NPASS Natural Product

Natural Product: NPC474417

Natural Product ID:	NPC474417
Common Name:	Deacetylvismione H
IUPAC Name:	3,8,9-trihydroxy-3-methyl-6-(3-methylbut-2-enoxy)-2,4-dihydroanthracen-1-one
Synonyms:	Deacetylvismione H
Molecular Formula:	C20H22O5
Standard InCHIKey:	PAHWTMPJUWLVGJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H22O5/c1-11(2)4-5-25-14-7-12-6-13-9-20(3,24)10-16(22)18(13)19(23)17(12)15(21)8-14/h4,6-8,21,23-24H,5,9-10H2,1-3H3
Canonical SMILES:	CC(=CCOc1cc(O)c2c(c1)cc1c(c2O)C(=O)CC(C1)(C)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
NPO10596	Vismia sp.	Species	Hypericaceae	Eukaryota				PMID[12828475]

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Biological Activity

Activity Type	# Activity
GI50	3

Activity Type	# Activity
Cell Line	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.6	ug/ml	22264149
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.6	ug/ml	10.6019/CHEMBL1201861
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.4	ug/ml	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 NPC474417 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	283
0.1-0.2	1284
0.2-0.3	2163
0.3-0.4	5421
0.4-0.5	7745
0.5-0.6	2589
0.6-0.7	3904
0.7-0.8	4164
0.8-0.85	1793
0.85-0.9	1313
0.9-0.95	206
0.95-1	24

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Similarity Score	Similarity Level	Natural Product ID
0.9045	High Similarity	NPC25361
0.9048	High Similarity	NPC227579
0.9048	High Similarity	NPC296917
0.9048	High Similarity	NPC324436
0.9048	High Similarity	NPC194432

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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 NPC474417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	964
0.2-0.3	1431
0.3-0.4	2451
0.4-0.5	2054
0.5-0.6	1160
0.6-0.7	551
0.7-0.8	182
0.8-0.85	37
0.85-0.9	20
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7216	Intermediate Similarity	NPD1729	Discontinued
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.723	Intermediate Similarity	NPD5691	Approved
0.7232	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2438	Suspended

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Structure

NPC474417 OpenBabel07101718282D 25 27 0 0 1 0 0 0 0 0999 V2000 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 1.7321 -2.0000 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 -1.7321 -2.0000 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 4.3301 -4.5000 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 -0.8660 -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 0.8660 -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 -2.5981 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -3.0981 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 20 1 0 0 0 0 4 5 1 0 0 0 0 4 11 2 0 0 0 0 5 25 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 8 15 2 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 19 2 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	13940837
ChEMBL	CHEMBL467619
ZINC

Physicochemical Properties

Molecular Weight:	342.15
ALogP:	0.2796
MLogP:	3.11
XLogP:	1.784
# Rotatable Bonds:	9
Polar Surface Area:	86.99
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	25

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