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(-)-Cubebinin

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 08a8e3b7-5a60-4838-afb9-26dfe2f9a7c2
Taxonomy Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans > Dibenzylbutyrolactols
IUPAC Name (3R,4R)-3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol
SMILES (Canonical) COC1=CC(=CC(=C1OC)OC)CC2COC(C2CC3=CC(=C(C(=C3)OC)OC)OC)O
SMILES (Isomeric) COC1=CC(=CC(=C1OC)OC)C[C@H]2COC([C@@H]2CC3=CC(=C(C(=C3)OC)OC)OC)O
InChI InChI=1S/C24H32O8/c1-26-18-9-14(10-19(27-2)22(18)30-5)7-16-13-32-24(25)17(16)8-15-11-20(28-3)23(31-6)21(12-15)29-4/h9-12,16-17,24-25H,7-8,13H2,1-6H3/t16-,17+,24?/m0/s1
InChI Key PIYHDSUVUSVLGU-HSQXHLSASA-N
Popularity 3 references in papers

Physical and Chemical Properties

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Molecular Formula C24H32O8
Molecular Weight 448.50 g/mol
Exact Mass 448.20971797 g/mol
Topological Polar Surface Area (TPSA) 84.80 Ų
XlogP 3.60
Atomic LogP (AlogP) 3.10
H-Bond Acceptor 8
H-Bond Donor 1
Rotatable Bonds 10

Synonyms

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CHEMBL480296
(?)-Cubebinin
D02HSP
BDBM50259873
(3r,4r)-3,4-bis-(3,4,5-trimethoxybenzyl)tetra-hydro-2-furanol

2D Structure

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2D Structure of (-)-Cubebinin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9346 93.46%
Caco-2 + 0.6454 64.54%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.8578 85.78%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9373 93.73%
OATP1B3 inhibitior + 0.9311 93.11%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior + 0.9477 94.77%
P-glycoprotein inhibitior + 0.7885 78.85%
P-glycoprotein substrate - 0.7450 74.50%
CYP3A4 substrate + 0.5363 53.63%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.6702 67.02%
CYP3A4 inhibition + 0.7762 77.62%
CYP2C9 inhibition + 0.8042 80.42%
CYP2C19 inhibition + 0.8587 85.87%
CYP2D6 inhibition - 0.8945 89.45%
CYP1A2 inhibition + 0.8171 81.71%
CYP2C8 inhibition + 0.5491 54.91%
CYP inhibitory promiscuity + 0.8618 86.18%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9200 92.00%
Carcinogenicity (trinary) Non-required 0.5833 58.33%
Eye corrosion - 0.9880 98.80%
Eye irritation - 0.8620 86.20%
Skin irritation - 0.8550 85.50%
Skin corrosion - 0.9745 97.45%
Ames mutagenesis + 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7632 76.32%
Micronuclear + 0.5233 52.33%
Hepatotoxicity - 0.6125 61.25%
skin sensitisation - 0.8519 85.19%
Respiratory toxicity - 0.5889 58.89%
Reproductive toxicity + 0.6556 65.56%
Mitochondrial toxicity - 0.5500 55.00%
Nephrotoxicity - 0.8563 85.63%
Acute Oral Toxicity (c) III 0.5771 57.71%
Estrogen receptor binding + 0.7967 79.67%
Androgen receptor binding + 0.5232 52.32%
Thyroid receptor binding + 0.6262 62.62%
Glucocorticoid receptor binding + 0.7643 76.43%
Aromatase binding - 0.5489 54.89%
PPAR gamma + 0.6792 67.92%
Honey bee toxicity - 0.8537 85.37%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5549 55.49%
Fish aquatic toxicity + 0.9872 98.72%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL340 P08684 Cytochrome P450 3A4 15000 nM
 IC50
 PMID: 15679319

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.90% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.98% 91.11%
CHEMBL3060 Q9Y345 Glycine transporter 2 91.15% 99.17%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 90.82% 92.62%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.15% 94.45%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.61% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.21% 86.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.00% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.66% 97.14%
CHEMBL2581 P07339 Cathepsin D 83.57% 98.95%
CHEMBL4040 P28482 MAP kinase ERK2 83.04% 83.82%
CHEMBL4208 P20618 Proteasome component C5 82.15% 90.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.07% 90.71%

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.
Piper cubeba

Cross-Links

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PubChem 44575401
NPASS NPC236522
ChEMBL CHEMBL480296
LOTUS LTS0103549
wikiData Q104399137