(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-benzyl 10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

ID: ALA445301

Chembl Id: CHEMBL445301

Cas Number: 303114-51-4

PubChem CID: 11753144

Max Phase: Preclinical

Molecular Formula: C37H54O3

Molecular Weight: 546.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC[C@]2(C(=O)OCc3ccccc3)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Standard InChI:  InChI=1S/C37H54O3/c1-32(2)19-21-37(31(39)40-24-25-11-9-8-10-12-25)22-20-35(6)26(27(37)23-32)13-14-29-34(5)17-16-30(38)33(3,4)28(34)15-18-36(29,35)7/h8-13,27-30,38H,14-24H2,1-7H3/t27-,28-,29+,30-,34-,35+,36+,37-/m0/s1

Standard InChI Key:  BXPBVHNXTDZAAM-GBVPUKILSA-N

Alternative Forms

1. Parent:

   

   ALA445301

   Benzyl oleanolate

Molecule Features

Natural Product: No

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: 546.84

Molecular Weight (Monoisotopic): 546.4073

AlogP: 8.89

#Rotatable Bonds: 3

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 8.47

CX LogD: 8.47

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.30

Np Likeness Score: 2.59

References

1. Zhang YN, Zhang W, Hong D, Shi L, Shen Q, Li JY, Li J, Hu LH..  (2008)  Oleanolic acid and its derivatives: new inhibitor of protein tyrosine phosphatase 1B with cellular activities.,  16  (18): [PMID:18707891] [10.1016/j.bmc.2008.07.080]

2. Joshi P, Tanwar O, Rambhade S, Bhaisare M, Jain D.  (2012)  2-D QSAR studies of steroidal natural products oleanic acid and their semisynthetic derivatives as potent protein tyrosine phosphatase 1B inhibitors,  21  (3): [10.1007/s00044-010-9529-5]

3. Siewert B, Wiemann J, Köwitsch A, Csuk R..  (2014)  The chemical and biological potential of C ring modified triterpenoids.,  72  [PMID:24361521] [10.1016/j.ejmech.2013.11.025]

4. Parra A, Martin-Fonseca S, Rivas F, Reyes-Zurita FJ, Medina-O'Donnell M, Martinez A, Garcia-Granados A, Lupiañez JA, Albericio F..  (2014)  Semi-synthesis of acylated triterpenes from olive-oil industry wastes for the development of anticancer and anti-HIV agents.,  74  [PMID:24480359] [10.1016/j.ejmech.2013.12.049]

5. Ramírez-Espinosa JJ, Rios MY, Paoli P, Flores-Morales V, Camici G, de la Rosa-Lugo V, Hidalgo-Figueroa S, Navarrete-Vázquez G, Estrada-Soto S..  (2014)  Synthesis of oleanolic acid derivatives: In vitro, in vivo and in silico studies for PTP-1B inhibition.,  87  [PMID:25264584] [10.1016/j.ejmech.2014.09.036]

6. Medina-O'Donnell M, Rivas F, Reyes-Zurita FJ, Martinez A, Martin-Fonseca S, Garcia-Granados A, Ferrer-Martín RM, Lupiañez JA, Parra A..  (2016)  Semi-synthesis and antiproliferative evaluation of PEGylated pentacyclic triterpenes.,  118  [PMID:27128174] [10.1016/j.ejmech.2016.04.016]

7. Wang WW, Xu SH, Zhao YZ, Zhang C, Zhang YY, Yu BY, Zhang J..  (2017)  Microbial hydroxylation and glycosylation of pentacyclic triterpenes as inhibitors on tissue factor procoagulant activity.,  27  (4): [PMID:28109788] [10.1016/j.bmcl.2016.12.066]

8. Medina-O'Donnell M, Vega-Granados K, Martinez A, Sepúlveda MR, Molina-Bolívar JA, Álvarez de Cienfuegos L, Parra A, Reyes-Zurita FJ, Rivas F..  (2023)  Synthesis, Optical Properties, and Antiproliferative Evaluation of NBD-Triterpene Fluorescent Probes.,  86  (1.0): [PMID:36542806] [10.1021/acs.jnatprod.2c00880]

Source

Source(1):

• Scientific Literature