Harpagoside

Details

• Internal ID: 84963779-74c3-4cc1-8ad8-2eb7911be132
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate
• SMILES (Canonical): CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)OC(=O)C=CC4=CC=CC=C4
• SMILES (Isomeric): C[C@@]1(C[C@H]([C@]2([C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)OC(=O)/C=C/C4=CC=CC=C4
• InChI: InChI=1S/C24H30O11/c1-23(35-16(27)8-7-13-5-3-2-4-6-13)11-15(26)24(31)9-10-32-22(20(23)24)34-21-19(30)18(29)17(28)14(12-25)33-21/h2-10,14-15,17-22,25-26,28-31H,11-12H2,1H3/b8-7+/t14-,15-,17-,18+,19-,20-,21+,22+,23+,24-/m1/s1
• InChI Key: KVRQGMOSZKPBNS-FMHLWDFHSA-N
• Popularity: 309 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₁₁
• Molecular Weight: 494.50 g/mol
• Exact Mass: 494.17881177 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.20
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• 19210-12-9
• E-harpagoside
• UNII-8KGS1DC5ZU
• 8KGS1DC5ZU
• EINECS 242-881-6
• CHEBI:5625
• [(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate
• SMR001233395
• Harpaside
• (1S-(1alpha,4aalpha,5alpha,7alpha(E),7aalpha))-1,4a,5,6,7,7a-Hexahydro-4a,5-dihydroxy-7-methyl-7-((allyl-1-oxo-3-phenyl)oxy)cyclopenta(c)pyran-1-yl-beta-D-glucopyranoside
• [1S-[1alpha,4aalpha,5alpha,7alpha(E),7aalpha]]-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methyl-7-[(allyl-1-oxo-3-phenyl)oxy]cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside
• C24H30O11
• Prestwick3_000988
• HARPAGOSIDE [INCI]
• BSPBio_001055
• HARPAGOSIDE [WHO-DD]
• MLS002154086
• MLS002473324
• SCHEMBL893387
• BPBio1_001161
• CHEMBL516702
• MEGxp0_000469
• Harpagoside, analytical standard
• ACon0_000056
• ACon1_000134
• KVRQGMOSZKPBNS-FMHLWDFHSA-N
• DTXSID101032528
• HMS2098E17
• HMS2231N12
• HY-N0396
• MFCD00017415
• s9171
• AKOS015896715
• CCG-269650
• LMPR0102070010
• NCGC00179325-01
• NCGC00179325-02
• NCGC00179325-04
• AC-34268
• AS-56071
• AB00513986
• CS-0008931
• C09783
• H10494
• EN300-7357122
• A880338
• Q-100231
• BRD-K07996107-001-01-7
• BRD-K07996107-001-03-3
• Harpagoside, primary pharmaceutical reference standard
• Q25099323
• Harpagoside, European Pharmacopoeia (EP) Reference Standard
• (1S,4aS,5R,7S,7aS)-4a,5-Dihydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl cinnamate
• (1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl cinnamate
• (1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl (2E)-3-phenylprop-2-enoate
• .BETA.-D-GLUCOPYRANOSIDE, (1S,4AS,5R,7S,7AS)-1,4A,5,6,7,7A-HEXAHYDRO-4A,5-DIHYDROXY-7-METHYL-7-(((2E)-1-OXO-3-PHENYL-2-PROPENYL)OXY)CYCLOPENTA(C)PYRAN-1-YL
• beta-D-GLUCOPYRANOSIDE, (1S,4AS,5R,7S,7AS)-1,4A,5,6,7,7A-HEXAHYDRO-4A,5-DIHYDROXY-7-METHYL-7-(((2E)-1-OXO-3-PHENYL-2-PROPENYL)OXY)CYCLOPENTA(C)PYRAN-1-YL
• beta-D-Glucopyranoside, 1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methyl-7-((1-oxo-3-phenyl-2-propenyl)oxy)cyclopenta(c)pyran-1-yl, (1S-(1alpha,4aalpha,5alpha,7alpha(E),7aalpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6494	64.94%
Caco-2	-	0.8532	85.32%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6045	60.45%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.8588	85.88%
OATP1B3 inhibitior	+	0.9525	95.25%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6513	65.13%
P-glycoprotein inhibitior	-	0.6537	65.37%
P-glycoprotein substrate	-	0.7381	73.81%
CYP3A4 substrate	+	0.6551	65.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8809	88.09%
CYP3A4 inhibition	-	0.8888	88.88%
CYP2C9 inhibition	-	0.9436	94.36%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.6525	65.25%
CYP inhibitory promiscuity	-	0.8689	86.89%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5848	58.48%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9532	95.32%
Skin irritation	-	0.7650	76.50%
Skin corrosion	-	0.9496	94.96%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7139	71.39%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.8065	80.65%
skin sensitisation	-	0.8591	85.91%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7449	74.49%
Acute Oral Toxicity (c)	III	0.5445	54.45%
Estrogen receptor binding	+	0.7357	73.57%
Androgen receptor binding	+	0.6687	66.87%
Thyroid receptor binding	+	0.6197	61.97%
Glucocorticoid receptor binding	-	0.4708	47.08%
Aromatase binding	+	0.5968	59.68%
PPAR gamma	+	0.6694	66.94%
Honey bee toxicity	-	0.8379	83.79%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5355	53.55%
Fish aquatic toxicity	+	0.7676	76.76%

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	98.71%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.02%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.19%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.36%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.60%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.38%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.53%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.47%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.42%	97.09%
CHEMBL5028	O14672	ADAM10	84.13%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.13%	94.08%
CHEMBL2581	P07339	Cathepsin D	82.23%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	81.16%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.14%	95.83%

Plants that contains it

• Harpagophytum procumbens
• Harpagophytum zeyheri
• Melittis melissophyllum
• Phlogacanthus curviflorus
• Plantago lagopus
• Rogeria adenophylla
• Scrophularia buergeriana
• Scrophularia chrysantha
• Scrophularia koelzii
• Scrophularia ningpoensis
• Scrophularia nodosa
• Scrophularia scorodonia
• Scrophularia spicata
• Verbascum nigrum
• Verbascum pulverulentum
• Verbascum thapsus
• Verbascum undulatum

Cross-Links

• PubChem: 5281542
• NPASS: NPC276047
• ChEMBL: CHEMBL516702
• LOTUS: LTS0049528
• wikiData: Q25099323