(+)-Nortrachelogenin

Details

• Internal ID: b4b6f090-1d6a-40df-ab15-da1a059cf2c5
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans > Dibenzylbutyrolactone lignans
• IUPAC Name: (3R,4R)-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
• SMILES (Canonical): COC1=C(C=CC(=C1)CC2COC(=O)C2(CC3=CC(=C(C=C3)O)OC)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C[C@@H]2COC(=O)[C@]2(CC3=CC(=C(C=C3)O)OC)O)O
• InChI: InChI=1S/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-11-27-19(23)20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3/t14-,20-/m1/s1
• InChI Key: ZITBJWXLODLDRH-JLTOFOAXSA-N
• Popularity: 23 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₇
• Molecular Weight: 374.40 g/mol
• Exact Mass: 374.13655304 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.80
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• Wikstromol
• 61521-74-2
• (3R-cis)-Dihydro-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)-3-hydroxy-2(3H)-furanone
• UNII-5HG1T9G09U
• 5HG1T9G09U
• (3R,4R)-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
• 2(3H)-Furanone, dihydro-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)-3-hydroxy-, (3R-cis)-
• CHEMBL453799
• HY-N3171A
• AKOS040762124
• MS-26048
• CS-0138773
• Q27262210
• (3R,4R)-3-Hydroxy-3,4-bis-(4-hydroxy-3-methoxy-benzyl)-dihydro-furan-2-one
• (3R,4R)-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxy-phenyl)methyl]tetrahydrofuran-2-one
• 2(3H)-FURANONE, DIHYDRO-3-HYDROXY-3,4-BIS((4-HYDROXY-3-METHOXYPHENYL)METHYL)-, (3R,4R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9488	94.88%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8761	87.61%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.9534	95.34%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5672	56.72%
P-glycoprotein inhibitior	-	0.4546	45.46%
P-glycoprotein substrate	-	0.7667	76.67%
CYP3A4 substrate	+	0.5603	56.03%
CYP2C9 substrate	-	0.6050	60.50%
CYP2D6 substrate	-	0.7355	73.55%
CYP3A4 inhibition	-	0.6122	61.22%
CYP2C9 inhibition	-	0.6347	63.47%
CYP2C19 inhibition	-	0.5940	59.40%
CYP2D6 inhibition	-	0.9120	91.20%
CYP1A2 inhibition	-	0.6277	62.77%
CYP2C8 inhibition	+	0.5063	50.63%
CYP inhibitory promiscuity	-	0.6084	60.84%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6091	60.91%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8485	84.85%
Skin irritation	-	0.8351	83.51%
Skin corrosion	-	0.9622	96.22%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4665	46.65%
Micronuclear	+	0.5166	51.66%
Hepatotoxicity	+	0.5677	56.77%
skin sensitisation	-	0.8530	85.30%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6862	68.62%
Acute Oral Toxicity (c)	III	0.5297	52.97%
Estrogen receptor binding	+	0.9090	90.90%
Androgen receptor binding	+	0.6078	60.78%
Thyroid receptor binding	+	0.7403	74.03%
Glucocorticoid receptor binding	+	0.6766	67.66%
Aromatase binding	+	0.5355	53.55%
PPAR gamma	+	0.6049	60.49%
Honey bee toxicity	-	0.8852	88.52%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9731	97.31%

Targets

Proven Targets:

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	99.06%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.99%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.49%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.36%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.78%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.97%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.71%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.91%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.34%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.85%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.47%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.58%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.54%	89.00%
CHEMBL2535	P11166	Glucose transporter	80.83%	98.75%

Plants that contains it

• Acacia simplicifolia
• Agathis lanceolata
• Bowdichia virgilioides
• Carissa carandas
• Carissa spinarum
• Cedrus deodara
• Centaurea zuccariniana
• Chamaecytisus austriacus
• Cousinia canescens
• Daphne acutiloba
• Daphne feddei
• Daphne oleoides
• Dracaena concinna
• Firmiana simplex
• Isodon amethystoides
• Nauclea parva
• Neolitsea pulchella
• Salvia miltiorrhiza
• Symplocos glauca
• Taxus cuspidata
• Teucrium scorodonia
• Tinospora hainanensis
• Titanotrichum oldhamii
• Trachelospermum asiaticum
• Trachelospermum jasminoides
• Uvaria littoralis
• Veronica anagallis
• Vigna angularis
• Waitzia acuminata
• Wikstroemia indica
• Wrightia tinctoria

Cross-Links

• PubChem: 479756
• NPASS: NPC253481
• LOTUS: LTS0148812
• wikiData: Q27262210