NPASS Natural Product

Natural Product: NPC159547

Natural Product ID:	NPC159547
Common Name:	Aeroplysinin-1
IUPAC Name:	2-[(1S,6R)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl]acetonitrile
Synonyms:	Aeroplysinin-1
Molecular Formula:	C9H9Br2NO3
Standard InCHIKey:	BGYNLOSBKBOJJD-IUCAKERBSA-N
Standard InCHI:	InChI=1S/C9H9Br2NO3/c1-15-7-5(10)4-9(14,2-3-12)8(13)6(7)11/h4,8,13-14H,2H2,1H3/t8-,9-/m0/s1
Canonical SMILES:	N#CC[C@]1(O)C=C(Br)C(=C([C@@H]1O)Br)OC
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Collection Location	Reference
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota		UNPD*
NPO1512	Cissampelos fasciculata	Species	Menispermaceae	Eukaryota		UNPD*
NPO27875	Fallopia convolvulus	Species	Polygonaceae	Eukaryota		UNPD*
NPO1594	[enterobacter] aerogenes	Species	Enterobacteriaceae	Bacteria		UNPD*
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota		UNPD*
NPO287	Wrightia javanica	Species	Apocynaceae	Eukaryota		UNPD*
NPO6901	Lophosoria quadripinnata	Species	Dicksoniaceae	Eukaryota		UNPD*
NPO3266	Euryops sulcatus	Species	Asteraceae	Eukaryota		UNPD*
NPO8290	Mycena megaspora	Species	Tricholomataceae	Eukaryota		UNPD*
NPO10995	Aplysina aerophoba	Species	Aplysinidae	Eukaryota		PMID[8786366]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	Red Sea	PMID[18656986]
NPO2651	Ceroplastes floridensis	Species	Coccidae	Eukaryota		UNPD*
NPO9047.1	Brassica rapa subsp. oleifera	Subspecies	Brassicaceae	Eukaryota		UNPD*
NPO3434	Thymus camphoratus	Species	Lamiaceae	Eukaryota		UNPD*
NPO8123	Aplysina cavernicola	Species	Aplysinidae	Eukaryota		UNPD*
NPO6725	Tulipa hybrid	Species	Liliaceae	Eukaryota		UNPD*
NPO4191	Thermococcus acidaminovorans	Species	Thermococcaceae	Archaea		UNPD*
NPO7223	Castela tortuosa	Species	Simaroubaceae	Eukaryota		UNPD*

Biological Activity

Activity Type	# Activity
IC50	14
MIC	1
Others	4

Activity Type	# Activity
Organism	3
Others	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		MIC	=	2000	nM	17507232
NPT2	Others	Unspecified		Ratio	=	14		17507232
NPT2	Others	Unspecified		IC50	=	8200	nM	8786366
NPT2	Others	Unspecified		IC50	=	6200	nM	8786366
NPT2	Others	Unspecified		IC50	=	18800	nM	8786366
NPT2	Others	Unspecified		IC50	=	5600	nM	8786366
NPT2	Others	Unspecified		IC50	=	37000	nM	8786366
NPT2	Others	Unspecified		IC50	=	27500	nM	8786366
NPT2	Others	Unspecified		IC50	=	1100	nM	8786366
NPT2	Others	Unspecified		IC50	=	700	nM	8786366
NPT2	Others	Unspecified		IC50	=	5400	nM	8786366
NPT2	Others	Unspecified		IC50	=	2800	nM	8786366
NPT2	Others	Unspecified		IC50	=	7500	nM	8786366
NPT2	Others	Unspecified		IC50	=	8900	nM	8786366
NPT2	Others	Unspecified		IC50	=	3500	nM	8786366
NPT2	Others	Unspecified		IC50	=	2000	nM	8786366
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	9	mm	18656986
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	11	mm	18656986
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	7	mm	18656986

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 NPC159547 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	52
0.1-0.2	1196
0.2-0.3	11109
0.3-0.4	15033
0.4-0.5	3274
0.5-0.6	221
0.6-0.7	4
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	Natural Product ID
0.6905	Remote Similarity	NPC8161
0.6154	Remote Similarity	NPC476586
0.6104	Remote Similarity	NPC476584
0.6026	Remote Similarity	NPC471460
0.5844	Remote Similarity	NPC476585
0.575	Remote Similarity	NPC473722
0.5732	Remote Similarity	NPC238223
0.5679	Remote Similarity	NPC267027
0.5641	Remote Similarity	NPC258788
0.5625	Remote Similarity	NPC90463
0.5625	Remote Similarity	NPC235311
0.5625	Remote Similarity	NPC253468
0.561	Remote Similarity	NPC82337
0.561	Remote Similarity	NPC132286

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC159547 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	75
0.1-0.2	2004
0.2-0.3	5028
0.3-0.4	1872
0.4-0.5	175
0.5-0.6	7
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
		NPD

Structure

External Identifiers

PubChem CID	100308
ChEMBL	CHEMBL462153
ZINC

Physicochemical Properties

Molecular Weight:	336.89
ALogP:	0.156
MLogP:	1.79
XLogP:	0.843
# Rotatable Bonds:	7
Polar Surface Area:	73.48
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	15

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