Cephalomannine - 10mM in DMSO , CAS No.71610-00-9

CAS: 71610-00-9 Cat. No.: C580343 Molecular Weight: 831.9 EC Number: 630-569-6

GRADE & PURITY 10mM in DMSO

Synonyms

Benzenepropanoic acid, alpha-hydroxy-beta-(((2E)-2-methyl-1-oxo-2-butenyl)amino)-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-meth

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Cephalomannine is an active anti-cancer agent obtained from Taxus yunnanensis and has an antineoplastic effect on tumors found in mice.
A potential antineoplastic compound

Specifications

Synonyms

Benzenepropanoic acid, alpha-hydroxy-beta-(((2E)-2-methyl-1-oxo-2-butenyl)amino)-, (2aR, 4S, 4aS, 6R, 9S, 11S, 12S, 12aR, 12bS)-6, 12b-bis(acetyloxy)-12-(benzoyloxy)-2a, 3, 4, 4a, 5, 6, 9, 10, 11, 12, 12a, 12b-dodecahydro-4, 11-dihydroxy-4a, 8, 13, 13-tetramethyl-5-oxo-7, 11-meth

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Cephalomannine, isolated from Taxus yunnanensis, has shown some antineoplastic effects on tumors in mice

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Canonical Smiles: CC=C(C)C(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• IUPAC Name: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• InChIKey: DBXFAPJCZABTDR-WBYYIXQISA-N
• INCHI: 1S/C45H53NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h9-19,29-31,33-36,38,49-50,55H,20-22H2,1-8H3,(H,46,52)/b23-9+/t29-,30-,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1
• Isomeric SMILES: C/C=C(\C)/C(=O)N[C@@H](C1=CC=CC=C1)[C@H](C(=O)O[C@H]2C[C@]3([C@H]([C@H]4[C@@]([C@H](C[C@@H]5[C@]4(CO5)OC(=O)C)O)(C(=O)[C@@H](C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• WGK Germany: 3
• Molecular Weight: 831.9
• Reaxy-Rn: 25329952
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25329952&ln=

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 Beta amino acids and derivatives Benzoic acid esters Benzoyl derivatives Alpha-acyloxy ketones Fatty acid esters Monosaccharides N-acyl amines Tertiary alcohols Secondary carboxylic acid amides Secondary alcohols Oxetanes Carboxylic acid esters Cyclic alcohols and derivatives Ketones Dialkyl ethers Oxacyclic compounds Organopnictogen compounds Hydrocarbon derivatives Organonitrogen compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Taxane diterpenoid - Tetracarboxylic acid or derivatives - Beta amino acid or derivatives - Benzoate ester - Benzoic acid or derivatives - Benzoyl - Alpha-acyloxy ketone - Fatty acid ester - Monocyclic benzene moiety - Monosaccharide - Fatty acyl - N-acyl-amine - Benzenoid - Tertiary alcohol - Cyclic alcohol - Oxetane - Secondary alcohol - Secondary carboxylic acid amide - Carboxylic acid ester - Carboxamide group - Ketone - Oxacycle - Carboxylic acid derivative - Organoheterocyclic compound - Dialkyl ether - Ether - Alcohol - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Organooxygen compound - Organic oxygen compound - Organopnictogen compound - Organonitrogen 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

Associated Targets(Human)

BGC-823 (3035 Activities)

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HCT-8 (3484 Activities)

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MCF7 (126967 Activities)

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SW480 (6023 Activities)

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A549 (127892 Activities)

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Bel-7402 (4577 Activities)

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HepG2 (196354 Activities)

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A2780 (11979 Activities)

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IGROV-1 (47897 Activities)

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KB (17409 Activities)

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Associated Targets(non-human)

Artemia (698 Activities)

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P388 (20296 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO >100 mg/ml Ethanol 150 mg/ml
• Sensitivity: Light sensitive
• Molecular Weight: 831.900 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 14
• Exact Mass: 831.347 Da
• Monoisotopic Mass: 831.347 Da
• Topological Polar Surface Area: 221.000 Ų
• Heavy Atom Count: 60
• Formal Charge: 0
• Complexity: 1790.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1