Neorautenol

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	7bcccc8f-088a-485d-ab8f-91b8ed8968d7
Taxonomy	Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
IUPAC Name	(2R,10R)-17,17-dimethyl-3,12,16-trioxapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(13),4(9),5,7,14,18,20-heptaen-6-ol
SMILES (Canonical)	CC1(C=CC2=CC3=C(C=C2O1)OCC4C3OC5=C4C=CC(=C5)O)C
SMILES (Isomeric)	CC1(C=CC2=CC3=C(C=C2O1)OC[C@@H]4[C@H]3OC5=C4C=CC(=C5)O)C
InChI	InChI=1S/C20H18O4/c1-20(2)6-5-11-7-14-17(9-16(11)24-20)22-10-15-13-4-3-12(21)8-18(13)23-19(14)15/h3-9,15,19,21H,10H2,1-2H3/t15-,19-/m0/s1
InChI Key	OGFFMQWYZCTXCM-KXBFYZLASA-N
Popularity	7 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₀H₁₈O₄
Molecular Weight	322.40 g/mol
Exact Mass	322.12050905 g/mol
Topological Polar Surface Area (TPSA)	47.90 Å²
XlogP	3.60
Atomic LogP (AlogP)	4.19
H-Bond Acceptor	4
H-Bond Donor	1
Rotatable Bonds	0

Synonyms

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53766-52-2

RefChem:165378

CHEMBL1098728

SCHEMBL31060647

BDBM50317432

XN161719

(-)-Neorautenol;(7aR,12aS)-7a,12a-Dihydro-3,3-dimethyl-3H,7H-benzofuro[3,2-c]pyrano[3,2-g][1]benzopyran-10-ol

(2R,10R)-17,17-dimethyl-3,12,16-trioxapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(13),4(9),5,7,14,18,20-heptaen-6-ol

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	+	0.8067	80.67%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7829	78.29%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.8796	87.96%
OATP1B3 inhibitior	+	0.9734	97.34%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7840	78.40%
P-glycoprotein inhibitior	-	0.6934	69.34%
P-glycoprotein substrate	+	0.6709	67.09%
CYP3A4 substrate	+	0.6021	60.21%
CYP2C9 substrate	+	0.8070	80.70%
CYP2D6 substrate	-	0.7007	70.07%
CYP3A4 inhibition	-	0.5161	51.61%
CYP2C9 inhibition	+	0.6678	66.78%
CYP2C19 inhibition	+	0.7011	70.11%
CYP2D6 inhibition	-	0.5932	59.32%
CYP1A2 inhibition	+	0.8308	83.08%
CYP2C8 inhibition	+	0.8147	81.47%
CYP inhibitory promiscuity	+	0.7297	72.97%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5162	51.62%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.5678	56.78%
Skin irritation	-	0.7580	75.80%
Skin corrosion	-	0.9507	95.07%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4313	43.13%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.6526	65.26%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6476	64.76%
Acute Oral Toxicity (c)	III	0.5599	55.99%
Estrogen receptor binding	+	0.8899	88.99%
Androgen receptor binding	+	0.6248	62.48%
Thyroid receptor binding	+	0.7021	70.21%
Glucocorticoid receptor binding	+	0.6643	66.43%
Aromatase binding	-	0.5937	59.37%
PPAR gamma	+	0.7932	79.32%
Honey bee toxicity	-	0.8999	89.99%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9504	95.04%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	7600 nM	IC50	PMID: 18183025

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.24%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.83%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.22%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.22%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.81%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.61%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.11%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.94%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.28%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.53%	93.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.42%	97.14%
CHEMBL226	P30542	Adenosine A1 receptor	82.06%	95.93%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.