(l)-Edunol

Details

• Internal ID: f92c587c-f146-4783-895e-f4c101a95c95
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (1R,12R)-15-(3-methylbut-2-enyl)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-ol
• SMILES (Canonical): CC(=CCC1=CC2=C(C=C1O)OCC3C2OC4=CC5=C(C=C34)OCO5)C
• SMILES (Isomeric): CC(=CCC1=CC2=C(C=C1O)OC[C@@H]3[C@H]2OC4=CC5=C(C=C34)OCO5)C
• InChI: InChI=1S/C21H20O5/c1-11(2)3-4-12-5-14-17(7-16(12)22)23-9-15-13-6-19-20(25-10-24-19)8-18(13)26-21(14)15/h3,5-8,15,21-22H,4,9-10H2,1-2H3/t15-,21-/m0/s1
• InChI Key: UFBHHWPUVXVFRG-BTYIYWSLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₅
• Molecular Weight: 352.40 g/mol
• Exact Mass: 352.13107373 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Edunol, (-)-
• 33909-74-9
• (l)-Edunol
• NSC 356826
• NSC-356826
• NSC356826
• (?)-Edunol
• UNII-ZVBPULMDW4
• (-)-EDUNOL
• CHEMBL1976045
• DTXSID30955498
• NCI60_003227
• (-)-2-ISOPENTENYL-3-HYDROXY-8,9-METHYLENEDIOXYPTEROCARPAN
• (6AR,12AR)-6A,12A-DIHYDRO-2-(3-METHYL-2-BUTEN-1-YL)-6H-(1,3)DIOXOLO(5,6)BENZOFURO(3,2-C)(1)BENZOPYRAN-3-OL
• 2-(3-Methylbut-2-en-1-yl)-6a,12a-dihydro-6H,9H-[1,3]dioxolo[5,6][1]benzofuro[3,2-c][1]benzopyran-3-ol
• 6H-(1,3)DIOXOLO(5,6)BENZOFURO(3,2-C)(1)BENZOPYRAN-3-OL, 6A,12A-DIHYDRO-2-(3-METHYL-2-BUTEN-1-YL)-, (6AR,12AR)-
• 6H-(1,3)DIOXOLO(5,6)BENZOFURO(3,2-C)(1)BENZOPYRAN-3-OL, 6A,12A-DIHYDRO-2-(3-METHYL-2-BUTENYL)-, (6AR-CIS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9857	98.57%
Caco-2	+	0.6114	61.14%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7342	73.42%
OATP2B1 inhibitior	-	0.8664	86.64%
OATP1B1 inhibitior	+	0.8797	87.97%
OATP1B3 inhibitior	+	0.9650	96.50%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8745	87.45%
P-glycoprotein inhibitior	+	0.6605	66.05%
P-glycoprotein substrate	-	0.7859	78.59%
CYP3A4 substrate	-	0.5052	50.52%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	+	0.3715	37.15%
CYP3A4 inhibition	+	0.6911	69.11%
CYP2C9 inhibition	+	0.7544	75.44%
CYP2C19 inhibition	+	0.8314	83.14%
CYP2D6 inhibition	+	0.5089	50.89%
CYP1A2 inhibition	+	0.6852	68.52%
CYP2C8 inhibition	-	0.6827	68.27%
CYP inhibitory promiscuity	+	0.8249	82.49%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5863	58.63%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.7384	73.84%
Skin irritation	-	0.7314	73.14%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4388	43.88%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.6360	63.60%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6439	64.39%
Acute Oral Toxicity (c)	III	0.5664	56.64%
Estrogen receptor binding	+	0.9197	91.97%
Androgen receptor binding	+	0.6002	60.02%
Thyroid receptor binding	+	0.7242	72.42%
Glucocorticoid receptor binding	+	0.8567	85.67%
Aromatase binding	+	0.5772	57.72%
PPAR gamma	+	0.8456	84.56%
Honey bee toxicity	-	0.8726	87.26%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9904	99.04%

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	99.23%	91.11%
CHEMBL2039	P27338	Monoamine oxidase B	94.22%	92.51%
CHEMBL2581	P07339	Cathepsin D	90.38%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.22%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.28%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.20%	94.80%
CHEMBL3401	O75469	Pregnane X receptor	88.53%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.05%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.66%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.13%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.61%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.71%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.20%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.73%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.35%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.41%	93.40%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.47%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	80.21%	91.49%

Plants that contains it

• Abies alba
• Abies pinsapo subsp. marocana
• Ampelocera edentula
• Angelica acutiloba
• Arnica mollis
• Brassica carinata
• Bryonia alba
• Carpha glomerata
• Croton gratissimus
• Cyanostegia angustifolia
• Dactylorhiza viridis
• Diplopterygium glaucum
• Eucalyptus resinifera
• Euphrasia nana
• Eurycoma harmandiana
• Ixeris japonica
• Lysimachia fordiana
• Orthosiphon aristatus
• Oxytropis falcata
• Pterolobium hexapetalum
• Ranunculus asiaticus
• Remirea maritima
• Sinapis alba
• Solanum lanceolatum
• Viburnum erubescens
• Wikstroemia indica
• Xanthorhiza simplicissima

Cross-Links

• PubChem: 182148
• NPASS: NPC71726
• LOTUS: LTS0254316
• wikiData: Q82935131