Decursinol

Details

• Internal ID: b5c6ec61-4e76-4f74-98ae-3ade9ddc5c0c
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Linear pyranocoumarins
• IUPAC Name: (3S)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
• SMILES (Canonical): CC1(C(CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O)C
• SMILES (Isomeric): CC1([C@H](CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O)C
• InChI: InChI=1S/C14H14O4/c1-14(2)12(15)6-9-5-8-3-4-13(16)17-10(8)7-11(9)18-14/h3-5,7,12,15H,6H2,1-2H3/t12-/m0/s1
• InChI Key: BGXFQDFSVDZUIW-LBPRGKRZSA-N
• Popularity: 256 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.26 g/mol
• Exact Mass: 246.08920892 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 23458-02-8
• (+)-Decursinol
• Smirino
• Smyrinol
• SFE decursinol
• Decursinol [INCI]
• (S)-(+)-decursinol
• UNII-UBI4YB704B
• UBI4YB704B
• CHEBI:4354
• CHEMBL481657
• 2H,6H-Benzo(1,2-b:5,4-b')dipyran-2-one, 7,8-dihydro-7-hydroxy-8,8-dimethyl-, (S)-
• 2H,6H-Benzo(1,2-b:5,4-b')dipyran-2-one, 7,8-dihydro-7-hydroxy-8,8-dimethyl-, (S)-(+)-
• (3S)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
• (S)-7-hydroxy-8,8-dimethyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-2-one
• (S)-7-Hydroxy-8,8-dimethyl-7,8-dihydropyrano(3,2-g)chromen-2(6H)-one
• (S)-7-hydroxy-8,8-dimethyl-7,8-dihydropyrano[3,2-g]chromen-2(6H)-one
• MLS002472906
• SCHEMBL14105325
• DTXSID70178008
• BGXFQDFSVDZUIW-LBPRGKRZSA-N
• HMS2192M06
• BCP24688
• HY-N4109
• BDBM50259817
• MFCD06636641
• AKOS008901445
• SMR001397017
• WS-01956
• CS-0032117
• C09259
• D85508
• Q27068163
• (7S)-7-hydroxy-8,8-dimethyl-2H,6H,7H,8H-pyrano[3,2-g]chromen-2-one
• 7-Hydroxy-8,8-dimethyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-2-one #
• (7S)-7,8-dihydro-7-hydroxy-8,8-dimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-2-one
• (7S)-7-hydroxy-8,8-dimethyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-2-one
• 2H,6H-Benzo[1,2-b:5,4-b']dipyran-2-one, 7,8-dihydro-7-hydroxy-8,8-dimethyl-, (7S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9869	98.69%
Caco-2	+	0.7971	79.71%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6546	65.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8855	88.55%
OATP1B3 inhibitior	+	0.9539	95.39%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8483	84.83%
P-glycoprotein inhibitior	-	0.9390	93.90%
P-glycoprotein substrate	-	0.7458	74.58%
CYP3A4 substrate	-	0.5267	52.67%
CYP2C9 substrate	-	0.6562	65.62%
CYP2D6 substrate	-	0.7813	78.13%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9341	93.41%
CYP2C19 inhibition	-	0.9345	93.45%
CYP2D6 inhibition	-	0.8673	86.73%
CYP1A2 inhibition	-	0.7655	76.55%
CYP2C8 inhibition	-	0.8382	83.82%
CYP inhibitory promiscuity	-	0.9657	96.57%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6022	60.22%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.7523	75.23%
Skin irritation	-	0.6201	62.01%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4200	42.00%
Micronuclear	+	0.5118	51.18%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.7729	77.29%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.5942	59.42%
Acute Oral Toxicity (c)	III	0.7058	70.58%
Estrogen receptor binding	+	0.7108	71.08%
Androgen receptor binding	-	0.4930	49.30%
Thyroid receptor binding	-	0.5444	54.44%
Glucocorticoid receptor binding	+	0.6073	60.73%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7085	70.85%
Honey bee toxicity	-	0.9072	90.72%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9331	93.31%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	28000 nM	IC50	PMID: 11374978

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.89%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.91%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.81%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.88%	94.45%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	88.35%	85.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.31%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.11%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.03%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	86.89%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.18%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.40%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	82.24%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.73%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.65%	86.33%

Plants that contains it

• Aegle marmelos
• Angelica acutiloba
• Angelica decursiva
• Angelica gigas
• Angelica sinensis
• Phlojodicarpus villosus
• Smyrniopsis aucheri

Cross-Links

• PubChem: 442127
• NPASS: NPC78746
• ChEMBL: CHEMBL481657
• LOTUS: LTS0073597
• wikiData: Q27068163