americanin A

ID: ALA482240

Chembl Id: CHEMBL482240

PubChem CID: 44575382

Max Phase: Preclinical

Molecular Formula: C18H16O6

Molecular Weight: 328.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C/C=C/c1ccc2c(c1)O[C@@H](CO)[C@H](c1ccc(O)c(O)c1)O2

Standard InChI:  InChI=1S/C18H16O6/c19-7-1-2-11-3-6-15-16(8-11)23-17(10-20)18(24-15)12-4-5-13(21)14(22)9-12/h1-9,17-18,20-22H,10H2/b2-1+/t17-,18-/m0/s1

Standard InChI Key:  NTXXGPYGMQQSML-QLJMBOKNSA-N

Alternative Forms

1. Parent:

   

   ALA482240

   AMERICANIN A

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: 328.32

Molecular Weight (Monoisotopic): 328.0947

AlogP: 2.18

#Rotatable Bonds: 4

Polar Surface Area: 96.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.21

CX Basic pKa: ┄

CX LogP: 2.04

CX LogD: 2.03

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.45

Np Likeness Score: 2.00

References

1. Su BN, Pawlus AD, Jung HA, Keller WJ, McLaughlin JL, Kinghorn AD..  (2005)  Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity.,  68  (4): [PMID:15844957] [10.1021/np0495985]

2. Lee MA, Kim WK, Park HJ, Kang SS, Lee SK..  (2013)  Anti-proliferative activity of hydnocarpin, a natural lignan, is associated with the suppression of Wnt/β-catenin signaling pathway in colon cancer cells.,  23  (20): [PMID:24018191] [10.1016/j.bmcl.2013.08.065]

3. Nguyen PH, Yang JL, Uddin MN, Park SL, Lim SI, Jung DW, Williams DR, Oh WK..  (2013)  Protein tyrosine phosphatase 1B (PTP1B) inhibitors from Morinda citrifolia (Noni) and their insulin mimetic activity.,  76  (11): [PMID:24224843] [10.1021/np400533h]

4. Jung C, Hong JY, Bae SY, Kang SS, Park HJ, Lee SK..  (2015)  Antitumor Activity of Americanin A Isolated from the Seeds of Phytolacca americana by Regulating the ATM/ATR Signaling Pathway and the Skp2-p27 Axis in Human Colon Cancer Cells.,  78  (12): [PMID:26595875] [10.1021/acs.jnatprod.5b00743]

Source

Source(1):

• Scientific Literature