NP-MRD: Showing NP-Card for 5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid (NP0330523)

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Record Information

Version

1.0

Created at

2022-09-12 15:57:31 UTC

Updated at

2022-09-12 15:57:31 UTC

NP-MRD ID

NP0330523

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid

Description

5-(5-Formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl)-3-methylpentanoic acid belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. 5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid is found in Olearia teretifolia. 5-(5-Formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl)-3-methylpentanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251508082D          

 30 31  0  0  0  0            999 V2000
   -0.0980   -1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414   -0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7111    0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9933    1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8057    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3360    0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6182    1.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879    2.1825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701    2.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1825    3.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8398    3.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0273    3.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7451    2.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842   -0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3966   -0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788    0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4307    1.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9004    2.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 27  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004251508082D          

 30 31  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0330523

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1(C)C(C)CCC2(COC(=O)C=C(C)C)C1CCC=C2C=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O5/c1-17(2)13-23(29)30-16-25-12-10-19(4)24(5,11-9-18(3)14-22(27)28)21(25)8-6-7-20(25)15-26/h7,13,15,18-19,21H,6,8-12,14,16H2,1-5H3,(H,27,28)

> <INCHI_KEY>
QCBBYPFNMFFJJJ-UHFFFAOYSA-N

> <FORMULA>
C25H38O5

> <MOLECULAR_WEIGHT>
418.574

> <EXACT_MASS>
418.271924324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.7443361787162

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl)-3-methylpentanoic acid

> <ALOGPS_LOGP>
5.00

> <JCHEM_LOGP>
5.280538856

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.781131241341657

> <JCHEM_PKA_STRONGEST_BASIC>
-4.745644119965346

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
118.48819999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.50e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -0.183  -2.577   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.183  -1.037   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.517  -0.267   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.850  -1.037   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.184  -0.267   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.711  -1.715   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.194   0.912   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.677   0.645   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.721   2.359   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.237   2.627   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.227   1.447   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.754   2.894   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.764   4.074   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.291   5.521   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -7.807   5.789   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.301   6.701   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.784   6.433   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.794   7.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.258   4.986   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.701   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.690  -1.180   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.207  -0.912   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.734   0.535   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.744   1.715   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.271   3.162   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -7.281   4.341   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.151  -0.267   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.484  -1.037   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.818  -0.267   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.484  -2.577   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   20                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20   24                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   11    5   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   11   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
5-(5-Formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl)-3-methylpentanoate	Generator

Chemical Formula

C₂₅H₃₈O₅

Average Mass

418.5740 Da

Monoisotopic Mass

418.27192 Da

IUPAC Name

5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl)-3-methylpentanoic acid

Traditional Name

5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC1(C)C(C)CCC2(COC(=O)C=C(C)C)C1CCC=C2C=O)CC(O)=O

InChI Identifier

InChI=1S/C25H38O5/c1-17(2)13-23(29)30-16-25-12-10-19(4)24(5,11-9-18(3)14-22(27)28)21(25)8-6-7-20(25)15-26/h7,13,15,18-19,21H,6,8-12,14,16H2,1-5H3,(H,27,28)

InChI Key

QCBBYPFNMFFJJJ-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

Species Name	Source	Reference
Olearia teretifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Carbocyclic fatty acid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Aldehyde
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	ALOGPS
logP	5.28	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.78	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	118.49 m³·mol⁻¹	ChemAxon
Polarizability	47.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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 5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid (NP0330523)

MOL for NP0330523 (5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid)

3D MOL for NP0330523 (5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid)

3D SDF for NP0330523 (5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid)

3D-SDF for NP0330523 (5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid)

PDB for NP0330523 (5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid)

3D PDB for NP0330523 (5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid)

SMILES for NP0330523 (5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid)

INCHI for NP0330523 (5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid)

Structure for NP0330523 (5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid)

3D Structure for NP0330523 (5-(5-formyl-1,2-dimethyl-4a-{[(3-methylbut-2-enoyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl)-3-methylpentanoic acid)