NP-MRD: Showing NP-Card for Jioglutin A (NP0057577)

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Record Information

Version

2.0

Created at

2022-04-28 02:59:45 UTC

Updated at

2022-04-28 02:59:45 UTC

NP-MRD ID

NP0057577

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Jioglutin A

Description

(1S,4S,5R,6S,7R,9S,11S)-5-chloro-9-methoxy-2,10-dioxatricyclo[5.3.1.0⁴,¹¹]Undecane-4,6-diol 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. Jioglutin A is found in Rehmannia glutinosa . Based on a literature review very few articles have been published on (1S,4S,5R,6S,7R,9S,11S)-5-chloro-9-methoxy-2,10-dioxatricyclo[5.3.1.0⁴,¹¹]Undecane-4,6-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    3.9097   -0.0466    0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5394   -0.2573    0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9602    0.0147   -0.7661 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0760    1.2527   -0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407    0.8999    0.0005 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4071    1.1735   -0.9413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6186    2.5177   -1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5331    0.5241   -0.1264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0206    0.3821   -1.0360 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8924   -0.8266    0.1742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3962   -1.4053    1.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833   -1.6762   -1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7407   -1.9327   -1.5270 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080   -1.4913   -0.6296 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2938   -1.0429   -1.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -0.5435    0.3120 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3094   -0.7429   -0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0853    1.0042   -0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4391   -0.2298    1.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7455    0.3318   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.8011   -1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6147    1.9134    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    1.4804    0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575    0.6265   -1.8877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9766    3.0541   -0.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6140    1.0908    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9640   -0.9447    2.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5736   -1.1667   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5126   -2.6247   -0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5336   -2.3998   -0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1065   -0.7362    1.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 15  3  1  0
 16  5  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  6
  4 21  1  0
  4 22  1  0
  5 23  1  1
  6 24  1  6
  7 25  1  0
  8 26  1  1
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  1
 16 31  1  1
M  END


  Mrv1652304282204592D          

 16 18  0  0  1  0            999 V2000
    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  2  0  0  0  0  0  0  0  0  0
    2.6278   -1.0935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4065   -0.8210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -0.0103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9345    0.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3386    0.2622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9639   -0.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093   -1.8545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2975   -0.9838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6721   -0.4457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9907    0.3153    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5514    1.0137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308   -0.6353    0.0000 Cl  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
  2  1  1  6  0  0  0
  2  3  1  0  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  6  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  3  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0057577

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@H]2[C@H](O)[C@@H](Cl)[C@@]3(O)CO[C@@H](O1)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C10H15ClO5/c1-14-5-2-4-6-9(16-5)15-3-10(6,13)8(11)7(4)12/h4-9,12-13H,2-3H2,1H3/t4-,5+,6-,7+,8-,9+,10-/m1/s1

> <INCHI_KEY>
LEJFNTAYIXQPJP-NEYBOIOJSA-N

> <FORMULA>
C10H15ClO5

> <MOLECULAR_WEIGHT>
250.68

> <EXACT_MASS>
250.0608013

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.496098397512817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5R,6S,7R,9S,11S)-5-chloro-9-methoxy-2,10-dioxatricyclo[5.3.1.0^{4,11}]undecane-4,6-diol

> <ALOGPS_LOGP>
-0.38

> <JCHEM_LOGP>
-0.26815405699999956

> <ALOGPS_LOGS>
-0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.919234519673694

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.612731297258744

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3332279632364683

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
53.627599999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,6S,7R,9S,11S)-5-chloro-9-methoxy-2,10-dioxatricyclo[5.3.1.0^{4,11}]undecane-4,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0       4.024   0.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.738  -1.037   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.905  -2.041   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.359  -1.532   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.645  -0.019   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.478   0.985   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.099   0.489   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.266  -0.515   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.311  -3.462   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.776  -3.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.422  -1.836   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.255  -0.832   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.849   0.589   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.029   1.892   0.000  0.00  0.00           O+0
HETATM   15 Cl   UNK     0      -0.244  -1.186   0.000  0.00  0.00          Cl+0
HETATM   16  O   UNK     0       1.106  -2.636   0.000  0.00  0.00           O+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2   12   16                                             
CONECT   12   11   13   15                                                  
CONECT   13   12    1   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₅ClO₅

Average Mass

250.6800 Da

Monoisotopic Mass

250.06080 Da

IUPAC Name

(1S,4S,5R,6S,7R,9S,11S)-5-chloro-9-methoxy-2,10-dioxatricyclo[5.3.1.0^{4,11}]undecane-4,6-diol

Traditional Name

(1S,4S,5R,6S,7R,9S,11S)-5-chloro-9-methoxy-2,10-dioxatricyclo[5.3.1.0^{4,11}]undecane-4,6-diol

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@H]2[C@H](O)[C@@H](Cl)[C@@]3(O)CO[C@@H](O1)[C@@H]23

InChI Identifier

InChI=1S/C10H15ClO5/c1-14-5-2-4-6-9(16-5)15-3-10(6,13)8(11)7(4)12/h4-9,12-13H,2-3H2,1H3/t4-,5+,6-,7+,8-,9+,10-/m1/s1

InChI Key

LEJFNTAYIXQPJP-NEYBOIOJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rehmannia glutinosa	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Iridoid-skeleton
Furopyran
Oxane
Pyran
Cyclic alcohol
Furan
Tetrahydrofuran
Tertiary alcohol
Chlorohydrin
Halohydrin
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Organohalogen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Alkyl halide
Alkyl chloride
Organochloride
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.38	ALOGPS
logP	-0.27	ChemAxon
logS	-0.25	ALOGPS
pKa (Strongest Acidic)	12.61	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	53.63 m³·mol⁻¹	ChemAxon
Polarizability	23.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14413748

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Jioglutin A (NP0057577)

MOL for NP0057577 (Jioglutin A)

3D MOL for NP0057577 (Jioglutin A)

3D SDF for NP0057577 (Jioglutin A)

3D-SDF for NP0057577 (Jioglutin A)

PDB for NP0057577 (Jioglutin A)

3D PDB for NP0057577 (Jioglutin A)

SMILES for NP0057577 (Jioglutin A)

INCHI for NP0057577 (Jioglutin A)

Structure for NP0057577 (Jioglutin A)

3D Structure for NP0057577 (Jioglutin A)