NPASS Natural Product

Natural Product: NPC174314

Natural Product ID:	NPC174314
Common Name:	Cinnamodial
IUPAC Name:	[(1R,4S,4aS,8aS)-3,4-diformyl-4-hydroxy-4a,8,8-trimethyl-5,6,7,8a-tetrahydro-1H-naphthalen-1-yl] acetate
Synonyms:	NSC-277293
Molecular Formula:	C17H24O5
Standard InCHIKey:	UKLMEFSRPRDOLD-YQFWSFKMSA-N
Standard InCHI:	InChI=1S/C17H24O5/c1-11(20)22-13-8-12(9-18)17(21,10-19)16(4)7-5-6-15(2,3)14(13)16/h8-10,13-14,21H,5-7H2,1-4H3/t13-,14+,16+,17-/m1/s1
Canonical SMILES:	O=CC1=C[C@@H](OC(=O)C)[C@@H]2[C@]([C@@]1(O)C=O)(C)CCCC2(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
NPO14437	Rimularia gibbosa	Species	Trapeliaceae	Eukaryota	UNPD*
NPO22984	Aframomum sceptrum	Species	Zingiberaceae	Eukaryota	UNPD*
NPO23467	Lobaria scrobiculata	Species	Lobariaceae	Eukaryota	UNPD*
NPO33473	capsicodendron dinisii	Species	Canellaceae	Eukaryota	PMID[7400822]
NPO4929	Pyropia perforata	Species	Bangiaceae	Eukaryota	UNPD*
NPO7432	Pleodendron costaricense	Species	Canellaceae	Eukaryota	PMID[16872133]
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	Eukaryota	PMID[17286431]

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Biological Activity

Activity Type	# Activity
ED50	1
IC50	3
MIC	32
Others	1

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Organism	30
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	MIC	>	2060	nM	17286431
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100	ug/ml	8254349
NPT165	Cell Line	HeLa	Homo sapiens	MIC	=	10310	nM	17286431
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.2	ug/ml	7400822
NPT1766	Organism	Human herpesvirus 1 strain KOS	Human herpesvirus 1 strain KOS	MIC	>	2060	nM	17286431
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100	ug/ml	8254349
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100	ug/ml	8254349
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MIC	>	2060	nM	17286431
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	MIC	>	2060	nM	17286431
NPT2	Others	Unspecified		IC50	=	580	nM	17286431

Showing 1 to 10 of 35 entries

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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 NPC174314 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	147
0.1-0.2	775
0.2-0.3	2827
0.3-0.4	5797
0.4-0.5	9511
0.5-0.6	5625
0.6-0.7	4639
0.7-0.8	1527
0.8-0.85	38
0.85-0.9	1
0.9-0.95	2
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7619	Intermediate Similarity	NPC303559
0.7619	Intermediate Similarity	NPC244456
0.7619	Intermediate Similarity	NPC469851
0.7619	Intermediate Similarity	NPC310981
0.7619	Intermediate Similarity	NPC472637

Showing 1 to 5 of 200 entries

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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 NPC174314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1305
0.2-0.3	3465
0.3-0.4	2675
0.4-0.5	1010
0.5-0.6	287
0.6-0.7	190
0.7-0.8	76
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
0.6371	Remote Similarity	NPD8513	Phase 3
0.6372	Remote Similarity	NPD5344	Discontinued
0.64	Remote Similarity	NPD3617	Approved
0.64	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5208	Approved

Showing 1 to 5 of 200 entries

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Structure

CID174314 OpenBabel06191715552D 22 23 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 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 2.5981 -0.5000 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 -0.8660 -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 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 0.8660 -0.5000 0.0000 C 0 0 2 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 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 1 11 1 0 0 0 0 2 15 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 18 2 0 0 0 0 10 17 1 0 0 0 0 10 19 2 0 0 0 0 11 20 2 0 0 0 0 11 22 1 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 6 0 0 0 14 15 1 0 0 0 0 14 16 1 6 0 0 0 16 17 1 1 0 0 0 17 21 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	442354
ChEMBL	CHEMBL373458
ZINC

Physicochemical Properties

Molecular Weight:	308.16
ALogP:	-0.0971
MLogP:	2.78
XLogP:	3.144
# Rotatable Bonds:	9
Polar Surface Area:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	22

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