NP-MRD: Showing NP-Card for 8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate (NP0276903)

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Record Information

Version

2.0

Created at

2022-09-09 01:15:12 UTC

Updated at

2022-09-09 01:15:13 UTC

NP-MRD ID

NP0276903

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate

Description

12-Deoxyphorbo 13-Angelate 20-Acetate belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. 8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate is found in Euphorbia resinifera and Euphorbia triangularis. 12-Deoxyphorbo 13-Angelate 20-Acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191516092D          

 34 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004191516092D          

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 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0276903

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC12CC(C)C3(O)C4C=C(C)C(=O)C4(O)CC(COC(C)=O)=CC3C1C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O7/c1-8-14(2)23(30)34-26-11-16(4)27(32)19(21(26)24(26,6)7)10-18(13-33-17(5)28)12-25(31)20(27)9-15(3)22(25)29/h8-10,16,19-21,31-32H,11-13H2,1-7H3

> <INCHI_KEY>
ZZTJICHINNSOQL-UHFFFAOYSA-N

> <FORMULA>
C27H36O7

> <MOLECULAR_WEIGHT>
472.578

> <EXACT_MASS>
472.246103499

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.50144777562747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
2.906526780666666

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.037693389439973

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.575740410584388

> <JCHEM_PKA_STRONGEST_BASIC>
-3.271835910267975

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
127.49599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.736  -7.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.738  -6.623   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.087  -5.123   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.037  -4.071   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.561  -4.676   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.685  -5.729   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.910  -3.176   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.786  -2.124   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.734  -3.248   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.766  -2.898   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.819  -4.023   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.214  -1.425   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.179  -2.625   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.161  -0.301   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.384   1.223   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.714   1.999   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.592   3.534   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.201   4.196   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.067   3.323   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.458   3.985   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.945   1.788   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.150   1.443   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.610  -0.027   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.686   1.075   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.749  -1.303   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.696  -2.517   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.144  -1.991   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.420  -2.853   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.091  -0.452   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.305   0.496   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.339  -0.650   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.839  -1.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.789   0.212   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.302  -1.478   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   31   32                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   25                                             
CONECT   13   12                                                            
CONECT   14   12   15   31                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   23                                                       
CONECT   23   22   24   25   29                                             
CONECT   24   23                                                            
CONECT   25   23   12   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   23   30                                                  
CONECT   30   29                                                            
CONECT   31   14    8   32                                                  
CONECT   32   31    8   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
12-Deoxyphorbo 13-angelic acid 20-acetic acid	Generator

Chemical Formula

C₂₇H₃₆O₇

Average Mass

472.5780 Da

Monoisotopic Mass

472.24610 Da

IUPAC Name

8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate

Traditional Name

8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC12CC(C)C3(O)C4C=C(C)C(=O)C4(O)CC(COC(C)=O)=CC3C1C2(C)C

InChI Identifier

InChI=1S/C27H36O7/c1-8-14(2)23(30)34-26-11-16(4)27(32)19(21(26)24(26,6)7)10-18(13-33-17(5)28)12-25(31)20(27)9-15(3)22(25)29/h8-10,16,19-21,31-32H,11-13H2,1-7H3

InChI Key

ZZTJICHINNSOQL-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 resinifera	LOTUS Database	35616633
Euphorbia triangularis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Phorbol esters

Alternative Parents

Substituents

Phorbol ester
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
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	2.86	ALOGPS
logP	2.91	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-3.3	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	6	ChemAxon
Refractivity	127.5 m³·mol⁻¹	ChemAxon
Polarizability	51.5 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	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

44134666

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate (NP0276903)

MOL for NP0276903 (8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate)

3D MOL for NP0276903 (8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate)

3D SDF for NP0276903 (8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate)

3D-SDF for NP0276903 (8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate)

PDB for NP0276903 (8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate)

3D PDB for NP0276903 (8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate)

SMILES for NP0276903 (8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate)

INCHI for NP0276903 (8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate)

Structure for NP0276903 (8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate)

3D Structure for NP0276903 (8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl 2-methylbut-2-enoate)