Capsaicin

Details

• Internal ID: 1bf6a75d-36aa-415d-8ec9-3ddf443a46de
• Taxonomy: Benzenoids > Phenols > Methoxyphenols
• IUPAC Name: (E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
• SMILES (Canonical): CC(C)C=CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• SMILES (Isomeric): CC(C)/C=C/CCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• InChI: InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
• InChI Key: YKPUWZUDDOIDPM-SOFGYWHQSA-N
• Popularity: 20,612 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₇NO₃
• Molecular Weight: 305.40 g/mol
• Exact Mass: 305.19909372 g/mol
• Topological Polar Surface Area (TPSA): 58.60 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.79
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• 404-86-4
• Zostrix
• (E)-Capsaicin
• Qutenza
• CAPSAICINE
• Axsain
• Styptysat
• Isodecenoic acid vanillylamide
• Ausanil
• trans-Capsaicin
• E-CAPSAICIN
• NGX-4010
• trans-8-Methyl-N-vanillyl-6-nonenamide
• Mioton
• (E)-8-Methyl-N-vanillyl-6-nonenamide
• FEMA No. 3404
• Dolenon
• Ovocap
• Capzasin-hp
• Caswell No. 158
• Togarashi orenji
• ALGRX 4975
• Capsaicin [USAN]
• Ratden pe 40
• NCI-C56564
• NSC 56353
• Capsaicinoid
• CCRIS 1588
• CHEBI:3374
• HSDB 954
• Transacin
• 8-Methyl-N-vanillyl-trans-6-nonenamide
• 8-Methyl-N-Vanillyl-6-Nonenamide
• Cntx-4975
• NGX 4010
• NGX-1998
• EINECS 206-969-8
• 6-Nonenamide, 8-methyl-N-vanillyl-, (E)-
• UNII-S07O44R1ZM
• MFCD00017259
• NSC-56353
• trans-Capsaicin-d3
• (6E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
• EPA Pesticide Chemical Code 070701
• N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamide
• BRN 2816484
• ALGRX-4975
• S07O44R1ZM
• (E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
• DTXSID9020241
• 8-Methyl-N-vanillyl-6-nonenamide, (E)-
• Capsaicin (JAN/USP)
• (e)-n-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
• C18H27NO3
• NSC56353
• ZOSTRIX (TN)
• 1217899-52-9
• (6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
• 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (E)-
• 6-Nonenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-, (6E)-
• DTXCID30241
• CHEMBL294199
• (E)-N-((4-Hydroxy-3-methoxyphenyl)-methyl)-8-methyl-6-nonenamide
• 6-Nonenamide, (E)-N-((4-hydroxy-3-methoxy-phenyl)methyl)-8-methyl
• N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide, (E)-
• Capsaicin [in oleoresin of capsicum]
• n-(4-hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide
• N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
• NCGC00017337-02
• 8-Methyl-N-vanillyl-(trans)-6-nonenamide
• (E)-N-[(4-hydroxy-3-methoxy-phenyl)methyl]-8-methyl-non-6-enamide
• 6-Nonenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-, (E)-
• 7553-53-9
• CAPSAICIN (MART.)
• CAPSAICIN [MART.]
• (E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE
• CAPSAICIN (USP MONOGRAPH)
• CAPSAICIN [USP MONOGRAPH]
• Capsicine
• Vanilloid
• Zacin
• 6-Nonenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-
• Capsaicin (in oleoresin of capsicum)
• (6E)-N-{[4-hydroxy-3-(methyloxy)phenyl]methyl}-8-methylnon-6-enamide
• 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (6E)-
• SR-05000001861
• capsaicinum
• neurotoxic
• Capsaicina
• Isodecenoate
• Zucapsaicin;Civamide;cis-Capsaicin
• N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide
• Adlea
• TNP00277
• Capsaicin Patch
• (E)-N-((4-hydroxy-3-methoxy-phenyl)methyl)-8-methyl-non-6-enamide
• (E)-N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide
• (E)-N-[(4-Hydroxy-3-methoxyphenyl)-methyl]-8-methyl-6-nonenamide
• epsilon-capsaicin
• capsacin(E)
• Qutenza;Vanilloid
• Zostrix HP
• 8 Methyl N Vanillyl 6 Nonenamide
• Capsaicin,(S)
• Capsaicin [USP]
• 4DY
• CAS-404-86-4
• Prestwick_204
• Capsaicin (Natural)
• depletes Substance P
• CAPSAICINOIDS
• Citrus Aurantium 30%
• starbld0019180
• Capsaicin [INN:USP]
• Capsaicin [USP:INN]
• CAPSAICIN [INN]
• CAPSAICIN [JAN]
• CAPSAICIN [MI]
• isoamyl4-methoxycinnamate
• 6-Nonenamide, (E)-
• CAPSAICIN [HSDB]
• CAPSAICIN [INCI]
• Prestwick2_000879
• Prestwick3_000879
• Spectrum5_000538
• CAPSAICIN [VANDF]
• CAPSAICIN, NATURAL
• CITRUS AURANTIUM PE
• D0U5CE
• UPCMLD-DP092
• CAPSAICIN [USP-RS]
• CAPSAICIN [WHO-DD]
• SCHEMBL8085
• SCHEMBL8086
• MR3H3
• BSPBio_000957
• BSPBio_001548
• BSPBio_002917
• CAPSAICIN [EMA EPAR]
• MLS002154049
• N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide
• Capsaicin, analytical standard
• SPECTRUM1501128
• BPBio1_001053
• GTPL2486
• MEGxp0_001448
• CAPSAICIN [ORANGE BOOK]
• Methyl-N-vanillyl-6-noneneamide
• UPCMLD-DP092:001
• UPCMLD-DP092:002
• BDBM20461
• BDBM86537
• CHEBI:94524
• HMS501B16
• HMS1361N10
• HMS1570P19
• HMS1791N10
• HMS1921H11
• HMS1989N10
• HMS2089N11
• HMS2092D21
• HMS2097P19
• HMS2230O23
• HMS3402N10
• HMS3414F11
• HMS3649N15
• HMS3678F11
• Pharmakon1600-01501128
• 8-Methyl-N-vanillyl-6E-nonenamide
• AMY25669
• NGX-3781
• NGX-7325
• NSC_2548
• Tox21_110817
• Tox21_200315
• BBL027836
• CCG-39657
• CCG-39908
• EI-125
• HB1179
• HY-10448A
• LMFA08020085
• NSC757844
• s1990
• STL372889
• (E)8-methyl-N-vanillyl-6-Nonenamide
• AKOS007930159
• (6E)-N-
• CS-1518
• DB06774
• KS-5181
• LS-2138
• NSC-757844
• SDCCGMLS-0066678.P001
• TQ-1018
• Capsaicin 10 microg/mL in Acetonitrile
• Capsaicin, >=95%, from Capsicum sp.
• IDI1_000354
• IDI1_034018
• SMP2_000337
• USEPA/OPP Pesticide Code: 070701
• NCGC00017337-03
• NCGC00017337-04
• NCGC00017337-05
• NCGC00017337-06
• NCGC00017337-07
• NCGC00017337-08
• NCGC00017337-09
• NCGC00017337-10
• NCGC00017337-11
• NCGC00017337-12
• NCGC00017337-13
• NCGC00017337-17
• NCGC00017337-18
• NCGC00090853-01
• NCGC00090853-02
• NCGC00090853-03
• NCGC00090853-04
• NCGC00090853-06
• NCGC00090853-07
• NCGC00090853-08
• NCGC00090853-09
• NCGC00090853-10
• NCGC00090853-11
• NCGC00090853-12
• NCGC00257869-01
• AC-10114
• CAS_404-86-4
• HY-10448
• SMR000718774
• CAPSAICIN (CONSTITUENT OF CAPSICUM)
• Nonenamide, 8-methyl-N-vanillyl-, (E)-
• SBI-0052593.P002
• CS-0181240
• M1149
• (E)-8-Methyl-N-vanillyl-6-nonenamide(8cl)
• C-1700
• C06866
• D00250
• AB00053098-11
• AB00053098_12
• Capsaicin, from Capsicum sp., >=50% (HPLC)
• EN300-7544118
• CAPSAICIN (CONSTITUENT OF CAPSICUM) [DSC]
• Q273169
• SR-05000001861-1
• SR-05000001861-4
• SR-05000001861-5
• SR-05000001861-6
• SR-05000001861-9
• BRD-K37056290-001-01-1
• BRD-K50590187-001-06-6
• Capsaicin, certified reference material, TraceCERT(R)
• N-(3-Methoxy-4-hydroxybenzyl)-8-methyl-6-nonenamide
• Flavor and Extract Manufacturers' Association No. 3404
• Capsaicin (transdermal patch formulation, neuropathic pain)
• Capsaicin, European Pharmacopoeia (EP) Reference Standard
• N-(4-hydroxy-3-methoxyphenylmethyl)-8-Methyl-6-Nonenamide
• (6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide #
• Capsaicin, United States Pharmacopeia (USP) Reference Standard
• Capsaicin; 8-Methyl-N-vanillyl-trans-6-nonenamide; NGX-4010
• N-[(4-hydroxy-3-methoxyphenyl)methyl]-6E-8-methyl-nonenamide
• (6e)-n-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide
• 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-(E)-
• CAPSAICIN (2444-46-4 NONIVAMIDE (SYNTHETIC CAPSAICIN))
• N-(4-HYDROXY-3-METHOXYBENZYL)-8-METHYL-6-NONENAMIDE [FHFI]
• trans-N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide
• 6-nonanamida, N-[(4-hidroxi-3-metoxifenil) metil]-8-metil-, (6E)-
• 6-nonenamide,n-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-,(6e)-
• Capsaicin, Pharmaceutical Secondary Standard; Certified Reference Material
• Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8 -methyl-, (E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	-	0.6205	62.05%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.9272	92.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8679	86.79%
OATP1B3 inhibitior	+	0.9404	94.04%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.8872	88.72%
P-glycoprotein inhibitior	-	0.8841	88.41%
P-glycoprotein substrate	-	0.7628	76.28%
CYP3A4 substrate	+	0.5094	50.94%
CYP2C9 substrate	+	0.6153	61.53%
CYP2D6 substrate	-	0.7925	79.25%
CYP3A4 inhibition	+	0.8287	82.87%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.6667	66.67%
CYP inhibitory promiscuity	-	0.7551	75.51%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8071	80.71%
Carcinogenicity (trinary)	Non-required	0.6924	69.24%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.5473	54.73%
Skin irritation	+	0.5683	56.83%
Skin corrosion	-	0.9425	94.25%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8643	86.43%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.9323	93.23%
skin sensitisation	-	0.8775	87.75%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8599	85.99%
Acute Oral Toxicity (c)	III	0.6676	66.76%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	-	0.6803	68.03%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	-	0.6040	60.40%
Aromatase binding	-	0.5481	54.81%
PPAR gamma	+	0.6998	69.98%
Honey bee toxicity	-	0.8898	88.98%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.6765	67.65%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM; 15848.9 nM; 28183.8 nM; 22387.2 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	31622.8 nM	Potency	via CMAUP
CHEMBL221	P23219	Cyclooxygenase-1	3800 nM; 1551 nM	IC50; IC50	PMID: 16038536; via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	3000 nM	IC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	2511.9 nM; 2511.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	31622.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	15848.9 nM; 17782.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	35481.3 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	22387.2 nM	Potency	via CMAUP
CHEMBL4794	Q8NER1	Vanilloid receptor	28.2 nM; 2.512 nM; 8 nM	EC50; EC50; IC50	via Super-PRED; via Super-PRED; PMID: 25666822

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.65%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	99.08%	99.17%
CHEMBL2581	P07339	Cathepsin D	98.78%	98.95%
CHEMBL2535	P11166	Glucose transporter	96.98%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.94%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.40%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	94.41%	90.20%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.68%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.25%	95.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.14%	90.71%
CHEMBL3492	P49721	Proteasome Macropain subunit	89.03%	90.24%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.14%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.86%	99.15%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	85.95%	96.67%
CHEMBL4208	P20618	Proteasome component C5	85.89%	90.00%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	85.37%	98.11%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	84.20%	92.88%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.90%	97.29%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.53%	97.21%
CHEMBL3401	O75469	Pregnane X receptor	82.43%	94.73%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	81.58%	89.33%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	81.14%	96.25%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.97%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.58%	91.19%

Plants that contains it

• Campsis grandiflora
• Capsicum annuum
• Capsicum annuum var. glabriusculum
• Capsicum pubescens
• Glehnia littoralis
• Mangifera indica

Cross-Links

• PubChem: 1548943
• NPASS: NPC255550
• ChEMBL: CHEMBL294199
• LOTUS: LTS0241286
• wikiData: Q273169