NPASS Natural Product

Natural Product: NPC109083

Natural Product ID:	NPC109083
Common Name:	Curcumin
IUPAC Name:	(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
Synonyms:	CI-75300; Curcumin; Diferuloylmethane; E100; Natural Yellow 3
Molecular Formula:	C21H20O6
Standard InCHIKey:	ZIUSSTSXXLLKKK-KOBPDPAPSA-N
Standard InCHI:	InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-13,22,24-25H,1-2H3/b7-3+,8-4+,16-13-
Canonical SMILES:	COc1cc(/C=C/C(=C/C(=O)/C=C/c2ccc(c(c2)OC)O)/O)ccc1O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO1505	Amomum tsao-ko	Species	Zingiberaceae	Eukaryota		TCMSP*
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota		TCM_Taiwan*
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		PMID[12350137]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	PMID[12617587]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		TCM_Taiwan*
NPO25160	Goniothalamus borneensis	Species	Annonaceae	Eukaryota		UNPD*
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota		TCM_Taiwan*
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota		TCM_Taiwan*
NPO31101	Acarus calamus	Species	Acaridae	Eukaryota		TCM_Taiwan*
NPO3251	Jacobaea maritima	Species	Asteraceae	Eukaryota		UNPD*

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Biological Activity

Activity Type	# Activity
EC50	48
ED50	10
GI50	10
IC50	416
Kd	3
Ki	21
MIC	45
Others	531
Potency	89

Activity Type	# Activity
Cell Line	388
Individual Protein	245
Organism	195
Others	331
Protein Complex	3
Protein Family	3
Protein-Protein Interaction	6
Tissue	2

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Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity	IC50	=	109740	nM	19359068
NPT1	Others	Radical scavenging activity	Activity	=	35	%	21190861
NPT1	Others	Radical scavenging activity	EC50	=	22600	nM	21601463
NPT1	Others	Radical scavenging activity	Activity	=	10	%	21601463
NPT1	Others	Radical scavenging activity	EC50	=	13000	nM	22029378
NPT1	Others	Radical scavenging activity	IC50	=	35100	nM	22884407
NPT1	Others	Radical scavenging activity	Activity	=	35	%	22126405
NPT1	Others	Radical scavenging activity	IC50	=	35100	nM	22995623
NPT1	Others	Radical scavenging activity	IC50	=	26500	nM	23357628
NPT1	Others	Radical scavenging activity	Activity	=	0.3	%	23357628

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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 NPC109083 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	180
0.1-0.2	1159
0.2-0.3	2881
0.3-0.4	8402
0.4-0.5	4564
0.5-0.6	2826
0.6-0.7	6404
0.7-0.8	3785
0.8-0.85	474
0.85-0.9	148
0.9-0.95	56
0.95-1	10

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Similarity Score	Similarity Level	Natural Product ID
0.8559	High Similarity	NPC33749
0.856	High Similarity	NPC28730
0.856	High Similarity	NPC17837
0.856	High Similarity	NPC214406
0.856	High Similarity	NPC18924

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 NPC109083 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	912
0.2-0.3	1327
0.3-0.4	2657
0.4-0.5	2018
0.5-0.6	1155
0.6-0.7	751
0.7-0.8	131
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6853	Remote Similarity	NPD4536	Approved
0.6857	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD37	Approved
0.6871	Remote Similarity	NPD2354	Approved
0.6875	Remote Similarity	NPD6032	Approved

Showing 1 to 5 of 200 entries

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Structure

CID109083 OpenBabel06191715462D 27 28 0 0 0 0 0 0 0 0999 V2000 10.3923 -3.0000 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 6.9282 -2.0000 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 7.7942 -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 6.0622 -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 8.6603 -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 8.6603 -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 4.3301 -1.5000 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 0.8660 -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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -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 9.5263 -1.5000 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 5.1962 -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 10.3923 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 7 2 0 0 0 0 3 14 1 0 0 0 0 4 8 2 0 0 0 0 4 15 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 14 2 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 16 22 1 0 0 0 0 17 23 2 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 21 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5281767
ChEMBL	CHEMBL116438
ZINC

Physicochemical Properties

Molecular Weight:	368.13
ALogP:	-0.6611
MLogP:	3.11
XLogP:	2.955
# Rotatable Bonds:	12
Polar Surface Area:	96.22
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	27

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