NPASS Natural Product

Natural Product: NPC182758

Natural Product ID:	NPC182758
Common Name:	Motualevic Acid A
IUPAC Name:	2-[[(2E)-14,14-dibromotetradeca-2,13-dienoyl]amino]acetic acid
Synonyms:
Molecular Formula:	C16H25Br2NO3
Standard InCHIKey:	ZLIHRGDEFDFVOK-ZRDIBKRKSA-N
Standard InCHI:	InChI=1S/C16H25Br2NO3/c17-14(18)11-9-7-5-3-1-2-4-6-8-10-12-15(20)19-13-16(21)22/h10-12H,1-9,13H2,(H,19,20)(H,21,22)/b12-10+
Canonical SMILES:	OC(=NCC(=O)O)/C=C/CCCCCCCCCC=C(Br)Br
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30959	Siliquariaspongia	NA	NA	NA				PMID[19191563]

Biological Activity

Activity Type	# Activity
MIC	4
Others	5

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8	mm	20538459
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IZ	=	8	mm	20538459
NPT1605	Organism	Enterococcus	Enterococcus	IZ	=	8	mm	20538459
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	11	ug/ml	20538459
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	9.3	ug/ml	20538459
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	9.3	ug/ml	20538459
NPT1605	Organism	Enterococcus	Enterococcus	MIC	=	12	ug/ml	20538459

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 NPC182758 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	33
0.1-0.2	901
0.2-0.3	19126
0.3-0.4	8805
0.4-0.5	1674
0.5-0.6	282
0.6-0.7	51
0.7-0.8	17
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7576	Intermediate Similarity	NPC316674
0.7536	Intermediate Similarity	NPC249713
0.75	Intermediate Similarity	NPC325734
0.7385	Intermediate Similarity	NPC312826
0.7302	Intermediate Similarity	NPC273023
0.7188	Intermediate Similarity	NPC306420
0.7188	Intermediate Similarity	NPC104138
0.7188	Intermediate Similarity	NPC261158
0.7188	Intermediate Similarity	NPC24216
0.7183	Intermediate Similarity	NPC280065
0.7183	Intermediate Similarity	NPC45060
0.7164	Intermediate Similarity	NPC273614
0.7059	Intermediate Similarity	NPC77891
0.7031	Intermediate Similarity	NPC297020
0.7015	Intermediate Similarity	NPC6795
0.7015	Intermediate Similarity	NPC130807
0.7	Intermediate Similarity	NPC187315
0.6984	Remote Similarity	NPC303672
0.6875	Remote Similarity	NPC14234
0.6875	Remote Similarity	NPC132669
0.6875	Remote Similarity	NPC184014
0.6875	Remote Similarity	NPC246519
0.6875	Remote Similarity	NPC269800
0.6875	Remote Similarity	NPC44193
0.6825	Remote Similarity	NPC195986
0.6667	Remote Similarity	NPC54542
0.6667	Remote Similarity	NPC243539
0.6667	Remote Similarity	NPC304223
0.6667	Remote Similarity	NPC145032
0.6667	Remote Similarity	NPC267340
0.6667	Remote Similarity	NPC29468
0.662	Remote Similarity	NPC477525
0.6615	Remote Similarity	NPC13011
0.6615	Remote Similarity	NPC124382
0.6522	Remote Similarity	NPC309877
0.6515	Remote Similarity	NPC471991
0.6515	Remote Similarity	NPC471992
0.6508	Remote Similarity	NPC267692
0.6508	Remote Similarity	NPC307435
0.6462	Remote Similarity	NPC119655
0.6377	Remote Similarity	NPC329003
0.6377	Remote Similarity	NPC326524
0.6377	Remote Similarity	NPC150505
0.6377	Remote Similarity	NPC325550
0.6377	Remote Similarity	NPC74617
0.6364	Remote Similarity	NPC163912
0.6364	Remote Similarity	NPC305288
0.6364	Remote Similarity	NPC167759
0.6364	Remote Similarity	NPC56028
0.6338	Remote Similarity	NPC471023
0.6324	Remote Similarity	NPC245650
0.6269	Remote Similarity	NPC242930
0.6267	Remote Similarity	NPC471022
0.6267	Remote Similarity	NPC103712
0.6267	Remote Similarity	NPC291196
0.6232	Remote Similarity	NPC321030
0.6197	Remote Similarity	NPC324077
0.6176	Remote Similarity	NPC477049
0.6133	Remote Similarity	NPC474812
0.6119	Remote Similarity	NPC123669
0.6066	Remote Similarity	NPC86121
0.6049	Remote Similarity	NPC474833
0.6029	Remote Similarity	NPC474513
0.6029	Remote Similarity	NPC146551
0.6029	Remote Similarity	NPC470963
0.6029	Remote Similarity	NPC45626
0.6027	Remote Similarity	NPC253468
0.6027	Remote Similarity	NPC235311
0.5952	Remote Similarity	NPC474312
0.5949	Remote Similarity	NPC288086
0.5942	Remote Similarity	NPC4881
0.5942	Remote Similarity	NPC311648
0.5942	Remote Similarity	NPC470964
0.5875	Remote Similarity	NPC476923
0.5867	Remote Similarity	NPC129995
0.5867	Remote Similarity	NPC315141
0.5857	Remote Similarity	NPC48968
0.5857	Remote Similarity	NPC594
0.5821	Remote Similarity	NPC129458
0.5797	Remote Similarity	NPC152668
0.5783	Remote Similarity	NPC157173
0.5781	Remote Similarity	NPC308331
0.5758	Remote Similarity	NPC329181
0.5758	Remote Similarity	NPC59051
0.5758	Remote Similarity	NPC319110
0.5735	Remote Similarity	NPC225066
0.5735	Remote Similarity	NPC10081
0.5714	Remote Similarity	NPC304079
0.5714	Remote Similarity	NPC6963
0.5676	Remote Similarity	NPC55068
0.5672	Remote Similarity	NPC261571
0.5638	Remote Similarity	NPC175614
0.5634	Remote Similarity	NPC265551
0.5634	Remote Similarity	NPC44542
0.5634	Remote Similarity	NPC212730
0.5625	Remote Similarity	NPC314678
0.5618	Remote Similarity	NPC472614
0.5616	Remote Similarity	NPC471278

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC182758 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	34
0.1-0.2	554
0.2-0.3	5986
0.3-0.4	2324
0.4-0.5	231
0.5-0.6	32
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5846	Remote Similarity	NPD4220	Pre-registration
0.5676	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD39	Approved

Structure

CID182758 OpenBabel06191715562D 22 21 0 0 0 0 0 0 0 0999 V2000 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 1.7321 2.0000 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 1.7321 -1.0000 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 -0.8660 0.5000 0.0000 C 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 2.5981 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 N 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 -1.7321 -0.0000 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 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 14 2 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 3 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	25242622
ChEMBL	CHEMBL1171537
ZINC

Physicochemical Properties

Molecular Weight:	437.02
ALogP:	-6.00E-04
MLogP:	2.56
XLogP:	6.011
# Rotatable Bonds:	17
Polar Surface Area:	69.89
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	22

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