Lup-20(30)-en-3beta-ol-29-al

ID: ALA2042333

Chembl Id: CHEMBL2042333

Cas Number: 64181-07-3

PubChem CID: 10071968

Max Phase: Preclinical

Molecular Formula: C30H48O2

Molecular Weight: 440.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C=O)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Standard InChI:  InChI=1S/C30H48O2/c1-19(18-31)20-10-13-27(4)16-17-29(6)21(25(20)27)8-9-23-28(5)14-12-24(32)26(2,3)22(28)11-15-30(23,29)7/h18,20-25,32H,1,8-17H2,2-7H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1

Standard InChI Key:  RYHMCEZDZZBPAQ-QGTGJCAVSA-N

Alternative Forms

1. Parent:

   

   ALA2042333

   30-Oxolupeol

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 440.71

Molecular Weight (Monoisotopic): 440.3654

AlogP: 7.20

#Rotatable Bonds: 2

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 6.48

CX LogD: 6.48

Aromatic Rings: 0

Heavy Atoms: 32

QED Weighted: 0.36

Np Likeness Score: 3.15

References

1. Gutiérrez-Nicolás F, Gordillo-Román B, Oberti JC, Estévez-Braun A, Ravelo AG, Joseph-Nathan P..  (2012)  Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD.,  75  (4): [PMID:22462772] [10.1021/np200910u]

2. Khan MF, Maurya CK, Dev K, Arha D, Rai AK, Tamrakar AK, Maurya R..  (2014)  Design and synthesis of lupeol analogues and their glucose uptake stimulatory effect in L6 skeletal muscle cells.,  24  (12): [PMID:24813738] [10.1016/j.bmcl.2014.04.059]

3. Bhandari P, Patel NK, Bhutani KK..  (2014)  Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors.,  24  (15): [PMID:24909081] [10.1016/j.bmcl.2014.05.032]

Source

Source(1):

• Scientific Literature