SCS-C003527

(2S,3R,4S,5S,8R,9S,10S,11S,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-2,3,8,11-tetrol

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

Chemical Structure

Structure of (2S,3R,4S,5S,8R,9S,10S,11S,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-2,3,8,11-tetrol

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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 sp. (soft coral)

Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species NA

Hainan Island

DOI: 10.1039/b701534h · Natural Product Reports

Drug-likeness (Lipinski Ro5)

Molecular Weight

462.7 Da

Threshold ≤ 500

ALogP

4.94

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C29H50O4

Molecular Weight:

462.7200 Da

SMILES:

C=C(CC[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)C[C@H](O)[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:

                        RCNRBDGMWATDJW-QBMAJCNVSA-N
                        
                    

InChI:

InChI=1S/C29H50O4/c1-16(2)17(3)8-9-18(4)20-10-11-24-27(20,6)15-23(31)26-28(7)14-22(30)25(32)19(5)21(28)12-13-29(24,26)33/h16,18-26,30-33H,3,8-15H2,1-2,4-7H3/t18-,19+,20-,21+,22+,23+,24-,25-,26-,27-,28+,29-/m1/s1

Calculated Properties

ALogP:

4.937 lipophilicity

TPSA:

80.92 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.9310 fraction sp³ carbon

Database Information

Compound ID:

SCS-C003527

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Steroids

NPClassifier Class:

Cholestane steroids Ergostane steroids

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD16366

Biological Activity Data

No bioactivity data available for this compound.

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