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Ajugachin B

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 149f1ce2-f597-4be7-9c64-446523e81869
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
IUPAC Name 1-O-[(4aR,5S,6R,8S,8aR)-5-[(3aS,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetyloxy-8a-(acetyloxymethyl)-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] 4-O-methyl (2R,3S)-2-hydroxy-2,3-dimethylbutanedioate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C31H44O12/c1-16-12-24(41-19(4)33)30(14-39-18(3)32)21(28(16,5)23-13-20-10-11-38-26(20)42-23)8-9-22(31(30)15-40-31)43-27(35)29(6,36)17(2)25(34)37-7/h10-11,16-17,20-24,26,36H,8-9,12-15H2,1-7H3/t16-,17-,20-,21-,22?,23?,24+,26+,28+,29-,30+,31?/m1/s1
InChI Key HDHVWHCGGUJHQA-VRBSUYBLSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C31H44O12
Molecular Weight 608.70 g/mol
Exact Mass 608.28327683 g/mol
Topological Polar Surface Area (TPSA) 156.00 Ų
XlogP 2.50
Atomic LogP (AlogP) 2.44
H-Bond Acceptor 12
H-Bond Donor 1
Rotatable Bonds 8

Synonyms

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131086-65-2
(-)-Ajugachin B
DTXSID70927073
1-[8-(Acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-5-(2,3,3a,6a-tetrahydrofuro[2,3-b]furan-2-yl)octahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl] 4-methyl 2-hydroxy-2,3-dimethylbutanedioate
Butanedioic acid, 2,3-dimethyl-, (1R,2S,3R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-((acetyloxy)methyl)octahydro-3-hydroxy-5,6-dimethyl-5-((2S,3aS,6aS)-2,3,3a,6a-tetrahydrofuro(2,3-b)furan-2-yl)spiro(naphthalene-1(2H),2'-oxiran)-2-yl methyl ester
Butanedioic acid, 2,3-dimethyl-, 8-(acetyloxy)-8a-((acetyloxy)methyl)octahydro-3-hydroxy-5,6-dimethyl-5-(2,3,3a,6a-tetrahydrofuro(2,3-b)furan-2-yl)spiro(naphthalene-1(2H),2'-oxiran)-2-yl methyl ester, (1R-(1alpha,2beta,3alpha,4abeta,5beta(2S*,3aS*,6aS*),6alpha,8alpha,8aalpha))-(partial)-

2D Structure

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2D Structure of Ajugachin B

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9677 96.77%
Caco-2 - 0.8010 80.10%
Blood Brain Barrier + 0.7750 77.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7762 77.62%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8443 84.43%
OATP1B3 inhibitior + 0.9212 92.12%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior + 0.9667 96.67%
P-glycoprotein inhibitior + 0.8015 80.15%
P-glycoprotein substrate + 0.7089 70.89%
CYP3A4 substrate + 0.7215 72.15%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8681 86.81%
CYP3A4 inhibition - 0.7346 73.46%
CYP2C9 inhibition - 0.8378 83.78%
CYP2C19 inhibition - 0.8780 87.80%
CYP2D6 inhibition - 0.9565 95.65%
CYP1A2 inhibition - 0.9374 93.74%
CYP2C8 inhibition + 0.7301 73.01%
CYP inhibitory promiscuity - 0.9188 91.88%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4911 49.11%
Eye corrosion - 0.9873 98.73%
Eye irritation - 0.9184 91.84%
Skin irritation - 0.6896 68.96%
Skin corrosion - 0.9364 93.64%
Ames mutagenesis - 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4113 41.13%
Micronuclear - 0.6100 61.00%
Hepatotoxicity - 0.6288 62.88%
skin sensitisation - 0.8906 89.06%
Respiratory toxicity - 0.5444 54.44%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity + 0.5317 53.17%
Acute Oral Toxicity (c) I 0.5922 59.22%
Estrogen receptor binding + 0.7775 77.75%
Androgen receptor binding + 0.7033 70.33%
Thyroid receptor binding + 0.5423 54.23%
Glucocorticoid receptor binding + 0.7542 75.42%
Aromatase binding + 0.7442 74.42%
PPAR gamma + 0.7077 70.77%
Honey bee toxicity - 0.6975 69.75%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9745 97.45%

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 98.81% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.21% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.79% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.63% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.06% 91.11%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 96.02% 95.71%
CHEMBL2581 P07339 Cathepsin D 95.63% 98.95%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 93.64% 97.14%
CHEMBL340 P08684 Cytochrome P450 3A4 92.04% 91.19%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 91.39% 96.47%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 90.96% 94.33%
CHEMBL2996 Q05655 Protein kinase C delta 90.19% 97.79%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 90.06% 95.71%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.72% 97.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 87.85% 96.77%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 87.76% 92.62%
CHEMBL3922 P50579 Methionine aminopeptidase 2 87.25% 97.28%
CHEMBL2413 P32246 C-C chemokine receptor type 1 85.62% 89.50%
CHEMBL3976 Q9UHL4 Dipeptidyl peptidase II 85.14% 92.29%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 85.14% 82.69%
CHEMBL5028 O14672 ADAM10 84.86% 97.50%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 84.86% 98.75%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.66% 91.07%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.98% 86.33%
CHEMBL5255 O00206 Toll-like receptor 4 83.65% 92.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.32% 99.17%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 83.26% 100.00%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 82.71% 89.05%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.64% 95.89%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.45% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.43% 95.89%
CHEMBL3437 Q16853 Amine oxidase, copper containing 81.43% 94.00%
CHEMBL1907601 P11802 Cyclin-dependent kinase 4/cyclin D1 81.22% 98.99%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 81.22% 96.95%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.21% 96.00%

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.
Ajuga chamaepitys

Cross-Links

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PubChem 183008
LOTUS LTS0053781
wikiData Q82901693