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A2836

Sigma-Aldrich

Ansamitocin P-3 from Actinosynnema pretiosum

≥90% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C32H43ClN2O9
CAS Number:
66584-72-3
Molecular Weight:
635.14
MDL number:
MFCD00274586
UNSPSC Code:
12352202
PubChem Substance ID:
24890696
NACRES:
NA.32

Quality Level

200

Assay

≥90% (HPLC)

form

powder

storage temp.

2-8°C

SMILES string

CO[C@@H]1\C=C\C=C(C)\Cc2cc(OC)c(Cl)c(c2)N(C)C(=O)C[C@H](OC(=O)C(C)C)[C@]3(C)O[C@@H]3[C@H](C)[C@@H]4C[C@@]1(O)NC(=O)O4

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

InChI key

OPQNCARIZFLNLF-KUDLRRJMSA-N

Biochem/physiol Actions

Fungal metabolite with antineoplastic, antimitotic activity. Binds to tubulin and inhibits vinblastine-induced spiral formation.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Carl E Snipes et al.
Journal of natural products, 70(10), 1578-1581 (2007-09-26)
The ansacarbamitocins are a new family of maytansinoids that are unusually substituted with a glucose subunit and two carbamate functional groups and exhibit modest activity against some agricultural fungal disease organisms. Ansacarbamitocins A-F ( 1- 6) all consist of the
Daniel Ng et al.
Journal of industrial microbiology & biotechnology, 36(11), 1345-1351 (2009-07-18)
Constitutive overexpression of regulators in the ansamitocin biosynthetic cluster of Actinosynnema pretiosum was investigated as a strategy to increase the production of ansamitocin-P3 (AP-3), a clinically promising chemotherapeutic agent. Putative transcriptional regulators asm2, asm29, and asm34 as well as the
Highly active ansamitocin derivatives: mutasynthesis using an AHBA-blocked mutant.
Florian Taft et al.
Chembiochem : a European journal of chemical biology, 9(7), 1057-1060 (2008-04-03)
Juan Ma et al.
Archives of pharmacal research, 30(6), 670-673 (2007-08-08)
By using preparative TLC as the critical isolation procedure, two compounds, including one new amide N-glycosides of ansamitocin (2), were isolated from Actinosynnema pretiosum. The compounds were elucidated as N-demethyl-N-beta-D-glucopyranosyl ansamitocin P-2, named ansamitocinoside P-2 (1), and N-demethyl-N-beta-D-glucopyranosyl ansamitocin P-1
Peiji Zhao et al.
Chemistry & biology, 15(8), 863-874 (2008-08-30)
Ansamitocins are potent antitumor maytansinoids produced by Actinosynnema pretiosum. Their biosynthesis involves the initial assembly of a macrolactam polyketide, followed by a series of postpolyketide synthase (PKS) modifications. Three ansamitocin glycosides were isolated from A. pretiosum and fully characterized structurally
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