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6-O-trans-cinnamoylantirrinoside
- Family: Plantae - Plantaginaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Iridoid Glycoside
| Canonical Smiles | OCC1O[C@@H](OC2OC=C[C@@]3(C2[C@@]2(C)OC2[C@H]3OC(=O)/C=C/c2ccccc2)O)[C@H](C([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C24H28O11/c1-23-18-22(34-21-17(29)16(28)15(27)13(11-25)32-21)31-10-9-24(18,30)20(19(23)35-23)33-14(26)8-7-12-5-3-2-4-6-12/h2-10,13,15-22,25,27-30H,11H2,1H3/b8-7+/t13?,15-,16?,17+,18?,19?,20-,21+,22?,23-,24+/m1/s1 |
| InChIKey | NUTXJCIINLOOGO-HAOSOWOFSA-N |
| Formula | C24H28O11 |
| HBA | 11 |
| HBD | 5 |
| MW | 492.48 |
| Rotatable Bonds | 6 |
| TPSA | 167.67 |
| LogP | -1.18 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.54 |
| Exact Mass | 492.16 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Anarrhinum pedatum | Plantaginaceae | Plantae | 2500742 |
Showing of synonyms
6-O-trans-cinnamoylantirrinoside
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)OC(C(O2)C23)C4C3C(OC=C4)OC5CCCCO5
Level: 2
Mol. Weight: 492.48 g/mol
SMILES: c1ccccc1C=CC(=O)OC(C(O2)C23)C4C3COC=C4
Level: 1
Mol. Weight: 492.48 g/mol
SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4
Level: 1
Mol. Weight: 492.48 g/mol
SMILES: C12C(O2)CC3C1COC=C3
Level: 0
Mol. Weight: 492.48 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 492.48 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 492.48 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.54
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.7
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.74
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.82
- Plasma Protein Binding
- 35.51
- 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
- 7.93
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.73
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.76
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.02
- 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
- -577.46
- Rat (Acute)
- 2.86
- Rat (Chronic Oral)
- 3.67
- Fathead Minnow
- 3.95
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 485.95
- Hydration Free Energy
- -3.12
- Log(D) at pH=7.4
- -0.33
- Log(P)
- 0.07
- Log S
- -2.28
- Log(Vapor Pressure)
- -11.85
- Melting Point
- 129.73
- pKa Acid
- 4.68
- pKa Basic
- 0.54
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8938 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7814 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7779 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7742 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7729 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7621 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7490 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7400 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7284 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7204 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 2 | 0.7128 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7102 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7035 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 2 | 0.7032 |