NPASS Natural Product

Natural Product: NPC13818

Natural Product ID:	NPC13818
Common Name:	n.a.
IUPAC Name:
Synonyms:	3,5-Dicaffeoyl Quinic Acid; 3,5-Dicaffeoylquinic Acid; 3,5-Dicaffeoylquinicacid; Rel-3,5-Dicaffeoylquinic Acid
Molecular Formula:	C25H24O12
Standard InCHIKey:	KRZBCHWVBQOTNZ-PSEXTPKNSA-N
Standard InCHI:	InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
Canonical SMILES:	O=C(O[C@@H]1C[C@@](O)(C[C@H]([C@H]1O)OC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
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
NPO10374	Dichrocephala bicolor	Species	Asteraceae	Eukaryota		PMID[10096846]
NPO10374	Dichrocephala bicolor	Species	Asteraceae	Eukaryota	Whole Plants	DOI[10.1021/np980153o]
NPO1049	Tethya amamensis	Species	Tethyidae	Eukaryota		UNPD*
NPO10946	Scedosporium boydii	Species	Microascaceae	Eukaryota		UNPD*
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota		UNPD*
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota		UNPD*
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota		TCM_Taiwan*
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota		UNPD*
NPO117	Acacia armata	Species	Fabaceae	Eukaryota		UNPD*
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota		UNPD*

Showing 1 to 10 of 121 entries

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Biological Activity

Activity Type	# Activity
EC50	1
ED50	3
IC50	21
LD50	1
Others	24

Activity Type	# Activity
Cell Line	6
Individual Protein	8
Organism	15
Others	19
Protein Family	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	5.6	ug/ml	16643034
NPT1	Others	Radical scavenging activity		EC50	=	16	ug/ml	20004585
NPT1	Others	Radical scavenging activity		IC50	=	32400	nM	23356964
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	20	%	21469692
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	42	%	21469692
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	97	%	21469692
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	1300	nM	9986720
NPT1270	Individual Protein	Aldo-keto reductase family 1 member B10	Homo sapiens	IC50	=	130	nM	22236472
NPT2	Others	Unspecified		IC50	=	666000	nM	2822857
NPT2	Others	Unspecified		IC50	=	85900	nM	2822857

Showing 1 to 10 of 48 entries

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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 NPC13818 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	255
0.1-0.2	961
0.2-0.3	2150
0.3-0.4	4650
0.4-0.5	7046
0.5-0.6	4621
0.6-0.7	5222
0.7-0.8	5513
0.8-0.85	336
0.85-0.9	70
0.9-0.95	28
0.95-1	37

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Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC472859
0.8333	Intermediate Similarity	NPC25389
0.8333	Intermediate Similarity	NPC78363
0.8333	Intermediate Similarity	NPC478242
0.8333	Intermediate Similarity	NPC260425

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 NPC13818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	759
0.2-0.3	1585
0.3-0.4	2644
0.4-0.5	2070
0.5-0.6	1193
0.6-0.7	549
0.7-0.8	93
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6667	Remote Similarity	NPD2982	Phase 2
0.6685	Remote Similarity	NPD8360	Approved
0.6685	Remote Similarity	NPD8361	Approved
0.6686	Remote Similarity	NPD7229	Phase 3
0.6687	Remote Similarity	NPD1652	Phase 2

Showing 1 to 5 of 200 entries

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Structure

CID13818 OpenBabel06191715342D 37 39 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 4.3301 3.5000 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 3.4641 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 4.3301 4.5000 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 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 0.8660 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 3.4641 3.0000 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 3.4641 5.0000 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 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 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 2 0 0 0 0 0 0 0 0 0 -0.5000 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 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 3.4641 6.0000 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 1.7321 5.0000 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 3.4641 0.0000 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 -1.5000 2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.8660 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 13 1 0 0 0 0 2 6 2 0 0 0 0 2 14 1 0 0 0 0 3 7 2 0 0 0 0 3 13 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 11 25 1 0 0 0 0 12 20 1 0 0 0 0 12 25 1 0 0 0 0 15 17 2 0 0 0 0 15 26 1 0 0 0 0 16 18 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 23 1 0 0 0 0 19 36 1 6 0 0 0 20 23 1 0 0 0 0 20 37 1 1 0 0 0 21 30 2 0 0 0 0 21 36 1 0 0 0 0 22 31 2 0 0 0 0 22 37 1 0 0 0 0 23 32 1 6 0 0 0 24 25 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 25 35 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID
ChEMBL	CHEMBL249447
ZINC

Physicochemical Properties

Molecular Weight:	516.13
ALogP:	-2.3865
MLogP:	2.89
XLogP:	1.085
# Rotatable Bonds:	16
Polar Surface Area:	211.28
# H-Bond Aceptor:	8
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	37

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