Select a section from the left sidebar
Rotundifoleine
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Chromone Alkaloid
| Canonical Smiles | CN1CCC2C(C1O)C(=O)c1c(O2)cc2c(c1O)c(=O)cc(o2)C |
|---|---|
| InChI | InChI=1S/C17H17NO6/c1-7-5-8(19)12-10(23-7)6-11-13(15(12)20)16(21)14-9(24-11)3-4-18(2)17(14)22/h5-6,9,14,17,20,22H,3-4H2,1-2H3 |
| InChIKey | VAAJKLYKCBUSIZ-UHFFFAOYSA-N |
| Formula | C17H17NO6 |
| HBA | 7 |
| HBD | 2 |
| MW | 331.32 |
| Rotatable Bonds | 0 |
| TPSA | 100.21 |
| LogP | 1.02 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.41 |
| Exact Mass | 331.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Mitragyna inermis | Rubiaceae | Plantae | 170023 |
| 2 | Schumanniophyton magnificum | Rubiaceae | Plantae | 114490 |
Showing of synonyms
Rotundifoleine
88720-92-7
N-Methylschumannificine
DTXSID701008321
4H,9H-Pyrano(2',3':5,6)(1)benzopyrano(3,4-c0pyridine-4,9-dione, 8,8a,10,11,12,12a-hexahydro-5,8-dihydroxy-2,10-dimethyl-
5,7-Dihydroxy-2,8-dimethyl-6a,7,8,9,10,10a-hexahydro-4H,6H-pyrano[3',2':6,7][1]benzopyrano[3,2-c]pyridine-4,6-dione
- Okogun JI, Adeboye JO, et al. (1983). Novel structures of two chromone alkaloids from root-bark of Schumanniophyton magnificum. Planta Medica, 1983, 49(10), 95-98. [View]
- Toklo PM, Alowanou GG, et al. (2023). UPLC-QToF-ESI-MS identification and anthelmintic activity of Mitragyna inermis (Willd.) Kuntze (Rubiaceae). Heliyon 9 (2023) e16448. [View]
Pubchem:
184891
Cas:
88720-92-7
No compound-protein relationship available.
SMILES: O=c1ccoc(c12)cc3c(c2)C(=O)C4C(O3)CCNC4
Level: 0
Mol. Weight: 331.32 g/mol
Anthelmintic
Antioxidant
Larval toxicity
Absorption
- Caco-2 (logPapp)
- -5.23
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.94
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.31
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.78
- Plasma Protein Binding
- 26.03
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- 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
- 9.89
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.37
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.44
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 9.04
- 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
- 0.12
- Rat (Acute)
- 2.86
- Rat (Chronic Oral)
- 2.03
- Fathead Minnow
- 4.2
- 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
- 433.42
- Hydration Free Energy
- -11.99
- Log(D) at pH=7.4
- 0.9
- Log(P)
- 1.24
- Log S
- -3.25
- Log(Vapor Pressure)
- -9.2
- Melting Point
- 229.89
- pKa Acid
- 6.59
- pKa Basic
- 5.82
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Caspase-7 | P55210 | CASP7_HUMAN | Homo sapiens | 3 | 0.8756 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8720 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8554 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8529 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8488 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8095 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.7957 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7840 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7815 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.7758 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7722 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7692 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7526 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7362 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7348 |
| Fumarate reductase subunit D | P0A8Q3 | FRDD_ECOLI | Escherichia coli | 3 | 0.7323 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7259 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7194 |
| Peripheral plasma membrane protein CASK | O14936 | CSKP_HUMAN | Homo sapiens | 3 | 0.7153 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7078 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7050 |