Resiniferatoxin

Details

• Internal ID: 7b59f696-e06f-47bc-af06-6159e38a2ee2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Rhamnofolane and daphnane diterpenoids
• IUPAC Name: [(1R,2R,6R,10S,11R,13S,15R,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
• 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
• InChI Key: DSDNAKHZNJAGHN-MXTYGGKSSA-N
• Popularity: 1,418 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₀O₉
• Molecular Weight: 628.70 g/mol
• Exact Mass: 628.26723285 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 4.50

Synonyms

• 57444-62-9
• Reciniferatoxin
• (+)-resiniferatoxin
• Lopain
• Mtx-071
• A5O6P1UL4I
• MTX-71
• DTXSID00894764
• CHEBI:8809
• 6,7-Deepoxy-6,7-didehydro-5-deoxy-21-dephenyl-21-(phenylmethyl)daphnetoxin 20-(3-hydroxy-5-methoxybenzeneacetate)
• Benzeneacetic acid, 4-hydroxy-3-methoxy-, ((2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-3a,3b,6,6a,9a,10,11,11a-octahydro-6a-hydroxy-8,10-dimethyl-11a-(1-methylethenyl)-7-oxo-2-(phenylmethyl)-7H-2,9b-epoxyazuleno(5,4-e)-1,3-benzodioxol-5-yl)methyl ester
• [(1R,2R,6R,10S,11R,13S,15R,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
• RTX diterpene
• Neuroclastin
• ((1R,2R,6R,10S,11R,13S,15R,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
• RefChem:879415
• DTXCID501324327
• ((1R,2R,6R,10S,11R,15R,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
• ((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
• 637-354-6
• RTX
• Resiniferatoxin [USAN]
• 4-hydroxy-3-methoxy-benzeneacetic acid, [(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-3a,3b,6,6a,9a,10,11,11a-octahydro-6a-hydroxy-8,10-dimethyl-11a-(1-methylethenyl)-7-oxo-2-(phenylmethyl)-7H-2,9b-epoxyazuleno[5,4-e]-1,3-benzodioxol-5-yl]methyl ester
• [3H]resiniferatoxin
• UNII-A5O6P1UL4I
• resinferatoxin
• Resiniferatoxin(RTX)
• RESINIFERATOXIN [INN]
• CHEMBL17976
• CHEMBL448382
• GTPL2491
• GTPL4091
• orb1695494
• RESINIFERATOXIN [WHO-DD]
• SCHEMBL17792942
• SCHEMBL29369231
• HY-N2333
• BDBM50052442
• EX-A11250
• WHO 11485
• AKOS024456409
• DB06515
• NCGC00162396-01
• DA-67160
• CS-0021288
• NS00018632
• G12655
• Q3277888
• (4-Hydroxy-3-methoxy-phenyl)-acetic acid (2R,3S,3aR,5R,5aR,8bR,11aR)-3b-benzyloxy-11a-hydroxy-5a-isopropenyl-2,4-dimethyl-1-oxo-1,3a,3b,4,5,5a,8a,8b,11,11a-decahydro-6,8-dioxa-indeno[5,4-e]azulen-10-ylmethyl ester
• [(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-2-Benzyl-6a-hydroxy-8,10-dimethyl-11a-(prop-1-en-2-yl)-7-oxo-3a,6,6a,7,9a,10,11,11a-octahydro-3bH-2,9b-epoxyazuleno[5,4-E]-1,3-benzodioxol-5-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate
• [(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-2-benzyl-6a-hydroxy-8,10-dimethyl-7-oxo-11a-(prop-1-en-2-yl)-3a,6,6a,7,9a,10,11,11a-octahydro-2H,3bH-2,9b-epoxyazuleno[4',5':5,6]benzo[1,2-d][1,3]dioxol-5-yl]methyl (4-hydroxy-3-methoxyphenyl)acetate
• [(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-2-benzyl-6a-hydroxy-8,10-dimethyl-7-oxo-11a-(prop-1-en-2-yl)-3a,6,6a,7,9a,10,11,11a-octahydro-3bH-2,9b-epoxyazuleno[4',5':5,6]benzo[1,2-d][1,3]dioxol-5-yl]methyl (4-hydroxy-3-methoxyphenyl)acetate
• 13-benzyl-6-hydroxy-15-isopropenyl-4,17-dimethyl-5-oxo-(1R,2S,6R,10S,11R,13S,15R,17R)-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-ylmethyl 2-(4-hydroxy-3-methoxyphenyl)acetate
• 13-benzyl-6-hydroxy-15-isopropenyl-4,17-dimethyl-5-oxo-(1R,2S,6R,10S,11R,15R,17R)-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-ylmethyl 2-(4-hydroxy-3-methoxyphenyl)acetate
• 13-benzyl-6-hydroxy-15-isopropenyl-4,17-dimethyl-5-oxo-(2S,6R,10S,11R,15R,17R)-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-ylmethyl 2-(4-hydroxy-3-methoxyphenyl)acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	19952.6 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4794	Q8NER1	Vanilloid receptor	1.23 nM; 0.019 nM	Kd; EC50	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.43%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.76%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.06%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.06%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.23%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.21%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.85%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.13%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.57%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.75%	95.89%
CHEMBL1795185	Q58F21	Bromodomain testis-specific protein	87.31%	89.76%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.09%	97.14%
CHEMBL1902	P62942	FK506-binding protein 1A	85.84%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.76%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.28%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.16%	92.62%
CHEMBL2535	P11166	Glucose transporter	84.25%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.75%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.30%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.78%	90.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.29%	96.61%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	80.73%	92.67%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.72%	91.71%

Plants that contains it

• Euphorbia resinifera

Cross-Links

• PubChem: 5702546
• NPASS: NPC108191
• ChEMBL: CHEMBL17976
• LOTUS: LTS0204591
• wikiData: Q3277888