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

Details

• Internal ID: 570e6e48-b372-4349-a526-9a6307e8ecc2
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: (2S,3S)-3-hydroxy-2-[(3E,7R)-7-hydroxy-4,8-dimethylnona-3,8-dienyl]-2-methyl-3,4-dihydropyrano[2,3-b]chromen-5-one
• SMILES (Canonical): CC(=C)C(CCC(=CCCC1(C(CC2=C(O1)OC3=CC=CC=C3C2=O)O)C)C)O
• SMILES (Isomeric): CC(=C)[C@@H](CC/C(=C/CC[C@]1([C@H](CC2=C(O1)OC3=CC=CC=C3C2=O)O)C)/C)O
• InChI: InChI=1S/C24H30O5/c1-15(2)19(25)12-11-16(3)8-7-13-24(4)21(26)14-18-22(27)17-9-5-6-10-20(17)28-23(18)29-24/h5-6,8-10,19,21,25-26H,1,7,11-14H2,2-4H3/b16-8+/t19-,21+,24+/m1/s1
• InChI Key: HFSYZZHJCCXGHB-WHPZNWOPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₅
• Molecular Weight: 398.50 g/mol
• Exact Mass: 398.20932405 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.29
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9632	96.32%
Caco-2	-	0.6958	69.58%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7009	70.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8843	88.43%
OATP1B3 inhibitior	-	0.2409	24.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9333	93.33%
P-glycoprotein inhibitior	+	0.6174	61.74%
P-glycoprotein substrate	+	0.6022	60.22%
CYP3A4 substrate	+	0.6946	69.46%
CYP2C9 substrate	-	0.6442	64.42%
CYP2D6 substrate	-	0.7280	72.80%
CYP3A4 inhibition	-	0.8104	81.04%
CYP2C9 inhibition	-	0.8319	83.19%
CYP2C19 inhibition	-	0.6801	68.01%
CYP2D6 inhibition	-	0.9371	93.71%
CYP1A2 inhibition	-	0.5343	53.43%
CYP2C8 inhibition	-	0.6059	60.59%
CYP inhibitory promiscuity	-	0.9057	90.57%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6284	62.84%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9216	92.16%
Skin irritation	-	0.5760	57.60%
Skin corrosion	-	0.9336	93.36%
Ames mutagenesis	-	0.7537	75.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8588	85.88%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8161	81.61%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6283	62.83%
Acute Oral Toxicity (c)	I	0.3848	38.48%
Estrogen receptor binding	+	0.7258	72.58%
Androgen receptor binding	+	0.6754	67.54%
Thyroid receptor binding	+	0.5671	56.71%
Glucocorticoid receptor binding	+	0.7760	77.60%
Aromatase binding	+	0.6014	60.14%
PPAR gamma	+	0.7617	76.17%
Honey bee toxicity	-	0.7097	70.97%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.70%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.24%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.07%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.04%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.43%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.34%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.69%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.20%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.16%	94.45%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.31%	90.08%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.81%	94.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.40%	97.09%

Plants that contains it

• Ferula communis

Cross-Links

• PubChem: 163192985
• LOTUS: LTS0007598
• wikiData: Q105027526