NP-MRD: Showing NP-Card for 13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate (NP0191369)

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Record Information

Version

2.0

Created at

2022-09-04 08:18:21 UTC

Updated at

2022-09-04 08:18:21 UTC

NP-MRD ID

NP0191369

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

Description

13-(Acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]Pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. 13-(Acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]Pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171507102D          

 37 41  0  0  0  0            999 V2000
    4.8042    2.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8730    1.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 25 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004171507102D          

 37 41  0  0  0  0            999 V2000
    4.8042    2.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4862    0.9031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2073    0.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342   -3.9671    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  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
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 12 32  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 25 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191369

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC1=CC=CC=C1C(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3CC(C)=CC2C2C(C)(C)C12OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H37NO6/c1-15-12-20-21(14-16(2)24(20)33)29(35)17(3)26(36-27(34)19-10-8-9-11-23(19)31-7)30(37-18(4)32)25(22(29)13-15)28(30,5)6/h8-11,13-14,17,20-22,25-26,31,35H,12H2,1-7H3

> <INCHI_KEY>
RVVIYIWBNNSAIQ-UHFFFAOYSA-N

> <FORMULA>
C30H37NO6

> <MOLECULAR_WEIGHT>
507.627

> <EXACT_MASS>
507.262087915

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.73903521787253

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

> <ALOGPS_LOGP>
4.04

> <JCHEM_LOGP>
4.420867654666665

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.447813768315974

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.918313114797055

> <JCHEM_PKA_STRONGEST_BASIC>
2.129541579803452

> <JCHEM_POLAR_SURFACE_AREA>
101.93

> <JCHEM_REFRACTIVITY>
141.71480000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       8.968   5.347   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.915   4.223   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       6.415   4.572   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.968   6.046   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.468   6.395   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.416   5.271   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.863   3.798   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.363   3.448   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.810   1.975   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.310   1.625   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.758   0.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.205  -0.623   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.705  -0.973   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.757   0.152   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.152  -2.446   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.118  -1.246   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.687  -2.568   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.635  -1.354   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082  -1.880   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.358  -1.018   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.029  -3.419   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.243  -4.367   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.549  -3.844   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.089  -5.314   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.652  -5.870   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.322  -5.094   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.100  -3.570   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.600  -3.221   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.100  -2.871   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.810  -2.030   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.495  -4.288   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.152  -1.747   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.028  -0.695   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.378   0.805   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.641   1.686   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.254   1.858   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.530  -7.405   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   27                                             
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   37                                                  
CONECT   26   25   27                                                       
CONECT   27   26   15   28                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   12   28   33                                             
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   25                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
13-(Acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0,.0,]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoic acid	Generator
13-(Acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoic acid	Generator

Chemical Formula

C₃₀H₃₇NO₆

Average Mass

507.6270 Da

Monoisotopic Mass

507.26209 Da

IUPAC Name

13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

Traditional Name

13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

CAS Registry Number

Not Available

SMILES

CNC1=CC=CC=C1C(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3CC(C)=CC2C2C(C)(C)C12OC(C)=O

InChI Identifier

InChI=1S/C30H37NO6/c1-15-12-20-21(14-16(2)24(20)33)29(35)17(3)26(36-27(34)19-10-8-9-11-23(19)31-7)30(37-18(4)32)25(22(29)13-15)28(30,5)6/h8-11,13-14,17,20-22,25-26,31,35H,12H2,1-7H3

InChI Key

RVVIYIWBNNSAIQ-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Tigliane diterpenoid
Aminobenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Cyclic alcohol
Vinylogous amide
Tertiary alcohol
Ketone
Carboxylic acid ester
Amino acid or derivatives
Carboxylic acid derivative
Secondary amine
Organonitrogen compound
Amine
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	4.04	ALOGPS
logP	4.42	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	13.92	ChemAxon
pKa (Strongest Basic)	2.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	101.93 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	141.71 m³·mol⁻¹	ChemAxon
Polarizability	55.74 Å³	ChemAxon
Number of Rings	5	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

85129930

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate (NP0191369)

MOL for NP0191369 (13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D MOL for NP0191369 (13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D SDF for NP0191369 (13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D-SDF for NP0191369 (13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

PDB for NP0191369 (13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D PDB for NP0191369 (13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

SMILES for NP0191369 (13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

INCHI for NP0191369 (13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

Structure for NP0191369 (13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D Structure for NP0191369 (13-(acetyloxy)-1-hydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)