NPASS Natural Product

Natural Product: NPC267605

Natural Product ID:	NPC267605
Common Name:	Aerucyclamide A
IUPAC Name:
Synonyms:
Molecular Formula:	C24H34N6O4S2
Standard InCHIKey:	VJFRQMMMXJJUSM-VZGZUROSSA-N
Standard InCHI:	InChI=1S/C24H34N6O4S2/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/h9,11-13,15,17-19H,6-8,10H2,1-5H3,(H,25,33)(H,28,32)(H,29,31)/t11-,12-,13+,15+,17-,18+,19-/m0/s1
Canonical SMILES:	CC[C@@H]([C@@H]1N=C(O)[C@H]2CSC(=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	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
NPT6519	Organism	Thamnocephalus platyurus	Thamnocephalus platyurus	LC50	=	30500	nM	18197614
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	56300	nM	8691207
NPT839	Cell Line	L6	Rattus norvegicus	IC50	>	168000	nM	8691207
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	5000	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 NPC267605 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	96
0.1-0.2	9880
0.2-0.3	17605
0.3-0.4	3027
0.4-0.5	167
0.5-0.6	69
0.6-0.7	25
0.7-0.8	14
0.8-0.85	0
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9569	High Similarity	NPC135558
0.935	High Similarity	NPC74917
0.9339	High Similarity	NPC89592
0.9167	High Similarity	NPC51692
0.8968	High Similarity	NPC120917
0.8595	High Similarity	NPC214375
0.766	Intermediate Similarity	NPC475390
0.74	Intermediate Similarity	NPC237219
0.7394	Intermediate Similarity	NPC469801
0.7338	Intermediate Similarity	NPC24990
0.7234	Intermediate Similarity	NPC103268
0.7188	Intermediate Similarity	NPC25316
0.7188	Intermediate Similarity	NPC263485
0.7188	Intermediate Similarity	NPC229160
0.7125	Intermediate Similarity	NPC475330
0.7124	Intermediate Similarity	NPC56058
0.7124	Intermediate Similarity	NPC522
0.7081	Intermediate Similarity	NPC174652
0.7067	Intermediate Similarity	NPC50274
0.7063	Intermediate Similarity	NPC161242
0.6962	Remote Similarity	NPC164006
0.6957	Remote Similarity	NPC476080
0.6957	Remote Similarity	NPC475534
0.6879	Remote Similarity	NPC475554
0.6779	Remote Similarity	NPC319751
0.6748	Remote Similarity	NPC132662
0.6689	Remote Similarity	NPC473398
0.6687	Remote Similarity	NPC34319
0.6645	Remote Similarity	NPC119481
0.6604	Remote Similarity	NPC222391
0.6584	Remote Similarity	NPC256912
0.6582	Remote Similarity	NPC201014
0.6582	Remote Similarity	NPC110129
0.6543	Remote Similarity	NPC476103
0.6392	Remote Similarity	NPC217981
0.6265	Remote Similarity	NPC134480
0.6228	Remote Similarity	NPC473704
0.6211	Remote Similarity	NPC216720
0.6173	Remote Similarity	NPC210424
0.6084	Remote Similarity	NPC101980
0.6084	Remote Similarity	NPC97078
0.6084	Remote Similarity	NPC470146
0.608	Remote Similarity	NPC122427
0.608	Remote Similarity	NPC329961
0.6011	Remote Similarity	NPC165538
0.5951	Remote Similarity	NPC315252
0.5931	Remote Similarity	NPC475568
0.5855	Remote Similarity	NPC474070
0.5811	Remote Similarity	NPC475604
0.5793	Remote Similarity	NPC137705
0.5763	Remote Similarity	NPC96016
0.5723	Remote Similarity	NPC231110
0.5723	Remote Similarity	NPC474069
0.5714	Remote Similarity	NPC474068
0.5714	Remote Similarity	NPC82436
0.5714	Remote Similarity	NPC474064
0.5714	Remote Similarity	NPC474103
0.5706	Remote Similarity	NPC154873
0.5689	Remote Similarity	NPC312887
0.5679	Remote Similarity	NPC474079
0.5679	Remote Similarity	NPC474102
0.5679	Remote Similarity	NPC157194
0.5679	Remote Similarity	NPC21449
0.5679	Remote Similarity	NPC474080
0.5679	Remote Similarity	NPC475683
0.5671	Remote Similarity	NPC224609
0.5671	Remote Similarity	NPC268063
0.5644	Remote Similarity	NPC474094
0.5644	Remote Similarity	NPC475737
0.5644	Remote Similarity	NPC474067
0.5644	Remote Similarity	NPC185665
0.5616	Remote Similarity	NPC278902
0.561	Remote Similarity	NPC61667
0.561	Remote Similarity	NPC45576
0.561	Remote Similarity	NPC474515
0.561	Remote Similarity	NPC32583
0.561	Remote Similarity	NPC252616
0.561	Remote Similarity	NPC206724
0.561	Remote Similarity	NPC109498
0.561	Remote Similarity	NPC474090
0.561	Remote Similarity	NPC163147

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC267605 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	92
0.1-0.2	1123
0.2-0.3	4831
0.3-0.4	2813
0.4-0.5	277
0.5-0.6	22
0.6-0.7	2
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
0.7143	Intermediate Similarity	NPD9579	Approved
0.6025	Remote Similarity	NPD6915	Approved
0.6023	Remote Similarity	NPD2957	Phase 2
0.5706	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6907	Phase 2

Structure

NPC267605 OpenBabel07101718232D 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 2 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 36 1 0 0 0 0 11 3 1 6 0 0 0 12 4 1 6 0 0 0 13 5 1 1 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 10 1 1 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 6 0 0 0 17 23 1 0 0 0 0 17 28 1 0 0 0 0 18 12 1 1 0 0 0 18 24 1 0 0 0 0 18 29 1 0 0 0 0 19 22 1 6 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	24970830
ChEMBL	CHEMBL479808
ZINC

Physicochemical Properties

Molecular Weight:	534.21
ALogP:	0.0031
MLogP:	2.78
XLogP:	2.611
# Rotatable Bonds:	12
Polar Surface Area:	198.15
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	36

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