NPASS Natural Product

Natural Product: NPC145425

Natural Product ID:	NPC145425
Common Name:	4-O-Caffeoyl-3-O-Syringoyl Quinic Acid
IUPAC Name:	(1S,3S,4R,5S)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3-dihydroxy-5-(4-hydroxy-3,5-dimethoxybenzoyl)oxycyclohexane-1-carboxylic acid
Synonyms:
Molecular Formula:	C25H26O13
Standard InCHIKey:	PYGQEDZSTFIHHP-FXSUHYAKSA-N
Standard InCHI:	InChI=1S/C25H26O13/c1-35-17-8-13(9-18(36-2)21(17)30)23(31)37-19-11-25(34,24(32)33)10-16(28)22(19)38-20(29)6-4-12-3-5-14(26)15(27)7-12/h3-9,16,19,22,26-28,30,34H,10-11H2,1-2H3,(H,32,33)/b6-4+/t16-,19-,22+,25-/m0/s1
Canonical SMILES:	COc1cc(cc(c1O)OC)C(=O)O[C@H]1C[C@@](O)(C[C@@H]([C@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)C(=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	Collection Location	Collection Time	Reference
NPO32755	erycibe hainanesis	Species	Convolvulaceae	Eukaryota	roots and stems	Hainan Province, China	2008-MAR	PMID[20092289]

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Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	42.2	%	Open TG-GATES in vivo data: Organ Weight

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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 NPC145425 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	275
0.1-0.2	1112
0.2-0.3	2440
0.3-0.4	5498
0.4-0.5	6957
0.5-0.6	3260
0.6-0.7	3373
0.7-0.8	5656
0.8-0.85	1715
0.85-0.9	541
0.9-0.95	55
0.95-1	7

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Similarity Score	Similarity Level	Natural Product ID
0.8696	High Similarity	NPC249181
0.8701	High Similarity	NPC474903
0.8704	High Similarity	NPC20237
0.8707	High Similarity	NPC233350
0.8707	High Similarity	NPC18646

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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 NPC145425 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	826
0.2-0.3	1708
0.3-0.4	2578
0.4-0.5	1929
0.5-0.6	1142
0.6-0.7	514
0.7-0.8	139
0.8-0.85	29
0.85-0.9	10
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6933	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2799	Discontinued
0.6946	Remote Similarity	NPD7440	Discontinued
0.6947	Remote Similarity	NPD7700	Phase 2
0.6947	Remote Similarity	NPD7699	Phase 2

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Structure

NPC145425 OpenBabel07101719132D 38 40 0 0 1 0 0 0 0 0999 V2000 -2.5981 4.5000 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 4.3301 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 5.1962 2.0000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 -1.7321 -0.0000 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 -0.0000 3.0000 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 6.0622 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 1 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 1 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 -0.0000 5.0000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 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 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 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 -1.7321 -2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -1.0000 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 1.7321 5.0000 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 1 35 1 0 0 0 0 2 36 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 14 1 0 0 0 0 6 20 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 18 2 0 0 0 0 10 16 1 0 0 0 0 10 25 1 0 0 0 0 11 19 1 0 0 0 0 11 25 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 22 1 0 0 0 0 16 28 1 1 0 0 0 17 21 2 0 0 0 0 17 35 1 0 0 0 0 18 21 1 0 0 0 0 18 36 1 0 0 0 0 19 22 1 0 0 0 0 19 37 1 6 0 0 0 20 29 2 0 0 0 0 20 38 1 0 0 0 0 21 30 1 0 0 0 0 22 38 1 6 0 0 0 23 31 2 0 0 0 0 23 37 1 0 0 0 0 24 25 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 34 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	46185596
ChEMBL	CHEMBL1088452
ZINC

Physicochemical Properties

Molecular Weight:	534.14
ALogP:	-2.3909
MLogP:	2.78
XLogP:	0.126
# Rotatable Bonds:	18
Polar Surface Area:	209.51
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	38

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