NP-MRD: Showing NP-Card for 2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione (NP0187343)

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Record Information

Version

2.0

Created at

2022-09-04 03:29:17 UTC

Updated at

2022-09-04 03:29:17 UTC

NP-MRD ID

NP0187343

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

Description

2-[(2E,6E,10S,11R)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione is found in Cystoseira brachycarpa. Based on a literature review very few articles have been published on 2-[(2E,6E,10S,11R)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042205292D          

 31 31  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
   -2.8579   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   10.3125    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
   -2.8579    9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    8.2500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6829    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 O   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
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   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    2.0625    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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 30 31  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309042205292D          

 31 31  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0187343

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O4/c1-19(2)9-8-16-27(6,31)25(29)15-13-21(4)11-7-10-20(3)12-14-23-18-24(28)17-22(5)26(23)30/h9,11-12,17-18,25,29,31H,7-8,10,13-16H2,1-6H3/b20-12+,21-11+/t25-,27+/m0/s1

> <INCHI_KEY>
MIUFIRHWLINGPK-ACRDSSFZSA-N

> <FORMULA>
C27H40O4

> <MOLECULAR_WEIGHT>
428.613

> <EXACT_MASS>
428.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.91603769429476

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2E,6E,10S,11R)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

> <JCHEM_LOGP>
5.9470181443333345

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.137220922252421

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.72698262590416

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2115662024038896

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
132.623

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E,6E,10S,11R)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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      -4.001  19.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  19.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  17.710   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  15.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.875  15.400   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.795  15.400   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.668  13.090   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+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   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.334   2.310   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    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   23   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

C₂₇H₄₀O₄

Average Mass

428.6130 Da

Monoisotopic Mass

428.29266 Da

IUPAC Name

2-[(2E,6E,10S,11R)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

Traditional Name

2-[(2E,6E,10S,11R)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H40O4/c1-19(2)9-8-16-27(6,31)25(29)15-13-21(4)11-7-10-20(3)12-14-23-18-24(28)17-22(5)26(23)30/h9,11-12,17-18,25,29,31H,7-8,10,13-16H2,1-6H3/b20-12+,21-11+/t25-,27+/m0/s1

InChI Key

MIUFIRHWLINGPK-ACRDSSFZSA-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
Cystoseira brachycarpa	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
Prenylbenzoquinone
Fatty alcohol
Quinone
P-benzoquinone
Fatty acyl
Tertiary alcohol
Cyclic ketone
Secondary alcohol
1,2-diol
Ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic 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	5.95	ChemAxon
pKa (Strongest Acidic)	13.73	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	132.62 m³·mol⁻¹	ChemAxon
Polarizability	51.92 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

162958655

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione (NP0187343)

MOL for NP0187343 (2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione)

3D MOL for NP0187343 (2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione)

3D SDF for NP0187343 (2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione)

3D-SDF for NP0187343 (2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione)

PDB for NP0187343 (2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione)

3D PDB for NP0187343 (2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione)

SMILES for NP0187343 (2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione)

INCHI for NP0187343 (2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione)

Structure for NP0187343 (2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione)

3D Structure for NP0187343 (2-[(2e,6e,10s,11r)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione)