NPASS Natural Product

Natural Product: NPC201900

Natural Product ID:	NPC201900
Common Name:	Aerophobin 1
IUPAC Name:	(5R,6S)-7,9-dibromo-6-hydroxy-N-[2-(1H-imidazol-5-yl)ethyl]-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
Synonyms:	Aerophobin 1
Molecular Formula:	C15H16Br2N4O4
Standard InCHIKey:	MDUQIEXQKMPARD-HIFRSBDPSA-N
Standard InCHI:	InChI=1S/C15H16Br2N4O4/c1-24-12-9(16)4-15(13(22)11(12)17)5-10(21-25-15)14(23)19-3-2-8-6-18-7-20-8/h4,6-7,13,22H,2-3,5H2,1H3,(H,18,20)(H,19,23)/t13-,15+/m1/s1
Canonical SMILES:	COC1=C(Br)[C@H]([C@@]2(C=C1Br)ON=C(C2)C(=O)NCCc1[nH]cnc1)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO13261	Suberea clavata	Species	Aplysinellidae	Eukaryota		Australia		PMID[19379003]
NPO33394	druinella sp.	Species	NA	NA		Fujian, China		PMID[12502317]

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Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Cell Line	2
Individual Protein	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	ID50	=	24.11	ug/ml	PubChem BioAssay data set
NPT179	Cell Line	A2780	Homo sapiens	ID50	=	21.53	ug/ml	23398362
NPT4197	Individual Protein	Coagulation factor XI	Homo sapiens	Inhibition	=	59	%	18053715
NPT4655	Individual Protein	Coagulation factor IX	Homo sapiens	Inhibition	<	5	%	18053715

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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 NPC201900 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	185
0.1-0.2	2127
0.2-0.3	21340
0.3-0.4	4412
0.4-0.5	2337
0.5-0.6	440
0.6-0.7	45
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.56	Remote Similarity	NPC473376
0.5605	Remote Similarity	NPC9635
0.5605	Remote Similarity	NPC300183
0.5606	Remote Similarity	NPC321052
0.5614	Remote Similarity	NPC155498

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Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC201900 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	561
0.2-0.3	2328
0.3-0.4	3355
0.4-0.5	2169
0.5-0.6	568
0.6-0.7	38
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.56	Remote Similarity	NPD8169	Discontinued
0.56	Remote Similarity	NPD1303	Phase 1
0.5602	Remote Similarity	NPD549	Approved
0.5603	Remote Similarity	NPD7471	Discontinued
0.5605	Remote Similarity	NPD8250	Phase 2

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Structure

NPC201900 OpenBabel07101719242D 25 27 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 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 6.1563 1.9499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1563 3.5679 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 -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 2 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 -0.5878 0.8090 0.0000 C 0 0 2 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 6.7440 2.7589 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 5.2052 3.2589 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 24 1 0 0 0 0 2 3 1 0 0 0 0 2 8 1 0 0 0 0 3 19 1 0 0 0 0 4 9 2 0 0 0 0 5 10 1 0 0 0 0 5 15 1 0 0 0 0 6 8 2 0 0 0 0 6 18 1 0 0 0 0 7 18 2 0 0 0 0 7 20 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 21 2 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 1 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 23 2 0 0 0 0 15 4 1 1 0 0 0 15 25 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	14484009
ChEMBL	CHEMBL499178
ZINC

Physicochemical Properties

Molecular Weight:	473.95
ALogP:	-1.0097
MLogP:	2.01
XLogP:	1.197
# Rotatable Bonds:	10
Polar Surface Area:	108.83
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	25

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