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Tri-O-methylnorbergenin
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: C-Glycoside And Phenylpropanoid
- Subclass: Phenylpropanoid
| Canonical Smiles | OCC1OC2C(C(C1O)O)OC(=O)c1c2c(OC)c(c(c1)OC)OC |
|---|---|
| InChI | InChI=1S/C16H20O9/c1-21-7-4-6-9(13(23-3)12(7)22-2)14-15(25-16(6)20)11(19)10(18)8(5-17)24-14/h4,8,10-11,14-15,17-19H,5H2,1-3H3 |
| InChIKey | RGHGUQJYNLPWPT-UHFFFAOYSA-N |
| Formula | C16H20O9 |
| HBA | 9 |
| HBD | 3 |
| MW | 356.33 |
| Rotatable Bonds | 4 |
| TPSA | 123.91 |
| LogP | -0.59 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.56 |
| Exact Mass | 356.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Anthonotha macrophylla | Leguminosae/Fabaceae | Plantae | 162653 |
| 2 | Newtonia griffoniana | Leguminosae/Fabaceae | Plantae | 148736 |
Showing of synonyms
Tri-O-methylnorbergenin
33815-57-5
(2R,3S,4S,4aR,10bS)-3,4,4a,10b-Tetrahydro-3,4-dihydroxy-2-(hydroxymethyl)-8,9,10-trimethoxypyrano[3,2-c][2]benzopyran-6(2H)-one
Dimethylbergenin
(2r,3s,4s,4ar,10bs)-3,4-dihydroxy-2-(hydroxymethyl)-8,9,10-trimet Hoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2h)-one
- Kinyok MJ, Bonnet S, et al. (2017). A new flavanolignan and a new alkane from the Stem bark of Newtonia griffoniana.. Natural product research,2017, 31(19), 2233-2238. [View] [PubMed]
- Kinyok MJ, Wilhelm A, et al. (2021). Chemical constituents of the leaves of Anthonotha macrophylla (Leguminosae).. Natural product research,2021, 35(21), 3865-3872. [View] [PubMed]
Pubchem:
13420511
Cas:
33815-57-5
CPRiL:
424423
SMILES: c1cccc(c12)C3C(OC2=O)CCCO3
Level: 0
Mol. Weight: 356.33 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.21
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.72
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.06
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.77
- Plasma Protein Binding
- -5.13
- 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
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.16
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.04
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.06
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.3
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 0.76
- Rat (Acute)
- 2.16
- Rat (Chronic Oral)
- 3.13
- Fathead Minnow
- 4.01
- 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
- 408.35
- Hydration Free Energy
- -11.98
- Log(D) at pH=7.4
- 0.22
- Log(P)
- -0.23
- Log S
- -1.69
- Log(Vapor Pressure)
- -7.71
- Melting Point
- 171.94
- pKa Acid
- 7.95
- pKa Basic
- 1.3
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.9292 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8603 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8308 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7997 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7671 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7422 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7322 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7273 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7241 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7174 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7170 |