NP-MRD: Showing NP-Card for 4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid (NP0149690)

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Record Information

Version

2.0

Created at

2022-09-02 05:37:05 UTC

Updated at

2022-09-02 05:37:05 UTC

NP-MRD ID

NP0149690

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid

Description

4-{[(2R,4aR,8R,8aR)-8-[(3E)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid is found in Leiocarpa semicalva. Based on a literature review very few articles have been published on 4-{[(2R,4aR,8R,8aR)-8-[(3E)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207372D          

 32 33  0  0  1  0            999 V2000
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 31 32  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022207372D          

 32 33  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0149690

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC\C=C(/C)CC[C@@H]1C(C)=CC[C@@H]2C(C)(C)C[C@H](C[C@@]12C)OC(=O)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H40O6/c1-17(13-14-31-19(3)27)7-9-21-18(2)8-10-22-25(4,5)15-20(16-26(21,22)6)32-24(30)12-11-23(28)29/h8,13,20-22H,7,9-12,14-16H2,1-6H3,(H,28,29)/b17-13+/t20-,21-,22-,26+/m1/s1

> <INCHI_KEY>
KCLANEPHRGZKAY-RBIDZOPDSA-N

> <FORMULA>
C26H40O6

> <MOLECULAR_WEIGHT>
448.6

> <EXACT_MASS>
448.282489008

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.74026105682723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[(2R,4aR,8R,8aR)-8-[(3E)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid

> <ALOGPS_LOGP>
5.44

> <JCHEM_LOGP>
4.421771816666667

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.3574952260474005

> <JCHEM_PKA_STRONGEST_BASIC>
-6.7243316473056165

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
123.99209999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2R,4aR,8R,8aR)-8-[(3E)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.324   8.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.344   8.110   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   6.160   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  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+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                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   31                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   31                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   21   31                                                       
CONECT   31   30   11   16   32                                             
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
4-{[(2R,4ar,8R,8ar)-8-[(3E)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-yl]oxy}-4-oxobutanoate	Generator

Chemical Formula

C₂₆H₄₀O₆

Average Mass

448.6000 Da

Monoisotopic Mass

448.28249 Da

IUPAC Name

4-{[(2R,4aR,8R,8aR)-8-[(3E)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid

Traditional Name

4-{[(2R,4aR,8R,8aR)-8-[(3E)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC\C=C(/C)CC[C@@H]1C(C)=CC[C@@H]2C(C)(C)C[C@H](C[C@@]12C)OC(=O)CCC(O)=O

InChI Identifier

InChI=1S/C26H40O6/c1-17(13-14-31-19(3)27)7-9-21-18(2)8-10-22-25(4,5)15-20(16-26(21,22)6)32-24(30)12-11-23(28)29/h8,13,20-22H,7,9-12,14-16H2,1-6H3,(H,28,29)/b17-13+/t20-,21-,22-,26+/m1/s1

InChI Key

KCLANEPHRGZKAY-RBIDZOPDSA-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
Leiocarpa semicalva	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
Labdane diterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.44	ALOGPS
logP	4.42	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	123.99 m³·mol⁻¹	ChemAxon
Polarizability	51.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

163028146

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid (NP0149690)

MOL for NP0149690 (4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid)

3D MOL for NP0149690 (4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid)

3D SDF for NP0149690 (4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid)

3D-SDF for NP0149690 (4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid)

PDB for NP0149690 (4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid)

3D PDB for NP0149690 (4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid)

SMILES for NP0149690 (4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid)

INCHI for NP0149690 (4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid)

Structure for NP0149690 (4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid)

3D Structure for NP0149690 (4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid)