NP-MRD: Showing NP-Card for Gutierrezianolic acid 3-phenylpropionate methyl ester (NP0065507)

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Record Information

Version

2.0

Created at

2022-04-28 09:43:36 UTC

Updated at

2022-04-28 09:43:36 UTC

NP-MRD ID

NP0065507

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gutierrezianolic acid 3-phenylpropionate methyl ester

Description

Methyl (1R,4R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5,5,8a-trimethyl-4-[(3-phenylpropanoyl)oxy]-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate 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. Gutierrezianolic acid 3-phenylpropionate methyl ester is found in Gutierrezia espinosae. Based on a literature review very few articles have been published on methyl (1R,4R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5,5,8a-trimethyl-4-[(3-phenylpropanoyl)oxy]-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282211432D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282211432D          

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  8 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 28 32  1  0  0  0  0
  5 33  1  1  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0065507

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C[C@@H](OC(=O)CCC2=CC=CC=C2)[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1CCC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O5/c1-29(2)16-8-17-30(3)24(13-11-22-15-18-34-20-22)23(28(32)33-4)19-25(27(29)30)35-26(31)14-12-21-9-6-5-7-10-21/h5-7,9-10,15,18-20,24-25,27H,8,11-14,16-17H2,1-4H3/t24-,25+,27-,30+/m0/s1

> <INCHI_KEY>
PRZOSNLUCGBIOL-WLZBTTNTSA-N

> <FORMULA>
C30H38O5

> <MOLECULAR_WEIGHT>
478.629

> <EXACT_MASS>
478.271924324

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.80289414849507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,4R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5,5,8a-trimethyl-4-[(3-phenylpropanoyl)oxy]-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate

> <ALOGPS_LOGP>
6.78

> <JCHEM_LOGP>
7.023717027000001

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.784145167377313

> <JCHEM_POLAR_SURFACE_AREA>
65.74000000000001

> <JCHEM_REFRACTIVITY>
135.75860000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5,5,8a-trimethyl-4-[(3-phenylpropanoyl)oxy]-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.088   4.755   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.564   6.220   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.104   6.220   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.580   4.755   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.723  -4.440   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.723  -4.440   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   34   35                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   33                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   26                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   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   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22    8   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26    7   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   28                                                       
CONECT   33    5                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,4R,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5,5,8a-trimethyl-4-[(3-phenylpropanoyl)oxy]-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid	Generator

Chemical Formula

C₃₀H₃₈O₅

Average Mass

478.6290 Da

Monoisotopic Mass

478.27192 Da

IUPAC Name

methyl (1R,4R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5,5,8a-trimethyl-4-[(3-phenylpropanoyl)oxy]-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate

Traditional Name

methyl (1R,4R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5,5,8a-trimethyl-4-[(3-phenylpropanoyl)oxy]-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C[C@@H](OC(=O)CCC2=CC=CC=C2)[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1CCC1=COC=C1

InChI Identifier

InChI=1S/C30H38O5/c1-29(2)16-8-17-30(3)24(13-11-22-15-18-34-20-22)23(28(32)33-4)19-25(27(29)30)35-26(31)14-12-21-9-6-5-7-10-21/h5-7,9-10,15,18-20,24-25,27H,8,11-14,16-17H2,1-4H3/t24-,25+,27-,30+/m0/s1

InChI Key

PRZOSNLUCGBIOL-WLZBTTNTSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Gutierrezia espinosae	Plant	KNApSAcK

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
Fatty acid ester
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Furan
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	6.78	ALOGPS
logP	7.02	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.74 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	135.76 m³·mol⁻¹	ChemAxon
Polarizability	53.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162921879

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gutierrezianolic acid 3-phenylpropionate methyl ester (NP0065507)

MOL for NP0065507 (Gutierrezianolic acid 3-phenylpropionate methyl ester)

3D MOL for NP0065507 (Gutierrezianolic acid 3-phenylpropionate methyl ester)

3D SDF for NP0065507 (Gutierrezianolic acid 3-phenylpropionate methyl ester)

3D-SDF for NP0065507 (Gutierrezianolic acid 3-phenylpropionate methyl ester)

PDB for NP0065507 (Gutierrezianolic acid 3-phenylpropionate methyl ester)

3D PDB for NP0065507 (Gutierrezianolic acid 3-phenylpropionate methyl ester)

SMILES for NP0065507 (Gutierrezianolic acid 3-phenylpropionate methyl ester)

INCHI for NP0065507 (Gutierrezianolic acid 3-phenylpropionate methyl ester)

Structure for NP0065507 (Gutierrezianolic acid 3-phenylpropionate methyl ester)

3D Structure for NP0065507 (Gutierrezianolic acid 3-phenylpropionate methyl ester)