A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.
ChEBI ID: 26013
| Member | Definition | Class |
|---|---|---|
| 2-acetamido-2-deoxy-d-glucono-(1,5)-lactone | A deoxygluconolactone that results from the cyclisation and formal condensation of the carboxy group of 2-amino-2-deoxy-D-gluconic acid with its 5-hydroxy group. It is a sex pheromone found in the urine of female blue crabs, Callinectes sapidus. | N-acetyl-D-glucosamino-1,5-lactone |
| 2-heptanone | A dialkyl ketone with methyl and pentyl as the alkyl groups. | heptan-2-one |
| 2-isobutyl-1,3-thiazole | A 1,3-thiazole in which the hydrogen at position 2 has been replaced by an isobutyl group. A food flavour component with a green note that adds the characteristics of ripe tomatoes. Used in blackcurrent, papaya, melon, raspberry, and roast beef flavours, it also enhances the flavour of fresh lime. | 2-isobutylthiazole |
| 2-nonanol | A secondary alcohol that is nonane substituted by a hydroxy group at position 2. | nonan-2-ol |
| 2-undecanol | A secondary alcohol that is undecane substituted by a hydroxy group at position 2. | undecan-2-ol |
| 2,3,5-trimethylpyrazine | A member of the class of pyrazines that is pyrazine in which three hydrogens at positions 2, 3 and 5 have been replaced by methyl groups. | trimethylpyrazine |
| 3-hydroxy-3-methylbutene | A tertiary alcohol that is 3-methylbut-1-ene carrying a hydroxy substituent at position 3. | 3-hydroxy-3-methylbut-1-ene |
| 3-hydroxybutyric acid | The R-enantiomer of 3-hydroxybutyric acid. Involved in the synthesis and degradation of ketone bodies, it can be used as an energy source by the brain during hypoglycaemia, and for the synthesis of biodegradable plastics. It is a sex pheremone in the European spider Linyphia triangularis. | (R)-3-hydroxybutyric acid |
| 4-vinylguaiacol | A member of the class of phenols that is guaiacol in which the hydrogen para- to the hydroxy group is replaced by a vinyl group. | 2-methoxy-4-vinylphenol |
| actinidine | A member of the class of cyclopentapyridines that is 6,7-dihydrocyclopenta[c]pyridine bearing two methyl substituents at positions 4 and 7. | actinidine |
| androst-16-en-3-ol | 5alpha-androst-16-en-3alpha-ol | |
| androst-16-en-3-one | An androstanoid that is 5alpha-androst-16-ene substituted by an oxo group at position 3. It is a steroid pheromone found in high concentrations in the saliva of male pigs,. | 5alpha-androst-16-en-3-one |
| androsterone | An androstanoid that is 5alpha-androstane having a hydroxy substituent at the 3alpha-position and an oxo group at the 17-position. It is a metabolite of dehydroepiandrosterone . | androsterone |
| ascr#3 | An (omega-1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,8R)-8-hydroxynon-2-enoic acid with ascarylopyranose (the alpha anomer). It is a major component of the dauer pheromone, used by the nematode Caenorhabditis elegans as a population-density signal to promote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause, and also synergises with ascr#2, ascr#4, and ascr#8 in male attraction. | ascr#3 |
| ascr#5 | An omega-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 3-hydroxypropanoic acid with ascarylopyranose (the alpha anomer). A major component of the dauer pheromone of the nematode Caenorhabditis elegans, it synergises with ascr#2 and ascr#3 as a population-density signal to promote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause. | ascr#5 |
| benzyl cyanide | A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a phenyl group. | phenylacetonitrile |
| bombykol | bombykol | |
| civetone | A macrocycle that is cycloheptadecanone with an unsaturation at position 9 (the 9Z-stereoisomer). It has been found in African Civets. | civetone |
| coniferyl alcohol | A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring. | coniferol |
| decaprenoic acid | A polyunsaturated fatty acid that is octa-2,6-dienoic acid bearing two methyl substituents at positions 3 and 7 (the 2E-isomer). | geranic acid |
| dodecanol | A primary alcohol that is dodecane in which a hydrogen from one of the methyl groups is replaced by a hydroxy group. It is registered for use in apple and pear orchards as a Lepidopteran pheromone/sex attractant, used to disrupt the mating behaviour of certain moths whose larvae destroy crops. | dodecan-1-ol |
| felinine | A cysteine thioether that is the S-(4-hydroxy-2-methylbutan-2-yl) derivative of L-cysteine. It is a major component of the urine of the domestic cat. | felinine zwitterion; felinine |
| myristyl alcohol | A long-chain fatty alcohol that is tetradecane substituted by a hydroxy group at position 1. | tetradecan-1-ol |
| n-decyl alcohol | A fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of ten carbon atoms. | decan-1-ol |
| n-heneicosane | An alkane that has 21 carbons and a straight-chain structure. It has been isolated from plants like Periploca laevigata and Carthamus tinctorius. | henicosane |
| sulcatol | sulcatol |
| Timeframe | Studies, Drugs with This Role(%) | All Drugs % |
|---|---|---|
| pre-1990 | 1,596 (51.80) | 18.7374 |
| 1990's | 239 (7.76) | 18.2507 |
| 2000's | 499 (16.20) | 29.6817 |
| 2010's | 619 (20.09) | 24.3611 |
| 2020's | 128 (4.15) | 2.80 |
| Publication Type | Studies, Drugs with this Role (%) | All Drugs (%) |
|---|---|---|
| Trials | 73 (2.18%) | 5.53% |
| Reviews | 76 (2.27%) | 6.00% |
| Case Studies | 43 (1.28%) | 4.05% |
| Observational | 3 (0.09%) | 0.25% |
| Other | 3,154 (94.18%) | 84.16% |
| Protein | Taxonomy | Measurement | Average (mM) | Bioassay(s) | Drugs |
|---|---|---|---|---|---|
| acetylcholinesterase | Homo sapiens (human) | Potency | 39.9149 | 1 | 1 |
| activating transcription factor 6 | Homo sapiens (human) | Potency | 24.9288 | 2 | 2 |
| AR protein | Homo sapiens (human) | Potency | 29.6818 | 4 | 5 |
| aryl hydrocarbon receptor | Homo sapiens (human) | Potency | 19.5673 | 1 | 1 |
| ATAD5 protein, partial | Homo sapiens (human) | Potency | 18.3489 | 1 | 1 |
| bromodomain adjacent to zinc finger domain 2B | Homo sapiens (human) | Potency | 100.0000 | 1 | 1 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 2.4386 | 1 | 1 |
| Chain A, 2-oxoglutarate Oxygenase | Homo sapiens (human) | Potency | 14.0947 | 1 | 2 |
| Chain A, Beta-lactamase | Escherichia coli K-12 | Potency | 14.3484 | 1 | 2 |
| chromobox protein homolog 1 | Homo sapiens (human) | Potency | 97.2813 | 1 | 4 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 25.9078 | 1 | 2 |
| DNA polymerase iota isoform a (long) | Homo sapiens (human) | Potency | 79.9598 | 1 | 2 |
| DNA polymerase kappa isoform 1 | Homo sapiens (human) | Potency | 79.4328 | 1 | 1 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 29.3798 | 9 | 16 |
| estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 47.1613 | 2 | 3 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 52.8751 | 6 | 12 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 9.3965 | 2 | 3 |
| geminin | Homo sapiens (human) | Potency | 29.0196 | 2 | 2 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 30.7823 | 3 | 10 |
| Glutamate receptor 2 | Rattus norvegicus (Norway rat) | Potency | 61.1732 | 1 | 3 |
| Guanine nucleotide-binding protein G | Homo sapiens (human) | Potency | 33.7272 | 1 | 2 |
| heat shock protein beta-1 | Homo sapiens (human) | Potency | 39.0234 | 2 | 2 |
| histone acetyltransferase KAT2A isoform 1 | Homo sapiens (human) | Potency | 20.2676 | 1 | 2 |
| Histone H2A.x | Cricetulus griseus (Chinese hamster) | Potency | 113.0040 | 1 | 2 |
| Luciferase | Photinus pyralis (common eastern firefly) | Potency | 27.7187 | 1 | 4 |
| Microtubule-associated protein tau | Homo sapiens (human) | Potency | 22.3872 | 1 | 1 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 46.8268 | 2 | 2 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 44.6684 | 1 | 1 |
| peroxisome proliferator-activated receptor delta | Homo sapiens (human) | Potency | 15.6817 | 1 | 1 |
| potassium voltage-gated channel subfamily H member 2 isoform d | Homo sapiens (human) | Potency | 25.1189 | 1 | 1 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 397.5238 | 2 | 4 |
| pregnane X receptor | Rattus norvegicus (Norway rat) | Potency | 70.7946 | 1 | 1 |
| progesterone receptor | Homo sapiens (human) | Potency | 52.1701 | 1 | 3 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 19.0998 | 2 | 3 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 42.7293 | 2 | 17 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 35.1749 | 2 | 8 |
| serine-protein kinase ATM isoform a | Homo sapiens (human) | Potency | 39.8107 | 1 | 1 |
| TAR DNA-binding protein 43 | Homo sapiens (human) | Potency | 17.7828 | 1 | 1 |
| TDP1 protein | Homo sapiens (human) | Potency | 26.1011 | 1 | 2 |
| thioredoxin glutathione reductase | Schistosoma mansoni | Potency | 56.2341 | 1 | 2 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 33.4915 | 1 | 1 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 48.9662 | 1 | 1 |
| vitamin D (1,25- dihydroxyvitamin D3) receptor | Homo sapiens (human) | Potency | 3.2383 | 1 | 1 |
| Voltage-dependent calcium channel gamma-2 subunit | Mus musculus (house mouse) | Potency | 61.1732 | 1 | 3 |
| Protein | Taxonomy | Measurement | Average (mM) | Bioassay(s) | Drugs |
|---|---|---|---|---|---|
| Androgen receptor | Rattus norvegicus (Norway rat) | IC50 | 40.7380 | 1 | 1 |
| Chain A, Hyaluronoglucosaminidase | Oceanicola granulosus HTCC2516 | IC50 | 11.0000 | 1 | 1 |
| Chain A, retinol dehydratase | Spodoptera frugiperda (fall armyworm) | Ki | 0.1100 | 1 | 1 |
| Corticosteroid-binding globulin | Homo sapiens (human) | Ki | 2.4547 | 1 | 1 |
| GABA theta subunit | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit alpha-1 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit alpha-2 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit alpha-3 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit alpha-4 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit alpha-5 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit alpha-6 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit beta-1 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit beta-2 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit beta-3 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit delta | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit epsilon | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit gamma-1 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit gamma-2 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit gamma-3 | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Gamma-aminobutyric acid receptor subunit pi | Rattus norvegicus (Norway rat) | IC50 | 1.3670 | 1 | 1 |
| Glucose-6-phosphate 1-dehydrogenase | Homo sapiens (human) | IC50 | 200.0000 | 1 | 1 |
| Nuclear receptor subfamily 1 group I member 3 | Mus musculus (house mouse) | IC50 | 0.2500 | 1 | 1 |
| Phenylethanolamine N-methyltransferase | Bos taurus (cattle) | IC50 | 669.0000 | 1 | 1 |
| Solute carrier family 22 member 20 | Mus musculus (house mouse) | Ki | 190.5460 | 1 | 1 |
| Solute carrier family 22 member 6 | Mus musculus (house mouse) | Ki | 3,235.9400 | 1 | 1 |
| Solute carrier organic anion transporter family member 1A1 | Rattus norvegicus (Norway rat) | Ki | 10.6000 | 1 | 1 |
| Protein | Taxonomy | Measurement | Average (mM) | Bioassay(s) | Drugs |
|---|---|---|---|---|---|
| G-protein coupled bile acid receptor 1 | Homo sapiens (human) | EC50 | 6.2200 | 1 | 1 |
| Sex hormone-binding globulin | Homo sapiens (human) | Kd | 0.0708 | 1 | 1 |
| Transient receptor potential cation channel subfamily A member 1 | Homo sapiens (human) | EC50 | 82.8000 | 1 | 1 |
| Protein | Taxonomy | Measurement | Average (mM) | Bioassay(s) | Drugs |
|---|---|---|---|---|---|
| Monocarboxylate transporter 4 | Homo sapiens (human) | Km | 130,000.0000 | 1 | 1 |