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Showing NP-Card for (+)-Cistachlorin (NP0057448)

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Record Information
Version2.0
Created at2022-04-28 02:52:51 UTC
Updated at2022-04-28 02:52:51 UTC
NP-MRD IDNP0057448
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Cistachlorin
Description(1R,4S,5R,7S,11S)-5-chloro-2,10-dioxatricyclo[5.3.1.0⁴,¹¹]Undecan-4-ol belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (+)-Cistachlorin is found in Cistanche salsa and Cistanche tubulosa . Based on a literature review very few articles have been published on (1R,4S,5R,7S,11S)-5-chloro-2,10-dioxatricyclo[5.3.1.0⁴,¹¹]Undecan-4-ol.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0057448 ((+)-Cistachlorin)


  Mrv1652304282204522D          

 13 15  0  0  1  0            999 V2000
    2.9345    0.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559    0.2553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0025   -0.5554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6278   -1.0935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4065   -0.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093   -1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.7867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2975   -0.9838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6721   -0.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907    0.3153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5925   -1.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490   -2.4121    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  1  0  0  0
  9 12  1  6  0  0  0
  8 13  1  1  0  0  0
M  END
Download

3D MOL for NP0057448 ((+)-Cistachlorin)

     RDKit          3D

 26 28  0  0  0  0  0  0  0  0999 V2000
    2.2490    0.1465    1.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031   -0.0131    0.4629 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8327    0.8737   -0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6630    1.4195   -1.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1660    1.6431   -0.0745 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4105    1.9469   -0.5057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4198    1.1097   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732   -0.3236   -0.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9004   -0.7123    0.4018 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0588   -1.6867   -0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -1.4575    0.1200 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5956   -1.9991   -0.9697 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0179    0.4354    0.7704 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0842   -0.3462    1.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4138    1.7269   -0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4127    0.3608   -1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2275    2.5216    0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7241    1.2345    0.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3196    1.3611   -0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9351   -0.9950   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -0.3471   -1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2604   -1.2627    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3736   -2.7358   -0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1554   -1.5227   -1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4194   -2.0389    1.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372    0.6608    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
 11  2  1  0
 13  2  1  0
 13  5  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  5 17  1  1
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  1
 10 23  1  0
 10 24  1  0
 11 25  1  1
 13 26  1  1
M  END
Download

3D SDF for NP0057448 ((+)-Cistachlorin)


  Mrv1652304282204522D          

 13 15  0  0  1  0            999 V2000
    2.9345    0.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559    0.2553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0025   -0.5554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6278   -1.0935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4065   -0.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093   -1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.7867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2975   -0.9838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6721   -0.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907    0.3153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5925   -1.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490   -2.4121    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  1  0  0  0
  9 12  1  6  0  0  0
  8 13  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0057448

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@]12CO[C@H]3OCC[C@@H](C[C@H]1Cl)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C9H13ClO3/c10-6-3-5-1-2-12-8-7(5)9(6,11)4-13-8/h5-8,11H,1-4H2/t5-,6+,7+,8+,9-/m0/s1

> <INCHI_KEY>
HYLRQTWCGVZFFU-CBHQDSPSSA-N

> <FORMULA>
C9H13ClO3

> <MOLECULAR_WEIGHT>
204.65

> <EXACT_MASS>
204.055322

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.262668876563314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,5R,7S,11S)-5-chloro-2,10-dioxatricyclo[5.3.1.0^{4,11}]undecan-4-ol

> <ALOGPS_LOGP>
0.37

> <JCHEM_LOGP>
0.6785947239999999

> <ALOGPS_LOGS>
-0.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.73373490690475

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7900643517198622

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
46.4516

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5R,7S,11S)-5-chloro-2,10-dioxatricyclo[5.3.1.0^{4,11}]undecan-4-ol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0057448 ((+)-Cistachlorin)

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PDB for NP0057448 ((+)-Cistachlorin)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       5.478   0.985   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.024   0.477   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.738  -1.037   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.905  -2.041   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.359  -1.532   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.645  -0.019   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.311  -3.462   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.776  -3.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.422  -1.836   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.255  -0.832   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.849   0.589   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.106  -2.636   0.000  0.00  0.00           O+0
HETATM   13 Cl   UNK     0       1.771  -4.503   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    3   10   12                                             
CONECT   10    9   11                                                       
CONECT   11   10    2                                                       
CONECT   12    9                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   30    0
END

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3D PDB for NP0057448 ((+)-Cistachlorin)
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SMILES for NP0057448 ((+)-Cistachlorin)
O[C@@]12CO[C@H]3OCC[C@@H](C[C@H]1Cl)[C@@H]23
Download
INCHI for NP0057448 ((+)-Cistachlorin)
InChI=1S/C9H13ClO3/c10-6-3-5-1-2-12-8-7(5)9(6,11)4-13-8/h5-8,11H,1-4H2/t5-,6+,7+,8+,9-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H13ClO3
Average Mass204.6500 Da
Monoisotopic Mass204.05532 Da
IUPAC Name(1R,4S,5R,7S,11S)-5-chloro-2,10-dioxatricyclo[5.3.1.0^{4,11}]undecan-4-ol
Traditional Name(1R,4S,5R,7S,11S)-5-chloro-2,10-dioxatricyclo[5.3.1.0^{4,11}]undecan-4-ol
CAS Registry NumberNot Available
SMILES
O[C@@]12CO[C@H]3OCC[C@@H](C[C@H]1Cl)[C@@H]23
InChI Identifier
InChI=1S/C9H13ClO3/c10-6-3-5-1-2-12-8-7(5)9(6,11)4-13-8/h5-8,11H,1-4H2/t5-,6+,7+,8+,9-/m0/s1
InChI KeyHYLRQTWCGVZFFU-CBHQDSPSSA-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
Cistanche salsaPlant
Cistanche tubulosaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentIridoids and derivatives  
Alternative Parents
Substituents
  • Iridoid-skeleton
    • 

  • Furopyran
    • 

  • Pyran
    • 

  • Oxane
    • 

  • Cyclic alcohol
    • 

  • Furan
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Chlorohydrin
    • 

  • Halohydrin
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Organohalogen compound
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Alkyl halide
    • 

  • Alkyl chloride
    • 

  • Organochloride
    • 

  • Organooxygen compound
    • 

  • 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
logP0.37ALOGPS
logP0.68ChemAxon
logS-0.77ALOGPS
pKa (Strongest Acidic)12.73ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.45 m³·mol⁻¹ChemAxon
Polarizability19.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID61577131  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44205315  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available