NP-MRD: Showing NP-Card for {5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate (NP0248035)

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Record Information

Version

2.0

Created at

2022-09-07 10:07:21 UTC

Updated at

2022-09-07 10:07:21 UTC

NP-MRD ID

NP0248035

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate

Description

{5,6-Dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate 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. {5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate is found in Euphorbia cotinifolia. {5,6-Dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201501232D          

 35 38  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1533004201501232D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 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
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  0  0  0  0
 16 31  1  0  0  0  0
 10 31  1  0  0  0  0
 31 32  2  0  0  0  0
 12 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248035

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)OCC1=CC2C3C(CC(C)C4(C=C(C)C(OC(=O)C(C)C)C4(O)C1O)C2=O)C3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O7/c1-13(2)24(31)34-12-17-10-18-20-19(26(20,7)8)9-16(6)27(22(18)30)11-15(5)23(28(27,33)21(17)29)35-25(32)14(3)4/h10-11,13-14,16,18-21,23,29,33H,9,12H2,1-8H3

> <INCHI_KEY>
VCJSRQIINLBCDA-UHFFFAOYSA-N

> <FORMULA>
C28H40O7

> <MOLECULAR_WEIGHT>
488.621

> <EXACT_MASS>
488.277403628

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.670346687881434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
3.661963097666667

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.856366032169358

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.126651414456022

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5646605956295074

> <JCHEM_POLAR_SURFACE_AREA>
110.13

> <JCHEM_REFRACTIVITY>
130.73269999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       6.932  12.500   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.168  10.979   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.604  10.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.968  10.013   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.532  10.570   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       6.204   8.491   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.004   7.526   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.240   6.004   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.731   5.518   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.377   4.048   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.610   3.026   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.690   1.488   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.476   0.461   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.938   0.882   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.014  -0.349   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.067   2.305   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.041   1.069   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.549   1.489   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.336   0.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.502   3.029   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.240   3.912   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.155   3.261   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.289   1.727   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.417   4.144   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.812   3.493   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.283   5.678   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.963   3.510   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.719   4.419   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.978   5.097   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.611   5.806   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.208   3.151   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.135   1.922   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.982   2.327   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.288   1.511   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.196   3.275   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   31                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   27   31                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   20   16   28   29                                             
CONECT   28   27                                                            
CONECT   29   27    8   30                                                  
CONECT   30   29                                                            
CONECT   31   16   10   32                                                  
CONECT   32   31                                                            
CONECT   33   12   11   34   35                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
{5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0,.0,]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoic acid	Generator
{5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoic acid	Generator

Chemical Formula

C₂₈H₄₀O₇

Average Mass

488.6210 Da

Monoisotopic Mass

488.27740 Da

IUPAC Name

{5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate

Traditional Name

{5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OCC1=CC2C3C(CC(C)C4(C=C(C)C(OC(=O)C(C)C)C4(O)C1O)C2=O)C3(C)C

InChI Identifier

InChI=1S/C28H40O7/c1-13(2)24(31)34-12-17-10-18-20-19(26(20,7)8)9-16(6)27(22(18)30)11-15(5)23(28(27,33)21(17)29)35-25(32)14(3)4/h10-11,13-14,16,18-21,23,29,33H,9,12H2,1-8H3

InChI Key

VCJSRQIINLBCDA-UHFFFAOYSA-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 cotinifolia	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
Dicarboxylic acid or derivatives
Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
1,2-diol
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	2.8	ALOGPS
logP	3.66	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.13	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	130.73 m³·mol⁻¹	ChemAxon
Polarizability	53.67 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

13559443

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate (NP0248035)

MOL for NP0248035 ({5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate)

3D MOL for NP0248035 ({5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate)

3D SDF for NP0248035 ({5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate)

3D-SDF for NP0248035 ({5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate)

PDB for NP0248035 ({5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate)

3D PDB for NP0248035 ({5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate)

SMILES for NP0248035 ({5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate)

INCHI for NP0248035 ({5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate)

Structure for NP0248035 ({5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate)

3D Structure for NP0248035 ({5,6-dihydroxy-3,11,11,14-tetramethyl-4-[(2-methylpropanoyl)oxy]-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-7-yl}methyl 2-methylpropanoate)