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 62 Target ID: CHEMBL203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8105084	Inhibitor 8504	4.0 µM [IC50]
Tyrosine-protein kinase LCK 14 Target ID: CHEMBL258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8105084	Inhibitor 8504	10.0 µM [IC50]
Receptor protein-tyrosine kinase erbB-2 35 Target ID: CHEMBL1824 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8105084	Inhibitor 8504	0.9 µM [IC50]
CaM kinase II 2 Target ID: CHEMBL2097164 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1656271	Inhibitor 8504	0.2 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
The Effects of Phytoestrogen Genistein on Steroidogenesis and Estrogen Receptor Expression in Porcine Granulosa Cells of Large Follicles.	2015	26255463
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.	2013-01	22920265
Modulation of β-catenin signaling by the inhibitors of MAP kinase, tyrosine kinase, and PI3-kinase pathways.	2013	24324366
Involvement of CaM kinase II in the impairment of endothelial function and eNOS activity in aortas of Type 2 diabetic rats.	2012-09	22494112
Augmentation of insulin-stimulated ANP release through tyrosine kinase and PI 3-kinase in diabetic rats.	2006-11	16828931
[Construction of a three-dimensional human angiogenesis model in vitro for antiangiogenic drug selection].	2004-10	15485791
Ca2+ channel remodeling in perfused heart: Effects of mechanical work and interventions affecting Ca2+ cycling on sarcolemmal and sarcoplasmic reticulum Ca2+ channels.	2002-12	12397086
Calcium/calmodulin-dependent protein kinase II phosphorylates and regulates the Drosophila eag potassium channel.	2002-07-05	11980904
Endotoxin increases intercellular resistance in microvascular endothelial cells by a tyrosine kinase pathway.	2000-10	10942525
Glycosphingolipid-enriched signaling domain in mouse neuroblastoma Neuro2a cells. Mechanism of ganglioside-dependent neuritogenesis.	1999-07-23	10409636
Isolation of a novel tyrosine kinase inhibitor, lavendustin A, from Streptomyces griseolavendus.	1989-11-01	2614420

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 `Mon Mar 31 22:11:55 GMT 2025` Edited by `admin` on `Mon Mar 31 22:11:55 GMT 2025`
Record UNII	HJM06BIW5M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-666251

Preferred Name

English

LAVENDUSTIN C

Common Name

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