NPASS Natural Product

Natural Product: NPC197766

Natural Product ID:	NPC197766
Common Name:	Z/E-Synoilide B
IUPAC Name:	dimethyl 2-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)but-2-enedioate
Synonyms:	Z/E-Synoilide B
Molecular Formula:	C19H13Br3O7
Standard InCHIKey:	GMHLSOYTFNFLNQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H13Br3O7/c1-28-18(26)14(8-3-4-13(23)10(20)5-8)15(19(27)29-2)16(24)9-6-11(21)17(25)12(22)7-9/h3-7,23,25H,1-2H3
Canonical SMILES:	COC(=O)C(=C(c1ccc(c(c1)Br)O)C(=O)OC)C(=O)c1cc(Br)c(c(c1)Br)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
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota				PMID[23145909]

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Biological Activity

Activity Type	# Activity
IC50	3
MIC	6
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Organism	4
Others	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	47600	nM	10.1021/np50094a030
NPT111	Cell Line	K562	Homo sapiens	LC50	=	49700	nM	25322455
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	100	ug/ml	11678669
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100	ug/ml	15730238
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100	ug/ml	25981689
NPT2	Others	Unspecified		IC50	=	145400	nM	11429990
NPT2	Others	Unspecified		MIC	>	100	ug/ml	24467317
NPT2	Others	Unspecified		MIC	>	100	ug/ml	12880316
NPT2	Others	Unspecified		IC50	>	120000	nM	16506833
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	>	100	ug/ml	12762807

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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 NPC197766 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	227
0.1-0.2	1282
0.2-0.3	2953
0.3-0.4	7610
0.4-0.5	6016
0.5-0.6	5889
0.6-0.7	6280
0.7-0.8	607
0.8-0.85	16
0.85-0.9	1
0.9-0.95	5
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.7285	Intermediate Similarity	NPC303644
0.7285	Intermediate Similarity	NPC250266
0.7286	Intermediate Similarity	NPC159525
0.7286	Intermediate Similarity	NPC72977
0.7289	Intermediate Similarity	NPC470566

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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 NPC197766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	991
0.2-0.3	1423
0.3-0.4	2776
0.4-0.5	2279
0.5-0.6	1127
0.6-0.7	287
0.7-0.8	24
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6234	Remote Similarity	NPD5736	Approved
0.6235	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD4626	Approved
0.6242	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2979	Phase 3

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Structure

NPC197766 OpenBabel07101718282D 29 30 0 0 0 0 0 0 0 0999 V2000 5.1962 -4.0000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 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 1.7321 -0.0000 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 5.1962 -1.0000 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 6.9282 -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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 3.4641 -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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 29 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 7 12 2 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 3 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 24 2 0 0 0 0 17 25 1 0 0 0 0 18 26 2 0 0 0 0 18 28 1 0 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	73352811
ChEMBL	CHEMBL2204159
ZINC

Physicochemical Properties

Molecular Weight:	589.82
ALogP:	1.581
MLogP:	2.45
XLogP:	4.384
# Rotatable Bonds:	14
Polar Surface Area:	110.13
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	29

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