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  3. (3S,4S,5R,10S,13R,14R,17R)-3-hydroxy-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-4,10,13,14-tetramethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-4-carboxylic acid

SCS-C002790

(3S,4S,5R,10S,13R,14R,17R)-3-hydroxy-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-4,10,13,14-tetramethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-4-carboxylic acid

Pathway: Terpenoids Superclass: Triterpenoids Class: Lanostane, Tirucallane and Euphane triterpenoids
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Chemical Structure

Structure of (3S,4S,5R,10S,13R,14R,17R)-3-hydroxy-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-4,10,13,14-tetramethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-4-carboxylic acid
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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

Bruguiera rhynchopetala (NA)
Kingdom Viridiplantae Phylum Streptophyta Class Magnoliopsida Order Malpighiales Family Rhizophoraceae Genus Bruguiera Species Bruguiera rhynchopetala
Hainan Island
DOI: 10.1039/c2np00090c

Drug-likeness (Lipinski Ro5)

Molecular Weight
472.7 Da
Threshold ≤ 500
ALogP
6.51
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C30H48O4
Molecular Weight:
472.7100 Da
SMILES:
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@]2(C)C3=CC[C@H]4[C@](C)(C(=O)O)[C@@H](O)CC[C@]4(C)C3=CC[C@]12C
InChIKey:
ZOBCPMSSZRVGKY-YIFTVCCYSA-N
InChI:
InChI=1S/C30H48O4/c1-19(9-8-15-26(2,3)34)20-12-17-29(6)22-10-11-23-27(4,21(22)13-18-28(20,29)5)16-14-24(31)30(23,7)25(32)33/h10,13,19-20,23-24,31,34H,8-9,11-12,14-18H2,1-7H3,(H,32,33)/t19-,20-,23-,24+,27-,28-,29+,30+/m1/s1
Calculated Properties
ALogP:
6.515 lipophilicity
TPSA:
77.76 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
3
Rotatable Bonds:
6
Ring Count:
4 (0 aromatic)
Chiral Centers:
8
Fsp³:
0.8333 fraction sp³ carbon

Database Information

Compound ID:
SCS-C002790
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Triterpenoids
NPClassifier Class:
Lanostane, Tirucallane and Euphane triterpenoids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD20637

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged