ID: ALA510139

Max Phase: Preclinical

Molecular Formula: C13H14O5

Molecular Weight: 250.25

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  CC1=C2C(=CO[C@H](C)[C@H]2C)C(O)=C(C(=O)O)C1=O

Standard InChI:  InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1

Standard InChI Key:  CQIUKKVOEOPUDV-IYSWYEEDSA-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: 250.25

Molecular Weight (Monoisotopic): 250.0841

AlogP: 1.72

#Rotatable Bonds: 1

Polar Surface Area: 83.83

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.42

CX Basic pKa:

CX LogP: 0.81

CX LogD: -3.84

Aromatic Rings: 0

Heavy Atoms: 18

QED Weighted: 0.69

Np Likeness Score: 2.16

References

1. Bryant FO, Cutler HG, Parker SR, Jacyno JM.  (1994)  Effect of Fungal Natural Products in an Agrobacterium tumefaciens Potato Disc Assay,  57  (5): [10.1021/np50107a012]

2. Nakajima S, Nozawa K.  (1979)  Isolation in High Yield of Citrinin From Penicillium odoratum and of Mycophenolic Acid From Penicillium brunneo-stoloniferum,  42  (4): [10.1021/np50004a012]

3. 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]

4. Macías M, Ulloa M, Gamboa A, Mata R..  (2000)  Phytotoxic compounds from the new coprophilous fungus guanomyces polythrix.,  63  (6): [PMID:10869195] [10.1021/np990534h]

5. PubChem BioAssay data set, 

6. Kouznetsova VL, Tsigelny IF, Nagle MA, Nigam SK..  (2011)  Elucidation of common pharmacophores from analysis of targeted metabolites transported by the multispecific drug transporter-Organic anion transporter1 (Oat1).,  19  (11): [PMID:21571536] [10.1016/j.bmc.2011.04.045]

7. 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]

8. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

9. PubChem BioAssay data set, 

10. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H..  (2001)  Characterization of ochratoxin A transport by human organic anion transporters.,  69  (1): [PMID:11669456] [10.1016/s0024-3205(01)01296-6]

11. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H..  (2002)  Role of human organic anion transporter 4 in the transport of ochratoxin A.,  1590  (1): [PMID:12063169] [10.1016/s0167-4889(02)00187-8]

12. Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H..  (1999)  Transport of ochratoxin A by renal multispecific organic anion transporter 1.,  289  (1): [PMID:10336520]

13. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

14. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

15. Stevens M, Abdeen S, Salim N, Ray AM, Washburn A, Chitre S, Sivinski J, Park Y, Hoang QQ, Chapman E, Johnson SM..  (2019)  HSP60/10 chaperonin systems are inhibited by a variety of approved drugs, natural products, and known bioactive molecules.,  29  (9): [PMID:30852084] [10.1016/j.bmcl.2019.02.028]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• DrugMatrix
• TP-search Transporter Database