Geosmin

Details

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Internal ID ada8a964-86b7-4dc5-9260-e1f0e06d7f41
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Tertiary alcohols
IUPAC Name (4S,4aS,8aR)-4,8a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol
SMILES (Canonical) CC1CCCC2(C1(CCCC2)O)C
SMILES (Isomeric) C[C@H]1CCC[C@@]2([C@@]1(CCCC2)O)C
InChI InChI=1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3/t10-,11+,12-/m0/s1
InChI Key JLPUXFOGCDVKGO-TUAOUCFPSA-N
Popularity 1,101 references in papers

Physical and Chemical Properties

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Molecular Formula C12H22O
Molecular Weight 182.30 g/mol
Exact Mass 182.167065321 g/mol
Topological Polar Surface Area (TPSA) 20.20 Ų
XlogP 3.30
Atomic LogP (AlogP) 3.12
H-Bond Acceptor 1
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

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19700-21-1
(-)-geosmin
Octahydro-4alpha,8abeta-dimethyl-4aalpha(2H)-naphthol
MYW912WXJ4
CHEBI:46702
trans-1,10-dimethyl-trans-decalol
(4S-(4alpha,4aalpha,8abeta))-Octahydro-4,8a-dimethyl-4a(2H)-naphthol
(4S,4aS,8aR)-4,8a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol
trans-1,10-Dimethyl-trans-9-decalol
(4S,4aS,8aR)-4,8a-dimethyloctahydronaphthalen-4a(2H)-ol
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Geosmin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9967 99.67%
Caco-2 + 0.8423 84.23%
Blood Brain Barrier + 0.8250 82.50%
Human oral bioavailability + 0.6286 62.86%
Subcellular localzation Lysosomes 0.5197 51.97%
OATP2B1 inhibitior - 0.8430 84.30%
OATP1B1 inhibitior + 0.9502 95.02%
OATP1B3 inhibitior + 0.9685 96.85%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.5750 57.50%
BSEP inhibitior - 0.8746 87.46%
P-glycoprotein inhibitior - 0.9753 97.53%
P-glycoprotein substrate - 0.9406 94.06%
CYP3A4 substrate - 0.5563 55.63%
CYP2C9 substrate + 0.6248 62.48%
CYP2D6 substrate - 0.7422 74.22%
CYP3A4 inhibition - 0.8497 84.97%
CYP2C9 inhibition - 0.8038 80.38%
CYP2C19 inhibition - 0.8379 83.79%
CYP2D6 inhibition - 0.9640 96.40%
CYP1A2 inhibition - 0.5507 55.07%
CYP2C8 inhibition - 0.9520 95.20%
CYP inhibitory promiscuity - 0.9491 94.91%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.8500 85.00%
Carcinogenicity (trinary) Non-required 0.5859 58.59%
Eye corrosion - 0.9560 95.60%
Eye irritation + 0.8682 86.82%
Skin irritation + 0.6869 68.69%
Skin corrosion - 0.7837 78.37%
Ames mutagenesis - 0.9900 99.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6408 64.08%
Micronuclear - 0.9800 98.00%
Hepatotoxicity + 0.5357 53.57%
skin sensitisation + 0.5963 59.63%
Respiratory toxicity - 0.6889 68.89%
Reproductive toxicity + 0.8308 83.08%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity - 0.6997 69.97%
Acute Oral Toxicity (c) III 0.8654 86.54%
Estrogen receptor binding - 0.8448 84.48%
Androgen receptor binding - 0.6782 67.82%
Thyroid receptor binding - 0.8127 81.27%
Glucocorticoid receptor binding - 0.8991 89.91%
Aromatase binding - 0.7714 77.14%
PPAR gamma - 0.8542 85.42%
Honey bee toxicity - 0.9468 94.68%
Biodegradation - 0.6250 62.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9359 93.59%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.46% 97.25%
CHEMBL4040 P28482 MAP kinase ERK2 93.74% 83.82%
CHEMBL206 P03372 Estrogen receptor alpha 90.06% 97.64%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.81% 96.09%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.26% 82.69%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 85.11% 91.11%
CHEMBL218 P21554 Cannabinoid CB1 receptor 84.67% 96.61%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.60% 97.09%
CHEMBL1907601 P11802 Cyclin-dependent kinase 4/cyclin D1 82.09% 98.99%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 81.56% 89.05%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 81.52% 95.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.86% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.72% 95.89%
CHEMBL1902 P62942 FK506-binding protein 1A 80.16% 97.05%
CHEMBL238 Q01959 Dopamine transporter 80.09% 95.88%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.00% 92.94%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Basella alba
Beta vulgaris
Coffea arabica
Phaseolus vulgaris
Symphyogyna brongniartii
Zea mays

Cross-Links

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PubChem 29746
LOTUS LTS0091389
wikiData Q420233