NP-MRD: Showing NP-Card for (2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol (NP0143473)

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Record Information

Version

2.0

Created at

2022-09-01 22:14:00 UTC

Updated at

2022-09-01 22:14:00 UTC

NP-MRD ID

NP0143473

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol

Description

Sordariol belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. (2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol is found in Sordaria macrospora. Based on a literature review very few articles have been published on Sordariol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    3.2727    0.0513   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456   -0.8322    0.0166 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6647   -0.8481    0.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4959   -0.3333    1.1465 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8198    0.9342    1.5789 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0229   -0.4514    0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758    0.5457    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792    0.7071   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456    1.9098   -0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117    2.1884   -1.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6132    1.2687   -0.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3022    0.0740   -0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3053   -0.8550   -0.1494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9875   -0.1925    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8005   -1.4989    0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0562   -2.1709    0.7727 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -0.2597   -1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3399   -0.1081   -1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4247    1.1146   -0.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9963   -1.8453   -0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2698   -0.8879   -0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6549   -1.0221    2.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0532    1.4680    1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5233   -1.3524    0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0177    1.4568    0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831    2.6472   -0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8459    3.1410   -1.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288    1.4638   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2484   -0.6633   -0.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1947   -2.1662    0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4651   -1.4697    1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4239   -2.0139    1.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 14  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  6
  3 21  1  0
  4 22  1  1
  5 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
M  END


  Mrv1652309022200142D          

 16 16  0  0  1  0            999 V2000
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0143473

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@@H](O)\C=C\C1=CC=CC(O)=C1CO

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O4/c1-8(14)11(15)6-5-9-3-2-4-12(16)10(9)7-13/h2-6,8,11,13-16H,7H2,1H3/b6-5+/t8-,11+/m1/s1

> <INCHI_KEY>
MCAIMPGCWVIODY-ZPTAOWOPSA-N

> <FORMULA>
C12H16O4

> <MOLECULAR_WEIGHT>
224.256

> <EXACT_MASS>
224.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.687165988426035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4E)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol

> <ALOGPS_LOGP>
0.00

> <JCHEM_LOGP>
0.5311367156666664

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.717058666604423

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.82250915278159

> <JCHEM_PKA_STRONGEST_BASIC>
-2.958582233849911

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
62.37060000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4E)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₆O₄

Average Mass

224.2560 Da

Monoisotopic Mass

224.10486 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@@H](O)\C=C\C1=CC=CC(O)=C1CO

InChI Identifier

InChI=1S/C12H16O4/c1-8(14)11(15)6-5-9-3-2-4-12(16)10(9)7-13/h2-6,8,11,13-16H,7H2,1H3/b6-5+/t8-,11+/m1/s1

InChI Key

MCAIMPGCWVIODY-ZPTAOWOPSA-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
Sordaria macrospora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamyl alcohols

Sub Class

Not Available

Direct Parent

Cinnamyl alcohols

Alternative Parents

Substituents

Cinnamyl alcohol
Benzyl alcohol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Alcohol
Organooxygen compound
Aromatic alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary 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	0	ALOGPS
logS	-2	ALOGPS

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045474

Chemspider ID

4947370

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443347

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol (NP0143473)

MOL for NP0143473 ((2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol)

3D MOL for NP0143473 ((2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol)

3D SDF for NP0143473 ((2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol)

3D-SDF for NP0143473 ((2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol)

PDB for NP0143473 ((2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol)

3D PDB for NP0143473 ((2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol)

SMILES for NP0143473 ((2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol)

INCHI for NP0143473 ((2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol)

Structure for NP0143473 ((2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol)

3D Structure for NP0143473 ((2r,3s,4e)-5-[3-hydroxy-2-(hydroxymethyl)phenyl]pent-4-ene-2,3-diol)