NP-MRD: Showing NP-Card for methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate (NP0226385)

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Record Information

Version

2.0

Created at

2022-09-06 05:24:42 UTC

Updated at

2022-09-06 05:24:43 UTC

NP-MRD ID

NP0226385

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate

Description

Nahocol B belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate is found in Sargassum autumnale. Based on a literature review very few articles have been published on Nahocol B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062207242D          

 34 34  0  0  0  0            999 V2000
   -5.9072   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7322   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5572   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -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
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    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
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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   -2.8875    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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  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  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END


  Mrv1652309062207242D          

 34 34  0  0  0  0            999 V2000
   -5.9072   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7322   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5572   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -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
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    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
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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   -2.8875    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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  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  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226385

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1=CC(O)=CC=C1OC(C)(CC\C=C(/C)CCCC(C)C(=O)CC=C(C)C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O5/c1-8-29(6,34-27-17-15-25(30)19-24(27)20-28(32)33-7)18-10-12-22(4)11-9-13-23(5)26(31)16-14-21(2)3/h8,12,14-15,17,19,23,30H,1,9-11,13,16,18,20H2,2-7H3/b22-12+

> <INCHI_KEY>
YMFSSKIJSZRDHG-WSDLNYQXSA-N

> <FORMULA>
C29H42O5

> <MOLECULAR_WEIGHT>
470.65

> <EXACT_MASS>
470.303224452

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.929905947686805

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-(5-hydroxy-2-{[(6E)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate

> <JCHEM_LOGP>
7.263478583333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.22512901316199

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.804834290050513

> <JCHEM_PKA_STRONGEST_BASIC>
-4.883373982842399

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
139.9466

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (5-hydroxy-2-{[(6E)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0     -11.027  -9.034   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.567  -9.034   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -14.107  -6.366   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334  -5.390   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  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -14.670  -8.470   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -13.337 -10.780   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -14.670 -13.090   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -14.670 -14.630   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -16.004 -10.780   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -18.672 -10.780   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -20.005 -10.010   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -21.339 -10.780   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   22                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    3   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₂O₅

Average Mass

470.6500 Da

Monoisotopic Mass

470.30322 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)CC1=CC(O)=CC=C1OC(C)(CC\C=C(/C)CCCC(C)C(=O)CC=C(C)C)C=C

InChI Identifier

InChI=1S/C29H42O5/c1-8-29(6,34-27-17-15-25(30)19-24(27)20-28(32)33-7)18-10-12-22(4)11-9-13-23(5)26(31)16-14-21(2)3/h8,12,14-15,17,19,23,30H,1,9-11,13,16,18,20H2,2-7H3/b22-12+

InChI Key

YMFSSKIJSZRDHG-WSDLNYQXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sargassum autumnale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
4-alkoxyphenol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Methyl ester
Carboxylic acid ester
Ketone
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00044261

Chemspider ID

8918333

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10743002

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate (NP0226385)

MOL for NP0226385 (methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate)

3D MOL for NP0226385 (methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate)

3D SDF for NP0226385 (methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate)

3D-SDF for NP0226385 (methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate)

PDB for NP0226385 (methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate)

3D PDB for NP0226385 (methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate)

SMILES for NP0226385 (methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate)

INCHI for NP0226385 (methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate)

Structure for NP0226385 (methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate)

3D Structure for NP0226385 (methyl 2-(5-hydroxy-2-{[(6e)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate)