SCS-C004421

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

Pathway: Terpenoids Superclass: Steroids Class: Cholestane steroids

Chemical Structure

Structure of (3R,5R,6R,8S,9S,10R,13R,14S,17R)-3,5,6-trihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-3,4,6,7,8,9,11,12,14,15,16,17-dodecahydro-2H-cyclopenta[a]phenanthren-1-one

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Source Information

Echinogorgia aurantiaca (NA)

Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Plexauridae Genus Echinogorgia Species Echinogorgia aurantiaca

South China Sea

DOI: 10.1039/b701534h · Natural Product Reports

Drug-likeness (Lipinski Ro5)

Molecular Weight

434.7 Da

Threshold ≤ 500

ALogP

4.73

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H46O4

Molecular Weight:

434.6610 Da

SMILES:

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@@H](O)CC(=O)[C@]4(C)[C@H]3CC[C@]12C

InChIKey:

                        NGKGCAWHVVDTNN-WBQNJBOJSA-N
                        
                    

InChI:

InChI=1S/C27H46O4/c1-16(2)7-6-8-17(3)20-9-10-21-19-14-24(30)27(31)15-18(28)13-23(29)26(27,5)22(19)11-12-25(20,21)4/h16-22,24,28,30-31H,6-15H2,1-5H3/t17-,18+,19+,20-,21+,22+,24-,25-,26+,27+/m1/s1

Calculated Properties

ALogP:

4.733 lipophilicity

TPSA:

77.76 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.9630 fraction sp³ carbon

Database Information

Compound ID:

SCS-C004421

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Steroids

NPClassifier Class:

Cholestane steroids

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD16370

Biological Activity Data

No bioactivity data available for this compound.

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