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Harpagoside

Family: Plantae - Scrophulariaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Iridoid Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@]3([C@H]2[C@@](C)(OC(=O)/C=C/c2ccccc2)C[C@H]3O)O)[C@@H]([C@H]([C@@H]1O)O)O
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
InChIKey	KVRQGMOSZKPBNS-FMHLWDFHSA-N
Formula	C₂₄H₃₀O₁₁
HBA	11
HBD	6
MW	494.49
Rotatable Bonds	6
TPSA	175.37
LogP	-1.2
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.54
Exact Mass	494.18
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Verbascum dentifolium	Scrophulariaceae	Plantae	512637

Showing of synonyms

Arrif S, Lavaud C, et al. (2008). Iridoids from Verbascum dentifolium. Biochemical Systematics and Ecology,2008,36(8),669-673. [View]

Pubchem: 5281542

Cas: 19210-12-9

Gnps: CCMSLIB00004705050

Zinc: ZINC000008214398

Kegg Ligand: C09783

Chebi: 5625

Nmrshiftdb2: 60024524

Chembl: CHEMBL516702

CPRiL: 88370

SMILES: c1ccccc1C=CC(=O)OC2CCC(C23)C=COC3OC4CCCCO4

Level: 2

Mol. Weight: 494.49 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(C23)C=COC3

Level: 1

Mol. Weight: 494.49 g/mol

SMILES: C1CCC(C12)C(OC=C2)OC3CCCCO3

Level: 1

Mol. Weight: 494.49 g/mol

SMILES: C1CCC(C12)COC=C2

Level: 0

Mol. Weight: 494.49 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 494.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 494.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.89
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.900
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.33

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.780
Plasma Protein Binding: 66.17
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.010
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.830
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.080
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.750
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -313.680
Rat (Acute): 2.680
Rat (Chronic Oral): 3.800
Fathead Minnow: 4.110
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 521.660
Hydration Free Energy: -3.270
Log(D) at pH=7.4: 0.730
Log(P): -0.09
Log S: -1.63
Log(Vapor Pressure): -13.62
Melting Point: 131.12
pKa Acid: 3.84
pKa Basic: 3.56

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.8187
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.8187
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.8040
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.8040
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7667
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7667
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7654
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7654
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7624
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7624
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7514
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7514
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7255
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7255
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	2	0.7241
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	2	0.7241
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7159
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7159
23S rRNA (guanine(745)-N(1))-methyltransferase	P36999	RLMA_ECOLI	Escherichia coli	3	0.7152
23S rRNA (guanine(745)-N(1))-methyltransferase	P36999	RLMA_ECOLI	Escherichia coli	3	0.7152
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7024
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7024
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7024
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7024

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