ID: ALA523622

Max Phase: Preclinical

Molecular Formula: C30H48O4

Molecular Weight: 472.71

Molecule Type: Small molecule

Representations

Synonyms (1): 23-Hydroxyursolic Acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@H]1[C@H](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)(CO)[C@@H]5CC[C@]43C)[C@H]12

Standard InChI:  InChI=1S/C30H48O4/c1-18-9-14-30(25(33)34)16-15-28(5)20(24(30)19(18)2)7-8-22-26(3)12-11-23(32)27(4,17-31)21(26)10-13-29(22,28)6/h7,18-19,21-24,31-32H,8-17H2,1-6H3,(H,33,34)/t18-,19+,21-,22-,23+,24+,26+,27+,28-,29-,30+/m1/s1

Standard InChI Key:  NZCULBURCGAPSF-PQWKYGPVSA-N

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

Properties

Molecular Weight: 472.71

Molecular Weight (Monoisotopic): 472.3553

AlogP: 6.06

#Rotatable Bonds: 2

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.74

CX Basic pKa:

CX LogP: 5.30

CX LogD: 2.70

Aromatic Rings: 0

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: 3.13

References

1. Jew SS, Yoo CH, Lim DY, Kim H, Mook-Jung I, Jung MW, Choi H, Jung YH, Kim H, Park HG..  (2000)  Structure-activity relationship study of asiatic acid derivatives against beta amyloid (A beta)-induced neurotoxicity.,  10  (2): [PMID:10673093] [10.1016/s0960-894x(99)00658-7]

2. Nishimura K, Fukuda T, Miyase T, Noguchi H, Chen XM..  (1999)  Activity-guided isolation of triterpenoid acyl CoA cholesteryl acyl transferase (ACAT) inhibitors from Ilex kudincha.,  62  (7): [PMID:10425145] [10.1021/np990019j]

3. Tapondjou LA, Lontsi D, Sondengam BL, Shaheen F, Choudhary MI, Atta-ur-Rahman, van Heerden FR, Park HJ, Lee KT..  (2003)  Saponins from Cussonia bancoensis and their inhibitory effects on nitric oxide production.,  66  (9): [PMID:14510614] [10.1021/np020412g]

4. Yang H, Jeong EJ, Kim J, Sung SH, Kim YC..  (2011)  Antiproliferative triterpenes from the leaves and twigs of Juglans sinensis on HSC-T6 cells.,  74  (4): [PMID:21309591] [10.1021/np1008202]

5. Choi YH, Zhou W, Oh J, Choe S, Kim DW, Lee SH, Na M..  (2012)  Rhododendric acid A, a new ursane-type PTP1B inhibitor from the endangered plant Rhododendron brachycarpum G. Don.,  22  (19): [PMID:22940448] [10.1016/j.bmcl.2012.08.029]

6. Wen Q, Lu Y, Chao Z, Chen DF..  (2017)  Anticomplement triterpenoids from the roots of Ilex asprella.,  27  (4): [PMID:28094185] [10.1016/j.bmcl.2017.01.007]

7. Wubshet SG, Tahtah Y, Heskes AM, Kongstad KT, Pateraki I, Hamberger B, Møller BL, Staerk D..  (2016)  Identification of PTP1B and α-Glucosidase Inhibitory Serrulatanes from Eremophila spp. by Combined use of Dual High-Resolution PTP1B and α-Glucosidase Inhibition Profiling and HPLC-HRMS-SPE-NMR.,  79  (4): [PMID:26960032] [10.1021/acs.jnatprod.5b01128]

8. Cao YG, Zhang YL, Zeng MN, Qi M, Ren YJ, Liu YL, Zhao X, Zheng XK, Feng WS..  (2020)  Renoprotective Mono- and Triterpenoids from the Fruit of Gardenia jasminoides.,  83  (4): [PMID:32141747] [10.1021/acs.jnatprod.9b01119]

9. Xu GB, Xiao YH, Zhang QY, Zhou M, Liao SG..  (2018)  Hepatoprotective natural triterpenoids.,  145  [PMID:29353722] [10.1016/j.ejmech.2018.01.011]

Source

Source(1):

• Scientific Literature