ID: ALA1208903

Max Phase: Preclinical

Molecular Formula: C32H22O10

Molecular Weight: 566.52

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  COc1ccc(-c2cc(=O)c3c(O)cc(O)c(-c4cc(-c5cc(=O)c6c(O)cc(O)cc6o5)ccc4OC)c3o2)cc1

Standard InChI:  InChI=1S/C32H22O10/c1-39-18-6-3-15(4-7-18)26-14-24(38)31-22(36)12-21(35)29(32(31)42-26)19-9-16(5-8-25(19)40-2)27-13-23(37)30-20(34)10-17(33)11-28(30)41-27/h3-14,33-36H,1-2H3

Standard InChI Key:  HUOOMAOYXQFIDQ-UHFFFAOYSA-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: 566.52

Molecular Weight (Monoisotopic): 566.1213

AlogP: 5.74

#Rotatable Bonds: 5

Polar Surface Area: 159.80

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.09

CX Basic pKa:

CX LogP: 5.38

CX LogD: 3.26

Aromatic Rings: 6

Heavy Atoms: 42

QED Weighted: 0.20

Np Likeness Score: 1.01

References

1. Sasaki H, Miki K, Kinoshita K, Koyama K, Juliawaty LD, Achmad SA, Hakim EH, Kaneda M, Takahashi K..  (2010)  beta-Secretase (BACE-1) inhibitory effect of biflavonoids.,  20  (15): [PMID:20598535] [10.1016/j.bmcl.2010.06.021]

2. PubChem BioAssay data set, 

3. Wong IL, Chan KF, Chan TH, Chow LM..  (2012)  Flavonoid dimers as novel, potent antileishmanial agents.,  55  (20): [PMID:22989363] [10.1021/jm301172v]

4. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

5. Sasaki H, Kitoh Y, Tsukada M, Miki K, Koyama K, Juliawaty LD, Hakim EH, Takahashi K, Kinoshita K..  (2015)  Inhibitory activities of biflavonoids against amyloid-β peptide 42 cytotoxicity in PC-12 cells.,  25  (14): [PMID:26004578] [10.1016/j.bmcl.2015.04.106]

6. Sirimangkalakitti N, Juliawaty LD, Hakim EH, Waliana I, Saito N, Koyama K, Kinoshita K..  (2019)  Naturally occurring biflavonoids with amyloid β aggregation inhibitory activity for development of anti-Alzheimer agents.,  29  (15): [PMID:31138471] [10.1016/j.bmcl.2019.05.020]

7. Letribot B, Nascimento M, Cerrato G, Darrigrand R, Salgues V, Renko D, Pruvost A, Alami M, Messaoudi S, Apcher S..  (2022)  Biological Investigation of a Water-Soluble Isoginkgetin-Phosphate Analogue, Targeting the Spliceosome with In Vivo Antitumor Activity.,  65  (6.0): [PMID:35235336] [10.1021/acs.jmedchem.1c01654]

8. Zhang S, Sun Y, Yao F, Li H, Yang Y, Li X, Bai Z, Hu Y, Wang P, Xu X..  (2023)  Ginkgo Biflavones Cause p53 Wild-Type Dependent Cell Death in a Transcription-Independent Manner of p53.,  86  (2.0): [PMID:36700552] [10.1021/acs.jnatprod.2c00959]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays