ID: ALA1934583

Max Phase: Preclinical

Molecular Formula: C29H42O7

Molecular Weight: 502.65

Molecule Type: Small molecule

Representations

Canonical SMILES:  CO[C@H]1CC(=O)[C@]2(C)[C@H]3CC[C@]4(C)[C@@H]([C@H](C)[C@H]5CC(C)=C(CO)C(=O)O5)CC[C@H]4[C@@H]3C[C@H]3O[C@]32[C@H]1O

Standard InChI:  InChI=1S/C29H42O7/c1-14-10-21(35-26(33)17(14)13-30)15(2)18-6-7-19-16-11-24-29(36-24)25(32)22(34-5)12-23(31)28(29,4)20(16)8-9-27(18,19)3/h15-16,18-22,24-25,30,32H,6-13H2,1-5H3/t15-,16-,18+,19-,20-,21+,22-,24+,25-,27+,28-,29-/m0/s1

Standard InChI Key:  MKTMIPAPOLDOQT-QAYSIJLNSA-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: 502.65

Molecular Weight (Monoisotopic): 502.2931

AlogP: 3.20

#Rotatable Bonds: 4

Polar Surface Area: 105.59

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.92

CX Basic pKa:

CX LogP: 3.15

CX LogD: 3.15

Aromatic Rings: 0

Heavy Atoms: 36

QED Weighted: 0.45

Np Likeness Score: 3.57

References

1. Zhang H, Samadi AK, Gallagher RJ, Araya JJ, Tong X, Day VW, Cohen MS, Kindscher K, Gollapudi R, Timmermann BN..  (2011)  Cytotoxic withanolide constituents of Physalis longifolia.,  74  (12): [PMID:22098611] [10.1021/np200635r]

2. Yoneyama T, Arai MA, Sadhu SK, Ahmed F, Ishibashi M..  (2015)  Hedgehog inhibitors from Withania somnifera.,  25  (17): [PMID:26169123] [10.1016/j.bmcl.2015.06.081]

3. Chaudhary A, Kalra RS, Huang C, Prakash J, Kaul SC, Wadhwa R..  (2017)  2,3-Dihydro-3β-methoxy Withaferin-A Protects Normal Cells against Stress: Molecular Evidence of Its Potent Cytoprotective Activity.,  80  (10): [PMID:29043807] [10.1021/acs.jnatprod.7b00573]

4. Llanos GG, Araujo LM, Jiménez IA, Moujir LM, Rodríguez J, Jiménez C, Bazzocchi IL..  (2017)  Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.,  140  [PMID:28923386] [10.1016/j.ejmech.2017.09.004]

5. Tomita T, Wadhwa R, Kaul SC, Kurita R, Kojima N, Onishi Y..  (2021)  Withanolide Derivative 2,3-Dihydro-3β-methoxy Withaferin-A Modulates the Circadian Clock via Interaction with RAR-Related Orphan Receptor α (RORa).,  84  (7.0): [PMID:34152143] [10.1021/acs.jnatprod.0c01276]

Source

Source(1):

• Scientific Literature