NP-MRD: Showing NP-Card for (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol (NP0091922)

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Record Information

Version

2.0

Created at

2022-05-11 18:52:07 UTC

Updated at

2022-05-11 18:52:07 UTC

NP-MRD ID

NP0091922

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol

Description

(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol, also known as (1R,2R)-hydrobenzoin, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). This is a key hepatic enzyme that is involved in the metabolism of numerous xenobiotics, such as 1,3-butadiene oxide, styrene oxide and the polycyclic aromatic hydrocarbon benzopyrene 4,5-oxide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    0.5955    1.0639    1.9339 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7044   -0.1711    1.3401 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6379   -0.1393    0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191    0.8935   -0.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131    0.8856   -1.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4595   -0.1770   -1.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3879   -1.2252   -1.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.2208   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6109   -0.7941    1.1141 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4874   -2.0476    0.4743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6355   -0.0471    0.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6630    1.3102    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6926    1.9052   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6851    1.1120   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6781   -0.2508   -0.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6866   -0.8070   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640    1.2586    2.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2742   -0.7881    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862    1.7633   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575    1.7147   -2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1514   -0.1739   -2.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640   -2.0761   -1.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4808   -2.0631    0.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632   -1.0164    2.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1691   -2.7127    1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967    1.9457    0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7095    2.9762   -0.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4691    1.6165   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4701   -0.8370   -1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6887   -1.8980   -0.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
 16 11  1  0
  8  3  1  0
  1 17  1  0
  2 18  1  1
  9 24  1  1
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
M  END


  Mrv0541 02241203392D          

 16 17  0  0  1  0            999 V2000
   14.0136   -7.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6637  -10.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1887   -7.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4261   -7.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2511   -9.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2511  -10.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7762   -7.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0136   -8.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4261   -9.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4261  -10.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1887   -8.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0136  -10.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7762   -9.3228    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1887  -10.0368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9512   -9.3228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7762  -10.7514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  6  0  0  0
 13 14  1  0  0  0  0
 14 16  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0091922

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]([C@H](O)C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-16H/t13-,14-/m1/s1

> <INCHI_KEY>
IHPDTPWNFBQHEB-ZIAGYGMSSA-N

> <FORMULA>
C14H14O2

> <MOLECULAR_WEIGHT>
214.2598

> <EXACT_MASS>
214.099379692

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.850432367361698

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R)-1,2-diphenylethane-1,2-diol

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.3598012939999995

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.530859354576034

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.081236811022443

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5063964987553575

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
63.119200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-hydrobenzoin

> <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  C   UNK     0      26.159 -13.401   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.239 -18.735   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.619 -13.401   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.929 -14.735   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.469 -17.403   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.469 -20.069   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.849 -14.735   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.159 -16.069   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.929 -17.403   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.929 -20.069   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.619 -16.069   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.159 -18.735   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.849 -17.403   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.619 -18.735   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      22.309 -17.403   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      23.849 -20.069   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   11                                                       
CONECT    9    5   12                                                       
CONECT   10    6   12                                                       
CONECT   11    7    8   13                                                  
CONECT   12    9   10   14                                                  
CONECT   13   11   15   14                                                  
CONECT   14   12   13   16                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(+)-Hydrobenzoin	ChEBI
(1R,2R)-Hydrobenzoin	ChEBI
(R,R)-(+)-Hydrobenzoin	ChEBI
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol	ChEBI

Chemical Formula

C₁₄H₁₄O₂

Average Mass

214.2598 Da

Monoisotopic Mass

214.09938 Da

IUPAC Name

(1R,2R)-1,2-diphenylethane-1,2-diol

Traditional Name

(+)-hydrobenzoin

CAS Registry Number

Not Available

SMILES

O[C@@H]([C@H](O)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H14O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-16H/t13-,14-/m1/s1

InChI Key

IHPDTPWNFBQHEB-ZIAGYGMSSA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
1,2-diol
Organic oxygen compound
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydrobenzoin (CHEBI:50014 )

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	2.05	ALOGPS
logP	2.36	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.08	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.12 m³·mol⁻¹	ChemAxon
Polarizability	22.85 Å³	ChemAxon
Number of Rings	2	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

HMDB0012111

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028775

KNApSAcK ID

Not Available

Chemspider ID

745456

KEGG Compound ID

C16015

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

853019

PDB ID

Not Available

ChEBI ID

50014

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol (NP0091922)

MOL for NP0091922 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

3D MOL for NP0091922 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

3D SDF for NP0091922 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

3D-SDF for NP0091922 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

PDB for NP0091922 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

3D PDB for NP0091922 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

SMILES for NP0091922 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

INCHI for NP0091922 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

Structure for NP0091922 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

3D Structure for NP0091922 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)