NPASS Natural Product

Natural Product: NPC239737

Natural Product ID:	NPC239737
Common Name:	Riboprine
IUPAC Name:	(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolane-3,4-diol
Synonyms:	IPA; N6-Isopentenyladenosine; Riboprine
Molecular Formula:	C15H21N5O4
Standard InCHIKey:	USVMJSALORZVDV-SDBHATRESA-N
Standard InCHI:	InChI=1S/C15H21N5O4/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(5-21)24-15/h3,6-7,9,11-12,15,21-23H,4-5H2,1-2H3,(H,16,17,18)/t9-,11-,12-,15-/m1/s1
Canonical SMILES:	OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCC=C(C)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Show entries

Search:

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	TM-MC*
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	DOI[10.1074/jbc.M314195200]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	TM-MC*
NPO25773	Dioscorea composita	Species	Dioscoreaceae	Eukaryota	UNPD*
NPO25901	Isodon wightii	Species	Lamiaceae	Eukaryota	UNPD*
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	UNPD*
NPO26511	Phalaenopsis amboinensis	Species	Orchidaceae	Eukaryota	UNPD*
NPO26539	Vanillosmopsis brasiliensis	NA	NA	NA	UNPD*
NPO26659	Annona bullata	Species	Annonaceae	Eukaryota	UNPD*
NPO26730	Canarium boivinii	Species	Burseraceae	Eukaryota	UNPD*

Showing 1 to 10 of 11 entries

Previous1 2Next

Biological Activity

Activity Type	# Activity
AC50	3
EC50	1
IC50	18
Kd	4
Others	4
Potency	22

Activity Type	# Activity
Cell Line	1
Individual Protein	9
Organism	2
Others	40

Show entries

Search:

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1224	Individual Protein	Glyceraldehyde-3-phosphate dehydrogenase liver	Homo sapiens	Inhibition	=	84	%	9934461
NPT1224	Individual Protein	Glyceraldehyde-3-phosphate dehydrogenase liver	Homo sapiens	IC50	>	5000000	nM	9822549
NPT1224	Individual Protein	Glyceraldehyde-3-phosphate dehydrogenase liver	Homo sapiens	Inhibition	=	84	%	9822549
NPT1384	Individual Protein	Farnesyl diphosphate synthase	Homo sapiens	Kd	=	1210000	nM	25184810
NPT1384	Individual Protein	Farnesyl diphosphate synthase	Homo sapiens	Kd	=	550000	nM	25184810
NPT1384	Individual Protein	Farnesyl diphosphate synthase	Homo sapiens	Kd	=	2210000	nM	25184810
NPT1384	Individual Protein	Farnesyl diphosphate synthase	Homo sapiens	Kd	=	2020000	nM	25184810
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency		3348.9	nM	PubChem BioAssay data set
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	IC50	=	360000	nM	20921305
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency		26832.5	nM	PubChem BioAssay data set

Showing 1 to 10 of 44 entries

Previous1 2 3 4 5Next

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 NPC239737 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	192
0.1-0.2	14501
0.2-0.3	11931
0.3-0.4	2874
0.4-0.5	1137
0.5-0.6	126
0.6-0.7	40
0.7-0.8	41
0.8-0.85	14
0.85-0.9	24
0.9-0.95	9
0.95-1	0

Show entries

Search:

Similarity Score	Similarity Level	Natural Product ID
0.5607	Remote Similarity	NPC470139
0.5616	Remote Similarity	NPC208751
0.5634	Remote Similarity	NPC50511
0.5647	Remote Similarity	NPC126634
0.5665	Remote Similarity	NPC226184

Showing 1 to 5 of 152 entries

Previous1 2 3 4 5…31Next

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC239737 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	118
0.1-0.2	1279
0.2-0.3	3307
0.3-0.4	2394
0.4-0.5	1498
0.5-0.6	409
0.6-0.7	79
0.7-0.8	40
0.8-0.85	19
0.85-0.9	9
0.9-0.95	9
0.95-1	0

Show entries

Search:

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5747	Remote Similarity	NPD9704	Approved
0.5747	Remote Similarity	NPD5342	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD1333	Phase 3
0.5761	Remote Similarity	NPD3130	Discontinued
0.5764	Remote Similarity	NPD6351	Discovery

Showing 1 to 5 of 200 entries

Previous1 2 3 4 5…40Next

Structure

CID239737 OpenBabel06191716042D 24 26 0 0 1 0 0 0 0 0999 V2000 -6.4582 2.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3242 0.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5921 0.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5921 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9941 1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7916 -2.0350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4582 1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9941 -0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8601 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7261 -0.9523 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8601 0.5477 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 0.5477 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7861 -1.9305 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6418 0.4307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1160 -1.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2319 -2.5772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 8 1 0 0 0 0 3 4 1 0 0 0 0 3 8 2 0 0 0 0 4 16 1 0 0 0 0 5 21 1 0 0 0 0 6 17 2 0 0 0 0 6 18 1 0 0 0 0 7 19 2 0 0 0 0 7 20 1 0 0 0 0 9 5 1 6 0 0 0 9 11 1 0 0 0 0 9 24 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 1 0 0 0 12 15 1 0 0 0 0 12 23 1 1 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 20 1 6 0 0 0 15 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	24405
ChEMBL	CHEMBL452867
ZINC

Physicochemical Properties

Molecular Weight:	335.16
ALogP:	-0.3818
MLogP:	2.12
XLogP:	-0.218
# Rotatable Bonds:	10
Polar Surface Area:	125.55
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	24

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs