Details of the Drug

General Information of Drug (ID: DMH3X06)

Drug Name

LAVENDUSTIN A

Synonyms

Lavendustin A; 125697-92-9; RG14355; UNII-3Y0G32G2RV; CHEMBL103552; 3Y0G32G2RV; C21H19NO6; Lavendustin A, from Streptomyces griseolavendus; Benzoic acid,5-[[(2,5-dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino]-2-hydroxy-; RG 14355; 5-(((2,5-Dihydroxyphenyl)methyl)((2-hydroxyphenyl)methyl)amino)-2-hydroxybenzoic acid; Benzoic acid, 5-(((2,5-dihydroxyphenyl)methyl)((2-hydroxyphenyl)methyl)amino)-2-hydroxy-; 5-Amino-((N-2,5-dihydroxybenzyl)-N -2-hydroxybenzyl)salicylic acid

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

381.4

Topological Polar Surface Area (xlogp)

3.7

Rotatable Bond Count (rotbonds)

6

Hydrogen Bond Donor Count (hbonddonor)

5

Hydrogen Bond Acceptor Count (hbondacc)

7

Chemical Identifiers

Formula: C21H19NO6
IUPAC Name: 5-[(2,5-dihydroxyphenyl)methyl-[(2-hydroxyphenyl)methyl]amino]-2-hydroxybenzoic acid
Canonical SMILES: C1=CC=C(C(=C1)CN(CC2=C(C=CC(=C2)O)O)C3=CC(=C(C=C3)O)C(=O)O)O
InChI: InChI=1S/C21H19NO6/c23-16-6-8-19(25)14(9-16)12-22(11-13-3-1-2-4-18(13)24)15-5-7-20(26)17(10-15)21(27)28/h1-10,23-26H,11-12H2,(H,27,28)
InChIKey: ULTTYPMRMMDONC-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 3894
ChEBI ID: CHEBI:92413
CAS Number: 125697-92-9
TTD ID: D0D9TU

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Epidermal growth factor receptor (EGFR)	TTGKNB4	EGFR_HUMAN	Inhibitor	[1]
LCK tyrosine protein kinase (LCK)	TT860QF	LCK_HUMAN	Inhibitor	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Epidermal growth factor receptor (EGFR)	DTT	EGFR	5.84E-05	0.32	0.55

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Novel antiproliferative agents derived from lavendustin A. J Med Chem. 1994 Nov 25;37(24):4079-84.
2	Non-amine based analogues of lavendustin A as protein-tyrosine kinase inhibitors. J Med Chem. 1993 Oct 1;36(20):3010-4.
3	A comparison of physicochemical property profiles of marketed oral drugs and orally bioavailable anti-cancer protein kinase inhibitors in clinical development. Curr Top Med Chem. 2007;7(14):1408-22.
4	National Cancer Institute Drug Dictionary (drug id 596693).
5	The selectivity of protein kinase inhibitors: a further update. Biochem J. 2007 Dec 15;408(3):297-315.
6	Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem J. 2000 Oct 1;351(Pt 1):95-105.
7	Optimization of protein kinase CK2 inhibitors derived from 4,5,6,7-tetrabromobenzimidazole. J Med Chem. 2004 Dec 2;47(25):6239-47.
8	The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
9	Discovery of a (1H-benzoimidazol-2-yl)-1H-pyridin-2-one (BMS-536924) inhibitor of insulin-like growth factor I receptor kinase with in vivo antitum... J Med Chem. 2005 Sep 8;48(18):5639-43.
10	Nasopharyngeal carcinoma: Current treatment options and future directions. J Nasopharyng Carcinoma, 2014, 1(16): e16.
11	Triple negative breast cancer--current status and prospective targeted treatment based on HER1 (EGFR), TOP2A and C-MYC gene assessment. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2009 Mar;153(1):13-7.
12	Gefitinib ('Iressa', ZD1839) and new epidermal growth factor receptor inhibitors. Br J Cancer. 2004 Feb 9;90(3):566-72.
13	Quantitative prediction of fold resistance for inhibitors of EGFR. Biochemistry. 2009 Sep 8;48(35):8435-48.
14	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 1797).
15	Boehringer Ingelheim. Product Development Pipeline. June 2 2009.
16	Synthesis and Src kinase inhibitory activity of a series of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-furyl-3-quinolinecarbonitriles. J Med Chem. 2006 Dec 28;49(26):7868-76.
17	Clinical pipeline report, company report or official report of GlaxoSmithKline (2009).