Orobol 8-C-glucoside

Details

• Internal ID: 0c2ab8d8-6fad-4b07-9263-448ebf2d88a2
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid C-glycosides
• IUPAC Name: 3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=COC3=C(C2=O)C(=CC(=C3C4C(C(C(C(O4)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=COC3=C(C2=O)C(=CC(=C3[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O11/c22-5-13-17(28)18(29)19(30)21(32-13)15-12(26)4-11(25)14-16(27)8(6-31-20(14)15)7-1-2-9(23)10(24)3-7/h1-4,6,13,17-19,21-26,28-30H,5H2/t13-,17-,18+,19-,21+/m1/s1
• InChI Key: FONGWVNORDOJFQ-FFYOZGDPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.10056145 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.20
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 3

Synonyms

• J1.982.119F

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6665	66.65%
Caco-2	-	0.9391	93.91%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5728	57.28%
OATP2B1 inhibitior	+	0.5924	59.24%
OATP1B1 inhibitior	+	0.8953	89.53%
OATP1B3 inhibitior	+	0.9709	97.09%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5280	52.80%
P-glycoprotein inhibitior	-	0.6982	69.82%
P-glycoprotein substrate	-	0.8863	88.63%
CYP3A4 substrate	+	0.5715	57.15%
CYP2C9 substrate	-	0.6301	63.01%
CYP2D6 substrate	-	0.8452	84.52%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9240	92.40%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.8355	83.55%
CYP2C8 inhibition	+	0.5968	59.68%
CYP inhibitory promiscuity	-	0.7806	78.06%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7252	72.52%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.7365	73.65%
Skin irritation	-	0.7691	76.91%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.5601	56.01%
Human Ether-a-go-go-Related Gene inhibition	-	0.4190	41.90%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	+	0.5054	50.54%
skin sensitisation	-	0.8683	86.83%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5962	59.62%
Acute Oral Toxicity (c)	IV	0.3746	37.46%
Estrogen receptor binding	+	0.6680	66.80%
Androgen receptor binding	+	0.7075	70.75%
Thyroid receptor binding	+	0.5837	58.37%
Glucocorticoid receptor binding	+	0.6414	64.14%
Aromatase binding	-	0.4884	48.84%
PPAR gamma	+	0.6923	69.23%
Honey bee toxicity	-	0.7887	78.87%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.6921	69.21%

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	99.45%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.28%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.74%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.59%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.23%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.19%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.90%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.21%	96.21%
CHEMBL3401	O75469	Pregnane X receptor	85.08%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.52%	86.92%

Plants that contains it

• Calicotome villosa
• Dalbergia nitidula
• Genista pichisermolliana
• Ipomoea muricata

Cross-Links

• PubChem: 21676216
• NPASS: NPC215827
• LOTUS: LTS0001218
• wikiData: Q104998850