NPASS Natural Product

Natural Product: NPC178129

Natural Product ID:	NPC178129
Common Name:	Tournefolic Acid B Ethyl Ester
IUPAC Name:	ethyl (E)-3-(2,3,10-trihydroxybenzo[b][1]benzoxepin-7-yl)prop-2-enoate
Synonyms:	Tournefolic Acid B Ethyl Ester
Molecular Formula:	C19H16O6
Standard InCHIKey:	WIXDFLWXLUYIGH-VMPITWQZSA-N
Standard InCHI:	InChI=1S/C19H16O6/c1-2-24-18(23)8-5-11-4-7-14(20)19-13(11)6-3-12-9-15(21)16(22)10-17(12)25-19/h3-10,20-22H,2H2,1H3/b8-5+
Canonical SMILES:	CCOC(=O)/C=C/c1ccc(c2c1C=Cc1c(O2)cc(c(c1)O)O)O
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	Collection Location	Collection Time	Reference
NPO24054	Tournefortia sarmentosa	Species	Heliotropiaceae	Eukaryota				PMID[12027757]

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Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	8.6		PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	510	nM	18280170

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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 NPC178129 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	248
0.1-0.2	1176
0.2-0.3	2664
0.3-0.4	6498
0.4-0.5	6657
0.5-0.6	2153
0.6-0.7	4077
0.7-0.8	5789
0.8-0.85	1324
0.85-0.9	276
0.9-0.95	26
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.86	High Similarity	NPC102934
0.86	High Similarity	NPC93924
0.86	High Similarity	NPC236166
0.86	High Similarity	NPC252402
0.8601	High Similarity	NPC309744

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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 NPC178129 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	880
0.2-0.3	1684
0.3-0.4	2679
0.4-0.5	1826
0.5-0.6	1006
0.6-0.7	629
0.7-0.8	183
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6994	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5709	Phase 3
0.7007	Intermediate Similarity	NPD5585	Approved
0.7013	Intermediate Similarity	NPD1296	Phase 2

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Structure

NPC178129 OpenBabel07101719512D 25 27 0 0 0 0 0 0 0 0999 V2000 0.7818 6.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0842 6.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 1.1982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5382 -0.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4088 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9693 0.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 -0.5290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 4.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 -0.8765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9665 0.4467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0988 -1.3552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 5.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0842 5.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 24 1 0 0 0 0 3 6 2 0 0 0 0 3 12 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 15 2 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 12 17 2 0 0 0 0 13 19 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10042848
ChEMBL	CHEMBL515985
ZINC

Physicochemical Properties

Molecular Weight:	340.09
ALogP:	-0.4445
MLogP:	2.89
XLogP:	2.91
# Rotatable Bonds:	8
Polar Surface Area:	96.22
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	25

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