NP-MRD: Showing NP-Card for (1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0253474)

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Record Information

Version

2.0

Created at

2022-09-07 17:20:53 UTC

Updated at

2022-09-07 17:20:53 UTC

NP-MRD ID

NP0253474

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid

Description

SCHEMBL16034417 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. (1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid is found in Garrya elliptica. Based on a literature review very few articles have been published on SCHEMBL16034417.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072219202D          

 15 16  0  0  1  0            999 V2000
    3.9934    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
    2.5645    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  1  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  2  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
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769   -1.6527    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
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
  4 15  1  0  0  0  0
  9 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253474

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC[C@H]2[C@@H]1[C@H](O)OC=C2C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O5/c11-3-5-1-2-6-7(9(12)13)4-15-10(14)8(5)6/h1,4,6,8,10-11,14H,2-3H2,(H,12,13)/t6-,8-,10-/m1/s1

> <INCHI_KEY>
SLUWJPWHBUWROV-GTNGPMTGSA-N

> <FORMULA>
C10H12O5

> <MOLECULAR_WEIGHT>
212.201

> <EXACT_MASS>
212.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.13533242133567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <JCHEM_LOGP>
-0.8231230489999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.039370045070946

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.505410720309891

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7354177850612027

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
51.3242

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.877  -3.085   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    4    9                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₂O₅

Average Mass

212.2010 Da

Monoisotopic Mass

212.06847 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OCC1=CC[C@H]2[C@@H]1[C@H](O)OC=C2C(O)=O

InChI Identifier

InChI=1S/C10H12O5/c11-3-5-1-2-6-7(9(12)13)4-15-10(14)8(5)6/h1,4,6,8,10-11,14H,2-3H2,(H,12,13)/t6-,8-,10-/m1/s1

InChI Key

SLUWJPWHBUWROV-GTNGPMTGSA-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
Garrya elliptica	LOTUS Database	35616633

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
Bicyclic monoterpenoid
Vinylogous ester
Hemiacetal
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Alcohol
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

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

75318060

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90407790

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0253474)

MOL for NP0253474 ((1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D MOL for NP0253474 ((1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D SDF for NP0253474 ((1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D-SDF for NP0253474 ((1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

PDB for NP0253474 ((1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D PDB for NP0253474 ((1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

SMILES for NP0253474 ((1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

INCHI for NP0253474 ((1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

Structure for NP0253474 ((1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D Structure for NP0253474 ((1r,4as,7as)-1-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)