Crotaline - 10mM in DMSO , CAS No.315-22-0

CAS: 315-22-0 Cat. No.: C423269 Formule: C₁₆H₂₃NO₆ Poids moléculaire: 325.36 Beilstein Registry Number: 48732 Numéro CE: 628-506-2

QUALITÉ & PURETÉ 10mM in DMSO

Synonyms

(3R,4R,5R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione|rel-(3R,4R,5R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione|(2,3,4-gh)pyrrolizine-2,6(3H)-dione, (4,5,8,10,12,13,13a,13b)-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-|Crotaline|monocrotaline|12-beta,13-beta-Dihydroxy-12-alpha,13-alpha,14-alpha-trimethylcrotal-1-enine|2H-(1,6)Dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)-|2H-(1,6)DIOXACYCLOUNDECINO(2,3,4-GH)PYRROLIZINE-2,6(3H)-DIONE, 4,5,8,10,12,13,13A,13B-OCTAHYDRO-4,5-DIHYDROXY-3,4,5-TRIMETHYL-, (3R-(3R*,4R*,5R*,13AR*,13BR*))-|20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)-|20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13alpha,14alpha)-|(-)-Monocrotaline|JACS 72: 158 (1950)|14,19-Dihydro-12,13-dihydroxy(13-alpha,14-alpha)-20-norcrotalanan-11,15-dione|MONOCROTALINE [MI]|Monocrotalin|2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)-|(3R,4R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione|Retronecine cyclic 2,3-dihydroxy-2,3,4-trimethylglutarate|(3R,4R,5R,13aR,13bR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione|MONOCROTALINE [HSDB]|(1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione|14,19-Dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione|MONOCROTALINE [IARC]

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Vue d’ensemble

Monocrotaline is a toxic, pyrrolizidine alkaloid. It is used for inducing pulmonary diseases in rats. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature.
A toxic, pyrrolizidine alkaloid

Spécifications

Synonymes

(3R,4R,5R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione | rel-(3R,4R,5R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione | (2,3,4-gh)pyrrolizine-2,6(3H)-dione, (4, Afficher plus

Spécifications et pureté

10mM in DMSO

Mécanismes biochimiques et physiologiques

Rotaline can induce pulmonary vascular syndrome in rats. This component is known to be toxic and can cause cirrhosis, liver enlargement, sinus syndrome, and right ventricular hypertrophy

Conditions de stockage de stockage

Store at -80°C

Expédié en

Dry ice packs + Cold packs

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Noms et identifiants

Pubchem Sid

528776056

Sourires canoniques

CC1C(=O)OC2CCN3C2C(=CC3)COC(=O)C(C1(C)O)(C)O

IUPAC Name

(1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione

InChIKey

QVCMHGGNRFRMAD-XFGHUUIASA-N

INCHI

1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1

Isomères SMILES

C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O

WGK Allemagne

3

RTECS

QB3140000

Numéro ONU

1544

Poids moléculaire

325.36

Beilstein

48732

Reaxy-Rn

628332

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=628332&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Pyrrolizines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Pyrrolizines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrrolizines
• Alternative Parents: N-alkylpyrrolidines Dicarboxylic acids and derivatives Tertiary alcohols Pyrrolines Trialkylamines Lactones Carboxylic acid esters Amino acids and derivatives 1,2-diols Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Pyrrolizine - Dicarboxylic acid or derivatives - N-alkylpyrrolidine - Pyrrolidine - Pyrroline - Tertiary alcohol - 1,2-diol - Amino acid or derivatives - Carboxylic acid ester - Lactone - Tertiary aliphatic amine - Tertiary amine - Carboxylic acid derivative - Oxacycle - Azacycle - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Carbonyl group - Organic oxygen compound - Amine - Organooxygen compound - Alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrrolizines. These are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring.
• External Descriptors: Pyrrolizidine alkaloids

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

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Mécanismes d'action

Propriétés chimiques et physiques

• Sensibilité: Light sensitive
• Point de fusion (°C): 204°C
• Poids moléculaire: 325.360 g/mol
• XLogP3: -0.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 325.153 Da
• Monoisotopic Mass: 325.153 Da
• Topological Polar Surface Area: 96.300 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 575.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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