ID: ALA465552

Max Phase: Preclinical

Molecular Formula: C23H22O7

Molecular Weight: 410.42

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  C=C(CO)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(OC)c(OC)cc4[C@@H]2C3=O)O1

Standard InChI:  InChI=1S/C23H22O7/c1-11(9-24)16-7-14-15(29-16)5-4-12-22(25)21-13-6-18(26-2)19(27-3)8-17(13)28-10-20(21)30-23(12)14/h4-6,8,16,20-21,24H,1,7,9-10H2,2-3H3/t16-,20-,21+/m1/s1

Standard InChI Key:  ZJMLELXRQUXRIU-HBGVWJBISA-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: 410.42

Molecular Weight (Monoisotopic): 410.1366

AlogP: 2.68

#Rotatable Bonds: 4

Polar Surface Area: 83.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.95

CX Basic pKa:

CX LogP: 2.04

CX LogD: 2.04

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.78

Np Likeness Score: 1.95

References

1. Chin YW, Mdee LK, Mbwambo ZH, Mi Q, Chai HB, Cragg GM, Swanson SM, Kinghorn AD..  (2006)  Prenylated flavonoids from the root bark of Berchemia discolor, a Tanzanian medicinal plant.,  69  (11): [PMID:17125241] [10.1021/np060418w]

2. Konoshima T, Terada H, Kokumai M, Kozuka M, Tokuda H, Estes JR, Li L, Wang HK, Lee KH..  (1993)  Studies on inhibitors of skin tumor promotion, XII. Rotenoids from Amorpha fruticosa.,  56  (6): [PMID:8350086] [10.1021/np50096a006]

3. Li L, Wang HK, Chang JJ, McPhail AT, McPhail DR, Terada H, Konoshima T, Kokumai M, Kozuka M, Estes JR..  (1993)  Antitumor agents, 138. Rotenoids and isoflavones as cytotoxic constitutents from Amorpha fruticosa.,  56  (5): [PMID:8326318] [10.1021/np50095a005]

4. Russell DA, Bridges HR, Serreli R, Kidd SL, Mateu N, Osberger TJ, Sore HF, Hirst J, Spring DR..  (2020)  Hydroxylated Rotenoids Selectively Inhibit the Proliferation of Prostate Cancer Cells.,  83  (6): [PMID:32459967] [10.1021/acs.jnatprod.9b01224]

Source

Source(1):

• Scientific Literature