(-)-Dehydrodiconiferyl Alcohol

Details

• Internal ID: beb16180-f326-436b-8e17-f89def3bd438
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 4-[(2R,3S)-3-(hydroxymethyl)-5-[(E)-3-hydroxyprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C=C3)O)OC)C=CCO
• SMILES (Isomeric): COC1=CC(=CC2=C1O[C@H]([C@@H]2CO)C3=CC(=C(C=C3)O)OC)/C=C/CO
• InChI: InChI=1S/C20H22O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h3-6,8-10,15,19,21-23H,7,11H2,1-2H3/b4-3+/t15-,19+/m1/s1
• InChI Key: KUSXBOZNRPQEON-GWKPYITFSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.14163842 g/mol
• Topological Polar Surface Area (TPSA): 88.40 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 155836-29-6
• 5-O-Methylhierochin D
• (7R,8S)-dehydrodiconiferyl alcohol
• CHEBI:70467
• (-)-DCA
• 4-[(2R,3S)-3-(hydroxymethyl)-5-[(E)-3-hydroxyprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
• 7-Methoxy-5-[(E)-3-hydroxy-1-propenyl]-2beta-(3-methoxy-4-hydroxyphenyl)-2,3-dihydrobenzofuran-3alpha-methanol
• CHEMBL1761712
• DTXSID701107496
• HY-N2682
• (2R,3S)-dehydrodiconiferyl alcohol
• AKOS040761186
• (-)-(2R,3S)-dehydrodiconiferyl alcohol
• CS-0023122
• Q27138804
• (2R)-5-[(E)-3-Hydroxy-1-propenyl]-2,3-dihydro-2beta-(4-hydroxy-3-methoxyphenyl)-7-methoxybenzofuran-3alpha-methanol
• (2R,3S)-2,3-Dihydro-2-(4-hydroxy-3-methoxyphenyl)-5-[(1E)-3-hydroxy-1-propen-1-yl]-7-methoxy-3-benzofuranmethanol
• 2beta-(3-Methoxy-4-hydroxyphenyl)-5-(3-hydroxy-1-propenyl)-7-methoxy-2,3-dihydrobenzofuran-3alpha-methanol
• 4-{(2R,3S)-3-(hydroxymethyl)-5-[(1E)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl}-2-methoxyphenol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9854	98.54%
Caco-2	+	0.6050	60.50%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7034	70.34%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.8276	82.76%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7561	75.61%
P-glycoprotein inhibitior	+	0.6369	63.69%
P-glycoprotein substrate	-	0.8423	84.23%
CYP3A4 substrate	+	0.5531	55.31%
CYP2C9 substrate	+	0.6095	60.95%
CYP2D6 substrate	-	0.6654	66.54%
CYP3A4 inhibition	+	0.5306	53.06%
CYP2C9 inhibition	+	0.8317	83.17%
CYP2C19 inhibition	+	0.8537	85.37%
CYP2D6 inhibition	-	0.7554	75.54%
CYP1A2 inhibition	+	0.6044	60.44%
CYP2C8 inhibition	+	0.7117	71.17%
CYP inhibitory promiscuity	+	0.9666	96.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9208	92.08%
Carcinogenicity (trinary)	Non-required	0.4695	46.95%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8899	88.99%
Skin irritation	-	0.8023	80.23%
Skin corrosion	-	0.9506	95.06%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4663	46.63%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.6983	69.83%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5614	56.14%
Acute Oral Toxicity (c)	III	0.6081	60.81%
Estrogen receptor binding	+	0.8145	81.45%
Androgen receptor binding	+	0.6851	68.51%
Thyroid receptor binding	+	0.7584	75.84%
Glucocorticoid receptor binding	+	0.7321	73.21%
Aromatase binding	+	0.5780	57.80%
PPAR gamma	-	0.4855	48.55%
Honey bee toxicity	-	0.8714	87.14%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9345	93.45%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL206	P03372	Estrogen receptor alpha	61.91 nM	IC50	via Super-PRED
CHEMBL242	Q92731	Estrogen receptor beta	286.5 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.69%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.99%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.78%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.49%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.20%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.78%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.25%	99.17%
CHEMBL3194	P02766	Transthyretin	85.79%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	85.64%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.22%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.15%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.64%	89.62%

Plants that contains it

• Achlys triphylla
• Aglaia foveolata
• Albizia procera
• Anastatica hierochuntica
• Artemisia giraldii
• Arum italicum
• Brassica fruticulosa
• Bulbophyllum protractum
• Calystegia pubescens
• Campylotropis hirtella
• Cypripedium calceolus
• Diospyros japonica
• Euonymus alatus
• Hortonia floribunda
• Kadsura coccinea
• Lactuca sativa
• Lampranthus sociorum
• Perymenium mendezii
• Picea glauca
• Pinellia ternata
• Pongamia pinnata
• Protium tonkinense
• Sambucus williamsii
• Sarcandra glabra
• Seriphidium porrectum
• Tarchonanthus camphoratus
• Uncaria rhynchophylla
• Wikstroemia canescens

Cross-Links

• PubChem: 11078843
• NPASS: NPC156502
• ChEMBL: CHEMBL1761712
• LOTUS: LTS0251671
• wikiData: Q27138804