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Record Information
Version2.0
Created at2022-04-28 10:59:10 UTC
Updated at2022-04-28 10:59:10 UTC
NP-MRD IDNP0066740
Secondary Accession NumbersNone
Natural Product Identification
Common NameAugustine
DescriptionAugustine belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other. Augustine is found in Crinum amabile , Crinum angustum Rox., Crinum asiaticum, Crossyne flava, Mitragyna diversifolia and Mitragyna javanica Koord.et Val.var.microphylla Craib. Augustine was first documented in 2021 (PMID: 34862884). Based on a literature review a small amount of articles have been published on augustine (PMID: 35221865) (PMID: 35185021) (PMID: 34990607).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H19NO4
Average Mass301.3420 Da
Monoisotopic Mass301.13141 Da
IUPAC Name(1S,13R,15R,16S,18R)-15-methoxy-5,7,17-trioxa-12-azahexacyclo[10.6.2.0^{1,13}.0^{2,10}.0^{4,8}.0^{16,18}]icosa-2,4(8),9-triene
Traditional Name(1S,13R,15R,16S,18R)-15-methoxy-5,7,17-trioxa-12-azahexacyclo[10.6.2.0^{1,13}.0^{2,10}.0^{4,8}.0^{16,18}]icosa-2,4(8),9-triene
CAS Registry NumberNot Available
SMILES
CO[C@@H]1C[C@H]2N3CC[C@]2([C@H]2O[C@@H]12)C1=CC2=C(OCO2)C=C1C3
InChI Identifier
InChI=1S/C17H19NO4/c1-19-13-6-14-17(16-15(13)22-16)2-3-18(14)7-9-4-11-12(5-10(9)17)21-8-20-11/h4-5,13-16H,2-3,6-8H2,1H3/t13-,14-,15+,16+,17+/m1/s1
InChI KeyQLRRUWXMMVXORS-NRKLIOEPSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Crinum amabilePlant
Crinum angustum Rox.Plant
Crinum asiaticumLOTUS Database
Crossyne flavaLOTUS Database
Mitragyna diversifoliaLOTUS Database
Mitragyna javanica Koord.et Val.var.microphylla CraibPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAmaryllidaceae alkaloids
Sub ClassCrinine- and Haemanthamine-type amaryllidaceae alkaloids
Direct ParentCrinine- and Haemanthamine-type amaryllidaceae alkaloids
Alternative Parents
Substituents
  • Hemanthamine/crinine alkaloid skeleton
  • Benzoquinoline
  • Phenanthridine
  • Benzazepine
  • Tetrahydroisoquinoline
  • Quinoline
  • Benzodioxole
  • Indole or derivatives
  • Azepine
  • Oxepane
  • Aralkylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Acetal
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.21ALOGPS
logP1.12ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity77.99 m³·mol⁻¹ChemAxon
Polarizability31.83 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00024368
Chemspider ID138653
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAugustine of Hippo
METLIN IDNot Available
PubChem Compound157561
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Daniels G: Augustine Blood Group System and Equilibrative Nucleoside Transporter 1. Transfus Med Hemother. 2021 Dec 7;49(1):25-29. doi: 10.1159/000520596. eCollection 2022 Feb. [PubMed:35221865 ]
  2. Iozzia D: A Beginner's Success: The Impact of Plotinus's First Treatise among Christians. J Hist Ideas. 2022;83(1):1-16. doi: 10.1353/jhi.2022.0000. [PubMed:35185021 ]
  3. Martinez B, Da Silva BF, Aristizabal-Henao JJ, Denslow ND, Osborne TZ, Morrison ES, Bianchi TS, Bowden JA: Increased levels of perfluorooctanesulfonic acid (PFOS) during Hurricane Dorian on the east coast of Florida. Environ Res. 2022 May 15;208:112635. doi: 10.1016/j.envres.2021.112635. Epub 2022 Jan 4. [PubMed:34990607 ]
  4. Agius M, Agius M: Traumatic Events, Sexual Abuse and Mental Illness. Psychiatr Danub. 2021 Dec;33(Suppl 11):19-26. [PubMed:34862884 ]