NPASS Natural Product

Natural Product: NPC473955

Natural Product ID:	NPC473955
Common Name:	Cyanocycline B
IUPAC Name:
Synonyms:
Molecular Formula:	C21H24N4O5
Standard InCHIKey:	UVAIYWZSCCGGSE-VNEJAINRSA-N
Standard InCHI:	InChI=1S/C21H24N4O5/c1-8-18(27)14-13(19(28)20(8)29-2)12(7-26)25-11(6-22)10-5-9-15(23-10)17(25)16(14)24-3-4-30-21(9)24/h9-12,15-17,21,23,26H,3-5,7H2,1-2H3/t9-,10-,11-,12-,15+,16+,17+,21+/m1/s1
Canonical SMILES:	OC[C@H]1N2[C@H](C#N)[C@H]3C[C@@H]4[C@@H]([C@H]2[C@H](C2=C1C(=O)C(=C(C2=O)C)OC)N1[C@H]4OCC1)N3
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
NPO1930	Streptomyces lusitanus	Species	Streptomycetaceae	Bacteria				PMID[8229009]

Biological Activity

Activity Type	# Activity
MIC	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	0.063	ug/ml	Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	=	0.5	ug/ml	PubChem BioAssay data set
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.016	ug/ml	PubChem BioAssay data set
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	0.25	ug/ml	24673739
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	0.031	ug/ml	20008780
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	1	ug/ml	18458127
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.25	ug/ml	PubChem BioAssay data set

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 NPC473955 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	98
0.1-0.2	779
0.2-0.3	6294
0.3-0.4	18380
0.4-0.5	4984
0.5-0.6	318
0.6-0.7	28
0.7-0.8	5
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9606	High Similarity	NPC475987
0.9606	High Similarity	NPC313348
0.8661	High Similarity	NPC13351
0.7273	Intermediate Similarity	NPC315011
0.7273	Intermediate Similarity	NPC161644
0.7174	Intermediate Similarity	NPC315110
0.7162	Intermediate Similarity	NPC25025
0.7014	Intermediate Similarity	NPC97861
0.6892	Remote Similarity	NPC239252
0.6892	Remote Similarity	NPC473703
0.669	Remote Similarity	NPC139867
0.6642	Remote Similarity	NPC87919
0.6423	Remote Similarity	NPC176773
0.6325	Remote Similarity	NPC319334
0.6325	Remote Similarity	NPC327517
0.6325	Remote Similarity	NPC322372
0.6309	Remote Similarity	NPC262880
0.6309	Remote Similarity	NPC247902
0.6242	Remote Similarity	NPC309525
0.6184	Remote Similarity	NPC478139
0.6165	Remote Similarity	NPC470382
0.6165	Remote Similarity	NPC119225
0.6165	Remote Similarity	NPC476261
0.6165	Remote Similarity	NPC471635
0.6165	Remote Similarity	NPC25033
0.6144	Remote Similarity	NPC120335
0.6131	Remote Similarity	NPC321485
0.6131	Remote Similarity	NPC317377
0.6122	Remote Similarity	NPC11379
0.6096	Remote Similarity	NPC471673
0.6093	Remote Similarity	NPC96010
0.6093	Remote Similarity	NPC317654
0.6014	Remote Similarity	NPC251884
0.6013	Remote Similarity	NPC311244
0.6013	Remote Similarity	NPC324722
0.6013	Remote Similarity	NPC198644
0.5988	Remote Similarity	NPC276822
0.5974	Remote Similarity	NPC41162
0.5974	Remote Similarity	NPC215507
0.5951	Remote Similarity	NPC477519
0.5949	Remote Similarity	NPC45813
0.5862	Remote Similarity	NPC469466
0.5858	Remote Similarity	NPC475342
0.5855	Remote Similarity	NPC477985
0.5855	Remote Similarity	NPC471087
0.5855	Remote Similarity	NPC326386
0.5844	Remote Similarity	NPC173173
0.5839	Remote Similarity	NPC472162
0.5833	Remote Similarity	NPC44200
0.5833	Remote Similarity	NPC12124
0.5833	Remote Similarity	NPC261730
0.5822	Remote Similarity	NPC309731
0.5816	Remote Similarity	NPC133420
0.5806	Remote Similarity	NPC470539
0.5802	Remote Similarity	NPC472161
0.58	Remote Similarity	NPC230849
0.58	Remote Similarity	NPC88190
0.5779	Remote Similarity	NPC476951
0.5772	Remote Similarity	NPC476952
0.5764	Remote Similarity	NPC274895
0.5752	Remote Similarity	NPC477518
0.5743	Remote Similarity	NPC288629
0.5742	Remote Similarity	NPC471086
0.5742	Remote Similarity	NPC478136
0.5734	Remote Similarity	NPC271562
0.5732	Remote Similarity	NPC142761
0.5725	Remote Similarity	NPC472166
0.5714	Remote Similarity	NPC116231
0.5687	Remote Similarity	NPC82129
0.5686	Remote Similarity	NPC293550
0.5686	Remote Similarity	NPC323168
0.5686	Remote Similarity	NPC111162
0.5686	Remote Similarity	NPC477989
0.5686	Remote Similarity	NPC477990
0.5667	Remote Similarity	NPC235625
0.5655	Remote Similarity	NPC469389
0.5655	Remote Similarity	NPC472737
0.5655	Remote Similarity	NPC469388
0.5649	Remote Similarity	NPC469999
0.5649	Remote Similarity	NPC97580
0.5646	Remote Similarity	NPC276995
0.5646	Remote Similarity	NPC76660
0.5634	Remote Similarity	NPC265094
0.5629	Remote Similarity	NPC471261
0.5625	Remote Similarity	NPC471256
0.5616	Remote Similarity	NPC473232
0.5605	Remote Similarity	NPC25327
0.56	Remote Similarity	NPC65045

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473955 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	96
0.1-0.2	368
0.2-0.3	2535
0.3-0.4	4735
0.4-0.5	1332
0.5-0.6	90
0.6-0.7	3
0.7-0.8	2
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
0.7273	Intermediate Similarity	NPD2101	Approved
0.7174	Intermediate Similarity	NPD7196	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1689	Approved
0.662	Remote Similarity	NPD2132	Phase 3
0.6306	Remote Similarity	NPD6077	Discontinued
0.5724	Remote Similarity	NPD8080	Discontinued
0.5658	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5613	Remote Similarity	NPD4816	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD3715	Approved
0.5612	Remote Similarity	NPD3713	Approved
0.5612	Remote Similarity	NPD3714	Approved

Structure

NPC473955 OpenBabel07101719132D 30 35 0 0 1 0 0 0 0 0999 V2000 4.2072 -2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8053 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0670 1.9621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9515 3.5441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 -1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4752 3.2551 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1697 2.9206 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2072 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2072 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3412 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7334 4.1676 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7807 2.9206 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 3.3412 2.1691 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 5.9393 1.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -1.3309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 0.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 -1.3309 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 8 1 0 0 0 0 2 29 1 0 0 0 0 3 4 1 0 0 0 0 3 24 1 0 0 0 0 4 30 1 0 0 0 0 6 11 1 0 0 0 0 6 22 3 0 0 0 0 7 12 1 0 0 0 0 7 26 1 0 0 0 0 8 18 1 0 0 0 0 8 20 2 0 0 0 0 9 5 1 6 0 0 0 9 15 1 0 0 0 0 9 21 1 0 0 0 0 10 5 1 6 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 25 1 1 0 0 0 12 13 1 0 0 0 0 12 25 1 6 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 6 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 25 1 6 0 0 0 18 27 2 0 0 0 0 19 20 1 0 0 0 0 19 28 2 0 0 0 0 20 29 1 0 0 0 0 21 24 1 1 0 0 0 21 30 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44584433
ChEMBL	CHEMBL456090
ZINC

Physicochemical Properties

Molecular Weight:	412.17
ALogP:	-1.3017
MLogP:	2.78
XLogP:	-2.053
# Rotatable Bonds:	5
Polar Surface Area:	115.13
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	30

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