ID: ALA1224809

Max Phase: Preclinical

Molecular Formula: C16H16O6

Molecular Weight: 304.30

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC1=CC(=O)c2c(cc3c(c2O)C[C@@H](O)[C@@](C)(O)C3)C1=O

Standard InChI:  InChI=1S/C16H16O6/c1-16(21)6-7-3-9-13(15(20)8(7)4-12(16)18)10(17)5-11(22-2)14(9)19/h3,5,12,18,20-21H,4,6H2,1-2H3/t12-,16+/m1/s1

Standard InChI Key:  QNFWEYHUDXOXHJ-WBMJQRKESA-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: 304.30

Molecular Weight (Monoisotopic): 304.0947

AlogP: 0.51

#Rotatable Bonds: 1

Polar Surface Area: 104.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.38

CX Basic pKa:

CX LogP: 0.71

CX LogD: 0.66

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.70

Np Likeness Score: 2.77

References

1. Trisuwan K, Khamthong N, Rukachaisirikul V, Phongpaichit S, Preedanon S, Sakayaroj J..  (2010)  Anthraquinone, cyclopentanone, and naphthoquinone derivatives from the sea fan-derived fungi Fusarium spp. PSU-F14 and PSU-F135.,  73  (9): [PMID:20815366] [10.1021/np100282k]

2. Yang KL, Wei MY, Shao CL, Fu XM, Guo ZY, Xu RF, Zheng CJ, She ZG, Lin YC, Wang CY..  (2012)  Antibacterial anthraquinone derivatives from a sea anemone-derived fungus Nigrospora sp.,  75  (5): [PMID:22545792] [10.1021/np300103w]

3. Klein-Júnior LC, Corrêa R, Vander Heyden Y, Cechinel Filho V..  (2019)  All that glitters is not gold: Panning cytotoxic natural products and derivatives with a fused tricyclic backbone by the estimation of their leadlikeness for cancer treatment.,  166  [PMID:30684866] [10.1016/j.ejmech.2019.01.028]

4. Hou XM, Wang CY, Gerwick WH, Shao CL..  (2019)  Marine natural products as potential anti-tubercular agents.,  165  [PMID:30685527] [10.1016/j.ejmech.2019.01.026]

Source

Source(1):

• Scientific Literature