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(±)-carnegine
- Family: Plantae - Chenopodiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid
| Canonical Smiles | COc1cc2c(cc1OC)CCN([C@H]2C)C |
|---|---|
| InChI | InChI=1S/C13H19NO2/c1-9-11-8-13(16-4)12(15-3)7-10(11)5-6-14(9)2/h7-9H,5-6H2,1-4H3/t9-/m0/s1 |
| InChIKey | HRSIPKSSEVRSPG-VIFPVBQESA-N |
| Formula | C13H19NO2 |
| HBA | 3 |
| HBD | 0 |
| MW | 221.3 |
| Rotatable Bonds | 2 |
| TPSA | 21.7 |
| LogP | 2.25 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 16 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.54 |
| Exact Mass | 221.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Arthrocnemum glaucum | Chenopodiaceae | Plantae | 239181 |
Showing of synonyms
(±)-carnegine
(-)-Carnegine
(-)-Pectenine
(+-)-Carnegine
Carnegine, (-)-
Pectenine, (-)-
(S)-(-)-Carnegine
38221-25-9
UNII-EZM3RAR846
EZM3RAR846
CHEBI:64
Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-1,2-dimethyl-, (1S)-
(1S)-6,7-dimethoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinoline
Carnegine (Pectenine, N-Methylsalsolidine)
C09375
AP-123/11407085
(S)-6,7-Dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline
CHEMBL454315
(+/-)-CARNEGINE
AC1L9CEE
CTK1B5040
CARNEGINE, (S)-
CHEMBL1186208
SCHEMBL19888927
BDBM50014633
BDBM50367917
AKOS030605450
Q27105219
6,7-Dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydro-isoquinoline
Hydrochloride ((S)-(+)-carnegine)
- Khalil AT, Halim AF, et al. (1992). (-)-1-methylcorypalline, an isoquinoline alkaloid from Arthrocnemum glaucum. Phytochemistry,1992,31(3),1023-1025. [View]
Pubchem:
442186
Cas:
38221-25-9
Zinc:
ZINC000001669445
Kegg Ligand:
C09375
Chebi:
64
Nmrshiftdb2:
60065424
Chembl:
CHEMBL1186208
Bindingdb:
50367917
No compound-protein relationship available.
SMILES: C1CNCc(c12)cccc2
Level: 0
Mol. Weight: 221.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.71
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.310
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.11
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.300
- Plasma Protein Binding
- 26.52
- 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
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.720
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.120
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.570
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 8.280
- Micronucleos
- Safe
- 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
- -0.300
- Rat (Acute)
- 3.260
- Rat (Chronic Oral)
- 1.320
- Fathead Minnow
- 3.790
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 285.030
- Hydration Free Energy
- -7.460
- Log(D) at pH=7.4
- 1.660
- Log(P)
- 1.75
- Log S
- -1.02
- Log(Vapor Pressure)
- -4.53
- Melting Point
- 86.2
- pKa Acid
- 11.45
- pKa Basic
- 8.9
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.9780 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.9780 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8822 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8822 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.8805 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.8805 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8432 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8432 |
| NADPH-dependent 7-cyano-7-deazaguanine reductase | Q9KTK0 | QUEF_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8217 |
| NADPH-dependent 7-cyano-7-deazaguanine reductase | Q9KTK0 | QUEF_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8217 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.8142 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.8142 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8029 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8029 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7993 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7993 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7981 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7981 |
| S-norcoclaurine synthase | Q67A25 | NCS_THLFG | Thalictrum flavum subsp. glaucum | 3 | 0.7912 |
| S-norcoclaurine synthase | Q67A25 | NCS_THLFG | Thalictrum flavum subsp. glaucum | 3 | 0.7912 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7829 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7829 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7792 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7792 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7723 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7723 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7569 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7569 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | P62617 | ISPF_ECOLI | Escherichia coli | 3 | 0.7565 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | P62617 | ISPF_ECOLI | Escherichia coli | 3 | 0.7565 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7549 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7549 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7530 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7530 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7525 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7525 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7477 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7477 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7445 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7445 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7425 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7425 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7401 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7401 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7394 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7394 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7337 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7337 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7328 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7328 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7299 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7299 |
| ADP compounds hydrolase NudE | P45799 | NUDE_ECOLI | Escherichia coli | 2 | 0.7295 |
| ADP compounds hydrolase NudE | P45799 | NUDE_ECOLI | Escherichia coli | 2 | 0.7295 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7269 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7269 |
| Toluene-4-monooxygenase system, hydroxylase component subunit alpha | Q00456 | TMOA_PSEME | Pseudomonas mendocina | 2 | 0.7268 |
| Toluene-4-monooxygenase system, hydroxylase component subunit alpha | Q00456 | TMOA_PSEME | Pseudomonas mendocina | 2 | 0.7268 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7265 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7265 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7251 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7251 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7243 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7243 |
| Beta-galactoside alpha-2,6-sialyltransferase 1 | P15907 | SIAT1_HUMAN | Homo sapiens | 3 | 0.7241 |
| Beta-galactoside alpha-2,6-sialyltransferase 1 | P15907 | SIAT1_HUMAN | Homo sapiens | 3 | 0.7241 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7240 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7240 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7235 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7235 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7223 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7223 |
| rRNA methylase | Q8DSS3 | Q8DSS3_STRMU | Streptococcus mutans serotype c | 2 | 0.7192 |
| rRNA methylase | Q8DSS3 | Q8DSS3_STRMU | Streptococcus mutans serotype c | 2 | 0.7192 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7191 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7191 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7183 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7183 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7160 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7160 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 3 | 0.7158 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 3 | 0.7158 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7152 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7152 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7136 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7136 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7134 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7134 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7110 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7110 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7106 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7106 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7100 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7100 |
| Proline iminopeptidase | O32449 | PIP_SERMA | Serratia marcescens | 2 | 0.7097 |
| Proline iminopeptidase | O32449 | PIP_SERMA | Serratia marcescens | 2 | 0.7097 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7096 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7096 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7072 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7072 |
| Nucleoside 2-deoxyribosyltransferase | Q8RLY5 | Q8RLY5_LACHE | Lactobacillus helveticus | 2 | 0.7069 |
| Nucleoside 2-deoxyribosyltransferase | Q8RLY5 | Q8RLY5_LACHE | Lactobacillus helveticus | 2 | 0.7069 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7062 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7062 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7061 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7061 |
| 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 | O50008 | METE1_ARATH | Arabidopsis thaliana | 2 | 0.7052 |
| 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 | O50008 | METE1_ARATH | Arabidopsis thaliana | 2 | 0.7052 |
| Kallikrein-4 | Q9Y5K2 | KLK4_HUMAN | Homo sapiens | 2 | 0.7051 |
| Kallikrein-4 | Q9Y5K2 | KLK4_HUMAN | Homo sapiens | 2 | 0.7051 |
| N-glycosylase/DNA lyase | O15527 | OGG1_HUMAN | Homo sapiens | 3 | 0.7047 |
| N-glycosylase/DNA lyase | O15527 | OGG1_HUMAN | Homo sapiens | 3 | 0.7047 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.7035 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.7035 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 2 | 0.7032 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 2 | 0.7032 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 2 | 0.7026 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 2 | 0.7026 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7025 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7025 |
| RNA polymerase sigma factor SigA | Q5SKW1 | Q5SKW1_THET8 | Thermus thermophilus | 2 | 0.7020 |
| RNA polymerase sigma factor SigA | Q5SKW1 | Q5SKW1_THET8 | Thermus thermophilus | 2 | 0.7020 |
| Kallikrein-4 | Q9Y5K2 | KLK4_HUMAN | Homo sapiens | 2 | 0.7019 |
| Kallikrein-4 | Q9Y5K2 | KLK4_HUMAN | Homo sapiens | 2 | 0.7019 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7016 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7016 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7007 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7007 |