2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: c36d0864-6db8-445a-a1c1-570dc835846c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O[C@H]4C([C@H]([C@@H](C(O4)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)31-8-4-11(25)14-12(5-8)32-20(18(29)16(14)27)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,19,21-26,28-30H,6H2/t13?,15-,17+,19?,21-/m1/s1
• InChI Key: BBFYUPYFXSSMNV-LQPIGNGESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₂
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.09547607 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.54
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

• LMPK12112179

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9383	93.83%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5975	59.75%
OATP1B1 inhibitior	+	0.9340	93.40%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5647	56.47%
P-glycoprotein inhibitior	-	0.7556	75.56%
P-glycoprotein substrate	-	0.7868	78.68%
CYP3A4 substrate	+	0.6238	62.38%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	+	0.8846	88.46%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8623	86.23%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.7636	76.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4439	44.39%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7196	71.96%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9020	90.20%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7414	74.14%
Androgen receptor binding	+	0.6723	67.23%
Thyroid receptor binding	+	0.5711	57.11%
Glucocorticoid receptor binding	+	0.6425	64.25%
Aromatase binding	+	0.5359	53.59%
PPAR gamma	+	0.8231	82.31%
Honey bee toxicity	-	0.7224	72.24%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.8218	82.18%

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	99.73%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.91%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.09%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.56%	99.15%
CHEMBL2581	P07339	Cathepsin D	95.16%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.93%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.09%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	90.87%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.35%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.80%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.38%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.60%	94.45%
CHEMBL3194	P02766	Transthyretin	88.49%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.51%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.20%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.42%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.16%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.97%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.09%	90.71%

Plants that contains it

• Acacia latifolia
• Achillea arabica
• Achyrocline alata
• Anaxagorea luzonensis
• Anthemis cotula
• Aristolochia cucurbitifolia
• Artemisia annua
• Asteriscus graveolens
• Astragalus lagopoides
• Bahiopsis tomentosa
• Calanticaria greggii
• Camellia sinensis
• Caragana aurantiaca
• Carthamus lanatus
• Carthamus tinctorius
• Centaurea cyanus
• Daniellia oliveri
• Datura ceratocaula
• Dendrobium bigibbum
• Dendroviguiera eriophora
• Dittrichia viscosa subsp. viscosa
• Fallopia dumetorum
• Galinsoga quadriradiata
• Geranium robertianum
• Gossypium arboreum
• Gossypium hirsutum
• Gutierrezia grandis
• Gutierrezia microcephala
• Helianthus annuus
• Helianthus heterophyllus
• Helichrysum stoechas
• Hibiscus moscheutos
• Ipomoea nil
• Kummerowia striata
• Maclura tricuspidata
• Omalotheca sylvatica
• Onobrychis cornuta
• Pelargonium reniforme
• Persicaria lapathifolia
• Podocarpus nivalis
• Pongamia pinnata
• Porophyllum obscurum
• Prunus davidiana
• Punica granatum
• Reseda muricata
• Ripariosida hermaphrodita
• Robinsonia thurifera
• Rosa gallica
• Russowia sogdiana
• Salix acutifolia
• Salix alba
• Salix purpurea
• Senecio glaucus subsp. coronopifolius
• Senna italica
• Sonchus oleraceus
• Sorbaria kirilowii
• Sorbaria sorbifolia
• Spathodea campanulata
• Trigonella foenum-graecum
• Ulex europaeus
• Zosima absinthifolia

Cross-Links

• PubChem: 44259225
• NPASS: NPC310740
• LOTUS: LTS0188893
• wikiData: Q104249897