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Aucubigenin

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 4a882ea1-964b-48f2-ab13-f17fdb0c5a36
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
IUPAC Name (1R,4aR,5S,7aS)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1,5-diol
SMILES (Canonical) C1=COC(C2C1C(C=C2CO)O)O
SMILES (Isomeric) C1=CO[C@H]([C@H]2[C@@H]1[C@@H](C=C2CO)O)O
InChI InChI=1S/C9H12O4/c10-4-5-3-7(11)6-1-2-13-9(12)8(5)6/h1-3,6-12H,4H2/t6-,7+,8+,9+/m0/s1
InChI Key BACWCXKATFIVFS-JQCXWYLXSA-N
Popularity 7 references in papers

Physical and Chemical Properties

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Molecular Formula C9H12O4
Molecular Weight 184.19 g/mol
Exact Mass 184.07355886 g/mol
Topological Polar Surface Area (TPSA) 69.90 Ų
XlogP -1.40
Atomic LogP (AlogP) -0.63
H-Bond Acceptor 4
H-Bond Donor 3
Rotatable Bonds 1

Synonyms

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64274-28-8
Aucubin aglycon
Cyclopenta(c)pyran-1,5-diol, 1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, (1R-(1alpha,4aalpha,5alpha,7aalpha))-
(1r,4ar,5s,7as)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1,5-diol
Aucubigenin (Aucubin aglycon)
DTXSID30214496
AKOS040750632

2D Structure

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2D Structure of Aucubigenin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9287 92.87%
Caco-2 - 0.6107 61.07%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability + 0.5857 58.57%
Subcellular localzation Mitochondria 0.4903 49.03%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8795 87.95%
OATP1B3 inhibitior + 0.9607 96.07%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.9761 97.61%
P-glycoprotein inhibitior - 0.9791 97.91%
P-glycoprotein substrate - 0.9137 91.37%
CYP3A4 substrate - 0.6205 62.05%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8007 80.07%
CYP3A4 inhibition - 0.7628 76.28%
CYP2C9 inhibition - 0.7863 78.63%
CYP2C19 inhibition - 0.7842 78.42%
CYP2D6 inhibition - 0.8611 86.11%
CYP1A2 inhibition - 0.6317 63.17%
CYP2C8 inhibition - 0.8666 86.66%
CYP inhibitory promiscuity - 0.6208 62.08%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9130 91.30%
Carcinogenicity (trinary) Non-required 0.6292 62.92%
Eye corrosion - 0.9404 94.04%
Eye irritation - 0.6496 64.96%
Skin irritation - 0.6227 62.27%
Skin corrosion - 0.8992 89.92%
Ames mutagenesis + 0.5263 52.63%
Human Ether-a-go-go-Related Gene inhibition - 0.7190 71.90%
Micronuclear - 0.6200 62.00%
Hepatotoxicity - 0.5375 53.75%
skin sensitisation - 0.7622 76.22%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity - 0.5000 50.00%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity + 0.4785 47.85%
Acute Oral Toxicity (c) III 0.4306 43.06%
Estrogen receptor binding - 0.8589 85.89%
Androgen receptor binding - 0.8053 80.53%
Thyroid receptor binding - 0.7716 77.16%
Glucocorticoid receptor binding - 0.8169 81.69%
Aromatase binding - 0.8400 84.00%
PPAR gamma - 0.7425 74.25%
Honey bee toxicity - 0.9161 91.61%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.7000 70.00%
Fish aquatic toxicity - 0.5824 58.24%

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 92.47% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.74% 96.09%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 86.25% 86.92%
CHEMBL226 P30542 Adenosine A1 receptor 84.77% 95.93%

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.
Aucuba japonica
Scrophularia nodosa

Cross-Links

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PubChem 163040
NPASS NPC154216
LOTUS LTS0144186
wikiData Q83090354