NP-MRD: Showing NP-Card for 2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol (NP0160541)

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Record Information

Version

2.0

Created at

2022-09-02 18:31:05 UTC

Updated at

2022-09-02 18:31:05 UTC

NP-MRD ID

NP0160541

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol

Description

2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol is found in Sesamum indicum.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.4951   -3.3364   -1.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1442   -2.6168   -2.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596   -1.2952   -1.5619 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6849   -1.7574   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -0.8879    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6946   -0.3983   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910    0.4449    0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0514    0.8070    1.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508    0.3306    2.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3978    0.6900    3.6041 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0958   -0.5065    1.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2765   -0.2915   -1.3111 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1055    1.0490   -0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9793    1.7360   -1.6462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418   -0.7854   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4727    0.2349   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5211    0.4747   -1.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234    1.4401   -0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3346    2.1970    0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3008    1.9841    1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1584    2.7216    2.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3797    0.9883    0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0711   -4.2035   -0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028   -2.4351   -3.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0599   -3.2147   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3742   -0.9978   -2.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3971   -2.5588   -0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748   -2.4048    0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038   -0.6908   -1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4254    0.8012    0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6446    1.4639    2.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217    1.5361    3.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1525   -0.8580    1.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241   -0.0551   -2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3134    1.1555    0.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8585    1.6709   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    2.6887   -1.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0407   -1.0905    0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9922   -1.6348   -0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5502   -0.1427   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2417    1.6050   -1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0721    2.9643    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6219    2.3371    3.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5702    0.8413    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5 11  2  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  3 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 22  2  0
 22 20  1  0
 20 21  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
  6  5  1  0
 17 16  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  6
  4 27  1  0
  4 28  1  0
 11 33  1  0
 10 32  1  0
  8 31  1  0
  7 30  1  0
  6 29  1  0
 12 34  1  6
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 22 44  1  0
 21 43  1  0
 19 42  1  0
 18 41  1  0
 17 40  1  0
M  END


  Mrv1652305221920482D          

 22 23  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  2  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 16 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17  5  2  0  0  0  0
 17  9  1  0  0  0  0
 18  6  2  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160541

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(CC1=CC(O)=CC=C1)C(CO)CC1=CC(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2

> <INCHI_KEY>
DWONJCNDULPHLV-UHFFFAOYSA-N

> <FORMULA>
C18H22O4

> <MOLECULAR_WEIGHT>
302.3649

> <EXACT_MASS>
302.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.337274575272815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.648203614

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.395474277447398

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.793418141582793

> <JCHEM_PKA_STRONGEST_BASIC>
-2.603209181436301

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
86.3606

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1   13                                                       
CONECT    4    2   14                                                       
CONECT    5    1   17                                                       
CONECT    6    2   18                                                       
CONECT    7   13   15                                                       
CONECT    8   14   16                                                       
CONECT    9   13   17                                                       
CONECT   10   14   18                                                       
CONECT   11   15   19                                                       
CONECT   12   16   20                                                       
CONECT   13    3    7    9                                                  
CONECT   14    4    8   10                                                  
CONECT   15    7   11   16                                                  
CONECT   16    8   12   15                                                  
CONECT   17    5    9   21                                                  
CONECT   18    6   10   22                                                  
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   17                                                            
CONECT   22   18                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
2,3-Bis(3'-hydroxybenzyl)butane-1,4-diol	MeSH
2,3-Bis(3-hydroxybenzyl)butane-1,4-diol	MeSH

Chemical Formula

C₁₈H₂₂O₄

Average Mass

302.3649 Da

Monoisotopic Mass

302.15181 Da

IUPAC Name

2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol

Traditional Name

2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol

CAS Registry Number

Not Available

SMILES

OCC(CC1=CC(O)=CC=C1)C(CO)CC1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2

InChI Key

DWONJCNDULPHLV-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
Sesamum indicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Dibenzylbutanediol lignans

Direct Parent

Dibenzylbutanediol lignans

Alternative Parents

Substituents

Dibenzylbutanediol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.91	ALOGPS
logP	2.65	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.79	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.36 m³·mol⁻¹	ChemAxon
Polarizability	32.34 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021828

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Enterodiol

METLIN ID

Not Available

PubChem Compound

123725

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol (NP0160541)

MOL for NP0160541 (2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol)

3D MOL for NP0160541 (2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol)

3D SDF for NP0160541 (2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol)

3D-SDF for NP0160541 (2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol)

PDB for NP0160541 (2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol)

3D PDB for NP0160541 (2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol)

SMILES for NP0160541 (2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol)

INCHI for NP0160541 (2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol)

Structure for NP0160541 (2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol)

3D Structure for NP0160541 (2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol)