NP-MRD: Showing NP-Card for Sapintoxin C (NP0080079)

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Record Information

Version

2.0

Created at

2022-04-29 01:08:43 UTC

Updated at

2022-04-29 01:08:43 UTC

NP-MRD ID

NP0080079

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sapintoxin C

Description

(1R,2S,6R,7S,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,7-dihydroxy-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. Sapintoxin C is found in Sapium indicum . Based on a literature review very few articles have been published on (1R,2S,6R,7S,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,7-dihydroxy-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

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203082D          

 38 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292203082D          

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    5.2914    0.9997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9768   -2.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4138   -1.7432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5633    1.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  1  0  0  0
 11 10  1  0  0  0  0
 11  3  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
 15 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 13 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 26 33  1  0  0  0  0
 12 34  1  1  0  0  0
 11 35  1  1  0  0  0
  8 36  1  0  0  0  0
  7 37  1  6  0  0  0
  1 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC1=C(C=CC=C1)C(=O)O[C@@H]1[C@@H](C)[C@]2(O)[C@H]3C=C(C)C(=O)[C@H]3[C@H](O)C(C)=C[C@H]2[C@@H]2C(C)(C)[C@]12OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H37NO7/c1-14-12-19-22(23(14)33)24(34)15(2)13-20-25-28(5,6)30(25,38-17(4)32)26(16(3)29(19,20)36)37-27(35)18-10-8-9-11-21(18)31-7/h8-13,16,19-20,22,24-26,31,34,36H,1-7H3/t16-,19+,20+,22+,24-,25-,26-,29+,30-/m1/s1

> <INCHI_KEY>
KESIQXYRXFIECZ-GKKQYMHISA-N

> <FORMULA>
C30H37NO7

> <MOLECULAR_WEIGHT>
523.626

> <EXACT_MASS>
523.257002535

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.80410142443344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,6R,7S,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,7-dihydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
3.3459640476666657

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.360905564182808

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.70667535951877

> <JCHEM_PKA_STRONGEST_BASIC>
2.1295415757810545

> <JCHEM_POLAR_SURFACE_AREA>
122.16000000000003

> <JCHEM_REFRACTIVITY>
143.0763

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6R,7S,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,7-dihydroxy-4,8,12,12,15-pentamethyl-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                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      12.842   1.232   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.394   1.758   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.447   0.544   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.309  -0.732   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.789  -0.307   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.003  -1.254   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.848  -2.201   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.412  -2.758   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.082  -1.982   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.859  -0.458   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.912   0.666   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.464   2.140   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.965   2.489   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.912   1.365   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.359  -0.108   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.860   0.241   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.909  -0.971   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.396   0.720   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.788   2.418   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.314   1.970   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.519   0.652   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.190   3.023   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.517   3.963   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.570   5.087   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.070   4.738   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.123   6.561   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.175   7.685   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       9.675   7.336   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      10.122   5.862   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.728   9.159   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.228   9.508   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.175   8.384   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.623   6.910   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.517   3.264   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.877   1.866   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       9.290  -4.293   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.972  -3.254   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      14.118   2.094   0.000  0.00  0.00           C+0
CONECT    1    2    5   38                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    4    8   37                                                  
CONECT    8    7    9   36                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    3   12   35                                             
CONECT   12   11   13   34                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15   16   19                                             
CONECT   15   14   10   16                                                  
CONECT   16   15   14   17   18                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   13   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   33                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   26                                                       
CONECT   34   12                                                            
CONECT   35   11                                                            
CONECT   36    8                                                            
CONECT   37    7                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,6R,7S,10S,11R,13S,14R,15R)-13-(Acetyloxy)-1,7-dihydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0,.0,]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoic acid	Generator

Chemical Formula

C₃₀H₃₇NO₇

Average Mass

523.6260 Da

Monoisotopic Mass

523.25700 Da

IUPAC Name

(1R,2S,6R,7S,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,7-dihydroxy-4,8,12,12,15-pentamethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

Traditional Name

(1R,2S,6R,7S,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,7-dihydroxy-4,8,12,12,15-pentamethyl-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

CNC1=C(C=CC=C1)C(=O)O[C@@H]1[C@@H](C)[C@]2(O)[C@H]3C=C(C)C(=O)[C@H]3[C@H](O)C(C)=C[C@H]2[C@@H]2C(C)(C)[C@]12OC(C)=O

InChI Identifier

InChI=1S/C30H37NO7/c1-14-12-19-22(23(14)33)24(34)15(2)13-20-25-28(5,6)30(25,38-17(4)32)26(16(3)29(19,20)36)37-27(35)18-10-8-9-11-21(18)31-7/h8-13,16,19-20,22,24-26,31,34,36H,1-7H3/t16-,19+,20+,22+,24-,25-,26-,29+,30-/m1/s1

InChI Key

KESIQXYRXFIECZ-GKKQYMHISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Sapium indicum	Plant	KNApSAcK

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
Benzoate ester
Aminobenzoic acid or derivatives
Benzoic acid or derivatives
Phenylalkylamine
Aniline or substituted anilines
Benzoyl
Secondary aliphatic/aromatic amine
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Vinylogous amide
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Amino acid or derivatives
Secondary amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	3.29	ALOGPS
logP	3.35	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	13.71	ChemAxon
pKa (Strongest Basic)	2.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.16 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	143.08 m³·mol⁻¹	ChemAxon
Polarizability	56.8 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

163006487

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Sapintoxin C (NP0080079)

MOL for NP0080079 (Sapintoxin C)

3D MOL for NP0080079 (Sapintoxin C)

3D SDF for NP0080079 (Sapintoxin C)

3D-SDF for NP0080079 (Sapintoxin C)

PDB for NP0080079 (Sapintoxin C)

3D PDB for NP0080079 (Sapintoxin C)

SMILES for NP0080079 (Sapintoxin C)

INCHI for NP0080079 (Sapintoxin C)

Structure for NP0080079 (Sapintoxin C)

3D Structure for NP0080079 (Sapintoxin C)