NP-MRD: Showing NP-Card for (4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0223697)

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Record Information

Version

2.0

Created at

2022-09-06 01:52:12 UTC

Updated at

2022-09-06 01:52:12 UTC

NP-MRD ID

NP0223697

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Macedonine 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. Based on a literature review very few articles have been published on Macedonine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062203522D          

 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  2  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
    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  2  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
    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
  4  2  1  6  0  0  0
  4  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  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 13  1  6  0  0  0
  4 15  1  0  0  0  0
  8 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=C[C@H](O)[C@H]2[C@@H]1COC[C@H]2C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O5/c11-2-5-1-8(12)9-6(5)3-15-4-7(9)10(13)14/h1,6-9,11-12H,2-4H2,(H,13,14)/t6-,7-,8+,9+/m1/s1

> <INCHI_KEY>
DIIADJQOLFWUFJ-HXFLIBJXSA-N

> <FORMULA>
C10H14O5

> <MOLECULAR_WEIGHT>
214.217

> <EXACT_MASS>
214.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.77938677617012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,4aS,5R,7aS)-5-hydroxy-7-(hydroxymethyl)-1H,3H,4H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <JCHEM_LOGP>
-1.5657866536666671

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.433722682333642

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.118943282317874

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7394712936484407

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
51.6712

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aS,5R,7aS)-5-hydroxy-7-(hydroxymethyl)-1H,3H,4H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-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  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.877  -3.085   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+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                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₄O₅

Average Mass

214.2170 Da

Monoisotopic Mass

214.08412 Da

IUPAC Name

(4S,4aS,5R,7aS)-5-hydroxy-7-(hydroxymethyl)-1H,3H,4H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid

Traditional Name

(4S,4aS,5R,7aS)-5-hydroxy-7-(hydroxymethyl)-1H,3H,4H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

OCC1=C[C@H](O)[C@H]2[C@@H]1COC[C@H]2C(O)=O

InChI Identifier

InChI=1S/C10H14O5/c11-2-5-1-8(12)9-6(5)3-15-4-7(9)10(13)14/h1,6-9,11-12H,2-4H2,(H,13,14)/t6-,7-,8+,9+/m1/s1

InChI Key

DIIADJQOLFWUFJ-HXFLIBJXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Oxane
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Hydrocarbon derivative
Primary alcohol
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	-1.6	ChemAxon
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	51.67 m³·mol⁻¹	ChemAxon
Polarizability	20.78 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

57535074

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71355980

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0223697)

MOL for NP0223697 ((4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D MOL for NP0223697 ((4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D SDF for NP0223697 ((4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D-SDF for NP0223697 ((4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

PDB for NP0223697 ((4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D PDB for NP0223697 ((4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

SMILES for NP0223697 ((4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

INCHI for NP0223697 ((4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

Structure for NP0223697 ((4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D Structure for NP0223697 ((4s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,3h,4h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)