Rhynchophylline - analytical standard, ≥98% , CAS No.76-66-4

CAS: 76-66-4 Cat. No.: R102720 Molecular Weight: 384.47 EC Number: 683-092-0

GRADE & PURITY Analytical standard, ≥98%

Synonyms

DTXSID70878612 | CCG-268460 | Rhynchophylline | RHYNCHOPHYLLINE (CONSTITUENT OF CAT'S CLAW) [DSC] | Rhynocophylline | C09236 | SCHEMBL2047380 | NSC-21731 | R0105 | CHEBI:70069 | NSC 21731 | Q7321711 | CORYNOXAN-16-CARBOXYLIC ACID, 16,17-DIDEHYDRO-17-METHO

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

DTXSID70878612 | CCG-268460 | Rhynchophylline | RHYNCHOPHYLLINE (CONSTITUENT OF CAT'S CLAW) [DSC] | Rhynocophylline | C09236 | SCHEMBL2047380 | NSC-21731 | R0105 | CHEBI:70069 | NSC 21731 | Q7321711 | CORYNOXAN-16-CARBOXYLIC ACID, 16, 17-DIDEHYDRO-17-METHO

Specifications & Purity

analytical standard, ≥98%

Biochemical and Physiological Mechanisms

Ca 2+ channel blocker. Non-competitive NMDA antagonist (IC 50 = 43.2 μM). Inhibits glutamate-induced neuronal death. Inhibits dopamine-induced apoptosis. Reduces endothelin-induced cerebral arteriole contraction.

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Grade

Analytical standard

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCC1CN2CCC3(C2CC1C(=COC)C(=O)OC)C4=CC=CC=C4NC3=O
• IUPAC Name: methyl (E)-2-[(3R,6'R,7'S,8'aS)-6'-ethyl-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate
• InChIKey: DAXYUDFNWXHGBE-KAXDATADSA-N
• INCHI: 1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1
• Isomeric SMILES: CC[C@H]1CN2CC[C@]3([C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)C4=CC=CC=C4NC3=O
• Molecular Weight: 384.47
• Reaxy-Rn: 902463
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=902463&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indolizidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indolizidines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Indolizidines
• Alternative Parents: Indolines Aralkylamines Piperidines N-alkylpyrrolidines Benzenoids Vinylogous esters Methyl esters Enoate esters Trialkylamines Secondary carboxylic acid amides Amino acids and derivatives Lactams Monocarboxylic acids and derivatives Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indole or derivatives - Dihydroindole - Indolizidine - Aralkylamine - Piperidine - N-alkylpyrrolidine - Benzenoid - Pyrrolidine - Methyl ester - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Vinylogous ester - Amino acid or derivatives - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid ester - Lactam - Azacycle - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Amine - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.
• External Descriptors: indolizines

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)

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

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

ACE Tclin Angiotensin-converting enzyme (1423 Activities)

Discover Target: ACE

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

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

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

KCNA2 Tclin Voltage-gated potassium channel subunit Kv1.2 (28 Activities)

Discover Target: KCNA2

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

HL-60 (67320 Activities)

Explore this target

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

SW480 (6023 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

• Melt Point(°C): 216°C
• Molecular Weight: 384.500 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 384.205 Da
• Monoisotopic Mass: 384.205 Da
• Topological Polar Surface Area: 67.900 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 663.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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

References

1. Meng Wang, Hui Li, Yaxin Zhao, Chuanfeng Lv, Guanghua Zhou.  (2018)  Rhynchophylline attenuates allergic bronchial asthma by inhibiting transforming growth factor‑β1‑mediated Smad and mitogen‑activated protein kinase signaling transductions in vivo and in vitro.  Experimental and Therapeutic Medicine,  17  (1): (251-259).  [PMID:30651790] [10.3892/etm.2018.6909]