NANAFROCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H14O6
Molecular Weight	302.2788
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1O[C@@H](CC(O)=O)CC2=C1C(=O)C3=C(C=CC=C3O)C2=O

InChI

InChIKey=ZCJHPTKRISJQTN-JGVFFNPUSA-N

InChI=1S/C16H14O6/c1-7-13-10(5-8(22-7)6-12(18)19)15(20)9-3-2-4-11(17)14(9)16(13)21/h2-4,7-8,17H,5-6H2,1H3,(H,18,19)/t7-,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H14O6
Molecular Weight	302.2788
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/67008638 | https://www.ncbi.nlm.nih.gov/pubmed/20833755

Nanafrocin (nanaomycin A) belongs to the class of quinone antibiotics isolated from a strain OS-3966 of Streptomyces rosa var. notoensis. Nanafrocin (nanaomycin A) mode of action is dependent on its reduction by the respiratory chain-linked NADH or flavin dehydrogenase of the organism. The reduced form of nanafrocin (nanaomycin A) is quickly auto-oxidized by molecular oxygen producing singlet molecular oxygen (O2−). The ability to produce O2− is related to the antimicrobial activity of nanafrocin (nanaomycin A).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA (cytosine-5)-methyltransferase 3B 1 Target ID: CHEMBL6095 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20833755	Inhibitor 8297		500.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Nanaomycins, new antibiotics produced by a strain of Streptomyces. III. A new component, nanaomycin C, and biological activities of nanaomycin derivatives.	1975 Dec	1206004
The mode of action of nanaomycin A in Gram-positive bacteria.	1980 Aug	6159343
Biosynthesis of nanaomycin: syntheses of nanaomycin E from nanaomycin A and of nanaomycin B from nanaomycin E in a cell-free system.	1981 Jul	7287685
Nanaomycin A selectively inhibits DNMT3B and reactivates silenced tumor suppressor genes in human cancer cells.	2010 Nov	20833755

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The growth of Staphylococcus aureus FDA 209P and Bacillus cereus T was strongly inhibited by 1.56 and 6.25 ug/ml, respectively, of nanaomycin A. Nanaomycin A (1.56 ug/ml) inhibited RNA and DNA biosyntheses in Staphylococcus aureus at 5 minutes of incubation. It also inhibited protein biosynthesis at the same concentration of the drug, but the biosynthesis continued for 20 minutes. The incorporation of [3H]Dpm into cell-wall of Bacillus cereus was severely inhibited by 3.12 ug/ml of nanaomycin A.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:37:50 GMT 2023` Edited by `admin` on `Fri Dec 15 15:37:50 GMT 2023`
Record UNII	8XBV72641V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NANAFROCIN

Official Name

English

(1S,3R)-3,4,5,10-TETRAHYDRO-9-HYDROXY-1-METHYL-5,10-DIOXO-1H-NAPHTHO-(2,3-C)PYRAN-3-ACETIC ACID

Systematic Name

English

NANAFROCIN [JAN]

Common Name

English

nanafrocin [INN]

Common Name

English

NSC-267461

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C258