2-Amino-4-hydroxy-4-(3-hydroxy-phenyl)-butyric acid

Names and Identifiers

Canonical SMILES: NC(CC(O)c1cccc(O)c1)C(=O)O

Standard InChI: InChI=1S/C10H13NO4/c11-8(10(14)15)5-9(13)6-2-1-3-7(12)4-6/h1-4,8-9,12-13H,5,11H2,(H,14,15)

Standard InChI Key: APPLEPDDBNLZPX-UHFFFAOYSA-N

Molfile:

     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
    6.9111   -5.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1994   -4.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4836   -5.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7677   -4.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9111   -5.8869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6270   -4.6494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7677   -3.8244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518   -5.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3401   -4.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6243   -5.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6243   -5.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3401   -6.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518   -5.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084   -4.6494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1994   -3.8244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  2  0
  1  6  1  0
  4  7  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
 10 14  1  0
  4  8  1  0
  2 15  1  0
M  END

Alternative Forms

Parent:

ALA120534
2-amino-4-hydroxy-4-(3-hydroxyphenyl)butanoic Acid

Associated Targets(Human)

KYNU Tchem Kynureninase (42 Activities)

Discover Target: KYNU

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Kynu Kynureninase (17 Activities)

Discover Target: Kynu

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 211.22	Molecular Weight (Monoisotopic): 211.0845	AlogP: 0.23	#Rotatable Bonds: 4
Polar Surface Area: 103.78	Molecular Species: ZWITTERION	HBA: 4	HBD: 4
#RO5 Violations: ┄	HBA (Lipinski): 5	HBD (Lipinski): 5	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 1.90	CX Basic pKa: 8.94	CX LogP: -2.35	CX LogD: -2.36
Aromatic Rings: 1	Heavy Atoms: 15	QED Weighted: 0.57	Np Likeness Score: 0.76

References

1. Walsh HA, Leslie PL, O'Shea KC, Botting NP.. (2002) 2-Amino-4-[3'-hydroxyphenyl]-4-hydroxybutanoic acid; a potent inhibitor of rat and recombinant human kynureninase., 12 (3): [PMID:11814797] [10.1016/s0960-894x(01)00758-2]
2. Lima S, Kumar S, Gawandi V, Momany C, Phillips RS.. (2009) Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity., 52 (2): [PMID:19143568] [10.1021/jm8010806]

Source

Source(1):

Scientific Literature