Nonivamide

Details

• Internal ID: 0a6cc0ce-4bab-45eb-8837-92087adc1c26
• Taxonomy: Benzenoids > Phenols > Methoxyphenols
• IUPAC Name: N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
• SMILES (Canonical): CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• SMILES (Isomeric): CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• InChI: InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)
• InChI Key: RGOVYLWUIBMPGK-UHFFFAOYSA-N
• Popularity: 230 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₇NO₃
• Molecular Weight: 293.40 g/mol
• Exact Mass: 293.19909372 g/mol
• Topological Polar Surface Area (TPSA): 58.60 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.77
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

• 2444-46-4
• N-Vanillylnonanamide
• Pseudocapsaicin
• Pelargonic acid vanillylamide
• N-Vanillylnonamide
• N-Vanillylpelargonamide
• N-(4-Hydroxy-3-methoxybenzyl)nonanamide
• Nonanoic acid vanillylamide
• N-Nonanoyl vanillylamide
• Vanillyl pelargonic amide
• Vanillyl-N-nonylamide
• Pelargonyl vanillylamide
• Hydroxymethoxybenzyl pelargonamide
• Nonylic acid vanillylamide
• Vanillyl n-nonoylamide
• Nonanamide, N-vanillyl-
• Nonanoyl vanillylamide
• FEMA No. 2787
• Nonivamide [INN]
• Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-
• Nonivamidum
• Hansaplast
• Nonivamida
• desmethyldihydrocapsaicin
• NSC 172795
• Nonanoyl 4-hydroxy-3-methoxybenzylamide
• N-Vanillylnonanoamide
• N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
• PAVA
• Vanillyl n-Nonylamide
• Nonylic acid vanillyamide
• Nonivamidum [INN-Latin]
• vanillylnonanamide
• Nonivamida [INN-Spanish]
• EINECS 219-484-1
• NSC-172795
• UNII-S846B891OR
• BRN 2144300
• N-((4-Hydroxy-3-methoxyphenyl)methyl)nonanamide
• N-((Hydroxy-3-methoxyphenyl)methyl)4-nonanamide
• N-vanillyl nonanamide
• CHEBI:46936
• S846B891OR
• AH-23491X
• CHEMBL75124
• DTXSID1034769
• Benzamide, 4-hydroxy-3-methoxy-N-(1-oxononyl)-
• Nonivamide (INN)
• Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-
• NCGC00016089-05
• Nonylvanylamide
• NONIVAMIDE (MART.)
• NONIVAMIDE [MART.]
• DTXCID9014769
• vanillylnonamide
• CAS-2444-46-4
• 8-Nordihydrocapsaicin
• N-vanillyl-nonanamide
• Nonanoylvanillyl Amide
• Capsaicin (Synthetic)
• N-((4-Hydroxy-3-methoxyphenyl)methyl)-Nonanamide
• N-[(4-Hydroxy-3-methoxyphenyl)methyl]-Nonanamide
• capscaisin
• N-Nonylvanylamide
• PAVA spray
• Hansaplast (TN)
• Nonanoylvanilylamide
• Nonylic vanillamide
• Synthetic capsaicin
• Nonoyl vanillylamide
• PSVA
• nonylicacidvanillylamide
• Spectrum_000311
• Pelargonoyl vanillylamide
• SpecPlus_000799
• N-Pelargonylvanillylamide
• Spectrum2_001091
• Spectrum4_000916
• Spectrum5_001853
• Lopac-V-9130
• N-Vanillylnonanamide, 8CI
• NONIVAMIDE [WHO-DD]
• Lopac0_001218
• SCHEMBL81939
• KBioGR_001412
• KBioSS_000791
• MLS002153373
• DivK1c_006895
• SPECTRUM2300192
• SPBio_001162
• N-Pelargonic Acid Vanillylamide
• FEMA 2787
• KBio1_001839
• KBio2_000791
• KBio2_003359
• KBio2_005927
• HH 50
• HMS2234E23
• HMS3374K02
• HMS3885C14
• Pharmakon1600-01506172
• Tox21_110302
• Tox21_301218
• BDBM50044767
• CCG-39764
• MFCD00017286
• NSC172795
• NSC760391
• s3935
• AKOS001719931
• N-Vanillylnonanamide, >=97%, powder
• Tox21_110302_1
• AC-4807
• DB11324
• LS-2128
• NSC-760391
• N-Vanillylnonanamide, analytical standard
• NCGC00016089-01
• NCGC00016089-02
• NCGC00016089-03
• NCGC00016089-04
• NCGC00016089-06
• NCGC00094463-01
• NCGC00094463-02
• NCGC00094463-03
• NCGC00094463-04
• NCGC00255553-01
• AS-13519
• HY-17568
• SMR001230764
• LS-176202
• N-(4-Hydroxy-3-methoxybenzyl)nonanamide #
• NONIVAMIDE (CONSTITUENT OF CAPSICUM)
• EU-0101218
• FT-0603609
• FT-0623446
• M0900
• Nonanamide, N-(4-hydroxy-3-methoxybenzyl)-
• 4-Hydroxy-3-methoxy-N-(1-oxononyl)-Benzamide
• D08282
• V 9130
• V-3000
• AB00053157_06
• EN300-1692889
• HYDROXYMETHOXYBENZYL PELARGONAMIDE [INCI]
• n-((4-hydroxy-3-methoxyphenyl)methyl)-nonanamid
• Nonanamide, N-((4-hydroxy-3-methoxyphenyl)meth
• A817309
• N-NONANOYL-4-HYDROXY-3-METHOXYBENZYL-AMIDE
• NONIVAMIDE (CONSTITUENT OF CAPSICUM) [DSC]
• Q420228
• SR-01000076196
• SR-01000076196-1
• N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide, 9CI
• Z373586944
• N-NONANOYL-4-HYDROXY-3-METHOXYBENZYL-AMIDE [FHFI]
• Nonivamide, European Pharmacopoeia (EP) Reference Standard
• NONIVAMIDE (SYNTHETIC CAPSAICIN) (SEE ALSO CAPSAICIN: 404-86-4)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9951	99.51%
Caco-2	+	0.6136	61.36%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.9147	91.47%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.9243	92.43%
OATP1B3 inhibitior	+	0.9342	93.42%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.8500	85.00%
BSEP inhibitior	+	0.6871	68.71%
P-glycoprotein inhibitior	-	0.9261	92.61%
P-glycoprotein substrate	-	0.6287	62.87%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	0.5581	55.81%
CYP2D6 substrate	-	0.7538	75.38%
CYP3A4 inhibition	+	0.6579	65.79%
CYP2C9 inhibition	+	0.5698	56.98%
CYP2C19 inhibition	-	0.5699	56.99%
CYP2D6 inhibition	+	0.8426	84.26%
CYP1A2 inhibition	+	0.9359	93.59%
CYP2C8 inhibition	+	0.8805	88.05%
CYP inhibitory promiscuity	-	0.7962	79.62%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.7171	71.71%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.5392	53.92%
Skin irritation	-	0.6425	64.25%
Skin corrosion	-	0.9523	95.23%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7618	76.18%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.6966	69.66%
skin sensitisation	-	0.8615	86.15%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7993	79.93%
Acute Oral Toxicity (c)	III	0.6916	69.16%
Estrogen receptor binding	+	0.8268	82.68%
Androgen receptor binding	-	0.7101	71.01%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	+	0.6748	67.48%
Aromatase binding	-	0.5324	53.24%
PPAR gamma	+	0.7451	74.51%
Honey bee toxicity	-	0.9679	96.79%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.8138	81.38%
Fish aquatic toxicity	+	0.8074	80.74%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	22387.2 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	25118.9 nM	Potency	via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	12589.25 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	7943.28 nM	AC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	3162.28 nM	AC50	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	25118.86 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 3981.1 nM; 25118.9 nM; 3981.1 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293298	Q01453	Peripheral myelin protein 22	8492.1 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.19%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	99.03%	99.17%
CHEMBL2581	P07339	Cathepsin D	98.75%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.46%	96.09%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	94.55%	92.08%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.93%	97.29%
CHEMBL2535	P11166	Glucose transporter	90.95%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	90.84%	90.20%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.10%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.93%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.79%	95.56%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	82.18%	96.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.70%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.50%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.25%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.02%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.88%	96.95%
CHEMBL4208	P20618	Proteasome component C5	80.48%	90.00%

Plants that contains it

• Capsicum annuum

Cross-Links

• PubChem: 2998
• NPASS: NPC93882
• ChEMBL: CHEMBL75124
• LOTUS: LTS0096968
• wikiData: Q105288659