NP-MRD: Showing NP-Card for 1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate (NP0323814)

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Record Information

Version

2.0

Created at

2022-09-12 03:29:09 UTC

Updated at

2022-09-12 03:29:09 UTC

NP-MRD ID

NP0323814

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate

Description

1-(Acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]Pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate is found in Euphorbia helioscopia. Based on a literature review very few articles have been published on 1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]Pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122205292D          

 37 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309122205292D          

 37 40  0  0  0  0            999 V2000
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    0.5710   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3160   -0.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1171   -1.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3720   -0.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6037   -2.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6037   -1.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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
 16 15  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 21 31  1  0  0  0  0
 32 31  1  4  0  0  0
 32 33  2  0  0  0  0
 12 33  1  0  0  0  0
 33 34  1  0  0  0  0
 15 35  1  0  0  0  0
 14 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323814

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1OC1C=CC(=O)OC1CC2C(C=C(C)C(=O)C3(CC(C)C(O)C3C=C1C)OC(C)=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O7/c1-8-9-23-24(35-23)10-11-26(32)36-25-14-21-20(29(21,6)7)13-17(3)28(34)30(37-19(5)31)15-18(4)27(33)22(30)12-16(25)2/h10-13,18,20-25,27,33H,8-9,14-15H2,1-7H3

> <INCHI_KEY>
DGJWKAHZGKAFHX-UHFFFAOYSA-N

> <FORMULA>
C30H42O7

> <MOLECULAR_WEIGHT>
514.659

> <EXACT_MASS>
514.293053692

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
57.62250926170643

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0^{5,7}]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate

> <JCHEM_LOGP>
4.905905982333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.52976408914423

> <JCHEM_PKA_STRONGEST_BASIC>
-3.004481187408312

> <JCHEM_POLAR_SURFACE_AREA>
102.42999999999999

> <JCHEM_REFRACTIVITY>
141.17090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0^{5,7}]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      11.560   8.534   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.186   7.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.281   5.881   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.907   4.474   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.153   3.569   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.747   2.943   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.841   1.697   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.310   1.858   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.405   0.612   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.031  -0.795   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.873   0.773   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.968  -0.473   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.444  -1.938   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.865  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.865  -4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.531  -5.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.864  -5.153   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.864  -6.693   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.369  -5.914   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.963  -6.541   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.802  -8.072   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.283  -5.636   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.066  -4.859   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.161  -3.613   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.379  -3.613   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.066  -2.367   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.590  -0.902   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.952  -1.938   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.428  -0.473   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.523   0.773   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.199  -3.613   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.460  -4.496   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.460  -2.730   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    6                                                       
CONECT    6    5    4    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   35                                                  
CONECT   15   14   16   35                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26   31                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   21   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   12   34                                                  
CONECT   34   33                                                            
CONECT   35   15   14   36   37                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
1-(Acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0,]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoic acid	Generator

Chemical Formula

C₃₀H₄₂O₇

Average Mass

514.6590 Da

Monoisotopic Mass

514.29305 Da

IUPAC Name

1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0^{5,7}]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate

Traditional Name

1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0^{5,7}]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CCCC1OC1C=CC(=O)OC1CC2C(C=C(C)C(=O)C3(CC(C)C(O)C3C=C1C)OC(C)=O)C2(C)C

InChI Identifier

InChI=1S/C30H42O7/c1-8-9-23-24(35-23)10-11-26(32)36-25-14-21-20(29(21,6)7)13-17(3)28(34)30(37-19(5)31)15-18(4)27(33)22(30)12-16(25)2/h10-13,18,20-25,27,33H,8-9,14-15H2,1-7H3

InChI Key

DGJWKAHZGKAFHX-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 helioscopia	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
Epoxy fatty acid
Fatty acid ester
Alpha-acyloxy ketone
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Ketone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Ether
Oxacycle
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	4.91	ChemAxon
pKa (Strongest Acidic)	14.53	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	102.43 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	141.17 m³·mol⁻¹	ChemAxon
Polarizability	57.62 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

163049127

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate (NP0323814)

MOL for NP0323814 (1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate)

3D MOL for NP0323814 (1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate)

3D SDF for NP0323814 (1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate)

3D-SDF for NP0323814 (1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate)

PDB for NP0323814 (1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate)

3D PDB for NP0323814 (1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate)

SMILES for NP0323814 (1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate)

INCHI for NP0323814 (1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate)

Structure for NP0323814 (1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate)

3D Structure for NP0323814 (1-(acetyloxy)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxotricyclo[10.3.0.0⁵,⁷]pentadeca-3,10-dien-9-yl 3-(3-propyloxiran-2-yl)prop-2-enoate)