NPASS Natural Product

Natural Product: NPC476288

Natural Product ID:	NPC476288
Common Name:	(1S,3S,4R,7S,8S,11S,12S,13S,15R,20R)-7-Formamido-20-Isocyanoisocycloamphilectane
IUPAC Name:	N-[(1S,3aR,4S,5aS,7R,8R,8aS,10aS,10bS,10cS)-8-cyano-1,4,7,8-tetramethyl-2,3,3a,4,5,5a,6,7,8a,9,10,10a,10b,10c-tetradecahydropyren-1-yl]formamide
Synonyms:
Molecular Formula:	C22H34N2O
Standard InCHIKey:	ONXNDTVZDXSXMX-RMBRTBKZSA-N
Standard InCHI:	InChI=1S/C22H34N2O/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/h12-20H,5-10H2,1-4H3,(H,24,25)/t13-,14+,15-,16+,17-,18-,19+,20+,21+,22-/m0/s1
Canonical SMILES:	OC=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
NPO33434	cymbastel hooperi	Species	NA	NA				PMID[19199790]

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.2	ug/ml	10.6019/CHEMBL1201861
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.6	ug/ml	10.6019/CHEMBL1201861
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.8	ug/ml	10.6019/CHEMBL1201861
NPT91	Cell Line	KB	Homo sapiens	IC50	>	5	ug/ml	22652224

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 NPC476288 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	67
0.1-0.2	9286
0.2-0.3	13795
0.3-0.4	6242
0.4-0.5	1359
0.5-0.6	114
0.6-0.7	14
0.7-0.8	8
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8906	High Similarity	NPC474027
0.8906	High Similarity	NPC474435
0.8906	High Similarity	NPC89921
0.8333	Intermediate Similarity	NPC475755
0.7639	Intermediate Similarity	NPC124384
0.7619	Intermediate Similarity	NPC212905
0.7606	Intermediate Similarity	NPC476135
0.7536	Intermediate Similarity	NPC477740
0.75	Intermediate Similarity	NPC476308
0.7391	Intermediate Similarity	NPC477739
0.72	Intermediate Similarity	NPC476329
0.7183	Intermediate Similarity	NPC476682
0.6933	Remote Similarity	NPC245223
0.6757	Remote Similarity	NPC474456
0.6494	Remote Similarity	NPC138409
0.6479	Remote Similarity	NPC324944
0.6389	Remote Similarity	NPC21781
0.6338	Remote Similarity	NPC173815
0.6282	Remote Similarity	NPC472831
0.6197	Remote Similarity	NPC318036
0.6076	Remote Similarity	NPC184919
0.6053	Remote Similarity	NPC53276
0.6047	Remote Similarity	NPC257962
0.6047	Remote Similarity	NPC192456
0.6	Remote Similarity	NPC473442
0.6	Remote Similarity	NPC120167
0.5974	Remote Similarity	NPC469970
0.5949	Remote Similarity	NPC271640
0.5946	Remote Similarity	NPC152211
0.5946	Remote Similarity	NPC28755
0.5867	Remote Similarity	NPC317778
0.5824	Remote Similarity	NPC21035
0.5778	Remote Similarity	NPC152684
0.5775	Remote Similarity	NPC474416
0.5775	Remote Similarity	NPC472828
0.5647	Remote Similarity	NPC25110

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476288 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	77
0.1-0.2	2728
0.2-0.3	5271
0.3-0.4	922
0.4-0.5	140
0.5-0.6	23
0.6-0.7	0
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
0.5758	Remote Similarity	NPD871	Approved
0.5758	Remote Similarity	NPD873	Approved
0.5743	Remote Similarity	NPD7812	Clinical (unspecified phase)

Structure

NPC476288 OpenBabel07101719152D 25 28 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 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 2.2261 2.5090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0546 0.7575 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7366 -1.2272 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2373 2.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0434 0.6085 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 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 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 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 1.6026 1.7272 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4311 -0.0243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8719 3.5890 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4199 -0.1733 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0322 0.4594 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 3 0 0 0 12 25 1 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	25073520
ChEMBL	CHEMBL562220
ZINC

Physicochemical Properties

Molecular Weight:	342.27
ALogP:	0.7038
MLogP:	3.55
XLogP:	5.736
# Rotatable Bonds:	6
Polar Surface Area:	56.38
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	25

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