NP-MRD: Showing NP-Card for 2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde (NP0276283)

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Record Information

Version

2.0

Created at

2022-09-09 00:19:14 UTC

Updated at

2022-09-09 00:19:14 UTC

NP-MRD ID

NP0276283

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde

Description

2,5-Dihydroxy-3-[(2E,6E,10E,14E)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde is found in Desmarestia menziesii. Based on a literature review very few articles have been published on 2,5-dihydroxy-3-[(2E,6E,10E,14E)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092202192D          

 31 31  0  0  0  0            999 V2000
   -3.5724   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   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
    2.1434   -0.4125    0.0000 O   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 C   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   10.7250    0.0000 O   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
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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  9 10  1  0  0  0  0
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 28 29  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

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   -8.5979   -1.3361    2.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309092202192D          

 31 31  0  0  0  0            999 V2000
   -3.5724   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0276283

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC(O)=CC(C=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O4/c1-20(8-5-9-21(2)11-7-13-23(4)18-28)10-6-12-22(3)14-15-24-16-26(30)17-25(19-29)27(24)31/h9-10,13-14,16-17,19,28,30-31H,5-8,11-12,15,18H2,1-4H3/b20-10+,21-9+,22-14+,23-13+

> <INCHI_KEY>
HGIIBFHOBBXWNR-QHBWFRILSA-N

> <FORMULA>
C27H38O4

> <MOLECULAR_WEIGHT>
426.597

> <EXACT_MASS>
426.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.60093061211132

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dihydroxy-3-[(2E,6E,10E,14E)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde

> <JCHEM_LOGP>
7.155556184999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.688899214626382

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.592030156739023

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0797068162575387

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
134.0291

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-3-[(2E,6E,10E,14E)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  20.790   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002  20.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002  18.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  17.710   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  15.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -9.336  20.790   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -10.669  20.020   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   20   29                                                  
CONECT   29   28                                                            
CONECT   30    2   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₄

Average Mass

426.5970 Da

Monoisotopic Mass

426.27701 Da

IUPAC Name

2,5-dihydroxy-3-[(2E,6E,10E,14E)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde

Traditional Name

2,5-dihydroxy-3-[(2E,6E,10E,14E)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde

CAS Registry Number

Not Available

SMILES

C\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC(O)=CC(C=O)=C1O

InChI Identifier

InChI=1S/C27H38O4/c1-20(8-5-9-21(2)11-7-13-23(4)18-28)10-6-12-22(3)14-15-24-16-26(30)17-25(19-29)27(24)31/h9-10,13-14,16-17,19,28,30-31H,5-8,11-12,15,18H2,1-4H3/b20-10+,21-9+,22-14+,23-13+

InChI Key

HGIIBFHOBBXWNR-QHBWFRILSA-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
Desmarestia menziesii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Long chain fatty alcohol
Prenylbenzoquinol
Fatty alcohol
Hydroxybenzaldehyde
Benzaldehyde
Benzoyl
Hydroquinone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl-aldehyde
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	7.16	ChemAxon
pKa (Strongest Acidic)	8.59	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	134.03 m³·mol⁻¹	ChemAxon
Polarizability	51.6 Å³	ChemAxon
Number of Rings	1	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10472098

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14683209

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde (NP0276283)

MOL for NP0276283 (2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde)

3D MOL for NP0276283 (2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde)

3D SDF for NP0276283 (2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde)

3D-SDF for NP0276283 (2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde)

PDB for NP0276283 (2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde)

3D PDB for NP0276283 (2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde)

SMILES for NP0276283 (2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde)

INCHI for NP0276283 (2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde)

Structure for NP0276283 (2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde)

3D Structure for NP0276283 (2,5-dihydroxy-3-[(2e,6e,10e,14e)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzaldehyde)