NP-MRD: Showing NP-Card for sapintoxin d (NP0190254)

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Record Information

Version

2.0

Created at

2022-09-04 06:53:40 UTC

Updated at

2022-09-04 06:53:40 UTC

NP-MRD ID

NP0190254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sapintoxin d

Description

Sapintoxin D belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. Sapintoxin D is a moderately basic compound (based on its pKa). sapintoxin d was first documented in 1990 (PMID: 2323005). A phorbol ester consisting of phorbol that is acylated at positions 12 and 13 by 2-(methylamino)benzoyl and acetyl groups respectively (PMID: 21542090) (PMID: 19512879) (PMID: 11513612).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303211707152D          

 44 48  0  0  1  0            999 V2000
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  2 42  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652303211707152D          

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    1.2644   -5.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8282   -5.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886   -6.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7851   -6.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -5.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4609   -5.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030   -4.5993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1367   -3.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6159   -2.2310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0137   -2.7948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7758   -2.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3780   -3.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9630   -1.7517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0520   -1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7331   -1.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4572   -0.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 21 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 24 37  1  0  0  0  0
  2 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 37 42  1  0  0  0  0
  2 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@]3([H])C=C(CO)C[C@]4(O)C(=O)C(C)=C[C@@]4([H])[C@@]3(O)[C@]([H])(C)[C@@]([H])(OC(=O)C3=CC=CC=C3NC)[C@@]1(OC(C)=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H37NO8/c1-15-11-22-28(36,24(15)34)13-18(14-32)12-20-23-27(4,5)30(23,39-17(3)33)25(16(2)29(20,22)37)38-26(35)19-9-7-8-10-21(19)31-6/h7-12,16,20,22-23,25,31-32,36-37H,13-14H2,1-6H3/t16-,20+,22-,23-,25-,28-,29-,30-/m1/s1

> <INCHI_KEY>
UPAIGGMQTARRMN-CSSCWBSHSA-N

> <FORMULA>
C30H37NO8

> <MOLECULAR_WEIGHT>
539.625

> <EXACT_MASS>
539.251917155

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.2697864743419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-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>
2.78

> <JCHEM_LOGP>
2.278320641999999

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.933210389400198

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.570369306456584

> <JCHEM_PKA_STRONGEST_BASIC>
2.1295415475023556

> <JCHEM_POLAR_SURFACE_AREA>
142.39000000000001

> <JCHEM_REFRACTIVITY>
144.9447

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-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                                 21-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-MAR-17         0                                  
HETATM    1  H   UNK     0       1.248  -1.191   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.597  -2.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.097  -2.341   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       4.566  -1.881   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       3.319  -0.818   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.650  -0.042   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.528   1.493   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.137   2.155   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.086  -0.598   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.546  -2.067   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.622  -0.965   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.026  -2.493   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.240  -1.545   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.079  -4.032   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.356  -4.893   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.632  -4.558   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.685  -3.344   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       4.909  -2.013   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       4.149  -3.466   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.115  -4.665   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.702  -4.939   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       3.255  -6.413   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       4.755  -6.063   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.202  -5.289   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       0.702  -5.638   0.000  0.00  0.00           H+0
HETATM   26  O   UNK     0       1.755  -6.762   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.807  -7.886   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.307  -7.537   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.360  -9.360   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.413 -10.484   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.965 -11.958   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.466 -12.307   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.413 -11.183   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.860  -9.710   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -0.192  -8.585   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       0.255  -7.112   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.150  -4.165   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.026  -5.217   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -1.448  -4.770   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.572  -5.822   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.798  -3.270   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       0.097  -3.040   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -1.368  -2.567   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -0.853  -1.829   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37   42                                             
CONECT    3    2    4    5   19                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    3   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25   26   37                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   24    2   38   42                                             
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   37    2   43   44                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Value	Source
Phorbol 12-(2-methylamino)benzoate 13-acetate	ChEBI
Phorbol 12-(2-methylamino)benzoic acid 13-acetic acid	Generator
5,9,11-Trihydroxyprosta-6E,14Z-dien-1-Oic acid	Generator
CCRIS 7233	HMDB

Chemical Formula

C₃₀H₃₇NO₈

Average Mass

539.6250 Da

Monoisotopic Mass

539.25192 Da

IUPAC Name

(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-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

Traditional Name

(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-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

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@]3([H])C=C(CO)C[C@]4(O)C(=O)C(C)=C[C@@]4([H])[C@@]3(O)[C@]([H])(C)[C@@]([H])(OC(=O)C3=CC=CC=C3NC)[C@@]1(OC(C)=O)C2(C)C

InChI Identifier

InChI=1S/C30H37NO8/c1-15-11-22-28(36,24(15)34)13-18(14-32)12-20-23-27(4,5)30(23,39-17(3)33)25(16(2)29(20,22)37)38-26(35)19-9-7-8-10-21(19)31-6/h7-12,16,20,22-23,25,31-32,36-37H,13-14H2,1-6H3/t16-,20+,22-,23-,25-,28-,29-,30-/m1/s1

InChI Key

UPAIGGMQTARRMN-CSSCWBSHSA-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 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
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
Primary alcohol
Amine
Organonitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

phorbol ester (CHEBI:72442 )

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	2.78	ALOGPS
logP	2.28	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	2.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.39 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	144.94 m³·mol⁻¹	ChemAxon
Polarizability	57.27 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

HMDB0062413

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

114977

PDB ID

Not Available

ChEBI ID

72442

Good Scents ID

Not Available

References

General References

Kedei N, Lubart E, Lewin NE, Telek A, Lim L, Mannan P, Garfield SH, Kraft MB, Keck GE, Kolusheva S, Jelinek R, Blumberg PM: Some phorbol esters might partially resemble bryostatin 1 in their actions on LNCaP prostate cancer cells and U937 leukemia cells. Chembiochem. 2011 May 16;12(8):1242-51. doi: 10.1002/cbic.201100064. Epub 2011 May 3. [PubMed:21542090 ]
Wickley PJ, Yuge R, Martin BA, Meyer JS, Damron DS: Propofol activates and allosterically modulates recombinant protein kinase C epsilon. Anesthesiology. 2009 Jul;111(1):36-43. doi: 10.1097/ALN.0b013e3181a3274b. [PubMed:19512879 ]
Ho C, Slater SJ, Stagliano B, Stubbs CD: The C1 domain of protein kinase C as a lipid bilayer surface sensing module. Biochemistry. 2001 Aug 28;40(34):10334-41. doi: 10.1021/bi002839x. [PubMed:11513612 ]
Brooks G, Brooks SF: Both tumour-promoting and non-promoting phorbol esters inhibit [125I]EGF binding and stimulate the phosphorylation of an 80 kd protein kinase C substrate protein in intact quiescent swiss 3T3 cells. Carcinogenesis. 1990 Apr;11(4):667-72. doi: 10.1093/carcin/11.4.667. [PubMed:2323005 ]
LOTUS database [Link]

Showing NP-Card for sapintoxin d (NP0190254)

MOL for NP0190254 (sapintoxin d)

3D MOL for NP0190254 (sapintoxin d)

3D SDF for NP0190254 (sapintoxin d)

3D-SDF for NP0190254 (sapintoxin d)

PDB for NP0190254 (sapintoxin d)

3D PDB for NP0190254 (sapintoxin d)

SMILES for NP0190254 (sapintoxin d)

INCHI for NP0190254 (sapintoxin d)

Structure for NP0190254 (sapintoxin d)

3D Structure for NP0190254 (sapintoxin d)