ID: ALA1224808

Max Phase: Preclinical

Molecular Formula: C16H12O5

Molecular Weight: 284.27

Molecule Type: Small molecule

Representations

Synonyms (2): Austrocortinin | Austrocortirubin
Synonyms from Alternative Forms(2):

Canonical SMILES:  COc1cc(O)c2c(c1O)C(=O)c1cc(C)ccc1C2=O

Standard InChI:  InChI=1S/C16H12O5/c1-7-3-4-8-9(5-7)15(19)13-12(14(8)18)10(17)6-11(21-2)16(13)20/h3-6,17,20H,1-2H3

Standard InChI Key:  IVJVOKCJFGMBTB-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: 284.27

Molecular Weight (Monoisotopic): 284.0685

AlogP: 2.19

#Rotatable Bonds: 1

Polar Surface Area: 83.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.64

CX Basic pKa:

CX LogP: 3.97

CX LogD: 3.94

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.67

Np Likeness Score: 1.00

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. Choomuenwai V, Andrews KT, Davis RA..  (2012)  Synthesis and antimalarial evaluation of a screening library based on a tetrahydroanthraquinone natural product scaffold.,  20  (24): [PMID:23117170] [10.1016/j.bmc.2012.09.052]

4. Wang Y, Islam MA, Davis RA, McAlpine SR..  (2015)  The fungal natural product (1S,3S)-austrocortirubin induces DNA damage in HCT116 cells via a mechanism unique from other DNA damaging agents.,  25  (2): [PMID:25499433] [10.1016/j.bmcl.2014.11.055]

5. 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