NPASS Natural Product

Natural Product: NPC248454

Natural Product ID:	NPC248454
Common Name:	3,6 Bismethyl(Thiocyclo)Alanyltryptophyl
IUPAC Name:	(3S,6S)-3-(1H-indol-3-ylmethyl)-6-methyl-3,6-bis(methylsulfanyl)piperazine-2,5-dione
Synonyms:	3,6 Bismethyl(Thiocyclo)Alanyltryptophyl
Molecular Formula:	C16H19N3O2S2
Standard InCHIKey:	WZCXTZDWTILORX-HOTGVXAUSA-N
Standard InCHI:	InChI=1S/C16H19N3O2S2/c1-15(22-2)13(20)19-16(23-3,14(21)18-15)8-10-9-17-12-7-5-4-6-11(10)12/h4-7,9,17H,8H2,1-3H3,(H,18,21)(H,19,20)/t15-,16-/m0/s1
Canonical SMILES:	CS[C@@]1(N=C(O)[C@](N=C1O)(C)SC)Cc1c[nH]c2c1cccc2
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
NPO333	Nectria inventa	Species	Nectriaceae	Eukaryota	isolated from sediment	At >600 m in the Monterey Bay trench		PMID[20303767]

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Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	>	50000	nM	25993619

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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 NPC248454 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	288
0.1-0.2	2482
0.2-0.3	12909
0.3-0.4	10442
0.4-0.5	2072
0.5-0.6	1278
0.6-0.7	923
0.7-0.8	385
0.8-0.85	80
0.85-0.9	23
0.9-0.95	6
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.764	Intermediate Similarity	NPC329688
0.7644	Intermediate Similarity	NPC155143
0.7647	Intermediate Similarity	NPC195239
0.7647	Intermediate Similarity	NPC157828
0.7647	Intermediate Similarity	NPC325903

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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 NPC248454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	540
0.2-0.3	1096
0.3-0.4	1400
0.4-0.5	2663
0.5-0.6	2060
0.6-0.7	999
0.7-0.8	179
0.8-0.85	34
0.85-0.9	2
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7024	Intermediate Similarity	NPD792	Discontinued
0.7027	Intermediate Similarity	NPD2381	Approved
0.7027	Intermediate Similarity	NPD3348	Phase 2
0.7027	Intermediate Similarity	NPD2382	Approved
0.7027	Intermediate Similarity	NPD2380	Approved

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Structure

NPC248454 OpenBabel07101718282D 23 25 0 0 1 0 0 0 0 0999 V2000 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1884 0.8741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0700 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5240 -0.1035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0714 -1.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9794 0.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3826 0.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5267 -0.2081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9807 0.6829 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2736 1.3900 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -1.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 11 2 0 0 0 0 7 12 2 0 0 0 0 8 10 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 1 1 1 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 8 1 1 0 0 0 16 19 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	21575389
ChEMBL	CHEMBL1089314
ZINC

Physicochemical Properties

Molecular Weight:	349.09
ALogP:	0.9559
MLogP:	2.45
XLogP:	3.158
# Rotatable Bonds:	9
Polar Surface Area:	131.57
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	23

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