  2  0  0  0  0
 22 15  1  0  0  0  0
 22 18  1  0  0  0  0
 23 16  2  0  0  0  0
 24 17  2  0  0  0  0
 24 23  1  0  0  0  0
 25 18  1  1  0  0  0
 26 19  1  1  0  0  0
 27 19  1  0  0  0  0
 27 23  1  0  0  0  0
 28 20  1  1  0  0  0
 29 21  1  6  0  0  0
 30 26  1  0  0  0  0
 31 25  1  0  0  0  0
 32 28  1  0  0  0  0
 33 29  1  0  0  0  0
 34  6  1  0  0  0  0
 34  7  1  0  0  0  0
 34  8  1  0  0  0  0
 35 25  1  0  0  0  0
 35 30  2  0  0  0  0
 36 26  1  0  0  0  0
 36 32  2  0  0  0  0
 37 29  1  0  0  0  0
 37 31  2  0  0  0  0
 38 28  1  0  0  0  0
 38 33  2  0  0  0  0
 39 24  1  0  0  0  0
 39 34  1  0  0  0  0
 40 27  2  0  0  0  0
 30 41  1  4  0  0  0
 31 42  1  4  0  0  0
 32 43  1  4  0  0  0
 33 44  1  4  0  0  0
 25 45  1  6  0  0  0
 26 46  1  6  0  0  0
 28 47  1  6  0  0  0
 29 48  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0028202

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC(=O)C2=CC=CC=C2NC(C)(C)C=C)N=C(O)[C@@]([H])(N=C(O)[C@]([H])(N=C(O)[C@]([H])(CC2=CC=CC=C2)N=C1O)C(C)C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C34H45N5O5/c1-8-34(6,7)39-24-17-13-12-16-23(24)27(40)19-26-30(41)35-25(18-22-14-10-9-11-15-22)31(42)37-29(21(4)5)33(44)38-28(20(2)3)32(43)36-26/h8-17,20-21,25-26,28-29,39H,1,18-19H2,2-7H3,(H,35,41)(H,36,43)(H,37,42)(H,38,44)/t25-,26-,28-,29+/m0/s1

> <INCHI_KEY>
LNEVFEMBQYJQGA-ZSLRCHCDSA-N

> <FORMULA>
C34H45N5O5

> <MOLECULAR_WEIGHT>
603.764

> <EXACT_MASS>
603.342069569

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
65.7478353018361

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2S,5S,8R,11S)-5-benzyl-3,6,9,12-tetrahydroxy-8,11-bis(propan-2-yl)-1,4,7,10-tetraazacyclododeca-1(12),3,6,9-tetraen-2-yl]-1-{2-[(2-methylbut-3-en-2-yl)amino]phenyl}ethan-1-one

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
4.601554322227884

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.425538716132923

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.0730281518211884

> <JCHEM_PKA_STRONGEST_BASIC>
6.2533183921301205

> <JCHEM_POLAR_SURFACE_AREA>
159.45999999999998

> <JCHEM_REFRACTIVITY>
172.15260000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2S,5S,8R,11S)-5-benzyl-3,6,9,12-tetrahydroxy-8,11-diisopropyl-1,4,7,10-tetraazacyclododeca-1(12),3,6,9-tetraen-2-yl]-1-{2-[(2-methylbut-3-en-2-yl)amino]phenyl}ethanone

> <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      15.551   5.184   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.564   5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770   7.494   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104  -1.691   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.206  -0.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.241   4.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.241   8.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.781   6.517   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.645  -4.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.978  -3.644   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.311  -3.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.391  10.518   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.931  10.518   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.978  -2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.311  -2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.621   9.185   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.701   9.185   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.645   0.206   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081   6.517   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.770   5.954   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.357   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.645  -1.334   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.391   7.851   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.931   7.851   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.311   0.976   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.311   5.184   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.621   6.517   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.104   5.184   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.104   0.976   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.081   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.977   0.206   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.437   5.954   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.241   6.517   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       6.311   2.516   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0       4.771   5.184   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       3.644   0.976   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0       2.104   3.644   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0      11.701   6.517   0.000  0.00  0.00           N+0
HETATM   40  O   UNK     0       9.391   5.184   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       8.621   3.850   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       4.977  -1.334   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       3.437   7.494   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -0.206   2.310   0.000  0.00  0.00           O+0
HETATM   45  H   UNK     0       6.311  -0.564   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.541   6.517   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.770   4.414   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.874  -0.357   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5   21                                                            
CONECT    6   34                                                            
CONECT    7   34                                                            
CONECT    8    1   34                                                       
CONECT    9   10   11                                                       
CONECT   10    9   14                                                       
CONECT   11    9   15                                                       
CONECT   12   13   16                                                       
CONECT   13   12   17                                                       
CONECT   14   10   22                                                       
CONECT   15   11   22                                                       
CONECT   16   12   23                                                       
CONECT   17   13   24                                                       
CONECT   18   22   25                                                       
CONECT   19   26   27                                                       
CONECT   20    2    3   28                                                  
CONECT   21    4    5   29                                                  
CONECT   22   14   15   18                                                  
CONECT   23   16   24   27                                                  
CONECT   24   17   23   39                                                  
CONECT   25   18   31   35   45                                             
CONECT   26   19   30   36   46                                             
CONECT   27   19   23   40                                                  
CONECT   28   20   32   38   47                                             
CONECT   29   21   33   37   48                                             
CONECT   30   26   35   41                                                  
CONECT   31   25   37   42                                                  
CONECT   32   28   36   43                                                  
CONECT   33   29   38   44                                                  
CONECT   34    6    7    8   39                                             
CONECT   35   25   30                                                       
CONECT   36   26   32                                                       
CONECT   37   29   31                                                       
CONECT   38   28   33                                                       
CONECT   39   24   34                                                       
CONECT   40   27                                                            
CONECT   41   30                                                            
CONECT   42   31                                                            
CONECT   43   32                                                            
CONECT   44   33                                                            
CONECT   45   25                                                            
CONECT   46   26                                                            
CONECT   47   28                                                            
CONECT   48   29                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  100    0
END

Synonyms

Not Available

Molecular Formula

C₃₄H₄₅N₅O₅

Average Mass

603.764

Monoisotopic Mass

603.342069569

IUPAC Name

2-[(2S,5S,8R,11S)-5-benzyl-3,6,9,12-tetrahydroxy-8,11-bis(propan-2-yl)-1,4,7,10-tetraazacyclododeca-1(12),3,6,9-tetraen-2-yl]-1-{2-[(2-methylbut-3-en-2-yl)amino]phenyl}ethan-1-one

Traditional Name

2-[(2S,5S,8R,11S)-5-benzyl-3,6,9,12-tetrahydroxy-8,11-diisopropyl-1,4,7,10-tetraazacyclododeca-1(12),3,6,9-tetraen-2-yl]-1-{2-[(2-methylbut-3-en-2-yl)amino]phenyl}ethanone

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC(=O)C2=CC=CC=C2NC(C)(C)C=C)N=C(O)[C@@]([H])(N=C(O)[C@]([H])(N=C(O)[C@]([H])(CC2=CC=CC=C2)N=C1O)C(C)C)C(C)C

InChI Identifier

InChI=1S/C34H45N5O5/c1-8-34(6,7)39-24-17-13-12-16-23(24)27(40)19-26-30(41)35-25(18-22-14-10-9-11-15-22)31(42)37-29(21(4)5)33(44)38-28(20(2)3)32(43)36-26/h8-17,20-21,25-26,28-29,39H,1,18-19H2,2-7H3,(H,35,41)(H,36,43)(H,37,42)(H,38,44)/t25-,26-,28-,29+/m0/s1

InChI Key

LNEVFEMBQYJQGA-ZSLRCHCDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Alkyl-phenylketone
Macrolactam
Alpha-amino acid or derivatives
Phenylketone
Phenylalkylamine
Aniline or substituted anilines
Aryl alkyl ketone
Aryl ketone
Benzoyl
Secondary aliphatic/aromatic amine
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Secondary carboxylic acid amide
Lactam
Ketone
Carboxamide group
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0068 g/L	ALOGPS
logP	4.38	ALOGPS
logP	4.6	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	-2.1	ChemAxon
pKa (Strongest Basic)	6.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	159.46 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	172.15 m³·mol⁻¹	ChemAxon
Polarizability	65.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	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

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
Eukaryota/Fungi	Ascomycota	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146684594

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 Nidulanin A (MMDBc0028202)

MOL for #<Metabolite:0x00007f8de9023b80>

3D MOL for #<Metabolite:0x00007f8de9023b80>

3D SDF for #<Metabolite:0x00007f8de9023b80>

3D-SDF for #<Metabolite:0x00007f8de9023b80>

PDB for #<Metabolite:0x00007f8de9023b80>

3D PDB for #<Metabolite:0x00007f8de9023b80>

SMILES for #<Metabolite:0x00007f8de9023b80>

INCHI for #<Metabolite:0x00007f8de9023b80>

Structure for #<Metabolite:0x00007f8de9023b80>

3D Structure for #<Metabolite:0x00007f8de9023b80>