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Record Information
Version2.0
Created at2021-01-06 02:30:49 UTC
Updated at2021-07-15 17:26:42 UTC
NP-MRD IDNP0017877
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcaulin B
Provided ByNPAtlasNPAtlas Logo
Description Acaulin B is found in Acaulium. Acaulin B was first documented in 2018 (PMID: 29624065).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC42H56O20
Average Mass880.8900 Da
Monoisotopic Mass880.33649 Da
IUPAC Name(2R,7S)-7-{[(2E,4R,5S)-4,5-dihydroxyhex-2-enoyl]oxy}-4-oxo-2-[(1S,2S,5S,6R,7Z,11S,15S,16S,19S,22Z,24R,25S)-6,16,24-trihydroxy-5,11,19,25-tetramethyl-3,9,14,21,27,28-hexaoxo-4,10,20,26-tetraoxatricyclo[14.11.1.0^{2,15}]octacosa-7,22-dien-1-yl]octanoic acid
Traditional Name(2R,7S)-7-{[(2E,4R,5S)-4,5-dihydroxyhex-2-enoyl]oxy}-4-oxo-2-[(1S,2S,5S,6R,7Z,11S,15S,16S,19S,22Z,24R,25S)-6,16,24-trihydroxy-5,11,19,25-tetramethyl-3,9,14,21,27,28-hexaoxo-4,10,20,26-tetraoxatricyclo[14.11.1.0^{2,15}]octacosa-7,22-dien-1-yl]octanoic acid
CAS Registry NumberNot Available
SMILES
C[C@@H](CCC(=O)C[C@@H](C(O)=O)[C@@]12[C@@H]3[C@H](C(=O)CC[C@H](C)OC(=O)\C=C/[C@@H](O)[C@H](C)OC3=O)[C@@](O)(CC[C@H](C)OC(=O)\C=C/[C@@H](O)[C@H](C)OC1=O)C2=O)OC(=O)\C=C\[C@@H](O)[C@H](C)O
InChI Identifier
InChI=1S/C42H56O20/c1-20(58-32(49)14-11-28(45)23(4)43)7-9-26(44)19-27(37(52)53)42-36-35(31(48)10-8-21(2)59-33(50)15-12-29(46)24(5)61-38(36)54)41(57,39(42)55)18-17-22(3)60-34(51)16-13-30(47)25(6)62-40(42)56/h11-16,20-25,27-30,35-36,43,45-47,57H,7-10,17-19H2,1-6H3,(H,52,53)/b14-11+,15-12-,16-13-/t20-,21-,22-,23-,24-,25-,27-,28+,29+,30+,35-,36+,41-,42-/m0/s1
InChI KeyLTVAKGJIXKXNFK-DKSQHPQSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
AcauliumNPAtlas
Chemical Taxonomy
ClassificationNot classified
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
logP0.94ALOGPS
logP1.44ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area321.16 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity211.7 m³·mol⁻¹ChemAxon
Polarizability87.71 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
External LinksNot Available
References
General References
  1. Wang TT, Wei YJ, Ge HM, Jiao RH, Tan RX: Acaulins A and B, Trimeric Macrodiolides from Acaulium sp. H-JQSF. Org Lett. 2018 Apr 20;20(8):2490-2493. doi: 10.1021/acs.orglett.8b00883. Epub 2018 Apr 6. [PubMed:29624065 ]