NP-MRD: Showing NP-Card for 3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid (NP0163505)

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Record Information

Version

2.0

Created at

2022-09-02 22:09:55 UTC

Updated at

2022-09-02 22:09:55 UTC

NP-MRD ID

NP0163505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid

Description

3-[11-Carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 3-[11-Carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241512422D          

 34 34  0  0  0  0            999 V2000
    0.7145   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5724   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 29 31  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END

     RDKit          3D

 70 70  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004241512422D          

 34 34  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0163505

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O7/c1-17(2)23(28)14-13-20(26(31)32)10-6-9-18(3)7-5-8-19(4)11-12-21-15-22(27(33)34)16-24(29)25(21)30/h7,10-11,15-16,23,28-30H,1,5-6,8-9,12-14H2,2-4H3,(H,31,32)(H,33,34)

> <INCHI_KEY>
ORYKFAZUHJGRGA-UHFFFAOYSA-N

> <FORMULA>
C27H36O7

> <MOLECULAR_WEIGHT>
472.578

> <EXACT_MASS>
472.246103499

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.27463533034738

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
5.750223107333333

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.06430232130683

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.074701766269655

> <JCHEM_PKA_STRONGEST_BASIC>
-1.412043032622027

> <JCHEM_POLAR_SURFACE_AREA>
135.29

> <JCHEM_REFRACTIVITY>
135.0868

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.68e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.334 -17.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000 -15.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667 -15.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001 -16.170   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      -6.668 -16.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002 -15.400   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -10.669 -15.400   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.336 -13.090   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.668 -13.090   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0     -12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -13.337 -15.400   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0     -12.003 -17.710   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.001 -17.710   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667 -15.400   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335 -15.400   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002 -15.400   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669 -15.400   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.669 -13.860   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337 -15.400   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.003 -17.710   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668 -17.710   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.002 -18.480   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.335 -18.480   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16                                                  
CONECT   16   15                                                            
CONECT   17   11   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    6                                                            
CONECT   21    2   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   24   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Value	Source
3-[11-Carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoate	Generator

Chemical Formula

C₂₇H₃₆O₇

Average Mass

472.5780 Da

Monoisotopic Mass

472.24610 Da

IUPAC Name

3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid

Traditional Name

3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

CC(=C)C(O)CCC(=CCCC(C)=CCCC(C)=CCC1=CC(=CC(O)=C1O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C27H36O7/c1-17(2)23(28)14-13-20(26(31)32)10-6-9-18(3)7-5-8-19(4)11-12-21-15-22(27(33)34)16-24(29)25(21)30/h7,10-11,15-16,23,28-30H,1,5-6,8-9,12-14H2,2-4H3,(H,31,32)(H,33,34)

InChI Key

ORYKFAZUHJGRGA-UHFFFAOYSA-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
Dihydroxybenzoic acid
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Branched fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Phenol
Monocyclic benzene moiety
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
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	4.22	ALOGPS
logP	5.75	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	135.29 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	135.09 m³·mol⁻¹	ChemAxon
Polarizability	52.27 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

74836314

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid (NP0163505)

MOL for NP0163505 (3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid)

3D MOL for NP0163505 (3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid)

3D SDF for NP0163505 (3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid)

3D-SDF for NP0163505 (3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid)

PDB for NP0163505 (3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid)

3D PDB for NP0163505 (3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid)

SMILES for NP0163505 (3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid)

INCHI for NP0163505 (3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid)

Structure for NP0163505 (3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid)

3D Structure for NP0163505 (3-[11-carboxy-11-(3-hydroxy-4-methylpent-4-en-1-yl)-3,7-dimethylundeca-2,6,10-trien-1-yl]-4,5-dihydroxybenzoic acid)