ID: ALA470650

Max Phase: Preclinical

Molecular Formula: C16H14O5

Molecular Weight: 286.28

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  COc1cc(C)c2c(=O)c3c(O)cc(OC)cc3oc2c1

Standard InChI:  InChI=1S/C16H14O5/c1-8-4-9(19-2)6-12-14(8)16(18)15-11(17)5-10(20-3)7-13(15)21-12/h4-7,17H,1-3H3

Standard InChI Key:  QDLAGTHXVHQKRE-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: 286.28

Molecular Weight (Monoisotopic): 286.0841

AlogP: 2.98

#Rotatable Bonds: 2

Polar Surface Area: 68.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.34

CX Basic pKa:

CX LogP: 3.50

CX LogD: 3.46

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: 0.88

References

1. Rojas IS, Lotina-Hennsen B, Mata R..  (2000)  Effect of lichen metabolites on thylakoid electron transport and photophosphorylation in isolated spinach chloroplasts.,  63  (10): [PMID:11076561] [10.1021/np0001326]

2. Pettit GR, Zhang Q, Pinilla V, Herald DL, Doubek DL, Duke JA..  (2004)  Isolation and structure of gustastatin from the Brazilian nut tree Gustavia hexapetala.,  67  (6): [PMID:15217278] [10.1021/np030509i]

3. Pettit GR, Meng Y, Herald DL, Graham KA, Pettit RK, Doubek DL..  (2003)  Isolation and structure of ruprechstyril from Ruprechtia tangarana.,  66  (8): [PMID:12932125] [10.1021/np0300986]

4. Gachet MS, Kunert O, Kaiser M, Brun R, Zehl M, Keller W, Muñoz RA, Bauer R, Schuehly W..  (2011)  Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense.,  74  (4): [PMID:21438586] [10.1021/np100415m]

5. Goel M, Dureja P, Rani A, Uniyal PL, Laatsch H..  (2011)  Isolation, characterization and antifungal activity of major constituents of the Himalayan lichen Parmelia reticulata Tayl.,  59  (6): [PMID:21351753] [10.1021/jf1049613]

6. Kishore N, Kumar P, Shanker K, Verma AK..  (2019)  Human disorders associated with inflammation and the evolving role of natural products to overcome.,  179  [PMID:31255927] [10.1016/j.ejmech.2019.06.034]

7. Zeng HT, Yu YH, Zeng X, Li MM, Li X, Xu SS, Tu ZC, Yuan T..  (2022)  Anti-inflammatory Dimeric Benzophenones from an Endophytic Pleosporales Species.,  85  (1.0): [PMID:35007071] [10.1021/acs.jnatprod.1c00900]

Source

Source(1):

• Scientific Literature