MiMeDB: Showing metabocard for Sterolic acid (MMDBc0016762)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:19:23 UTC

Update Date

2025-10-07 16:06:35 UTC

Metabolite ID

MMDBc0016762

Metabolite Identification

Common Name

Sterolic acid

Description

Sterolic acid is a unique acetylenic fatty acid belonging to the chemical class of sterols. Its chemical structure features a distinctive alkyne functional group, which contributes to its reactivity and potential biological roles. Sterolic acid has been identified as a metabolite in various organisms, including fungi, where it is isolated from species such as Penicillium sp. (PMID:22412815 ). This compound is notable for its presence in oils, where it contributes to the profile of unsaturated fatty acids, comprising 89.41% of the total fatty acid content in certain extracts (PMID:30905238 ). The pathways involving sterolic acid may include lipid metabolism and signaling processes, although specific biological functions remain to be fully elucidated. Additionally, sterolic acid shares structural similarities with other compounds like cholic acid, acitretin, and mupirocin, indicating potential interactions within metabolic pathways (PMID:35372666 ). Overall, sterolic acid represents a fascinating area of study within the realm of lipid biochemistry and its implications in various biological contexts.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152109192D          

 46 52  0  0  1  0            999 V2000
    0.1096   -3.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -0.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5752   -2.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1169    0.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627   -2.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606   -1.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905    0.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1134    1.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2812   -0.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460   -0.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7722    0.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329   -2.8842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2351   -0.8062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2519   -2.7847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0882   -0.0472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8984    0.9501    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7064    1.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630    2.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7174    1.7258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6230    0.9029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0554    2.2305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8133    0.7444    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7476   -3.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516    1.1754    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9208    0.0873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3558    0.6202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2073    2.0488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4772    3.2873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4765    2.0490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5666   -3.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4243   -4.2032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580   -0.0946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3554    0.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    2.8531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817   -2.3242    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796   -1.3662    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3860   -2.9837    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584   -1.5652    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7563   -2.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5967   -0.6969    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9273    1.7746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3785    1.2323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2294    0.3436    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6192    2.8327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9454    1.5587    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 13  1  1  1  0  0  0
 13  5  1  0  0  0  0
 14  2  1  1  0  0  0
 14  6  1  0  0  0  0
 15  3  1  6  0  0  0
 15 13  1  0  0  0  0
 16  7  1  0  0  0  0
 16 14  1  1  0  0  0
 17  8  1  0  0  0  0
 18 11  2  0  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 21 20  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24 15  1  0  0  0  0
 25  4  1  1  0  0  0
 25 23  1  0  0  0  0
 26  9  1  6  0  0  0
 26 12  1  0  0  0  0
 26 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 10  1  0  0  0  0
 27 18  1  0  0  0  0
 27 25  1  0  0  0  0
 28 19  1  0  0  0  0
 28 22  1  0  0  0  0
 28 25  1  0  0  0  0
 29 19  2  0  0  0  0
 20 30  1  6  0  0  0
 31 24  2  0  0  0  0
 32 24  1  0  0  0  0
 33 12  1  0  0  0  0
 27 33  1  1  0  0  0
 34 21  1  0  0  0  0
 34 23  1  0  0  0  0
 35 22  1  0  0  0  0
 28 35  1  6  0  0  0
 36  5  1  0  0  0  0
 37  6  1  0  0  0  0
 13 38  1  6  0  0  0
 14 39  1  6  0  0  0
 15 40  1  1  0  0  0
 16 41  1  6  0  0  0
 17 42  1  6  0  0  0
 20 43  1  1  0  0  0
 21 44  1  1  0  0  0
 22 45  1  1  0  0  0
 23 46  1  1  0  0  0
M  END


  Mrv1652305152109192D          

 46 52  0  0  1  0            999 V2000
    0.1096   -3.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -0.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5752   -2.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1169    0.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627   -2.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606   -1.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905    0.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1134    1.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2812   -0.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460   -0.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7722    0.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329   -2.8842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2351   -0.8062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2519   -2.7847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0882   -0.0472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8984    0.9501    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7064    1.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630    2.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7174    1.7258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6230    0.9029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0554    2.2305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8133    0.7444    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7476   -3.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516    1.1754    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9208    0.0873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3558    0.6202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2073    2.0488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4772    3.2873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4765    2.0490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5666   -3.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4243   -4.2032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580   -0.0946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3554    0.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    2.8531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817   -2.3242    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796   -1.3662    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3860   -2.9837    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584   -1.5652    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7563   -2.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5967   -0.6969    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9273    1.7746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3785    1.2323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2294    0.3436    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6192    2.8327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9454    1.5587    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 13  1  1  1  0  0  0
 13  5  1  0  0  0  0
 14  2  1  1  0  0  0
 14  6  1  0  0  0  0
 15  3  1  6  0  0  0
 15 13  1  0  0  0  0
 16  7  1  0  0  0  0
 16 14  1  1  0  0  0
 17  8  1  0  0  0  0
 18 11  2  0  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 21 20  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24 15  1  0  0  0  0
 25  4  1  1  0  0  0
 25 23  1  0  0  0  0
 26  9  1  6  0  0  0
 26 12  1  0  0  0  0
 26 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 10  1  0  0  0  0
 27 18  1  0  0  0  0
 27 25  1  0  0  0  0
 28 19  1  0  0  0  0
 28 22  1  0  0  0  0
 28 25  1  0  0  0  0
 29 19  2  0  0  0  0
 20 30  1  6  0  0  0
 31 24  2  0  0  0  0
 32 24  1  0  0  0  0
 33 12  1  0  0  0  0
 27 33  1  1  0  0  0
 34 21  1  0  0  0  0
 34 23  1  0  0  0  0
 35 22  1  0  0  0  0
 28 35  1  6  0  0  0
 36  5  1  0  0  0  0
 37  6  1  0  0  0  0
 13 38  1  6  0  0  0
 14 39  1  6  0  0  0
 15 40  1  1  0  0  0
 16 41  1  6  0  0  0
 17 42  1  6  0  0  0
 20 43  1  1  0  0  0
 21 44  1  1  0  0  0
 22 45  1  1  0  0  0
 23 46  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0016762

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])C3=CC(=O)[C@@]45O[C@]4([H])[C@]([H])(O)[C@]4([H])O[C@]4([H])[C@]5(C)[C@]33CC[C@]12CO3)[C@]([H])(C)[C@]([H])(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O7/c1-13(15(3)24(31)32)5-6-14(2)16-7-8-17-18-11-19(29)28-22(35-28)20(30)21-23(34-21)25(28,4)27(18)10-9-26(16,17)12-33-27/h5-6,11,13-17,20-23,30H,7-10,12H2,1-4H3,(H,31,32)/b6-5+/t13-,14+,15-,16+,17-,20+,21-,22+,23-,25+,26-,27-,28+/m0/s1

> <INCHI_KEY>
WQTCLVQYDLVATO-GRTLLFEISA-N

> <FORMULA>
C28H36O7

> <MOLECULAR_WEIGHT>
484.589

> <EXACT_MASS>
484.246103499

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.68654034487622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4E,6R)-6-[(1S,2R,3R,5S,6R,7R,9S,13R,16R,17S)-6-hydroxy-2-methyl-10-oxo-4,8,19-trioxaheptacyclo[15.2.2.0^{1,12}.0^{2,9}.0^{3,5}.0^{7,9}.0^{13,17}]henicos-11-en-16-yl]-2,3-dimethylhept-4-enoic acid

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
3.106740181666664

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.019400452702467

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.65551653493908

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6651038220604857

> <JCHEM_POLAR_SURFACE_AREA>
108.89

> <JCHEM_REFRACTIVITY>
126.25799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4E,6R)-6-[(1S,2R,3R,5S,6R,7R,9S,13R,16R,17S)-6-hydroxy-2-methyl-10-oxo-4,8,19-trioxaheptacyclo[15.2.2.0^{1,12}.0^{2,9}.0^{3,5}.0^{7,9}.0^{13,17}]henicos-11-en-16-yl]-2,3-dimethylhept-4-enoic 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       0.205  -6.801   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.968  -1.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.940  -3.781   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.818   0.659   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.117  -4.153   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.486  -2.736   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.729   1.203   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.212   2.454   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.392  -1.324   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.819  -0.589   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.227   3.895   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.308   0.392   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.808  -5.384   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.439  -1.505   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.337  -5.198   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.165  -0.088   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.677   1.774   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.185   2.349   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.598   4.596   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.806   3.221   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.630   1.685   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.570   4.164   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.118   1.389   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.262  -6.429   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.696   2.194   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.719   0.163   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.397   1.158   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.987   3.824   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.624   6.136   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.223   3.825   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.791  -6.243   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.659  -7.846   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.962  -0.177   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       8.130   0.229   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       6.556   5.326   0.000  0.00  0.00           O+0
HETATM   36  H   UNK     0      -1.646  -4.339   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.015  -2.550   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.721  -5.570   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.042  -2.922   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.412  -3.967   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.114  -1.301   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.731   3.313   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      10.040   2.300   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       9.762   0.641   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       8.623   5.288   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       7.365   2.910   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   25                                                            
CONECT    5    6   13   36                                                  
CONECT    6    5   14   37                                                  
CONECT    7    8   16                                                       
CONECT    8    7   17                                                       
CONECT    9   10   26                                                       
CONECT   10    9   27                                                       
CONECT   11   18   19                                                       
CONECT   12   26   33                                                       
CONECT   13    1    5   15   38                                             
CONECT   14    2    6   16   39                                             
CONECT   15    3   13   24   40                                             
CONECT   16    7   14   26   41                                             
CONECT   17    8   18   26   42                                             
CONECT   18   11   17   27                                                  
CONECT   19   11   28   29                                                  
CONECT   20   21   22   30   43                                             
CONECT   21   20   23   34   44                                             
CONECT   22   20   28   35   45                                             
CONECT   23   21   25   34   46                                             
CONECT   24   15   31   32                                                  
CONECT   25    4   23   27   28                                             
CONECT   26    9   12   16   17                                             
CONECT   27   10   18   25   33                                             
CONECT   28   19   22   25   35                                             
CONECT   29   19                                                            
CONECT   30   20                                                            
CONECT   31   24                                                            
CONECT   32   24                                                            
CONECT   33   12   27                                                       
CONECT   34   21   23                                                       
CONECT   35   22   28                                                       
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38   13                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
CONECT   43   20                                                            
CONECT   44   21                                                            
CONECT   45   22                                                            
CONECT   46   23                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  104    0
END

Synonyms

Value	Source
Sterolate	Generator

Molecular Formula

C₂₈H₃₆O₇

Average Mass

484.589

Monoisotopic Mass

484.246103499

IUPAC Name

(2S,3S,4E,6R)-6-[(1S,2R,3R,5S,6R,7R,9S,13R,16R,17S)-6-hydroxy-2-methyl-10-oxo-4,8,19-trioxaheptacyclo[15.2.2.0^{1,12}.0^{2,9}.0^{3,5}.0^{7,9}.0^{13,17}]henicos-11-en-16-yl]-2,3-dimethylhept-4-enoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])C3=CC(=O)[C@@]45O[C@]4([H])[C@]([H])(O)[C@]4([H])O[C@]4([H])[C@]5(C)[C@]33CC[C@]12CO3)[C@]([H])(C)[C@]([H])(C)C(O)=O

InChI Identifier

InChI=1S/C28H36O7/c1-13(15(3)24(31)32)5-6-14(2)16-7-8-17-18-11-19(29)28-22(35-28)20(30)21-23(34-21)25(28,4)27(18)10-9-26(16,17)12-33-27/h5-6,11,13-17,20-23,30H,7-10,12H2,1-4H3,(H,31,32)/b6-5+/t13-,14+,15-,16+,17-,20+,21-,22+,23-,25+,26-,27-,28+/m0/s1

InChI Key

WQTCLVQYDLVATO-GRTLLFEISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergostane steroids

Alternative Parents

Substituents

Ergostane-skeleton
Naphthopyran
Naphthalene
Medium-chain fatty acid
Branched fatty acid
Oxepane
Cyclohexenone
Methyl-branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Oxane
Unsaturated fatty acid
Pyran
Fatty acid
Fatty acyl
Cyclic alcohol
Ketone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.01 g/L	ALOGPS
logP	2.65	ALOGPS
logP	3.11	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.89 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.26 m³·mol⁻¹	ChemAxon
Polarizability	52.69 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

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	248.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	60.3
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	471.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	583.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	635.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	176.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3055.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	87.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	353.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	532.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	157.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	156.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	190.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	9.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	222.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	155.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	460.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1583.1
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1095.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Sterolic acid_TMS_1	C[C@@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=CC(=O)[C@@]45O[C@@H]4[C@H](O[Si](C)(C)C)[C@@H]4O[C@@H]4[C@]5(C)[C@]34CC[C@@]21CO4)[C@H](C)C(=O)O	standard non polar	2025-10-23	2500.38
Gas Chromatography	Sterolic acid_TMS_2	C[C@@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=CC(=O)[C@@]45O[C@@H]4[C@H](O)[C@@H]4O[C@@H]4[C@]5(C)[C@]34CC[C@@]21CO4)[C@H](C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1574.4
Gas Chromatography	Sterolic acid_TMS_3	C[C@@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=CC(=O)[C@@]45O[C@@H]4[C@H](O[Si](C)(C)C)[C@@H]4O[C@@H]4[C@]5(C)[C@]34CC[C@@]21CO4)[C@H](C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2077.14
Gas Chromatography	Sterolic acid_TMS_1	C[C@@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=CC(=O)[C@@]45O[C@@H]4[C@H](O[Si](C)(C)C)[C@@H]4O[C@@H]4[C@]5(C)[C@]34CC[C@@]21CO4)[C@H](C)C(=O)O	standard polar	2025-10-23	1846.59
Gas Chromatography	Sterolic acid_TMS_2	C[C@@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=CC(=O)[C@@]45O[C@@H]4[C@H](O)[C@@H]4O[C@@H]4[C@]5(C)[C@]34CC[C@@]21CO4)[C@H](C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2033.43
Gas Chromatography	Sterolic acid_TMS_3	C[C@@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=CC(=O)[C@@]45O[C@@H]4[C@H](O[Si](C)(C)C)[C@@H]4O[C@@H]4[C@]5(C)[C@]34CC[C@@]21CO4)[C@H](C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1434.04

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

29214754

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587716

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 Sterolic acid (MMDBc0016762)

MOL for #<Metabolite:0x000056431f8719b0>

3D MOL for #<Metabolite:0x000056431f8719b0>

3D SDF for #<Metabolite:0x000056431f8719b0>

3D-SDF for #<Metabolite:0x000056431f8719b0>

PDB for #<Metabolite:0x000056431f8719b0>

3D PDB for #<Metabolite:0x000056431f8719b0>

SMILES for #<Metabolite:0x000056431f8719b0>

INCHI for #<Metabolite:0x000056431f8719b0>

Structure for #<Metabolite:0x000056431f8719b0>

3D Structure for #<Metabolite:0x000056431f8719b0>