7-Ethyl-10-(4-N-aminopentanoic acid)-1-piperidino)carbonyloxycamptothecin , CAS No.181467-56-1

CAS: 181467-56-1 Cat. No.: E338776 Molecular Weight: 618.68

Synonyms

4-[(4-Carboxybutyl)amino]-1-piperidinecarboxylic acid | Q27149594 | J-011587 | 1-Piperidinecarboxylic acid, 4-[(4-carboxybutyl)amino]-, (4S)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

7-Ethyl-10-(4-N-aminopentanoic acid)-1-piperidino)carbonyloxycamptothecin is a major metabolite of Irinotecan .

Specifications

Synonyms

4-[(4-Carboxybutyl)amino]-1-piperidinecarboxylic acid | Q27149594 | J-011587 | 1-Piperidinecarboxylic acid, 4-[(4-carboxybutyl)amino]-, (4S)-4, 11-diethyl-3, 4, 12, 14-tetrahydro-4-hydroxy-3, 14-dioxo-1H-pyrano[3', 4':6, 7]indolizino[1, 2-b]quinolin-9-yl ester |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)NCCCCC(=O)O
• IUPAC Name: 5-[[1-[[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl]oxycarbonyl]piperidin-4-yl]amino]pentanoic acid
• InChIKey: BSVVZICJFYZDJJ-XIFFEERXSA-N
• INCHI: 1S/C33H38N4O8/c1-3-21-22-15-20(45-32(42)36-13-10-19(11-14-36)34-12-6-5-7-28(38)39)8-9-26(22)35-29-23(21)17-37-27(29)16-25-24(30(37)40)18-44-31(41)33(25,43)4-2/h8-9,15-16,19,34,43H,3-7,10-14,17-18H2,1-2H3,(H,38,39)/t33-/m0/s1
• Isomeric SMILES: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)NCCCCC(=O)O
• Molecular Weight: 618.68
• Reaxy-Rn: 14334406
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=14334406&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Camptothecins

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Camptothecins
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Camptothecins
• Alternative Parents: Delta amino acids and derivatives Quinolines and derivatives Pyranopyridines Piperidinecarboxylic acids Pyridinones Aminopiperidines Benzenoids Dicarboxylic acids and derivatives Tertiary alcohols Carbamate esters Heteroaromatic compounds Amino acids Organic carbonic acids and derivatives Lactones Lactams Carboxylic acid esters Oxacyclic compounds Azacyclic compounds Dialkylamines Carboxylic acids Hydrocarbon derivatives Carbonyl compounds Organopnictogen compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Camptothecin - Delta amino acid or derivatives - Pyranopyridine - Quinoline - Piperidinecarboxylic acid - 4-aminopiperidine - Pyridinone - Piperidine - Dicarboxylic acid or derivatives - Pyridine - Benzenoid - Heteroaromatic compound - Carbamic acid ester - Tertiary alcohol - Carbonic acid derivative - Lactone - Lactam - Amino acid - Carboxylic acid ester - Amino acid or derivatives - Carboxylic acid derivative - Carboxylic acid - Secondary aliphatic amine - Oxacycle - Azacycle - Organoheterocyclic compound - Secondary amine - Hydrocarbon derivative - Amine - Organic oxide - Alcohol - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Carbonyl group - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
• External Descriptors: pyranoindolizinoquinoline

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

Chemical and Physical Properties

• Solubility: Soluble in DMSO and Methanol
• Refractive Index: n20D1.68 (Predicted)
• Boil Point(°C): ~953.5° C at 760 mmHg (Predicted)
• Melt Point(°C): 166-168° C
• Molecular Weight: 618.700 g/mol
• XLogP3: -0.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 618.269 Da
• Monoisotopic Mass: 618.269 Da
• Topological Polar Surface Area: 159.000 Ų
• Heavy Atom Count: 45
• Formal Charge: 0
• Complexity: 1260.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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