ID: ALA558103

Max Phase: Preclinical

Molecular Formula: C20H20O4

Molecular Weight: 324.38

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  CC(C)=CCc1cc([C@@H]2CC(=O)c3ccc(O)cc3O2)ccc1O

Standard InChI:  InChI=1S/C20H20O4/c1-12(2)3-4-13-9-14(5-8-17(13)22)19-11-18(23)16-7-6-15(21)10-20(16)24-19/h3,5-10,19,21-22H,4,11H2,1-2H3/t19-/m0/s1

Standard InChI Key:  NLTOTZSPOYWSSP-IBGZPJMESA-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: 324.38

Molecular Weight (Monoisotopic): 324.1362

AlogP: 4.31

#Rotatable Bonds: 3

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.78

CX Basic pKa:

CX LogP: 4.22

CX LogD: 4.07

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.83

Np Likeness Score: 1.98

References

1. Maiti A, Cuendet M, Croy VL, Endringer DC, Pezzuto JM, Cushman M..  (2007)  Synthesis and biological evaluation of (+/-)-abyssinone II and its analogues as aromatase inhibitors for chemoprevention of breast cancer.,  50  (12): [PMID:17511439] [10.1021/jm070109i]

2. 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]

3. Mori-Hongo M, Yamaguchi H, Warashina T, Miyase T..  (2009)  Melanin synthesis inhibitors from Lespedeza cyrtobotrya.,  72  (1): [PMID:19102656] [10.1021/np800535g]

4. 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]

5. 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]

6. Li W, Li S, Higai K, Sasaki T, Asada Y, Ohshima S, Koike K..  (2013)  Evaluation of licorice flavonoids as protein tyrosine phosphatase 1B inhibitors.,  23  (21): [PMID:24047800] [10.1016/j.bmcl.2013.08.102]

7. Lin Y, Kuang Y, Li K, Wang S, Song W, Qiao X, Sabir G, Ye M..  (2017)  Screening for bioactive natural products from a 67-compound library of Glycyrrhiza inflata.,  25  (14): [PMID:28522265] [10.1016/j.bmc.2017.05.009]

8. Lin Y, Kuang Y, Li K, Wang S, Ji S, Chen K, Song W, Qiao X, Ye M..  (2017)  Nrf2 activators from Glycyrrhiza inflata and their hepatoprotective activities against CCl4-induced liver injury in mice.,  25  (20): [PMID:28835349] [10.1016/j.bmc.2017.08.018]

9. Li K, Ji S, Song W, Kuang Y, Lin Y, Tang S, Cui Z, Qiao X, Yu S, Ye M..  (2017)  Glycybridins A-K, Bioactive Phenolic Compounds from Glycyrrhiza glabra.,  80  (2): [PMID:28140583] [10.1021/acs.jnatprod.6b00783]

Source

Source(1):

• Scientific Literature