NPASS Natural Product

Natural Product: NPC276444

Natural Product ID:	NPC276444
Common Name:	Artonin E
IUPAC Name:	5-hydroxy-8,8-dimethyl-3-(3-methylbut-2-enyl)-2-(2,4,5-trihydroxyphenyl)pyrano[2,3-h]chromen-4-one
Synonyms:	Artonin E
Molecular Formula:	C25H24O7
Standard InCHIKey:	HDHRTQZSBFUBMJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H24O7/c1-12(2)5-6-14-22(30)21-19(29)11-20-13(7-8-25(3,4)32-20)24(21)31-23(14)15-9-17(27)18(28)10-16(15)26/h5,7-11,26-29H,6H2,1-4H3
Canonical SMILES:	CC(=CCc1c(oc2c(c1=O)c(O)cc1c2C=CC(O1)(C)C)c1cc(O)c(cc1O)O)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO12131	Salvia calycina	Species	Lamiaceae	Eukaryota	UNPD*
NPO14058	Papaver pavoninum	Species	Papaveraceae	Eukaryota	UNPD*
NPO14309	Desmodium tortuosum	Species	Fabaceae	Eukaryota	UNPD*
NPO14430	Grateloupia carnosa	Species	Halymeniaceae	Eukaryota	UNPD*
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	UNPD*
NPO15554	Eucalyptus amplifolia	Species	Myrtaceae	Eukaryota	UNPD*
NPO15835	Glycyrrhiza	Species	Fabaceae	Eukaryota	TCMSP*
NPO28803	Artocarpus chama	Species	Moraceae	Eukaryota	UNPD*
NPO28969	Solanum sarrachoides	Species	Solanaceae	Eukaryota	UNPD*
NPO29156	Conyza incana	Species	Asteraceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
ED50	11
Others	10

Activity Type	# Activity
Cell Line	19
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	4.3	ug/ml	15165133
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	=	3.3	ug/ml	15165133
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	58.4	%	25537111
NPT196	Cell Line	AGS	Homo sapiens	FC	=	1.9		25537111
NPT196	Cell Line	AGS	Homo sapiens	Inhibition	=	3.6	%	25537111
NPT196	Cell Line	AGS	Homo sapiens	FC	=	12.2		25537111
NPT196	Cell Line	AGS	Homo sapiens	FC	=	3.7		25537111
NPT196	Cell Line	AGS	Homo sapiens	Inhibition	=	2.9	%	25537111
NPT196	Cell Line	AGS	Homo sapiens	Inhibition	=	32.7	%	25537111
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	44	%	25537111

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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 NPC276444 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	328
0.1-0.2	1293
0.2-0.3	2703
0.3-0.4	6959
0.4-0.5	6037
0.5-0.6	2471
0.6-0.7	3632
0.7-0.8	4088
0.8-0.85	1612
0.85-0.9	1197
0.9-0.95	541
0.95-1	28

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Similarity Score	Similarity Level	Natural Product ID
0.9226	High Similarity	NPC100123
0.9226	High Similarity	NPC474290
0.9226	High Similarity	NPC53545
0.9226	High Similarity	NPC117418
0.9226	High Similarity	NPC250214

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 NPC276444 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	925
0.2-0.3	1593
0.3-0.4	2651
0.4-0.5	1910
0.5-0.6	1068
0.6-0.7	463
0.7-0.8	148
0.8-0.85	35
0.85-0.9	10
0.9-0.95	5
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.699	Remote Similarity	NPD8151	Discontinued
0.6993	Remote Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD6671	Approved
0.7	Intermediate Similarity	NPD6233	Phase 2
0.7018	Intermediate Similarity	NPD6585	Discontinued

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Structure

CID276444 OpenBabel06191716082D 32 35 0 0 0 0 0 0 0 0999 V2000 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 -6.9282 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 -0.8660 0.5000 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 -3.4641 2.0000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 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 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 12 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 12 2 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 25 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 11 20 1 0 0 0 0 13 20 2 0 0 0 0 13 24 1 0 0 0 0 14 22 1 0 0 0 0 14 23 2 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 21 1 0 0 0 0 19 29 1 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 22 30 2 0 0 0 0 23 31 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5481962
ChEMBL	CHEMBL463106
ZINC

Physicochemical Properties

Molecular Weight:	436.15
ALogP:	0.3515
MLogP:	3.44
XLogP:	3.093
# Rotatable Bonds:	11
Polar Surface Area:	116.45
# H-Bond Aceptor:	1
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	32

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