ID: ALA514105

Max Phase: Preclinical

Molecular Formula: C23H24O5

Molecular Weight: 380.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1c2c(c3oc4cc(=O)c(C)c5c-4c(c3c1O)O[C@H](C)[C@H]5C)O[C@H](C)[C@H]2C

Standard InChI:  InChI=1S/C23H24O5/c1-8-12(5)26-21-18-15(7-14(24)10(3)16(8)18)28-23-19(21)20(25)11(4)17-9(2)13(6)27-22(17)23/h7-9,12-13,25H,1-6H3/t8-,9-,12-,13-/m1/s1

Standard InChI Key:  WZDGQCYEIYZRBL-NRMKKVEVSA-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: 380.44

Molecular Weight (Monoisotopic): 380.1624

AlogP: 4.99

#Rotatable Bonds: 0

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: 6.68

CX Basic pKa: 2.07

CX LogP: 3.41

CX LogD: 2.63

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: 1.82

References

1. Lu ZY, Lin ZJ, Wang WL, Du L, Zhu TJ, Fang YC, Gu QQ, Zhu WM..  (2008)  Citrinin dimers from the halotolerant fungus Penicillium citrinum B-57.,  71  (4): [PMID:18281952] [10.1021/np0704708]

2. Du L, Liu HC, Fu W, Li DH, Pan QM, Zhu TJ, Geng MY, Gu QQ..  (2011)  Unprecedented citrinin trimer tricitinol B functions as a novel topoisomerase IIα inhibitor.,  54  (16): [PMID:21761866] [10.1021/jm200511x]

3. Meng LH, Liu Y, Li XM, Xu GM, Ji NY, Wang BG..  (2015)  Citrifelins A and B, Citrinin Adducts with a Tetracyclic Framework from Cocultures of Marine-Derived Isolates of Penicillium citrinum and Beauveria felina.,  78  (9): [PMID:26295595] [10.1021/acs.jnatprod.5b00450]

Source

Source(1):

• Scientific Literature