Indicine-N-Oxide

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

1 API Suppliers, 1 USDMF

REF. STANDARDS & IMPURITIES

2 Others

2 Others

Product Search

API SUPPLIERS

API Suppliers

US DMFs Filed

CEP/COS Certifications

JDMFs Filed

EU WC

Listed Suppliers

API REF. PRICE (USD / KG)

API Market Place

INTERMEDIATES

DOSSIERS // FDF

USA (Orange Book)

Europe

Canada

Australia

South Africa

Uploaded Dossiers

GLOBAL SALES (USD Million)

U.S. Medicaid

Annual Reports

FDF Market Place

EXCIPIENTS

PATENTS & EXCLUSIVITIES

USFDA Orange Book Patents

USFDA Exclusivities

DIGITAL CONTENT

Blog #PharmaFlow

News

REF STANDARD

EDQM

USP

Other Listed Suppliers

SERVICES

Also known as: 41708-76-3, Indicine-n-oxide, [(7r,8r)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3h-pyrrolizin-4-ium-1-yl]methyl (2r)-2-hydroxy-2-[(1s)-1-hydroxyethyl]-3-methylbutanoate, Nsc132319, Nsc-132319, Nsc 132319

Molecular Formula

C₁₅H₂₅NO₆

Molecular Weight

315.36 g/mol

InChI Key

DNAWGBOKUFFVMB-PZIGJSDBSA-N

Indicine-N-Oxide is a natural pyrrolizidine alkaloid with antineoplastic properties. Indicine-N-oxide alkylates and crosslinks DNA. (NCI04)

1 2D Structure

Indicine-N-Oxide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(7R,8R)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl (2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate

2.1.2 InChI

InChI=1S/C15H25NO6/c1-9(2)15(20,10(3)17)14(19)22-8-11-4-6-16(21)7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12+,13+,15+,16?/m0/s1

2.1.3 InChI Key

DNAWGBOKUFFVMB-PZIGJSDBSA-N

2.1.4 Canonical SMILES

CC(C)C(C(C)O)(C(=O)OCC1=CC[N+]2(C1C(CC2)O)[O-])O

2.1.5 Isomeric SMILES

C[C@@H]([C@](C(C)C)(C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)O)[O-])O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Indicine-n-oxide

2. Nsc 132319

2.2.2 Depositor-Supplied Synonyms

1. 41708-76-3

2. Indicine-n-oxide

3. [(7r,8r)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3h-pyrrolizin-4-ium-1-yl]methyl (2r)-2-hydroxy-2-[(1s)-1-hydroxyethyl]-3-methylbutanoate

4. Nsc132319

5. Nsc-132319

6. Nsc 132319

7. (+)-indicine N-oxide

8. Indicin-n-oxid

9. Indicine, N-oxide

10. Indicine N-oxide, Hplc Grade

11. Chembl512655

12. Dtxsid101315334

13. Bdbm50480295

14. Mfcd00866484

15. Nci60_000712

16. Hy-105529

17. Cs-0026202

18. [(7r,8r)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3h-pyrrolizin-4-ium-1-yl]methyl (2r)-2-hydroxy-2-[(1s)-1-hydroxyethyl]-3-methyl-butanoate

19. Butanoic Acid, (2r,3s)-dihydroxy-2-(1-methylethyl)-(2,3,5,7a-tetrahydro-(1r)-hydroxy-1h-pyrrolizin-7-yl)methyl Ester, N-oxide

20. Butanoic Acid,3-dihydroxy-2-(1-methylethyl)- (2,3,5,7a-tetrahydro-1-hydroxy-1h-pyrrolizin-7-yl) Methyl Ester, N-oxide, (1r-(1.alpha.,7(2r*,3s*),7a.beta))-

2.3 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₅NO₆
Molecular Weight	315.36 g/mol
XLogP3	-1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	315.16818752 g/mol
Monoisotopic Mass	315.16818752 g/mol
Topological Polar Surface Area	105 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	479
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)