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

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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	=	36		DrugMatrix in vitro pharmacology data
NPT2	Others	Unspecified		Ratio IC50	=	27		17284598
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	220	nM	23829449
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

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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 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

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Similarity Score	Similarity Level	Natural Product ID
0.56	Remote Similarity	NPC473959
0.5634	Remote Similarity	NPC474415
0.5634	Remote Similarity	NPC475696
0.5634	Remote Similarity	NPC474528
0.5647	Remote Similarity	NPC90150

Showing 1 to 5 of 47 entries

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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 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

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5738	Remote Similarity	NPD346	Approved
0.5738	Remote Similarity	NPD347	Approved
0.5876	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.623	Remote Similarity	NPD873	Approved
0.623	Remote Similarity	NPD871	Approved

Showing 1 to 5 of 5 entries

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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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