ID: ALA29660

Max Phase: Preclinical

Molecular Formula: C22H18O12

Molecular Weight: 474.37

Molecule Type: Small molecule

Representations

Synonyms (2): chicoric acid | D-chicoric acid
Synonyms from Alternative Forms(2):

Canonical SMILES:  O=C(/C=C/c1ccc(O)c(O)c1)O[C@H](C(=O)O)[C@H](OC(=O)/C=C/c1ccc(O)c(O)c1)C(=O)O

Standard InChI:  InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m0/s1

Standard InChI Key:  YDDGKXBLOXEEMN-QFZCZCNSSA-N

Molecule Features

Natural Product: No

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: 474.37

Molecular Weight (Monoisotopic): 474.0798

AlogP: 1.23

#Rotatable Bonds: 9

Polar Surface Area: 208.12

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.72

CX Basic pKa:

CX LogP: 3.02

CX LogD: -3.15

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.17

Np Likeness Score: 0.71

References

1. Lin Z, Neamati N, Zhao H, Kiryu Y, Turpin JA, Aberham C, Strebel K, Kohn K, Witvrouw M, Pannecouque C, Debyser Z, De Clercq E, Rice WG, Pommier Y, Burke TR..  (1999)  Chicoric acid analogues as HIV-1 integrase inhibitors.,  42  (8): [PMID:10212126] [10.1021/jm980531m]

2. King PJ, Ma G, Miao W, Jia Q, McDougall BR, Reinecke MG, Cornell C, Kuan J, Kim TR, Robinson WE..  (1999)  Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication.,  42  (3): [PMID:9986720] [10.1021/jm9804735]

3. Queffélec C, Bailly F, Mbemba G, Mouscadet JF, Debyser Z, Witvrouw M, Cotelle P..  (2008)  The total synthesis of fukiic acid, an HIV-1 integrase inhibitor.,  43  (10): [PMID:18243421] [10.1016/j.ejmech.2007.12.013]

4. Burgess EJ, Larsen L, Perry NB..  (2000)  A cytotoxic sesquiterpene caffeate from the liverwort Bazzanianovae-zelandiae.,  63  (4): [PMID:10785435] [10.1021/np990492x]

5. Silhár P, Lardy MA, Hixon MS, Shoemaker CB, Barbieri JT, Struss AK, Lively JM, Javor S, Janda KD..  (2013)  The C-terminus of Botulinum A Protease Has Profound and Unanticipated Kinetic Consequences Upon the Catalytic Cleft.,  4  (2): [PMID:23565325] [10.1021/ml300428s]

6. Zhao Y, Gu Q, Morris-Natschke SL, Chen CH, Lee KH..  (2016)  Incorporation of Privileged Structures into Bevirimat Can Improve Activity against Wild-Type and Bevirimat-Resistant HIV-1.,  59  (19): [PMID:27676157] [10.1021/acs.jmedchem.6b00461]

7. Zhou Y, McGillick BE, Teng YG, Haranahalli K, Ojima I, Swaminathan S, Rizzo RC..  (2016)  Identification of small molecule inhibitors of botulinum neurotoxin serotype E via footprint similarity.,  24  (20): [PMID:27543389] [10.1016/j.bmc.2016.07.031]

Source

Source(1):

• Scientific Literature