LAVENDUSTIN C

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H13NO5
Molecular Weight	275.2567
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC(NCC2=CC(O)=CC=C2O)=CC=C1O

InChI

InChIKey=LULATDWLDJOKCX-UHFFFAOYSA-N

InChI=1S/C14H13NO5/c16-10-2-4-12(17)8(5-10)7-15-9-1-3-13(18)11(6-9)14(19)20/h1-6,15-18H,7H2,(H,19,20)

HIDE SMILES / InChI

Molecular Formula	C14H13NO5
Molecular Weight	275.2567
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2614420 | https://www.ncbi.nlm.nih.gov/pubmed/8105084

Lavendustin C or HDBA (2-hyroxyl-5-(2,5-dihydroxybenzylamino) benzoic acid) is the active pharmacophore of lavendustin A, a tyrosine kinase inhibitor isolated from a butyl acetate extract of Streptomyces griseolavendus.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Epidermal growth factor receptor erbB1 58 Target ID: CHEMBL203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8105084	Inhibitor 8297	4.0 µM [IC50]
Tyrosine-protein kinase LCK 12 Target ID: CHEMBL258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8105084	Inhibitor 8297	10.0 µM [IC50]
Receptor protein-tyrosine kinase erbB-2 35 Target ID: CHEMBL1824 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8105084	Inhibitor 8297	0.9 µM [IC50]
CaM kinase II 1 Target ID: CHEMBL2097164 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1656271	Inhibitor 8297	0.2 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Isolation of a novel tyrosine kinase inhibitor, lavendustin A, from Streptomyces griseolavendus.	1989 Nov-Dec	2614420
Glycosphingolipid-enriched signaling domain in mouse neuroblastoma Neuro2a cells. Mechanism of ganglioside-dependent neuritogenesis.	1999 Jul 23	10409636
Ca2+ channel remodeling in perfused heart: Effects of mechanical work and interventions affecting Ca2+ cycling on sarcolemmal and sarcoplasmic reticulum Ca2+ channels.	2002 Dec	12397086
Modulation of β-catenin signaling by the inhibitors of MAP kinase, tyrosine kinase, and PI3-kinase pathways.	2013	24324366
Effects of the phytoestrogen, genistein, and protein tyrosine kinase inhibitor-dependent mechanisms on steroidogenesis and estrogen receptor expression in porcine granulosa cells of medium follicles.	2013 Jan	22920265

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Human neutrophils pretreated with lavendustin C (LVC) at concentrations between 10 and 150 microM or control neutrophils were stimulated by plasma-coated calcium pyrophosphate dihydrate (CPPD) or uncoated monosodium urate monohydrate (MSUM), and chemiluminescence, superoxide generation, intracellular calcium concentration, and degranulation (myeloperoxidase and lysozyme release) were monitored with time. LVC strongly inhibited chemiluminescence, superoxide anion generation, myeloperoxidase and lysozyme release, and calcium mobilization. After 1-min crystal-neutrophil incubations, neutrophil cytosolic fractions showed extensive inhibition of tyrosine kinase activity by LVC.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:36:08 GMT 2023` Edited by `admin` on `Sat Dec 16 08:36:08 GMT 2023`
Record UNII	HJM06BIW5M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAVENDUSTIN C

Common Name

English

NSC-666251

Code

English

5-(N-2,5-DIHYDROXYBENZYL)AMINOSALICYLIC ACID

Systematic Name

English

BENZOIC ACID, 5-(((2,5-DIHYDROXYPHENYL)METHYL)AMINO)-2-HYDROXY-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1967