NP-MRD: Showing NP-Card for (1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate (NP0261536)

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Record Information

Version

2.0

Created at

2022-09-08 04:00:31 UTC

Updated at

2022-09-08 04:00:31 UTC

NP-MRD ID

NP0261536

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate

Description

Euphoractine E belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. (1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate is found in Euphorbia micractina. Based on a literature review very few articles have been published on Euphoractine E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082206002D          

 34 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082206002D          

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  4 30  1  0  0  0  0
 30 31  2  0  0  0  0
 15 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261536

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC2=C([C@H]1O)[C@@H](O)[C@]1(C)CC[C@H]3[C@@H]([C@@H](OC(=O)\C=C\C4=CC=CC=C4)[C@]1(C)C2=O)C3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O5/c1-16-15-18-21(23(16)31)25(33)28(4)14-13-19-22(27(19,2)3)26(29(28,5)24(18)32)34-20(30)12-11-17-9-7-6-8-10-17/h6-12,16,19,22-23,25-26,31,33H,13-15H2,1-5H3/b12-11+/t16-,19-,22-,23-,25+,26+,28-,29-/m0/s1

> <INCHI_KEY>
HKPWYRCJCZALNK-RWZDKYSZSA-N

> <FORMULA>
C29H36O5

> <MOLECULAR_WEIGHT>
464.602

> <EXACT_MASS>
464.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.1933018475691

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4S,5S,9R,10R,11R,13S)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0^{3,7}.0^{11,13}]pentadec-3(7)-en-10-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
4.854920541333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.509203830343676

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.786975141907984

> <JCHEM_PKA_STRONGEST_BASIC>
-3.13853589245414

> <JCHEM_POLAR_SURFACE_AREA>
83.82999999999998

> <JCHEM_REFRACTIVITY>
130.95109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,5S,9R,10R,11R,13S)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0^{3,7}.0^{11,13}]pentadec-3(7)-en-10-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.044  -4.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.484  -4.583   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.535  -5.709   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.930  -5.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.741  -3.528   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.229  -3.236   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.577  -1.841   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.970  -2.600   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.781  -1.072   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.389  -3.201   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.086  -1.691   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.466  -2.100   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.998  -2.256   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.831  -3.551   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.338  -5.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.890  -5.534   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.735  -7.066   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.984  -7.967   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.388  -7.336   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.828  -9.499   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.077 -10.400   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.921 -11.932   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.170 -12.833   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.014 -14.365   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.609 -14.997   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.361 -14.096   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.516 -12.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.578  -4.729   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.652  -6.267   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.349  -5.657   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.538  -7.185   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.848  -4.707   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.761  -5.948   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.326  -4.274   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   28                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   16   10   29   30                                             
CONECT   29   28                                                            
CONECT   30   28    4   31                                                  
CONECT   31   30                                                            
CONECT   32   15   14   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₅

Average Mass

464.6020 Da

Monoisotopic Mass

464.25627 Da

IUPAC Name

(1R,2S,4S,5S,9R,10R,11R,13S)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0^{3,7}.0^{11,13}]pentadec-3(7)-en-10-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(1R,2S,4S,5S,9R,10R,11R,13S)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0^{3,7}.0^{11,13}]pentadec-3(7)-en-10-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

C[C@H]1CC2=C([C@H]1O)[C@@H](O)[C@]1(C)CC[C@H]3[C@@H]([C@@H](OC(=O)\C=C\C4=CC=CC=C4)[C@]1(C)C2=O)C3(C)C

InChI Identifier

InChI=1S/C29H36O5/c1-16-15-18-21(23(16)31)25(33)28(4)14-13-19-22(27(19,2)3)26(29(28,5)24(18)32)34-20(30)12-11-17-9-7-6-8-10-17/h6-12,16,19,22-23,25-26,31,33H,13-15H2,1-5H3/b12-11+/t16-,19-,22-,23-,25+,26+,28-,29-/m0/s1

InChI Key

HKPWYRCJCZALNK-RWZDKYSZSA-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
Euphorbia micractina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Styrene
Cyclohexenone
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	4.85	ChemAxon
pKa (Strongest Acidic)	13.79	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	130.95 m³·mol⁻¹	ChemAxon
Polarizability	51.19 Å³	ChemAxon
Number of Rings	5	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

101918982

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate (NP0261536)

MOL for NP0261536 ((1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0261536 ((1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0261536 ((1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0261536 ((1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0261536 ((1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0261536 ((1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0261536 ((1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0261536 ((1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0261536 ((1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0261536 ((1r,2s,4s,5s,9r,10r,11r,13s)-2,4-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadec-3(7)-en-10-yl (2e)-3-phenylprop-2-enoate)