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Ansamitocin P 3

HCID 443593
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Basic information

CAS
66584-72-3
Standard SMILES
COc1cc2cc(c1Cl)N(C)C(=O)C[C@H](OC(=O)C(C)C)[C@]1(C)O[C@H]1[C@H](C)[C@@H]1C[C@@](O)(NC(=O)O1)[C@H](OC)C=CC=C(C)C2
InChIKey
OPQNCARIZFLNLF-OWOYPUEESA-N
Molecular formula
C32H43ClN2O9
Average molar mass
635.1 g/mol
Monoisotopic mass
634.2657086

Names & identifiers

Preferred name
Ansamitocin P 3
IUPAC
[(1S,2R,3S,5S,6S,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-methylpropanoate
English name
ansamitocin P-3
Molecular formula
C32H43ClN2O9
Molecular weight
635.14

Names & synonyms

66584-72-3Ansamitocin P 3DTXSID801316919Maytansine, 2'-de(acetylmethylamino)-2'-methyl-RefChem:915928DTXCID901776326680-663-6Ansamitocin P-3(14S,16S,32S,33S,2R,4S,10E,12E,14R)-86-chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl isobutyrateNCGC00014650-03NCGC00014650-07Maytansinol isobutyrate
Show more names
Tam-330Tam 330Nsc292222MTA/CBR32Ansamitosin P 3Anasamitocin P-3US-DMF No.: 034434Ansamitocin p-3 90%

Database identifiers

CAS

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
136 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
9
Rotatable bonds
5
Heavy atoms
44
Formal charge
0
Complexity
1,150

Physicochemical properties

Melting point
190 · 190-192℃
Boiling point
833.1 · 833.1±65.0 °C(Predicted)
Density
1.29 · 1.29
storage temp.
-20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility
100 mg/mL · DMSO: 100 mg/mL (157.45 mM);Ethanol: 55 mg/mL (86.60 mM)
pka
9.82 · 9.82±0.70(Predicted)
form
Solid
color
White to Off-White
Water Solubility
Water: Insoluble
InChIKey
OPQNCARIZFLNLF-VLSFGAMINA-N
FDA UNII
7 SUK7876BG · 7SUK7876BG
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302+H332-H315-H319-H335
Precautionary statements
261 · P261-P264-P301+P312-P302+P352-P304+P340+P312-P305+P351+P338

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302+H332 (38.9%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 72 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationMaytansine, 2'-de(acetylmethylamino)-2'-methyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (94.4%)

Safety data

wgk
3
rtecs
OQ2293000
hs_code
2941900000
risk_code
20/22-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
26-36
Hazard statements
H302+H332-H315-H319-H335
Precautionary statements
P261-P264-P301+P312-P302+P352-P304+P340+P312-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationAgents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.

Applications

DescriptionAnsamitocin P 3 is a macrocyclic antitumor antibiotic that works by depolymerizing microtubules in both interphase and mitosis, and perturbs chromosome segregation.

UsesAnsamitocin P-3 is an antitumor agent that binds to cell division protein FtsZ in Actinosynnema pretiosum.

Preparation methods · 1 item

PreparationMethod 1: An extraction, separation, and purification method for ansamitocin P-3, comprising the following steps: 1) Extracting the fermentation broth or solid fermentation medium after fermentation with an extraction solvent to obtain an extract; 2) Concentrating the extract obtained in step 1) until no extraction solvent flows out to obtain a concentrated crude extract A, then adding neutral alumina and mixing it evenly with an organic solvent; 3) Rotating the evenly mixed crude extract A from step 2) until it becomes a dry, sandy substance; 4) Adding an organic solvent to the dry, sandy crude extract A from step 3), shaking and allowing it to stand, and collecting the supernatant; 5) Concentrating the supernatant from step 4), adding silica gel and rotating it until it becomes a sandy substance, and eluting it by gradient column chromatography to obtain ansamitocin P-3.

Additional notes

DefinitionChEBI: A polyketide antibiotic that is isolated from Actinosynnema pretiosum and also exhibits antitumour activity.

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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66584-72-3
PubChem CID
443593
DTXSID
DTXSID801316919
EC Number
680-663-6
Hazard Codes
Xn
Risk Statements
20 · 20/22-36/37/38
Safety Statements
26 · 26-36
WGK Germany
3 · 3
RTECS
2293000 · OQ2293000
HS Code
2941900000 · 2941900000