Khelloside

Details

• Internal ID: 792956d8-a585-4d7e-a04f-e833a9578b6f
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Chromones > Furanochromones
• IUPAC Name: 4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]furo[3,2-g]chromen-5-one
• SMILES (Canonical): COC1=C2C=COC2=CC3=C1C(=O)C=C(O3)COC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=C2C=COC2=CC3=C1C(=O)C=C(O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C19H20O10/c1-25-18-9-2-3-26-11(9)5-12-14(18)10(21)4-8(28-12)7-27-19-17(24)16(23)15(22)13(6-20)29-19/h2-5,13,15-17,19-20,22-24H,6-7H2,1H3/t13-,15-,16+,17-,19-/m1/s1
• InChI Key: SJRACCTZSAUMGO-WIMVFMHDSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₁₀
• Molecular Weight: 408.40 g/mol
• Exact Mass: 408.10564683 g/mol
• Topological Polar Surface Area (TPSA): 148.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.14
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• Khellol glucoside
• Khellinin
• 17226-75-4
• Khellosidum
• Khellenin
• Quelosido
• Khellolglucoside
• UNII-ZX4FRZ5WJP
• ZX4FRZ5WJP
• Khellol beta-D-glucopyranoside
• EINECS 241-263-3
• NSC 82907
• NSC-82907
• DTXSID40878402
• 4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]furo[3,2-g]chromen-5-one
• 7-Hydroxymethyl-4-methoxy-5H-furo(3,2-g)(1)benzopyran-5-one glucoside
• 5H-Furo(3,2-g)(1)benzopyran-5-one, 7-((beta-D-glucopyranosyloxy)methyl)-4-methoxy-
• Glucopyranoside, (4-methoxy-5-oxo-5H-furo(3,2-g)(1)benzopyran-7-yl)methyl, beta-D-
• 4-Methoxy-7-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-5H-furo[3,2-g]chromen-5-one
• Khelloside [INN:DCF]
• Khellosidum [INN-Latin]
• Quelosido [INN-Spanish]
• AC1L9C0T
• kelosido
• KHELLOSIDE [INN]
• SureCN2110571
• KHELLOL GLUCOSIDE [MI]
• Khelloside (Khellol-glucoside)
• CHEBI:6134
• SCHEMBL2110571
• CHEMBL3989710
• MolPort-001-740-502
• DTXCID801016450
• ZINC04097843
• AKOS022181400
• Khelloside, >=95% (LC/MS-ELSD)
• NCGC00385505-01
• C09011
• 4-methoxy-7-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5H-furo[3,2-g]chromen-5-one
• 4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]furo[3,2-g]chromen-5-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5335	53.35%
Caco-2	-	0.8360	83.60%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6417	64.17%
OATP2B1 inhibitior	-	0.8489	84.89%
OATP1B1 inhibitior	+	0.8876	88.76%
OATP1B3 inhibitior	+	0.9752	97.52%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6078	60.78%
P-glycoprotein inhibitior	-	0.7429	74.29%
P-glycoprotein substrate	-	0.7021	70.21%
CYP3A4 substrate	+	0.5799	57.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8436	84.36%
CYP3A4 inhibition	-	0.8975	89.75%
CYP2C9 inhibition	-	0.8889	88.89%
CYP2C19 inhibition	-	0.7892	78.92%
CYP2D6 inhibition	-	0.8810	88.10%
CYP1A2 inhibition	-	0.8996	89.96%
CYP2C8 inhibition	+	0.4713	47.13%
CYP inhibitory promiscuity	-	0.6260	62.60%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5178	51.78%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9667	96.67%
Skin irritation	-	0.8301	83.01%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5262	52.62%
Micronuclear	+	0.5833	58.33%
Hepatotoxicity	-	0.7074	70.74%
skin sensitisation	-	0.8897	88.97%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.9154	91.54%
Acute Oral Toxicity (c)	III	0.7818	78.18%
Estrogen receptor binding	+	0.8650	86.50%
Androgen receptor binding	+	0.7373	73.73%
Thyroid receptor binding	+	0.5440	54.40%
Glucocorticoid receptor binding	+	0.7333	73.33%
Aromatase binding	+	0.6004	60.04%
PPAR gamma	+	0.7206	72.06%
Honey bee toxicity	-	0.7832	78.32%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.3739	37.39%

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	99.09%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.09%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.18%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.03%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.01%	98.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	89.76%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.60%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.95%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.24%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.92%	96.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.29%	94.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.84%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.08%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.66%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.55%	94.45%

Plants that contains it

• Visnaga daucoides

Cross-Links

• PubChem: 441966
• LOTUS: LTS0184245
• wikiData: Q1740621