NPASS Natural Product

Natural Product: NPC155198

Natural Product ID:	NPC155198
Common Name:	7,8-Seco-Para-Ferruginone
IUPAC Name:	2-[(1S,2S)-2-(3,6-dioxo-4-propan-2-ylcyclohexa-1,4-dien-1-yl)-2,6,6-trimethylcyclohexyl]acetaldehyde
Synonyms:
Molecular Formula:	C20H28O3
Standard InCHIKey:	JCLGBJLXHLKJPT-AZUAARDMSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-13(2)14-11-17(23)15(12-16(14)22)20(5)9-6-8-19(3,4)18(20)7-10-21/h10-13,18H,6-9H2,1-5H3/t18-,20+/m0/s1
Canonical SMILES:	O=CC[C@H]1C(C)(C)CCC[C@]1(C)C1=CC(=O)C(=CC1=O)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
NPO19148	Gouania tomentosa	Species	Gobiesocidae	Eukaryota	UNPD*
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	TCMID*
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	UNPD*
NPO21396	Spongia vermicularis	Species	Spongiidae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
MIC	2

Activity Type	# Activity
Organism	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	20000	nM	12141863
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	15000	nM	12141863

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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 NPC155198 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	93
0.1-0.2	1067
0.2-0.3	5803
0.3-0.4	11327
0.4-0.5	5945
0.5-0.6	4387
0.6-0.7	1795
0.7-0.8	401
0.8-0.85	47
0.85-0.9	21
0.9-0.95	3
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7468	Intermediate Similarity	NPC55869
0.747	Intermediate Similarity	NPC473229
0.747	Intermediate Similarity	NPC206060
0.75	Intermediate Similarity	NPC110725
0.75	Intermediate Similarity	NPC41539

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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 NPC155198 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	120
0.1-0.2	1624
0.2-0.3	4382
0.3-0.4	2214
0.4-0.5	432
0.5-0.6	244
0.6-0.7	112
0.7-0.8	28
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5769	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD5363	Approved
0.5778	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD6926	Approved
0.5783	Remote Similarity	NPD6924	Approved

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Structure

CID155198 OpenBabel06191715522D 23 24 0 0 1 0 0 0 0 0999 V2000 -3.9576 1.9212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3880 0.3150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3514 2.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3114 2.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1253 -0.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 2.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 -0.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1758 1.1758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7092 0.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7819 0.7454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9273 0.2485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1030 1.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6061 -0.4304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8314 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4942 3.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3515 2.3515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3576 -1.3576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 21 2 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	10018666
ChEMBL	CHEMBL455370
ZINC

Physicochemical Properties

Molecular Weight:	316.20
ALogP:	1.111
MLogP:	3.33
XLogP:	4.58
# Rotatable Bonds:	9
Polar Surface Area:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	23

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