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  3. (3S,7S,8S,9S,10R,13R,14S,17R)-7-hydroperoxy-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

SCS-C003313

(3S,7S,8S,9S,10R,13R,14S,17R)-7-hydroperoxy-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

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

Structure of (3S,7S,8S,9S,10R,13R,14S,17R)-7-hydroperoxy-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
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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 depressa (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species Sinularia depressa
Lingshui
DOI: 10.1039/c4np00144c  · Natural Product Reports
Sinularia depressa (soft coral)
Original source name: Sinularia depressa Tixier-Durivault
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species Sinularia depressa
South China Sea
DOI: 10.1016/j.bmcl.2012.12.087  · Bioorganic & Medicinal Chemistry Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight
430.7 Da
Threshold ≤ 500
ALogP
7.02
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C28H46O3
Molecular Weight:
430.6730 Da
SMILES:
C=C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](OO)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C
InChIKey:
YERLWYOMTABZTA-JEPZXVLISA-N
InChI:
InChI=1S/C28H46O3/c1-17(2)18(3)7-8-19(4)22-9-10-23-26-24(12-14-28(22,23)6)27(5)13-11-21(29)15-20(27)16-25(26)31-30/h16-17,19,21-26,29-30H,3,7-15H2,1-2,4-6H3/t19-,21+,22-,23+,24+,25-,26+,27+,28-/m1/s1
Calculated Properties
ALogP:
7.023 lipophilicity
TPSA:
49.69 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
3
Rotatable Bonds:
6
Ring Count:
4 (0 aromatic)
Chiral Centers:
9
Fsp³:
0.8571 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003313
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: CMNPD24174

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged