ID: ALA590522

Max Phase: Preclinical

Molecular Formula: C22H23NO2

Molecular Weight: 333.43

Molecule Type: Small molecule

Representations

Synonyms (1): Mahanine
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)=CCC[C@H]1C=Cc2c(c(C)cc3c2[nH]c2cc(O)ccc23)O1

Standard InChI:  InChI=1S/C22H23NO2/c1-13(2)5-4-6-16-8-10-18-21-19(11-14(3)22(18)25-16)17-9-7-15(24)12-20(17)23-21/h5,7-12,16,23-24H,4,6H2,1-3H3/t16-/m0/s1

Standard InChI Key:  UKLOEFBVUZOVRX-INIZCTEOSA-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: 333.43

Molecular Weight (Monoisotopic): 333.1729

AlogP: 5.86

#Rotatable Bonds: 3

Polar Surface Area: 45.25

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.77

CX Basic pKa:

CX LogP: 5.66

CX LogD: 5.66

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: 2.33

References

1. Sheikh KD, Banerjee PP, Jagadeesh S, Grindrod SC, Zhang L, Paige M, Brown ML..  (2010)  Fluorescent epigenetic small molecule induces expression of the tumor suppressor ras-association domain family 1A and inhibits human prostate xenograft.,  53  (6): [PMID:20184324] [10.1021/jm9011615]

2. Samanta SK, Dutta D, Roy S, Bhattacharya K, Sarkar S, Dasgupta AK, Pal BC, Mandal C, Mandal C..  (2013)  Mahanine, a DNA minor groove binding agent exerts cellular cytotoxicity with involvement of C-7-OH and -NH functional groups.,  56  (14): [PMID:23829449] [10.1021/jm400290q]

Source

Source(1):

• Scientific Literature