NPASS Natural Product

Natural Product: NPC106771

Natural Product ID:	NPC106771
Common Name:	(3S,5R)-6''-Debromo-3,4-Dihydrohamacanthin B
IUPAC Name:	(3S,5R)-5-(6-bromo-1H-indol-3-yl)-3-(1H-indol-3-yl)piperazin-2-one
Synonyms:
Molecular Formula:	C20H17BrN4O
Standard InCHIKey:	BAHAHDZOJKHNMC-OALUTQOASA-N
Standard InCHI:	InChI=1S/C20H17BrN4O/c21-11-5-6-13-14(8-23-17(13)7-11)18-10-24-20(26)19(25-18)15-9-22-16-4-2-1-3-12(15)16/h1-9,18-19,22-23,25H,10H2,(H,24,26)/t18-,19-/m0/s1
Canonical SMILES:	Brc1ccc2c(c1)[nH]cc2[C@@H]1CN=C([C@@H](N1)c1c[nH]c2c1cccc2)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
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota				PMID[17253840]

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Biological Activity

Activity Type	# Activity
ED50	5
MIC	20

Activity Type	# Activity
Cell Line	5
Organism	20

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	25	ug/ml	16417306
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	25	ug/ml	15808482
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	>	25	ug/ml	DrugMatrix in vitro pharmacology data
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	25	ug/ml	DrugMatrix in vitro pharmacology data
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	6	ug/ml	19299148
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	7.1	ug/ml	15787436
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	6.3	ug/ml	15787436
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	25	ug/ml	15104491
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	25	ug/ml	8027972
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	25	ug/ml	11266159

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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 NPC106771 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	507
0.1-0.2	4715
0.2-0.3	14821
0.3-0.4	6452
0.4-0.5	1932
0.5-0.6	1268
0.6-0.7	812
0.7-0.8	343
0.8-0.85	27
0.85-0.9	5
0.9-0.95	1
0.95-1	6

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Similarity Score	Similarity Level	Natural Product ID
0.7376	Intermediate Similarity	NPC77555
0.7381	Intermediate Similarity	NPC6865
0.7381	Intermediate Similarity	NPC153980
0.7382	Intermediate Similarity	NPC313791
0.7389	Intermediate Similarity	NPC159856

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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 NPC106771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	622
0.2-0.3	1236
0.3-0.4	1850
0.4-0.5	2539
0.5-0.6	1768
0.6-0.7	763
0.7-0.8	100
0.8-0.85	4
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
0.6734	Remote Similarity	NPD6492	Phase 2
0.6743	Remote Similarity	NPD6749	Phase 1
0.6744	Remote Similarity	NPD4865	Approved
0.6744	Remote Similarity	NPD1392	Approved
0.6745	Remote Similarity	NPD5017	Discontinued

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Structure

NPC106771 OpenBabel07101719132D 26 30 0 0 1 0 0 0 0 0999 V2000 -4.2346 -2.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1006 -1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3686 -1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1006 -0.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6320 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7660 -2.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7660 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6389 -3.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0322 0.5862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6320 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3686 -0.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 -2.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6254 -0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2346 -0.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -1.6942 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6473 -0.5352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 -4.4543 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.0267 0.4817 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 -4.2633 0.0000 N 0 0 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 -1.3383 -1.4863 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 12 2 0 0 0 0 4 16 2 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 23 1 0 0 0 0 9 15 2 0 0 0 0 9 22 1 0 0 0 0 10 18 1 0 0 0 0 10 24 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 14 1 1 0 0 0 18 25 1 0 0 0 0 19 15 1 1 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10835321
ChEMBL	CHEMBL376042
ZINC

Physicochemical Properties

Molecular Weight:	408.06
ALogP:	-0.8741
MLogP:	3
XLogP:	3.854
# Rotatable Bonds:	4
Polar Surface Area:	76.2
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	26

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