3-Hydroxy-9beta,13alpha-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic amide,N-ethyl

ID: ALA3928971

Chembl Id: CHEMBL3928971

PubChem CID: 46184627

Max Phase: Preclinical

Molecular Formula: C31H43NO3

Molecular Weight: 477.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)[C@]1(C)CC[C@]2(C)CC[C@]3(C)C4=CC=C5C(=CC(=O)C(O)=C5C)[C@]4(C)CC[C@@]3(C)[C@@H]2C1

Standard InChI:  InChI=1S/C31H43NO3/c1-8-32-26(35)28(4)12-11-27(3)13-15-30(6)23-10-9-20-19(2)25(34)22(33)17-21(20)29(23,5)14-16-31(30,7)24(27)18-28/h9-10,17,24,34H,8,11-16,18H2,1-7H3,(H,32,35)/t24-,27-,28-,29+,30-,31+/m1/s1

Standard InChI Key:  YGLDJGRHKCVIQN-ZRCCSVPJSA-N

Alternative Forms

1. Parent:

   

   ALA3928971

   (2R,4aS,6aR,6aS,14aS,14bR)-N-ethyl-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxamide

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: 477.69

Molecular Weight (Monoisotopic): 477.3243

AlogP: 6.75

#Rotatable Bonds: 2

Polar Surface Area: 66.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.75

CX Basic pKa: ┄

CX LogP: 5.10

CX LogD: 5.10

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.46

Np Likeness Score: 2.76

References

1. Jiang F, Wang HJ, Bao QC, Wang L, Jin YH, Zhang Q, Jiang D, You QD, Xu XL..  (2016)  Optimization and biological evaluation of celastrol derivatives as Hsp90-Cdc37 interaction disruptors with improved druglike properties.,  24  (21): [PMID:27647369] [10.1016/j.bmc.2016.08.070]

2. 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]

3. He QW,Feng JH,Hu XL,Long H,Huang XF,Jiang ZZ,Zhang XQ,Ye WC,Wang H.  (2020)  Synthesis and Biological Evaluation of Celastrol Derivatives as Potential Immunosuppressive Agents.,  83  (9.0): [PMID:32822186] [10.1021/acs.jnatprod.0c00067]

Source

Source(1):

• Scientific Literature