Auraptene

Details

• Internal ID: bef2d3a7-576f-4c8c-8993-c43da0a28d76
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
• SMILES (Canonical): CC(=CCCC(=CCOC1=CC2=C(C=C1)C=CC(=O)O2)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/COC1=CC2=C(C=C1)C=CC(=O)O2)/C)C
• InChI: InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+
• InChI Key: RSDDHGSKLOSQFK-RVDMUPIBSA-N
• Popularity: 211 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₃
• Molecular Weight: 298.40 g/mol
• Exact Mass: 298.15689456 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.86
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• Aurapten
• 495-02-3
• 7-Geranyloxycoumarin
• UNII-F79I1ZEL2E
• F79I1ZEL2E
• CCRIS 8835
• (E)-7-((3,7-Dimethylocta-2,6-dien-1-yl)oxy)-2H-chromen-2-one
• 2H-1-Benzopyran-2-one, 7-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-
• 7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one
• 7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
• 7-(geranyloxy)coumarin
• SR-01000758940
• Feronialactone
• 7-([(2E)-3,7-Dimethyl-2,6-octadienyl]oxy)-2H-chromen-2-one
• 7-{[(2E)-3,7-dimethyl-2,6-octadienyl]oxy}-2H-chromen-2-one
• 2H-1-Benzopyran-2-one, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)-
• 2H-1-Benzopyran-2-one, 7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-
• 2H-1-BENZOPYRAN-2-ONE, 7-(((2E)-3,7-DIMETHYL-2,6-OCTADIEN-1-YL)OXY)-
• 7-O-geranylumbelliferone
• UPCMLD-DP061
• 7-(3,7-dimethylocta-2,6-dienoxy)-1-benzopyran-2-one
• Coumarin, 7-(geranyloxy)-
• MLS001049098
• SPECTRUM1505176
• CHEMBL307341
• MEGxp0_000091
• SCHEMBL2535029
• SCHEMBL2535034
• Auraptene, >=98% (HPLC)
• UPCMLD-DP061:001
• ACon1_000071
• CHEBI:93486
• DTXSID80897576
• CHEBI:134355
• HMS2270C13
• HMS3886N14
• NP344
• AMY36802
• BCP23751
• HY-N2388
• BDBM50361373
• MFCD00075948
• NSC711511
• s9052
• STL457597
• AKOS015969736
• CCG-208550
• NSC-711511
• NCGC00096070-01
• NCGC00096070-03
• NCGC00096070-04
• NCGC00096070-05
• NCGC00096070-11
• NCGC00168822-01
• 29527-66-0
• AC-34106
• SMR000386931
• CS-0022591
• A871794
• Q3629783
• SR-01000758940-3
• SR-01000758940-4
• 7-(3,7-Dimethyl-octa-2,6-dienyloxy)-chromen-2-one
• 7-[(3,7-Dimethyl-2,6-octadienyl)oxy]-(E)-Coumarin
• BRD-K85013741-001-05-9
• Coumarin, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)-
• (E)-7-(3,7-dimethylocta-2,6-dienyloxy)-2H-chromen-2-one
• 7-([(2E)-3,7-Dimethyl-2,6-octadienyl]oxy)-2H-chromen-2-one #
• 7-(3,7-Dimethyl-2,6-octadienyl)oxy-2H-1-benzopyran-2-one, 9CI
• 7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-1-benzopyran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9940	99.40%
Caco-2	+	0.8414	84.14%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6909	69.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8570	85.70%
OATP1B3 inhibitior	+	0.9098	90.98%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8944	89.44%
P-glycoprotein inhibitior	-	0.5158	51.58%
P-glycoprotein substrate	-	0.9129	91.29%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6607	66.07%
CYP2D6 substrate	-	0.8073	80.73%
CYP3A4 inhibition	-	0.7255	72.55%
CYP2C9 inhibition	+	0.7543	75.43%
CYP2C19 inhibition	+	0.9269	92.69%
CYP2D6 inhibition	-	0.5087	50.87%
CYP1A2 inhibition	+	0.9441	94.41%
CYP2C8 inhibition	-	0.7766	77.66%
CYP inhibitory promiscuity	+	0.7378	73.78%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6493	64.93%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.8353	83.53%
Skin irritation	-	0.8138	81.38%
Skin corrosion	-	0.9714	97.14%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8804	88.04%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5292	52.92%
skin sensitisation	-	0.7506	75.06%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.5899	58.99%
Acute Oral Toxicity (c)	III	0.5773	57.73%
Estrogen receptor binding	+	0.8250	82.50%
Androgen receptor binding	+	0.8315	83.15%
Thyroid receptor binding	-	0.5509	55.09%
Glucocorticoid receptor binding	+	0.6453	64.53%
Aromatase binding	+	0.7696	76.96%
PPAR gamma	+	0.7679	76.79%
Honey bee toxicity	-	0.8854	88.54%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	35481.3 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2524	P06280	Alpha-galactosidase A	14125.4 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	23900 nM	IC50	PMID: 23047230
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM	Potency	via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	31622.8 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	35481.3 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	12589.3 nM	Potency	via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	22387.2 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	70794.6 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2039	P27338	Monoamine oxidase B	98.70%	92.51%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.24%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	95.20%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.62%	99.17%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	93.67%	92.08%
CHEMBL2581	P07339	Cathepsin D	93.50%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.38%	94.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	91.85%	83.57%
CHEMBL4208	P20618	Proteasome component C5	90.82%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.59%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	84.49%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.31%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.93%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.62%	95.56%

Plants that contains it

• Aegle marmelos
• Afraegle paniculata
• Atalantia buxifolia
• Baccharis darwinii
• Baccharis eggersii
• Citrus × aurantium
• Citrus japonica
• Citrus maxima
• Citrus trifoliata
• Clausena anisum-olens
• Dictamnus albus
• Diplotaenia damavandica
• Ferula penninervis
• Ferulago brachyloba
• Geijera parviflora
• Krubera peregrina
• Metrodorea nigra
• Murraya paniculata
• Phebalium filifolium
• Phebalium stenophyllum
• Pilocarpus riedelianus
• Pleiospermium alatum
• Polygala paniculata
• Rosa transmorrisonensis
• Sinacalia tangutica
• Skimmia reevesiana
• Solidago drummondii
• Spiranthera odoratissima
• Toddalia asiatica
• Triphasia trifolia
• Zanthoxylum ailanthoides
• Zanthoxylum coco
• Zanthoxylum rhoifolium
• Zanthoxylum schinifolium

Cross-Links

• PubChem: 1550607
• NPASS: NPC180006
• ChEMBL: CHEMBL307341
• LOTUS: LTS0058299
• wikiData: Q3629783