NPASS Natural Product

Natural Product: NPC147686

Natural Product ID:	NPC147686
Common Name:	Liquirtigenin
IUPAC Name:	(2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:	(2S)-Liquiritigenin; 4',7-Dihydroxyflavanone; 7,4'-Dihydroxyflavanone; Liquiritigenin; Liquirtigenin
Molecular Formula:	C15H12O4
Standard InCHIKey:	FURUXTVZLHCCNA-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1
Canonical SMILES:	Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)cc(cc2)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	UNPD*
NPO10038.1	Abies pinsapo var. marocana	Varieties	Pinaceae	Eukaryota	UNPD*
NPO10080	Teucrium betonicum	Species	Lamiaceae	Eukaryota	UNPD*
NPO10132	Schizophyllum lobatum	Species	Schizophyllaceae	Eukaryota	UNPD*
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	UNPD*
NPO10917	Junceella gemmacea	Species	Ellisellidae	Eukaryota	UNPD*
NPO1293	Streptomyces matensis	Species	Streptomycetaceae	Bacteria	UNPD*
NPO13474	Euphrasia genargentea	Species	Orobanchaceae	Eukaryota	UNPD*
NPO13659	Helichrysum asperum	Species	Asteraceae	Eukaryota	UNPD*
NPO1383.1	Murraya paniculata var. omphalocarpa	Varieties	Rutaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
IC50	27
Ki	1
Others	38

Activity Type	# Activity
Cell Line	29
Individual Protein	20
Organism	10
Others	7

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000	nM	20494492
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	GI	=	85	%	21866899
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	22.5	ug/ml	15787450
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	100	%	3379415
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	IC50	=	11300	nM	3379415
NPT1485	Individual Protein	Collagenase	Porphyromonas gingivalis	Inhibition	=	21	%	21866899
NPT1485	Individual Protein	Collagenase	Porphyromonas gingivalis	Activity	=	79	%	21866899
NPT1485	Individual Protein	Collagenase	Porphyromonas gingivalis	Activity	=	82	%	21866899
NPT1485	Individual Protein	Collagenase	Porphyromonas gingivalis	Activity	=	83	%	21866899
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000	nM	18440233

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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 NPC147686 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	275
0.1-0.2	1169
0.2-0.3	2661
0.3-0.4	6344
0.4-0.5	6685
0.5-0.6	2477
0.6-0.7	4394
0.7-0.8	3695
0.8-0.85	1672
0.85-0.9	969
0.9-0.95	453
0.95-1	95

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Similarity Score	Similarity Level	Natural Product ID
0.9338	High Similarity	NPC294409
0.9338	High Similarity	NPC162680
0.9338	High Similarity	NPC181124
0.9338	High Similarity	NPC116632
0.9338	High Similarity	NPC212767

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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 NPC147686 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	895
0.2-0.3	1493
0.3-0.4	2416
0.4-0.5	2067
0.5-0.6	1292
0.6-0.7	489
0.7-0.8	163
0.8-0.85	38
0.85-0.9	17
0.9-0.95	5
0.95-1	3

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7101	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7199	Phase 2
0.7111	Intermediate Similarity	NPD9263	Approved
0.7111	Intermediate Similarity	NPD9267	Approved
0.7111	Intermediate Similarity	NPD9265	Clinical (unspecified phase)

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Structure

External Identifiers

PubChem CID	114829
ChEMBL	CHEMBL252642
ZINC

Physicochemical Properties

Molecular Weight:	256.07
ALogP:	-1.3541
MLogP:	2.67
XLogP:	1.86
# Rotatable Bonds:	3
Polar Surface Area:	66.76
# H-Bond Aceptor:	1
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	19

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