NPASS Natural Product

Natural Product: NPC39092

Natural Product ID:	NPC39092
Common Name:	Gesashidine A
IUPAC Name:	1-[(1,3-dimethyl-5-methylsulfanylimidazol-1-ium-4-yl)methyl]-9H-pyrido[3,4-b]indol-6-ol
Synonyms:
Molecular Formula:	C18H18N4OS
Standard InCHIKey:	HEFUKQPQMJVIGY-UHFFFAOYSA-O
Standard InCHI:	InChI=1S/C18H18N4OS/c1-21-10-22(2)18(24-3)16(21)9-15-17-12(6-7-19-15)13-8-11(23)4-5-14(13)20-17/h4-8,10H,9H2,1-3H3,(H-,19,20,23)/p+1
Canonical SMILES:	CSc1n(C)c[n+](c1Cc1[nH]ccc2c1nc1c2cc(cc1)O)C
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
NPO32750	thorectidae sponge	Species	Thorectidae	Eukaryota				PMID[16038561]

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Biological Activity

Activity Type	# Activity
IC50	2
MIC	1

Activity Type	# Activity
Cell Line	2
Organism	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	>	10	ug/ml	PubChem BioAssay data set
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	16.6	ug/ml	PubChem BioAssay data set
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10	ug/ml	8759172

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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 NPC39092 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	631
0.1-0.2	6775
0.2-0.3	7516
0.3-0.4	11367
0.4-0.5	2350
0.5-0.6	1293
0.6-0.7	849
0.7-0.8	102
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.6776	Remote Similarity	NPC229893
0.6776	Remote Similarity	NPC92796
0.6776	Remote Similarity	NPC135141
0.6778	Remote Similarity	NPC219087
0.6786	Remote Similarity	NPC101350

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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 NPC39092 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	847
0.2-0.3	822
0.3-0.4	2023
0.4-0.5	2433
0.5-0.6	1612
0.6-0.7	973
0.7-0.8	123
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
0.6809	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5998	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD8101	Phase 3
0.6815	Remote Similarity	NPD1504	Discontinued
0.682	Remote Similarity	NPD2847	Phase 2

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Structure

NPC39092 OpenBabel07101718332D 24 27 0 0 0 0 0 0 0 0999 V2000 -1.4894 -2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0725 1.6939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4304 -0.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5644 0.0636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3406 -2.6589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3460 -2.7635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5644 -1.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5772 -0.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4304 -1.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7473 -1.7454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6983 -1.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6983 -0.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1650 -1.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1595 -0.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7582 -1.9544 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7473 -0.1274 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.2964 -1.9364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 1.3849 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 14 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 21 2 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 14 20 2 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 18 24 1 0 0 0 0 M CHG 1 21 1 M END $$$$

External Identifiers

PubChem CID	11279216
ChEMBL	CHEMBL469626
ZINC

Physicochemical Properties

Molecular Weight:	339.13
ALogP:	-1.3515
MLogP:	2.78
XLogP:	2.602
# Rotatable Bonds:	7
Polar Surface Area:	83.02
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	24

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