NP-MRD: Showing NP-Card for (2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid (NP0281916)

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Record Information

Version

2.0

Created at

2022-09-09 08:32:14 UTC

Updated at

2022-09-09 08:32:15 UTC

NP-MRD ID

NP0281916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid

Description

(2Z,6E,10S,11Z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review very few articles have been published on (2Z,6E,10S,11Z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092210322D          

 32 32  0  0  1  0            999 V2000
    9.9809    7.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9809    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7434    6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5059    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7309    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   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    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0934    3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    4.2059    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  0  0  0  0
  2  4  2  0  0  0  0
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 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
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 22 23  1  0  0  0  0
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 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
M  END

     RDKit          3D

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   -4.5671   -1.1499    0.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.3670   -0.2947   -2.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309092210322D          

 32 32  0  0  1  0            999 V2000
    9.9809    7.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9809    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0281916

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(=C\CC\C(C)=C\CC[C@](C)(O)\C=C/C1=CC(O)=C(C)C=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O5/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)21(4)17-25(23)29/h9,11,13-14,16-18,28-29,32H,6-8,10,12,15H2,1-5H3,(H,30,31)/b16-14-,20-11+,22-13-/t27-/m0/s1

> <INCHI_KEY>
CSICLPIRUBSEIB-YXZPTPOVSA-N

> <FORMULA>
C27H38O5

> <MOLECULAR_WEIGHT>
442.596

> <EXACT_MASS>
442.271924324

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.34454744504221

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,6E,10S,11Z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid

> <JCHEM_LOGP>
6.6680433149999985

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.749683857647335

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.135532130726471

> <JCHEM_PKA_STRONGEST_BASIC>
-2.947734831395114

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
134.3005

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,6E,10S,11Z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid

> <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      18.631  13.186   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.861  11.852   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.631  10.518   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.321  11.852   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.551  10.518   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.011  10.518   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.241   9.185   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.701   9.185   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.931   7.851   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.391   7.851   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.621   6.517   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.391   5.184   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081   6.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.311   5.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.771   5.184   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.231   2.516   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   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      14.011   7.851   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.241   6.517   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      15.551   7.851   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   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   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
(2Z,6E,10S,11Z)-12-(2,5-Dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoate	Generator

Chemical Formula

C₂₇H₃₈O₅

Average Mass

442.5960 Da

Monoisotopic Mass

442.27192 Da

IUPAC Name

(2Z,6E,10S,11Z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid

Traditional Name

(2Z,6E,10S,11Z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(=C\CC\C(C)=C\CC[C@](C)(O)\C=C/C1=CC(O)=C(C)C=C1O)C(O)=O

InChI Identifier

InChI=1S/C27H38O5/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)21(4)17-25(23)29/h9,11,13-14,16-18,28-29,32H,6-8,10,12,15H2,1-5H3,(H,30,31)/b16-14-,20-11+,22-13-/t27-/m0/s1

InChI Key

CSICLPIRUBSEIB-YXZPTPOVSA-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

Not Available

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
Cinnamyl alcohol
Hydroquinone
M-cresol
O-cresol
Styrene
Toluene
Branched fatty acid
Phenol
Methyl-branched fatty acid
1-hydroxy-2-unsubstituted benzenoid
Hydroxy fatty acid
Unsaturated fatty acid
Fatty acyl
Monocyclic benzene moiety
Fatty acid
Benzenoid
Tertiary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
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	6.67	ChemAxon
pKa (Strongest Acidic)	5.14	ChemAxon
pKa (Strongest Basic)	-2.9	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	12	ChemAxon
Refractivity	134.3 m³·mol⁻¹	ChemAxon
Polarizability	51.34 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

163187459

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid (NP0281916)

MOL for NP0281916 ((2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid)

3D MOL for NP0281916 ((2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid)

3D SDF for NP0281916 ((2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid)

3D-SDF for NP0281916 ((2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid)

PDB for NP0281916 ((2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid)

3D PDB for NP0281916 ((2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid)

SMILES for NP0281916 ((2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid)

INCHI for NP0281916 ((2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid)

Structure for NP0281916 ((2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid)

3D Structure for NP0281916 ((2z,6e,10s,11z)-12-(2,5-dihydroxy-4-methylphenyl)-10-hydroxy-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,11-trienoic acid)