Calceolarioside B

Details

• Internal ID: a4322b16-8efa-46e7-81c8-e553e869417f
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=C(C=C1CCOC2C(C(C(C(O2)COC(=O)C=CC3=CC(=C(C=C3)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1CCO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O)O)O)O
• InChI: InChI=1S/C23H26O11/c24-14-4-1-12(9-16(14)26)3-6-19(28)33-11-18-20(29)21(30)22(31)23(34-18)32-8-7-13-2-5-15(25)17(27)10-13/h1-6,9-10,18,20-27,29-31H,7-8,11H2/b6-3+/t18-,20-,21+,22-,23-/m1/s1
• InChI Key: LFKQVVDFNHDYNK-FOXCETOMSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₁₁
• Molecular Weight: 478.40 g/mol
• Exact Mass: 478.14751164 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.13
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 105471-98-5
• Desrhamnosyl isoacteoside
• Calceorioside B
• Nuomioside A
• CHEMBL518414
• [(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CHEBI:68345
• CalceolariosideB
• Calceolarioside-B
• D0W7JA
• MEGxp0_000508
• ACon1_000407
• DTXSID70414938
• HY-N0539
• BDBM50269516
• MFCD22125003
• s9196
• AKOS016010662
• CCG-269526
• NCGC00169106-01
• AC-34505
• MS-28877
• CS-0009070
• A895998
• Q27136842
• 3,4-Dihydroxyphenethyl 6-O-[3-(3,4-dihydroxyphenyl)propenoyl]-beta-D-glucopyranoside
• [(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxy-tetrahydropyran-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 2-(3,4-Dihydroxyphenyl)ethyl 6-O-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-beta-D-glucopyranoside
• b-D-Glucopyranoside,2-(3,4-dihydroxyphenyl)ethyl, 6-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate];Calceolarioside B
• beta-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 6-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]-
• NCGC00169106-02![(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6933	69.33%
Caco-2	-	0.8938	89.38%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7695	76.95%
OATP2B1 inhibitior	-	0.7112	71.12%
OATP1B1 inhibitior	+	0.9024	90.24%
OATP1B3 inhibitior	+	0.9235	92.35%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5974	59.74%
P-glycoprotein inhibitior	-	0.5997	59.97%
P-glycoprotein substrate	-	0.8905	89.05%
CYP3A4 substrate	+	0.5825	58.25%
CYP2C9 substrate	-	0.8026	80.26%
CYP2D6 substrate	-	0.8595	85.95%
CYP3A4 inhibition	-	0.8531	85.31%
CYP2C9 inhibition	-	0.5814	58.14%
CYP2C19 inhibition	-	0.7090	70.90%
CYP2D6 inhibition	-	0.8795	87.95%
CYP1A2 inhibition	-	0.8123	81.23%
CYP2C8 inhibition	+	0.6823	68.23%
CYP inhibitory promiscuity	-	0.6635	66.35%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6621	66.21%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8948	89.48%
Skin irritation	-	0.8358	83.58%
Skin corrosion	-	0.9576	95.76%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3709	37.09%
Micronuclear	-	0.5967	59.67%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.7851	78.51%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9331	93.31%
Acute Oral Toxicity (c)	III	0.7165	71.65%
Estrogen receptor binding	+	0.6657	66.57%
Androgen receptor binding	+	0.6039	60.39%
Thyroid receptor binding	+	0.5313	53.13%
Glucocorticoid receptor binding	+	0.5381	53.81%
Aromatase binding	-	0.5494	54.94%
PPAR gamma	+	0.5902	59.02%
Honey bee toxicity	-	0.7404	74.04%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8964	89.64%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1978	P11511	Cytochrome P450 19A1	35300 nM	IC50	PMID: 21261296
CHEMBL299	P17252	Protein kinase C alpha	4600 nM	IC50	PMID: 9834166

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.44%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.60%	91.49%
CHEMBL3194	P02766	Transthyretin	95.71%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.68%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.00%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.84%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.78%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.92%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.70%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.16%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.15%	86.92%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	85.03%	96.37%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.00%	96.95%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.00%	80.78%
CHEMBL2581	P07339	Cathepsin D	83.85%	98.95%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.84%	85.31%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.50%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.74%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.05%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.90%	94.62%

Plants that contains it

• Akebia quinata
• Akebia trifoliata
• Allium stipitatum
• Alstonia longifolia
• Angiopteris evecta
• Artemisia argentea
• Asphodeline damascena
• Brodiaea californica
• Calceolaria cavanillesii
• Calceolaria hypericina
• Cassinopsis madagascariensis
• Cyathula tomentosa
• Digitalis purpurea
• Echinostephia aculeata
• Eucalyptus kitsoniana
• Euphorbia antiquorum
• Exochorda racemosa subsp. giraldii
• Fraxinus insularis
• Fraxinus ornus
• Hemionitis lemmonii
• Himantoglossum hircinum
• Kopsia arborea
• Lepidophorum repandum
• Lepisorus contortus
• Myristica malabarica
• Odontites vernus
• Penstemon linarioides
• Plagiomnium cuspidatum
• Plantago asiatica
• Plantago lanceolata
• Plantago major
• Plectranthus lanuginosus
• Populus yunnanensis
• Primulina tabacum
• Prunus grayana
• Prunus ssiori
• Rhodanthe maryonii
• Rhododendron campylocarpum
• Sagina japonica
• Sargentodoxa cuneata
• Scabiosa comosa
• Scapania aequiloba
• Solanum dulcamara
• Spartium junceum
• Toddalia asiatica
• Vachellia lasiopetala

Cross-Links

• PubChem: 5273567
• NPASS: NPC287597
• ChEMBL: CHEMBL518414
• LOTUS: LTS0180020
• wikiData: Q27136842