(3R,4aS,6R,6aS,7S,10aR,10bS)-3-ethenyl-3,7-bis(hydroxymethyl)-4a,7,10a-trimethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-6-ol

Details

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Internal ID ba73abd3-fa9c-4b38-9a1d-003fa8577ee4
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (3R,4aS,6R,6aS,7S,10aR,10bS)-3-ethenyl-3,7-bis(hydroxymethyl)-4a,7,10a-trimethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-6-ol
SMILES (Canonical) CC1(CCCC2(C1C(CC3(C2CCC(O3)(CO)C=C)C)O)C)CO
SMILES (Isomeric) C[C@@]1(CCC[C@@]2([C@@H]1[C@@H](C[C@]3([C@H]2CC[C@](O3)(CO)C=C)C)O)C)CO
InChI InChI=1S/C20H34O4/c1-5-20(13-22)10-7-15-18(3)9-6-8-17(2,12-21)16(18)14(23)11-19(15,4)24-20/h5,14-16,21-23H,1,6-13H2,2-4H3/t14-,15+,16-,17-,18+,19+,20+/m1/s1
InChI Key PBTFJUXOLJJSAW-SXJNSPEGSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H34O4
Molecular Weight 338.50 g/mol
Exact Mass 338.24570956 g/mol
Topological Polar Surface Area (TPSA) 69.90 Ų
XlogP 2.50
Atomic LogP (AlogP) 2.66
H-Bond Acceptor 4
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R,4aS,6R,6aS,7S,10aR,10bS)-3-ethenyl-3,7-bis(hydroxymethyl)-4a,7,10a-trimethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-6-ol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9209 92.09%
Caco-2 + 0.5934 59.34%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.4670 46.70%
OATP2B1 inhibitior - 0.8567 85.67%
OATP1B1 inhibitior + 0.8417 84.17%
OATP1B3 inhibitior + 0.9137 91.37%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.5919 59.19%
BSEP inhibitior - 0.5890 58.90%
P-glycoprotein inhibitior - 0.8635 86.35%
P-glycoprotein substrate - 0.8055 80.55%
CYP3A4 substrate + 0.6067 60.67%
CYP2C9 substrate - 0.8030 80.30%
CYP2D6 substrate - 0.7241 72.41%
CYP3A4 inhibition - 0.7071 70.71%
CYP2C9 inhibition - 0.8860 88.60%
CYP2C19 inhibition - 0.7695 76.95%
CYP2D6 inhibition - 0.9494 94.94%
CYP1A2 inhibition - 0.8261 82.61%
CYP2C8 inhibition - 0.6776 67.76%
CYP inhibitory promiscuity - 0.9572 95.72%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.7037 70.37%
Eye corrosion - 0.9875 98.75%
Eye irritation - 0.9464 94.64%
Skin irritation - 0.7057 70.57%
Skin corrosion - 0.9569 95.69%
Ames mutagenesis - 0.7824 78.24%
Human Ether-a-go-go-Related Gene inhibition - 0.5486 54.86%
Micronuclear - 0.9500 95.00%
Hepatotoxicity - 0.7077 70.77%
skin sensitisation - 0.8658 86.58%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.7556 75.56%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.7931 79.31%
Acute Oral Toxicity (c) III 0.6173 61.73%
Estrogen receptor binding + 0.7311 73.11%
Androgen receptor binding + 0.6224 62.24%
Thyroid receptor binding + 0.5954 59.54%
Glucocorticoid receptor binding + 0.7365 73.65%
Aromatase binding + 0.7467 74.67%
PPAR gamma - 0.5554 55.54%
Honey bee toxicity - 0.7503 75.03%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.7955 79.55%

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 94.55% 91.11%
CHEMBL218 P21554 Cannabinoid CB1 receptor 94.09% 96.61%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.39% 97.25%
CHEMBL237 P41145 Kappa opioid receptor 89.75% 98.10%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.29% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.24% 97.09%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 88.88% 95.50%
CHEMBL226 P30542 Adenosine A1 receptor 88.45% 95.93%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.18% 95.89%
CHEMBL233 P35372 Mu opioid receptor 86.04% 97.93%
CHEMBL259 P32245 Melanocortin receptor 4 84.35% 95.38%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.84% 100.00%
CHEMBL325 Q13547 Histone deacetylase 1 82.85% 95.92%
CHEMBL1977 P11473 Vitamin D receptor 81.41% 99.43%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.11% 92.62%
CHEMBL1937 Q92769 Histone deacetylase 2 81.07% 94.75%
CHEMBL5555 O00767 Acyl-CoA desaturase 81.03% 97.50%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 81.01% 95.83%
CHEMBL4394 Q9NYA1 Sphingosine kinase 1 80.01% 96.03%

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.
Sideritis arborescens

Cross-Links

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PubChem 162959606
LOTUS LTS0039971
wikiData Q105205423