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Record Information
Version2.0
Created at2022-04-28 17:11:03 UTC
Updated at2022-04-28 17:11:03 UTC
NP-MRD IDNP0071835
Secondary Accession NumbersNone
Natural Product Identification
Common NameSecoxyloganin
DescriptionSecoxyloganin belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Thus, secoxyloganin is considered to be an isoprenoid. Secoxyloganin is found in Acicarpha tribuloides, Adina racemosa, Calycophyllum spruceanum , Citronella gongonha, Gentiana rhodantha, Guettarda platypoda, Hydrangea macrophylla, Klaprothia mentzelioides, Lippia graveolens , Lippia origanoides, Loasa acerifolia, Lonicera japonica , Lonicera periclymenum, Morinda coreia, Phillyrea latifolia, Picconia excelsa, Rauwolfia serpentina, Sinoadina racemosa, Strychnos lucida and Strychnos spinosa . Secoxyloganin was first documented in 2021 (PMID: 34574160). Based on a literature review a small amount of articles have been published on secoxyloganin (PMID: 35137662) (PMID: 34147039) (PMID: 33124697).
Structure
Thumb
Synonyms
ValueSource
Secoxy-loganinMeSH
Chemical FormulaC17H24O11
Average Mass404.3680 Da
Monoisotopic Mass404.13186 Da
IUPAC Name2-[(2S,3R,4S)-3-ethenyl-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetic acid
Traditional Name[(2S,3R,4S)-3-ethenyl-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetic acid
CAS Registry NumberNot Available
SMILES
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CC(O)=O
InChI Identifier
InChI=1S/C17H24O11/c1-3-7-8(4-11(19)20)9(15(24)25-2)6-26-16(7)28-17-14(23)13(22)12(21)10(5-18)27-17/h3,6-8,10,12-14,16-18,21-23H,1,4-5H2,2H3,(H,19,20)/t7-,8+,10-,12-,13+,14-,16+,17+/m1/s1
InChI KeyMQLSOVRLZHTATK-PEYNGXJCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTerpene glycosides
Alternative Parents
Substituents
  • Terpene glycoside
  • Glycosyl compound
  • Secoiridoid-skeleton
  • O-glycosyl compound
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Oxane
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP-1.4ALOGPS
logP-1.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area172.21 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity89.45 m³·mol⁻¹ChemAxon
Polarizability38.78 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00031346
Chemspider ID142980
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162868
PDB IDNot Available
ChEBI ID132712
Good Scents IDNot Available
References
General References
  1. Nakayama H, Nishi N, Matsuo Y, Tanaka T, Kotoda N, Ishimaru K: A new secoiridoid glucoside from Olea europaea. J Asian Nat Prod Res. 2022 Feb 9:1-8. doi: 10.1080/10286020.2021.2017898. [PubMed:35137662 ]
  2. Abbattista R, Losito I, Calvano CD, Cataldi TRI: Exploring the Isomeric Precursors of Olive Oil Major Secoiridoids: An Insight into Olive Leaves and Drupes by Liquid-Chromatography and Fourier-Transform Tandem Mass Spectrometry. Foods. 2021 Aug 31;10(9). pii: foods10092050. doi: 10.3390/foods10092050. [PubMed:34574160 ]
  3. Xu QD, Zhou ZQ, Yu J, He Q, Sun Q, Zeng WC: Effect of Cedrus deodara extract on the physiochemical and sensory properties of salted meat and its action mechanism. J Food Sci. 2021 Jul;86(7):2910-2923. doi: 10.1111/1750-3841.15801. Epub 2021 Jun 19. [PubMed:34147039 ]
  4. Rodriguez-Lopez CE, Hong B, Paetz C, Nakamura Y, Koudounas K, Passeri V, Baldoni L, Alagna F, Calderini O, O'Connor SE: Two bi-functional cytochrome P450 CYP72 enzymes from olive (Olea europaea) catalyze the oxidative C-C bond cleavage in the biosynthesis of secoxy-iridoids - flavor and quality determinants in olive oil. New Phytol. 2021 Feb;229(4):2288-2301. doi: 10.1111/nph.16975. Epub 2020 Oct 30. [PubMed:33124697 ]