Nogalamycin , CAS No.1404-15-5

CAS: 1404-15-5 Cat. No.: N343337 Formula: C₃₉H₄₉NO₁₆ Molecular Weight: 787.8 EC Number: 634-289-5

Synonyms

D05198 | UNII-L059DCD6IP | Antibiotic 205t3 | NOGALAMYCIN [USAN] | DTXSID20930779 | Methyl 11-((6-desoxy-3-C-methyl-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy)-4-dimethylamino-3,4,5,6,9,11,12,13,14,16-decahydro-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

An anthracyclic antitumor antibiotic.

Specifications

Synonyms

D05198 | UNII-L059DCD6IP | Antibiotic 205t3 | NOGALAMYCIN [USAN] | DTXSID20930779 | Methyl 11-((6-desoxy-3-C-methyl-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy)-4-dimethylamino-3,4,5,6,9,11,12,13,14,16-decahydro-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Names and Identifiers

Canonical Smiles

CC1C(C(C(C(O1)OC2CC(C(C3=CC4=C(C(=C23)O)C(=O)C5=C(C=C6C(=C5C4=O)OC7C(C(C(C6(O7)C)O)N(C)C)O)O)C(=O)OC)(C)O)OC)(C)OC)OC

IUPAC Name

methyl (1R,10S,12S,13R,21R,22S,23R,24R)-23-(dimethylamino)-4,8,12,22,24-pentahydroxy-1,12-dimethyl-6,17-dioxo-10-[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-4,6-dimethyloxan-2-yl]oxy-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2,4,7(16),8,14,18-hexaene-13-carboxylate

InChIKey

KGTDRFCXGRULNK-JYOBTZKQSA-N

INCHI

1S/C39H49NO16/c1-14-32(49-7)39(4,52-10)33(50-8)36(53-14)54-19-13-37(2,48)24(34(47)51-9)15-11-16-21(27(43)20(15)19)28(44)22-18(41)12-17-30(23(22)26(16)42)55-35-29(45)25(40(5)6)31(46)38(17,3)56-35/h11-12,14,19,24-25,29,31-33,35-36,41,43,45-46,48H,13H2,1-10H3/t14-,19-,24-,25-,29-,31+,32-,33-,35+,36-,37-,38+,39+/m0/s1

Isomeric SMILES

C[C@H]1[C@@H]([C@@]([C@H]([C@@H](O1)O[C@H]2C[C@]([C@@H](C3=CC4=C(C(=C23)O)C(=O)C5=C(C=C6C(=C5C4=O)O[C@H]7[C@H]([C@@H]([C@H]([C@@]6(O7)C)O)N(C)C)O)O)C(=O)OC)(C)O)OC)(C)OC)OC

Molecular Weight

787.8

Reaxy-Rn

10776830

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10776830&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Anthracyclines

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Anthracyclines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Anthracyclines
• Alternative Parents: Tetracenequinones Anthracenecarboxylic acids Aminoglycosides Anthraquinones Naphthalenecarboxylic acids and derivatives Hexoses O-glycosyl compounds Tetralins Aryl ketones Aralkylamines 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Oxanes Vinylogous acids Tertiary alcohols Methyl esters Secondary alcohols 1,2-aminoalcohols Trialkylamines Amino acids and derivatives Polyols Oxacyclic compounds Acetals Dialkyl ethers Monocarboxylic acids and derivatives Organopnictogen compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Anthracycline - Anthracyclinone-skeleton - Aminoglycoside core - Tetracenequinone - Anthracene carboxylic acid - Anthracene carboxylic acid or derivatives - 9,10-anthraquinone - 1,4-anthraquinone - Anthracene - 1-naphthalenecarboxylic acid or derivatives - Hexose monosaccharide - Glycosyl compound - O-glycosyl compound - Tetralin - Aryl ketone - Amino saccharide - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Aralkylamine - Benzenoid - Oxane - Monosaccharide - Methyl ester - Vinylogous acid - Tertiary alcohol - Tertiary aliphatic amine - Tertiary amine - Amino acid or derivatives - Secondary alcohol - Carboxylic acid ester - 1,2-aminoalcohol - Ketone - Ether - Dialkyl ether - Acetal - Carboxylic acid derivative - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Oxacycle - Polyol - Alcohol - Organic oxide - Organopnictogen compound - Organic oxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Organooxygen compound - Amine - Organonitrogen compound - Carbonyl group - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
• 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)

CCRF-CEM (65223 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

B16 (5829 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

L1210 (27553 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

P388 (20296 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 787.800 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 8
• Exact Mass: 787.305 Da
• Monoisotopic Mass: 787.305 Da
• Topological Polar Surface Area: 229.000 Ų
• Heavy Atom Count: 56
• Formal Charge: 0
• Complexity: 1530.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 13
• 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