Decursin

Details

• Internal ID: 440caf9c-4d35-46fe-9e63-9e92e9c6451b
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Linear pyranocoumarins
• IUPAC Name: [(3S)-2,2-dimethyl-8-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] 3-methylbut-2-enoate
• SMILES (Canonical): CC(=CC(=O)OC1CC2=C(C=C3C(=C2)C=CC(=O)O3)OC1(C)C)C
• SMILES (Isomeric): CC(=CC(=O)O[C@H]1CC2=C(C=C3C(=C2)C=CC(=O)O3)OC1(C)C)C
• InChI: InChI=1S/C19H20O5/c1-11(2)7-18(21)23-16-9-13-8-12-5-6-17(20)22-14(12)10-15(13)24-19(16,3)4/h5-8,10,16H,9H2,1-4H3/t16-/m0/s1
• InChI Key: CUKSFECWKQBVED-INIZCTEOSA-N
• Popularity: 145 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₅
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.13107373 g/mol
• Topological Polar Surface Area (TPSA): 61.80 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.38
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 5928-25-6
• (+)-Decursin
• (S)-(+)-Decursin
• UNII-E95RTO3YQR
• E95RTO3YQR
• CHEBI:4353
• CHEMBL481658
• [(3S)-2,2-dimethyl-8-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] 3-methylbut-2-enoate
• (S)-7,8-Dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo(1,2-b:5,4-b')dipyran-7-yl 3-methyl-2-butenoate
• 2-Butenoic acid, 3-methyl-, 7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo(1,2-b:5,4-b')dipyran-7-yl ester, (S)-
• (S)-2,2-dimethyl-8-oxo-2,3,4,8-tetrahydropyrano[3,2-g]chromen-3-yl 3-methylbut-2-enoate
• 2-butenoic acid, 3-methyl-, (7S)-7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-pyrano(3,2-G)-1-benzopyran-7-yl ester
• 3-methyl-2-butenoic acid, (7S)-7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-pyrano[3,2-g]-1-benzopyran-7-yl ester
• CROTONIC ACID, 3-METHYL-, ESTER WITH 7,8-DIHYDRO-7-HYDROXY-8,8-DIMETHYL-2H,6H-BENZO(1,2-B:5,4-B')DIPYRAN-2-ONE, (+)-
• AC1L9CAH
• DECURSIN [INCI]
• Decursin ((+)-Decursin)
• Ambap5928-25-6
• SCHEMBL14511556
• DTXSID90974706
• HMS3887A11
• BCP10293
• BDBM50361396
• MFCD00272154
• s9264
• ZB1887
• AKOS025149080
• CCG-267790
• AC-35119
• AS-79221
• HY-18981
• CS-0014824
• C09258
• Q27106347
• 2-Butenoic acid, 3-methyl-, (7S)-7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo[1,2-b:5,4-b']dipyran-7-yl ester
• 8,8-Dimethyl-2-oxo-7,8-dihydro-2H,6H-benzo[1,2-b:5,4-b']dipyran-7-yl 3-methylbut-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9914	99.14%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7068	70.68%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9189	91.89%
OATP1B3 inhibitior	+	0.9276	92.76%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5527	55.27%
P-glycoprotein inhibitior	+	0.6269	62.69%
P-glycoprotein substrate	-	0.5980	59.80%
CYP3A4 substrate	+	0.5787	57.87%
CYP2C9 substrate	-	0.6104	61.04%
CYP2D6 substrate	-	0.8780	87.80%
CYP3A4 inhibition	+	0.5082	50.82%
CYP2C9 inhibition	-	0.8135	81.35%
CYP2C19 inhibition	+	0.6252	62.52%
CYP2D6 inhibition	-	0.8222	82.22%
CYP1A2 inhibition	-	0.5883	58.83%
CYP2C8 inhibition	-	0.5738	57.38%
CYP inhibitory promiscuity	-	0.5089	50.89%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5296	52.96%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.7754	77.54%
Skin irritation	-	0.7419	74.19%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7336	73.36%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.6607	66.07%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5175	51.75%
Acute Oral Toxicity (c)	III	0.7246	72.46%
Estrogen receptor binding	+	0.8399	83.99%
Androgen receptor binding	+	0.6966	69.66%
Thyroid receptor binding	-	0.5485	54.85%
Glucocorticoid receptor binding	+	0.7253	72.53%
Aromatase binding	-	0.5274	52.74%
PPAR gamma	+	0.6036	60.36%
Honey bee toxicity	-	0.7211	72.11%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9946	99.46%

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	98.93%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.10%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.37%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	95.45%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.33%	96.09%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	89.45%	85.30%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.52%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.79%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.42%	92.94%
CHEMBL3401	O75469	Pregnane X receptor	85.30%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.29%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.08%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.53%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.45%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	82.76%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.75%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.93%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.64%	95.89%

Plants that contains it

• Angelica acutiloba
• Angelica decursiva
• Angelica gigas
• Angelica glauca
• Angelica sinensis
• Phlojodicarpus villosus
• Prangos ferulacea
• Saposhnikovia divaricata
• Scutellaria lateriflora

Cross-Links

• PubChem: 442126
• NPASS: NPC207002
• LOTUS: LTS0017773
• wikiData: Q27106347