MiMeDB: Showing metabocard for Stevastelin B3 (MMDBc0015843)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:37:04 UTC

Update Date

2025-10-07 16:06:28 UTC

Metabolite ID

MMDBc0015843

Metabolite Identification

Common Name

Stevastelin B3

Description

Stevastelin B3 is a member of the cyclic metabolite class, specifically characterized by its unique structure involving ester linkages. It is synthesized through a translactonization reaction from a [15]-membered ring derivative, resulting in the formation of the natural [13]-membered ring component of the stevastelins family (PMID:16277304 ). The chemical structure of stevastelin B3 includes an O-acetylserine moiety linked to a fatty acid moiety, where cyclic structures are formed via ester linkages between the carboxylic group of the O-acetylserine and the 3-hydroxy group of the fatty acid (PMID:8698640 ). Stevastelin B3 is involved in various biochemical pathways, although specific biological functions and mechanisms remain to be elucidated. Its synthesis and structural characteristics suggest potential roles in cellular processes, possibly related to signaling or metabolic regulation. The study of stevastelin B3 contributes to the understanding of the stevastelin family and its implications in biochemical research.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152108372D          

 54 54  0  0  1  0            999 V2000
  -10.0125    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0968    3.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5165    3.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099   -0.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7265    1.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0014    1.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5718   -0.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2980    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5836    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8691    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1546    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4401    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7257    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0112    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2967    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1533    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3923   -0.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8534    3.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748    1.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2378    1.7414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8082   -0.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2810    0.2260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7244    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9470    2.6784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5855    1.2363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7046    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3872    2.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106    2.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6969    0.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6287   -0.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0446   -0.0863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    2.1571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219    1.5486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1265    2.5589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1986    0.3282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2093    1.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470    2.9197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629    2.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4982    0.6150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400   -1.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1559   -0.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8651    0.0332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7244    0.0966    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637    2.0795    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3491    0.9240    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697    1.0435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5313    1.0931    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047    3.1764    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333    0.7312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4190    1.3341    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  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
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 22  4  1  0  0  0  0
 23  5  1  0  0  0  0
 24  6  1  0  0  0  0
 25  7  1  0  0  0  0
 26 20  1  6  0  0  0
 27 19  1  0  0  0  0
 27 22  1  0  0  0  0
 28 21  1  1  0  0  0
 29 24  1  6  0  0  0
 30 22  1  0  0  0  0
 30 23  1  0  0  0  0
 31 23  1  0  0  0  0
 32 28  1  0  0  0  0
 33 29  1  0  0  0  0
 34 26  1  0  0  0  0
 35 26  1  0  0  0  0
 35 33  2  0  0  0  0
 36 28  1  0  0  0  0
 36 31  2  0  0  0  0
 37 29  1  0  0  0  0
 37 32  2  0  0  0  0
 24 38  1  1  0  0  0
 39 25  2  0  0  0  0
 40 27  1  0  0  0  0
 31 41  1  4  0  0  0
 32 42  1  4  0  0  0
 33 43  1  4  0  0  0
 44 34  2  0  0  0  0
 45 20  1  0  0  0  0
 45 25  1  0  0  0  0
 46 30  1  0  0  0  0
 46 34  1  0  0  0  0
 47 22  1  0  0  0  0
 48 23  1  0  0  0  0
 24 49  1  1  0  0  0
 26 50  1  6  0  0  0
 51 27  1  0  0  0  0
 28 52  1  6  0  0  0
 29 53  1  6  0  0  0
 54 30  1  0  0  0  0
M  END


  Mrv1652305152108372D          

 54 54  0  0  1  0            999 V2000
  -10.0125    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0968    3.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5165    3.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099   -0.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7265    1.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0014    1.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5718   -0.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2980    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5836    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8691    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1546    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4401    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7257    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0112    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2967    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1533    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3923   -0.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8534    3.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748    1.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2378    1.7414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8082   -0.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2810    0.2260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7244    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9470    2.6784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5855    1.2363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7046    0.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3872    2.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106    2.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6969    0.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6287   -0.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0446   -0.0863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    2.1571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219    1.5486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1265    2.5589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1986    0.3282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2093    1.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470    2.9197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629    2.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4982    0.6150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400   -1.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1559   -0.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8651    0.0332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7244    0.0966    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637    2.0795    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3491    0.9240    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697    1.0435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5313    1.0931    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047    3.1764    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333    0.7312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4190    1.3341    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  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
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 22  4  1  0  0  0  0
 23  5  1  0  0  0  0
 24  6  1  0  0  0  0
 25  7  1  0  0  0  0
 26 20  1  6  0  0  0
 27 19  1  0  0  0  0
 27 22  1  0  0  0  0
 28 21  1  1  0  0  0
 29 24  1  6  0  0  0
 30 22  1  0  0  0  0
 30 23  1  0  0  0  0
 31 23  1  0  0  0  0
 32 28  1  0  0  0  0
 33 29  1  0  0  0  0
 34 26  1  0  0  0  0
 35 26  1  0  0  0  0
 35 33  2  0  0  0  0
 36 28  1  0  0  0  0
 36 31  2  0  0  0  0
 37 29  1  0  0  0  0
 37 32  2  0  0  0  0
 24 38  1  1  0  0  0
 39 25  2  0  0  0  0
 40 27  1  0  0  0  0
 31 41  1  4  0  0  0
 32 42  1  4  0  0  0
 33 43  1  4  0  0  0
 44 34  2  0  0  0  0
 45 20  1  0  0  0  0
 45 25  1  0  0  0  0
 46 30  1  0  0  0  0
 46 34  1  0  0  0  0
 47 22  1  0  0  0  0
 48 23  1  0  0  0  0
 24 49  1  1  0  0  0
 26 50  1  6  0  0  0
 51 27  1  0  0  0  0
 28 52  1  6  0  0  0
 29 53  1  6  0  0  0
 54 30  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0015843

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(O)[C@]1([H])N=C(O)[C@@]([H])(N=C(O)C([H])(C)C([H])(OC(=O)[C@]([H])(COC(C)=O)N=C1O)C([H])(C)C([H])(O)CCCCCCCCCCCCC)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C34H61N3O9/c1-8-9-10-11-12-13-14-15-16-17-18-19-27(40)22(4)30-23(5)31(41)36-28(21(2)3)32(42)37-29(24(6)38)33(43)35-26(34(44)46-30)20-45-25(7)39/h21-24,26-30,38,40H,8-20H2,1-7H3,(H,35,43)(H,36,41)(H,37,42)/t22?,23?,24-,26+,27?,28+,29+,30?/m1/s1

> <INCHI_KEY>
NVCZDYLTENUTNV-CSFMTDHRSA-N

> <FORMULA>
C34H61N3O9

> <MOLECULAR_WEIGHT>
655.874

> <EXACT_MASS>
655.440780556

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
107

> <JCHEM_AVERAGE_POLARIZABILITY>
75.42317102310486

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3S,6S,9S)-5,8,11-trihydroxy-6-[(1R)-1-hydroxyethyl]-13-(3-hydroxyhexadecan-2-yl)-12-methyl-2-oxo-9-(propan-2-yl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-3-yl]methyl acetate

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
4.148997753505038

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.8680783728249812

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.05872509725179

> <JCHEM_PKA_STRONGEST_BASIC>
7.852197433331108

> <JCHEM_POLAR_SURFACE_AREA>
190.82999999999996

> <JCHEM_REFRACTIVITY>
174.0363000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,6S,9S)-5,8,11-trihydroxy-6-[(1R)-1-hydroxyethyl]-13-(3-hydroxyhexadecan-2-yl)-9-isopropyl-12-methyl-2-oxo-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-3-yl]methyl acetate

> <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     -18.690   0.950   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.047   7.144   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.698   7.446   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.018  -0.590   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.356   2.349   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   2.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.534  -1.327   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -17.356   1.720   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -16.023   0.950   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.689   1.720   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -13.355   0.950   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.022   1.720   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.688   0.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.354   1.720   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.021   0.950   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.687   1.720   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.353   0.950   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.020   1.720   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.686   0.950   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.466  -1.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.460   6.530   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.018   0.950   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.140   2.715   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.911   3.251   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.109  -0.744   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.258   0.422   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.352   1.720   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.634   5.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.693   2.308   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.315   1.720   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.723   4.141   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.060   4.417   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.901   0.782   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.040  -0.521   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       5.683  -0.161   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0       2.258   4.027   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       5.268   2.891   0.000  0.00  0.00           N+0
HETATM   38  O   UNK     0       7.703   4.777   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       7.837   0.613   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -2.257   2.966   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -0.088   5.450   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       6.277   5.360   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       8.397   1.148   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       3.248  -2.047   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       5.891  -1.687   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       1.615   0.062   0.000  0.00  0.00           O+0
HETATM   47  H   UNK     0      -1.352   0.180   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.866   3.882   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       8.118   1.725   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.050   1.948   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.859   2.041   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.862   5.929   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.475   1.365   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.649   2.490   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   23                                                            
CONECT    6   24                                                            
CONECT    7   25                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   27                                                       
CONECT   20   26   45                                                       
CONECT   21    2    3   28                                                  
CONECT   22    4   27   30   47                                             
CONECT   23    5   30   31   48                                             
CONECT   24    6   29   38   49                                             
CONECT   25    7   39   45                                                  
CONECT   26   20   34   35   50                                             
CONECT   27   19   22   40   51                                             
CONECT   28   21   32   36   52                                             
CONECT   29   24   33   37   53                                             
CONECT   30   22   23   46   54                                             
CONECT   31   23   36   41                                                  
CONECT   32   28   37   42                                                  
CONECT   33   29   35   43                                                  
CONECT   34   26   44   46                                                  
CONECT   35   26   33                                                       
CONECT   36   28   31                                                       
CONECT   37   29   32                                                       
CONECT   38   24                                                            
CONECT   39   25                                                            
CONECT   40   27                                                            
CONECT   41   31                                                            
CONECT   42   32                                                            
CONECT   43   33                                                            
CONECT   44   34                                                            
CONECT   45   20   25                                                       
CONECT   46   30   34                                                       
CONECT   47   22                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   26                                                            
CONECT   51   27                                                            
CONECT   52   28                                                            
CONECT   53   29                                                            
CONECT   54   30                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  108    0
END

Synonyms

Value	Source
[(3S,6S,9S)-5,8,11-Trihydroxy-6-[(1R)-1-hydroxyethyl]-13-(3-hydroxyhexadecan-2-yl)-12-methyl-2-oxo-9-(propan-2-yl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-3-yl]methyl acetic acid	Generator

Molecular Formula

C₃₄H₆₁N₃O₉

Average Mass

655.874

Monoisotopic Mass

655.440780556

IUPAC Name

[(3S,6S,9S)-5,8,11-trihydroxy-6-[(1R)-1-hydroxyethyl]-13-(3-hydroxyhexadecan-2-yl)-12-methyl-2-oxo-9-(propan-2-yl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-3-yl]methyl acetate

Traditional Name

[(3S,6S,9S)-5,8,11-trihydroxy-6-[(1R)-1-hydroxyethyl]-13-(3-hydroxyhexadecan-2-yl)-9-isopropyl-12-methyl-2-oxo-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-3-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

[H][C@](C)(O)[C@]1([H])N=C(O)[C@@]([H])(N=C(O)C([H])(C)C([H])(OC(=O)[C@]([H])(COC(C)=O)N=C1O)C([H])(C)C([H])(O)CCCCCCCCCCCCC)C(C)C

InChI Identifier

InChI=1S/C34H61N3O9/c1-8-9-10-11-12-13-14-15-16-17-18-19-27(40)22(4)30-23(5)31(41)36-28(21(2)3)32(42)37-29(24(6)38)33(43)35-26(34(44)46-30)20-45-25(7)39/h21-24,26-30,38,40H,8-20H2,1-7H3,(H,35,43)(H,36,41)(H,37,42)/t22?,23?,24-,26+,27?,28+,29+,30?/m1/s1

InChI Key

NVCZDYLTENUTNV-CSFMTDHRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Macrolactam
Alpha-amino acid ester
Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
Secondary carboxylic acid amide
Secondary alcohol
Lactone
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
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	0.0077 g/L	ALOGPS
logP	4.5	ALOGPS
logP	4.15	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	2.06	ChemAxon
pKa (Strongest Basic)	7.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	190.83 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	174.04 m³·mol⁻¹	ChemAxon
Polarizability	75.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

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

8136825

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9961218

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 Stevastelin B3 (MMDBc0015843)

MOL for #<Metabolite:0x00007f8db70832b0>

3D MOL for #<Metabolite:0x00007f8db70832b0>

3D SDF for #<Metabolite:0x00007f8db70832b0>

3D-SDF for #<Metabolite:0x00007f8db70832b0>

PDB for #<Metabolite:0x00007f8db70832b0>

3D PDB for #<Metabolite:0x00007f8db70832b0>

SMILES for #<Metabolite:0x00007f8db70832b0>

INCHI for #<Metabolite:0x00007f8db70832b0>

Structure for #<Metabolite:0x00007f8db70832b0>

3D Structure for #<Metabolite:0x00007f8db70832b0>