NPASS Natural Product

Natural Product: NPC181086

Natural Product ID:	NPC181086
Common Name:	Aerophobin 2
IUPAC Name:	(5S,6R)-N-[3-(2-amino-1H-imidazol-5-yl)propyl]-7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
Synonyms:	Aerophobin 2
Molecular Formula:	C16H19Br2N5O4
Standard InCHIKey:	ZSZRBAQVYFYMTR-XJKSGUPXSA-N
Standard InCHI:	InChI=1S/C16H19Br2N5O4/c1-26-12-9(17)5-16(13(24)11(12)18)6-10(23-27-16)14(25)20-4-2-3-8-7-21-15(19)22-8/h5,7,13,24H,2-4,6H2,1H3,(H,20,25)(H3,19,21,22)/t13-,16+/m0/s1
Canonical SMILES:	COC1=C(Br)[C@@H]([C@]2(C=C1Br)ON=C(C2)C(=O)NCCCc1c[nH]c(=N)[nH]1)O
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
NPO33394	druinella sp.	Species	NA	NA		Fujian, China		PMID[12502317]

Biological Activity

Activity Type	# Activity
Others	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1523	Cell Line	NFF	Homo sapiens	Inhibition	=	25	%	17896816
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	=	66	%	14613317
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	20	%	14613317
NPT111	Cell Line	K562	Homo sapiens	ID50	=	6.91	ug/ml	23822611
NPT179	Cell Line	A2780	Homo sapiens	ID50	>	10	ug/ml	19715320

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 NPC181086 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	85
0.1-0.2	697
0.2-0.3	9278
0.3-0.4	18626
0.4-0.5	2022
0.5-0.6	154
0.6-0.7	7
0.7-0.8	10
0.8-0.85	4
0.85-0.9	2
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9844	High Similarity	NPC81079
0.9843	High Similarity	NPC304257
0.9286	High Similarity	NPC260270
0.9206	High Similarity	NPC145149
0.8692	High Similarity	NPC1702
0.8692	High Similarity	NPC158672
0.8496	Intermediate Similarity	NPC477220
0.8385	Intermediate Similarity	NPC66855
0.8273	Intermediate Similarity	NPC289324
0.8258	Intermediate Similarity	NPC313173
0.7958	Intermediate Similarity	NPC300912
0.7958	Intermediate Similarity	NPC202166
0.7958	Intermediate Similarity	NPC473261
0.7958	Intermediate Similarity	NPC473262
0.7902	Intermediate Similarity	NPC470886
0.7635	Intermediate Similarity	NPC130714
0.7552	Intermediate Similarity	NPC473683
0.7324	Intermediate Similarity	NPC172626
0.7324	Intermediate Similarity	NPC470892
0.711	Intermediate Similarity	NPC201900
0.6718	Remote Similarity	NPC45830
0.6718	Remote Similarity	NPC243106
0.6196	Remote Similarity	NPC202866
0.6077	Remote Similarity	NPC77435
0.6077	Remote Similarity	NPC259071
0.6044	Remote Similarity	NPC174607
0.6011	Remote Similarity	NPC147847
0.5882	Remote Similarity	NPC227953
0.5878	Remote Similarity	NPC471261
0.5833	Remote Similarity	NPC147238
0.5759	Remote Similarity	NPC471256
0.5723	Remote Similarity	NPC477400
0.5714	Remote Similarity	NPC475610
0.5714	Remote Similarity	NPC473249
0.5671	Remote Similarity	NPC142761
0.5622	Remote Similarity	NPC477254

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC181086 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	87
0.1-0.2	283
0.2-0.3	1980
0.3-0.4	5908
0.4-0.5	871
0.5-0.6	32
0.6-0.7	0
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
0.5762	Remote Similarity	NPD7623	Phase 3
0.5762	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7746	Phase 1
0.5714	Remote Similarity	NPD7747	Phase 1
0.5625	Remote Similarity	NPD8065	Phase 2

Structure

NPC181086 OpenBabel07101719522D 27 29 0 0 1 0 0 0 0 0999 V2000 4.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3962 -1.6711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2052 -2.2589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4826 -2.0779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3267 -0.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1187 -1.8522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -1.6750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7601 -1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7279 -1.6830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5878 0.9230 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.5878 -2.5411 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -8.7061 -1.8909 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6736 -1.4901 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.3212 -0.7695 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9848 -2.3522 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6555 -2.8913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 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 26 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 8 1 0 0 0 0 4 20 1 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 23 2 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 26 1 0 0 0 0 13 16 1 6 0 0 0 13 24 1 0 0 0 0 14 20 1 0 0 0 0 14 25 2 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 5 1 6 0 0 0 16 27 1 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	159038
ChEMBL	CHEMBL518701
ZINC

Physicochemical Properties

Molecular Weight:	502.98
ALogP:	-1.3032
MLogP:	2.01
XLogP:	2.402
# Rotatable Bonds:	11
Polar Surface Area:	128.06
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	27

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