NP-MRD: Showing NP-Card for (1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0213853)

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Record Information

Version

2.0

Created at

2022-09-05 12:57:52 UTC

Updated at

2022-09-05 12:57:52 UTC

NP-MRD ID

NP0213853

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate

Description

(1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate is found in Euphorbia helioscopia.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052214572D          

 36 38  0  0  1  0            999 V2000
    5.7278    3.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5143    2.2786    0.0000 C   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


  Mrv1652309052214572D          

 36 38  0  0  1  0            999 V2000
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 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 23 33  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  2  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213853

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H38O7/c1-17-12-13-28(5,6)24(31)15-23(35-20(4)30)18(2)14-22-25(19(3)16-29(22,34)26(17)32)36-27(33)21-10-8-7-9-11-21/h7-14,17,19,22-23,25-26,32,34H,15-16H2,1-6H3/b13-12+,18-14+/t17-,19-,22+,23-,25+,26-,29-/m1/s1

> <INCHI_KEY>
MDYKLCGYAGWJNL-UCOYIGIGSA-N

> <FORMULA>
C29H38O7

> <MOLECULAR_WEIGHT>
498.616

> <EXACT_MASS>
498.261753564

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.0372615887635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3aR,4R,5R,11R,13aS)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

> <JCHEM_LOGP>
4.263154151000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.683681650477336

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.270870752055039

> <JCHEM_PKA_STRONGEST_BASIC>
-3.358484135363712

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
137.15560000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3aR,4R,5R,11R,13aS)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1H,2H,3H,4H,5H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

> <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      10.692   5.741   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.293   4.253   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.806   3.855   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.382   3.164   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.984   1.677   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.317   0.907   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.087  -0.427   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.575  -0.028   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.087  -1.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.604  -1.699   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.614  -3.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.754  -2.737   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.984  -4.070   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.444  -4.070   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.045  -5.558   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.110  -3.300   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.021  -4.389   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.340  -1.967   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.788  -3.404   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.875  -2.443   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.970  -1.197   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.430  -1.197   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.875   0.049   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.399   1.514   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.893   1.834   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.863   0.690   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.417   3.299   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.911   3.619   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.435   5.083   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.465   6.228   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.972   5.908   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.448   4.443   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.340  -0.427   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.674   0.343   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.444   1.677   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.674   3.011   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   33                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   33                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   23   18   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34    5   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₈O₇

Average Mass

498.6160 Da

Monoisotopic Mass

498.26175 Da

IUPAC Name

(1S,2R,3aR,4R,5R,11R,13aS)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

Traditional Name

(1S,2R,3aR,4R,5R,11R,13aS)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1H,2H,3H,4H,5H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H38O7/c1-17-12-13-28(5,6)24(31)15-23(35-20(4)30)18(2)14-22-25(19(3)16-29(22,34)26(17)32)36-27(33)21-10-8-7-9-11-21/h7-14,17,19,22-23,25-26,32,34H,15-16H2,1-6H3/b13-12+,18-14+/t17-,19-,22+,23-,25+,26-,29-/m1/s1

InChI Key

MDYKLCGYAGWJNL-UCOYIGIGSA-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 helioscopia	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	4.26	ChemAxon
pKa (Strongest Acidic)	13.27	ChemAxon
pKa (Strongest Basic)	-3.4	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	5	ChemAxon
Refractivity	137.16 m³·mol⁻¹	ChemAxon
Polarizability	54.04 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	No	ChemAxon

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0213853)

MOL for NP0213853 ((1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D MOL for NP0213853 ((1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D SDF for NP0213853 ((1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D-SDF for NP0213853 ((1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

PDB for NP0213853 ((1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D PDB for NP0213853 ((1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

SMILES for NP0213853 ((1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

INCHI for NP0213853 ((1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

Structure for NP0213853 ((1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D Structure for NP0213853 ((1s,2r,3ar,4r,5r,11r,13as)-11-(acetyloxy)-3a,4-dihydroxy-2,5,8,8,12-pentamethyl-9-oxo-1h,2h,3h,4h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)