NPASS Natural Product

Natural Product: NPC273538

Natural Product ID:	NPC273538
Common Name:	Icaritin
IUPAC Name:	3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
Synonyms:	Icaritin
Molecular Formula:	C21H20O6
Standard InCHIKey:	TUUXBSASAQJECY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O6/c1-11(2)4-9-14-15(22)10-16(23)17-18(24)19(25)20(27-21(14)17)12-5-7-13(26-3)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3
Canonical SMILES:	COc1ccc(cc1)c1oc2c(CC=C(C)C)c(O)cc(c2c(=O)c1O)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
NPO10214	Epimedium wanshanense	Species	Berberidaceae	Eukaryota	TCM_Taiwan*
NPO10214	Epimedium wanshanense	Species	Berberidaceae	Eukaryota	HerDing*
NPO10214	Epimedium wanshanense	Species	Berberidaceae	Eukaryota	TCMID*
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	TM-MC*
NPO12834	Radix polygoni multiflori preparata	Species	Lymnaeidae	Eukaryota	TCMID*
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	TM-MC*
NPO14204	Herba sarcandrae	NA	NA	NA	TCMSP*
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	TM-MC*
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	TCMID*
NPO17506	Semen pharbitidis	NA	NA	NA	TCMSP*

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Biological Activity

Activity Type	# Activity
IC50	6
Others	8

Activity Type	# Activity
Cell Line	3
Individual Protein	5
Others	6

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	21600	nM	26079090
NPT2	Others	Unspecified		Ratio IC50	=	2.48		19523827
NPT2	Others	Unspecified		Ratio IC50	=	4.96		19523827
NPT2	Others	Unspecified		Ratio IC50	=	12.89		19523827
NPT2	Others	Unspecified		FC	=	10		19523827
NPT2	Others	Unspecified		IC50	=	52090	nM	19523827
NPT2	Others	Unspecified		IC50	=	24900	nM	26079090
NPT273	Individual Protein	Phosphodiesterase 5A	Homo sapiens	IC50	=	2200	nM	18778098
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Inhibition	=	41.9	%	19523827
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000	nM	26079090

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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 NPC273538 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	267
0.1-0.2	1221
0.2-0.3	2381
0.3-0.4	5857
0.4-0.5	7261
0.5-0.6	2519
0.6-0.7	4019
0.7-0.8	3807
0.8-0.85	1505
0.85-0.9	1272
0.9-0.95	703
0.95-1	77

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Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC266572
0.9375	High Similarity	NPC145467
0.9375	High Similarity	NPC6511
0.9379	High Similarity	NPC476185
0.9379	High Similarity	NPC37348

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 NPC273538 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	900
0.2-0.3	1415
0.3-0.4	2423
0.4-0.5	2116
0.5-0.6	1241
0.6-0.7	526
0.7-0.8	169
0.8-0.85	44
0.85-0.9	22
0.9-0.95	8
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7143	Intermediate Similarity	NPD7447	Phase 1
0.7151	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD7199	Phase 2
0.717	Intermediate Similarity	NPD3887	Approved

Showing 1 to 5 of 200 entries

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Structure

CID273538 OpenBabel06191716082D 27 29 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 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 5.1962 1.0000 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 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 -1.7321 1.0000 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 -2.5981 2.5000 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 3.4641 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 -2.5981 -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 -0.8660 -1.5000 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 0.8660 -1.5000 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 -0.8660 -0.5000 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 1.7321 -2.0000 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 26 1 0 0 0 0 4 9 1 0 0 0 0 4 11 2 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 12 20 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 21 2 0 0 0 0 15 22 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 24 2 0 0 0 0 19 20 2 0 0 0 0 19 25 1 0 0 0 0 20 27 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5318980
ChEMBL	CHEMBL498485
ZINC

Physicochemical Properties

Molecular Weight:	368.13
ALogP:	-0.055
MLogP:	3.11
XLogP:	3.904
# Rotatable Bonds:	10
Polar Surface Area:	96.22
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	27

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