NP-MRD: Showing NP-Card for (1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate (NP0251103)

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Record Information

Version

2.0

Created at

2022-09-07 14:11:39 UTC

Updated at

2022-09-07 14:11:39 UTC

NP-MRD ID

NP0251103

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate

Description

CHEMBL518541 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate is found in Euphorbia lathyris. Based on a literature review very few articles have been published on CHEMBL518541.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072216112D          

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M  END

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M  END


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 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 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
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 31 30  1  1  0  0  0
  9 31  1  0  0  0  0
 13 31  1  0  0  0  0
 24 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251103

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)O[C@H]1[C@@H](C)C[C@@]2(OC(C)=O)[C@H]1\C=C(CO)\CC[C@H]1[C@@H](\C=C(C)\C2=O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O6/c1-7-8-9-10-24(31)33-25-18(3)15-28(34-19(4)30)23(25)14-20(16-29)11-12-21-22(27(21,5)6)13-17(2)26(28)32/h13-14,18,21-23,25,29H,7-12,15-16H2,1-6H3/b17-13+,20-14-/t18-,21-,22+,23-,25-,28+/m0/s1

> <INCHI_KEY>
QWEBGLOUXCMOMA-WDXCJRAPSA-N

> <FORMULA>
C28H42O6

> <MOLECULAR_WEIGHT>
474.638

> <EXACT_MASS>
474.298139072

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.98642513971908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3E,5R,7S,10Z,12S,13S,14S)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0^{5,7}]pentadeca-3,10-dien-13-yl hexanoate

> <JCHEM_LOGP>
4.879662841333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.881697781957907

> <JCHEM_PKA_STRONGEST_BASIC>
-1.975636081119418

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
131.76789999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3E,5R,7S,10Z,12S,13S,14S)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0^{5,7}]pentadeca-3,10-dien-13-yl hexanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.486  10.179   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.848  10.949   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.182  10.179   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.515  10.949   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.849  10.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.183  10.949   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.183  12.489   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.516  10.179   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.850  10.949   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.011  12.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.867  13.511   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.517  12.801   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.287  11.467   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.193  12.713   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.566  14.120   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.035  14.281   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.471  15.366   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.794  11.147   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.824  12.291   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.270   9.682   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.239   8.538   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.776   9.362   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.252   7.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.221   6.753   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.559   7.031   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.226   6.261   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.081   7.292   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.575   6.972   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.544   8.116   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.708   8.699   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.257  10.323   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.728   6.433   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.074   4.932   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.256   6.245   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   31                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18   31                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31                                                       
CONECT   31   30    9   13                                                  
CONECT   32   24   23   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₆

Average Mass

474.6380 Da

Monoisotopic Mass

474.29814 Da

IUPAC Name

(1R,3E,5R,7S,10Z,12S,13S,14S)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0^{5,7}]pentadeca-3,10-dien-13-yl hexanoate

Traditional Name

(1R,3E,5R,7S,10Z,12S,13S,14S)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0^{5,7}]pentadeca-3,10-dien-13-yl hexanoate

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)O[C@H]1[C@@H](C)C[C@@]2(OC(C)=O)[C@H]1\C=C(CO)\CC[C@H]1[C@@H](\C=C(C)\C2=O)C1(C)C

InChI Identifier

InChI=1S/C28H42O6/c1-7-8-9-10-24(31)33-25-18(3)15-28(34-19(4)30)23(25)14-20(16-29)11-12-21-22(27(21,5)6)13-17(2)26(28)32/h13-14,18,21-23,25,29H,7-12,15-16H2,1-6H3/b17-13+,20-14-/t18-,21-,22+,23-,25-,28+/m0/s1

InChI Key

QWEBGLOUXCMOMA-WDXCJRAPSA-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 lathyris	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

Diterpenoid
Lathyrane diterpenoid
Fatty acid ester
Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Fatty acyl
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	4.88	ChemAxon
pKa (Strongest Acidic)	16.88	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	131.77 m³·mol⁻¹	ChemAxon
Polarizability	52.99 Å³	ChemAxon
Number of Rings	3	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

C00053097

Chemspider ID

9929374

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11754671

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate (NP0251103)

MOL for NP0251103 ((1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate)

3D MOL for NP0251103 ((1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate)

3D SDF for NP0251103 ((1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate)

3D-SDF for NP0251103 ((1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate)

PDB for NP0251103 ((1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate)

3D PDB for NP0251103 ((1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate)

SMILES for NP0251103 ((1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate)

INCHI for NP0251103 ((1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate)

Structure for NP0251103 ((1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate)

3D Structure for NP0251103 ((1r,3e,5r,7s,10z,12s,13s,14s)-1-(acetyloxy)-10-(hydroxymethyl)-3,6,6,14-tetramethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-13-yl hexanoate)