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Record Information
Version1.0
Created at2022-09-05 21:13:02 UTC
Updated at2022-09-05 21:13:02 UTC
NP-MRD IDNP0220023
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,4r,5s,10r,12r,13s,16r,17r)-13-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one
DescriptionOvalifoliolide A belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. (1r,4r,5s,10r,12r,13s,16r,17r)-13-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one is found in Betula fruticosa. It was first documented in 2022 (PMID: 36051722). Based on a literature review a significant number of articles have been published on Ovalifoliolide A (PMID: 36050584) (PMID: 36044365) (PMID: 36043368) (PMID: 36038174) (PMID: 36030880) (PMID: 36029144).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H48O3
Average Mass456.7110 Da
Monoisotopic Mass456.36035 Da
IUPAC Name(1R,4R,5S,10R,12R,13S,16R,17R)-13-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0^{5,17}.0^{12,16}]heptadecan-8-one
Traditional Name(1R,4R,5S,10R,12R,13S,16R,17R)-13-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0^{5,17}.0^{12,16}]heptadecan-8-one
CAS Registry NumberNot Available
SMILES
CC(C)=CCC[C@](C)(O)[C@H]1CC[C@]2(C)[C@@H]1C[C@H]1OC(=O)CC[C@@]3(C)[C@H](CC[C@]2(C)[C@H]13)C(C)=C
InChI Identifier
InChI=1S/C30H48O3/c1-19(2)10-9-14-30(8,32)22-12-16-28(6)23(22)18-24-26-27(5,15-13-25(31)33-24)21(20(3)4)11-17-29(26,28)7/h10,21-24,26,32H,3,9,11-18H2,1-2,4-8H3/t21-,22+,23-,24-,26-,27+,28-,29-,30+/m1/s1
InChI KeyUJKRXDRUBVRCPX-PPNWLSRHSA-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
Betula fruticosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentSesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • Caprolactone
  • Oxepane
  • Tertiary alcohol
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP6.37ChemAxon
pKa (Strongest Basic)-0.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity135.6 m³·mol⁻¹ChemAxon
Polarizability54.79 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00058641
Chemspider ID8893980
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10718641
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wako M, Kono H, Koyama K, Fujimaki T, Furuya N, Haro H: The Anatomical Position of Graf's Standard Plane and Its Relationship With Pelvic Morphology: A Computed Tomography-Based Study. Cureus. 2022 Jul 28;14(7):e27424. doi: 10.7759/cureus.27424. eCollection 2022 Jul. [PubMed:36051722 ]
  2. Jayroe M, Aguilar DR, Porter A, Cima M, Chai S, Hayman K: Transmission Analysis of COVID-19 Outbreaks Associated with Places of Worship, Arkansas, May 2020-December 2020. J Relig Health. 2022 Sep 1. pii: 10.1007/s10943-022-01653-y. doi: 10.1007/s10943-022-01653-y. [PubMed:36050584 ]
  3. Belik AA, Khalyavin DD, Matsushita Y, Yamaura K: Triple A-Site Cation Ordering in the Ferrimagnetic Y2CuGaMn4O12 Perovskite. Inorg Chem. 2022 Sep 12;61(36):14428-14435. doi: 10.1021/acs.inorgchem.2c02343. Epub 2022 Aug 31. [PubMed:36044365 ]
  4. Siwach P, Sikarwar P, Rajput SA, Antharjanam S, Chandiran AK: The effect of halogenated spacer cations on structural symmetry-breaking in 2D halide double perovskites. Chem Commun (Camb). 2022 Aug 31. doi: 10.1039/d2cc02747j. [PubMed:36043368 ]
  5. Abukhadijah HJ, Turk-Adawi KI, Dewart N, Grace SL: Qualitative study measuring the usability of the International Cardiac Rehabilitation Registry. BMJ Open. 2022 Aug 29;12(8):e064255. doi: 10.1136/bmjopen-2022-064255. [PubMed:36038174 ]
  6. Bojko J, Walters E, Burgess A, Behringer DC: Rediscovering "Baculovirus-A" (Johnson, 1976): The complete genome of 'Callinectes sapidus nudivirus'. J Invertebr Pathol. 2022 Aug 27;194:107822. doi: 10.1016/j.jip.2022.107822. [PubMed:36030880 ]
  7. Menekse Beser D, Oluklu D, Uyan Hendem D, Yildirim M, Tugrul Ersak D, Goncu Ayhan S, Sahin D: Fetal echocardiographic evaluation before and after nifedipine treatment in preterm labor. Echocardiography. 2022 Sep;39(9):1245-1251. doi: 10.1111/echo.15444. Epub 2022 Aug 27. [PubMed:36029144 ]
  8. Parajuli D, Murali N, K C D, Karki B, Samatha K, Kim AA, Park M, Pant B: Advancements in MXene-Polymer Nanocomposites in Energy Storage and Biomedical Applications. Polymers (Basel). 2022 Aug 22;14(16):3433. doi: 10.3390/polym14163433. [PubMed:36015690 ]
  9. Ritchie LA, Penson PE, Akpan A, Lip GYH, Lane DA: Integrated Care for Atrial Fibrillation Management: The Role of the Pharmacist. Am J Med. 2022 Dec;135(12):1410-1426. doi: 10.1016/j.amjmed.2022.07.014. Epub 2022 Aug 21. [PubMed:36002045 ]
  10. Luan Z, Fu Y, Tan Y, Wang Y, Shan B, Li J, Zhou X, Chen W, Liu L, Fu B, Zhang DH, Yang X, Wang X: Observation of Competitive Nonadiabatic Photodissociation Dynamics of H(2)S(+) Cations. J Phys Chem Lett. 2022 Sep 1;13(34):8157-8162. doi: 10.1021/acs.jpclett.2c01892. Epub 2022 Aug 24. [PubMed:36001649 ]
  11. LOTUS database [Link]