NP-MRD: Showing NP-Card for [(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid (NP0206557)

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Record Information

Version

2.0

Created at

2022-09-05 02:50:35 UTC

Updated at

2022-09-05 02:50:35 UTC

NP-MRD ID

NP0206557

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid

Description

2-[(1S,4S,5R,6R,9S,10R,12R,14R)-4,7-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-6-yl]acetic acid belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. [(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid is found in Euphorbia peplus. Based on a literature review very few articles have been published on 2-[(1S,4S,5R,6R,9S,10R,12R,14R)-4,7-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-6-yl]acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204502D          

 33 36  0  0  1  0            999 V2000
    0.3613   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3190   -1.1719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.4227   -0.9524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052204502D          

 33 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0206557

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H]2[C@H]([C@@H]3C=C(CC(O)=O)[C@@H](CC(O)=O)[C@]4(O)[C@@H](CC(O)=O)C(C)=C[C@@]14C3=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O8/c1-11-10-24-12(2)5-17-21(23(17,3)4)14(22(24)32)6-13(7-18(26)27)16(9-20(30)31)25(24,33)15(11)8-19(28)29/h6,10,12,14-17,21,33H,5,7-9H2,1-4H3,(H,26,27)(H,28,29)(H,30,31)/t12-,14+,15+,16-,17-,21+,24+,25-/m1/s1

> <INCHI_KEY>
PYEOPUBSVAACES-CINZWWHMSA-N

> <FORMULA>
C25H32O8

> <MOLECULAR_WEIGHT>
460.523

> <EXACT_MASS>
460.20971799

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.13227201191979

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,4S,5R,6R,9S,10R,12R,14R)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-7-yl]acetic acid

> <JCHEM_LOGP>
1.5143578296666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.24499347416883

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7067358255017187

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4242251480404864

> <JCHEM_POLAR_SURFACE_AREA>
149.2

> <JCHEM_REFRACTIVITY>
117.57959999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,4S,5R,6R,9S,10R,12R,14R)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-7-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.675  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.858  -1.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.359  -0.910   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.329  -2.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.484  -3.024   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.389  -1.778   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.676  -3.891   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.094  -5.357   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.615  -5.886   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.426  -7.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.655  -8.342   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.073  -7.742   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.466  -9.871   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.304  -5.009   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.964  -5.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.951  -7.307   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.278  -8.088   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.611  -8.066   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.224  -3.400   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.969  -4.293   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.773  -2.816   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.473  -3.642   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.892  -2.929   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.192  -3.755   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.958  -1.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.892  -2.880   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.917  -1.341   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.698  -0.315   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.175  -0.764   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.230   0.452   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.238  -2.132   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.514  -1.269   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.485  -3.035   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19   29                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14    4   20   21                                             
CONECT   20   19                                                            
CONECT   21   19    2   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    7   27   31                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28    4   30                                                  
CONECT   30   29                                                            
CONECT   31   27   26   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
2-[(1S,4S,5R,6R,9S,10R,12R,14R)-4,7-Bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0,.0,]pentadeca-2,7-dien-6-yl]acetate	Generator

Chemical Formula

C₂₅H₃₂O₈

Average Mass

460.5230 Da

Monoisotopic Mass

460.20972 Da

IUPAC Name

2-[(1S,4S,5R,6R,9S,10R,12R,14R)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-7-yl]acetic acid

Traditional Name

[(1S,4S,5R,6R,9S,10R,12R,14R)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-7-yl]acetic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H]2[C@H]([C@@H]3C=C(CC(O)=O)[C@@H](CC(O)=O)[C@]4(O)[C@@H](CC(O)=O)C(C)=C[C@@]14C3=O)C2(C)C

InChI Identifier

InChI=1S/C25H32O8/c1-11-10-24-12(2)5-17-21(23(17,3)4)14(22(24)32)6-13(7-18(26)27)16(9-20(30)31)25(24,33)15(11)8-19(28)29/h6,10,12,14-17,21,33H,5,7-9H2,1-4H3,(H,26,27)(H,28,29)(H,30,31)/t12-,14+,15+,16-,17-,21+,24+,25-/m1/s1

InChI Key

PYEOPUBSVAACES-CINZWWHMSA-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 Euphorbia peplus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Ingenane diterpenoid
Tricarboxylic acid or derivatives
Tertiary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.51	ChemAxon
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	149.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	117.58 m³·mol⁻¹	ChemAxon
Polarizability	47.13 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162817232

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid (NP0206557)

MOL for NP0206557 ([(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid)

3D MOL for NP0206557 ([(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid)

3D SDF for NP0206557 ([(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid)

3D-SDF for NP0206557 ([(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid)

PDB for NP0206557 ([(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid)

3D PDB for NP0206557 ([(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid)

SMILES for NP0206557 ([(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid)

INCHI for NP0206557 ([(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid)

Structure for NP0206557 ([(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid)

3D Structure for NP0206557 ([(1s,4s,5r,6r,9s,10r,12r,14r)-4,6-bis(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl]acetic acid)