ID: ALA465858

Max Phase: Preclinical

Molecular Formula: C13H14O6

Molecular Weight: 266.25

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  Cc1c(O)c(C(=O)O)c(O)c2c1[C@H](C)[C@@H](C)OC2=O

Standard InChI:  InChI=1S/C13H14O6/c1-4-6(3)19-13(18)8-7(4)5(2)10(14)9(11(8)15)12(16)17/h4,6,14-15H,1-3H3,(H,16,17)/t4-,6-/m1/s1

Standard InChI Key:  VVVMDYGNIVXIIG-INEUFUBQSA-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: 266.25

Molecular Weight (Monoisotopic): 266.0790

AlogP: 1.77

#Rotatable Bonds: 1

Polar Surface Area: 104.06

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.40

CX Basic pKa:

CX LogP: 4.11

CX LogD: 0.58

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.67

Np Likeness Score: 2.03

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