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  3. (4R,5S,8R,9S,10S,13R,14S,17R)-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-4,5,9,13,14-pentamethyl-1,2,4,6,7,8,10,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

SCS-C004975

(4R,5S,8R,9S,10S,13R,14S,17R)-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-4,5,9,13,14-pentamethyl-1,2,4,6,7,8,10,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

Pathway: Terpenoids Superclass: Triterpenoids Class: Cucurbitane triterpenoids | Shionane triterpenoids
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Chemical Structure

Structure of (4R,5S,8R,9S,10S,13R,14S,17R)-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-4,5,9,13,14-pentamethyl-1,2,4,6,7,8,10,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
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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

Talipariti tiliaceum (NA)
Kingdom Viridiplantae Phylum Streptophyta Class Magnoliopsida Order Malvales Family Malvaceae Genus Talipariti Species Talipariti tiliaceum
South China Sea
DOI: 10.1016/j.tet.2008.01.109  · Tetrahedron

Drug-likeness (Lipinski Ro5)

Molecular Weight
442.7 Da
Threshold ≤ 500
ALogP
7.59
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C30H50O2
Molecular Weight:
442.7280 Da
SMILES:
C[C@H](C/C=C/C(C)(C)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@]4(C)[C@@H](CCC(=O)[C@@H]4C)[C@]3(C)CC[C@]12C
InChIKey:
FLQDANIZFGMIBJ-BKMPTRIWSA-N
InChI:
InChI=1S/C30H50O2/c1-20(10-9-15-26(3,4)32)22-13-17-30(8)25-14-16-27(5)21(2)23(31)11-12-24(27)28(25,6)18-19-29(22,30)7/h9,15,20-22,24-25,32H,10-14,16-19H2,1-8H3/b15-9+/t20-,21+,22-,24-,25-,27-,28+,29-,30+/m1/s1
Calculated Properties
ALogP:
7.594 lipophilicity
TPSA:
37.30 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
2
Rotatable Bonds:
4
Ring Count:
4 (0 aromatic)
Chiral Centers:
9
Fsp³:
0.9000 fraction sp³ carbon

Database Information

Compound ID:
SCS-C004975
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Triterpenoids
NPClassifier Class:
Cucurbitane triterpenoids Shionane triterpenoids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD18548

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged