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Sanguinine
- Family: Plantae - Amaryllidaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | O[C@H]1C=C[C@@]23C(C1)Oc1c3c(ccc1O)CN(CC2)C |
|---|---|
| InChI | InChI=1S/C16H19NO3/c1-17-7-6-16-5-4-11(18)8-13(16)20-15-12(19)3-2-10(9-17)14(15)16/h2-5,11,13,18-19H,6-9H2,1H3/t11-,13?,16-/m0/s1 |
| InChIKey | OYSGWKOGUVOGFQ-NXLBOVRGSA-N |
| Formula | C16H19NO3 |
| HBA | 4 |
| HBD | 2 |
| MW | 273.33 |
| Rotatable Bonds | 0 |
| TPSA | 52.93 |
| LogP | 1.55 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 273.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Lycoris sanguinea | Amaryllidaceae | Plantae | 108053 |
Showing of synonyms
Sanguinine
O-Desmethylgalantamine
O-Desmethyl Galantamine
UNII-L7ZOW3CZ7W
(1S,12S,14R)-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraene-9,14-diol
GALANTAMINE METABOLITE M6
GALANTHAMINE, O-DEMETHYL-
DTXSID40209575
6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPINE-3,6-DIOL, 4A,5,9,10,11,12-HEXAHYDRO-11-METHYL-, (4AS,6R,8AS)-
GALANTAMINE HYDROBROMIDE IMPURITY, O-DESMETHYLGALANTAMINE-(USP IMPURITY)
GALANTAMINE HYDROBROMIDE IMPURITY, O-DESMETHYLGALANTAMINE-[USP IMPURITY]
(1S,12S,14R)-4-methyl-11-oxa-4-azatetracyclo(8.6.1.01,12.06,17)heptadeca-6(17),7,9,15-tetraene-9,14-diol
DTXCID90132066
1,2,4-trimethoxy-12-methyl-(1,3)benzodioxolo(5,6-c)phenanthridin-12-ium
1,2,4-trimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
O-Desmethyl Galanthamine
60755-80-8
O-DESMETHYLGALANTHAMINE
L7ZOW3CZ7W
CHEMBL1524
CHEBI:32117
O-Demethylgalanthamine
6-O-demethylgalantamine
SCHEMBL10440905
ARD193991
BDBM50221070
AKOS030242530
(4aS,6R,8aS)-11-Methyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepine-3,6-diol
(4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepine-3,6-diol
10-Methyl-galantham-1-ene-3beta,6-diol
MS-23882
DB-257731
HY-131413
CS-0134267
NS00116193
O-DESMETHYLGALANTAMINE [USP IMPURITY]
F82739
Q27114789
(1S,12S,14R)-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0?,??.0?,??]heptadeca-6(17),7,9,15-tetraene-9,14-diol
10-Methyl-galantham-1-ene-3b,6-diol
- Abdallah OM. (1995). Minor alkaloids from Lycoris sanguinea. Phytochemistry,1995,39(2),477-478. [View]
Pubchem:
443722
Cas:
60755-80-8
Zinc:
ZINC000004102420
Kegg Ligand:
C12232
Chebi:
32117
Nmrshiftdb2:
60063576
Chembl:
CHEMBL1524
Comptox:
DTXSID40209575
Bindingdb:
50221070
CPRiL:
433412
SMILES: C1=CCCC2Oc(c3C124)cccc3CNCC4
Level: 0
Mol. Weight: 273.33 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.04
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.62
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.13
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.29
- Plasma Protein Binding
- 27.27
- 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
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 14.56
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.21
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.64
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.69
- 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
- 0.98
- Rat (Acute)
- 2.71
- Rat (Chronic Oral)
- 2.08
- Fathead Minnow
- 3.95
- 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
- 348.48
- Hydration Free Energy
- -9.95
- Log(D) at pH=7.4
- 0.63
- Log(P)
- 0.91
- Log S
- -2.02
- Log(Vapor Pressure)
- -6.78
- Melting Point
- 174.58
- pKa Acid
- 7.5
- pKa Basic
- 7.9
| 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 | 0.9688 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.9688 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8753 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8753 |
| N-glycosylase/DNA lyase | O15527 | OGG1_HUMAN | Homo sapiens | 4 | 0.8456 |
| N-glycosylase/DNA lyase | O15527 | OGG1_HUMAN | Homo sapiens | 4 | 0.8456 |
| Acetylcholine-binding protein | P58154 | ACHP_LYMST | Lymnaea stagnalis | 3 | 0.8330 |
| Acetylcholine-binding protein | P58154 | ACHP_LYMST | Lymnaea stagnalis | 3 | 0.8330 |
| 3',5'-cyclic-AMP phosphodiesterase 4A | P27815 | PDE4A_HUMAN | Homo sapiens | 4 | 0.8281 |
| 3',5'-cyclic-AMP phosphodiesterase 4A | P27815 | PDE4A_HUMAN | Homo sapiens | 4 | 0.8281 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8166 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8166 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8127 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8127 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8117 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8117 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8080 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8080 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.8028 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.8028 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.7973 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.7973 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7965 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7965 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.7909 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.7909 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7905 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7905 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7897 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7897 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7852 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7852 |
| HLA class I histocompatibility antigen, B alpha chain | P01889 | HLAB_HUMAN | Homo sapiens | 3 | 0.7788 |
| HLA class I histocompatibility antigen, B alpha chain | P01889 | HLAB_HUMAN | Homo sapiens | 3 | 0.7788 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7771 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7771 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7750 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7750 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7687 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7687 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7667 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7667 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7646 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7646 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7631 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7631 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 3 | 0.7614 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 3 | 0.7614 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7585 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7585 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7504 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7504 |
| Leucine--tRNA ligase | P07813 | SYL_ECOLI | Escherichia coli | 3 | 0.7486 |
| Leucine--tRNA ligase | P07813 | SYL_ECOLI | Escherichia coli | 3 | 0.7486 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7422 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7422 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 3 | 0.7397 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 3 | 0.7397 |
| Mitomycin biosynthesis 6-O-methyltransferase | Q9X5T6 | MMCR_STRLA | Streptomyces lavendulae | 3 | 0.7393 |
| Mitomycin biosynthesis 6-O-methyltransferase | Q9X5T6 | MMCR_STRLA | Streptomyces lavendulae | 3 | 0.7393 |
| Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | Q9Y3Z3 | SAMH1_HUMAN | Homo sapiens | 3 | 0.7379 |
| Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | Q9Y3Z3 | SAMH1_HUMAN | Homo sapiens | 3 | 0.7379 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7282 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7282 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7272 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7272 |
| Adenosine receptor A2a | P29274 | AA2AR_HUMAN | Homo sapiens | 4 | 0.7247 |
| Adenosine receptor A2a | P29274 | AA2AR_HUMAN | Homo sapiens | 4 | 0.7247 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7220 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7220 |
| Calmodulin-1 | P0DP29 | CALM1_RAT | Rattus norvegicus | 3 | 0.7209 |
| Calmodulin-1 | P0DP29 | CALM1_RAT | Rattus norvegicus | 3 | 0.7209 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7191 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7191 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7183 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7183 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7174 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7174 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7159 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7159 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7144 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7144 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7116 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7116 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7112 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7112 |
| Sepiapterin reductase | Q64105 | SPRE_MOUSE | Mus musculus | 3 | 0.7099 |
| Sepiapterin reductase | Q64105 | SPRE_MOUSE | Mus musculus | 3 | 0.7099 |
| S-norcoclaurine synthase | Q67A25 | NCS_THLFG | Thalictrum flavum subsp. glaucum | 3 | 0.7087 |
| S-norcoclaurine synthase | Q67A25 | NCS_THLFG | Thalictrum flavum subsp. glaucum | 3 | 0.7087 |
| Tryptophan--tRNA ligase, cytoplasmic | Q12109 | SYWC_YEAST | Saccharomyces cerevisiae | 3 | 0.7080 |
| Eukaryotic translation initiation factor 4E type 3 | Q9DBB5 | IF4E3_MOUSE | Mus musculus | 3 | 0.7080 |
| Tryptophan--tRNA ligase, cytoplasmic | Q12109 | SYWC_YEAST | Saccharomyces cerevisiae | 3 | 0.7080 |
| Eukaryotic translation initiation factor 4E type 3 | Q9DBB5 | IF4E3_MOUSE | Mus musculus | 3 | 0.7080 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7062 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7062 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 4 | 0.7060 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 4 | 0.7060 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7052 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7052 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7040 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7040 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7023 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7023 |