dihydrocelastrol

ID: ALA1092797

Chembl Id: CHEMBL1092797

Cas Number: 193957-88-9

PubChem CID: 10411574

Max Phase: Preclinical

Molecular Formula: C29H40O4

Molecular Weight: 452.64

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dihydrocelastrol | dihydrocelastrol|Triptohypol C|193957-88-9|(2R,4aS,6aS,12bS,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid|CHEMBL1092797|SCHEMBL18850315|CHEBI:132340|DTXSID801346962|BDBM50481949|193957-88-9 (dihydrocelastrol)|AKOS040748253|HY-117469|CS-0066075|(2R,4aS,6aS,6aS,14aS,14bR)-10,11-dihydroxy-2,4a,6a,6a,9,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1H-picene-2-carboxylic acid|rac-(2R,4aS,6aS,6aS,1Show More⌵

Canonical SMILES:  Cc1c(O)c(O)cc2c1CC=C1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@](C)(C(=O)O)CC[C@]3(C)CC[C@]12C

Standard InChI:  InChI=1S/C29H40O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h8,15,22,30-31H,7,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1

Standard InChI Key:  WZAUFGYINZYCKH-JJWQIEBTSA-N

Alternative Forms

1. Parent:

   

   ALA1092797

   DIHYDROCELASTROL

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: 452.64

Molecular Weight (Monoisotopic): 452.2927

AlogP: 6.64

#Rotatable Bonds: 1

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: 6.90

CX LogD: 4.29

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 2.93

References

1. Ryu YB, Park SJ, Kim YM, Lee JY, Seo WD, Chang JS, Park KH, Rho MC, Lee WS..  (2010)  SARS-CoV 3CLpro inhibitory effects of quinone-methide triterpenes from Tripterygium regelii.,  20  (6): [PMID:20167482] [10.1016/j.bmcl.2010.01.152]

2. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

3. Figueiredo SAC, Salvador JAR, Cortés R, Cascante M..  (2017)  Design, synthesis and biological evaluation of novel C-29 carbamate celastrol derivatives as potent and selective cytotoxic compounds.,  139  [PMID:28865279] [10.1016/j.ejmech.2017.08.058]

4. Figueiredo SAC, Salvador JAR, Cortés R, Cascante M..  (2017)  Novel celastrol derivatives with improved selectivity and enhanced antitumour activity: Design, synthesis and biological evaluation.,  138  [PMID:28688281] [10.1016/j.ejmech.2017.06.029]

5. Kyriakou E, Schmidt S, Dodd GT, Pfuhlmann K, Simonds SE, Lenhart D, Geerlof A, Schriever SC, De Angelis M, Schramm KW, Plettenburg O, Cowley MA, Tiganis T, Tschöp MH, Pfluger PT, Sattler M, Messias AC..  (2018)  Celastrol Promotes Weight Loss in Diet-Induced Obesity by Inhibiting the Protein Tyrosine Phosphatases PTP1B and TCPTP in the Hypothalamus.,  61  (24): [PMID:30525586] [10.1021/acs.jmedchem.8b01224]

6. Stevens M, Abdeen S, Salim N, Ray AM, Washburn A, Chitre S, Sivinski J, Park Y, Hoang QQ, Chapman E, Johnson SM..  (2019)  HSP60/10 chaperonin systems are inhibited by a variety of approved drugs, natural products, and known bioactive molecules.,  29  (9): [PMID:30852084] [10.1016/j.bmcl.2019.02.028]

7. Chen Z, Zhang D, Yan S, Hu C, Huang Z, Li Z, Peng S, Li X, Zhu Y, Yu H, Lian B, Kang Q, Li M, Zeng Z, Zhang XK, Su Y..  (2019)  SAR study of celastrol analogs targeting Nur77-mediated inflammatory pathway.,  177  [PMID:31132532] [10.1016/j.ejmech.2019.05.009]

Source

Source(1):

• Scientific Literature