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Kahweol

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID a0eb9348-9481-447e-beca-db0545049d32
Taxonomy Organoheterocyclic compounds > Naphthofurans
IUPAC Name (1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6,10-trien-17-ol
SMILES (Canonical) CC12C=CC3=C(C1CCC45C2CCC(C4)C(C5)(CO)O)C=CO3
SMILES (Isomeric) C[C@@]12C=CC3=C([C@H]1CC[C@]45[C@H]2CC[C@H](C4)[C@](C5)(CO)O)C=CO3
InChI InChI=1S/C20H26O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1
InChI Key JEKMKNDURXDJAD-HWUKTEKMSA-N
Popularity 139 references in papers

Physical and Chemical Properties

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Molecular Formula C20H26O3
Molecular Weight 314.40 g/mol
Exact Mass 314.18819469 g/mol
Topological Polar Surface Area (TPSA) 53.60 Ų
XlogP 3.40
Atomic LogP (AlogP) 3.72
H-Bond Acceptor 3
H-Bond Donor 2
Rotatable Bonds 1

Synonyms

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6894-43-5
CCRIS 1521
KX95B6688Y
(3bS,5aS,7R,8R,10aR,10bS)-7-(hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b-decahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol
5a,8-Methano-5aH-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b-decahydro-7-hydroxy-10b-methyl-, (3bS,5aS,7R,8R,10aR,10bS)-
5a,8-Methano-5aH-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b-decahydro-7-hydroxy-10b-methyl-, (3bS-(3balpha,5abeta,7beta,8beta,10aalpha,10bbeta))-
5a,8-Methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b-decahydro-7-hydroxy-10b-methyl-, (3bS,5aS,7R,8R,10aR,10bS)-
5a,8-Methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b-decahydro-7-hydroxy-10b-methyl-, [3bS-(3balpha,5abeta,7beta,8beta,10aalpha,10bbeta)]-
SCHEMBL237066
UNII-KX95B6688Y
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Kahweol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9912 99.12%
Caco-2 - 0.5154 51.54%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.6393 63.93%
OATP2B1 inhibitior - 0.8661 86.61%
OATP1B1 inhibitior + 0.8931 89.31%
OATP1B3 inhibitior + 0.9576 95.76%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.7292 72.92%
BSEP inhibitior - 0.5723 57.23%
P-glycoprotein inhibitior - 0.8808 88.08%
P-glycoprotein substrate - 0.5874 58.74%
CYP3A4 substrate + 0.6481 64.81%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7979 79.79%
CYP3A4 inhibition - 0.8531 85.31%
CYP2C9 inhibition - 0.7707 77.07%
CYP2C19 inhibition - 0.5305 53.05%
CYP2D6 inhibition - 0.9048 90.48%
CYP1A2 inhibition - 0.7646 76.46%
CYP2C8 inhibition + 0.5203 52.03%
CYP inhibitory promiscuity - 0.7757 77.57%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.8700 87.00%
Carcinogenicity (trinary) Non-required 0.5441 54.41%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9863 98.63%
Skin irritation - 0.7132 71.32%
Skin corrosion - 0.9389 93.89%
Ames mutagenesis - 0.8070 80.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7343 73.43%
Micronuclear - 0.8500 85.00%
Hepatotoxicity - 0.5750 57.50%
skin sensitisation - 0.7889 78.89%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity - 0.7735 77.35%
Acute Oral Toxicity (c) III 0.5575 55.75%
Estrogen receptor binding + 0.9259 92.59%
Androgen receptor binding + 0.6794 67.94%
Thyroid receptor binding + 0.6916 69.16%
Glucocorticoid receptor binding + 0.8064 80.64%
Aromatase binding + 0.6910 69.10%
PPAR gamma + 0.5858 58.58%
Honey bee toxicity - 0.8993 89.93%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.9037 90.37%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.37% 91.11%
CHEMBL240 Q12809 HERG 96.94% 89.76%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.64% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.11% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.60% 97.09%
CHEMBL2815 P04629 Nerve growth factor receptor Trk-A 90.00% 87.16%
CHEMBL3492 P49721 Proteasome Macropain subunit 89.53% 90.24%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.33% 95.89%
CHEMBL4208 P20618 Proteasome component C5 87.98% 90.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 87.44% 92.62%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.55% 100.00%
CHEMBL2581 P07339 Cathepsin D 84.61% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.18% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.09% 86.33%
CHEMBL221 P23219 Cyclooxygenase-1 81.21% 90.17%

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.
Coffea arabica
Coffea racemosa

Cross-Links

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PubChem 114778
LOTUS LTS0008811
wikiData Q1721243