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Record Information
Version1.0
Created at2022-09-05 21:45:13 UTC
Updated at2022-09-05 21:45:13 UTC
NP-MRD IDNP0220443
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,4r,5r,7s)-7-[(1s,2r,3as,3bs,5s,5ar,6s,9ar,9bs,11as)-5-chloro-1,2,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3ah,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-4,5-dimethyl-2-oxabicyclo[3.2.1]octan-3-one
DescriptionAnomanolide D belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. (1r,4r,5r,7s)-7-[(1s,2r,3as,3bs,5s,5ar,6s,9ar,9bs,11as)-5-chloro-1,2,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3ah,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-4,5-dimethyl-2-oxabicyclo[3.2.1]octan-3-one is found in Tubocapsicum anomalum. It was first documented in 2022 (PMID: 36075464). Based on a literature review a significant number of articles have been published on anomanolide D (PMID: 36075337) (PMID: 36075407) (PMID: 36075370) (PMID: 36075335).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC28H39ClO8
Average Mass539.0600 Da
Monoisotopic Mass538.23335 Da
IUPAC Name(1R,4R,5R,7S)-7-[(1S,2R,6S,7R,8S,10S,11S,13R,14S,15S)-8-chloro-6,7,13,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-14-yl]-4-hydroxy-4,5-dimethyl-2-oxabicyclo[3.2.1]octan-3-one
Traditional Name(1R,4R,5R,7S)-7-[(1S,2R,6S,7R,8S,10S,11S,13R,14S,15S)-8-chloro-6,7,13,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-14-yl]-4-hydroxy-4,5-dimethyl-2-oxabicyclo[3.2.1]octan-3-one
CAS Registry NumberNot Available
SMILES
C[C@@]12C[C@@H](OC(=O)[C@]1(C)O)[C@H](C2)[C@@]1(O)[C@H](O)C[C@H]2[C@@H]3C[C@H](Cl)[C@]4(O)[C@@H](O)C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C
InChI Identifier
InChI=1S/C28H39ClO8/c1-23-11-16(17(12-23)37-22(33)26(23,4)34)27(35)21(32)10-15-13-9-18(29)28(36)20(31)6-5-19(30)25(28,3)14(13)7-8-24(15,27)2/h5-6,13-18,20-21,31-32,34-36H,7-12H2,1-4H3/t13-,14+,15+,16+,17-,18+,20+,21-,23-,24+,25+,26+,27-,28+/m1/s1
InChI KeySHCLKNUPAXEEPB-ACABIRPMSA-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
Tubocapsicum anomalumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct ParentOxosteroids
Alternative Parents
Substituents
  • 24-hydroxysteroid
  • Prostaglandin skeleton
  • Steroid lactone
  • Eicosanoid
  • Androstane-skeleton
  • 17-hydroxysteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • Oxosteroid
  • 1-oxosteroid
  • Hydroxysteroid
  • 5-hydroxysteroid
  • 4-hydroxysteroid
  • Halo-steroid
  • 6-halo-steroid
  • Caprolactone
  • Cyclohexenone
  • Oxepane
  • Delta_valerolactone
  • Delta valerolactone
  • Fatty acyl
  • Oxane
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Ketone
  • Halohydrin
  • Chlorohydrin
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • 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
logP1.39ChemAxon
pKa (Strongest Acidic)11.95ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity133.71 m³·mol⁻¹ChemAxon
Polarizability56.08 ųChemAxon
Number of Rings6ChemAxon
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 IDC00038462
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102086555
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wang X, Yu L, Liu T, He Y, Wu S, Chen H, Yuan X, Wang J, Li X, Li H, Que Z, Qing Z, Zhou T: Methane and nitrous oxide concentrations and fluxes from heavily polluted urban streams: Comprehensive influence of pollution and restoration. Environ Pollut. 2022 Sep 5;313:120098. doi: 10.1016/j.envpol.2022.120098. [PubMed:36075337 ]
  2. Xu L, Wang W, Song W: A combination of metformin and insulin improve cardiovascular and cerebrovascular risk factors in individuals with type 1 diabetes mellitus. Diabetes Res Clin Pract. 2022 Sep;191:110073. doi: 10.1016/j.diabres.2022.110073. Epub 2022 Sep 6. [PubMed:36075464 ]
  3. Zhang G, Chen X, Li F, Que W, Qian J, Fang J, Ding T: Effects of environmental factors on selenite volatilization by freshwater microalgae. Sci Total Environ. 2022 Sep 6;854:158539. doi: 10.1016/j.scitotenv.2022.158539. [PubMed:36075407 ]
  4. Chen C, Wang Y, Hu MQ, Li H, Chen X, Qiang G, Sun Y, Zhu Y, Li B: Discovery of pyrrolo[2,3-d]pyrimidine-based molecules as a Wee1 inhibitor template. Bioorg Med Chem Lett. 2022 Nov 1;75:128973. doi: 10.1016/j.bmcl.2022.128973. Epub 2022 Sep 6. [PubMed:36075370 ]
  5. Iyagbaye L, Reichelt-Brushett A, Benkendorff K: Ni accumulation and effects on a representative Cnidaria - Exaiptasia pallida during single element exposure and in combination with Mn. Environ Pollut. 2022 Nov 15;313:120110. doi: 10.1016/j.envpol.2022.120110. Epub 2022 Sep 5. [PubMed:36075335 ]
  6. LOTUS database [Link]