(2S)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2S)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one

Details

• Internal ID: 520c0588-1a83-44db-944c-c7b906ac9052
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2S)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2S)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC(CC1=C2C(=C(C=C1O)OC)C(=O)CC(O2)C3=C(C=C(C=C3)O)OC)C(=C)C)C
• SMILES (Isomeric): CC(=CC[C@@H](CC1=C2C(=C(C=C1O)OC)C(=O)C[C@H](O2)C3=C(C=C(C=C3)O)OC)C(=C)C)C
• InChI: InChI=1S/C27H32O6/c1-15(2)7-8-17(16(3)4)11-20-21(29)13-25(32-6)26-22(30)14-24(33-27(20)26)19-10-9-18(28)12-23(19)31-5/h7,9-10,12-13,17,24,28-29H,3,8,11,14H2,1-2,4-6H3/t17-,24-/m0/s1
• InChI Key: KTAQQSUPNZAWEY-XDHUDOTRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₆
• Molecular Weight: 452.50 g/mol
• Exact Mass: 452.21988874 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.91
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.5375	53.75%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8008	80.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8466	84.66%
OATP1B3 inhibitior	+	0.8539	85.39%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9476	94.76%
P-glycoprotein inhibitior	+	0.8228	82.28%
P-glycoprotein substrate	+	0.5112	51.12%
CYP3A4 substrate	+	0.6536	65.36%
CYP2C9 substrate	-	0.7880	78.80%
CYP2D6 substrate	-	0.7350	73.50%
CYP3A4 inhibition	-	0.7153	71.53%
CYP2C9 inhibition	+	0.7785	77.85%
CYP2C19 inhibition	+	0.9169	91.69%
CYP2D6 inhibition	-	0.7029	70.29%
CYP1A2 inhibition	+	0.7535	75.35%
CYP2C8 inhibition	+	0.6522	65.22%
CYP inhibitory promiscuity	+	0.8659	86.59%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.7241	72.41%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.8255	82.55%
Skin irritation	-	0.7957	79.57%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.5537	55.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7078	70.78%
Micronuclear	-	0.5041	50.41%
Hepatotoxicity	+	0.7302	73.02%
skin sensitisation	-	0.8007	80.07%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5113	51.13%
Acute Oral Toxicity (c)	III	0.6421	64.21%
Estrogen receptor binding	+	0.8620	86.20%
Androgen receptor binding	+	0.6477	64.77%
Thyroid receptor binding	+	0.6769	67.69%
Glucocorticoid receptor binding	+	0.8694	86.94%
Aromatase binding	+	0.6236	62.36%
PPAR gamma	+	0.6986	69.86%
Honey bee toxicity	-	0.6898	68.98%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9925	99.25%

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	98.55%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.91%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.21%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.47%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.94%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.76%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.59%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.55%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.41%	85.14%
CHEMBL2535	P11166	Glucose transporter	88.39%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	87.97%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.57%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.23%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.16%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.74%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.07%	99.15%
CHEMBL1902	P62942	FK506-binding protein 1A	82.26%	97.05%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.12%	94.00%
CHEMBL4040	P28482	MAP kinase ERK2	81.27%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.86%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.70%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.38%	89.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.36%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.19%	97.14%

Plants that contains it

• 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: 60039901
• NPASS: NPC61457