Ansamitocin P-3

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Names

[ CAS No. ]:
66584-72-3

[ Name ]:
Ansamitocin P-3

[Synonym ]:
Ansamitosin P 3
Propanoic acid, 2-methyl-, (1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10,12,1
 4(26),16,18-pentaen-6-yl ester
ANSAMITOCIN P-3
Tam-330
(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10(26),11,13,16,18-pentaen-6-yl 2- methylpropanoate
2'-De(acetylmethylamino)-2'-methylmaytansine
Propanoic acid, 2-methyl-, (1S,2R,3R,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10,12,1
 4(26),16,18-pentaen-6-yl ester
Anasamitocin P-3
(1S,2R,3R,5S,6S,16E,18E,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10(26),11,13,16,18-pentaen-6-yl 2- methylpropanoate
Maytansinol isobutyrate
O3-isobutyryl-maytansinol
(3E,5E,7R,84S)-14-chloro-10t,11c-epoxy-84-hydroxy-12c-isobutyryl-15,7r-dimethoxy-3,9c,11t,15-tetramethyl-(84r'H,86c'H)-15-aza-1(1,3)-benzena-8(4,6)-[1,3]oxazinana-cyclopentadecaphane-3,5-diene-82,14-dione

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
833.1±65.0 °C at 760 mmHg

[ Melting Point ]:
190-192℃

[ Molecular Formula ]:
C32H43ClN2O9

[ Molecular Weight ]:
635.145

[ Flash Point ]:
457.7±34.3 °C

[ Exact Mass ]:
634.265686

[ PSA ]:
136.16000

[ LogP ]:
5.09

[ Vapour Pressure ]:
0.0±3.2 mmHg at 25°C

[ Index of Refraction ]:
1.583

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OQ2291000
CHEMICAL NAME :
Maytansine, 2'-de(acetylmethylamino)-2'-methyl-
CAS REGISTRY NUMBER :
66584-72-3
LAST UPDATED :
199401
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C32-H43-Cl-N2-O9
MOLECULAR WEIGHT :
635.22

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
625 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - mouse Ascites tumor
DOSE/DURATION :
4 ug/kg
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 40,1707,1980

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H332-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
20/22-36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
OQ2293000

Synthetic Route

Precursor & DownStream

Precursor

  • 3-maytansinone 9-methyl ether
  • Maytansinol
  • (-)-maytansinol

DownStream

  • Maytansinol

Articles

Enhanced production of ansamitocin P-3 by addition of isobutanol in fermentation of Actinosynnema pretiosum.

Bioresour. Technol. 102 , 1863-1868, (2011)

Supply of isobutanol to enhance the production of anti-tumor agent ansamitocin P-3 (AP-3) in medium containing agro-industrial residues was investigated with analysis of gene transcription, enzyme act...

Amide N-glycosylation by Asm25, an N-glycosyltransferase of ansamitocins.

Chem. Biol. 15(8) , 863-74, (2008)

Ansamitocins are potent antitumor maytansinoids produced by Actinosynnema pretiosum. Their biosynthesis involves the initial assembly of a macrolactam polyketide, followed by a series of postpolyketid...

Determination of the cryptic stereochemistry of the first PKS chain-extension step in ansamitocin biosynthesis by Actinosynnema pretiosum.

ChemBioChem. 7(8) , 1221-5, (2006)

The biosynthesis of the antitumor antibiotic, ansamitocin, involves the assembly of a linear octaketide on the ansamitocin (asm) polyketide synthase (PKS), which is then cyclized to proansamitocin and...


More Articles


Related Compounds

  • Ansamitocin P-3
  • ANSAMITOCIN P-4
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  • 1-[p-[3-(Dimethylamino)propyl]phenethyl]-1-cyclohexanol
  • 1-[[p-(3-Piperidino-1-propynyl)phenyl]ethynyl]cyclohexanol
  • 4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
  • 1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
  • 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
  • 1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
  • (4-Methyl-tetrahydro-furan-2-yl)-methanol
  • Tert-butyl 4-hydroxy-2-methyl-2-phenylpyrrolidine-1-carboxylate
  • N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
  • (3',5'-Difluoro-[1,1'-biphenyl]-4-yl)methanamine
  • 4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
  • tert-Butyl-DL-alanine