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Dipsaicin
- Family: Plantae - Dipsacaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenolic Glycoside
| Canonical Smiles | Oc1ccc(c(c1)C)C(=O)O |
|---|---|
| InChI | InChI=1S/C8H8O3/c1-5-4-6(9)2-3-7(5)8(10)11/h2-4,9H,1H3,(H,10,11) |
| InChIKey | BBMFSGOFUHEVNP-UHFFFAOYSA-N |
| Formula | C8H8O3 |
| HBA | 2 |
| HBD | 2 |
| MW | 152.15 |
| Rotatable Bonds | 1 |
| TPSA | 57.53 |
| LogP | 1.4 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.12 |
| Exact Mass | 152.05 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Dipsacus laciniatus | Dipsacaceae | Plantae | 398307 |
Showing of synonyms
Dipsaicin
4-hydroxy-2-methylbenzoic acid
578-39-2
4-Hydroxy-o-toluic acid
4,2-Cresotic acid
Benzoic acid, 4-hydroxy-2-methyl-
2-methyl-4-hydroxybenzoic acid
U4NMG5AH8R
EINECS 209-422-1
NSC 85496
NSC-85496
DTXSID10206490
4-hydroxy-2-methylbenzoate
DTXCID10128981
209-422-1
MFCD02182261
4-hydroxy-2-methylbenzoicacid
4-hydroxy-2-methyl-benzoic acid
NSC85496
UNII-U4NMG5AH8R
Methyl p-hydroxybenzoic acid
SCHEMBL39526
CHEMBL4250257
Para-hydroxy-methyl-benzoic acid
4-Hydroxy-2-methyl benzoic acid
BBMFSGOFUHEVNP-UHFFFAOYSA-N
CHEBI:167791
BCP24571
AKOS005256094
4-Hydroxy-2-methylbenzoic acid, 98%
AC-7750
CS-W016305
FS-3561
SY014356
H1311
NS00014690
EN300-117016
AL-398/25017049
Z1255361025
- Abdallah OM (1991). Phenolic glucoside and other constituents of Dipsacus laciniatus. Phytochemistry,1991,30(8),2805-2806. [View]
Pubchem:
68475
Cas:
578-39-2
Zinc:
ZINC000004266368
Chebi:
167791
Nmrshiftdb2:
70065017
Chembl:
CHEMBL4250257
Comptox:
DTXSID10206490
No compound-protein relationship available.
SMILES: c1ccccc1
Level: 0
Mol. Weight: 152.15 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.81
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.710
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.43
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.170
- Plasma Protein Binding
- 36.05
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 15.660
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.280
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 2.440
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 2.040
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 3.200
- Rat (Acute)
- 2.530
- Rat (Chronic Oral)
- 2.760
- Fathead Minnow
- 3.400
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 299.370
- Hydration Free Energy
- -6.580
- Log(D) at pH=7.4
- -0.260
- Log(P)
- 1.82
- Log S
- -2.1
- Log(Vapor Pressure)
- -4.92
- Melting Point
- 240.74
- pKa Acid
- 4.3
- pKa Basic
- 5.59
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9496 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9496 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9463 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9463 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.9359 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.9359 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.9318 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.9318 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9296 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9296 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.9173 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.9173 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.9137 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.9137 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.9081 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.9081 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.9040 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.9040 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.9025 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.9025 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9010 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9010 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8986 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8986 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8816 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8816 |
| Carbonic anhydrase 5A, mitochondrial | P23589 | CAH5A_MOUSE | Mus musculus | 3 | 0.8756 |
| Carbonic anhydrase 5A, mitochondrial | P23589 | CAH5A_MOUSE | Mus musculus | 3 | 0.8756 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8526 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8526 |
| Carbonic anhydrase 13 | Q8N1Q1 | CAH13_HUMAN | Homo sapiens | 3 | 0.8455 |
| Carbonic anhydrase 13 | Q8N1Q1 | CAH13_HUMAN | Homo sapiens | 3 | 0.8455 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8413 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8413 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8213 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8213 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8120 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8120 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.8118 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.8118 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.8004 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.8004 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7881 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7881 |
| L-lactate dehydrogenase (cytochrome) | P00175 | CYB2_YEAST | Saccharomyces cerevisiae | 3 | 0.7867 |
| L-lactate dehydrogenase (cytochrome) | P00175 | CYB2_YEAST | Saccharomyces cerevisiae | 3 | 0.7867 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7823 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7823 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7819 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7819 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7796 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7796 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.7773 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.7773 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.7701 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.7701 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7697 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7697 |
| Dicamba O-demethylase, oxygenase component | Q5S3I3 | DDMC_STEMA | Stenotrophomonas maltophilia | 3 | 0.7681 |
| Dicamba O-demethylase, oxygenase component | Q5S3I3 | DDMC_STEMA | Stenotrophomonas maltophilia | 3 | 0.7681 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 3 | 0.7599 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 3 | 0.7599 |
| cAMP-dependent protein kinase catalytic subunit alpha | P17612 | KAPCA_HUMAN | Homo sapiens | 3 | 0.7561 |
| cAMP-dependent protein kinase catalytic subunit alpha | P17612 | KAPCA_HUMAN | Homo sapiens | 3 | 0.7561 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7512 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7512 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 2 | 0.7509 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 2 | 0.7509 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7452 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7452 |
| Kynurenine 3-monooxygenase | P38169 | KMO_YEAST | Saccharomyces cerevisiae | 2 | 0.7399 |
| Kynurenine 3-monooxygenase | P38169 | KMO_YEAST | Saccharomyces cerevisiae | 2 | 0.7399 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7398 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7398 |
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 3 | 0.7396 |
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 3 | 0.7396 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 2 | 0.7382 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 2 | 0.7382 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7337 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7337 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7334 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7334 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 2 | 0.7265 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 2 | 0.7265 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7247 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7247 |
| Catechol 2,3-dioxygenase | Q6REQ5 | Q6REQ5_9NOCA | Rhodococcus sp. DK17 | 3 | 0.7234 |
| Catechol 2,3-dioxygenase | Q6REQ5 | Q6REQ5_9NOCA | Rhodococcus sp. DK17 | 3 | 0.7234 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7171 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7171 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7099 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7099 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7096 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7096 |
| rRNA methylase | Q8DSS3 | Q8DSS3_STRMU | Streptococcus mutans serotype c | 2 | 0.7091 |
| rRNA methylase | Q8DSS3 | Q8DSS3_STRMU | Streptococcus mutans serotype c | 2 | 0.7091 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7087 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7087 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7066 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7066 |
| Chorismate pyruvate-lyase | P26602 | UBIC_ECOLI | Escherichia coli | 3 | 0.7065 |
| Chorismate pyruvate-lyase | P26602 | UBIC_ECOLI | Escherichia coli | 3 | 0.7065 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7056 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7056 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7053 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7053 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7053 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7053 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7034 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7034 |
| Lactaldehyde dehydrogenase | P25553 | ALDA_ECOLI | Escherichia coli | 3 | 0.7026 |
| Lactaldehyde dehydrogenase | P25553 | ALDA_ECOLI | Escherichia coli | 3 | 0.7026 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7013 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7013 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7012 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7012 |
| L-lactate dehydrogenase | Q27743 | LDH_PLAFD | Plasmodium falciparum | 2 | 0.7006 |
| L-lactate dehydrogenase | Q27743 | LDH_PLAFD | Plasmodium falciparum | 2 | 0.7006 |