Prim-O-glucosylcimifugin

Details

• Internal ID: 1fef6988-1538-4aa5-b6ef-5da9b46efbda
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Chromones > Furanochromones
• IUPAC Name: (2S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydrofuro[3,2-g]chromen-5-one
• SMILES (Canonical): CC(C)(C1CC2=C(O1)C=C3C(=C2OC)C(=O)C=C(O3)COC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): CC(C)([C@@H]1CC2=C(O1)C=C3C(=C2OC)C(=O)C=C(O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C22H28O11/c1-22(2,28)15-5-10-12(32-15)6-13-16(20(10)29-3)11(24)4-9(31-13)8-30-21-19(27)18(26)17(25)14(7-23)33-21/h4,6,14-15,17-19,21,23,25-28H,5,7-8H2,1-3H3/t14-,15+,17-,18+,19-,21-/m1/s1
• InChI Key: XIUVHOSBSDYXRG-UVTAEQIVSA-N
• Popularity: 35 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₁₁
• Molecular Weight: 468.40 g/mol
• Exact Mass: 468.16316171 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -0.81
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• 80681-45-4
• Cimifugin 7-glucoside
• CIMIFUGINBETA-D-GLUCOPYRANOSIDE
• (2S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydrofuro[3,2-g]chromen-5-one
• Cimifugin beta-D-glucopyranoside
• (S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-2H-furo[3,2-g]chromen-5(3H)-one
• 5H-Furo[3,2-g][1]benzopyran-5-one,7-[(b-D-glucopyranosyloxy)methyl]-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-4-methoxy-, (S)-
• prim-O-glucosyl cimifugin
• prim-O-b-D-Glucosylcimifugin
• MLS002472946
• CHEMBL1734606
• DTXSID90554764
• CHEBI:187279
• HMS2196A10
• HY-N0635
• MFCD09037394
• s9029
• ZB1876
• AKOS037514796
• CCG-269432
• CS-3795
• AC-34700
• AS-76831
• SMR001397054
• G0535
• Q-100837
• (2S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydrouro[3,2-g]chromen-5-one
• [(2S)-2-(2-Hydroxypropan-2-yl)-4-methoxy-5-oxo-2,3-dihydro-5H-furo[3,2-g][1]benzopyran-7-yl]methyl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6763	67.63%
Caco-2	-	0.7947	79.47%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6524	65.24%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.8759	87.59%
OATP1B3 inhibitior	+	0.9473	94.73%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7032	70.32%
P-glycoprotein inhibitior	-	0.5597	55.97%
P-glycoprotein substrate	-	0.6676	66.76%
CYP3A4 substrate	+	0.6330	63.30%
CYP2C9 substrate	-	0.8312	83.12%
CYP2D6 substrate	-	0.8450	84.50%
CYP3A4 inhibition	-	0.9150	91.50%
CYP2C9 inhibition	-	0.8511	85.11%
CYP2C19 inhibition	-	0.8204	82.04%
CYP2D6 inhibition	-	0.9197	91.97%
CYP1A2 inhibition	-	0.7243	72.43%
CYP2C8 inhibition	+	0.4506	45.06%
CYP inhibitory promiscuity	-	0.7623	76.23%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5929	59.29%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9424	94.24%
Skin irritation	-	0.8132	81.32%
Skin corrosion	-	0.9460	94.60%
Ames mutagenesis	+	0.5663	56.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7511	75.11%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.8072	80.72%
skin sensitisation	-	0.8712	87.12%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8607	86.07%
Acute Oral Toxicity (c)	III	0.6351	63.51%
Estrogen receptor binding	+	0.7567	75.67%
Androgen receptor binding	+	0.6215	62.15%
Thyroid receptor binding	-	0.5407	54.07%
Glucocorticoid receptor binding	+	0.6757	67.57%
Aromatase binding	+	0.5767	57.67%
PPAR gamma	+	0.5927	59.27%
Honey bee toxicity	-	0.7842	78.42%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8918	89.18%

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	99.39%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.10%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.20%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.17%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	92.85%	94.73%
CHEMBL2581	P07339	Cathepsin D	92.43%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.68%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.70%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.04%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.41%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.77%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.84%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.64%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.28%	86.92%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.47%	96.77%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.77%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.95%	95.89%

Plants that contains it

• Angelica japonica
• Diplolophium buchananii
• Eranthis hyemalis
• Saposhnikovia divaricata
• Styphnolobium japonicum

Cross-Links

• PubChem: 14034912
• NPASS: NPC17521
• LOTUS: LTS0276305
• wikiData: Q72502158