NOCARDAMIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H48N6O9
Molecular Weight	600.7048
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ON1CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC1=O

InChI

InChIKey=NHKCCADZVLTPPO-UHFFFAOYSA-N

InChI=1S/C27H48N6O9/c34-22-10-14-26(38)32(41)20-8-3-6-18-30-24(36)12-15-27(39)33(42)21-9-2-5-17-29-23(35)11-13-25(37)31(40)19-7-1-4-16-28-22/h40-42H,1-21H2,(H,28,34)(H,29,35)(H,30,36)

HIDE SMILES / InChI

Molecular Formula	C27H48N6O9
Molecular Weight	600.7048
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/21376551 | DOI: 10.1007/s11746-998-0200-y | https://www.ncbi.nlm.nih.gov/pubmed/7054147

Nocardamine is a cyclic trihydroxamate. It belongs to a group of microbial siderophores which form complexes with iron and aluminum ions. Nocardamine was described first as an antibiotic active against mycobacteria and proteus. It is produced by Nocardia species, several Streptomyces species, Chromobacterium and Pseudomonas. Nocardamine exhibited significant antioxidant effects. It is suggested that it should be applied in food and biological model systems. In vitro nocardamine showed antitumor activity – it has inhibitory effects to colony formation of tumor cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxidative Stress 162 Target ID: WP408 Sources: DOI: 10.1007/s11746-998-0200-y	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21376551	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Genome sequence of Kitasatospora setae NBRC 14216T: an evolutionary snapshot of the family Streptomycetaceae.	2010-12	21059706
Desferrioxamine E produced by Streptomyces griseus stimulates growth and development of Streptomyces tanashiensis.	2005-09	16151202
Cyclic peptides of the nocardamine class from a marine-derived bacterium of the genus Streptomyces.	2005-04	15844966
Identification of a cluster of genes that directs desferrioxamine biosynthesis in Streptomyces coelicolor M145.	2004-12-22	15600304

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

T-47D, SK-Mel-5, SK-Mel-28, RPMI-7951 cancer cells. The cells were treated with nocardamine at 5, 10, 20 and 40 uM in soft agar matrix and incubated at 37 ◦C in a 5% CO2 incubator for 3 weeks. Results indicated that nocardamine inhibited colony formation of T-47D, SK-Mel-5, SK-Mel-28, and RPMI-7951 cancer cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:22:13 GMT 2025` Edited by `admin` on `Mon Mar 31 21:22:13 GMT 2025`
Record UNII	Q645668975
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NOCARDAMIN

Common Name

English

DEFERRIFERRIOXAMINE E

Preferred Name

English

1,12,23-TRIHYDROXY-1,6,12,17,23,28-HEXAAZACYCLOTRITRIACONTANE-2,5,13,16,24,27-HEXONE

Systematic Name

English

PROFERRIOXAMINE E

Common Name

English

NOCARDAMIN [MI]

Common Name

English

NOCARDAMINE

Common Name

English

DEFERRIOXAMINE E

Common Name

English

DESFERRIOXAMINE E

Common Name

English

Code System Code Type Description

CHEBI

50437