[(1R,2S,3R,4R,4aS,8aR)-3-hydroxy-3,4,8,8a-tetramethyl-1-(3-methyl-2-oxobutanoyl)oxy-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-2,4a,5,6-tetrahydro-1H-naphthalen-2-yl] pyridine-3-carboxylate

Details

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Internal ID 1d2de994-72e0-4e49-a093-4720a52e7fa5
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name [(1R,2S,3R,4R,4aS,8aR)-3-hydroxy-3,4,8,8a-tetramethyl-1-(3-methyl-2-oxobutanoyl)oxy-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-2,4a,5,6-tetrahydro-1H-naphthalen-2-yl] pyridine-3-carboxylate
SMILES (Canonical) CC1=CCCC2C1(C(C(C(C2(C)C=CC3=CC(=O)OC3)(C)O)OC(=O)C4=CN=CC=C4)OC(=O)C(=O)C(C)C)C
SMILES (Isomeric) CC1=CCC[C@H]2[C@]1([C@H]([C@@H]([C@]([C@]2(C)/C=C/C3=CC(=O)OC3)(C)O)OC(=O)C4=CN=CC=C4)OC(=O)C(=O)C(C)C)C
InChI InChI=1S/C31H37NO8/c1-18(2)24(34)28(36)39-25-26(40-27(35)21-10-8-14-32-16-21)31(6,37)29(4,13-12-20-15-23(33)38-17-20)22-11-7-9-19(3)30(22,25)5/h8-10,12-16,18,22,25-26,37H,7,11,17H2,1-6H3/b13-12+/t22-,25+,26+,29-,30+,31+/m1/s1
InChI Key HIVFEOLTCPRWLR-QIDHMWRMSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C31H37NO8
Molecular Weight 551.60 g/mol
Exact Mass 551.25191714 g/mol
Topological Polar Surface Area (TPSA) 129.00 Ų
XlogP 4.00
Atomic LogP (AlogP) 3.92
H-Bond Acceptor 9
H-Bond Donor 1
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1R,2S,3R,4R,4aS,8aR)-3-hydroxy-3,4,8,8a-tetramethyl-1-(3-methyl-2-oxobutanoyl)oxy-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-2,4a,5,6-tetrahydro-1H-naphthalen-2-yl] pyridine-3-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9552 95.52%
Caco-2 - 0.7524 75.24%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.8003 80.03%
OATP2B1 inhibitior - 0.8587 85.87%
OATP1B1 inhibitior + 0.8779 87.79%
OATP1B3 inhibitior + 0.8851 88.51%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior + 0.9794 97.94%
P-glycoprotein inhibitior + 0.8961 89.61%
P-glycoprotein substrate + 0.5619 56.19%
CYP3A4 substrate + 0.6849 68.49%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9081 90.81%
CYP3A4 inhibition - 0.5206 52.06%
CYP2C9 inhibition - 0.6582 65.82%
CYP2C19 inhibition - 0.6675 66.75%
CYP2D6 inhibition - 0.8539 85.39%
CYP1A2 inhibition + 0.6469 64.69%
CYP2C8 inhibition + 0.8180 81.80%
CYP inhibitory promiscuity + 0.5702 57.02%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4426 44.26%
Eye corrosion - 0.9884 98.84%
Eye irritation - 0.9226 92.26%
Skin irritation - 0.7042 70.42%
Skin corrosion - 0.9171 91.71%
Ames mutagenesis - 0.5826 58.26%
Human Ether-a-go-go-Related Gene inhibition - 0.3964 39.64%
Micronuclear - 0.6300 63.00%
Hepatotoxicity + 0.6324 63.24%
skin sensitisation - 0.7839 78.39%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.5812 58.12%
Acute Oral Toxicity (c) III 0.5752 57.52%
Estrogen receptor binding + 0.7671 76.71%
Androgen receptor binding + 0.7237 72.37%
Thyroid receptor binding + 0.6796 67.96%
Glucocorticoid receptor binding + 0.8135 81.35%
Aromatase binding + 0.6462 64.62%
PPAR gamma + 0.6991 69.91%
Honey bee toxicity - 0.7717 77.17%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 0.9170 91.70%

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
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.30% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 95.58% 99.23%
CHEMBL4224 P49759 Dual specificty protein kinase CLK1 94.56% 85.30%
CHEMBL2581 P07339 Cathepsin D 93.30% 98.95%
CHEMBL2535 P11166 Glucose transporter 92.28% 98.75%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.98% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.40% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 89.85% 91.07%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.63% 94.45%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 89.58% 98.75%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.03% 96.00%
CHEMBL3310 Q96DB2 Histone deacetylase 11 87.16% 88.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.70% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.65% 97.09%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 86.58% 95.71%
CHEMBL2996 Q05655 Protein kinase C delta 86.57% 97.79%
CHEMBL5028 O14672 ADAM10 85.30% 97.50%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 84.41% 94.80%
CHEMBL3524 P56524 Histone deacetylase 4 83.66% 92.97%
CHEMBL253 P34972 Cannabinoid CB2 receptor 83.62% 97.25%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.79% 95.89%
CHEMBL1951 P21397 Monoamine oxidase A 82.62% 91.49%
CHEMBL4208 P20618 Proteasome component C5 82.61% 90.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 82.07% 96.09%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.20% 97.33%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 81.05% 83.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.70% 93.56%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.60% 92.62%

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.
Scutellaria barbata

Cross-Links

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PubChem 44557017
NPASS NPC228331
ChEMBL CHEMBL1078660
LOTUS LTS0182334
wikiData Q105029044