NP-MRD: Showing NP-Card for (1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate (NP0169969)

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Record Information

Version

2.0

Created at

2022-09-03 06:01:19 UTC

Updated at

2022-09-03 06:01:19 UTC

NP-MRD ID

NP0169969

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

Description

(1R,2R,6R,10R,11R,13S,14R,15R)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-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. Based on a literature review very few articles have been published on (1R,2R,6R,10R,11R,13S,14R,15R)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]Pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032208012D          

 38 42  0  0  1  0            999 V2000
    4.8042    2.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2403    2.2623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0695    2.0345    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


  Mrv1652309032208012D          

 38 42  0  0  1  0            999 V2000
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    0.9697   -1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3368   -2.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -0.9360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6223   -0.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095    0.4313    0.0000 C   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
    2.4862    0.9031    0.0000 O   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
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  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
 23 21  1  6  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  1  0  0  0  0
 26 27  2  0  0  0  0
 25 28  2  0  0  0  0
 29 28  1  6  0  0  0
 15 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 12 34  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0169969

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC1=CC=CC=C1C(=O)O[C@@H]1[C@@H](C)[C@]2(O)[C@@H]3C=C(C)C(=O)[C@@H]3CC(C=O)=C[C@@H]2[C@@H]2C(C)(C)[C@]12OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H35NO7/c1-15-11-21-20(24(15)34)12-18(14-32)13-22-25-28(4,5)30(25,38-17(3)33)26(16(2)29(21,22)36)37-27(35)19-9-7-8-10-23(19)31-6/h7-11,13-14,16,20-22,25-26,31,36H,12H2,1-6H3/t16-,20-,21-,22-,25-,26-,29+,30-/m1/s1

> <INCHI_KEY>
ZWFZCPRBVCCRMO-BDZHHECYSA-N

> <FORMULA>
C30H35NO7

> <MOLECULAR_WEIGHT>
521.61

> <EXACT_MASS>
521.241352471

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.68579185625988

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,6R,10R,11R,13S,14R,15R)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
3.4539440013333333

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.280670451230527

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.917473307366897

> <JCHEM_PKA_STRONGEST_BASIC>
2.129541636175537

> <JCHEM_POLAR_SURFACE_AREA>
119.0

> <JCHEM_REFRACTIVITY>
142.5066

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.67e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,6R,10R,11R,13S,14R,15R)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         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       7.530  -7.405   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.799  -8.279   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.322  -5.094   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.100  -3.570   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.600  -3.221   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.100  -2.871   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.810  -2.030   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.495  -4.288   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.152  -1.747   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.028  -0.695   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.378   0.805   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.254   1.858   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.641   1.686   0.000  0.00  0.00           O+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   34                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   29                                             
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   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   15   30                                                  
CONECT   30   29   31   34                                                  
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   12   30   35                                             
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,6R,10R,11R,13S,14R,15R)-13-(Acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0,.0,]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoic acid	Generator

Chemical Formula

C₃₀H₃₅NO₇

Average Mass

521.6100 Da

Monoisotopic Mass

521.24135 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CNC1=CC=CC=C1C(=O)O[C@@H]1[C@@H](C)[C@]2(O)[C@@H]3C=C(C)C(=O)[C@@H]3CC(C=O)=C[C@@H]2[C@@H]2C(C)(C)[C@]12OC(C)=O

InChI Identifier

InChI=1S/C30H35NO7/c1-15-11-21-20(24(15)34)12-18(14-32)13-22-25-28(4,5)30(25,38-17(3)33)26(16(2)29(21,22)36)37-27(35)19-9-7-8-10-23(19)31-6/h7-11,13-14,16,20-22,25-26,31,36H,12H2,1-6H3/t16-,20-,21-,22-,25-,26-,29+,30-/m1/s1

InChI Key

ZWFZCPRBVCCRMO-BDZHHECYSA-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
Vinylogous amide
Tertiary alcohol
Cyclic alcohol
Amino acid or derivatives
Ketone
Carboxylic acid ester
Secondary amine
Carboxylic acid derivative
Amine
Aldehyde
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
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

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

162901455

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate (NP0169969)

MOL for NP0169969 ((1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D MOL for NP0169969 ((1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D SDF for NP0169969 ((1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D-SDF for NP0169969 ((1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

PDB for NP0169969 ((1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D PDB for NP0169969 ((1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

SMILES for NP0169969 ((1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

INCHI for NP0169969 ((1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

Structure for NP0169969 ((1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D Structure for NP0169969 ((1r,2r,6r,10r,11r,13s,14r,15r)-13-(acetyloxy)-8-formyl-1-hydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)