NP-MRD: Showing NP-Card for methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate (NP0216972)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 17:08:59 UTC

Updated at

2022-09-05 17:08:59 UTC

NP-MRD ID

NP0216972

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate

Description

75853-64-4 Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate is found in Posoqueria latifolia. 75853-64-4 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    4.9216    0.7424   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7939   -0.0971    0.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    0.3665    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3407    1.6054    0.3326 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3305   -0.5091    0.2514 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4107   -1.5268    1.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3705   -2.4650    1.0859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535   -1.9720    0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6306   -2.7777    0.0558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0965   -0.5656    0.8796 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0389    0.2337    0.2361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5133    0.3640   -1.1894 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1574    1.3169   -1.9198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427    0.7354   -0.9021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0643    2.1149   -0.8310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241    0.0477    0.3919 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5084   -0.8069    0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7182    1.0646    1.2783 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7938    0.1031   -0.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0724    1.1579    1.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8246    1.5428   -0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3567   -1.1391   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2509   -1.0478    2.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3945   -2.0273    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9795   -0.3770    1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901    1.2438    0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233   -0.6322   -1.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0073    2.1984   -1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5791    0.3901   -1.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982    2.4021    0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7527   -1.4350    1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4563   -1.4864   -0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3991   -0.1574    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5998    1.3927    0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  1
 11  5  1  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  6
  6 23  1  0
  6 24  1  0
 10 25  1  1
 11 26  1  1
 12 27  1  6
 13 28  1  0
 14 29  1  6
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
M  END


  Mrv1533004191523282D          

 18 19  0  0  0  0            999 V2000
    2.5645    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726   -0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429   -1.0637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1COC(=O)C2C1C(O)C(O)C2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O7/c1-11(16)6-5(7(12)8(11)13)4(9(14)17-2)3-18-10(6)15/h4-8,12-13,16H,3H2,1-2H3

> <INCHI_KEY>
CWCMFEDIQBKDKW-UHFFFAOYSA-N

> <FORMULA>
C11H16O7

> <MOLECULAR_WEIGHT>
260.242

> <EXACT_MASS>
260.089602855

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.20635586898905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 5,6,7-trihydroxy-7-methyl-1-oxo-octahydrocyclopenta[c]pyran-4-carboxylate

> <ALOGPS_LOGP>
-0.88

> <JCHEM_LOGP>
-2.092573745666667

> <ALOGPS_LOGS>
0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.10394040749366

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.857324409453415

> <JCHEM_PKA_STRONGEST_BASIC>
-3.322096727372231

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
56.485699999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.33e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       4.787   6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.189  -1.518   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.627  -1.986   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17   18                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₆O₇

Average Mass

260.2420 Da

Monoisotopic Mass

260.08960 Da

IUPAC Name

methyl 5,6,7-trihydroxy-7-methyl-1-oxo-octahydrocyclopenta[c]pyran-4-carboxylate

Traditional Name

methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1COC(=O)C2C1C(O)C(O)C2(C)O

InChI Identifier

InChI=1S/C11H16O7/c1-11(16)6-5(7(12)8(11)13)4(9(14)17-2)3-18-10(6)15/h4-8,12-13,16H,3H2,1-2H3

InChI Key

CWCMFEDIQBKDKW-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Posoqueria latifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Iridoid-skeleton
Bicyclic monoterpenoid
Monoterpenoid
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Methyl ester
Tertiary alcohol
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen 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	-0.88	ALOGPS
logP	-2.1	ChemAxon
logS	0.11	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	56.49 m³·mol⁻¹	ChemAxon
Polarizability	24.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

156633

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate (NP0216972)

MOL for NP0216972 (methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0216972 (methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0216972 (methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0216972 (methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate)

PDB for NP0216972 (methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0216972 (methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate)

SMILES for NP0216972 (methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate)

INCHI for NP0216972 (methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate)

Structure for NP0216972 (methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0216972 (methyl 5,6,7-trihydroxy-7-methyl-1-oxo-hexahydrocyclopenta[c]pyran-4-carboxylate)