NP-MRD: Showing NP-Card for N-trans-Sinapoyltyramine (NP0050447)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 21:39:46 UTC

Updated at

2022-04-27 21:39:46 UTC

NP-MRD ID

NP0050447

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-trans-Sinapoyltyramine

Description

N-Trans-Sinapoyltyramine belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. N-trans-Sinapoyltyramine is found in Illigera luzonensis, Lindera glauca, Litsea hypophaea, Mitrephora tomentosa, Monascus pilosus, Peperomia duclouxii, Peperomia heyneana and Populus trichocarpa. N-trans-Sinapoyltyramine was first documented in 2010 (PMID: 20450045). Based on a literature review a small amount of articles have been published on N-Trans-Sinapoyltyramine (PMID: 32495600) (PMID: 32212861) (PMID: 29552819) (PMID: 30263405).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223392D          

 25 26  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
    0.0000   -4.1250    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 N   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
    2.1434   -2.8875    0.0000 O   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
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    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
   -2.1434   -3.7125    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
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  1 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050447

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)NCCC2=CC=C(O)C=C2)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO5/c1-24-16-11-14(12-17(25-2)19(16)23)5-8-18(22)20-10-9-13-3-6-15(21)7-4-13/h3-8,11-12,21,23H,9-10H2,1-2H3,(H,20,22)/b8-5+

> <INCHI_KEY>
IEDBNTAKVGBZEP-VMPITWQZSA-N

> <FORMULA>
C19H21NO5

> <MOLECULAR_WEIGHT>
343.379

> <EXACT_MASS>
343.14197278

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
37.12601060564254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
2.6434808596666666

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.718842099628079

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.09500163073988

> <JCHEM_PKA_STRONGEST_BASIC>
-0.38857946807695287

> <JCHEM_POLAR_SURFACE_AREA>
88.02000000000001

> <JCHEM_REFRACTIVITY>
96.03460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-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       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.667  -7.700   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2   24                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
CONECT   19   12   20                                                       
CONECT   20   19                                                            
CONECT   21    2   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23    1                                                       
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₁NO₅

Average Mass

343.3790 Da

Monoisotopic Mass

343.14197 Da

IUPAC Name

(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide

Traditional Name

(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)NCCC2=CC=C(O)C=C2)=CC(OC)=C1O

InChI Identifier

InChI=1S/C19H21NO5/c1-24-16-11-14(12-17(25-2)19(16)23)5-8-18(22)20-10-9-13-3-6-15(21)7-4-13/h3-8,11-12,21,23H,9-10H2,1-2H3,(H,20,22)/b8-5+

InChI Key

IEDBNTAKVGBZEP-VMPITWQZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Illigera luzonensis	LOTUS Database	35616633
Lindera glauca	Plant	KNApSAcK
Litsea hypophaea	LOTUS Database	35616633
Mitrephora tomentosa	LOTUS Database	35616633
Monascus pilosus	LOTUS Database	35616633
Peperomia duclouxii	Plant	KNApSAcK
Peperomia heyneana	LOTUS Database	35616633
Populus trichocarpa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid amide
Hydroxycinnamic acid or derivatives
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Ether
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxycinnamic acid (CHEBI:70105 )

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	2.38	ALOGPS
logP	2.64	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	-0.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.02 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	96.03 m³·mol⁻¹	ChemAxon
Polarizability	37.13 Å³	ChemAxon
Number of Rings	2	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

C00000661

Chemspider ID

23285056

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25245053

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yao HN, Zhang H, Wang WX, Zan NL, Liu DF, Zhao YF, Zheng J, Tu PF, Li J: [Two new phenylpropanoid amide glycosides from whole plants of Corydalis racemosa]. Zhongguo Zhong Yao Za Zhi. 2020 May;45(10):2411-2416. doi: 10.19540/j.cnki.cjcmm.20200220.202. [PubMed:32495600 ]
Truong LH, Cuong NH, Dang TH, Hanh NTM, Thi VL, Tran Thi Hong H, Tran Hong Quang, Nguyen HD, Nguyen Xuan C, Nguyen Hoai N, Minh CV: Cytotoxic constituents from Isotrema tadungense. J Asian Nat Prod Res. 2021 May;23(5):491-497. doi: 10.1080/10286020.2020.1739661. Epub 2020 Mar 26. [PubMed:32212861 ]
Peng ZT, Chao LH, Huo HX, Chen XN, Yao HN, Zhang Y, Zhao YF, Tu PF, Zheng J, Li J: [Phenylpropanoid amides from whole plants of Corydalis edulis]. Zhongguo Zhong Yao Za Zhi. 2018 Jan;43(1):109-113. doi: 10.19540/j.cnki.cjcmm.20171027.007. [PubMed:29552819 ]
Choi HS, Cho JY, Jin MR, Lee YG, Kim SJ, Ham KS, Moon JH: Phenolics, acyl galactopyranosyl glycerol, and lignan amides from Tetragonia tetragonioides (Pall.) Kuntze. Food Sci Biotechnol. 2016 Oct 31;25(5):1275-1281. doi: 10.1007/s10068-016-0201-9. eCollection 2016. [PubMed:30263405 ]
Li Y, Gong Z, Ma C, Feng X, Huang J: [Amides from Peperomia tetraphylla]. Zhongguo Zhong Yao Za Zhi. 2010 Feb;35(4):468-9. doi: 10.4268/cjcmm20100413. [PubMed:20450045 ]

Showing NP-Card for N-trans-Sinapoyltyramine (NP0050447)

MOL for NP0050447 (N-trans-Sinapoyltyramine)

3D MOL for NP0050447 (N-trans-Sinapoyltyramine)

3D SDF for NP0050447 (N-trans-Sinapoyltyramine)

3D-SDF for NP0050447 (N-trans-Sinapoyltyramine)

PDB for NP0050447 (N-trans-Sinapoyltyramine)

3D PDB for NP0050447 (N-trans-Sinapoyltyramine)

SMILES for NP0050447 (N-trans-Sinapoyltyramine)

INCHI for NP0050447 (N-trans-Sinapoyltyramine)

Structure for NP0050447 (N-trans-Sinapoyltyramine)

3D Structure for NP0050447 (N-trans-Sinapoyltyramine)