| Common Name |
Glaucamine
| Description |
Glaucamine is an alkaloid from Papaver rhoeas (corn poppy) Glaucamine belongs to the family of Benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.).
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29363 (Glaucamine)
| Synonyms |
| Value |
Source |
2,3-Dimethoxy-16-methyl-10,11-[methylenebis(oxy)]rheadan-8-ol, 9ciHMDB
Alkaloid R-LHMDB
| Chemical Formlia |
C21H23NO6
| Average Molecliar Weight |
385.4104
| Monoisotopic Molecliar Weight |
385.152537473
| IUPAC Name |
16,17-dimethoxy-22-methyl-6,8,12-trioxa-22-azapentacyclo[11.9.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]docosa-2(10),3,5(9),14,16,18-hexaen-11-ol
| Traditional Name |
16,17-dimethoxy-22-methyl-6,8,12-trioxa-22-azapentacyclo[11.9.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]docosa-2(10),3,5(9),14,16,18-hexaen-11-ol
| CAS Registry Number |
2255-44-9
| SMILES |
COC1=C(OC)C=C2C3OC(O)C4=C(C=CC5=C4OCO5)C3N(C)CCC2=C1
| InChI Identifier |
InChI=1S/C21H23NO6/c1-22-7-6-11-8-15(24-2)16(25-3)9-13(11)19-18(22)12-4-5-14-20(27-10-26-14)17(12)21(23)28-19/h4-5,8-9,18-19,21,23H,6-7,10H2,1-3H3
| InChI Key |
XYWRZQQANNOTTD-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of organic compounds known as rhoeadine alkaloids. These are alkaloids with a structure based on rhoeadine. They usually contain a benzazepine system fused with a six-membered hemiacetal or acetal.
| Kingdom |
Organic compounds
| Super Class |
Alkaloids and derivatives
| Class |
Rhoeadine alkaloids
| Sub Class |
Not Available
| Direct Parent |
Rhoeadine alkaloids
| Alternative Parents |
Benzazepines
2-benzopyrans
Benzodioxoles
Anisoles
Azepines
Aralkylamines
Alkyl aryl ethers
Trialkylamines
Hemiacetals
Oxacyclic compounds
Azacyclic compounds
Acetals
Hydrocarbon derivatives
| Substituents |
Rhoeadine-skeleton
Benzazepine
2-benzopyran
Isochromane
Benzopyran
Benzodioxole
Anisole
Aralkylamine
Azepine
Alkyl aryl ether
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Hemiacetal
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Acetal
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Not Available
| Application |
Nutrient
| Cellliar locations |
Cytoplasm
Extracellliar
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point222 – 223 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.61 mg/mLALOGPS
logP1.87ALOGPS
logP2.45ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)11.26ChemAxon
pKa (Strongest Basic)5.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.62 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity101.18 m3·mol-1ChemAxon
Polarizability40.8 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000428
| KNApSAcK ID |
C00025451
| Chemspider ID |
530119
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29363
| Metagene Link |
HMDB29363
| METLIN ID |
Not Available
| PubChem Compound |
609842
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: 23-Hydroxybetulinic acid
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 21185318
