Np mrd loader

Record Information
Version2.0
Created at2022-06-29 21:56:44 UTC
Updated at2022-06-29 21:56:45 UTC
NP-MRD IDNP0140884
Secondary Accession NumbersNone
Natural Product Identification
Common NameHautriwaic acid
DescriptionHautriwaic acid, also known as hautriwaate, belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. Hautriwaic acid is found in Baccharis calvescens, Baccharis chilco, Baccharis sarothroides, Croton setiger, Dodonaea viscosa and Nidorella ivifolia. Hautriwaic acid was first documented in 2012 (PMID: 22491678). Based on a literature review a small amount of articles have been published on Hautriwaic acid (PMID: 32927597) (PMID: 30525440) (PMID: 26166136) (PMID: 24075215).
Structure
Thumb
Synonyms
ValueSource
HautriwaateGenerator
Chemical FormulaC20H28O4
Average Mass332.4400 Da
Monoisotopic Mass332.19876 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC[C@]2(CO)[C@H](CCC=C2C(O)=O)[C@@]1(C)CCC1=COC=C1
InChI Identifier
InChI=1S/C20H28O4/c1-14-6-10-20(13-21)16(18(22)23)4-3-5-17(20)19(14,2)9-7-15-8-11-24-12-15/h4,8,11-12,14,17,21H,3,5-7,9-10,13H2,1-2H3,(H,22,23)/t14-,17-,19+,20-/m1/s1
InChI KeyPHKSUFCCGLWIMC-SIKIZQCASA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Baccharis calvescensLOTUS Database
Baccharis chilcoLOTUS Database
Baccharis sarothroidesLOTUS Database
Croton setigerLOTUS Database
Dodonaea viscosaLOTUS Database
Nidorella ivifoliaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentColensane and clerodane diterpenoids
Alternative Parents
Substituents
  • Clerodane diterpenoid
  • Furan
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Primary alcohol
  • Organic oxide
  • Alcohol
  • 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID33823774
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12310372
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kaigongi MM, Lukhoba CW, Ochieng' PJ, Taylor M, Yenesew A, Makunga NP: LC-MS-Based Metabolomics for the Chemosystematics of Kenyan Dodonaea viscosa Jacq (Sapindaceae) Populations. Molecules. 2020 Sep 10;25(18):4130. doi: 10.3390/molecules25184130. [PubMed:32927597 ]
  2. Cai S, Bellampalli SS, Yu J, Li W, Ji Y, Wijeratne EMK, Dorame A, Luo S, Shan Z, Khanna M, Moutal A, Streicher JM, Gunatilaka AAL, Khanna R: (-)-Hardwickiic Acid and Hautriwaic Acid Induce Antinociception via Blockade of Tetrodotoxin-Sensitive Voltage-Dependent Sodium Channels. ACS Chem Neurosci. 2019 Mar 20;10(3):1716-1728. doi: 10.1021/acschemneuro.8b00617. Epub 2018 Dec 20. [PubMed:30525440 ]
  3. Salinas-Sanchez DO, Zamilpa A, Perez S, Herrera-Ruiz M, Tortoriello J, Gonzalez-Cortazar M, Jimenez-Ferrer E: Effect of Hautriwaic Acid Isolated from Dodonaea viscosa in a Model of Kaolin/Carrageenan-Induced Monoarthritis. Planta Med. 2015 Sep;81(14):1240-7. doi: 10.1055/s-0035-1546197. Epub 2015 Jul 10. [PubMed:26166136 ]
  4. Ali H, Kabir N, Muhammad A, Shah MR, Musharraf SG, Iqbal N, Nadeem S: Hautriwaic acid as one of the hepatoprotective constituent of Dodonaea viscosa. Phytomedicine. 2014 Jan 15;21(2):131-40. doi: 10.1016/j.phymed.2013.08.019. Epub 2013 Sep 24. [PubMed:24075215 ]
  5. Salinas-Sanchez DO, Herrera-Ruiz M, Perez S, Jimenez-Ferrer E, Zamilpa A: Anti-inflammatory activity of hautriwaic acid isolated from Dodonaea viscosa leaves. Molecules. 2012 Apr 10;17(4):4292-9. doi: 10.3390/molecules17044292. [PubMed:22491678 ]