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Catalposide
- Family: Plantae - Scrophulariaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Iridoid Glucoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@]2(CO)O[C@H]2[C@H]3OC(=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C22H26O12/c23-7-12-14(26)15(27)16(28)21(31-12)33-20-13-11(5-6-30-20)17(18-22(13,8-24)34-18)32-19(29)9-1-3-10(25)4-2-9/h1-6,11-18,20-21,23-28H,7-8H2/t11-,12-,13-,14-,15+,16-,17+,18+,20+,21+,22-/m1/s1 |
| InChIKey | UXSACQOOWZMGSE-RWORTQBESA-N |
| Formula | C22H26O12 |
| HBA | 12 |
| HBD | 6 |
| MW | 482.44 |
| Rotatable Bonds | 6 |
| TPSA | 187.9 |
| LogP | -2.02 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.59 |
| Exact Mass | 482.14 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Veronica anagalIis-aquatica | Scrophulariaceae | Plantae | 1421714 |
Showing of synonyms
Catalposide
6736-85-2
Hydroxybenzoyl catalpol
EINECS 229-789-1
UNII-7KD7K3964H
7KD7K3964H
CATALPOSIDE [MI]
(HYDROXYBENZOYL)CATALPOL
CATALPOL 6-P-HYDROXYBENZOATE
Beta-D-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-((4-hydroxybenzoyl)oxy)-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl, (1aS-(1a-alpha,1b-beta,2-beta,5a-beta,6-beta,6a-alpha))-
.BETA.-D-GLUCOPYRANOSIDE, (1AS,1BS,2S,5AR,6S,6AS)-1A,1B,2,5A,6,6A-HEXAHYDRO-6-((4-HYDROXYBENZOYL)OXY)-1A-(HYDROXYMETHYL)OXIRENO(4,5)CYCLOPENTA(1,2-C)PYRAN-2-YL
[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 4-hydroxybenzoate
((1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2,5a,6,6a-tetrahydro-1bH-oxireno(5,6)cyclopenta(1,3-c)pyran-6-yl) 4-hydroxybenzoate
((1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-3,9-dioxatricyclo(4.4.0.02,4)dec-7-en-5-yl) 4-hydroxybenzoate
(1S,2S,4S,5S,6S,10S)-2-(Hydroxymethyl)-10-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)-3,9-dioxatricyclo(4.4.0.0,)dec-7-en-5-yl 4-hydroxybenzoic acid
(1S,2S,4S,5S,6S,10S)-2-(Hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0,]dec-7-en-5-yl 4-hydroxybenzoic acid
[(1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] 4-hydroxybenzoate
((1aS,1bS,5aR,6S,6aS)-1a-(hydroxymethyl)-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-2,5a,6,6a-tetrahydro-1bH-oxireno(5,6)cyclopenta(1,3-c)pyran-6-yl) 4-hydroxybenzoate
[(1aS,1bS,5aR,6S,6aS)-1a-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] 4-hydroxybenzoate
229-789-1
BETA-D-GLUCOPYRANOSIDE, (1AS,1BS,2S,5AR,6S,6AS)-1A,1B,2,5A,6,6A-HEXAHYDRO-6-((4-HYDROXYBENZOYL)OXY)-1A-(HYDROXYMETHYL)OXIRENO(4,5)CYCLOPENTA(1,2-C)PYRAN-2-YL
CHEMBL2332354
SCHEMBL419598
DTXSID30986621
HY-N3552
BDBM50429458
AKOS032962388
MC06905
NCGC00347848-02
1a(S)alpha,1bbeta,2beta,5abeta,6beta,6aalpha-Hexahydro-6-((4-hydroxybenzoyl)oxy)-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl beta-D-glucopyranoside
MS-28964
CS-0023820
NS00046512
E88694
Catalpin
(1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-hexahydro-6-[(4-hydroxybenzoyl)oxy]-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c] pyran-2-yl-b-D-glucopyranoside
- Lahloub M, Zaghloul M, et al. (1993). Iridoid glycosides from veronica anagallis-aquatica. Phytochemistry, 1993, 33(2), 401-405. [View]
Pubchem:
93039
Cas:
6736-85-2
Gnps:
CCMSLIB00004704195
Zinc:
ZINC000008234299
Nmrshiftdb2:
60075196
Chembl:
CHEMBL2332354
Bindingdb:
50429458
CPRiL:
114316
SMILES: c1ccccc1C(=O)OC(C(O2)C23)C4C3C(OC=C4)OC5CCCCO5
Level: 2
Mol. Weight: 482.44 g/mol
SMILES: c1ccccc1C(=O)OC(C(O2)C23)C4C3COC=C4
Level: 1
Mol. Weight: 482.44 g/mol
SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4
Level: 1
Mol. Weight: 482.44 g/mol
SMILES: C12C(O2)CC3C1COC=C3
Level: 0
Mol. Weight: 482.44 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 482.44 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 482.44 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.59
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.010
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.35
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.750
- Plasma Protein Binding
- 39.21
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.530
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.490
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.540
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.560
- 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
- -425.740
- Rat (Acute)
- 2.780
- Rat (Chronic Oral)
- 3.630
- Fathead Minnow
- 4.060
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 534.970
- Hydration Free Energy
- -3.090
- Log(D) at pH=7.4
- -1.000
- Log(P)
- -0.9
- Log S
- -2.12
- Log(Vapor Pressure)
- -12.52
- Melting Point
- 157.2
- pKa Acid
- 4.77
- pKa Basic
- 2.9
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9188 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8773 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8638 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8618 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.8382 |
| Phenolphthiocerol/phthiocerol polyketide synthase subunit C | P96202 | PPSC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8104 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7949 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7916 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7848 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7832 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 3 | 0.7830 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7823 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7781 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7696 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7690 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7684 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7565 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 4 | 0.7542 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7487 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7477 |
| Acetyl-CoA carboxylase 2 | O00763 | ACACB_HUMAN | Homo sapiens | 4 | 0.7457 |
| Acyl-CoA:acyl-CoA alkyltransferase | Q8PDX2 | OLEA_XANCP | Xanthomonas campestris pv. campestris | 3 | 0.7400 |
| Oxygenase | Q194P4 | Q194P4_STRAA | Streptomyces argillaceus | 3 | 0.7365 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7333 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7329 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7324 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7282 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7235 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7227 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7225 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7203 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 2 | 0.7157 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7136 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7123 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7108 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7078 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7076 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 2 | 0.7051 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7042 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 2 | 0.7038 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7022 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7013 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 2 | 0.7004 |