NP-MRD: Showing NP-Card for (1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate (NP0157719)

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Record Information

Version

2.0

Created at

2022-09-02 15:10:07 UTC

Updated at

2022-09-02 15:10:07 UTC

NP-MRD ID

NP0157719

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate

Description

(1R,2S,4S,7S,9R,10E,13R,15S,16S)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]Hexadec-10-en-16-yl 2-methylpropanoate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate is found in Euphorbia characias. Based on a literature review very few articles have been published on (1R,2S,4S,7S,9R,10E,13R,15S,16S)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]Hexadec-10-en-16-yl 2-methylpropanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217102D          

 32 35  0  0  1  0            999 V2000
    7.5151    1.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040    2.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0784    3.0758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1185    2.0173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9441    1.2110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6891    1.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2563    0.9661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0744    1.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5065    0.1102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3927   -1.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0508    0.3929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.2806    1.2459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0752    1.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6236    2.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8671    2.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9166    1.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697    0.5868    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


  Mrv1652309022217102D          

 32 35  0  0  1  0            999 V2000
    7.5151    1.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0157719

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O6/c1-13(2)23(29)30-20-15(4)12-26(31-16(5)27)19(20)22-25(8,32-22)10-9-17-18(24(17,6)7)11-14(3)21(26)28/h11,13,15,17-20,22H,9-10,12H2,1-8H3/b14-11+/t15-,17-,18+,19+,20-,22-,25-,26+/m0/s1

> <INCHI_KEY>
CLBNVMAQWXNMGF-PKBRFECASA-N

> <FORMULA>
C26H38O6

> <MOLECULAR_WEIGHT>
446.584

> <EXACT_MASS>
446.266838944

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
48.85578372740298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4S,7S,9R,10E,13R,15S,16S)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0^{2,4}.0^{7,9}]hexadec-10-en-16-yl 2-methylpropanoate

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
4.730011923999999

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.208730273005554

> <JCHEM_POLAR_SURFACE_AREA>
82.19999999999999

> <JCHEM_REFRACTIVITY>
119.16439999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,7S,9R,10E,13R,15S,16S)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0^{2,4}.0^{7,9}]hexadec-10-en-16-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      14.028   3.202   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.888   4.236   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.213   5.742   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.421   3.766   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.096   2.261   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.486   2.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.545   1.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.072   2.003   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.809   0.451   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.470  -0.940   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      15.005  -1.062   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.879   0.206   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      15.666  -2.453   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.201  -2.576   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.793  -3.721   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.295   0.733   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.637  -0.659   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.690  -2.198   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.330  -1.474   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.948  -2.966   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.791  -1.454   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.506  -0.605   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.885   0.804   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.124   2.326   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.607   2.740   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.631   3.891   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.216   5.374   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.102   3.437   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.952   4.722   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.687   1.772   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.578   2.841   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.303   1.095   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   16   28                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9    5   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   19                                                       
CONECT   19   18   17   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    5   29                                                  
CONECT   29   28                                                            
CONECT   30   24   23   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,4S,7S,9R,10E,13R,15S,16S)-13-(Acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0,.0,]hexadec-10-en-16-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₂₆H₃₈O₆

Average Mass

446.5840 Da

Monoisotopic Mass

446.26684 Da

IUPAC Name

(1R,2S,4S,7S,9R,10E,13R,15S,16S)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0^{2,4}.0^{7,9}]hexadec-10-en-16-yl 2-methylpropanoate

Traditional Name

(1R,2S,4S,7S,9R,10E,13R,15S,16S)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0^{2,4}.0^{7,9}]hexadec-10-en-16-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H38O6/c1-13(2)23(29)30-20-15(4)12-26(31-16(5)27)19(20)22-25(8,32-22)10-9-17-18(24(17,6)7)11-14(3)21(26)28/h11,13,15,17-20,22H,9-10,12H2,1-8H3/b14-11+/t15-,17-,18+,19+,20-,22-,25-,26+/m0/s1

InChI Key

CLBNVMAQWXNMGF-PKBRFECASA-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 characias	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
Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Oxirane
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
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	3.88	ALOGPS
logP	4.73	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	82.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.16 m³·mol⁻¹	ChemAxon
Polarizability	48.86 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	No	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

162956669

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate (NP0157719)

MOL for NP0157719 ((1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate)

3D MOL for NP0157719 ((1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate)

3D SDF for NP0157719 ((1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate)

3D-SDF for NP0157719 ((1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate)

PDB for NP0157719 ((1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate)

3D PDB for NP0157719 ((1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate)

SMILES for NP0157719 ((1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate)

INCHI for NP0157719 ((1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate)

Structure for NP0157719 ((1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate)

3D Structure for NP0157719 ((1r,2s,4s,7s,9r,10e,13r,15s,16s)-13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl 2-methylpropanoate)