NP-MRD: Showing NP-Card for (-)-Glycinol (NP0051468)

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Record Information

Version

2.0

Created at

2022-04-27 22:49:26 UTC

Updated at

2022-04-27 22:49:26 UTC

NP-MRD ID

NP0051468

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Glycinol

Description

3,6,9-Trihydroxypterocarpan, also known as glycinol, belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, 3,6,9-trihydroxypterocarpan is considered to be a flavonoid lipid molecule. (-)-Glycinol is found in Erythrina sandwicensis, Glycine max , Oxyrhynchus volubilis, Phaseolus coccineus , Pueraria montana, Pueraria montana var. lobata, Pueraria thunbergiana , Teramnus micans, Teramnus uncinatus and Vigna mungo . (-)-Glycinol was first documented in 1981 (PMID: 16661917). 3,6,9-Trihydroxypterocarpan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 16250441) (PMID: 16663042) (PMID: 19116342) (PMID: 19943626).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 35  0  0  0  0  0  0  0  0999 V2000
    5.8347    0.1898    0.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4571    0.2577    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9258    1.2343   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5550    1.3204   -0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795    0.4262   -0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2131   -0.5496    0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5863   -0.6331    0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3411   -1.4341    1.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0580   -1.7337    0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349   -0.8907   -0.5167 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3122   -1.5254   -1.7479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8456   -0.5254   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0604   -1.1296   -0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2609   -0.5693   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2150    0.6428    0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3976    1.2471    0.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0009    1.2519    0.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7962    0.6880    0.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4530    1.0975    0.5600 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2293    0.4695   -0.5376 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2775    0.7040    1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5401    1.9701   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1131    2.0801   -1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9930   -1.3983    1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0491   -2.8231    0.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6239   -1.6718    1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7335   -0.9057   -2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1211   -2.0912   -0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2115   -1.0714   -0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3634    2.1439    1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600    2.2202    1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627    1.0092   -1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 12 10  1  0
 10 11  1  6
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  2  7  2  0
 10 20  1  0
  7  6  1  0
  5 20  1  0
 17 18  1  0
 20 32  1  6
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 11 27  1  0
  9 25  1  0
  9 26  1  0
  4 23  1  0
  3 22  1  0
  1 21  1  0
  7 24  1  0
M  END

Glycinol
  Mrv1652309271700162D          

 21 24  0  0  0  0            999 V2000
    1.8728   -4.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6029   -3.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1569   -2.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5350   -2.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3591   -2.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8050   -2.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0455   -1.4876    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7261   -1.1956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016   -0.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6882   -0.2113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -0.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4722   -1.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090   -1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8988   -1.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8517   -0.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413   -0.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1147   -0.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7824   -1.8585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6573   -2.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -2.3045    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
 19 21  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051468

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12OC3=C(C=CC(O)=C3)[C@]1(O)COC1=C2C=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-8-1-3-10-12(5-8)19-7-15(18)11-4-2-9(17)6-13(11)20-14(10)15/h1-6,14,16-18H,7H2/t14-,15+/m0/s1

> <INCHI_KEY>
QMXOFBXZEKTJIK-LSDHHAIUSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.256

> <EXACT_MASS>
272.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.925583096004374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10S)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,10,14-triol

> <ALOGPS_LOGP>
1.57

> <JCHEM_LOGP>
1.708148958333333

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.705735069781737

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.104196321979753

> <JCHEM_PKA_STRONGEST_BASIC>
-4.093074864333841

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
69.66670000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10S)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,10,14-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Glycinol                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-17         0                                  
HETATM    1  O   UNK     0       3.496  -7.758   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.664  -6.462   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.125  -6.535   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.293  -5.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.999  -3.871   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.537  -3.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.369  -5.093   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.085  -2.777   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.355  -2.232   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.003  -1.239   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.285  -0.394   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.660  -1.087   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.748  -2.624   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.123  -3.317   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.411  -2.472   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.323  -0.934   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.610  -0.089   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.947  -0.242   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.460  -3.469   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.227  -4.991   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      -2.756  -4.302   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   10   19                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12                                                       
CONECT   19   13    8   20   21                                             
CONECT   20   19    4                                                       
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
(-)-Glycinol	ChEBI
(6AlphaS,11alphas)-3,6alpha,9-trihydroxypterocarpan	ChEBI
(6AS,11as)-3,6a,9-trihydroxypterocarpan	ChEBI
(6AS-cis)-6H-benzofuro(3,2-c)(1)benzopyran-3,6a,9(11ah)-triol	ChEBI
6H-Benzofuro[3,2-c][1]benzopyran-3,6a,9(11ah)-triol	ChEBI
Glycinol	ChEBI
(6AlphaS,11alphas)-3,6a,9-trihydroxypterocarpan	Generator
(6AlphaS,11alphas)-3,6α,9-trihydroxypterocarpan	Generator
3,6,9-Trihydroxypterocarpan	MeSH

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2560 Da

Monoisotopic Mass

272.06847 Da

IUPAC Name

(1S,10S)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,10,14-triol

Traditional Name

(1S,10S)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,10,14-triol

CAS Registry Number

Not Available

SMILES

[H][C@@]12OC3=C(C=CC(O)=C3)[C@]1(O)COC1=C2C=CC(O)=C1

InChI Identifier

InChI=1S/C15H12O5/c16-8-1-3-10-12(5-8)19-7-15(18)11-4-2-9(17)6-13(11)20-14(10)15/h1-6,14,16-18H,7H2/t14-,15+/m0/s1

InChI Key

QMXOFBXZEKTJIK-LSDHHAIUSA-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
Erythrina sandwicensis	Plant	KNApSAcK
Glycine max	Plant	KNApSAcK
Oxyrhynchus volubilis	Plant	KNApSAcK
Phaseolus coccineus	Plant	KNApSAcK
Pueraria montana	LOTUS Database	35616633
Pueraria montana var. lobata	Plant	KNApSAcK
Pueraria thunbergiana	Plant	KNApSAcK
Teramnus micans	Plant	KNApSAcK
Teramnus uncinatus	Plant	KNApSAcK
Vigna mungo	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Chromane
Benzopyran
1-benzopyran
Coumaran
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pterocarpans (CHEBI:15649 )
pterocarpans (C01263 )
Pterocarpanes (C01263 )
Pterocarpans (LMPK12070128 )

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	1.57	ALOGPS
logP	1.71	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.67 m³·mol⁻¹	ChemAxon
Polarizability	26.93 Å³	ChemAxon
Number of Rings	4	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

C00002532

Chemspider ID

Not Available

KEGG Compound ID

C01263

BioCyc ID

6AS11AS-36A9-TRIHYDROXYPTEROCARPAN

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129648

PDB ID

Not Available

ChEBI ID

15649

Good Scents ID

Not Available

References

General References

Qi Y, Moco S, Boeren S, De Vos CH, Bovy A: [Isolation and identification of glycinol from Glycine max [L.] Merri]. Se Pu. 2005 Jul;23(4):353-7. [PubMed:16250441 ]
Weinstein LI, Hahn MG, Albersheim P: Host-Pathogen Interactions : XVIII. ISOLATION AND BIOLOGICAL ACTIVITY OF GLYCINOL, A PTEROCARPAN PHYTOALEXIN SYNTHESIZED BY SOYBEANS. Plant Physiol. 1981 Aug;68(2):358-63. doi: 10.1104/pp.68.2.358. [PubMed:16661917 ]
Weinstein LI, Albersheim P: Host-Pathogen Interactions : XXIII. The Mechanism of the Antibacterial Action of Glycinol, a Pterocarpan Phytoalexin Synthesized by Soybeans. Plant Physiol. 1983 Jun;72(2):557-63. doi: 10.1104/pp.72.2.557. [PubMed:16663042 ]
Boue SM, Tilghman SL, Elliott S, Zimmerman MC, Williams KY, Payton-Stewart F, Miraflor AP, Howell MH, Shih BY, Carter-Wientjes CH, Segar C, Beckman BS, Wiese TE, Cleveland TE, McLachlan JA, Burow ME: Identification of the potent phytoestrogen glycinol in elicited soybean (Glycine max). Endocrinology. 2009 May;150(5):2446-53. doi: 10.1210/en.2008-1235. Epub 2008 Dec 30. [PubMed:19116342 ]
Luniwal A, Khupse RS, Reese M, Fang L, Erhardt PW: Total syntheses of racemic and natural glycinol. J Nat Prod. 2009 Nov;72(11):2072-5. doi: 10.1021/np900509f. [PubMed:19943626 ]

Showing NP-Card for (-)-Glycinol (NP0051468)

MOL for NP0051468 ((-)-Glycinol)

3D MOL for NP0051468 ((-)-Glycinol)

3D SDF for NP0051468 ((-)-Glycinol)

3D-SDF for NP0051468 ((-)-Glycinol)

PDB for NP0051468 ((-)-Glycinol)

3D PDB for NP0051468 ((-)-Glycinol)

SMILES for NP0051468 ((-)-Glycinol)

INCHI for NP0051468 ((-)-Glycinol)

Structure for NP0051468 ((-)-Glycinol)

3D Structure for NP0051468 ((-)-Glycinol)