NP-MRD: Showing NP-Card for Nahocol B (NP0079573)

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Record Information

Version

2.0

Created at

2022-04-29 00:35:22 UTC

Updated at

2022-04-29 00:35:22 UTC

NP-MRD ID

NP0079573

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nahocol B

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202352D          

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M  END

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M  END


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  8 28  1  6  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079573

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1=C(O[C@](C)(CC\C=C(\C)CCC[C@@H](C)C(=O)CC=C(C)C)C=C)C=CC(O)=C1

> <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-/t23-,29+/m1/s1

> <INCHI_KEY>
YMFSSKIJSZRDHG-BJVZJOSESA-N

> <FORMULA>
C29H42O5

> <MOLECULAR_WEIGHT>
470.65

> <EXACT_MASS>
470.303224452

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.54647074935415

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.69

> <JCHEM_LOGP>
7.263478583333333

> <ALOGPS_LOGS>
-5.63

> <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>
72.83000000000001

> <JCHEM_REFRACTIVITY>
139.9466

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.772  -3.286   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.002  -1.953   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.232  -5.954   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -9.336 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   26   28                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   16                                                            
CONECT   25   12                                                            
CONECT   26    8   27                                                       
CONECT   27   26                                                            
CONECT   28    8                                                            
CONECT   29    5   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34    3                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-(5-hydroxy-2-{[(3R,6Z,11R)-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetic acid	Generator

Chemical Formula

C₂₉H₄₂O₅

Average Mass

470.6500 Da

Monoisotopic Mass

470.30322 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC(=O)CC1=C(O[C@](C)(CC\C=C(\C)CCC[C@@H](C)C(=O)CC=C(C)C)C=C)C=CC(O)=C1

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-/t23-,29+/m1/s1

InChI Key

YMFSSKIJSZRDHG-BJVZJOSESA-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
Sargassum autumnale	Chromalveolata	KNApSAcK

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
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Methyl ester
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.69	ALOGPS
logP	7.26	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	9.8	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	139.95 m³·mol⁻¹	ChemAxon
Polarizability	54.55 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162918741

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Nahocol B (NP0079573)

MOL for NP0079573 (Nahocol B)

3D MOL for NP0079573 (Nahocol B)

3D SDF for NP0079573 (Nahocol B)

3D-SDF for NP0079573 (Nahocol B)

PDB for NP0079573 (Nahocol B)

3D PDB for NP0079573 (Nahocol B)

SMILES for NP0079573 (Nahocol B)

INCHI for NP0079573 (Nahocol B)

Structure for NP0079573 (Nahocol B)

3D Structure for NP0079573 (Nahocol B)