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Ajugapitin

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 4b872795-cb63-43f0-987d-41c1ae8ebcc6
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
IUPAC Name [(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(3aS,5S,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] 2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC1C(CC2C(C(CC(C2(C13CO3)COC(=O)C)OC(=O)C)C)(C)C4CC5C=COC5O4)O
SMILES (Isomeric) CCC(C)C(=O)O[C@H]1[C@@H](C[C@@H]2[C@@]([C@@H](C[C@@H]([C@]2([C@@]13CO3)COC(=O)C)OC(=O)C)C)(C)[C@@H]4C[C@H]5C=CO[C@H]5O4)O
InChI InChI=1S/C29H42O10/c1-7-15(2)25(33)39-24-20(32)12-21-27(6,22-11-19-8-9-34-26(19)38-22)16(3)10-23(37-18(5)31)28(21,13-35-17(4)30)29(24)14-36-29/h8-9,15-16,19-24,26,32H,7,10-14H2,1-6H3/t15?,16-,19-,20-,21-,22+,23+,24+,26+,27+,28+,29-/m1/s1
InChI Key LHFSTOLZQVESJD-DBNYLVSFSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C29H42O10
Molecular Weight 550.60 g/mol
Exact Mass 550.27779753 g/mol
Topological Polar Surface Area (TPSA) 130.00 Ų
XlogP 3.00
Atomic LogP (AlogP) 2.90
H-Bond Acceptor 10
H-Bond Donor 1
Rotatable Bonds 7

Synonyms

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CHEBI:67463
CHEMBL2272208
Q27135930
(1R,2S,3R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5,6-dimethyl-5-[(2S,3aS,6aS)-2,3,3a,6a-tetrahydrofuro[2,3-b]furan-2-yl]octahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylbutanoate
[(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(3aS,5S,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] 2-methylbutanoate

2D Structure

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2D Structure of Ajugapitin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9809 98.09%
Caco-2 - 0.7534 75.34%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.6991 69.91%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8359 83.59%
OATP1B3 inhibitior + 0.8863 88.63%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.9319 93.19%
P-glycoprotein inhibitior + 0.7178 71.78%
P-glycoprotein substrate + 0.6189 61.89%
CYP3A4 substrate + 0.6850 68.50%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8590 85.90%
CYP3A4 inhibition + 0.5254 52.54%
CYP2C9 inhibition - 0.7881 78.81%
CYP2C19 inhibition - 0.7968 79.68%
CYP2D6 inhibition - 0.9491 94.91%
CYP1A2 inhibition - 0.9200 92.00%
CYP2C8 inhibition + 0.5704 57.04%
CYP inhibitory promiscuity - 0.8247 82.47%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.4986 49.86%
Eye corrosion - 0.9878 98.78%
Eye irritation - 0.9137 91.37%
Skin irritation - 0.5890 58.90%
Skin corrosion - 0.9380 93.80%
Ames mutagenesis - 0.5137 51.37%
Human Ether-a-go-go-Related Gene inhibition - 0.4010 40.10%
Micronuclear - 0.5800 58.00%
Hepatotoxicity - 0.6375 63.75%
skin sensitisation - 0.8624 86.24%
Respiratory toxicity - 0.5333 53.33%
Reproductive toxicity + 0.7889 78.89%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.5153 51.53%
Acute Oral Toxicity (c) I 0.5975 59.75%
Estrogen receptor binding + 0.8511 85.11%
Androgen receptor binding + 0.7091 70.91%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.7255 72.55%
Aromatase binding + 0.7256 72.56%
PPAR gamma + 0.7288 72.88%
Honey bee toxicity - 0.7232 72.32%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5955 59.55%
Fish aquatic toxicity + 0.9913 99.13%

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 98.99% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.13% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.08% 97.25%
CHEMBL2581 P07339 Cathepsin D 95.02% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.72% 91.11%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 93.35% 98.75%
CHEMBL340 P08684 Cytochrome P450 3A4 92.41% 91.19%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 92.16% 97.21%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 91.43% 96.47%
CHEMBL2996 Q05655 Protein kinase C delta 90.47% 97.79%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.61% 97.09%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 88.62% 82.69%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 87.62% 97.14%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 86.78% 95.71%
CHEMBL2413 P32246 C-C chemokine receptor type 1 86.63% 89.50%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.41% 86.33%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 85.60% 96.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 85.42% 85.14%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.97% 94.33%
CHEMBL221 P23219 Cyclooxygenase-1 82.51% 90.17%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.85% 95.50%
CHEMBL5255 O00206 Toll-like receptor 4 81.64% 92.50%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 81.34% 89.05%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.84% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.33% 91.07%

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 australis
Ajuga chamaepitys
Scutellaria lateriflora

Cross-Links

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PubChem 21123700
LOTUS LTS0110048
wikiData Q27135930