ANSAMITOMICIN P-3

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H43ClN2O9
Molecular Weight	635.145
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@](O)(NC(=O)O1)[C@H](OC)\C=C\C=C(C)\CC3=CC(OC)=C(Cl)C(=C3)N(C)C(=O)C[C@H](OC(=O)C(C)C)[C@]4(C)O[C@H]4[C@@H]2C

InChI

InChIKey=OPQNCARIZFLNLF-JBHFWYGFSA-N

InChI=1S/C32H43ClN2O9/c1-17(2)29(37)43-25-15-26(36)35(6)21-13-20(14-22(40-7)27(21)33)12-18(3)10-9-11-24(41-8)32(39)16-23(42-30(38)34-32)19(4)28-31(25,5)44-28/h9-11,13-14,17,19,23-25,28,39H,12,15-16H2,1-8H3,(H,34,38)/b11-9+,18-10+/t19-,23+,24-,25+,28+,31+,32+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C32H43ClN2O9
Molecular Weight	635.145
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21043240 | https://www.ncbi.nlm.nih.gov/pubmed/24124473 | https://www.ncbi.nlm.nih.gov/pubmed/593392

Ansamitocin P3, a structural analogue of maytansine, was isolated from Nocardia. Structurally maytansine and ansamitocin P3 are polyketide macrolactams differing in the acyl groups at the C3 position. Ansamitocin P-3 inhibited the polymerization of tubulin and depolymerized the once polymerized tubulin. Ansamitocin P3 exerts antitumour properties.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin 69 Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21043240	Inhibitor 8297		1.3 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1517150 https://www.ncbi.nlm.nih.gov/pubmed/24906866 https://www.ncbi.nlm.nih.gov/pubmed/24124473 https://www.ncbi.nlm.nih.gov/pubmed/593392	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antitubulin activities of ansamitocins and maytansinoids.	1981 Sep 1	21043240

Patents

Sample Use Guides

In Vivo Use Guide

mice: 10 ug (LD50 30-50 ug)

Route of Administration: Intravenous

In Vitro Use Guide

Ansamitocin P3 potently inhibited the proliferation of MCF-7, HeLa, EMT-6/AR1 and MDA-MB-231 cells in culture with a half-maximal inhibitory concentration of 20±3, 50±0.5, 140±17, and 150±1.1 pM, respectively.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:34:15 UTC 2023` Edited by `admin` on `Fri Dec 15 17:34:15 UTC 2023`
Record UNII	7SUK7876BG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANSAMITOMICIN P-3

Common Name

English

ANSAMITOCIN P 3

Common Name

English

ANSAMITOSIN P 3

Common Name

English

MAYTANSINE, 2'-DE(ACETYLMETHYLAMINO)-2'-METHYL-

Systematic Name

English

MAYTANSINOL ISOBUTYRATE

Common Name

English

ANTIBIOTIC C 15003P3

Code

English

NSC-292222

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C67477