(2S,3S)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-3-hydroxy-2-methyl-3,4-dihydropyrano[2,3-b]chromen-5-one

Details

• Internal ID: 7c6be83f-101d-48e1-bbdc-e79d085ed12b
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: (2S,3S)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-3-hydroxy-2-methyl-3,4-dihydropyrano[2,3-b]chromen-5-one
• SMILES (Canonical): CC(=CCCC(=CCCC1(C(CC2=C(O1)OC3=CC=CC=C3C2=O)O)C)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC[C@]1([C@H](CC2=C(O1)OC3=CC=CC=C3C2=O)O)C)/C)C
• InChI: InChI=1S/C24H30O4/c1-16(2)9-7-10-17(3)11-8-14-24(4)21(25)15-19-22(26)18-12-5-6-13-20(18)27-23(19)28-24/h5-6,9,11-13,21,25H,7-8,10,14-15H2,1-4H3/b17-11+/t21-,24-/m0/s1
• InChI Key: ILNBVBZHKDOGTR-SXGPKUQFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₄
• Molecular Weight: 382.50 g/mol
• Exact Mass: 382.21440943 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.32
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9832	98.32%
Caco-2	-	0.6133	61.33%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7689	76.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8862	88.62%
OATP1B3 inhibitior	-	0.2641	26.41%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9102	91.02%
P-glycoprotein inhibitior	+	0.7329	73.29%
P-glycoprotein substrate	-	0.5567	55.67%
CYP3A4 substrate	+	0.6587	65.87%
CYP2C9 substrate	-	0.6442	64.42%
CYP2D6 substrate	-	0.7280	72.80%
CYP3A4 inhibition	-	0.7733	77.33%
CYP2C9 inhibition	-	0.7445	74.45%
CYP2C19 inhibition	-	0.5535	55.35%
CYP2D6 inhibition	-	0.9186	91.86%
CYP1A2 inhibition	-	0.5347	53.47%
CYP2C8 inhibition	-	0.6111	61.11%
CYP inhibitory promiscuity	-	0.8906	89.06%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6556	65.56%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.9352	93.52%
Skin irritation	-	0.6224	62.24%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7991	79.91%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8058	80.58%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.5681	56.81%
Acute Oral Toxicity (c)	III	0.4554	45.54%
Estrogen receptor binding	+	0.8285	82.85%
Androgen receptor binding	+	0.6713	67.13%
Thyroid receptor binding	-	0.4916	49.16%
Glucocorticoid receptor binding	+	0.6591	65.91%
Aromatase binding	+	0.7315	73.15%
PPAR gamma	+	0.8129	81.29%
Honey bee toxicity	-	0.7804	78.04%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9971	99.71%

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	99.65%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.21%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.17%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.22%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.82%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.80%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.55%	94.73%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.16%	92.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.79%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.18%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.04%	86.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.68%	90.08%

Plants that contains it

• Ferula communis

Cross-Links

• PubChem: 14630586
• LOTUS: LTS0139002
• wikiData: Q104666909