(3S,3aS,6S,6aR)-3,6-bis(3,4-dihydroxyphenyl)-3,3a,6,6a-tetrahydro-1H-furo[3,4-c]furan-4-one

Details

• Internal ID: 70f4cd78-3afd-49d4-a693-cc7ae6475a08
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones
• IUPAC Name: (3S,3aS,6S,6aR)-3,6-bis(3,4-dihydroxyphenyl)-3,3a,6,6a-tetrahydro-1H-furo[3,4-c]furan-4-one
• SMILES (Canonical): C1C2C(C(O1)C3=CC(=C(C=C3)O)O)C(=O)OC2C4=CC(=C(C=C4)O)O
• SMILES (Isomeric): C1[C@H]2[C@@H]([C@H](O1)C3=CC(=C(C=C3)O)O)C(=O)O[C@@H]2C4=CC(=C(C=C4)O)O
• InChI: InChI=1S/C18H16O7/c19-11-3-1-8(5-13(11)21)16-10-7-24-17(15(10)18(23)25-16)9-2-4-12(20)14(22)6-9/h1-6,10,15-17,19-22H,7H2/t10-,15-,16+,17+/m0/s1
• InChI Key: DFZNKMAEHVZMHR-YQMWTZAJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₇
• Molecular Weight: 344.30 g/mol
• Exact Mass: 344.08960285 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.11
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• BDBM50208825
• (+)-3,4,3',4'-Tetrahydroxy-9,7'alpha-epoxy-7alpha,9'-lactone
• (+)-3,4,3'',4''-tetrahydroxy-9,7''alpha-epoxylignano-7 alpha,9''-lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9757	97.57%
Caco-2	-	0.6690	66.90%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8130	81.30%
OATP2B1 inhibitior	-	0.7180	71.80%
OATP1B1 inhibitior	+	0.9625	96.25%
OATP1B3 inhibitior	+	0.8781	87.81%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6131	61.31%
P-glycoprotein inhibitior	-	0.7173	71.73%
P-glycoprotein substrate	-	0.9474	94.74%
CYP3A4 substrate	-	0.5521	55.21%
CYP2C9 substrate	+	0.5986	59.86%
CYP2D6 substrate	-	0.7966	79.66%
CYP3A4 inhibition	-	0.8135	81.35%
CYP2C9 inhibition	+	0.6351	63.51%
CYP2C19 inhibition	-	0.6705	67.05%
CYP2D6 inhibition	-	0.8796	87.96%
CYP1A2 inhibition	+	0.6016	60.16%
CYP2C8 inhibition	-	0.8129	81.29%
CYP inhibitory promiscuity	-	0.6059	60.59%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5414	54.14%
Eye corrosion	-	0.9909	99.09%
Eye irritation	+	0.6975	69.75%
Skin irritation	-	0.6016	60.16%
Skin corrosion	-	0.9629	96.29%
Ames mutagenesis	+	0.6263	62.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4158	41.58%
Micronuclear	+	0.8774	87.74%
Hepatotoxicity	-	0.6842	68.42%
skin sensitisation	-	0.7913	79.13%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6899	68.99%
Acute Oral Toxicity (c)	III	0.4144	41.44%
Estrogen receptor binding	+	0.7695	76.95%
Androgen receptor binding	+	0.7009	70.09%
Thyroid receptor binding	+	0.7056	70.56%
Glucocorticoid receptor binding	+	0.6325	63.25%
Aromatase binding	-	0.6580	65.80%
PPAR gamma	+	0.6679	66.79%
Honey bee toxicity	-	0.7915	79.15%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9790	97.90%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	5600 nM	IC50	PMID: 22342628

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.33%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.01%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.29%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.56%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.76%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.50%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.07%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.78%	99.23%

Plants that contains it

• Morinda citrifolia

Cross-Links

• PubChem: 16681478
• NPASS: NPC308976
• ChEMBL: CHEMBL227135
• LOTUS: LTS0085819
• wikiData: Q104978480