Dihydrocapsaicin

Details

• Internal ID: 9642fa9d-ac3b-4d6f-8039-4277ac9d7fe0
• Taxonomy: Benzenoids > Phenols > Methoxyphenols
• IUPAC Name: N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide
• SMILES (Canonical): CC(C)CCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• SMILES (Isomeric): CC(C)CCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• InChI: InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)
• InChI Key: XJQPQKLURWNAAH-UHFFFAOYSA-N
• Popularity: 572 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₉NO₃
• Molecular Weight: 307.40 g/mol
• Exact Mass: 307.21474379 g/mol
• Topological Polar Surface Area (TPSA): 58.60 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.01
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

• 19408-84-5
• 6,7-Dihydrocapsaicin
• N-(4-hydroxy-3-methoxybenzyl)-8-methylnonanamide
• 8-Methyl-N-vanillylnonanamide
• dihydro capsaicin
• Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-
• CCRIS 1589
• N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide
• CHEBI:46932
• 8-methyl dihydrocapsaicin
• Nonanamide, 8-methyl-N-vanillyl-
• UNII-W9BV32M08A
• BRN 2815150
• 8-methyl-N-vanillyl-nonanamide
• W9BV32M08A
• N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methylnonanamide
• CAPSAICIN, DIHYDRO-
• DTXSID4041864
• Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-
• TNP00314
• DIHYDROCAPSAICIN (USP-RS)
• DIHYDROCAPSAICIN [USP-RS]
• SR-01000075976
• Dihydrocapsacine
• MFCD00057794
• Dihydrocapsaicin,(S)
• Lopac-M-1022
• Lopac0_000782
• CCRIS1589
• MLS002153458
• SCHEMBL119080
• CHEMBL311158
• DTXCID2021864
• XJQPQKLURWNAAH-UHFFFAOYSA-N
• HMS2232L10
• HMS3262M06
• HMS3371M21
• HMS3649N17
• BCP09851
• HY-N0361
• Dihydrocapsaicin, analytical standard
• Tox21_500782
• BDBM50231198
• STL570272
• ZB1859
• AKOS016009558
• CCG-204867
• LP00782
• SDCCGSBI-0050760.P002
• NCGC00015645-01
• NCGC00015645-02
• NCGC00015645-03
• NCGC00015645-04
• NCGC00015645-05
• NCGC00015645-06
• NCGC00015645-13
• NCGC00094119-01
• NCGC00094119-02
• NCGC00094119-03
• NCGC00261467-01
• AC-23369
• AS-77558
• LS-96829
• SMR001230817
• CS-0008911
• EU-0100782
• FT-0624952
• S9086
• Dihydrocapsaicin, from Capsicum sp., >=85%
• A14534
• C16952
• M 1022
• DIHYDROCAPSAICIN (CONSTITUENT OF CAPSICUM)
• Q-100236
• Q5276422
• SR-01000075976-1
• SR-01000075976-6
• DIHYDROCAPSAICIN (CONSTITUENT OF CAPSICUM) [DSC]
• N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-Nonanamide
• N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnonenamide
• Dihydrocapsaicin, United States Pharmacopeia (USP) Reference Standard

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	+	0.5454	54.54%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.9225	92.25%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.9526	95.26%
OATP1B3 inhibitior	+	0.9313	93.13%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	+	0.7966	79.66%
P-glycoprotein inhibitior	-	0.9076	90.76%
P-glycoprotein substrate	-	0.5661	56.61%
CYP3A4 substrate	+	0.5506	55.06%
CYP2C9 substrate	+	0.6284	62.84%
CYP2D6 substrate	-	0.7649	76.49%
CYP3A4 inhibition	+	0.7532	75.32%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.5294	52.94%
CYP2D6 inhibition	+	0.8320	83.20%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	+	0.5375	53.75%
CYP inhibitory promiscuity	-	0.8390	83.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7600	76.00%
Carcinogenicity (trinary)	Non-required	0.7134	71.34%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.4920	49.20%
Skin irritation	-	0.6036	60.36%
Skin corrosion	-	0.9436	94.36%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8613	86.13%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.7665	76.65%
skin sensitisation	-	0.8658	86.58%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8802	88.02%
Acute Oral Toxicity (c)	III	0.6752	67.52%
Estrogen receptor binding	+	0.7439	74.39%
Androgen receptor binding	-	0.6930	69.30%
Thyroid receptor binding	+	0.8688	86.88%
Glucocorticoid receptor binding	-	0.5990	59.90%
Aromatase binding	-	0.5683	56.83%
PPAR gamma	+	0.6554	65.54%
Honey bee toxicity	-	0.9346	93.46%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5824	58.24%
Fish aquatic toxicity	+	0.8003	80.03%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	12589.25 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	10000 nM; 2511.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	39810.7 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 12589.3 nM; 25118.9 nM; 12589.3 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	35481.3 nM	Potency	via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	12589.3 nM	Potency	via CMAUP
CHEMBL1293298	Q01453	Peripheral myelin protein 22	19011.5 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 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	99.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.73%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.56%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.89%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.65%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	94.47%	90.20%
CHEMBL2535	P11166	Glucose transporter	93.37%	98.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.35%	90.71%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.17%	97.29%
CHEMBL3492	P49721	Proteasome Macropain subunit	88.15%	90.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.90%	95.56%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.98%	85.31%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.94%	95.17%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	84.62%	96.25%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.48%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.32%	96.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.90%	92.88%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.65%	99.15%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.53%	97.21%
CHEMBL3401	O75469	Pregnane X receptor	82.15%	94.73%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.74%	100.00%
CHEMBL4208	P20618	Proteasome component C5	81.65%	90.00%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.20%	85.49%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	80.93%	96.67%

Plants that contains it

• Capsicum annuum
• Capsicum pubescens

Cross-Links

• PubChem: 107982
• NPASS: NPC218530
• ChEMBL: CHEMBL311158
• LOTUS: LTS0244691
• wikiData: Q5276422