Isoacteoside

Details

• Internal ID: 1110d0d0-42e1-4f9d-9237-6b79caebb3dd
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2O)OCCC3=CC(=C(C=C3)O)O)COC(=O)C=CC4=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]2O)OCCC3=CC(=C(C=C3)O)O)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C29H36O15/c1-13-22(35)24(37)25(38)29(42-13)44-27-23(36)20(12-41-21(34)7-4-14-2-5-16(30)18(32)10-14)43-28(26(27)39)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1
• InChI Key: FNMHEHXNBNCPCI-QEOJJFGVSA-N
• Popularity: 71 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

• 61303-13-7
• isoverbascoside
• Isoacetoside
• UNII-588LJK42AP
• 588LJK42AP
• NSC-729649
• [(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• NSC 729649
• beta-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-alpha-L-mannopyranosyl)-, 6-(3-(3,4-dihydroxyphenyl)-2-propenoate), (E)-
• iso-acteoside
• Acteoside isomer
• Verbascoside,(S)
• [(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CHEMBL504873
• CHEBI:192072
• DTXSID501317837
• HY-N0022
• BDBM50386896
• MFCD06798947
• NSC729649
• s9128
• AKOS037514697
• CCG-270268
• MS-30813
• Q-100709
• Q27261572
• ((2R,3R,4S,5R,6R)-6-(3,4-Dihydroxyphenethoxy)-3,5-dihydroxy-4-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)methyl (E)-3-(3,4-dihydroxyphenyl)acrylate
• (E)-((2R,3R,4S,5R,6R)-6-(3,4-dihydroxyphenethoxy)-3,5-dihydroxy-4-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yl)methyl 3-(3,4-dihydroxyphenyl)acrylate
• .BETA.-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL 3-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, 6-((2E)-3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE)
• .beta.-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-.alpha.-L-mannopyranosyl)-6-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]-
• 1-O-[2-(3,4-Dihydroxyphenyl)ethyl]-3-O-(3alpha,4alpha,5beta-trihydroxy-6alpha-methyltetrahydro-2H-pyran-2beta-yl)-6-O-[3-(3,4-dihydroxyphenyl)acryloyl]-beta-D-glucopyranose
• 2-(3',4'-dihydroxyphenyl)ethyl 6-O-caffeoyl-3-O-(alpha-l-rhamnopyranosyl)-beta-d-glucopyranoside
• beta-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL 3-O-(6-DEOXY-alpha-L-MANNOPYRANOSYL)-, 6-((2E)-3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7283	72.83%
Caco-2	-	0.9065	90.65%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.8183	81.83%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8883	88.83%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8910	89.10%
P-glycoprotein inhibitior	-	0.5836	58.36%
P-glycoprotein substrate	-	0.6454	64.54%
CYP3A4 substrate	+	0.6459	64.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.9284	92.84%
CYP2C9 inhibition	-	0.7093	70.93%
CYP2C19 inhibition	-	0.8036	80.36%
CYP2D6 inhibition	-	0.8975	89.75%
CYP1A2 inhibition	-	0.8055	80.55%
CYP2C8 inhibition	+	0.7034	70.34%
CYP inhibitory promiscuity	-	0.6658	66.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6280	62.80%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9199	91.99%
Skin irritation	-	0.8390	83.90%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3786	37.86%
Micronuclear	-	0.6367	63.67%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8344	83.44%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.9553	95.53%
Acute Oral Toxicity (c)	III	0.7807	78.07%
Estrogen receptor binding	+	0.7769	77.69%
Androgen receptor binding	-	0.5676	56.76%
Thyroid receptor binding	+	0.5453	54.53%
Glucocorticoid receptor binding	+	0.5540	55.40%
Aromatase binding	+	0.5496	54.96%
PPAR gamma	+	0.7190	71.90%
Honey bee toxicity	-	0.7144	71.44%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8812	88.12%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4393	P39900	Matrix metalloproteinase 12	8220 nM	IC50	PMID: 22658537
CHEMBL280	P45452	Matrix metalloproteinase 13	11090 nM	IC50	PMID: 22658537
CHEMBL321	P14780	Matrix metalloproteinase 9	14280 nM	IC50	PMID: 22658537
CHEMBL333	P08253	Matrix metalloproteinase-2	8960 nM	IC50	PMID: 22658537

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.67%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.57%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.57%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.71%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.63%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	93.34%	94.73%
CHEMBL3194	P02766	Transthyretin	93.24%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.01%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.16%	99.17%
CHEMBL2581	P07339	Cathepsin D	89.82%	98.95%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	88.82%	80.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.18%	86.92%
CHEMBL4208	P20618	Proteasome component C5	83.87%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.82%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.30%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.65%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	80.59%	95.93%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.49%	96.37%

Plants that contains it

• Abies alba
• Acanthus ebracteatus
• Acanthus montanus
• Acorus calamus
• Allium stipitatum
• Alstonia longifolia
• Amphilophium crucigerum
• Angiopteris evecta
• Artemisia argentea
• Asphodeline damascena
• Barleria strigosa
• Bauhinia tarapotensis
• Brandisia hancei
• Brodiaea californica
• Buddleja davidii
• Callicarpa macrophylla
• Carex distachya
• Caryopteris incana
• Cistanche deserticola
• Cistanche phelypaea
• Cistanche salsa
• Cyathula tomentosa
• Dolichandrone serrulata
• Echinostephia aculeata
• Eucalyptus kitsoniana
• Euphorbia antiquorum
• Exochorda racemosa subsp. giraldii
• Fernandoa adenophylla
• Fraxinus ornus
• Globularia alypum
• Globularia davisiana
• Globularia trichosantha
• Harpagophytum procumbens
• Hemionitis lemmonii
• Himantoglossum hircinum
• Jacaranda caucana
• Kopsia arborea
• Lamium purpureum
• Lepidophorum repandum
• Lippia alba
• Markhamia lutea
• Markhamia stipulata
• Maytenus laevis
• Myristica malabarica
• Odontites vernus
• Olea europaea
• Orobanche coerulescens
• Paulownia tomentosa
• Pedicularis artselaeri
• Pedicularis striata
• Phlomis brunneogaleata
• Phlomoides rotata
• Phlomoides umbrosa
• Pinellia ternata
• Plagiomnium cuspidatum
• Plantago alpina
• Plantago asiatica
• Plantago australis
• Plantago depressa
• Plectranthus lanuginosus
• Pogostemon cablin
• Populus yunnanensis
• Prostanthera melissifolia
• Psorothamnus polydenius
• Rehmannia glutinosa
• Rhodanthe maryonii
• Rhododendron campylocarpum
• Ruellia patula
• Sagina japonica
• Santisukia kerrii
• Scabiosa comosa
• Scapania aequiloba
• Sesamum indicum
• Sideritis trojana
• Solanum dulcamara
• Spartium junceum
• Stachys byzantina
• Stachys officinalis
• Stereospermum cylindricum
• Toddalia asiatica
• Tynanthus panurensis
• Vachellia lasiopetala
• Verbena officinalis
• Veronica persica
• Vigna umbellata
• Volkameria inermis

Cross-Links

• PubChem: 6476333
• NPASS: NPC64141
• ChEMBL: CHEMBL504873
• LOTUS: LTS0012202
• wikiData: Q27261572