15-p-methoxylbenzylidene 14-deoxy-11,12-didehydroandrographolide

ID: ALA377520

Chembl Id: CHEMBL377520

PubChem CID: 11640963

Max Phase: Preclinical

Molecular Formula: C28H34O5

Molecular Weight: 450.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1/C=C/C1=C/C(=C/c2ccc(OC)cc2)OC1=O

Standard InChI:  InChI=1S/C28H34O5/c1-18-5-12-24-27(2,14-13-25(30)28(24,3)17-29)23(18)11-8-20-16-22(33-26(20)31)15-19-6-9-21(32-4)10-7-19/h6-11,15-16,23-25,29-30H,1,5,12-14,17H2,2-4H3/b11-8+,22-15-/t23-,24+,25-,27+,28+/m1/s1

Standard InChI Key:  ONVNKHISRSCEQH-HJVWSVJRSA-N

Alternative Forms

1. Parent:

   

   ALA377520

   14-Deoxy-11,12-didehydro-15-p-methoxylbenzylideneandrographolide

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: 450.58

Molecular Weight (Monoisotopic): 450.2406

AlogP: 4.82

#Rotatable Bonds: 5

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.50

Np Likeness Score: 2.43

References

1. Dai GF, Xu HW, Wang JF, Liu FW, Liu HM..  (2006)  Studies on the novel alpha-glucosidase inhibitory activity and structure-activity relationships for andrographolide analogues.,  16  (10): [PMID:16504503] [10.1016/j.bmcl.2006.02.011]

2. Xu HW, Dai GF, Liu GZ, Wang JF, Liu HM..  (2007)  Synthesis of andrographolide derivatives: a new family of alpha-glucosidase inhibitors.,  15  (12): [PMID:17428667] [10.1016/j.bmc.2007.03.063]

3. Wu ZW, Xu HW, Dai GF, Liu MJ, Zhu LP, Wu J, Wang YN, Wu FJ, Zhao D, Gao MF, Nie SS, Han W, Song JH, Liu HM..  (2013)  Improved inhibitory activities against tumor-cell migration and invasion by 15-benzylidene substitution derivatives of andrographolide.,  23  (23): [PMID:24120543] [10.1016/j.bmcl.2013.09.049]

Source

Source(1):

• Scientific Literature