NPASS Natural Product

Natural Product: NPC296898

Natural Product ID:	NPC296898
Common Name:	Trans-N-Sinapoyltyramine
IUPAC Name:	(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
Synonyms:	N-Trans-Sinapoyltyramine; Trans-N-Sinapoyltyramine
Molecular Formula:	C19H21NO5
Standard InCHIKey:	IEDBNTAKVGBZEP-VMPITWQZSA-N
Standard InCHI:	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+
Canonical SMILES:	COc1cc(/C=C/C(=NCCc2ccc(cc2)O)O)cc(c1O)OC
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO16798	Piper sylvaticum	Species	Piperaceae	Eukaryota		UNPD*
NPO21569	Helichrysum fulvum	Species	Asteraceae	Eukaryota		UNPD*
NPO22727	Avena fatua	Species	Poaceae	Eukaryota		UNPD*
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	Whole Plants	PMID[21158422]
NPO7472	Litsea hypophaea	Species	Lauraceae	Eukaryota	roots	PMID[20384293]

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Biological Activity

Activity Type	# Activity
IC50	15
MIC	3

Activity Type	# Activity
Cell Line	13
Individual Protein	1
Organism	3
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	62.5	ug/ml	10.1007/s00044-012-0419-x
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	>	40000	nM	25241925
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	>	20000	nM	27258622
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000	nM	25241925
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	>	20	ug/ml	17547458
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	>	20	ug/ml	17547458
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	62.5	ug/ml	10.1007/s00044-012-0419-x
NPT2	Others	Unspecified		IC50	>	40000	nM	25241925
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20	ug/ml	17547458
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	80200	nM	27258622

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Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC296898 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	129
0.1-0.2	1050
0.2-0.3	3797
0.3-0.4	9435
0.4-0.5	3020
0.5-0.6	4311
0.6-0.7	6361
0.7-0.8	2403
0.8-0.85	290
0.85-0.9	78
0.9-0.95	15
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.8201	Intermediate Similarity	NPC224157
0.8201	Intermediate Similarity	NPC91291
0.8201	Intermediate Similarity	NPC63574
0.8201	Intermediate Similarity	NPC192687
0.8214	Intermediate Similarity	NPC86655

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Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC296898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	668
0.2-0.3	1061
0.3-0.4	2304
0.4-0.5	2496
0.5-0.6	1496
0.6-0.7	838
0.7-0.8	152
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6933	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4585	Approved
0.6933	Remote Similarity	NPD1130	Approved
0.6933	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1136	Approved

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Structure

CID296898 OpenBabel06191716102D 25 26 0 0 0 0 0 0 0 0999 V2000 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 6 1 0 0 0 0 3 13 2 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 20 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 20 2 3 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	25245053
ChEMBL	CHEMBL226587
ZINC

Physicochemical Properties

Molecular Weight:	343.14
ALogP:	-0.7017
MLogP:	2.89
XLogP:	2.665
# Rotatable Bonds:	12
Polar Surface Area:	91.51
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	25

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