Auraptenol

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	05554a7c-c8e4-4124-a9e0-ce5d29466860
Taxonomy	Phenylpropanoids and polyketides > Coumarins and derivatives
IUPAC Name	8-(2-hydroxy-3-methylbut-3-enyl)-7-methoxychromen-2-one
SMILES (Canonical)	CC(=C)C(CC1=C(C=CC2=C1OC(=O)C=C2)OC)O
SMILES (Isomeric)	CC(=C)C(CC1=C(C=CC2=C1OC(=O)C=C2)OC)O
InChI	InChI=1S/C15H16O4/c1-9(2)12(16)8-11-13(18-3)6-4-10-5-7-14(17)19-15(10)11/h4-7,12,16H,1,8H2,2-3H3
InChI Key	SQSRYWNOKPJENY-UHFFFAOYSA-N
Popularity	5 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₅H₁₆O₄
Molecular Weight	260.28 g/mol
Exact Mass	260.10485899 g/mol
Topological Polar Surface Area (TPSA)	55.80 Å²
XlogP	2.80
Atomic LogP (AlogP)	2.28
H-Bond Acceptor	4
H-Bond Donor	1
Rotatable Bonds	4

Synonyms

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(S)-Auraptenol

51559-35-4

8-(2-hydroxy-3-methylbut-3-enyl)-7-methoxychromen-2-one

8-(2-hydroxy-3-methylbut-3-en-1-yl)-7-methoxy-2H-chromen-2-one

(+)-Auraptenol

2H-1-Benzopyran-2-one, 8-(2-hydroxy-3-methyl-3-buten-1-yl)-7-methoxy-

DTXSID00537563

CHEBI:174413

SQSRYWNOKPJENY-UHFFFAOYSA-N

8-[(2S)-2-Hydroxy-3-methyl-3-buten-1-yl]-7-methoxy-2H-1-benzopyran-2-one; (+)-Auraptenol;2H-1-Benzopyran-2-one, 8-(2-hydroxy-3-methyl-3-butenyl)-7-methoxy-, (S)-; 2H-1-Benzopyran-2-one, 8-[(2S)-2-hydroxy-3-methyl-3-butenyl]-7-methoxy-

There are more than 10 synonyms. If you wish to see them all click here.

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	+	0.9890	98.90%
Caco-2	+	0.5901	59.01%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5966	59.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9134	91.34%
OATP1B3 inhibitior	+	0.9303	93.03%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.4757	47.57%
P-glycoprotein inhibitior	-	0.8591	85.91%
P-glycoprotein substrate	-	0.8222	82.22%
CYP3A4 substrate	-	0.5553	55.53%
CYP2C9 substrate	-	0.8217	82.17%
CYP2D6 substrate	-	0.7862	78.62%
CYP3A4 inhibition	-	0.5454	54.54%
CYP2C9 inhibition	-	0.7799	77.99%
CYP2C19 inhibition	+	0.5203	52.03%
CYP2D6 inhibition	-	0.8400	84.00%
CYP1A2 inhibition	+	0.5230	52.30%
CYP2C8 inhibition	-	0.7566	75.66%
CYP inhibitory promiscuity	+	0.5410	54.10%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6928	69.28%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.8006	80.06%
Skin irritation	-	0.7256	72.56%
Skin corrosion	-	0.9625	96.25%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5552	55.52%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	+	0.6056	60.56%
skin sensitisation	-	0.7418	74.18%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5842	58.42%
Acute Oral Toxicity (c)	III	0.4557	45.57%
Estrogen receptor binding	-	0.5292	52.92%
Androgen receptor binding	-	0.5433	54.33%
Thyroid receptor binding	+	0.5184	51.84%
Glucocorticoid receptor binding	+	0.5540	55.40%
Aromatase binding	-	0.4831	48.31%
PPAR gamma	+	0.8190	81.90%
Honey bee toxicity	-	0.8541	85.41%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.9871	98.71%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.62%	83.82%
CHEMBL2581	P07339	Cathepsin D	95.12%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	93.47%	90.20%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.66%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.19%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.64%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.54%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.18%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.08%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.82%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	81.47%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.21%	96.00%

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.