aleuritolic acid

ID: ALA258249

Chembl Id: CHEMBL258249

Cas Number: 26549-17-7

PubChem CID: 161527

Max Phase: Preclinical

Molecular Formula: C30H48O3

Molecular Weight: 456.71

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Aleuritolic Acid | Maprounic Acid | Maprounic acid|Aleuritolic acid|26549-17-7|CHEBI:73107|3beta-Hydroxyurs-12-en-29-oic acid|(4aS,6aR,6bR,8aR,10S,12aR,14aS,14bS)-10-hydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,3,4,5,6a,7,8,8a,10,11,12,13,14,14b-tetradecahydropicene-4a-carboxylic acid|3-Hydroxyurs-12-en-29-oic acid|SCHEMBL438408|CHEMBL258249|BDBM50478515|LMPR0106180013|NSC 359426|Urs-12-en-29-oic acid, 3-hydroxy-, (3beta)-|Q27140309|(4aS,6bR,8aR,10S,12aR,12bR,14aS,14bS)-10-hydroxy-2,2,6b,9,9,12a,14aShow More⌵

Canonical SMILES:  CC1(C)CC[C@]2(C(=O)O)CC=C3[C@]4(C)CC[C@H]5C(C)(C)[C@@H](O)CC[C@]5(C)[C@H]4CC[C@@]3(C)[C@@H]2C1

Standard InChI:  InChI=1S/C30H48O3/c1-25(2)16-17-30(24(32)33)15-10-21-28(6)12-8-19-26(3,4)23(31)11-14-27(19,5)20(28)9-13-29(21,7)22(30)18-25/h10,19-20,22-23,31H,8-9,11-18H2,1-7H3,(H,32,33)/t19-,20+,22-,23-,27-,28+,29+,30+/m0/s1

Standard InChI Key:  BHHPRAFMEFGOLZ-QVUWEPBXSA-N

Alternative Forms

1. Parent:

   

   ALA258249

   ALEURITOLIC ACID

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: 456.71

Molecular Weight (Monoisotopic): 456.3603

AlogP: 7.23

#Rotatable Bonds: 1

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.74

CX Basic pKa: ┄

CX LogP: 6.59

CX LogD: 3.99

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.41

Np Likeness Score: 2.93

References

1. Pattamadilok D, Suttisri R..  (2008)  Seco-terpenoids and other constituents from Elateriospermum tapos.,  71  (2): [PMID:18179177] [10.1021/np070629g]

2. Pengsuparp T, Cai L, Fong HH, Kinghorn AD, Pezzuto JM, Wani MC, Wall ME..  (1994)  Pentacyclic triterpenes derived from Maprounea africana are potent inhibitors of HIV-1 reverse transcriptase.,  57  (3): [PMID:7515410] [10.1021/np50105a017]

3. Yu MS, Lee J, Lee JM, Kim Y, Chin YW, Jee JG, Keum YS, Jeong YJ..  (2012)  Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.,  22  (12): [PMID:22578462] [10.1016/j.bmcl.2012.04.081]

4. Kim HJ, Fei X, Cho SC, Choi BY, Ahn HC, Lee K, Seo SY, Keum YS..  (2015)  Discovery of α-mangostin as a novel competitive inhibitor against mutant isocitrate dehydrogenase-1.,  25  (23): [PMID:26508549] [10.1016/j.bmcl.2015.10.034]

5. Zhang GJ, Pan QM, Zhang YL, Liao HB, Yang YQ, Hou Y, Liang D..  (2018)  Coumarinolignoids and Taraxerane Triterpenoids from Sapium discolor and Their Inhibitory Potential on Microglial Nitric Oxide Production.,  81  (10): [PMID:30350995] [10.1021/acs.jnatprod.8b00585]

6. Saquib M, Ansari MI, Johnson CR, Khatoon S, Kamil Hussain M, Coop A..  (2019)  Recent advances in the targeting of human DNA ligase I as a potential new strategy for cancer treatment.,  182  [PMID:31499361] [10.1016/j.ejmech.2019.111657]

Source

Source(1):

• Scientific Literature