NPASS Natural Product

Natural Product: NPC89592

Natural Product ID:	NPC89592
Common Name:	Aerucyclamide B
IUPAC Name:
Synonyms:
Molecular Formula:	C24H32N6O4S2
Standard InCHIKey:	JFWABYMXSVHLEW-ZUDVWZRRSA-N
Standard InCHI:	InChI=1S/C24H32N6O4S2/c1-6-11(3)17-23-30-19(13(5)34-23)22(33)25-8-16-26-14(9-35-16)20(31)29-18(12(4)7-2)24-27-15(10-36-24)21(32)28-17/h9-13,17-19H,6-8H2,1-5H3,(H,25,33)(H,28,32)(H,29,31)/t11-,12-,13+,17-,18+,19-/m0/s1
Canonical SMILES:	CC[C@@H]([C@@H]1N=C(O)c2csc(n2)[C@H](N=C(O)c2nc(CN=C([C@H]3N=C1O[C@@H]3C)O)sc2)[C@H](CC)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[18558743]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria				PMID[18973386]

Biological Activity

Activity Type	# Activity
IC50	4
Others	1

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6519	Organism	Thamnocephalus platyurus	Thamnocephalus platyurus	LC50	=	33800	nM	17890094
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	700	nM	19738019
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	700	nM	11087604
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	15900	nM	11087604
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	120000	nM	20055495

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 NPC89592 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	105
0.1-0.2	10401
0.2-0.3	16503
0.3-0.4	3461
0.4-0.5	300
0.5-0.6	72
0.6-0.7	23
0.7-0.8	18
0.8-0.85	0
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9664	High Similarity	NPC51692
0.9516	High Similarity	NPC74917
0.9339	High Similarity	NPC267605
0.9286	High Similarity	NPC120917
0.9091	High Similarity	NPC135558
0.9083	High Similarity	NPC214375
0.7943	Intermediate Similarity	NPC475390
0.7905	Intermediate Similarity	NPC237219
0.777	Intermediate Similarity	NPC103268
0.7532	Intermediate Similarity	NPC161242
0.745	Intermediate Similarity	NPC50274
0.7438	Intermediate Similarity	NPC229160
0.7438	Intermediate Similarity	NPC25316
0.7438	Intermediate Similarity	NPC263485
0.7436	Intermediate Similarity	NPC164006
0.7421	Intermediate Similarity	NPC476080
0.7421	Intermediate Similarity	NPC475534
0.7375	Intermediate Similarity	NPC475330
0.7329	Intermediate Similarity	NPC174652
0.7205	Intermediate Similarity	NPC132662
0.7192	Intermediate Similarity	NPC469801
0.7152	Intermediate Similarity	NPC24990
0.7044	Intermediate Similarity	NPC34319
0.7	Intermediate Similarity	NPC476103
0.6962	Remote Similarity	NPC222391
0.6943	Remote Similarity	NPC522
0.6943	Remote Similarity	NPC56058
0.6943	Remote Similarity	NPC201014
0.6943	Remote Similarity	NPC110129
0.6937	Remote Similarity	NPC256912
0.6821	Remote Similarity	NPC319751
0.6813	Remote Similarity	NPC475554
0.6752	Remote Similarity	NPC217981
0.6732	Remote Similarity	NPC473398
0.6707	Remote Similarity	NPC134480
0.6688	Remote Similarity	NPC119481
0.6667	Remote Similarity	NPC473704
0.6562	Remote Similarity	NPC216720
0.6522	Remote Similarity	NPC210424
0.6215	Remote Similarity	NPC122427
0.6215	Remote Similarity	NPC329961
0.6145	Remote Similarity	NPC165538
0.6131	Remote Similarity	NPC470146
0.6131	Remote Similarity	NPC97078
0.6131	Remote Similarity	NPC101980
0.608	Remote Similarity	NPC96016
0.6	Remote Similarity	NPC315252
0.5854	Remote Similarity	NPC14101
0.581	Remote Similarity	NPC49051
0.5772	Remote Similarity	NPC475568
0.5743	Remote Similarity	NPC137705
0.5705	Remote Similarity	NPC474070
0.567	Remote Similarity	NPC14877
0.567	Remote Similarity	NPC145178
0.567	Remote Similarity	NPC475350
0.5658	Remote Similarity	NPC475604
0.564	Remote Similarity	NPC473886
0.56	Remote Similarity	NPC235866

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC89592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	95
0.1-0.2	1085
0.2-0.3	4260
0.3-0.4	3301
0.4-0.5	388
0.5-0.6	31
0.6-0.7	0
0.7-0.8	1
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
0.7313	Intermediate Similarity	NPD9579	Approved
0.5976	Remote Similarity	NPD6915	Approved
0.5959	Remote Similarity	NPD6121	Clinical (unspecified phase)
0.5886	Remote Similarity	NPD2957	Phase 2
0.5811	Remote Similarity	NPD2225	Clinical (unspecified phase)

Structure

NPC89592 OpenBabel07101718282D 36 39 0 0 1 0 0 0 0 0999 V2000 -4.9367 -0.0970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1909 -0.9614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0837 -0.8496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1358 1.0379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0422 2.5751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1475 0.5172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3114 -0.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5078 3.4470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3745 1.9810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5054 -0.2217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2211 0.1409 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2839 0.5142 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1762 2.0751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4044 2.6082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9502 0.1052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9502 3.4932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4319 0.7551 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4044 0.9901 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6982 2.3511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5861 2.0789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5078 0.1514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4319 2.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6982 1.2472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0607 0.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0202 3.2222 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0486 3.5427 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4077 0.2425 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0202 0.3761 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5861 1.5194 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7903 1.7992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5725 2.2435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7533 -0.8180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2211 3.4574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1762 1.5232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2116 2.5280 0.0000 S 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 6 1 0 0 0 0 2 7 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 16 1 0 0 0 0 8 25 1 0 0 0 0 9 14 2 0 0 0 0 9 35 1 0 0 0 0 10 15 2 0 0 0 0 10 36 1 0 0 0 0 11 3 1 1 0 0 0 12 4 1 1 0 0 0 13 5 1 6 0 0 0 13 19 1 0 0 0 0 13 34 1 0 0 0 0 14 20 1 0 0 0 0 14 26 1 0 0 0 0 15 21 1 0 0 0 0 15 27 1 0 0 0 0 16 26 2 0 0 0 0 16 35 1 0 0 0 0 17 11 1 1 0 0 0 17 23 1 0 0 0 0 17 28 1 0 0 0 0 18 12 1 6 0 0 0 18 24 1 0 0 0 0 18 29 1 0 0 0 0 19 22 1 1 0 0 0 19 30 1 0 0 0 0 20 29 2 3 0 0 0 20 31 1 0 0 0 0 21 28 2 3 0 0 0 21 32 1 0 0 0 0 22 25 2 3 0 0 0 22 33 1 0 0 0 0 23 30 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	24970831
ChEMBL	CHEMBL520774
ZINC

Physicochemical Properties

Molecular Weight:	532.19
ALogP:	0.1085
MLogP:	2.78
XLogP:	3.718
# Rotatable Bonds:	12
Polar Surface Area:	201.62
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	36

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