NPASS Natural Product

Natural Product: NPC178919

Natural Product ID:	NPC178919
Common Name:	Enniatin B1
IUPAC Name:	(3S,6R,9S,12R,15S,18R)-3-[(2S)-butan-2-yl]-4,10,16-trimethyl-6,9,12,15,18-penta(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Synonyms:	Enniatin B1
Molecular Formula:	C34H59N3O9
Standard InCHIKey:	UQCSETXJXJTMKO-UMURLBKASA-N
Standard InCHI:	InChI=1S/C34H59N3O9/c1-16-22(12)25-34(43)46-27(20(8)9)30(39)36(14)23(17(2)3)32(41)44-26(19(6)7)29(38)35(13)24(18(4)5)33(42)45-28(21(10)11)31(40)37(25)15/h17-28H,16H2,1-15H3/t22-,23-,24-,25-,26+,27+,28+/m0/s1
Canonical SMILES:	CC[C@@H]([C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N1C)C(C)C)C(C)C)C)C(C)C)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	UNPD*
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	UNPD*
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	PMID[24175613]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	UNPD*
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	PMID[16562855]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	UNPD*
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	UNPD*
NPO2993	Nototodarus sloanii	Species	Ommastrephidae	Eukaryota	UNPD*
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	UNPD*
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	UNPD*
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	UNPD*
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	UNPD*
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	UNPD*
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	UNPD*
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	UNPD*
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	UNPD*
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	UNPD*
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	UNPD*
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	UNPD*
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	UNPD*
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	UNPD*
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	UNPD*
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	UNPD*
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	UNPD*
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	UNPD*
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	UNPD*
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	UNPD*
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	UNPD*
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	UNPD*
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	UNPD*
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	UNPD*
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	UNPD*
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	UNPD*
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	UNPD*
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	UNPD*
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	UNPD*
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	UNPD*
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	UNPD*

Biological Activity

Activity Type	# Activity
IC50	3
MIC	10
Others	1

Activity Type	# Activity
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	=	75	ug/ml	15165149
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	Activity	=	25	ug/ml	15165149
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	2	ug/ml	16562855
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	6.25	ug/ml	16562855
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	9	ug/ml	16562855
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	25	ug/ml	16562855
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	15	ug/ml	16562855
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	64	ug/ml	24175613
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64	ug/ml	24175613
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	8	ug/ml	24175613
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	4	ug/ml	24175613
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8	ug/ml	24175613
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	MIC	=	16	ug/ml	24175613

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 NPC178919 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	73
0.1-0.2	7956
0.2-0.3	14044
0.3-0.4	7662
0.4-0.5	912
0.5-0.6	187
0.6-0.7	37
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC263281
0.9437	High Similarity	NPC477145
0.9437	High Similarity	NPC473741
0.9403	High Similarity	NPC212866
0.9403	High Similarity	NPC29598
0.9254	High Similarity	NPC10716
0.7975	Intermediate Similarity	NPC246005
0.7471	Intermediate Similarity	NPC62263
0.7471	Intermediate Similarity	NPC471098
0.7471	Intermediate Similarity	NPC173763
0.7363	Intermediate Similarity	NPC220234
0.7356	Intermediate Similarity	NPC476019
0.7356	Intermediate Similarity	NPC474576
0.7241	Intermediate Similarity	NPC474593
0.7241	Intermediate Similarity	NPC475801
0.7128	Intermediate Similarity	NPC124554
0.7128	Intermediate Similarity	NPC301148
0.7128	Intermediate Similarity	NPC5864
0.6989	Remote Similarity	NPC475440
0.6979	Remote Similarity	NPC124549
0.6979	Remote Similarity	NPC323720
0.6875	Remote Similarity	NPC198344
0.6771	Remote Similarity	NPC475149
0.6771	Remote Similarity	NPC471097
0.6768	Remote Similarity	NPC171734
0.6768	Remote Similarity	NPC67009
0.6742	Remote Similarity	NPC322966
0.6735	Remote Similarity	NPC475637
0.6706	Remote Similarity	NPC84128
0.6706	Remote Similarity	NPC53858
0.6562	Remote Similarity	NPC13175
0.6562	Remote Similarity	NPC475791
0.6458	Remote Similarity	NPC475758
0.642	Remote Similarity	NPC141325
0.6375	Remote Similarity	NPC478256
0.6344	Remote Similarity	NPC315237
0.6341	Remote Similarity	NPC138435
0.625	Remote Similarity	NPC473597
0.6237	Remote Similarity	NPC477538
0.619	Remote Similarity	NPC476130
0.619	Remote Similarity	NPC476324
0.6173	Remote Similarity	NPC476291
0.6092	Remote Similarity	NPC476137
0.6092	Remote Similarity	NPC476156
0.6092	Remote Similarity	NPC476117
0.6092	Remote Similarity	NPC476243
0.6076	Remote Similarity	NPC326651
0.6076	Remote Similarity	NPC325117
0.6076	Remote Similarity	NPC322319
0.6071	Remote Similarity	NPC86064
0.6071	Remote Similarity	NPC327272
0.6049	Remote Similarity	NPC193280
0.6049	Remote Similarity	NPC314273
0.6023	Remote Similarity	NPC476302
0.6	Remote Similarity	NPC188785
0.5977	Remote Similarity	NPC31756
0.5976	Remote Similarity	NPC476285
0.5972	Remote Similarity	NPC325180
0.5972	Remote Similarity	NPC35816
0.5952	Remote Similarity	NPC43219
0.5952	Remote Similarity	NPC476248
0.5926	Remote Similarity	NPC472536
0.5926	Remote Similarity	NPC103391
0.5893	Remote Similarity	NPC477238
0.5862	Remote Similarity	NPC233108
0.5833	Remote Similarity	NPC63191
0.5833	Remote Similarity	NPC471202
0.5824	Remote Similarity	NPC95478
0.5824	Remote Similarity	NPC145748
0.5824	Remote Similarity	NPC155670
0.5824	Remote Similarity	NPC472351
0.5765	Remote Similarity	NPC208657
0.5761	Remote Similarity	NPC227051
0.5747	Remote Similarity	NPC472594
0.5714	Remote Similarity	NPC477237
0.5714	Remote Similarity	NPC235078
0.5667	Remote Similarity	NPC23984
0.5667	Remote Similarity	NPC470783
0.5663	Remote Similarity	NPC224700
0.5663	Remote Similarity	NPC322274
0.5663	Remote Similarity	NPC320663
0.563	Remote Similarity	NPC152850
0.563	Remote Similarity	NPC89923
0.563	Remote Similarity	NPC71933
0.563	Remote Similarity	NPC239990
0.563	Remote Similarity	NPC105114
0.5625	Remote Similarity	NPC477729
0.56	Remote Similarity	NPC47076
0.56	Remote Similarity	NPC134504

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC178919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	76
0.1-0.2	2320
0.2-0.3	4625
0.3-0.4	1622
0.4-0.5	393
0.5-0.6	111
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9403	High Similarity	NPD7840	Approved
0.6429	Remote Similarity	NPD8144	Approved
0.6429	Remote Similarity	NPD8143	Approved
0.6375	Remote Similarity	NPD2697	Approved
0.6375	Remote Similarity	NPD2695	Approved
0.6375	Remote Similarity	NPD2696	Approved
0.6375	Remote Similarity	NPD2694	Approved
0.622	Remote Similarity	NPD6704	Discontinued
0.6186	Remote Similarity	NPD3713	Approved
0.6186	Remote Similarity	NPD3714	Approved
0.6186	Remote Similarity	NPD3715	Approved
0.6164	Remote Similarity	NPD4281	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD7759	Phase 2
0.6044	Remote Similarity	NPD7760	Phase 2
0.5976	Remote Similarity	NPD2220	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD9660	Approved
0.5859	Remote Similarity	NPD8038	Phase 2
0.5854	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD7763	Phase 2
0.5843	Remote Similarity	NPD7762	Phase 2
0.5814	Remote Similarity	NPD1452	Discontinued
0.5784	Remote Similarity	NPD8301	Approved
0.5784	Remote Similarity	NPD8300	Approved
0.5783	Remote Similarity	NPD3726	Approved
0.5783	Remote Similarity	NPD3725	Approved
0.5783	Remote Similarity	NPD9649	Approved
0.5753	Remote Similarity	NPD9202	Approved
0.575	Remote Similarity	NPD9648	Approved
0.5747	Remote Similarity	NPD2689	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD9659	Approved
0.5729	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7535	Discontinued
0.5714	Remote Similarity	NPD1458	Approved
0.5714	Remote Similarity	NPD1459	Approved
0.5672	Remote Similarity	NPD9456	Approved
0.5672	Remote Similarity	NPD9457	Approved
0.5663	Remote Similarity	NPD8278	Approved
0.5657	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD11	Approved
0.5632	Remote Similarity	NPD376	Approved
0.5632	Remote Similarity	NPD1453	Phase 1
0.5616	Remote Similarity	NPD2693	Approved
0.5616	Remote Similarity	NPD2692	Approved
0.5616	Remote Similarity	NPD9203	Approved

Structure

CID178919 OpenBabel06191715552D 46 46 0 0 1 0 0 0 0 0999 V2000 3.2964 -0.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3293 0.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0024 1.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5349 -6.6172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1625 -6.0248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0133 -3.8191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3141 -2.1133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1668 2.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4608 1.6133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6276 -5.0039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3008 -6.1172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6124 -2.2981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3445 -5.1775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1777 1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 -2.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3116 -0.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3445 0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1777 -5.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6713 -2.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5240 1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 -5.1775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 -1.5321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7017 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8356 -4.9115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9848 -1.7057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6865 -2.7057 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -4.4115 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3445 -3.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 0.6736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 -3.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3445 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 -5.0851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7017 -4.4115 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9848 -2.7057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -4.1454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 1.6736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5088 -4.1454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -0.2660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 -6.0851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5088 -0.2660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6865 -1.7057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.9115 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 16 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 21 1 0 0 0 0 13 35 1 0 0 0 0 14 36 1 0 0 0 0 15 37 1 0 0 0 0 16 22 1 0 0 0 0 22 12 1 6 0 0 0 23 17 1 6 0 0 0 23 32 1 0 0 0 0 23 36 1 0 0 0 0 24 18 1 6 0 0 0 24 33 1 0 0 0 0 24 35 1 0 0 0 0 25 22 1 6 0 0 0 25 34 1 0 0 0 0 25 37 1 0 0 0 0 26 19 1 1 0 0 0 26 29 1 0 0 0 0 26 44 1 0 0 0 0 27 20 1 1 0 0 0 27 30 1 0 0 0 0 27 46 1 0 0 0 0 28 21 1 1 0 0 0 28 31 1 0 0 0 0 28 45 1 0 0 0 0 29 35 1 0 0 0 0 29 38 2 0 0 0 0 30 36 1 0 0 0 0 30 39 2 0 0 0 0 31 37 1 0 0 0 0 31 40 2 0 0 0 0 32 41 2 0 0 0 0 32 44 1 0 0 0 0 33 42 2 0 0 0 0 33 45 1 0 0 0 0 34 43 2 0 0 0 0 34 46 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11262300
ChEMBL	CHEMBL446318
ZINC

Physicochemical Properties

Molecular Weight:	653.43
ALogP:	-0.0522
MLogP:	3.88
XLogP:	4.706
# Rotatable Bonds:	22
Polar Surface Area:	139.83
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	46

Download Data

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General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs