NPASS Natural Product

Natural Product: NPC274784

Natural Product ID:	NPC274784
Common Name:	Isosakutanetin
IUPAC Name:	(2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:	Isosakuranetin; Isosakutanetin; Naringenin 4'-Methyl Ether
Molecular Formula:	C16H14O5
Standard InCHIKey:	HMUJXQRRKBLVOO-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1
Canonical SMILES:	COc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Collection Location	Reference
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota		TCM_Taiwan*
NPO11318	Eriodictyon californicum	Species	Namaceae	Eukaryota		PMID[1593282]
NPO32851	brazilian green propolis	Species	NA	NA	Brazil	PMID[21865046]
NPO33179	piper sp.	Species	Piperaceae	Eukaryota		PMID[15568762]

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Biological Activity

Activity Type	# Activity
IC50	4
Others	13
Potency	3

Activity Type	# Activity
Cell Line	3
Individual Protein	8
Organism	2
Others	7

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	0	%	3379415
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	2196	nM	20696580
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	1024	nM	20696580
NPT2	Others	Unspecified		IC50	>	100000	nM	18302333
NPT2	Others	Unspecified		Inhibition	=	-63	%	1593282
NPT2	Others	Unspecified		Inhibition	=	-28	%	1593282
NPT2	Others	Unspecified		Inhibition	=	-11	%	1593282
NPT2	Others	Unspecified		Activity	=	0		8882428
NPT2	Others	Unspecified		Inhibition	=	38.1	%	21865046
NPT2	Others	Unspecified		Potency		14125.4	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 NPC274784 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	234
0.1-0.2	1142
0.2-0.3	2339
0.3-0.4	5673
0.4-0.5	7548
0.5-0.6	2494
0.6-0.7	4109
0.7-0.8	3915
0.8-0.85	1538
0.85-0.9	1212
0.9-0.95	513
0.95-1	172

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Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC187282
0.9429	High Similarity	NPC474161
0.9429	High Similarity	NPC476153
0.9429	High Similarity	NPC299011
0.9433	High Similarity	NPC132592

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 NPC274784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	887
0.2-0.3	1379
0.3-0.4	2367
0.4-0.5	2171
0.5-0.6	1300
0.6-0.7	556
0.7-0.8	172
0.8-0.85	40
0.85-0.9	20
0.9-0.95	8
0.95-1	3

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7134	Intermediate Similarity	NPD7440	Discontinued
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD2353	Approved
0.7143	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6585	Discontinued

Showing 1 to 5 of 200 entries

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Structure

CID274784 OpenBabel06191716082D 21 23 0 0 1 0 0 0 0 0999 V2000 -5.1962 -1.0000 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 -2.5981 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 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 1.7321 -0.0000 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 -1.7321 0.0000 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 -3.4641 -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 -0.0000 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 1 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 3.4641 -0.0000 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 -0.0000 3.0000 0.0000 O 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 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 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 7 15 2 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 19 2 0 0 0 0 14 9 1 6 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	160481
ChEMBL	CHEMBL470266
ZINC

Physicochemical Properties

Molecular Weight:	286.08
ALogP:	-1.4059
MLogP:	2.67
XLogP:	1.416
# 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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