NPASS Natural Product

Natural Product: NPC80710

Natural Product ID:	NPC80710
Common Name:	Calycosin
IUPAC Name:	7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)chromen-4-one
Synonyms:	Calycosin
Molecular Formula:	C16H12O5
Standard InCHIKey:	ZZAJQOPSWWVMBI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3
Canonical SMILES:	COc1ccc(cc1O)c1coc2c(c1=O)ccc(c2)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*
NPO10132	Schizophyllum lobatum	Species	Schizophyllaceae	Eukaryota	UNPD*
NPO10447	Triclisia subcordata	Species	Menispermaceae	Eukaryota	UNPD*
NPO10682	Cystoseira mediterranea	Species	Sargassaceae	Eukaryota	UNPD*
NPO10782	Myroxylon balsamum	Species	Fabaceae	Eukaryota	DOI[10.1016/S0031-9422(00)89391-7]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	UNPD*
NPO10916	Cladrastis spp.	Species	Fabaceae	Eukaryota	TCMID*
NPO10917	Junceella gemmacea	Species	Ellisellidae	Eukaryota	UNPD*
NPO10947	Aspilia parvifolia	Species	Asteraceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
AC50	1
IC50	17
Others	10
Potency	18

Activity Type	# Activity
Cell Line	19
Individual Protein	13
Organism	5
Others	7
Uncleic Acid	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000	nM	25592708
NPT157	Individual Protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency		12589.3	nM	PubChem BioAssay data set
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000	nM	18440233
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	159000	nM	16441066
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency		79432.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	98000	nM	18440233
NPT2	Others	Unspecified		IC50	>	100000	nM	18440233
NPT2	Others	Unspecified		Inhibition	=	1	%	19931462
NPT2	Others	Unspecified		Potency		891.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		35481.3	nM	PubChem BioAssay data set

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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 NPC80710 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	285
0.1-0.2	1215
0.2-0.3	2532
0.3-0.4	6365
0.4-0.5	6660
0.5-0.6	2276
0.6-0.7	3499
0.7-0.8	4358
0.8-0.85	1878
0.85-0.9	1236
0.9-0.95	526
0.95-1	59

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Similarity Score	Similarity Level	Natural Product ID
0.9262	High Similarity	NPC292214
0.9262	High Similarity	NPC273462
0.9262	High Similarity	NPC160951
0.9262	High Similarity	NPC176775
0.9262	High Similarity	NPC206238

Showing 1 to 5 of 200 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 NPC80710 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	881
0.2-0.3	1533
0.3-0.4	2592
0.4-0.5	1944
0.5-0.6	1163
0.6-0.7	534
0.7-0.8	143
0.8-0.85	35
0.85-0.9	18
0.9-0.95	7
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7011	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4662	Approved
0.7012	Intermediate Similarity	NPD4661	Approved
0.7024	Intermediate Similarity	NPD6844	Discontinued
0.7037	Intermediate Similarity	NPD2354	Approved

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Structure

CID80710 OpenBabel06191715422D 21 23 0 0 0 0 0 0 0 0999 V2000 -4.3301 4.5000 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 2.5981 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 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 -1.7321 3.0000 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 -0.8660 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 2.5981 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 -0.8660 1.5000 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 -3.4641 3.0000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 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 -4.3301 3.5000 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 20 1 0 0 0 0 2 5 2 0 0 0 0 2 9 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 21 1 0 0 0 0 9 12 1 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5280448
ChEMBL	CHEMBL241608
ZINC

Physicochemical Properties

Molecular Weight:	284.07
ALogP:	-1.6391
MLogP:	2.67
XLogP:	2.031
# Rotatable Bonds:	5
Polar Surface Area:	75.99
# H-Bond Aceptor:	1
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	21

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