NP-MRD: Showing NP-Card for 1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate (NP0285877)

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Record Information

Version

2.0

Created at

2022-09-09 14:14:03 UTC

Updated at

2022-09-09 14:14:04 UTC

NP-MRD ID

NP0285877

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate

Description

1-(2E)-5-[(4aR,5S,7R,8aS)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate is found in Acamptopappus sphaerocephalus. Based on a literature review very few articles have been published on 1-(2E)-5-[(4aR,5S,7R,8aS)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092216142D          

 35 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309092216142D          

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  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 16 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0285877

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCC(=O)OC\C=C(/C)CCC1=C(C)C(=O)C[C@H]2[C@@](C)(COC(C)=O)C[C@H](O)C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O8/c1-17(11-12-34-25(32)10-9-24(31)33-6)7-8-21-18(2)22(30)13-23-26(4,16-35-19(3)28)14-20(29)15-27(21,23)5/h11,20,23,29H,7-10,12-16H2,1-6H3/b17-11+/t20-,23-,26+,27+/m0/s1

> <INCHI_KEY>
IVHFQEQXKTWOIU-DFNXUMBPSA-N

> <FORMULA>
C27H40O8

> <MOLECULAR_WEIGHT>
492.609

> <EXACT_MASS>
492.272318248

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.63787332318165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2E)-5-[(4aR,5S,7R,8aS)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate

> <JCHEM_LOGP>
2.5759535299999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.15018171578955

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.210623250507112

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7066471132008507

> <JCHEM_POLAR_SURFACE_AREA>
116.20000000000003

> <JCHEM_REFRACTIVITY>
130.96249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-(2E)-5-[(4aR,5S,7R,8aS)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      17.338   0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      18.672   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      20.005   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      20.005   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      21.339   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.673   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.006   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      24.006  -1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      25.340   0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      26.674   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.007   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.341   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.341  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.675   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.008   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.342   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.342   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.008   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.676   3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      34.676   4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      36.009   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.009   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.343   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      37.870   1.447   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      38.860  -0.267   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      39.850   0.912   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      41.366   0.645   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      42.356   1.825   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      41.893  -0.802   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      37.343  -1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      36.009  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      36.009  -3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      34.676  -1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      34.676   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      33.342  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    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                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24   25   30                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   23   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   16   22   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
1-(2E)-5-[(4AR,5S,7R,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioic acid	Generator

Chemical Formula

C₂₇H₄₀O₈

Average Mass

492.6090 Da

Monoisotopic Mass

492.27232 Da

IUPAC Name

1-(2E)-5-[(4aR,5S,7R,8aS)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate

Traditional Name

1-(2E)-5-[(4aR,5S,7R,8aS)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate

CAS Registry Number

Not Available

SMILES

COC(=O)CCC(=O)OC\C=C(/C)CCC1=C(C)C(=O)C[C@H]2[C@@](C)(COC(C)=O)C[C@H](O)C[C@]12C

InChI Identifier

InChI=1S/C27H40O8/c1-17(11-12-34-25(32)10-9-24(31)33-6)7-8-21-18(2)22(30)13-23-26(4,16-35-19(3)28)14-20(29)15-27(21,23)5/h11,20,23,29H,7-10,12-16H2,1-6H3/b17-11+/t20-,23-,26+,27+/m0/s1

InChI Key

IVHFQEQXKTWOIU-DFNXUMBPSA-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
Acamptopappus sphaerocephalus	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

Labdane diterpenoid
Diterpenoid
Tricarboxylic acid or derivatives
Cyclohexenone
Fatty acid ester
Fatty acid methyl ester
Fatty acyl
Cyclic alcohol
Methyl ester
Carboxylic acid ester
Cyclic ketone
Ketone
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	2.58	ChemAxon
pKa (Strongest Acidic)	15.21	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.2 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	130.96 m³·mol⁻¹	ChemAxon
Polarizability	54.64 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

14109685

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate (NP0285877)

MOL for NP0285877 (1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate)

3D MOL for NP0285877 (1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate)

3D SDF for NP0285877 (1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate)

3D-SDF for NP0285877 (1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate)

PDB for NP0285877 (1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate)

3D PDB for NP0285877 (1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate)

SMILES for NP0285877 (1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate)

INCHI for NP0285877 (1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate)

Structure for NP0285877 (1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate)

3D Structure for NP0285877 (1-(2e)-5-[(4ar,5s,7r,8as)-5-[(acetyloxy)methyl]-7-hydroxy-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4h-naphthalen-1-yl]-3-methylpent-2-en-1-yl 4-methyl butanedioate)