Kobusin

Details

• Internal ID: 28e36c36-773f-4d5a-9dc9-b6c0cd160310
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 5-[(3S,3aR,6S,6aR)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-1,3-benzodioxole
• SMILES (Canonical): COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC5=C(C=C4)OCO5)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC5=C(C=C4)OCO5)OC
• InChI: InChI=1S/C21H22O6/c1-22-16-5-3-12(7-18(16)23-2)20-14-9-25-21(15(14)10-24-20)13-4-6-17-19(8-13)27-11-26-17/h3-8,14-15,20-21H,9-11H2,1-2H3/t14-,15-,20+,21+/m0/s1
• InChI Key: AWOGQCSIVCQXBT-VUEDXXQZSA-N
• Popularity: 18 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.14163842 g/mol
• Topological Polar Surface Area (TPSA): 55.40 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.51
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 36150-23-9
• (+)-Kobusin
• (+)-Demethoxyaschantin
• (+)-Spinescin
• CUR4HUP6JQ
• 5-[(3S,3aR,6S,6aR)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-1,3-benzodioxole
• Demethoxyaschantin
• (3abeta,6abeta)-1beta-(3,4-Dimethoxyphenyl)-4beta-(1,3-benzodioxole-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan
• Methylpiperitol
• UNII-CUR4HUP6JQ
• (+)-METHYLPIPERITOL
• CHEMBL462822
• MEGxp0_001295
• SCHEMBL17999860
• ACon1_001273
• DTXSID00189723
• CHEBI:133905
• HY-N5101
• AKOS040760503
• NCGC00169511-01
• CS-0032366
• C17844
• 1,3-BENZODIOXOLE, 5-((1S,3AR,4S,6AR)-4-(3,4-DIMETHOXYPHENYL)TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1-YL)-
• 5-((1S,3AR,4S,6AR)-4-(3,4-DIMETHOXYPHENYL)TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1-YL)-1,3-BENZODIOXOLE
• 5-[(1S,3aR,4S,6aR)-4-(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2H-1,3-benzodioxole

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	+	0.6736	67.36%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7366	73.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9381	93.81%
OATP1B3 inhibitior	+	0.9729	97.29%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8904	89.04%
P-glycoprotein inhibitior	+	0.7667	76.67%
P-glycoprotein substrate	-	0.9126	91.26%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3551	35.51%
CYP3A4 inhibition	+	0.9329	93.29%
CYP2C9 inhibition	+	0.9049	90.49%
CYP2C19 inhibition	+	0.9568	95.68%
CYP2D6 inhibition	+	0.7208	72.08%
CYP1A2 inhibition	+	0.6621	66.21%
CYP2C8 inhibition	-	0.7085	70.85%
CYP inhibitory promiscuity	+	0.9536	95.36%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9108	91.08%
Carcinogenicity (trinary)	Non-required	0.4354	43.54%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.8624	86.24%
Skin irritation	-	0.8208	82.08%
Skin corrosion	-	0.9676	96.76%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8393	83.93%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.6220	62.20%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.7121	71.21%
Acute Oral Toxicity (c)	III	0.6518	65.18%
Estrogen receptor binding	+	0.7425	74.25%
Androgen receptor binding	+	0.7694	76.94%
Thyroid receptor binding	+	0.6184	61.84%
Glucocorticoid receptor binding	+	0.5959	59.59%
Aromatase binding	-	0.6656	66.56%
PPAR gamma	+	0.5715	57.15%
Honey bee toxicity	-	0.8384	83.84%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9882	98.82%

Targets

Proven Targets:

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	95.44%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.80%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.97%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.09%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.95%	86.33%
CHEMBL3438	Q05513	Protein kinase C zeta	88.65%	88.48%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.17%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.15%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.03%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.45%	97.14%
CHEMBL2535	P11166	Glucose transporter	85.83%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.30%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.16%	92.94%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.45%	96.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.14%	82.67%
CHEMBL2581	P07339	Cathepsin D	82.88%	98.95%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	82.72%	85.49%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.31%	96.77%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.23%	94.80%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.22%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.44%	89.00%

Plants that contains it

• Achillea holosericea
• Achillea lingulata
• Aiouea trinervis
• Aristolochia gehrtii
• Aristolochia gigantea
• Artemisia absinthium
• Artemisia arborescens
• Artemisia gorgonum
• Esenbeckia leiocarpa
• Fleischmannia multinervis
• Geranium platyanthum
• Geranium thunbergii
• Leucophyllum ambiguum
• Machilus wangchiana
• Magnolia biondii
• Magnolia denudata
• Magnolia kobus
• Magnolia salicifolia
• Magnolia sprengeri
• Magnolia stellata
• Melicope hayesii
• Microcos paniculata
• Pandanus boninensis
• Pandanus tectorius
• Phyllodium pulchellum
• Quassia bidwillii
• Raulinoa echinata
• Sesamum indicum
• Teucrium viscidum
• Virola flexuosa
• Virola venosa
• Zanthoxylum armatum
• Zanthoxylum culantrillo
• Zanthoxylum rhetsa
• Zanthoxylum simulans

Cross-Links

• PubChem: 182278
• NPASS: NPC82111
• ChEMBL: CHEMBL462822
• LOTUS: LTS0081634
• wikiData: Q83061925