NPASS Natural Product

Natural Product: NPC2989

Natural Product ID:	NPC2989
Common Name:	Warfarin
IUPAC Name:	4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one
Synonyms:	Warfarin
Molecular Formula:	C19H16O4
Standard InCHIKey:	PJVWKTKQMONHTI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3
Canonical SMILES:	CC(=O)CC(c1c(=O)oc2c(c1O)cccc2)c1ccccc1
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
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota				TCMID*

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Biological Activity

Activity Type	# Activity
EC50	1
ED50	1
IC50	6
Kd	10
Ki	1
LD50	1
Others	55
Potency	30

Activity Type	# Activity
Cell Line	7
Individual Protein	43
Organism	22
Others	28
Subcellular	1
Tissue	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	<	10	%	21467212
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Inhibition	<	10	%	21467212
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	486000	nM	10.1007/s00044-011-9703-4
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Kd	=	9000	nM	10821711
NPT2	Others	Unspecified		Inhibition	=	41	%	14741253
NPT2	Others	Unspecified		IC50	=	2200	nM	17275317
NPT2	Others	Unspecified		EC50	=	89600	nM	20973485
NPT2	Others	Unspecified		Potency		2238.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	8.32	nM	21510613

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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 NPC2989 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	209
0.1-0.2	1041
0.2-0.3	2063
0.3-0.4	4632
0.4-0.5	8494
0.5-0.6	3051
0.6-0.7	6601
0.7-0.8	4632
0.8-0.85	152
0.85-0.9	13
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7971	Intermediate Similarity	NPC112192
0.7971	Intermediate Similarity	NPC66384
0.7971	Intermediate Similarity	NPC128348
0.7971	Intermediate Similarity	NPC309717
0.7971	Intermediate Similarity	NPC189106

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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 NPC2989 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	831
0.2-0.3	1188
0.3-0.4	2116
0.4-0.5	2363
0.5-0.6	1526
0.6-0.7	690
0.7-0.8	189
0.8-0.85	19
0.85-0.9	2
0.9-0.95	0
0.95-1	4

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7037	Intermediate Similarity	NPD6387	Discontinued
0.7044	Intermediate Similarity	NPD3882	Suspended
0.7047	Intermediate Similarity	NPD5762	Approved
0.7047	Intermediate Similarity	NPD5763	Approved
0.7059	Intermediate Similarity	NPD642	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

CID2989 OpenBabel06191715322D 23 25 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 1.7321 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 12 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 10 16 2 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 20 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 16 23 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	54678486
ChEMBL	CHEMBL1464
ZINC

Physicochemical Properties

Molecular Weight:	308.10
ALogP:	-0.732
MLogP:	3.11
XLogP:	5.519
# Rotatable Bonds:	6
Polar Surface Area:	63.6
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	23

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