NPASS Natural Product

Natural Product: NPC176229

Natural Product ID:	NPC176229
Common Name:	Obovatin
IUPAC Name:	(2S)-5-hydroxy-8,8-dimethyl-2-phenyl-2,3-dihydropyrano[2,3-h]chromen-4-one
Synonyms:	Obovatin
Molecular Formula:	C20H18O4
Standard InCHIKey:	VYVZELWVPQMZDE-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C20H18O4/c1-20(2)9-8-13-17(24-20)11-15(22)18-14(21)10-16(23-19(13)18)12-6-4-3-5-7-12/h3-9,11,16,22H,10H2,1-2H3/t16-/m0/s1
Canonical SMILES:	O=C1C[C@H](Oc2c1c(O)cc1c2C=CC(O1)(C)C)c1ccccc1
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
NPO17729	Tephrosia toxicaria	Species	Geometridae	Eukaryota		TCMID*
NPO28882	Misopates orontium	Species	Plantaginaceae	Eukaryota		UNPD*
NPO28901	Blighia sapida	Species	Sapindaceae	Eukaryota		UNPD*
NPO29014	Dalea boliviana	Species	Fabaceae	Eukaryota	Root	PMID[21226489]
NPO29032	Spathiphyllum wallisii	Species	Araceae	Eukaryota		UNPD*
NPO29456	Theobroma grandiflorum	Species	Malvaceae	Eukaryota		UNPD*
NPO31060	Tephrosia	Genus	Geometridae	Eukaryota		PMID[21226489]

Showing 1 to 7 of 7 entries

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Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Individual Protein	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	16.2	%	21226489

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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 NPC176229 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	254
0.1-0.2	1150
0.2-0.3	2120
0.3-0.4	5588
0.4-0.5	7720
0.5-0.6	2705
0.6-0.7	4146
0.7-0.8	3740
0.8-0.85	1622
0.85-0.9	1109
0.9-0.95	522
0.95-1	213

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Similarity Score	Similarity Level	Natural Product ID
0.9507	High Similarity	NPC271288
0.9507	High Similarity	NPC124780
0.9507	High Similarity	NPC224714
0.9507	High Similarity	NPC311741
0.9507	High Similarity	NPC87486

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 NPC176229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	878
0.2-0.3	1383
0.3-0.4	2370
0.4-0.5	2207
0.5-0.6	1266
0.6-0.7	544
0.7-0.8	175
0.8-0.85	42
0.85-0.9	16
0.9-0.95	11
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7697	Approved
0.7151	Intermediate Similarity	NPD7435	Discontinued
0.7151	Intermediate Similarity	NPD7698	Approved
0.7151	Intermediate Similarity	NPD7696	Phase 3

Showing 1 to 5 of 200 entries

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Structure

CID176229 OpenBabel06191715552D 24 27 0 0 1 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 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 6.0622 -1.5000 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 5.1962 -1.0000 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 1.7321 -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 0.8660 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 1.7321 -0.0000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 1 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 2.5981 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 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 3.4641 -0.0000 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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 21 2 0 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 12 1 1 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	13940733
ChEMBL	CHEMBL1689204
ZINC

Physicochemical Properties

Molecular Weight:	322.12
ALogP:	0.014
MLogP:	3.22
XLogP:	3.893
# Rotatable Bonds:	4
Polar Surface Area:	55.76
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	24

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