NPASS Natural Product

Natural Product: NPC241498

Natural Product ID:	NPC241498
Common Name:	Hispidulin
IUPAC Name:	5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxychromen-4-one
Synonyms:	NSC-122415; TCMDC-123942
Molecular Formula:	C16H12O6
Standard InCHIKey:	IHFBPDAQLQOCBX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-21-16-11(19)7-13-14(15(16)20)10(18)6-12(22-13)8-2-4-9(17)5-3-8/h2-7,17,19-20H,1H3
Canonical SMILES:	COc1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)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
NPO10051	Phyla nodiflora	Species	Verbenaceae	Eukaryota	UNPD*
NPO10196	Echinocereus blanckii	Species	Cactaceae	Eukaryota	UNPD*
NPO10826	Rabdosia weisiensis	Species	Lamiaceae	Eukaryota	UNPD*
NPO10889	Heterochordaria abietina	NA	NA	NA	UNPD*
NPO11189	Anabaena sphaerica	Species	Nostocaceae	Bacteria	UNPD*
NPO11318	Eriodictyon californicum	Species	Namaceae	Eukaryota	PMID[1593282]
NPO11437	Alluaudia ascendens	Species	Didiereaceae	Eukaryota	UNPD*
NPO11546	Ledebouria floribunda	Species	Hyacinthaceae	Eukaryota	UNPD*
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	TM-MC*
NPO11698	Drosera spatulata	Species	Droseraceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
AC50	1
EC50	3
ED50	22
GI50	59
IC50	10
Ki	3
MIC	3
Others	19
Potency	30

Activity Type	# Activity
Cell Line	76
Individual Protein	34
Organism	12
Others	23
Protein Complex	1
Protein-Protein Interaction	1
Tissue	1
Uncleic Acid	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	17.6	ug/ml	7931367
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	20	ug/ml	10579870
NPT111	Cell Line	K562	Homo sapiens	GI50		34753.62	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		25351.29	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		24490.63	nM	PubChem BioAssay data set
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	IC50	=	2710	nM	26275107
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	Ki	=	1610	nM	8576921
NPT1316	Individual Protein	Adenosine A2a receptor	Rattus norvegicus	Ki	=	6480	nM	8576921
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	1.2	ug/ml	10579870
NPT1380	Individual Protein	Avian myoblastosis virus polyprotein II	Avian myeloblastosis virus	Inhibition	=	23.3	%	10.1007/s00044-011-9570-z

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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 NPC241498 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	318
0.1-0.2	1295
0.2-0.3	3014
0.3-0.4	7108
0.4-0.5	5632
0.5-0.6	2372
0.6-0.7	3515
0.7-0.8	4020
0.8-0.85	1757
0.85-0.9	1122
0.9-0.95	508
0.95-1	228

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Similarity Score	Similarity Level	Natural Product ID
0.9533	High Similarity	NPC191146
0.9533	High Similarity	NPC100916
0.9533	High Similarity	NPC55619
0.9533	High Similarity	NPC200388
0.9533	High Similarity	NPC268161

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 NPC241498 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	898
0.2-0.3	1707
0.3-0.4	2679
0.4-0.5	1791
0.5-0.6	1058
0.6-0.7	494
0.7-0.8	135
0.8-0.85	33
0.85-0.9	17
0.9-0.95	5
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6962	Remote Similarity	NPD1296	Phase 2
0.697	Remote Similarity	NPD2354	Approved
0.6977	Remote Similarity	NPD2296	Approved
0.698	Remote Similarity	NPD9493	Approved
0.6981	Remote Similarity	NPD1558	Phase 1

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Structure

CID241498 OpenBabel06191716042D 22 24 0 0 0 0 0 0 0 0999 V2000 0.8660 -1.5000 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 -4.3301 2.5000 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 -5.1962 3.0000 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 -0.8660 1.5000 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 -6.0622 2.5000 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 -3.4641 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 -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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 4 1 0 0 0 0 2 8 2 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 18 2 0 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5281628
ChEMBL	CHEMBL293776
ZINC

Physicochemical Properties

Molecular Weight:	300.06
ALogP:	-1.9363
MLogP:	2.56
XLogP:	1.123
# Rotatable Bonds:	6
Polar Surface Area:	96.22
# H-Bond Aceptor:	1
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	22

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