(1S,2R,3R,5S,6S,16Z,18Z,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

• ChemBase ID: 133995
• Molecular Formular: C32H43ClN2O9
• Molecular Mass: 635.14482
• Monoisotopic Mass: 634.26570865
• SMILES: C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C\C=C(/Cc3cc(c(c(c3)OC)Cl)N(C(=O)C[C@@H]([C@]3([C@@H]1O3)C)OC(=O)C(C)C)C)\C)OC)(NC(=O)O2)O
• Canonical SMILES: CO[C@@H]1/C=C\C=C(\C)/Cc2cc(OC)c(c(c2)N(C(=O)C[C@@H]([C@]2([C@@H]([C@@H]([C@@H]3C[C@@]1(O)NC(=O)O3)C)O2)C)OC(=O)C(C)C)C)Cl
• InChI: 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
• InChIKey: OPQNCARIZFLNLF-NBLCDFCQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,3R,5S,6S,16Z,18Z,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1^1^0,^1^4.0^3,^5]hexacosa-10,12,14(26),16,18-pentaen-6-yl 2-methylpropanoate
• IUPAC Traditional name: (1S,2R,3R,5S,6S,16Z,18Z,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1^1^0,^1^4.0^3,^5]hexacosa-10,12,14(26),16,18-pentaen-6-yl 2-methylpropanoate
• Synonyms: Ansamitocin P-3 from Actinosynnema pretiosum

Database IDs

• CAS Number: 66584-72-3
• MDL Number: MFCD00274586
• PubChem SID: 24890696; 162228272
• PubChem CID: 71308748

CALCULATED PROPERTIES

• Acid pKa: 11.392377
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 4.5826306
• LogD (pH = 7.4): 4.582591
• Log P: 4.582631
• Molar Refractivity: 163.1607 cm^3
• Polarizability: 64.1003 Å^3
• Polar Surface Area: 136.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: OQ2293000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H332-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - A2836

Biochem/physiol Actions
Fungal metabolite with antineoplastic, antimitotic activity. Binds to tubulin and inhibits vinblastine-induced spiral formation.1