(4aS,6aS,6bR,8aR,9S,10S,12aR,12bR,14bS)-9-formyl-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

ID: ALA2386825

Chembl Id: CHEMBL2386825

Cas Number: 639-14-5

PubChem CID: 92825

Max Phase: Preclinical

Molecular Formula: C30H46O4

Molecular Weight: 470.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(C=O)[C@@H]5CC[C@]43C)[C@@H]2C1

Standard InChI:  InChI=1S/C30H46O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,18,20-23,32H,8-17H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1

Standard InChI Key:  QMHCWDVPABYZMC-MYPRUECHSA-N

Alternative Forms

1. Parent:

   

   ALA2386825

   Gypsogenin

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: 470.69

Molecular Weight (Monoisotopic): 470.3396

AlogP: 6.41

#Rotatable Bonds: 2

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.74

CX Basic pKa: ┄

CX LogP: 5.63

CX LogD: 3.03

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: 3.41

References

1. Yu F, Wang Q, Zhang Z, Peng Y, Qiu Y, Shi Y, Zheng Y, Xiao S, Wang H, Huang X, Zhu L, Chen K, Zhao C, Zhang C, Yu M, Sun D, Zhang L, Zhou D..  (2013)  Development of oleanane-type triterpenes as a new class of HCV entry inhibitors.,  56  (11): [PMID:23662817] [10.1021/jm301910a]

2. Emirdağ-Öztürk S, Karayıldırım T, Çapcı-Karagöz A, Alankuş-Çalışkan Ö, Özmen A, Poyrazoğlu-Çoban E..  (2014)  Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.,  82  [PMID:24941130] [10.1016/j.ejmech.2014.05.084]

3. Vo NNQ, Nomura Y, Muranaka T, Fukushima EO..  (2019)  Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.,  82  (12): [PMID:31774676] [10.1021/acs.jnatprod.9b00538]

4. Anderson, Orlagh, Beckett, Joseph, Briggs, Carla C., Natrass, Liam A., Cranston, Charles F., Wilkinson, Elizabeth J., Owen, Jack H., Mir Williams, Rhodri, Loukaidis, Angelos, Bouillon, Marc E., Pritchard, Deiniol, Lahmann, Martina, Baird, Mark S., Denny, Paul W..  (2020)  An investigation of the antileishmanial properties of semi-synthetic saponins,  11  (7): [PMID:33479679] [10.1039/d0md00123f]

Source

Source(1):

• Scientific Literature