NP-MRD: Showing NP-Card for (10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid (NP0212487)

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Record Information

Version

2.0

Created at

2022-09-05 11:10:22 UTC

Updated at

2022-09-05 11:10:22 UTC

NP-MRD ID

NP0212487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid

Description

(10R)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid is found in Sargassum yezoense. Based on a literature review very few articles have been published on (10R)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052213102D          

 32 32  0  0  1  0            999 V2000
    2.8579   11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052213102D          

 32 32  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0212487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(=CCCC(C)=CCC[C@@](C)(O)CCC1=CC(O)=CC(C)=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O5/c1-19(2)9-6-12-22(26(30)31)13-7-10-20(3)11-8-15-27(5,32)16-14-23-18-24(28)17-21(4)25(23)29/h9,11,13,17-18,28-29,32H,6-8,10,12,14-16H2,1-5H3,(H,30,31)/t27-/m1/s1

> <INCHI_KEY>
KDPOESSIVGQJTQ-HHHXNRCGSA-N

> <FORMULA>
C27H40O5

> <MOLECULAR_WEIGHT>
444.612

> <EXACT_MASS>
444.287574388

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.14420331173551

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10R)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid

> <JCHEM_LOGP>
6.791357511666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.066218011388441

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.135537595730066

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7816151268479814

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
133.3379

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(10R)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  21.560   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  20.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  19.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  19.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  17.710   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  15.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  14.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  12.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  10.010   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       0.000   7.700   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      -1.540   6.160   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.540   6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+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       4.001  14.630   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001  13.090   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.335  15.400   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    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   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21   29                                                  
CONECT   29   28                                                            
CONECT   30    7   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

View in JSmol

Synonyms

Value	Source
(10R)-12-(2,5-Dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoate	Generator

Chemical Formula

C₂₇H₄₀O₅

Average Mass

444.6120 Da

Monoisotopic Mass

444.28757 Da

IUPAC Name

(10R)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid

Traditional Name

(10R)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(=CCCC(C)=CCC[C@@](C)(O)CCC1=CC(O)=CC(C)=C1O)C(O)=O

InChI Identifier

InChI=1S/C27H40O5/c1-19(2)9-6-12-22(26(30)31)13-7-10-20(3)11-8-15-27(5,32)16-14-23-18-24(28)17-21(4)25(23)29/h9,11,13,17-18,28-29,32H,6-8,10,12,14-16H2,1-5H3,(H,30,31)/t27-/m1/s1

InChI Key

KDPOESSIVGQJTQ-HHHXNRCGSA-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
Sargassum yezoense	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 acid
Prenylbenzoquinol
O-cresol
M-cresol
Hydroquinone
1-hydroxy-2-unsubstituted benzenoid
Methyl-branched fatty acid
Toluene
Phenol
Hydroxy fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Monocyclic benzene moiety
Tertiary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.79	ChemAxon
pKa (Strongest Acidic)	5.14	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	133.34 m³·mol⁻¹	ChemAxon
Polarizability	52.14 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

162868947

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid (NP0212487)

MOL for NP0212487 ((10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid)

3D MOL for NP0212487 ((10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid)

3D SDF for NP0212487 ((10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid)

3D-SDF for NP0212487 ((10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid)

PDB for NP0212487 ((10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid)

3D PDB for NP0212487 ((10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid)

SMILES for NP0212487 ((10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid)

INCHI for NP0212487 ((10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid)

Structure for NP0212487 ((10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid)

3D Structure for NP0212487 ((10r)-12-(2,5-dihydroxy-3-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6-dienoic acid)