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

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30160	Cymbastela hooperi	Species	Axinellidae	Eukaryota				PMID[8759172]

Biological Activity

Activity Type	# Activity
IC50	4
Others	2

Activity Type	# Activity
Cell Line	1
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
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
NPT2	Others	Unspecified		Ratio IC50	=	56		19660948
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	126	nM	DrugMatrix in vivo data: Pathology
NPT2	Others	Unspecified		Ratio IC50	=	35		17665951

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

Similarity Score	Similarity Level	Natural Product ID
0.9016	High Similarity	NPC474027
0.9016	High Similarity	NPC474435
0.8333	Intermediate Similarity	NPC476288
0.8276	Intermediate Similarity	NPC212905
0.803	Intermediate Similarity	NPC474456
0.7313	Intermediate Similarity	NPC89921
0.7183	Intermediate Similarity	NPC184919
0.7121	Intermediate Similarity	NPC152211
0.7121	Intermediate Similarity	NPC28755
0.697	Remote Similarity	NPC324944
0.6818	Remote Similarity	NPC173815
0.6774	Remote Similarity	NPC472829
0.6719	Remote Similarity	NPC475272
0.6667	Remote Similarity	NPC318036
0.6618	Remote Similarity	NPC21781
0.6486	Remote Similarity	NPC138409
0.6338	Remote Similarity	NPC145715
0.6286	Remote Similarity	NPC317778
0.6267	Remote Similarity	NPC245223
0.6267	Remote Similarity	NPC124384
0.625	Remote Similarity	NPC53276
0.625	Remote Similarity	NPC473959
0.6216	Remote Similarity	NPC476135
0.6212	Remote Similarity	NPC474416
0.6203	Remote Similarity	NPC476308
0.6164	Remote Similarity	NPC469970
0.6133	Remote Similarity	NPC271640
0.6111	Remote Similarity	NPC477740
0.6056	Remote Similarity	NPC311809
0.5972	Remote Similarity	NPC477739
0.597	Remote Similarity	NPC472828
0.5915	Remote Similarity	NPC474455
0.5915	Remote Similarity	NPC474454
0.5915	Remote Similarity	NPC474420
0.5897	Remote Similarity	NPC476329
0.5867	Remote Similarity	NPC37792
0.5857	Remote Similarity	NPC474457
0.5811	Remote Similarity	NPC476682
0.5769	Remote Similarity	NPC473442
0.5769	Remote Similarity	NPC120167
0.5758	Remote Similarity	NPC476681
0.5663	Remote Similarity	NPC79704
0.5634	Remote Similarity	NPC474415
0.5634	Remote Similarity	NPC475696
0.5634	Remote Similarity	NPC474528

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

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.623	Remote Similarity	NPD873	Approved
0.623	Remote Similarity	NPD871	Approved
0.5738	Remote Similarity	NPD346	Approved
0.5738	Remote Similarity	NPD347	Approved

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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