NPASS Natural Product

Natural Product: NPC472969

Natural Product ID:	NPC472969
Common Name:	Threo-Guaiacylglycerol-8'-Vanillic Acid Ether
IUPAC Name:	4-[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxybenzoic acid
Synonyms:
Molecular Formula:	C18H20O8
Standard InCHIKey:	UDFDXTXZIMXARD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H20O8/c1-24-14-7-10(3-5-12(14)20)17(21)16(9-19)26-13-6-4-11(18(22)23)8-15(13)25-2/h3-8,16-17,19-21H,9H2,1-2H3,(H,22,23)
Canonical SMILES:	OCC(C(c1ccc(c(c1)OC)O)O)Oc1ccc(cc1OC)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
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	Fruits			PMID[26110443]

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Biological Activity

Activity Type	# Activity
IC50	3
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	10000	nM	17461599
NPT2	Others	Unspecified		IC50	=	8400	nM	25226228
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	>	35000	nM	25922181
NPT616	Cell Line	MDCK	Canis lupus familiaris	TC50	=	100	nM	PubChem BioAssay data set

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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 NPC472969 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	236
0.1-0.2	985
0.2-0.3	2191
0.3-0.4	5040
0.4-0.5	7181
0.5-0.6	3369
0.6-0.7	3314
0.7-0.8	5965
0.8-0.85	2022
0.85-0.9	520
0.9-0.95	58
0.95-1	8

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Similarity Score	Similarity Level	Natural Product ID
0.8707	High Similarity	NPC192831
0.8707	High Similarity	NPC258469
0.8707	High Similarity	NPC277315
0.8707	High Similarity	NPC43158
0.871	High Similarity	NPC476410

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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 NPC472969 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	791
0.2-0.3	1570
0.3-0.4	2366
0.4-0.5	2079
0.5-0.6	1165
0.6-0.7	700
0.7-0.8	194
0.8-0.85	35
0.85-0.9	8
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7107	Intermediate Similarity	NPD2424	Discontinued
0.7107	Intermediate Similarity	NPD5958	Discontinued
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6873	Phase 2
0.7117	Intermediate Similarity	NPD5049	Phase 3

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Structure

NPC472969 OpenBabel07101719132D 26 27 0 0 1 0 0 0 0 0999 V2000 -6.9282 1.0000 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 -0.0000 -2.0000 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 -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 0.8660 -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 -4.3301 -0.5000 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 -6.0622 -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 -6.0622 -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 -2.5981 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 3 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 -1.7321 -2.0000 0.0000 O 0 0 0 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 -3.4641 1.0000 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 2.5981 -1.5000 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 0.0000 1.0000 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 24 1 0 0 0 0 2 25 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 9 19 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 26 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	13607390
ChEMBL	CHEMBL3594249
ZINC

Physicochemical Properties

Molecular Weight:	364.12
ALogP:	-1.9676
MLogP:	2.56
XLogP:	0.669
# Rotatable Bonds:	14
Polar Surface Area:	125.68
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	26

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