NPASS Natural Product

Natural Product: NPC32006

Natural Product ID:	NPC32006
Common Name:	Rezishanone C
IUPAC Name:	(1S,2S,4R,6E,8S)-8-ethoxy-2-hydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dienylidene]-2,4-dimethylbicyclo[2.2.2]octane-3,5-dione
Synonyms:	Rezishanone C
Molecular Formula:	C18H24O5
Standard InCHIKey:	OYVREVFYRWCTER-GXMVIZQESA-N
Standard InCHI:	InChI=1S/C18H24O5/c1-5-7-8-9-12(19)14-11-10-13(23-6-2)17(3,15(14)20)16(21)18(11,4)22/h5,7-9,11,13,19,22H,6,10H2,1-4H3/b7-5+,9-8+,14-12+/t11-,13-,17+,18-/m0/s1
Canonical SMILES:	C/C=C/C=C/C(=C1/[C@@H]2C[C@@H]([C@](C1=O)(C(=O)[C@@]2(C)O)C)OCC)/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
NPO32492	penicillium notatum	Species	Aspergillaceae	Eukaryota				PMID[15974609]

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Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Organism	3

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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	IZ	=	12	mm	17844994
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	13	mm	23891163
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12	mm	DrugMatrix in vitro pharmacology data

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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 NPC32006 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	160
0.1-0.2	773
0.2-0.3	2490
0.3-0.4	4689
0.4-0.5	8700
0.5-0.6	8689
0.6-0.7	4282
0.7-0.8	1090
0.8-0.85	13
0.85-0.9	1
0.9-0.95	1
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.75	Intermediate Similarity	NPC99380
0.75	Intermediate Similarity	NPC168027
0.75	Intermediate Similarity	NPC478216
0.75	Intermediate Similarity	NPC185936
0.75	Intermediate Similarity	NPC35751

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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 NPC32006 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1135
0.2-0.3	3195
0.3-0.4	2839
0.4-0.5	1205
0.5-0.6	376
0.6-0.7	174
0.7-0.8	69
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.625	Remote Similarity	NPD8513	Phase 3
0.625	Remote Similarity	NPD8516	Approved
0.625	Remote Similarity	NPD8517	Approved
0.625	Remote Similarity	NPD8515	Approved
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)

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Structure

NPC32006 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 -5.1488 0.0527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1605 -2.8257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0596 -2.2622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9568 -0.0717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3178 0.5325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3295 -2.3459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4869 0.0527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6560 0.5325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8251 0.0527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4986 0.0527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6677 0.5325 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9942 0.5325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4986 -0.9067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1632 0.0527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1632 -0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.8540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6677 -1.3865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9942 1.4919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8251 -1.8662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8644 -1.2703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5405 0.7927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3295 -1.3865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 5 7 2 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 12 1 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 1 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 17 1 6 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 3 1 1 0 0 0 18 4 1 6 0 0 0 18 22 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44584011
ChEMBL	CHEMBL465811
ZINC

Physicochemical Properties

Molecular Weight:	320.16
ALogP:	0.8926
MLogP:	2.89
XLogP:	1.973
# Rotatable Bonds:	10
Polar Surface Area:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	23

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