Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2021-06-19 23:28:05 UTC
Updated at2021-06-30 00:02:07 UTC
NP-MRD IDNP0032747
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-dehydrovomifoliol
Provided ByJEOL DatabaseJEOL Logo
Description(+)-Dehydrovomifoliol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (+)-dehydrovomifoliol is considered to be an isoprenoid. (+)-dehydrovomifoliol is found in Cucumis sativus. It was first documented in 2019 (PMID: 31542954). Based on a literature review a significant number of articles have been published on (+)-Dehydrovomifoliol (PMID: 33668728) (PMID: 33383824) (PMID: 32627491) (PMID: 31359654).
Structure
Thumb
Synonyms
ValueSource
(4S)-4-Hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-enyl]cyclohex-2-en-1-oneChEBI
(6R)-6-Hydroxy-3-oxo-alpha-iononeChEBI
(6S)-6-Hydroxy-3-oxo-alpha-iononeChEBI
DehydrovomifoliolChEBI
(6R)-6-Hydroxy-3-oxo-a-iononeGenerator
(6R)-6-Hydroxy-3-oxo-α-iononeGenerator
(6S)-6-Hydroxy-3-oxo-a-iononeGenerator
(6S)-6-Hydroxy-3-oxo-α-iononeGenerator
Chemical FormulaC13H18O3
Average Mass222.2840 Da
Monoisotopic Mass222.12559 Da
IUPAC Name(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one
Traditional Namedehydrovomifoliol
CAS Registry NumberNot Available
SMILES
[H]O[C@]1(\C([H])=C(/[H])C(=O)C([H])([H])[H])C(=C([H])C(=O)C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+/t13-/m1/s1
InChI KeyJJRYPZMXNLLZFH-URWSZGRFSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Cucumis sativus L.
    • Kai, H., et al, Chem. Pharm. Bull. 55, 133 (2007)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homomonocyclic 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
logP1.41ALOGPS
logP1.65ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)13.37ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.93 m³·mol⁻¹ChemAxon
Polarizability24.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006379
KNApSAcK IDC00029298
Chemspider ID599941
KEGG Compound IDC02533
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID4372
Good Scents IDNot Available
References
General References
  1. Yuzikhin OS, Gogoleva NE, Shaposhnikov AI, Konnova TA, Osipova EV, Syrova DS, Ermakova EA, Shevchenko VP, Nagaev IY, Shevchenko KV, Myasoedov NF, Safronova VI, Shavarda AL, Nizhnikov AA, Belimov AA, Gogolev YV: Rhizosphere Bacterium Rhodococcus sp. P1Y Metabolizes Abscisic Acid to Form Dehydrovomifoliol. Biomolecules. 2021 Feb 25;11(3). pii: biom11030345. doi: 10.3390/biom11030345. [PubMed:33668728 ]
  2. Malarz J, Michalska K, Stojakowska A: Stem Lettuce and Its Metabolites: Does the Variety Make Any Difference? Foods. 2020 Dec 29;10(1). pii: foods10010059. doi: 10.3390/foods10010059. [PubMed:33383824 ]
  3. Feng ZY, Ma YX, Wang H, Chen M: [Studies on chemical constituents of stems of Herpetospermum pedunculosum]. Zhongguo Zhong Yao Za Zhi. 2020 Jun;45(11):2571-2577. doi: 10.19540/j.cnki.cjcmm.20200227.201. [PubMed:32627491 ]
  4. Bendjedou H, Barboni L, Maggi F, Bennaceur M, Benamar H: Alkaloids and sesquiterpenes from roots and leaves of Lycium europaeum L. (Solanaceae) with antioxidant and anti-acetylcholinesterase activities. Nat Prod Res. 2019 Sep 23:1-5. doi: 10.1080/14786419.2019.1666386. [PubMed:31542954 ]
  5. Sun DX, Guo XF, A LT, Ma XL, Wei HY, Ma GX, Shi LL, Zhang J: [Chemical constituents from green walnut husks and their antitumor activity in vitro]. Zhongguo Zhong Yao Za Zhi. 2019 Jun;44(11):2278-2282. doi: 10.19540/j.cnki.cjcmm.20190321.201. [PubMed:31359654 ]
  6. Kai, H., et al. (2007). Kai, H., et al, Chem. Pharm. Bull. 55, 133 (2007). Chem. Pharm. Bull..