Hinokinin

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

Top

Internal ID	2f98ca78-53e3-44e5-8331-ab8061c163d6
Taxonomy	Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans > Dibenzylbutyrolactone lignans
IUPAC Name	(3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-one
SMILES (Canonical)	C1C(C(C(=O)O1)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5
SMILES (Isomeric)	C1[C@@H]([C@H](C(=O)O1)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5
InChI	InChI=1S/C20H18O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15H,5-6,9-11H2/t14-,15+/m0/s1
InChI Key	DDWGQGZPYDSYEL-LSDHHAIUSA-N
Popularity	63 references in papers

Physical and Chemical Properties

Top

Molecular Formula	C₂₀H₁₈O₆
Molecular Weight	354.40 g/mol
Exact Mass	354.11033829 g/mol
Topological Polar Surface Area (TPSA)	63.20 Å²
XlogP	3.70
Atomic LogP (AlogP)	2.72
H-Bond Acceptor	6
H-Bond Donor	0
Rotatable Bonds	4

Synonyms

Top

(-)-Hinokinin

26543-89-5

(3R,4R)-3,4-Bis(benzo[d][1,3]dioxol-5-ylmethyl)dihydrofuran-2(3H)-one

CHEBI:5722

CHEMBL242011

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

(3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)dihydrofuran-2(3H)-one

(3R-trans)-3,4-bis(1,3-benzodioxol-5-ylmethyl)dihydrofuran-2(3H)-one

hinoquinin

(-)-hinoquinin

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

2D Structure

Top

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9919	99.19%
Caco-2	+	0.5622	56.22%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8036	80.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9461	94.61%
OATP1B3 inhibitior	+	0.9535	95.35%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9238	92.38%
P-glycoprotein inhibitior	+	0.6543	65.43%
P-glycoprotein substrate	-	0.9266	92.66%
CYP3A4 substrate	-	0.6159	61.59%
CYP2C9 substrate	+	0.5975	59.75%
CYP2D6 substrate	-	0.7917	79.17%
CYP3A4 inhibition	+	0.8965	89.65%
CYP2C9 inhibition	+	0.7702	77.02%
CYP2C19 inhibition	+	0.8985	89.85%
CYP2D6 inhibition	+	0.6698	66.98%
CYP1A2 inhibition	+	0.8411	84.11%
CYP2C8 inhibition	-	0.9381	93.81%
CYP inhibitory promiscuity	+	0.8345	83.45%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9018	90.18%
Carcinogenicity (trinary)	Non-required	0.4711	47.11%
Eye corrosion	-	0.9787	97.87%
Eye irritation	-	0.5805	58.05%
Skin irritation	-	0.6771	67.71%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7904	79.04%
Micronuclear	+	0.5659	56.59%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.5880	58.80%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.5599	55.99%
Acute Oral Toxicity (c)	III	0.5196	51.96%
Estrogen receptor binding	+	0.9002	90.02%
Androgen receptor binding	+	0.7933	79.33%
Thyroid receptor binding	+	0.5396	53.96%
Glucocorticoid receptor binding	-	0.4716	47.16%
Aromatase binding	+	0.5197	51.97%
PPAR gamma	+	0.6728	67.28%
Honey bee toxicity	-	0.7815	78.15%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9939	99.39%

Targets

Top

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL289	P10635	Cytochrome P450 2D6	26500 nM	IC50	PMID: 15679319
CHEMBL340	P08684	Cytochrome P450 3A4	8000 nM	IC50	PMID: 15679319
CHEMBL238	Q01959	Dopamine transporter	8350 nM	IC50	PMID: 24112084
CHEMBL1903	P30531	GABA transporter 1	20600 nM	IC50	PMID: 24112084
CHEMBL222	P23975	Norepinephrine transporter	8760 nM	IC50	PMID: 24112084

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.30%	83.82%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.21%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.77%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	96.47%	94.80%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.10%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.92%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.83%	92.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.17%	93.40%
CHEMBL261	P00915	Carbonic anhydrase I	85.33%	96.76%
CHEMBL3401	O75469	Pregnane X receptor	85.09%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.98%	97.09%
CHEMBL1978	P11511	Cytochrome P450 19A1	84.54%	91.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.48%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.20%	96.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.15%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.94%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.17%	95.89%

Plants that contains it

Top

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.

Aglaia meridionalis

Allium ursinum

Ammi majus

Anthriscus sylvestris

Arcangelisia gusanlung

Aristolochia chamissonis

Aristolochia constricta

Aristolochia cucurbitifolia

Aristolochia cymbifera

Aristolochia gehrtii

Aristolochia indica

Aristolochia tomentosa