Dihydrocubebin

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	09670df2-ccdb-451b-870b-fba42d475bf9
Taxonomy	Lignans, neolignans and related compounds > Dibenzylbutane lignans > Dibenzylbutanediol lignans
IUPAC Name	(2R,3R)-2,3-bis(1,3-benzodioxol-5-ylmethyl)butane-1,4-diol
SMILES (Canonical)	C1OC2=C(O1)C=C(C=C2)CC(CO)C(CC3=CC4=C(C=C3)OCO4)CO
SMILES (Isomeric)	C1OC2=C(O1)C=C(C=C2)C[C@@H](CO)[C@@H](CC3=CC4=C(C=C3)OCO4)CO
InChI	InChI=1S/C20H22O6/c21-9-15(5-13-1-3-17-19(7-13)25-11-23-17)16(10-22)6-14-2-4-18-20(8-14)26-12-24-18/h1-4,7-8,15-16,21-22H,5-6,9-12H2/t15-,16-/m0/s1
InChI Key	JKCVMTYNARDGET-HOTGVXAUSA-N
Popularity	6 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₀H₂₂O₆
Molecular Weight	358.40 g/mol
Exact Mass	358.14163842 g/mol
Topological Polar Surface Area (TPSA)	77.40 Å²
XlogP	2.90
Atomic LogP (AlogP)	2.15
H-Bond Acceptor	6
H-Bond Donor	2
Rotatable Bonds	7

Synonyms

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(-)-Dihydrocubebin

24563-03-9

(2R,3R)-2,3-bis(1,3-benzodioxol-5-ylmethyl)butane-1,4-diol

CHEMBL486597

CHEBI:543841

1,4-Butanediol, 2,3-bis(1,3-benzodioxol-5-ylmethyl)-, (2R,3R)-

1,4-Butanediol, 2,3-bis(1,3-benzodioxol-5-ylmethyl)-, (R*,R*)-(-)-

1,4-Butanediol, 2,3-bis(1,3-benzodioxol-5-ylmethyl)-, (R-(R*,R*))-

1,4-Butanediol, 2,3-bis(1,3-benzodioxol-5-ylmethyl)-, [R-(R*,R*)]-

Cubebin, dihydro-

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9180	91.80%
Caco-2	-	0.5462	54.62%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7350	73.50%
OATP2B1 inhibitior	-	0.8632	86.32%
OATP1B1 inhibitior	+	0.9512	95.12%
OATP1B3 inhibitior	+	0.9312	93.12%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8940	89.40%
P-glycoprotein inhibitior	+	0.6111	61.11%
P-glycoprotein substrate	-	0.9595	95.95%
CYP3A4 substrate	-	0.7213	72.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3682	36.82%
CYP3A4 inhibition	+	0.5303	53.03%
CYP2C9 inhibition	+	0.5719	57.19%
CYP2C19 inhibition	+	0.6731	67.31%
CYP2D6 inhibition	-	0.5832	58.32%
CYP1A2 inhibition	+	0.6825	68.25%
CYP2C8 inhibition	-	0.9395	93.95%
CYP inhibitory promiscuity	+	0.7178	71.78%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.4072	40.72%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.6254	62.54%
Skin irritation	-	0.6451	64.51%
Skin corrosion	-	0.9005	90.05%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8293	82.93%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.5145	51.45%
skin sensitisation	-	0.7868	78.68%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7838	78.38%
Acute Oral Toxicity (c)	III	0.6674	66.74%
Estrogen receptor binding	+	0.8334	83.34%
Androgen receptor binding	+	0.7912	79.12%
Thyroid receptor binding	+	0.5333	53.33%
Glucocorticoid receptor binding	-	0.6604	66.04%
Aromatase binding	-	0.5226	52.26%
PPAR gamma	+	0.7625	76.25%
Honey bee toxicity	-	0.8936	89.36%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9450	94.50%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL289	P10635	Cytochrome P450 2D6	17500 nM	IC50	PMID: 15679319
CHEMBL340	P08684	Cytochrome P450 3A4	9500 nM	IC50	PMID: 15679319

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.05%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.64%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.60%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.66%	98.95%
CHEMBL3492	P49721	Proteasome Macropain subunit	87.95%	90.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.53%	92.62%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.56%	94.80%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.74%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.98%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.82%	86.33%

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.

Aralia bipinnata

Arctium lappa

Aristolochia constricta

Aristolochia pubescens

Cleistanthus collinus

Cnidoscolus texanus

Diospyros montana

Dracaena hanningtonii

Flaveria bidentis

Horsfieldia glabra

Horsfieldia irya

Horsfieldia iryaghedhi