NPASS Natural Product

Natural Product: NPC183181

Natural Product ID:	NPC183181
Common Name:	(+/-)-Threo-Guaiacylglycerol-Beta-O-4'-Coniferyl Ether
IUPAC Name:	(1S,2R)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenoxy]propane-1,3-diol
Synonyms:
Molecular Formula:	C20H24O7
Standard InCHIKey:	FYEZJIXULOZDRT-WGLWSTOQSA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-25-17-11-14(6-7-15(17)23)20(24)19(12-22)27-16-8-5-13(4-3-9-21)10-18(16)26-2/h3-8,10-11,19-24H,9,12H2,1-2H3/b4-3+/t19-,20+/m1/s1
Canonical SMILES:	OC/C=C/c1ccc(c(c1)OC)O[C@@H]([C@H](c1ccc(c(c1)OC)O)O)CO
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
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	leaves and twigs	PMID[21435874]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	PMID[19296617]
NPO9642	Brassica fruticulosa	Species	Brassicaceae	Eukaryota		PMID[14518939]

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Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
Others	1

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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	=	60900	nM	PubChem BioAssay data set
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	66400	nM	25682561

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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 NPC183181 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	248
0.1-0.2	1043
0.2-0.3	2456
0.3-0.4	6721
0.4-0.5	6721
0.5-0.6	2519
0.6-0.7	5101
0.7-0.8	4418
0.8-0.85	961
0.85-0.9	460
0.9-0.95	197
0.95-1	44

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Similarity Score	Similarity Level	Natural Product ID
0.9055	High Similarity	NPC270849
0.9055	High Similarity	NPC26653
0.9055	High Similarity	NPC212015
0.9062	High Similarity	NPC248307
0.9062	High Similarity	NPC65942

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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 NPC183181 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	839
0.2-0.3	1580
0.3-0.4	2608
0.4-0.5	1838
0.5-0.6	1037
0.6-0.7	727
0.7-0.8	265
0.8-0.85	15
0.85-0.9	5
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7172	Intermediate Similarity	NPD2156	Approved
0.7172	Intermediate Similarity	NPD2154	Approved
0.7172	Intermediate Similarity	NPD2155	Approved
0.7174	Intermediate Similarity	NPD6696	Suspended
0.7174	Intermediate Similarity	NPD2922	Phase 1

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Structure

NPC183181 OpenBabel07101718242D 27 28 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 2.5981 -1.5000 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 -0.0000 -2.0000 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 -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 3.4641 -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 -5.1962 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 0.8660 -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 -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 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 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 -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 -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 25 1 0 0 0 0 2 26 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 21 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 22 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 27 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 12 1 6 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 20 24 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	21577856
ChEMBL	CHEMBL560169
ZINC

Physicochemical Properties

Molecular Weight:	376.15
ALogP:	-1.7087
MLogP:	2.89
XLogP:	1.178
# Rotatable Bonds:	15
Polar Surface Area:	108.61
# H-Bond Aceptor:	3
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	27

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