NP-MRD: Showing NP-Card for 6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one (NP0142569)

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Record Information

Version

2.0

Created at

2022-09-01 21:08:43 UTC

Updated at

2022-09-01 21:08:43 UTC

NP-MRD ID

NP0142569

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one

Description

Glycolic acid, also known as 2-hydroxyacetate or glycolate, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated. Glycolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycolic acid exists in all living species, ranging from bacteria to humans. In humans, glycolic acid is involved in rosiglitazone metabolism pathway. Outside of the human body, Glycolic acid has been detected, but not quantified in, several different foods, such as sunburst squash (pattypan squash), sweet oranges, cereals and cereal products, bog bilberries, and mixed nuts. This could make glycolic acid a potential biomarker for the consumption of these foods. Glycolic acid is a potentially toxic compound. 6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one is found in Physalis peruviana. 6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one was first documented in 2002 (PMID: 18498500). Glycolic acid, with regard to humans, has been found to be associated with several diseases such as branched-chain keto acid dehydrogenase kinase deficiency, ethylene glycol poisoning, and transurethral resection of the prostate; glycolic acid has also been linked to several inborn metabolic disorders including glutaric acidemia type 2 and glycolic aciduria (PMID: 14585457) (PMID: 15662707) (PMID: 15716481) (PMID: 15716482).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241215132D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241215132D          

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   -1.1075   -1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075   -1.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8211   -2.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8211   -3.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0445    1.3132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3912    0.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8766   -0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3912   -1.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -0.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -1.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361   -2.8091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361   -1.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511   -2.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511   -3.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  2  3  1  0  0  0  0
  2 19  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  2  0  0  0  0
  6  7  2  0  0  0  0
  6 36  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 22  1  0  0  0  0
 10 11  1  0  0  0  0
 10 23  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 29  1  0  0  0  0
 12 32  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 29  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 35  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 32  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 35  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0142569

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(O)C4(O)C(O)C=CC(=O)C4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O9/c1-14-12-21(37-22(32)15(14)2)25(5,33)27(35)11-10-26(34)17-13-20(31)28(36)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,19-21,30-31,33-36H,8-13H2,1-5H3

> <INCHI_KEY>
XLUKITCTLVOOAW-UHFFFAOYSA-N

> <FORMULA>
C28H40O9

> <MOLECULAR_WEIGHT>
520.6118

> <EXACT_MASS>
520.267232878

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
55.204986713785615

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(1-hydroxy-1-{6,7,8,11,14-pentahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}ethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
0.64

> <JCHEM_LOGP>
0.6129110536666662

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.832879166261797

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.171071017695471

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2010086080161955

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
133.12939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(1-hydroxy-1-{6,7,8,11,14-pentahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}ethyl)-3,4-dimethyl-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.732   1.394   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.400   2.164   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.400   3.704   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.732   4.474   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.732   6.014   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.401  -3.704   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.401  -2.164   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.069  -1.394   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.069   0.146   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.399   0.146   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.129   0.798   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.732   0.146   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.840   1.684   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.401   4.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.066   3.704   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.066   2.164   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.401   1.394   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.295   2.726   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.065   1.394   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.835   0.059   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.734  -0.623   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.734  -2.164   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.399  -1.394   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.067  -2.164   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.067  -3.704   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.399  -4.474   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.399  -6.014   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.083   2.451   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.730   0.624   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.636  -0.623   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.730  -1.868   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.630  -1.332   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.304  -2.898   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.734  -5.244   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.734  -3.704   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.069  -4.474   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.069  -6.014   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4                                                            
CONECT    6    7   36                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8                                                            
CONECT   10   11   23                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   29   32                                             
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    4   14   16                                                  
CONECT   16    1   15   17                                                  
CONECT   17   16                                                            
CONECT   18   19                                                            
CONECT   19    2   18   20   29                                             
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22    8   21   23   35                                             
CONECT   23   10   22   24                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29   12   19   28   30                                             
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   12   24   31   33                                             
CONECT   33   32                                                            
CONECT   34   35                                                            
CONECT   35   22   26   34   36                                             
CONECT   36    6   35   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxyacetic acid	ChEBI
2-Hydroxyethanoic acid	ChEBI
alpha-Hydroxyacetic acid	ChEBI
Glycollic acid	ChEBI
HOCH2COOH	ChEBI
Hydroxyacetic acid	ChEBI
Hydroxyethanoic acid	ChEBI
2-Hydroxyacetate	Generator
2-Hydroxyethanoate	Generator
a-Hydroxyacetate	Generator
a-Hydroxyacetic acid	Generator
alpha-Hydroxyacetate	Generator
Α-hydroxyacetate	Generator
Α-hydroxyacetic acid	Generator
Glycollate	Generator
Hydroxyacetate	Generator
Hydroxyethanoate	Generator
Glycolate	Generator
Glycocide	HMDB
GlyPure	HMDB
GlyPure 70	HMDB
Sodium glycolate	HMDB
Glycolic acid, 2-(14)C-labeled	HMDB
Glycolic acid, 1-(14)C-labeled	HMDB
Glycolic acid, potassium salt	HMDB
Glycolic acid, monopotassium salt	HMDB
Glycolic acid, calcium salt	HMDB
Glycolic acid, monoammonium salt	HMDB
Glycolic acid, monolithium salt	HMDB
Glycolic acid, monosodium salt	HMDB
Potassium glycolate	HMDB

Chemical Formula

C₂₈H₄₀O₉

Average Mass

520.6118 Da

Monoisotopic Mass

520.26723 Da

IUPAC Name

6-(1-hydroxy-1-{6,7,8,11,14-pentahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}ethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

Traditional Name

6-(1-hydroxy-1-{6,7,8,11,14-pentahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}ethyl)-3,4-dimethyl-5,6-dihydropyran-2-one

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(O)C4(O)C(O)C=CC(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H40O9/c1-14-12-21(37-22(32)15(14)2)25(5,33)27(35)11-10-26(34)17-13-20(31)28(36)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,19-21,30-31,33-36H,8-13H2,1-5H3

InChI Key

XLUKITCTLVOOAW-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
Physalis peruviana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents

Substituents

Alpha-hydroxy acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:17497 )
2-hydroxy monocarboxylic acid (CHEBI:17497 )

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	0.64	ALOGPS
logP	0.61	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.13 m³·mol⁻¹	ChemAxon
Polarizability	55.2 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000115

DrugBank ID

DB03085

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17497

Good Scents ID

Not Available

References

General References

Woo MY, Greenway DC, Nadler SP, Cardinal P: Artifactual elevation of lactate in ethylene glycol poisoning. J Emerg Med. 2003 Oct;25(3):289-93. doi: 10.1016/s0736-4679(03)00203-8. [PubMed:14585457 ]
Carney EW, Scialli AR, Watson RE, DeSesso JM: Mechanisms regulating toxicant disposition to the embryo during early pregnancy: an interspecies comparison. Birth Defects Res C Embryo Today. 2004 Dec;72(4):345-60. doi: 10.1002/bdrc.20027. [PubMed:15662707 ]
Corley RA, McMartin KE: Incorporation of therapeutic interventions in physiologically based pharmacokinetic modeling of human clinical case reports of accidental or intentional overdosing with ethylene glycol. Toxicol Sci. 2005 May;85(1):491-501. doi: 10.1093/toxsci/kfi120. Epub 2005 Feb 16. [PubMed:15716481 ]
Corley RA, Bartels MJ, Carney EW, Weitz KK, Soelberg JJ, Gies RA, Thrall KD: Development of a physiologically based pharmacokinetic model for ethylene glycol and its metabolite, glycolic Acid, in rats and humans. Toxicol Sci. 2005 May;85(1):476-90. doi: 10.1093/toxsci/kfi119. Epub 2005 Feb 16. [PubMed:15716482 ]
Couch LH, Howard PC: Quantification of glycolic acid in cosmetic products using reversed phase high performance liquid chromatography. Int J Cosmet Sci. 2002 Apr;24(2):89-95. doi: 10.1046/j.1467-2494.2002.00128.x. [PubMed:18498500 ]
LOTUS database [Link]

Showing NP-Card for 6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one (NP0142569)

MOL for NP0142569 (6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D MOL for NP0142569 (6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D SDF for NP0142569 (6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D-SDF for NP0142569 (6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

PDB for NP0142569 (6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D PDB for NP0142569 (6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

SMILES for NP0142569 (6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

INCHI for NP0142569 (6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

Structure for NP0142569 (6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D Structure for NP0142569 (6-(1-{1,3a,5,5a,6-pentahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)