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

Details

• Internal ID: 9427f63d-a6fb-49da-84a3-53f2ebea5c8c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2S)-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-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)O)C(=O)CC(O2)C3=C(C=C(C=C3)O)O)C(=C)C)C
• SMILES (Isomeric): CC(=CC[C@@H](CC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=C(C=C(C=C3)O)O)C(=C)C)C
• InChI: InChI=1S/C25H28O6/c1-13(2)5-6-15(14(3)4)9-18-20(28)11-21(29)24-22(30)12-23(31-25(18)24)17-8-7-16(26)10-19(17)27/h5,7-8,10-11,15,23,26-29H,3,6,9,12H2,1-2,4H3/t15-,23-/m0/s1
• InChI Key: XRYVAQQLDYTHCL-WNSKOXEYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₆
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.18858861 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 5.31
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• SCHEMBL15090973
• (2S)-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9810	98.10%
Caco-2	-	0.5808	58.08%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7230	72.30%
OATP2B1 inhibitior	-	0.7137	71.37%
OATP1B1 inhibitior	+	0.8274	82.74%
OATP1B3 inhibitior	+	0.9375	93.75%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8268	82.68%
P-glycoprotein inhibitior	+	0.6061	60.61%
P-glycoprotein substrate	+	0.5278	52.78%
CYP3A4 substrate	+	0.6209	62.09%
CYP2C9 substrate	+	0.5973	59.73%
CYP2D6 substrate	-	0.7963	79.63%
CYP3A4 inhibition	-	0.5053	50.53%
CYP2C9 inhibition	+	0.8261	82.61%
CYP2C19 inhibition	+	0.8741	87.41%
CYP2D6 inhibition	-	0.6860	68.60%
CYP1A2 inhibition	+	0.8587	85.87%
CYP2C8 inhibition	+	0.4501	45.01%
CYP inhibitory promiscuity	+	0.8921	89.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7027	70.27%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.7309	73.09%
Skin irritation	-	0.7388	73.88%
Skin corrosion	-	0.9173	91.73%
Ames mutagenesis	-	0.5637	56.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7706	77.06%
Micronuclear	-	0.5441	54.41%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.7433	74.33%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.5987	59.87%
Acute Oral Toxicity (c)	III	0.4996	49.96%
Estrogen receptor binding	+	0.8474	84.74%
Androgen receptor binding	+	0.7296	72.96%
Thyroid receptor binding	+	0.6418	64.18%
Glucocorticoid receptor binding	+	0.7857	78.57%
Aromatase binding	-	0.5132	51.32%
PPAR gamma	+	0.7720	77.20%
Honey bee toxicity	-	0.7491	74.91%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9949	99.49%

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	97.74%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.38%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.88%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.00%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	90.72%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.26%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	89.36%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.97%	89.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.73%	96.12%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.13%	95.89%
CHEMBL240	Q12809	HERG	86.73%	89.76%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.08%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.51%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.11%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.08%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.71%	95.89%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.35%	83.10%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.26%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.25%	99.15%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.22%	100.00%

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 alopecuroides
• Sophora exigua
• Sophora flavescens
• Sophora moorcroftiana
• Sophora stenophylla
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 6565899
• NPASS: NPC28683
• LOTUS: LTS0223099
• wikiData: Q104399815