NP-MRD: Showing NP-Card for 2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid (NP0221115)

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Record Information

Version

1.0

Created at

2022-09-05 22:36:17 UTC

Updated at

2022-09-05 22:36:17 UTC

NP-MRD ID

NP0221115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid

Description

2-(5-Hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2,5-dihydrofuran-3-yl)nona-2,6-dienoic acid belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 2-(5-Hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2,5-dihydrofuran-3-yl)nona-2,6-dienoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191518402D          

 25 25  0  0  0  0            999 V2000
    5.5691    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546    8.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    7.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    6.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    6.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    5.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    4.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    5.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    4.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546    6.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546    9.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    9.7768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  4  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 10 20  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END


  Mrv1533004191518402D          

 25 25  0  0  0  0            999 V2000
    5.5691    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546    8.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    7.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    6.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    6.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    5.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    4.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    5.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    4.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546    6.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546    9.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    9.7768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  4  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 10 20  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221115

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CO)=CCCC(=CCCC(C)=CCCC1=CC(=O)OC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O5/c1-15(6-3-9-17-12-19(22)25-14-17)7-4-10-18(20(23)24)11-5-8-16(2)13-21/h6,8,10,12,21H,3-5,7,9,11,13-14H2,1-2H3,(H,23,24)

> <INCHI_KEY>
ADBUIFPZNQVMPU-UHFFFAOYSA-N

> <FORMULA>
C20H28O5

> <MOLECULAR_WEIGHT>
348.439

> <EXACT_MASS>
348.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.03971101389948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2,5-dihydrofuran-3-yl)nona-2,6-dienoic acid

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
3.670041127666667

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.433566064057798

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.0087200487605426

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0797068385663824

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
100.42909999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2H-furan-3-yl)nona-2,6-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      10.396  15.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.062  15.940   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.728  15.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.728  13.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.395  12.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.395  11.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.061  10.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.061   9.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.727   8.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.727   6.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.393   5.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.061   5.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.728  10.550   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.728   9.010   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.062  11.320   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.062  17.480   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.728  18.250   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   14                                                       
CONECT   20   10                                                            
CONECT   21    6   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    2   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
2-(5-Hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2,5-dihydrofuran-3-yl)nona-2,6-dienoate	Generator

Chemical Formula

C₂₀H₂₈O₅

Average Mass

348.4390 Da

Monoisotopic Mass

348.19367 Da

IUPAC Name

2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2,5-dihydrofuran-3-yl)nona-2,6-dienoic acid

Traditional Name

2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2H-furan-3-yl)nona-2,6-dienoic acid

CAS Registry Number

Not Available

SMILES

CC(CO)=CCCC(=CCCC(C)=CCCC1=CC(=O)OC1)C(O)=O

InChI Identifier

InChI=1S/C20H28O5/c1-15(6-3-9-17-12-19(22)25-14-17)7-4-10-18(20(23)24)11-5-8-16(2)13-21/h6,8,10,12,21H,3-5,7,9,11,13-14H2,1-2H3,(H,23,24)

InChI Key

ADBUIFPZNQVMPU-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 diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Medium-chain hydroxy acid
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
2-furanone
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Unsaturated fatty acid
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Primary alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	3.52	ALOGPS
logP	3.67	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5.01	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	100.43 m³·mol⁻¹	ChemAxon
Polarizability	39.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid (NP0221115)

MOL for NP0221115 (2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid)

3D MOL for NP0221115 (2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid)

3D SDF for NP0221115 (2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid)

3D-SDF for NP0221115 (2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid)

PDB for NP0221115 (2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid)

3D PDB for NP0221115 (2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid)

SMILES for NP0221115 (2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid)

INCHI for NP0221115 (2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid)

Structure for NP0221115 (2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid)

3D Structure for NP0221115 (2-(5-hydroxy-4-methylpent-3-en-1-yl)-6-methyl-9-(5-oxo-2h-furan-3-yl)nona-2,6-dienoic acid)