NPASS Natural Product

Natural Product: NPC188022

Natural Product ID:	NPC188022
Common Name:	(2R)-7,4'-Dihydroxy-5-Methoxy-8-Methylflavan
IUPAC Name:	(2R)-2-(4-hydroxyphenyl)-5-methoxy-8-methyl-3,4-dihydro-2H-chromen-7-ol
Synonyms:
Molecular Formula:	C17H18O4
Standard InCHIKey:	URQUSRJQNKCRCO-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-10-14(19)9-16(20-2)13-7-8-15(21-17(10)13)11-3-5-12(18)6-4-11/h3-6,9,15,18-19H,7-8H2,1-2H3/t15-/m1/s1
Canonical SMILES:	COc1cc(O)c(c2c1CC[C@@H](O2)c1ccc(cc1)O)C
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
NPO20812	Soymida febrifuga	Species	Meliaceae	Eukaryota		Myanmar		PMID[19689125]

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Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	3
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	74000	nM	18616221
NPT2	Others	Unspecified		IC50	=	89100	nM	19734910
NPT2	Others	Unspecified		IC50	=	59100	nM	27317644
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	37000	nM	12662097
NPT81	Cell Line	A549	Homo sapiens	IC50	=	35500	nM	20937542

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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 NPC188022 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	238
0.1-0.2	1055
0.2-0.3	2345
0.3-0.4	7269
0.4-0.5	6357
0.5-0.6	2564
0.6-0.7	4779
0.7-0.8	4720
0.8-0.85	1159
0.85-0.9	296
0.9-0.95	71
0.95-1	36

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Similarity Score	Similarity Level	Natural Product ID
0.8692	High Similarity	NPC202762
0.8692	High Similarity	NPC185604
0.8692	High Similarity	NPC78770
0.8692	High Similarity	NPC86655
0.8692	High Similarity	NPC261619

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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 NPC188022 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	864
0.2-0.3	1326
0.3-0.4	2587
0.4-0.5	1994
0.5-0.6	1145
0.6-0.7	735
0.7-0.8	244
0.8-0.85	20
0.85-0.9	4
0.9-0.95	4
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7143	Intermediate Similarity	NPD7741	Discontinued
0.7143	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7095	Approved
0.7153	Intermediate Similarity	NPD2799	Discontinued

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Structure

NPC188022 OpenBabel07101718302D 21 23 0 0 1 0 0 0 0 0999 V2000 -1.7321 1.0000 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 1.7321 1.0000 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 2.5981 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 -0.0000 -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 -2.5981 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 -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 2 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 -0.8660 -0.5000 0.0000 C 0 0 0 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 -3.4641 -0.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 20 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 17 2 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 15 11 1 1 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44479223
ChEMBL	CHEMBL1080978
ZINC

Physicochemical Properties

Molecular Weight:	286.12
ALogP:	-0.7605
MLogP:	2.89
XLogP:	2.601
# Rotatable Bonds:	6
Polar Surface Area:	58.92
# H-Bond Aceptor:	0
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	21

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