3a,10a-Dihydroxy-5-(hydroxymethyl)-2,10-dimethyl-7-prop-1-en-2-yl-4,6a,7,9,10,10b-hexahydrobenzo[e]azulene-3,8-dione

Details

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Internal ID 193b6824-c665-4a0a-95d8-bb1504de7a30
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Rhamnofolane and daphnane diterpenoids
IUPAC Name 3a,10a-dihydroxy-5-(hydroxymethyl)-2,10-dimethyl-7-prop-1-en-2-yl-4,6a,7,9,10,10b-hexahydrobenzo[e]azulene-3,8-dione
SMILES (Canonical) CC1CC(=O)C(C2C1(C3C=C(C(=O)C3(CC(=C2)CO)O)C)O)C(=C)C
SMILES (Isomeric) CC1CC(=O)C(C2C1(C3C=C(C(=O)C3(CC(=C2)CO)O)C)O)C(=C)C
InChI InChI=1S/C20H26O5/c1-10(2)17-14-7-13(9-21)8-19(24)16(5-11(3)18(19)23)20(14,25)12(4)6-15(17)22/h5,7,12,14,16-17,21,24-25H,1,6,8-9H2,2-4H3
InChI Key BSVMBYATENQPHV-UHFFFAOYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H26O5
Molecular Weight 346.40 g/mol
Exact Mass 346.17802393 g/mol
Topological Polar Surface Area (TPSA) 94.80 Ų
XlogP 0.50
Atomic LogP (AlogP) 1.33
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3a,10a-Dihydroxy-5-(hydroxymethyl)-2,10-dimethyl-7-prop-1-en-2-yl-4,6a,7,9,10,10b-hexahydrobenzo[e]azulene-3,8-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9578 95.78%
Caco-2 - 0.6599 65.99%
Blood Brain Barrier + 0.8106 81.06%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.5447 54.47%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8815 88.15%
OATP1B3 inhibitior + 0.9501 95.01%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.8181 81.81%
P-glycoprotein inhibitior - 0.9003 90.03%
P-glycoprotein substrate - 0.6409 64.09%
CYP3A4 substrate + 0.6182 61.82%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8892 88.92%
CYP3A4 inhibition - 0.7425 74.25%
CYP2C9 inhibition - 0.8076 80.76%
CYP2C19 inhibition - 0.8703 87.03%
CYP2D6 inhibition - 0.9343 93.43%
CYP1A2 inhibition - 0.8783 87.83%
CYP2C8 inhibition - 0.7835 78.35%
CYP inhibitory promiscuity - 0.8961 89.61%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6782 67.82%
Eye corrosion - 0.9875 98.75%
Eye irritation - 0.8963 89.63%
Skin irritation - 0.6222 62.22%
Skin corrosion - 0.9351 93.51%
Ames mutagenesis + 0.5763 57.63%
Human Ether-a-go-go-Related Gene inhibition - 0.5904 59.04%
Micronuclear - 0.7400 74.00%
Hepatotoxicity - 0.6475 64.75%
skin sensitisation - 0.7813 78.13%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.5655 56.55%
Acute Oral Toxicity (c) III 0.5659 56.59%
Estrogen receptor binding + 0.5890 58.90%
Androgen receptor binding + 0.6468 64.68%
Thyroid receptor binding + 0.5751 57.51%
Glucocorticoid receptor binding + 0.7102 71.02%
Aromatase binding - 0.5000 50.00%
PPAR gamma - 0.5622 56.22%
Honey bee toxicity - 0.8376 83.76%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.8920 89.20%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.66% 96.09%
CHEMBL2581 P07339 Cathepsin D 94.45% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.29% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.07% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.28% 95.56%
CHEMBL2996 Q05655 Protein kinase C delta 86.96% 97.79%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.52% 85.14%
CHEMBL299 P17252 Protein kinase C alpha 85.91% 98.03%
CHEMBL1902 P62942 FK506-binding protein 1A 85.01% 97.05%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.70% 100.00%
CHEMBL4794 Q8NER1 Vanilloid receptor 82.80% 98.97%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 81.04% 86.00%
CHEMBL4208 P20618 Proteasome component C5 80.89% 90.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.41% 86.33%

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.
Stellera chamaejasme

Cross-Links

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PubChem 12304152
LOTUS LTS0125554
wikiData Q104945435