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Chemistry

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Also known as: Resiniferatoxin, Chembl448382, Bdbm50366620

Molecular Formula

C₃₇H₄₀O₉

Molecular Weight

628.7 g/mol

InChI Key

DSDNAKHZNJAGHN-GGIHZKEUSA-N

Resiniferatoxin is a naturally occurring capsaicin analog found in the latex of the cactus Euphorbia resinifera with analgesic activity. Resiniferatoxin (RTX) binds to and activates the transient receptor potential vanilloid 1 (TRPV1), a non-selective cation channel in the plasma membrane of primary afferent sensory neurons. This increases the permeability to cations, and leads to an influx of calcium and sodium ions. This results in membrane depolarization, causing an irritant effect, followed by desensitization of the sensory neurons thereby inhibiting signal conduction in afferent pain pathways and causing analgesia. TRPV1, a member of the transient receptor potential channel (TRP) superfamily, is a heat- and chemo-sensitive calcium/sodium ion channel that is selectively expressed in a subpopulation of pain-sensing primary afferent neurons.

1 2D Structure

Resiniferatoxin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1R,2R,6R,10S,11R,15S,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate

2.1.2 InChI

InChI=1S/C37H40O9/c1-21(2)35-17-23(4)37-27(33(35)44-36(45-35,46-37)19-24-9-7-6-8-10-24)14-26(18-34(41)30(37)13-22(3)32(34)40)20-43-31(39)16-25-11-12-28(38)29(15-25)42-5/h6-15,23,27,30,33,38,41H,1,16-20H2,2-5H3/t23-,27+,30-,33-,34-,35+,36?,37-/m1/s1

2.1.3 InChI Key

DSDNAKHZNJAGHN-GGIHZKEUSA-N

2.1.4 Canonical SMILES

CC1CC2(C3C4C1(C5C=C(C(=O)C5(CC(=C4)COC(=O)CC6=CC(=C(C=C6)O)OC)O)C)OC(O3)(O2)CC7=CC=CC=C7)C(=C)C

2.1.5 Isomeric SMILES

C[C@@H]1C[C@@]2([C@H]3[C@H]4[C@]1([C@@H]5C=C(C(=O)[C@]5(CC(=C4)COC(=O)CC6=CC(=C(C=C6)O)OC)O)C)OC(O3)(O2)CC7=CC=CC=C7)C(=C)C

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Reciniferatoxin

2. Resiniferatoxin

3. Rtx Diterpene

2.2.2 Depositor-Supplied Synonyms

1. Resiniferatoxin

2. Chembl448382

3. Bdbm50366620

2.3 Create Date

2010-01-26

3 Chemical and Physical Properties

Molecular Formula	C₃₇H₄₀O₉
Molecular Weight	628.7 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	9
Exact Mass	628.26723285 g/mol
Monoisotopic Mass	628.26723285 g/mol
Topological Polar Surface Area	121 Å²
Heavy Atom Count	46
Formal Charge	0
Complexity	1330
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1