NPASS Natural Product

Natural Product: NPC237219

Natural Product ID:	NPC237219
Common Name:	Aerucyclamide C
IUPAC Name:
Synonyms:	Aerucyclamide C
Molecular Formula:	C24H32N6O5S
Standard InCHIKey:	MQIAICAGVFTAAN-ZIYJYRAWSA-N
Standard InCHI:	InChI=1S/C24H32N6O5S/c1-7-11(4)17-24-27-15(9-36-24)20(32)25-12(5)22-30-18(13(6)35-22)21(33)28-16(10(2)3)23-26-14(8-34-23)19(31)29-17/h8-13,16-18H,7H2,1-6H3,(H,25,32)(H,28,33)(H,29,31)/t11-,12-,13+,16-,17+,18-/m0/s1
Canonical SMILES:	CC[C@@H]([C@H]1N=C(O)c2coc(n2)[C@@H](N=C(O)[C@H]2N=C([C@@H](N=C(c3nc1sc3)O)C)O[C@@H]2C)C(C)C)C
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
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria				PMID[18973386]

Biological Activity

Activity Type	# Activity
IC50	3
Others	1

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	2300	nM	20055495
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	106000	nM	16168652
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	9200	nM	18194870
NPT6519	Organism	Thamnocephalus platyurus	Thamnocephalus platyurus	LC50	=	70500	nM	18359631

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 NPC237219 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	176
0.1-0.2	7004
0.2-0.3	20056
0.3-0.4	3291
0.4-0.5	209
0.5-0.6	115
0.6-0.7	22
0.7-0.8	9
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC50274
0.8861	High Similarity	NPC256912
0.8553	High Similarity	NPC222391
0.8509	High Similarity	NPC34319
0.8428	Intermediate Similarity	NPC110129
0.8428	Intermediate Similarity	NPC201014
0.8239	Intermediate Similarity	NPC217981
0.7905	Intermediate Similarity	NPC89592
0.7755	Intermediate Similarity	NPC51692
0.7582	Intermediate Similarity	NPC74917
0.7532	Intermediate Similarity	NPC120917
0.7432	Intermediate Similarity	NPC135558
0.74	Intermediate Similarity	NPC267605
0.7391	Intermediate Similarity	NPC475390
0.7297	Intermediate Similarity	NPC214375
0.7125	Intermediate Similarity	NPC103268
0.6989	Remote Similarity	NPC164006
0.6796	Remote Similarity	NPC132662
0.6782	Remote Similarity	NPC235866
0.645	Remote Similarity	NPC469801
0.6444	Remote Similarity	NPC475554
0.6369	Remote Similarity	NPC56058
0.6369	Remote Similarity	NPC522
0.6359	Remote Similarity	NPC134480
0.6324	Remote Similarity	NPC473704
0.6257	Remote Similarity	NPC476080
0.6257	Remote Similarity	NPC475534
0.6257	Remote Similarity	NPC161242
0.6223	Remote Similarity	NPC475330
0.6222	Remote Similarity	NPC216720
0.619	Remote Similarity	NPC174652
0.619	Remote Similarity	NPC25316
0.619	Remote Similarity	NPC229160
0.619	Remote Similarity	NPC263485
0.6188	Remote Similarity	NPC210424
0.6089	Remote Similarity	NPC315872
0.602	Remote Similarity	NPC329961
0.602	Remote Similarity	NPC122427
0.5966	Remote Similarity	NPC319751
0.596	Remote Similarity	NPC165538
0.5936	Remote Similarity	NPC24990
0.5911	Remote Similarity	NPC476829
0.5904	Remote Similarity	NPC476103
0.5876	Remote Similarity	NPC314523
0.5876	Remote Similarity	NPC58001
0.5866	Remote Similarity	NPC119481
0.5816	Remote Similarity	NPC96016
0.581	Remote Similarity	NPC473398
0.5762	Remote Similarity	NPC475350
0.5762	Remote Similarity	NPC145178
0.5762	Remote Similarity	NPC14877
0.5697	Remote Similarity	NPC315411
0.5694	Remote Similarity	NPC49195
0.5684	Remote Similarity	NPC30527
0.5681	Remote Similarity	NPC251036
0.5631	Remote Similarity	NPC107458
0.5631	Remote Similarity	NPC295653

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC237219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	124
0.1-0.2	1226
0.2-0.3	4323
0.3-0.4	3125
0.4-0.5	341
0.5-0.6	20
0.6-0.7	2
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
0.6313	Remote Similarity	NPD7896	Approved
0.6089	Remote Similarity	NPD6444	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD9579	Approved
0.5904	Remote Similarity	NPD2623	Phase 1
0.5871	Remote Similarity	NPD6347	Phase 2
0.5803	Remote Similarity	NPD2957	Phase 2
0.5764	Remote Similarity	NPD7490	Discontinued
0.5629	Remote Similarity	NPD2225	Clinical (unspecified phase)

Structure

NPC237219 OpenBabel07101719512D 36 39 0 0 1 0 0 0 0 0999 V2000 -1.7002 -1.5960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2605 5.8217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9662 5.5209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0586 0.6744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3247 -1.1352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3397 2.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4662 -0.9532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.7169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8529 -0.4924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0265 5.1789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2926 0.0316 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5586 -0.4924 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2057 1.8508 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8529 3.2093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8529 -1.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8529 4.1941 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3529 0.3736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0586 2.3432 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3529 2.3432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8529 -1.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5586 3.2093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 0.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8529 4.1941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8529 -0.4924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7926 -1.1352 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0868 3.8521 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0868 -1.1352 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7926 3.8521 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5265 1.3584 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2323 1.3584 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2926 2.6853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0265 -2.4620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3247 3.8521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8529 3.2093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2057 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 10 1 0 0 0 0 3 10 1 0 0 0 0 7 11 1 0 0 0 0 8 14 2 0 0 0 0 8 34 1 0 0 0 0 9 15 2 0 0 0 0 9 36 1 0 0 0 0 11 4 1 6 0 0 0 12 5 1 6 0 0 0 12 22 1 0 0 0 0 12 25 1 0 0 0 0 13 6 1 6 0 0 0 13 18 1 0 0 0 0 13 35 1 0 0 0 0 14 19 1 0 0 0 0 14 26 1 0 0 0 0 15 20 1 0 0 0 0 15 27 1 0 0 0 0 16 10 1 6 0 0 0 16 23 1 0 0 0 0 16 28 1 0 0 0 0 17 11 1 1 0 0 0 17 24 1 0 0 0 0 17 29 1 0 0 0 0 18 21 1 1 0 0 0 18 30 1 0 0 0 0 19 29 2 3 0 0 0 19 31 1 0 0 0 0 20 25 2 3 0 0 0 20 32 1 0 0 0 0 21 28 2 3 0 0 0 21 33 1 0 0 0 0 22 30 2 0 0 0 0 22 35 1 0 0 0 0 23 26 2 0 0 0 0 23 34 1 0 0 0 0 24 27 2 0 0 0 0 24 36 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	25156431
ChEMBL	CHEMBL575440
ZINC

Physicochemical Properties

Molecular Weight:	516.22
ALogP:	0.1414
MLogP:	2.78
XLogP:	3.074
# Rotatable Bonds:	12
Polar Surface Area:	186.52
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	36

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