Verbascoside

Details

• Internal ID: b5f47355-ecb5-4da0-98bf-5990406c7de0
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C29H36O15/c1-13-22(36)23(37)24(38)29(41-13)44-27-25(39)28(40-9-8-15-3-6-17(32)19(34)11-15)42-20(12-30)26(27)43-21(35)7-4-14-2-5-16(31)18(33)10-14/h2-7,10-11,13,20,22-34,36-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29-/m0/s1
• InChI Key: FBSKJMQYURKNSU-ZLSOWSIRSA-N
• Popularity: 1,816 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.60 g/mol
• Exact Mass: 624.20542044 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.02
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

• Acteoside
• 61276-17-3
• Kusaginin
• TJC 160
• TJC-160
• 3TGX09BD5B
• DTXSID701021953
• CHEBI:132853
• NSC-603831
• [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• beta-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-alpha-L-mannopyranosyl)-, 4-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate]
• ((2R,3R,4R,5R,6R)-6-(2-(3,4-dihydroxyphenyl)ethoxy)-5-hydroxy-2-(hydroxymethyl)-4-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-tetrahydropyran-3-yl) (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• ((2R,3R,4R,5R,6R)-6-(2-(3,4-dihydroxyphenyl)ethoxy)-5-hydroxy-2-(hydroxymethyl)-4-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl) (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• beta-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-alpha-L-mannopyranosyl)-, 4-((2E)-3-(3,4-dihydroxyphenyl)-2-propenoate)
• RefChem:51015
• DTXCID101506860
• 6-(2-(3,4-dihydroxyphenyl)ethoxy)-5-hydroxy-2-(hydroxymethyl)-4-((3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 612-110-1
• Verbacoside
• acetoside
• MFCD00221751
• NSC 603831
• C29H36O15
• (2R,3R,4R,5R,6R)-6-(3,4-Dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)-4-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl (E)-3-(3,4-dihydroxyphenyl)acrylate
• UNII-3TGX09BD5B
• Reh-acteoside
• .BETA.-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL 3-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, 4-((2E)-3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE)
• .beta.-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-.alpha.-L-mannopyranosyl)-, 4-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate]
• RUSSETINOL
• STEREOSPERMIN
• Acteoside; Verbascoside
• Verbascoside (Standard)
• Acetoside (Verbascoside)
• Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-alpha-L-mannopyranosyl)-, 4-(3-(3,4-dihydroxyphenyl)-2-propenoate), (E)-beta-D-
• MLS002473233
• SCHEMBL657970
• VERBASCOSIDE [USP-RS]
• CHEMBL231853
• CHEMBL444478
• orb1304265
• SCHEMBL29485048
• SCHEMBL29499087
• SCHEMBL29626822
• cid_5281800
• GTPL12550
• HY-N0021R
• Verbascoside, >=99% (HPLC)
• cid_24978601
• GLXC-07496
• HMS2205K11
• HY-N0021
• BDBM50241867
• MSK000876
• s5458
• AKOS015897165
• CCG-270269
• DB12996
• OV08034
• NCGC00378687-03
• (2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• AS-75167
• SMR001397320
• NS00070422
• 276A173
• B864379
• Q411426
• BRD-K36201510-001-06-7
• Verbascoside, primary pharmaceutical reference standard
• Verbascoside, United States Pharmacopeia (USP) Reference Standard
• ((2R,3R,4R,5R,6R)-6-(3,4-dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)-4-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-3-yl) 3-(3,4-dihydroxyphenyl)acrylate
• ((2R,3R,4R,5R,6R)-6-(3,4-dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)-4-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-3-yl)3-(3,4-dihydroxyphenyl)acrylate
• (3,4-Dihydroxyphenyl)ethyl O-.alpha.-rhamnopyranosyl(1->3)-4-O-caffeoyl-.beta.-D glucopyranoside
• (E)-(2R,3R,4R,5R,6R)-6-(3,4-Dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)-4-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl 3-(3,4-dihydroxyphenyl)acrylate
• .beta.-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl3-O-(6-deoxy-.alpha.-L-mannopyranosyl)-, 4-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate]
• |A-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-|A-L-mannopyranosyl)-, 4-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate]
• 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-alpha-L-mannopyranosyl)-4-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside
• 2-(3,4-dihydroxyphenyl)ethyl 3-O-(alpha-L-rhamnopyranosyl)-4-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7586	75.86%
Caco-2	-	0.9049	90.49%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7962	79.62%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.8832	88.32%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8204	82.04%
P-glycoprotein inhibitior	-	0.5537	55.37%
P-glycoprotein substrate	-	0.6291	62.91%
CYP3A4 substrate	+	0.6492	64.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.8907	89.07%
CYP2C9 inhibition	-	0.7325	73.25%
CYP2C19 inhibition	-	0.8467	84.67%
CYP2D6 inhibition	-	0.8986	89.86%
CYP1A2 inhibition	-	0.8483	84.83%
CYP2C8 inhibition	+	0.6859	68.59%
CYP inhibitory promiscuity	-	0.5836	58.36%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6709	67.09%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9165	91.65%
Skin irritation	-	0.8374	83.74%
Skin corrosion	-	0.9574	95.74%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7157	71.57%
Micronuclear	-	0.6467	64.67%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8149	81.49%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.9493	94.93%
Acute Oral Toxicity (c)	III	0.8034	80.34%
Estrogen receptor binding	+	0.7890	78.90%
Androgen receptor binding	-	0.6862	68.62%
Thyroid receptor binding	+	0.5677	56.77%
Glucocorticoid receptor binding	+	0.5647	56.47%
Aromatase binding	-	0.4847	48.47%
PPAR gamma	+	0.6924	69.24%
Honey bee toxicity	-	0.6626	66.26%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.7773	77.73%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	15848.9 nM	Potency	via CMAUP
CHEMBL299	P17252	Protein kinase C alpha	9300 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	99.72%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.25%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	96.58%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.60%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.49%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	92.96%	94.73%
CHEMBL3194	P02766	Transthyretin	92.79%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.61%	99.17%
CHEMBL2581	P07339	Cathepsin D	92.28%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.89%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.85%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.02%	97.36%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.36%	80.78%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.61%	96.37%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.15%	91.71%

Plants that contains it

• Abeliophyllum distichum
• Abies alba
• Acacia kempeana
• Acanthus ebracteatus
• Acanthus ilicifolius
• Acanthus montanus
• Achillea millefolium
• Aeginetia indica
• Aegiphila obducta
• Aframomum sulcatum
• Ajuga incisa
• Alhagi pseudalhagi subsp. persarum
• Allium stipitatum
• Aloysia citrodora
• Alstonia longifolia
• Angiopteris evecta
• Antirrhinum majus
• Arctotheca calendula
• Artemisia argentea
• Asphodeline damascena
• Asystasia intrusa
• Avicennia germinans
• Avicennia marina
• Avicennia marina subsp. marina
• Baillonella toxisperma
• Ballota nigra
• Barleria lupulina
• Barleria prionitis
• Barleria strigosa
• Bartsia alpina
• Betonica officinalis
• Brandisia hancei
• Brodiaea californica
• Broussonetia papyrifera
• Buddleja davidii
• Buddleja globosa
• Buddleja officinalis
• Buddleja parviflora
• Buddleja salviifolia
• Buddleja scordioides
• Buddleja yunnanensis
• Byblis liniflora
• Calceolaria hypericina
• Calceolaria plectranthifolia
• Callicarpa dichotoma
• Callicarpa japonica
• Callicarpa macrophylla
• Callicarpa nudiflora
• Callitriche stagnalis
• Campsis grandiflora
• Campsis radicans
• Carex distachya
• Caryopteris incana
• Cassinopsis madagascariensis
• Cassytha filiformis
• Castanopsis cuspidata
• Castilleja attenuata
• Castilleja indivisa
• Castilleja integra
• Castilleja wightii
• Centaurea axillaris
• Chelone obliqua
• Cistanche deserticola
• Cistanche mongolica
• Cistanche phelypaea
• Cistanche salsa
• Clerodendrum brachyanthum
• Clerodendrum bungei
• Clerodendrum formicarum
• Clerodendrum infortunatum
• Clerodendrum trichotomum
• Coleus lanuginosus
• Cordylanthus kingii
• Crotalaria laburnifolia
• Cyathula tomentosa
• Danae racemosa
• Daphniphyllum calycinum
• Decaisnea fargesii
• Dendrobium crepidatum
• Dendrobium thyrsiflorum
• Deplanchea speciosa
• Digitalis purpurea
• Diospyros buxifolia
• Dolichandrone serrulata
• Duranta erecta
• Echinacea pallida
• Echinacea purpurea
• Echinostephia aculeata
• Elaeagnus angustifolia
• Eremophila clarkei
• Eremophila forrestii
• Eremophila gilesii
• Eucalyptus kitsoniana
• Euonymus japonicus
• Euphorbia antiquorum
• Exochorda racemosa subsp. giraldii
• Fernandoa adenophylla
• Fontanesia fortunei
• Forsythia europaea
• Forsythia japonica
• Forsythia koreana
• Forsythia suspensa
• Forsythia viridissima
• Fraxinus americana
• Fraxinus angustifolia subsp. oxycarpa
• Fraxinus excelsior
• Fraxinus griffithii
• Fraxinus malacophylla
• Fraxinus ornus
• Fraxinus uhdei
• Globularia alypum
• Globularia bisnagarica
• Globularia dumulosa
• Globularia orientalis
• Globularia trichosantha
• Gratiola officinalis
• Halleria lucida
• Harpagophytum procumbens
• Harpagophytum zeyheri
• Himantoglossum hircinum
• Hygrophila erecta
• Hymenaea courbaril
• Incarvillea diffusa
• Isodon sculponeatus
• Jacaranda caucana
• Jacaranda mimosifolia
• Jasminum elongatum
• Jasminum mesnyi
• Jasminum nudiflorum
• Jasminum polyanthum
• Kigelia africana
• Kopsia arborea
• Laburnum watereri
• Lagotis brevituba
• Lagotis stolonifera
• Lamium album
• Lamium purpureum
• Lancea tibetica
• Lantana camara
• Lantana fucata
• Lantana radula
• Lantana trifolia
• Leonotis nepetifolia
• Leonurus glaucescens
• Leonurus japonicus
• Lepidophorum repandum
• Lessertia frutescens
• Ligustrum expansum
• Ligustrum lucidum
• Ligustrum robustum
• Lippia alba
• Lippia multiflora
• Lupinus mutabilis
• Lycopus asper
• Magnolia officinalis
• Magnolia salicifolia
• Markhamia lutea
• Markhamia stipulata
• Marrubium alysson
• Marrubium velutinum
• Marrubium vulgare
• Melampodium argophyllum
• Millingtonia hortensis
• Mitraria coccinea
• Momordica charantia
• Monochasma savateri
• Montanoa guatemalensis
• Myristica malabarica
• Nepeta ucranica
• Newbouldia laevis
• Notholaena lemmonii
• Odontites vernus
• Olea europaea
• Orobanche coerulescens
• Orobanche crenata
• Orobanche hederae
• Orobanche ramosa
• Orobanche rapum-genistae
• Osmanthus fragrans
• Ozothamnus obcordatus
• Panzerina lanata
• Paulownia tomentosa
• Pedicularis artselaeri
• Pedicularis condensata
• Pedicularis densispica
• Pedicularis lasiophrys
• Pedicularis longiflora
• Pedicularis nordmanniana
• Pedicularis rex
• Pedicularis sibthorpii
• Pedicularis spicata
• Pedicularis striata
• Pedicularis torta
• Pedicularis verticillata
• Penstemon albidus
• Penstemon ambiguus
• Penstemon crandallii
• Penstemon gentianoides
• Penstemon hirsutus
• Penstemon linarioides
• Penstemon roseus
• Penstemon rydbergii
• Penstemon secundiflorus
• Penstemon serrulatus
• Phillyrea latifolia
• Phlomis armeniaca
• Phlomis aurea
• Phlomis brunneogaleata
• Phlomis grandiflora
• Phlomis herba-venti
• Phlomis samia
• Phlomoides hamosa
• Phlomoides rotata
• Phlomoides tuberosa
• Phlomoides umbrosa
• Phtheirospermum japonicum
• Picconia excelsa
• Pinellia ternata
• Pinguicula moranensis
• Plagiomnium cuspidatum
• Plantago asiatica
• Plantago crassifolia
• Plantago depressa
• Plantago hookeriana
• Plantago lagopus
• Plantago lanceolata
• Plantago major
• Plantago myosuros
• Plantago raoulii
• Plantago serraria
• Pogostemon cablin
• Polygonatum stenophyllum
• Populus yunnanensis
• Premna corymbosa
• Premna microphylla
• Premna odorata
• Prostanthera melissifolia
• Pteris biaurita subsp. fornicata
• Quercus robur
• Rauvolfia serpentina
• Recordia reitzii
• Rehmannia glutinosa
• Retzia capensis
• Rhodanthe maryonii
• Rhododendron campylocarpum
• Rogeria adenophylla
• Rosa rugosa
• Ruellia patula
• Sagina japonica
• Salsola arbuscula
• Santisukia kerrii
• Scabiosa comosa
• Scapania aequiloba
• Scrophularia buergeriana
• Scrophularia ningpoensis
• Scrophularia nodosa
• Scrophularia scopolii
• Scrophularia scorodonia
• Scutellaria albida
• Scutellaria baicalensis
• Scutellaria orientalis
• Scutellaria pekinensis var. pekinensis
• Scutellaria prostrata
• Scutellaria repens
• Senecio variabilis
• Sesamum alatum
• Sesamum angolense
• Sesamum indicum
• Sideritis brevibracteata
• Sideritis lyciae
• Sideritis ozturkii
• Sideritis perfoliata
• Sideritis trojana
• Solanum dulcamara
• Spartium junceum
• Stachys byzantina
• Stachys inflata subsp. caucasica
• Stachys lavandulifolia
• Stachys rigida
• Stachytarpheta cayennensis
• Strobilanthes cusia
• Syringa josikaea
• Syringa reticulata
• Syringa reticulata subsp. amurensis
• Syringa vulgaris
• Tecoma stans var. sambucifolia
• Tectona grandis
• Tetrachondra hamiltonii
• Tetradium ruticarpum
• Teucrium chamaedrys
• Teucrium lanigerum
• Teucrium polium
• Triaenophora rupestris
• Tynanthus panurensis
• Vachellia lasiopetala
• Verbascum macrurum
• Verbascum phlomoides
• Verbascum spinosum
• Verbascum thapsus
• Verbascum undulatum
• Verbascum wiedemannianum
• Verbena brasiliensis
• Verbena litoralis
• Verbena officinalis
• Veronica austriaca
• Veronica persica
• Vigna umbellata
• Viscum album
• Viscum coloratum
• Volkameria inermis
• Zanthoxylum asiaticum

Cross-Links

• PubChem: 5281800
• NPASS: NPC197316
• ChEMBL: CHEMBL444478
• LOTUS: LTS0168159
• wikiData: Q411426