13-Acetyl-9-dihydrobaccatin III - analytical standard , CAS No.142203-65-4

CAS: 142203-65-4 Cat. No.: A109792 Molecular Weight: 630.69 PubChem CID: 3083352

GRADE & PURITY Analytical standard

Synonyms

7,9-Dideacetyl baccatin VI | 4,10,13-Tris(acetyloxy)-1,7,9-trihydroxy-5,20-epoxytax-11-en-2-yl benzoate | 7,11-Methano-1H-cyclodeca(3,4)benz(1,2-b)oxete-4,5,6,9,11,12,12b-heptol, 2a,3,4,4a,5,6,9,10,12,12a-decahydro-4a,8,13,13-tetramethyl-, 6,9,12b-triacet

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

7, 9-Dideacetyl baccatin VI | 4, 10, 13-Tris(acetyloxy)-1, 7, 9-trihydroxy-5, 20-epoxytax-11-en-2-yl benzoate | 7, 11-Methano-1H-cyclodeca(3, 4)benz(1, 2-b)oxete-4, 5, 6, 9, 11, 12, 12b-heptol, 2a, 3, 4, 4a, 5, 6, 9, 10, 12, 12a-decahydro-4a, 8, 13, 13-tetramethyl-, 6, 9, 12b-triacet

Specifications & Purity

analytical standard

Biochemical and Physiological Mechanisms

9-Dihydro-13-acetylbaccatin III (9-DHAB III) is an intermediate for taxol analog preparations. There are a series of closely related natural organic compounds isolated from the Pacific yew tree (Taxus brevifolia) and related species. Taxo

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard

Names and Identifiers

• Canonical Smiles: CC1=C2C(C(C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)O)C)O)OC(=O)C
• IUPAC Name: [(1S,2S,3R,4S,7R,9S,10S,11R,12R,15S)-4,12,15-triacetyloxy-1,9,11-trihydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• InChIKey: WPPPFZJNKLMYBW-FAEUQDRCSA-N
• INCHI: 1S/C33H42O12/c1-16-21(42-17(2)34)14-33(40)28(44-29(39)20-11-9-8-10-12-20)26-31(7,22(37)13-23-32(26,15-41-23)45-19(4)36)27(38)25(43-18(3)35)24(16)30(33,5)6/h8-12,21-23,25-28,37-38,40H,13-15H2,1-7H3/t21-,22-,23+,25+,26-,27-,28-,31+,32-,33+/m0/s1
• Isomeric SMILES: CC1=C2[C@H]([C@@H]([C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)C)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)O)C)O)OC(=O)C
• PubChem CID: 3083352
• Molecular Weight: 630.69

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Diterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Diterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Taxanes and derivatives
• Alternative Parents: Tetracarboxylic acids and derivatives Benzoic acid esters Benzoyl derivatives Tertiary alcohols Secondary alcohols Oxetanes Cyclic alcohols and derivatives Carboxylic acid esters Polyols Oxacyclic compounds Dialkyl ethers Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Taxane diterpenoid - Tetracarboxylic acid or derivatives - Benzoate ester - Benzoic acid or derivatives - Benzoyl - Monocyclic benzene moiety - Benzenoid - Cyclic alcohol - Tertiary alcohol - Carboxylic acid ester - Secondary alcohol - Oxetane - Polyol - Ether - Dialkyl ether - Organoheterocyclic compound - Oxacycle - Carboxylic acid derivative - Alcohol - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] propellane ring system.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 630.700 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 9
• Exact Mass: 630.268 Da
• Monoisotopic Mass: 630.268 Da
• Topological Polar Surface Area: 175.000 Ų
• Heavy Atom Count: 45
• Formal Charge: 0
• Complexity: 1270.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1