NPASS Natural Product

Natural Product: NPC474027

Natural Product ID:	NPC474027
Common Name:	(1R,2R,3As,3A1S,3A2S,5S,5Ar,8S,8As,10As)-8-Isocyanato-1,2,5,8-Tetramethylhexadecahydropyrene-1-Carbonitrile
IUPAC Name:	(1R,2R,3aS,5S,5aR,8S,8aS,10aS,10bS,10cS)-8-isocyanato-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:	C22H32N2O
Standard InCHIKey:	PQKVPNQECCMWNB-RMBRTBKZSA-N
Standard InCHI:	InChI=1S/C22H32N2O/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:	O=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	=	0.0749	ug/ml	8450319
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0561	ug/ml	23227781
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2	ug/ml	23268606
NPT2	Others	Unspecified		Ratio IC50	=	36		DrugMatrix in vitro pharmacology data
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	220	nM	23829449
NPT2	Others	Unspecified		Ratio IC50	=	27		17284598

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 NPC474027 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	87
0.1-0.2	11736
0.2-0.3	12532
0.3-0.4	5509
0.4-0.5	924
0.5-0.6	70
0.6-0.7	24
0.7-0.8	3
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474435
0.9016	High Similarity	NPC475755
0.8906	High Similarity	NPC476288
0.8276	Intermediate Similarity	NPC212905
0.7846	Intermediate Similarity	NPC89921
0.7246	Intermediate Similarity	NPC474456
0.7183	Intermediate Similarity	NPC138409
0.697	Remote Similarity	NPC324944
0.6818	Remote Similarity	NPC173815
0.6712	Remote Similarity	NPC245223
0.6712	Remote Similarity	NPC124384
0.6667	Remote Similarity	NPC476135
0.6667	Remote Similarity	NPC318036
0.6623	Remote Similarity	NPC476308
0.6618	Remote Similarity	NPC21781
0.6571	Remote Similarity	NPC477740
0.6486	Remote Similarity	NPC184919
0.6429	Remote Similarity	NPC477739
0.64	Remote Similarity	NPC473442
0.64	Remote Similarity	NPC120167
0.6377	Remote Similarity	NPC28755
0.6377	Remote Similarity	NPC152211
0.6316	Remote Similarity	NPC476329
0.6286	Remote Similarity	NPC317778
0.625	Remote Similarity	NPC476682
0.625	Remote Similarity	NPC53276
0.6212	Remote Similarity	NPC474416
0.6164	Remote Similarity	NPC469970
0.6133	Remote Similarity	NPC271640
0.6	Remote Similarity	NPC472829
0.6	Remote Similarity	NPC25110
0.597	Remote Similarity	NPC472828
0.597	Remote Similarity	NPC475272
0.5915	Remote Similarity	NPC474455
0.5915	Remote Similarity	NPC474454
0.5915	Remote Similarity	NPC474420
0.5897	Remote Similarity	NPC110615
0.5857	Remote Similarity	NPC474457
0.5833	Remote Similarity	NPC257962
0.5797	Remote Similarity	NPC307063
0.5758	Remote Similarity	NPC476681
0.5676	Remote Similarity	NPC145715
0.5647	Remote Similarity	NPC90150
0.5634	Remote Similarity	NPC474415
0.5634	Remote Similarity	NPC475696
0.5634	Remote Similarity	NPC474528
0.56	Remote Similarity	NPC473959

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC474027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	78
0.1-0.2	3549
0.2-0.3	4679
0.3-0.4	701
0.4-0.5	133
0.5-0.6	19
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
0.5876	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD346	Approved
0.5738	Remote Similarity	NPD347	Approved

Structure

NPC474027 OpenBabel07101718282D 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 O 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	44584211
ChEMBL	CHEMBL458701
ZINC

Physicochemical Properties

Molecular Weight:	340.25
ALogP:	0.2195
MLogP:	3.55
XLogP:	7.398
# Rotatable Bonds:	5
Polar Surface Area:	53.22
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	25

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