1,2-Benzenediol, 4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]-

Details

• Internal ID: c66a154c-0e30-4284-88e5-1ac8cb4faeae
• Taxonomy: Lignans, neolignans and related compounds > Stilbenolignans
• IUPAC Name: 4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,2-diol
• SMILES (Canonical): C1=CC2=C(C=C1C=CC3=CC(=CC(=C3)O)O)OC(C(O2)C4=CC(=C(C=C4)O)O)C5=CC(=CC(=C5)O)O
• SMILES (Isomeric): C1=CC2=C(C=C1/C=C/C3=CC(=CC(=C3)O)O)O[C@H]([C@@H](O2)C4=CC(=C(C=C4)O)O)C5=CC(=CC(=C5)O)O
• InChI: InChI=1S/C28H22O8/c29-19-7-16(8-20(30)13-19)2-1-15-3-6-25-26(9-15)36-28(18-10-21(31)14-22(32)11-18)27(35-25)17-4-5-23(33)24(34)12-17/h1-14,27-34H/b2-1+/t27-,28-/m0/s1
• InChI Key: NKUZVJOKTLLGKC-UVQWMVBFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₂O₈
• Molecular Weight: 486.50 g/mol
• Exact Mass: 486.13146766 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 5.34
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 1,2-Benzenediol, 4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]-
• 4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-[(E)-2-(3,5-dihydroxyphenyl)vinyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,2-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8961	89.61%
Caco-2	-	0.8415	84.15%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Nucleus	0.4266	42.66%
OATP2B1 inhibitior	+	0.5708	57.08%
OATP1B1 inhibitior	+	0.9579	95.79%
OATP1B3 inhibitior	+	0.9808	98.08%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8040	80.40%
P-glycoprotein inhibitior	+	0.6990	69.90%
P-glycoprotein substrate	-	0.9680	96.80%
CYP3A4 substrate	-	0.5433	54.33%
CYP2C9 substrate	+	0.6202	62.02%
CYP2D6 substrate	+	0.3444	34.44%
CYP3A4 inhibition	+	0.6100	61.00%
CYP2C9 inhibition	+	0.6223	62.23%
CYP2C19 inhibition	-	0.7168	71.68%
CYP2D6 inhibition	-	0.8972	89.72%
CYP1A2 inhibition	+	0.6973	69.73%
CYP2C8 inhibition	+	0.7352	73.52%
CYP inhibitory promiscuity	+	0.7825	78.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6140	61.40%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.5203	52.03%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9098	90.98%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8911	89.11%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.6612	66.12%
skin sensitisation	-	0.6558	65.58%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7423	74.23%
Acute Oral Toxicity (c)	II	0.6415	64.15%
Estrogen receptor binding	+	0.7510	75.10%
Androgen receptor binding	+	0.7321	73.21%
Thyroid receptor binding	+	0.7256	72.56%
Glucocorticoid receptor binding	+	0.6900	69.00%
Aromatase binding	+	0.5311	53.11%
PPAR gamma	+	0.7835	78.35%
Honey bee toxicity	-	0.7366	73.66%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9388	93.88%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.71%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.17%	91.11%
CHEMBL3194	P02766	Transthyretin	96.18%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.18%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.41%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	88.38%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.11%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.66%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.89%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.48%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.74%	96.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	84.93%	96.12%

Plants that contains it

• Acacia adunca
• Adiantum philippense
• Aldama incana
• Annona cornifolia
• Artemisia pedemontana subsp. assoana
• Astragalus sempervirens
• Calostephane divaricata
• Caragana aurantiaca
• Caragana rosea
• Chaenomeles sinensis
• Dumortiera hirsuta
• Echeveria secunda
• Eucalyptus melliodora
• Gnetum latifolium
• Goniothalamus malayanus
• Hedysarum inundatum
• Hypericum laricifolium
• Ipomoea digitata
• Lepisorus ussuriensis
• Lysimachia mauritiana
• Marrubium anisodon
• Naucleopsis ternstroemiiflora
• Ocotea pittieri
• Pastinaca sativa
• Peltostigma guatemalense
• Premna odorata
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Salvia syriaca
• Scutellaria amoena
• Solanum laxum
• Swertia franchetiana
• Vaccinium oxycoccos
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 5279246
• NPASS: NPC260342
• LOTUS: LTS0129138
• wikiData: Q105181181