ID: ALA255890

Max Phase: Preclinical

Molecular Formula: C25H28O5

Molecular Weight: 408.49

Molecule Type: Small molecule

Representations

Synonyms (1): Abyssinone III
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)=CCc1cc([C@@H]2CC(=O)c3c(O)cc(O)cc3O2)cc(CC=C(C)C)c1O

Standard InChI:  InChI=1S/C25H28O5/c1-14(2)5-7-16-9-18(10-17(25(16)29)8-6-15(3)4)22-13-21(28)24-20(27)11-19(26)12-23(24)30-22/h5-6,9-12,22,26-27,29H,7-8,13H2,1-4H3/t22-/m0/s1

Standard InChI Key:  LQHKFMYWTKORCE-QFIPXVFZSA-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: 408.49

Molecular Weight (Monoisotopic): 408.1937

AlogP: 5.53

#Rotatable Bonds: 5

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.84

CX Basic pKa:

CX LogP: 6.29

CX LogD: 6.16

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: 1.90

References

1. Rukachaisirikul T, Innok P, Suksamrarn A..  (2008)  Erythrina alkaloids and a pterocarpan from the bark of Erythrina subumbrans.,  71  (1): [PMID:18171023] [10.1021/np070506w]

2. Na M, Jang J, Njamen D, Mbafor JT, Fomum ZT, Kim BY, Oh WK, Ahn JS..  (2006)  Protein tyrosine phosphatase-1B inhibitory activity of isoprenylated flavonoids isolated from Erythrina mildbraedii.,  69  (11): [PMID:17125223] [10.1021/np0601861]

3. Taniguchi M, Kubo I..  (1993)  Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.,  56  (9): [PMID:8254349] [10.1021/np50099a012]

4. Hegde VR, Dai P, Patel MG, Puar MS, Das P, Pai J, Bryant R, Cox PA.  (1997)  Phospholipase A 2 Inhibitors from an Erythrina Species from Samoa ,  60  (6): [10.1021/np960533e]

5. Wätjen W, Suckow-Schnitker AK, Rohrig R, Kulawik A, Addae-Kyereme J, Wright CW, Passreiter CM..  (2008)  Prenylated flavonoid derivatives from the bark of Erythrina addisoniae.,  71  (4): [PMID:18302333] [10.1021/np070417j]

6. Farmer RL, Biddle MM, Nibbs AE, Huang X, Bergan RC, Scheidt KA..  (2010)  Concise syntheses of the abyssinones and discovery of new inhibitors of prostate cancer and MMP-2 expression.,  1  (8): [PMID:21116437] [10.1021/ml100110x]

7. Nguyen PH, Dao TT, Kim J, Phong do T, Ndinteh DT, Mbafor JT, Oh WK..  (2011)  New 5-deoxyflavonoids and their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) activity.,  19  (11): [PMID:21571537] [10.1016/j.bmc.2011.04.037]

8. Nyandoro SS, Munissi JJ, Kombo M, Mgina CA, Pan F, Gruhonjic A, Fitzpatrick P, Lu Y, Wang B, Rissanen K, Erdélyi M..  (2017)  Flavonoids from Erythrina schliebenii.,  80  (2): [PMID:28112509] [10.1021/acs.jnatprod.6b00839]

Source

Source(1):

• Scientific Literature