NPASS Natural Product

Natural Product: NPC163055

Natural Product ID:	NPC163055
Common Name:	Chetoseminudin C
IUPAC Name:	(3S,6S)-3-(hydroxymethyl)-6-(1H-indol-3-ylmethyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione
Synonyms:	Chetoseminudin C; Chetoseminudin-C
Molecular Formula:	C16H19N3O3S2
Standard InCHIKey:	NOPTYKZKJYUDRQ-HOTGVXAUSA-N
Standard InCHI:	InChI=1S/C16H19N3O3S2/c1-23-15(7-10-8-17-12-6-4-3-5-11(10)12)13(21)19-16(9-20,24-2)14(22)18-15/h3-6,8,17,20H,7,9H2,1-2H3,(H,18,22)(H,19,21)/t15-,16-/m0/s1
Canonical SMILES:	CS[C@@]1(N=C(O)[C@](N=C1O)(CO)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	Collection Location	Reference
NPO32990	acrostalagmus luteoalbus scsio f457	Species	Plectosphaerellaceae	Eukaryota		PMID[23079524]
NPO4150	Ageratina tristis	Species	Asteraceae	Eukaryota		UNPD*
NPO5778	Oidiodendron truncatum	Species	Myxotrichaceae	Eukaryota	Antarctic	PMID[22583079]
NPO8658	Chaetomium seminudum	Species	Chaetomiaceae	Eukaryota		PMID[14738397]
NPO8658	Chaetomium seminudum	Species	Chaetomiaceae	Eukaryota		UNPD*

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Biological Activity

Activity Type	# Activity
IC50	10

Activity Type	# Activity
Cell Line	9
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000	nM	22583079
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000	nM	22583079
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000	nM	22583079
NPT2	Others	Unspecified		IC50	>	50	ug/ml	14738397
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	100000	nM	23079524
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	100000	nM	23079524
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000	nM	22583079
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000	nM	23079524
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000	nM	22583079
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000	nM	23079524

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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 NPC163055 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	235
0.1-0.2	1767
0.2-0.3	11743
0.3-0.4	12216
0.4-0.5	2214
0.5-0.6	1293
0.6-0.7	951
0.7-0.8	375
0.8-0.85	64
0.85-0.9	26
0.9-0.95	4
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.7544	Intermediate Similarity	NPC469811
0.7544	Intermediate Similarity	NPC201380
0.7544	Intermediate Similarity	NPC179787
0.7565	Intermediate Similarity	NPC303820
0.7565	Intermediate Similarity	NPC106771

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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 NPC163055 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	537
0.2-0.3	994
0.3-0.4	1458
0.4-0.5	2793
0.5-0.6	2059
0.6-0.7	983
0.7-0.8	147
0.8-0.85	21
0.85-0.9	3
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6954	Remote Similarity	NPD3395	Approved
0.6954	Remote Similarity	NPD3396	Approved
0.6961	Remote Similarity	NPD2189	Approved
0.6961	Remote Similarity	NPD2582	Approved
0.6961	Remote Similarity	NPD4671	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

CID163055 OpenBabel06191715532D 24 26 0 0 1 0 0 0 0 0999 V2000 0.1884 2.8741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0700 1.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5240 1.8965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0714 0.9532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9794 2.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8320 1.2412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3826 2.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 1.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5267 1.7919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9807 2.6829 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 3.3900 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 0.8660 -1.2321 0.0000 O 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 -0.7355 2.4914 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 11 2 0 0 0 0 6 12 2 0 0 0 0 7 10 1 0 0 0 0 8 10 2 0 0 0 0 8 17 1 0 0 0 0 9 20 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 21 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 7 1 1 0 0 0 15 18 1 0 0 0 0 15 23 1 0 0 0 0 16 9 1 1 0 0 0 16 19 1 0 0 0 0 16 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11360558
ChEMBL	CHEMBL470548
ZINC

Physicochemical Properties

Molecular Weight:	365.09
ALogP:	0.4559
MLogP:	2.34
XLogP:	2.455
# Rotatable Bonds:	10
Polar Surface Area:	151.8
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	24

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