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Girinimbine
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Carbazole Alkaloid
| Canonical Smiles | Cc1cc2c(c3c1OC(C)(C)C=C3)[nH]c1c2cccc1 |
|---|---|
| InChI | InChI=1S/C18H17NO/c1-11-10-14-12-6-4-5-7-15(12)19-16(14)13-8-9-18(2,3)20-17(11)13/h4-10,19H,1-3H3 |
| InChIKey | GAEQWKVGMHUUKO-UHFFFAOYSA-N |
| Formula | C18H17NO |
| HBA | 1 |
| HBD | 1 |
| MW | 263.34 |
| Rotatable Bonds | 0 |
| TPSA | 25.02 |
| LogP | 4.81 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.22 |
| Exact Mass | 263.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Clausena anisata | Rutaceae | Plantae | 159034 |
Showing of synonyms
Girinimbine
23095-44-5
Girinimbin
3,11-Dihydro-3,3,5-trimethyl-Pyrano(3,2-a)carbazole
Pyrano(3,2-a)carbazole, 3,11-dihydro-3,3,5-trimethyl-
3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazole, 9CI
5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1,3,7,9,11,13,15-heptaene
3,11-Dihydro-3,3,5-trimethylpyrano(3,2-a)carbazole, 9ci
Pyrano[3,2-a]carbazole, 3,11-dihydro-3,3,5-trimethyl-
5,5,8-trimethyl-6-oxa-17-azatetracyclo(8.7.0.0^(2,7).0^(11,16))heptadeca-1,3,7,9,11,13,15-heptaene
GRINIMIBINE
3,3,5-trimethyl-11H-pyrano[3,2-a]carbazole
NSC 94932
WH639V7QSF
MLS000863568
CHEBI:69926
NSC-94932
SMR000440762
C18H17NO
3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole
UNII-WH639V7QSF
Cid_96943
MEGxp0_000255
SCHEMBL4132680
CHEMBL1477760
ACon1_001999
BDBM68168
DTXSID90945774
GAEQWKVGMHUUKO-UHFFFAOYSA-N
HMS2270D17
HY-N9488
NSC94932
YAA09544
AKOS040763158
DA-73737
MS-23714
CS-0181880
G14332
AK-693/40962733
3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazole
BRD-K08091267-001-01-2
Q25104278
- Tatsimo SJN, Tamokou JDD, et al. (2015). LC-MS guided isolation of antibacterial and cytotoxic constituents from Clausena anisata. Med Chem Res, 2015, 24, 1468–1479. [View]
Pubchem:
96943
Cas:
23095-44-5
Zinc:
ZINC000001615142
Chebi:
69926
Nmrshiftdb2:
60021615
Metabolights:
MTBLC69926
Chembl:
CHEMBL1477760
Bindingdb:
68168
CPRiL:
66214
SMILES: c1cccc(c1c23)[nH]c2c4c(cc3)OCC=C4
Level: 0
Mol. Weight: 263.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.93
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.43
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.09
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.53
- Plasma Protein Binding
- 38.51
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.9
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 2.2
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.21
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.61
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- 4.68
- Rat (Acute)
- 2.48
- Rat (Chronic Oral)
- 1.8
- Fathead Minnow
- 4.89
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Toxic
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 423.72
- Hydration Free Energy
- -8.66
- Log(D) at pH=7.4
- 4.98
- Log(P)
- 5.45
- Log S
- -6.39
- Log(Vapor Pressure)
- -8.17
- Melting Point
- 203.86
- pKa Acid
- 12.67
- pKa Basic
- 6.91
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.9111 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8577 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8260 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8249 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8188 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8177 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8147 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7865 |
| Vitamin D3 receptor | P13053 | VDR_RAT | Rattus norvegicus | 3 | 0.7781 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7774 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 4 | 0.7744 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7713 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.7577 |
| Lanosterol synthase | P48449 | ERG7_HUMAN | Homo sapiens | 3 | 0.7549 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7475 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7465 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7374 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 3 | 0.7366 |
| Reductase homolog | Q9ZGC1 | Q9ZGC1_STRCY | Streptomyces cyanogenus | 3 | 0.7326 |
| Retinoic acid receptor beta | P10826 | RARB_HUMAN | Homo sapiens | 3 | 0.7269 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7257 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7256 |
| Prostaglandin G/H synthase 2 | Q05769 | PGH2_MOUSE | Mus musculus | 4 | 0.7221 |
| Scytalone dehydratase | P56221 | SCYD_MAGO7 | Pyricularia oryzae | 4 | 0.7161 |
| Terminal oxygenase component of carbazole | Q84II6 | Q84II6_JANS3 | Janthinobacterium sp | 3 | 0.7155 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7151 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7149 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7134 |
| Aldo-keto reductase family 1 member B1 | P80276 | ALDR_PIG | Sus scrofa | 3 | 0.7117 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7115 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7111 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7111 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7097 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7091 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 4 | 0.7088 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7048 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7029 |