NPASS Natural Product

Natural Product: NPC299520

Natural Product ID:	NPC299520
Common Name:	(3R)-Violanone
IUPAC Name:	(3R)-7-hydroxy-3-(3-hydroxy-2,4-dimethoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Molecular Formula:	C17H16O6
Standard InCHIKey:	ILOKNKKFXJKHMB-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C17H16O6/c1-21-13-6-5-10(17(22-2)16(13)20)12-8-23-14-7-9(18)3-4-11(14)15(12)19/h3-7,12,18,20H,8H2,1-2H3/t12-/m0/s1
Canonical SMILES:	COc1c(ccc(c1O)OC)[C@@H]1COc2c(C1=O)ccc(c2)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
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood			PMID[23743282]

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Biological Activity

Activity Type	# Activity
IC50	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		IC50	>	100000	nM	10.6019/CHEMBL1201861

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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 NPC299520 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	305
0.1-0.2	1148
0.2-0.3	2252
0.3-0.4	5547
0.4-0.5	7292
0.5-0.6	2617
0.6-0.7	3101
0.7-0.8	4360
0.8-0.85	1962
0.85-0.9	1502
0.9-0.95	736
0.95-1	67

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Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC228785
0.9355	High Similarity	NPC476980
0.9355	High Similarity	NPC119209
0.9355	High Similarity	NPC192686
0.9355	High Similarity	NPC287328

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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 NPC299520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	873
0.2-0.3	1534
0.3-0.4	2515
0.4-0.5	1965
0.5-0.6	1130
0.6-0.7	576
0.7-0.8	188
0.8-0.85	28
0.85-0.9	25
0.9-0.95	8
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.711	Intermediate Similarity	NPD4288	Approved
0.7115	Intermediate Similarity	NPD3267	Approved
0.7115	Intermediate Similarity	NPD3266	Approved
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.7134	Intermediate Similarity	NPD2424	Discontinued

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Structure

NPC299520 OpenBabel07101718232D 23 25 0 0 1 0 0 0 0 0999 V2000 -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 5.1962 -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 0.8660 -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 4.3301 1.5000 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 5.1962 1.0000 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 3.4641 -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 1 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 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 -0.8660 -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 6.0622 1.5000 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 -1.7321 -0.0000 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 -0.0000 1.0000 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 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 11 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 13 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 23 1 0 0 0 0 9 18 1 0 0 0 0 10 17 2 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 10 1 6 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	73353540
ChEMBL	CHEMBL2397766
ZINC

Physicochemical Properties

Molecular Weight:	316.09
ALogP:	-1.5752
MLogP:	2.67
XLogP:	0.805
# Rotatable Bonds:	7
Polar Surface Area:	85.22
# H-Bond Aceptor:	1
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	23

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