SCS-C004579

(3S,5S,8S,10R,12S,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,5,6,7,8,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol

Pathway: Terpenoids Superclass: Steroids Class: Ergostane steroids

Chemical Structure

Structure of (3S,5S,8S,10R,12S,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,5,6,7,8,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol

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Source Information

Litophyton chabrolii (NA)

Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Nephtheidae Genus Litophyton Species Litophyton chabrolii

South China Sea

DOI: 10.1248/cpb.51.1009 · Chemical and Pharmaceutical Bulletin

Drug-likeness (Lipinski Ro5)

Molecular Weight

430.7 Da

Threshold ≤ 500

ALogP

5.50

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

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]3CC[C@H]4C[C@@H](O)CC[C@]4(CO)C3=C[C@H](O)[C@]12C)C(C)C

InChIKey:

                        HNYHTTIKHMXVCJ-SCLMKZADSA-N
                        
                    

InChI:

InChI=1S/C28H46O3/c1-17(2)18(3)6-7-19(4)23-10-11-24-22-9-8-20-14-21(30)12-13-28(20,16-29)25(22)15-26(31)27(23,24)5/h15,17,19-24,26,29-31H,3,6-14,16H2,1-2,4-5H3/t19-,20+,21+,22+,23-,24+,26+,27-,28-/m1/s1

Calculated Properties

ALogP:

5.498 lipophilicity

TPSA:

60.69 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.8571 fraction sp³ carbon

Database Information

Compound ID:

SCS-C004579

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Steroids

NPClassifier Class:

Ergostane steroids

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD13733

Biological Activity Data

No bioactivity data available for this compound.

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