NPASS Natural Product

Natural Product: NPC68093

Natural Product ID:	NPC68093
Common Name:	Smeathxanthone A
IUPAC Name:	2-[(2E)-3,7-dimethylocta-2,6-dienyl]-1,3,5,8-tetrahydroxyxanthen-9-one
Synonyms:
Molecular Formula:	C23H24O6
Standard InCHIKey:	TWEXJIOSYZXWGT-NTUHNPAUSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-12(2)5-4-6-13(3)7-8-14-17(26)11-18-20(21(14)27)22(28)19-15(24)9-10-16(25)23(19)29-18/h5,7,9-11,24-27H,4,6,8H2,1-3H3/b13-7+
Canonical SMILES:	C/C(=CCc1c(O)cc2c(c1O)c(=O)c1c(o2)c(O)ccc1O)/CCC=C(C)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	UNPD*
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	UNPD*
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	UNPD*
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	UNPD*
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	UNPD*
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	UNPD*
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	UNPD*
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	UNPD*
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	UNPD*
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
IC50	1
Ki	2
Others	1

Activity Type	# Activity
Individual Protein	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	270	nM	20696581
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	150	nM	20696581
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	44.68	nM	20696581
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Activity	=	80.8	%	18558747

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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 NPC68093 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	330
0.1-0.2	1242
0.2-0.3	2706
0.3-0.4	6826
0.4-0.5	6165
0.5-0.6	2352
0.6-0.7	3390
0.7-0.8	4145
0.8-0.85	1752
0.85-0.9	1201
0.9-0.95	612
0.95-1	168

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Similarity Score	Similarity Level	Natural Product ID
0.947	High Similarity	NPC192083
0.947	High Similarity	NPC213896
0.9474	High Similarity	NPC276444
0.9474	High Similarity	NPC471985
0.9474	High Similarity	NPC470328

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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 NPC68093 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	905
0.2-0.3	1589
0.3-0.4	2661
0.4-0.5	1875
0.5-0.6	1077
0.6-0.7	500
0.7-0.8	157
0.8-0.85	31
0.85-0.9	17
0.9-0.95	4
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7039	Intermediate Similarity	NPD9268	Approved
0.7041	Intermediate Similarity	NPD7874	Approved
0.7041	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6798	Discontinued
0.7044	Intermediate Similarity	NPD411	Approved

Showing 1 to 5 of 200 entries

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Structure

CID68093 OpenBabel06191715402D 29 31 0 0 0 0 0 0 0 0999 V2000 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -6.9282 -0.0000 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 -4.3301 -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 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 -1.7321 -0.0000 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 -5.1962 -2.0000 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 1.7321 -2.0000 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 -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 0.8660 -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 -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 0.8660 -0.5000 0.0000 C 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 1.7321 1.0000 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 12 2 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 14 17 1 0 0 0 0 14 21 2 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 20 2 0 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 27 1 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11509473
ChEMBL	CHEMBL480158
ZINC

Physicochemical Properties

Molecular Weight:	396.16
ALogP:	0.8505
MLogP:	3.33
XLogP:	2.943
# Rotatable Bonds:	12
Polar Surface Area:	107.22
# H-Bond Aceptor:	1
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	29

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