Himbacine - Moligand™, ≥98% , Antagonist of M 1 receptor;Antagonist of M 2 receptor;Antagonist of M 3 receptor;Antagonist of M 4 receptor;Antagonist of M 5 receptor, CAS No.6879-74-9, Antagonist of M 1 receptor;Antagonist of M 2 receptor;Antagonist of M 3 receptor;Antagonist of M 4 receptor;Antagonist of M 5 receptor

CAS: 6879-74-9 Cat. No.: H329511 Molecular Weight: 345.52 EC Number: 205-938-6

GRADE & PURITY Moligand™, ≥98%

Synonyms

(3S,3aR,4R,4aS,8aR,9aS)-4-[(E)-2-[(2R,6S)-1,6-dimethylpiperidin-2-yl]ethenyl]-3-methyl-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-3H-benzo[f][2]benzofuran-1-one | CHEBI:5720 | NSC-23969 | (+)-himbacine | 4-[2-[1,6-dimethyl-(2R,6S)-hexahydro-2-pyridinyl]-(E)-1-ethe

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Himbacine is an alkaloid muscarinic receptor antagonist displaying more potent activity associated with M2 and M2 subtypes over M1 or M3. Observations show himbacine bound tightly to various chimeric receptors in COS-7 cells as well as possessed the ability to bind to cardiac muscarinic receptors allosterically. Recent studies have produced series of thrombin receptor (PAR1) antagonists derived from himbacine Himbacine is an inhibitor of mAChR M2 and mAChR M4.

Specifications

Synonyms

(3S, 3aR, 4R, 4aS, 8aR, 9aS)-4-[(E)-2-[(2R, 6S)-1, 6-dimethylpiperidin-2-yl]ethenyl]-3-methyl-3a, 4, 4a, 5, 6, 7, 8, 8a, 9, 9a-decahydro-3H-benzo[f][2]benzofuran-1-one | CHEBI:5720 | NSC-23969 | (+)-himbacine | 4-[2-[1, 6-dimethyl-(2R, 6S)-hexahydro-2-pyridinyl]-(E)-1-ethe

Specifications & Purity

Moligand™, ≥98%

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.

Grade

Moligand™

Action Type

ANTAGONIST

Mechanism of action

Antagonist of M 1 receptor;Antagonist of M 2 receptor;Antagonist of M 3 receptor;Antagonist of M 4 receptor;Antagonist of M 5 receptor

Purity

≥98%

Product Properties

• pKa: pKa: 10.14
• Ki Data: Muscarinic acetylcholine receptor M1: Ki= 4.5 nM (human/CHO-KI cells); Cloned muscarinic acetylcholine receptor M2: Ki= 4.5 nM (human); Muscarinic acetylcholine receptor M2: Ki= 48.4 nM (human/CHO-KI cells); Cloned muscarinic acetylcholine receptor M1: Ki

Names and Identifiers

• Canonical Smiles: CC1CCCC(N1C)C=CC2C3CCCCC3CC4C2C(OC4=O)C
• IUPAC Name: (3S,3aR,4R,4aS,8aR,9aS)-4-[(E)-2-[(2R,6S)-1,6-dimethylpiperidin-2-yl]ethenyl]-3-methyl-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-3H-benzo[f][2]benzofuran-1-one
• InChIKey: FMPNFDSPHNUFOS-LPJDIUFZSA-N
• INCHI: 1S/C22H35NO2/c1-14-7-6-9-17(23(14)3)11-12-19-18-10-5-4-8-16(18)13-20-21(19)15(2)25-22(20)24/h11-12,14-21H,4-10,13H2,1-3H3/b12-11+/t14-,15-,16+,17+,18-,19+,20-,21+/m0/s1
• Isomeric SMILES: C[C@H]1CCC[C@@H](N1C)/C=C/[C@@H]2[C@H]3CCCC[C@@H]3C[C@H]4[C@@H]2[C@@H](OC4=O)C
• WGK Germany: 3
• RTECS: QL0843500
• Molecular Weight: 345.52
• Reaxy-Rn: 8132846
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8132846&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Naphthofurans

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Naphthofurans
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthofurans
• Alternative Parents: Piperidines Gamma butyrolactones Tetrahydrofurans Trialkylamines Carboxylic acid esters Amino acids and derivatives Oxacyclic compounds Monocarboxylic acids and derivatives Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Naphthofuran - Gamma butyrolactone - Piperidine - Tetrahydrofuran - Amino acid or derivatives - Carboxylic acid ester - Lactone - Tertiary amine - Tertiary aliphatic amine - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Oxacycle - Azacycle - Hydrocarbon derivative - Amine - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Carbonyl group - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthofurans. These are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
• External Descriptors: organic heterotricyclic compound - piperidine alkaloid - gamma-lactone

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)

CHRM5 Tclin Muscarinic acetylcholine receptor M5 (0 Activities)

Discover Target: CHRM5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM3 Tclin Muscarinic acetylcholine receptor M3 (2 Activities)

Discover Target: CHRM3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM4 Tclin Muscarinic acetylcholine receptor M4 (3 Activities)

Discover Target: CHRM4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (7 Activities)

Discover Target: CHRM2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (2 Activities)

Discover Target: CHRM1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

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

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

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

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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

CHRM4 Tclin Muscarinic acetylcholine receptor M4 (6041 Activities)

Discover Target: CHRM4

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

CHRM5 Tclin Muscarinic acetylcholine receptor M5 (4677 Activities)

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

CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

Discover Target: CHRM3

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

BCHE Tclin Butyrylcholinesterase (7174 Activities)

Discover Target: BCHE

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

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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

CHRM1 Tclin Muscarinic acetylcholine receptors; M1 & M2 (498 Activities)

Discover Target: CHRM1

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

Associated Targets(non-human)

Rattus norvegicus (775804 Activities)

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

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in ethanol (50 mg/ml), methanol, and dichloromethane. Insoluble in water.
• Refractive Index: n20D1.57
• Specific Rotation[α]: α20/D +51.4°, c = 1.01 in chloroform
• Boil Point(°C): ~469.6° C at 760 mmHg (Predicted)
• Melt Point(°C): 168.05° C (Predicted)
• Molecular Weight: 345.500 g/mol
• XLogP3: 5.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 345.267 Da
• Monoisotopic Mass: 345.267 Da
• Topological Polar Surface Area: 29.500 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 530.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• 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