(2S)-2-(2,4-Dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-8-[(2R)-5-hydroxy-5-methyl-2-(1-methylethenyl)hexyl]-4H-1-benzopyran-4-one

Details

• Internal ID: 57476b58-2e2c-4d8a-8a01-7cfccfb222f5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2S)-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2R)-5-hydroxy-5-methyl-2-prop-1-en-2-ylhexyl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=C)C(CCC(C)(C)O)CC1=C2C(=C(C=C1O)O)C(=O)CC(O2)C3=C(C=C(C=C3)O)O
• SMILES (Isomeric): CC(=C)[C@H](CCC(C)(C)O)CC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=C(C=C(C=C3)O)O
• InChI: InChI=1S/C25H30O7/c1-13(2)14(7-8-25(3,4)31)9-17-19(28)11-20(29)23-21(30)12-22(32-24(17)23)16-6-5-15(26)10-18(16)27/h5-6,10-11,14,22,26-29,31H,1,7-9,12H2,2-4H3/t14-,22+/m1/s1
• InChI Key: PFTQIVMILQKDQN-PEBXRYMYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₇
• Molecular Weight: 442.50 g/mol
• Exact Mass: 442.19915329 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.50
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• CHEMBL454647
• DTXSID701102872
• 52483-01-9
• (2S)-2-(2,4-Dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-8-[(2R)-5-hydroxy-5-methyl-2-(1-methylethenyl)hexyl]-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9838	98.38%
Caco-2	-	0.6364	63.64%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7086	70.86%
OATP2B1 inhibitior	-	0.7133	71.33%
OATP1B1 inhibitior	+	0.8407	84.07%
OATP1B3 inhibitior	+	0.9039	90.39%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7926	79.26%
P-glycoprotein inhibitior	-	0.4646	46.46%
P-glycoprotein substrate	+	0.6473	64.73%
CYP3A4 substrate	+	0.6420	64.20%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8198	81.98%
CYP3A4 inhibition	+	0.6318	63.18%
CYP2C9 inhibition	-	0.5446	54.46%
CYP2C19 inhibition	+	0.5287	52.87%
CYP2D6 inhibition	-	0.8729	87.29%
CYP1A2 inhibition	+	0.6131	61.31%
CYP2C8 inhibition	+	0.4559	45.59%
CYP inhibitory promiscuity	+	0.5314	53.14%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7012	70.12%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.7734	77.34%
Skin irritation	-	0.7011	70.11%
Skin corrosion	-	0.9241	92.41%
Ames mutagenesis	-	0.5637	56.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7133	71.33%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7734	77.34%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.5853	58.53%
Acute Oral Toxicity (c)	III	0.3821	38.21%
Estrogen receptor binding	+	0.8366	83.66%
Androgen receptor binding	+	0.7432	74.32%
Thyroid receptor binding	+	0.5785	57.85%
Glucocorticoid receptor binding	+	0.7462	74.62%
Aromatase binding	+	0.5711	57.11%
PPAR gamma	+	0.7382	73.82%
Honey bee toxicity	-	0.7631	76.31%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9974	99.74%

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	97.93%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.80%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.84%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.69%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.07%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.84%	89.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.64%	96.12%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.01%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.94%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.88%	93.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.97%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.73%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.16%	99.17%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.33%	90.93%
CHEMBL1951	P21397	Monoamine oxidase A	84.23%	91.49%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.98%	95.89%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.38%	100.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.10%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.90%	99.23%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.22%	85.00%
CHEMBL236	P41143	Delta opioid receptor	81.18%	99.35%
CHEMBL2535	P11166	Glucose transporter	80.45%	98.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.41%	90.71%

Plants that contains it

• Aquilaria malaccensis
• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euphorbia jolkinii
• Faramea multiflora
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Linnaea chinensis
• Lythrum salicaria
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora flavescens
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 44563159
• NPASS: NPC131579
• ChEMBL: CHEMBL454647
• LOTUS: LTS0007492
• wikiData: Q104666957