NP-MRD: Showing NP-Card for Tenucaulin A (NP0073763)

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Record Information

Version

2.0

Created at

2022-04-28 18:59:19 UTC

Updated at

2022-04-28 18:59:19 UTC

NP-MRD ID

NP0073763

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tenucaulin A

Description

Tenucaulin A belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Tenucaulin A is found in Aglaia tenuicaulis. Based on a literature review very few articles have been published on Tenucaulin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
    6.8451    3.4170   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0471    3.6267    0.1306 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447    2.0122    0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5021    0.9929   -0.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9160   -0.3216    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871   -1.2592   -0.7697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2198   -0.4860    1.1820 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6113   -1.6322    1.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4052   -2.1461    0.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4959   -2.4636   -0.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1277   -3.0375   -0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9024   -2.0395   -0.7496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2257   -2.3623   -1.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -3.5119   -1.5139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2979   -1.3933   -0.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1583   -0.1738   -0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2631    0.7565   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0076    2.0430    0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9926    2.9855    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3054    2.6932    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5784    1.4394   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5730    0.4893   -0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1650    2.4080    0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0843    3.4857   -1.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4003    4.1528    0.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7831    1.8409    1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0520    1.1073   -1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3001   -1.4544    2.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3764   -2.4778    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1023   -3.1028    1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5790   -1.4108    1.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5588   -1.5369   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2188   -3.2353   -0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1757   -3.3767   -2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -3.8744   -0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6747   -1.0951   -0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386   -1.6694   -1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1658    0.1684   -0.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9766    2.3047    0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7984    3.9783    0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0782    3.4473    0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5969    1.1755   -0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8696   -0.4639   -0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 15 37  1  0
 16 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
M  END


  Mrv1652304282220592D          

 22 22  0  0  0  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073763

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS\C=C\C(=O)OCCCCNC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO3S/c1-22-14-11-17(20)21-13-6-5-12-18-16(19)10-9-15-7-3-2-4-8-15/h2-4,7-11,14H,5-6,12-13H2,1H3,(H,18,19)/b10-9+,14-11+

> <INCHI_KEY>
IWBBTXUKMRJOBR-QDCWQMMGSA-N

> <FORMULA>
C17H21NO3S

> <MOLECULAR_WEIGHT>
319.42

> <EXACT_MASS>
319.124214714

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
36.026811399256374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2E)-3-phenylprop-2-enamido]butyl (2E)-3-(methylsulfanyl)prop-2-enoate

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
3.104197989666667

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.658652490897165

> <JCHEM_PKA_STRONGEST_BASIC>
-0.30894653647371084

> <JCHEM_POLAR_SURFACE_AREA>
55.4

> <JCHEM_REFRACTIVITY>
92.22939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2E)-3-phenylprop-2-enamido]butyl (2E)-3-(methylsulfanyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   21  S   UNK     0      13.337  -4.620   0.000  0.00  0.00           S+0
HETATM   22  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
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                                                       
CONECT    9    1   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₁NO₃S

Average Mass

319.4200 Da

Monoisotopic Mass

319.12421 Da

IUPAC Name

4-[(2E)-3-phenylprop-2-enamido]butyl (2E)-3-(methylsulfanyl)prop-2-enoate

Traditional Name

4-[(2E)-3-phenylprop-2-enamido]butyl (2E)-3-(methylsulfanyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CS\C=C\C(=O)OCCCCNC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H21NO3S/c1-22-14-11-17(20)21-13-6-5-12-18-16(19)10-9-15-7-3-2-4-8-15/h2-4,7-11,14H,5-6,12-13H2,1H3,(H,18,19)/b10-9+,14-11+

InChI Key

IWBBTXUKMRJOBR-QDCWQMMGSA-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
Aglaia tenuicaulis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid amides

Direct Parent

Cinnamic acid amides

Alternative Parents

Substituents

Cinnamic acid amide
Styrene
Monocyclic benzene moiety
Vinylogous thioester
Benzenoid
Acrylic acid or derivatives
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Thioenolether
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Sulfenyl compound
Carbonyl group
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.07	ALOGPS
logP	3.1	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	15.66	ChemAxon
pKa (Strongest Basic)	-0.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.4 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	92.23 m³·mol⁻¹	ChemAxon
Polarizability	36.03 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00034307

Chemspider ID

28284961

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101844308

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Tenucaulin A (NP0073763)

MOL for NP0073763 (Tenucaulin A)

3D MOL for NP0073763 (Tenucaulin A)

3D SDF for NP0073763 (Tenucaulin A)

3D-SDF for NP0073763 (Tenucaulin A)

PDB for NP0073763 (Tenucaulin A)

3D PDB for NP0073763 (Tenucaulin A)

SMILES for NP0073763 (Tenucaulin A)

INCHI for NP0073763 (Tenucaulin A)

Structure for NP0073763 (Tenucaulin A)

3D Structure for NP0073763 (Tenucaulin A)