LEPTOMYCIN B

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C33H48O6
Molecular Weight	540.7306
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	5
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(\C=C\[C@@H]1OC(=O)C=C[C@@H]1C)=C\[C@H](C)C\C=C\C(C)=C\[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C\C(C)=C\C(O)=O

InChI

InChIKey=YACHGFWEQXFSBS-XYERBDPFSA-N

InChI=1S/C33H48O6/c1-9-28(14-15-29-24(5)13-16-31(36)39-29)19-22(3)12-10-11-21(2)17-25(6)32(37)27(8)33(38)26(7)18-23(4)20-30(34)35/h10-11,13-17,19-20,22,24-27,29,33,38H,9,12,18H2,1-8H3,(H,34,35)/b11-10+,15-14+,21-17+,23-20+,28-19-/t22-,24+,25-,26+,27-,29+,33-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C33H48O6
Molecular Weight	540.7306
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	5
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9190288 | https://www.ncbi.nlm.nih.gov/pubmed/28412356 |https://www.ncbi.nlm.nih.gov/pubmed/18784437 | https://www.ncbi.nlm.nih.gov/pubmed/28942004

Leptomycin B (LMB) an antibiotic originally isolated from Streptomyces, is a specific inhibitor of CRM1 (exportin 1), an evolutionarily conserved receptor for the nuclear export signal of proteins. It binds covalently to cysteine 528 in the nuclear export signal binding region of CRM1 leading to the inhibition of protein nuclear export. It was shown, that LMB possessed the ability to augment the effect of the tumor suppressor p53 in esophageal squamous cancer cell lines and thus LMB could be a promising component in p53 gene therapy. Recently was conducted experiments, which revealed, that LMB at a very low concentration (0.5 nM) combined with gefitinib have shown synergistic therapeutic effects and have ameliorated the development of gefitinib-induced resistance in lung cancer cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Exportin-1 7 Target ID: O14980 Gene ID: 7514.0 Gene Symbol: XPO1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28412356	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
1'S-1'-acetoxychavicol acetate isolated from Alpinia galanga inhibits human immunodeficiency virus type 1 replication by blocking Rev transport.	2006-07	16760408
Application of the synthetic aminosugars for glycodiversification: synthesis and antimicrobial studies of pyranmycin.	2004-03-05	14987005
A synthetic HIV-1 Rev inhibitor interfering with the CRM1-mediated nuclear export.	2002-10-29	12374846
Leptomycin B inhibition of signal-mediated nuclear export by direct binding to CRM1.	1998-08-01	9683540
Leptomycin B is an inhibitor of nuclear export: inhibition of nucleo-cytoplasmic translocation of the human immunodeficiency virus type 1 (HIV-1) Rev protein and Rev-dependent mRNA.	1997-02	9190288

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:03:33 GMT 2025` Edited by `admin` on `Mon Mar 31 19:03:33 GMT 2025`
Record UNII	Y031I2N1EO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEPTOMYCIN B

Common Name

English

CI-940

Preferred Name

English

PD-114720

Code

English

(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-19-((2S,3S)-3,6-DIHYDRO-3-METHYL-6-OXO-2H-PYRAN-2-YL)-17-ETHYL-6-HYDROXY-3,5,7,9,11,15-HEXAMETHYL-8-OXO-2,10,12,16,18-NONADECAPENTAENOIC ACID

Common Name

English

LEPTOMYCIN B [MI]

Common Name

English

ELACTOCIN

Common Name

English

CL-1957A

Code

English

NSC-364372

Code

English

Code System Code Type Description

MESH

C038753