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

SCS-C003322

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

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

Structure of (2S,3R,4S,5S,8R,9R,10S,13R,14R,17R)-4,10,13-trimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-2,3,8-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.
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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
446.7 Da
Threshold ≤ 500
ALogP
5.97
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C29H50O3
Molecular Weight:
446.7160 Da
SMILES:
C=C(CC[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)C[C@H](O)[C@H](O)[C@@H](C)[C@@H]3CC[C@@]21O)C(C)C
InChIKey:
ZSJHRPGBMIOBJR-XLBYKDMESA-N
InChI:
InChI=1S/C29H50O3/c1-17(2)18(3)8-9-19(4)21-10-11-24-27(21,6)14-13-25-28(7)16-23(30)26(31)20(5)22(28)12-15-29(24,25)32/h17,19-26,30-32H,3,8-16H2,1-2,4-7H3/t19-,20+,21-,22+,23+,24-,25-,26-,27-,28+,29-/m1/s1
Calculated Properties
ALogP:
5.966 lipophilicity
TPSA:
60.69 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
3
Rotatable Bonds:
5
Ring Count:
4 (0 aromatic)
Chiral Centers:
11
Fsp³:
0.9310 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003322
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Cholestane steroids Ergostane steroids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD24173

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged