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  3. (3S,5R,6R,8S,9S,10R,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-17-[(E,2R)-6-methyl-5-methylidenehept-3-en-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5,6-triol

SCS-C003515

(3S,5R,6R,8S,9S,10R,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-17-[(E,2R)-6-methyl-5-methylidenehept-3-en-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5,6-triol

Pathway: Terpenoids Superclass: Steroids Class: Ergostane steroids
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Chemical Structure

Structure of (3S,5R,6R,8S,9S,10R,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-17-[(E,2R)-6-methyl-5-methylidenehept-3-en-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5,6-triol
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Download: SDF SMILES

Source Information

Sinularia sp. (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species NA
Hainan Island
DOI: 10.1002/hlca.200690132  · Helvetica Chimica Acta

Drug-likeness (Lipinski Ro5)

Molecular Weight
446.7 Da
Threshold ≤ 500
ALogP
4.47
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C28H46O4
Molecular Weight:
446.6700 Da
SMILES:
C=C(/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@@H](O)CC[C@]4(CO)[C@H]3CC[C@]12C)C(C)C
InChIKey:
IJPAWOHKBUAITQ-RWVFDGEJSA-N
InChI:
InChI=1S/C28H46O4/c1-17(2)18(3)6-7-19(4)22-8-9-23-21-14-25(31)28(32)15-20(30)10-13-27(28,16-29)24(21)11-12-26(22,23)5/h6-7,17,19-25,29-32H,3,8-16H2,1-2,4-5H3/b7-6+/t19-,20+,21+,22-,23+,24+,25-,26-,27+,28+/m1/s1
Calculated Properties
ALogP:
4.469 lipophilicity
TPSA:
80.92 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
4
Rotatable Bonds:
5
Ring Count:
4 (0 aromatic)
Chiral Centers:
10
Fsp³:
0.8571 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003515
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Ergostane steroids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD16367

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged