NPASS Natural Product

Natural Product: NPC475755

Natural Product ID:	NPC475755
Common Name:	(1R,2R,3As,3A1S,3A2S,5S,5Ar,8S,8As,10As)-8-Isothiocyanato-1,2,5,8-Tetramethylhexadecahydropyrene-1-Carbonitrile
IUPAC Name:	(1R,2R,3aS,5S,5aR,8S,8aS,10aS,10bS,10cS)-8-isothiocyanato-1,2,5,8-tetramethyl-2,3,3a,4,5,5a,6,7,8a,9,10,10a,10b,10c-tetradecahydropyrene-1-carbonitrile
Synonyms:
Molecular Formula:	C22H32N2S
Standard InCHIKey:	QQXBCHYMIFYUTP-RMBRTBKZSA-N
Standard InCHI:	InChI=1S/C22H32N2S/c1-13-9-15-10-14(2)21(3,11-23)17-5-6-18-20(19(15)17)16(13)7-8-22(18,4)24-12-25/h13-20H,5-10H2,1-4H3/t13-,14+,15-,16+,17-,18-,19+,20+,21+,22-/m0/s1
Canonical SMILES:	S=C=N[C@@]1(C)CC[C@H]2[C@@H]3[C@@H]1CC[C@H]1[C@H]3[C@@H](C[C@@H]2C)C[C@H]([C@@]1(C)C#N)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
NPO30160	Cymbastela hooperi	Species	Axinellidae	Eukaryota				PMID[8759172]

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Biological Activity

Activity Type	# Activity
IC50	4
Others	2

Activity Type	# Activity
Cell Line	1
Organism	3
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio IC50	=	56		19660948
NPT2	Others	Unspecified		Ratio IC50	=	35		17665951
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	126	nM	DrugMatrix in vivo data: Pathology
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0451	ug/ml	23859780
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0285	ug/ml	15217273
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.6	ug/ml	19053514

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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 NPC475755 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	273
0.1-0.2	15744
0.2-0.3	10893
0.3-0.4	3573
0.4-0.5	332
0.5-0.6	45
0.6-0.7	20
0.7-0.8	4
0.8-0.85	3
0.85-0.9	0
0.9-0.95	2
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.5634	Remote Similarity	NPC474415
0.5634	Remote Similarity	NPC475696
0.5634	Remote Similarity	NPC474528
0.5663	Remote Similarity	NPC79704
0.5758	Remote Similarity	NPC476681

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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 NPC475755 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	4546
0.2-0.3	3885
0.3-0.4	475
0.4-0.5	71
0.5-0.6	12
0.6-0.7	2
0.7-0.8	0
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
0.5738	Remote Similarity	NPD346	Approved
0.5738	Remote Similarity	NPD347	Approved
0.623	Remote Similarity	NPD873	Approved
0.623	Remote Similarity	NPD871	Approved

Showing 1 to 4 of 4 entries

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Structure

NPC475755 OpenBabel07101718332D 25 28 0 0 1 0 0 0 0 0999 V2000 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -1.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2859 -0.6733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3712 2.1581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 -1.4311 0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3735 0.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9206 0.2575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9947 2.9399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2395 -1.2930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2971 -0.5243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7366 1.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5441 1.0394 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3601 2.0090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6294 3.8708 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 14 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 6 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 21 1 0 0 0 0 11 23 3 0 0 0 0 12 24 2 0 0 0 0 12 25 2 0 0 0 0 13 1 1 6 0 0 0 13 16 1 0 0 0 0 14 21 1 6 0 0 0 15 9 1 6 0 0 0 15 19 1 0 0 0 0 16 7 1 1 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 6 0 0 0 18 20 1 0 0 0 0 18 22 1 1 0 0 0 19 20 1 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44584210
ChEMBL	CHEMBL514250
ZINC

Physicochemical Properties

Molecular Weight:	356.23
ALogP:	1.1186
MLogP:	3.55
XLogP:	7.296
# Rotatable Bonds:	5
Polar Surface Area:	68.24
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	25

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