NPASS Natural Product

Natural Product: NPC69143

Natural Product ID:	NPC69143
Common Name:	Sagittine A
IUPAC Name:	(1S,4aR,4bS,7S,8aS)-7-ethenyl-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2H-phenanthrene-1-carboxylic acid
Synonyms:
Molecular Formula:	C20H30O2
Standard InCHIKey:	NVQMSTNGSLMEJX-ZESOOZHZSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-5-18(2)11-12-19(3)14(13-18)8-9-16-15(19)7-6-10-20(16,4)17(21)22/h5,9,14-15H,1,6-8,10-13H2,2-4H3,(H,21,22)/t14-,15-,18-,19-,20-/m0/s1
Canonical SMILES:	C=C[C@@]1(C)CC[C@]2([C@H](C1)CC=C1[C@@H]2CCC[C@]1(C)C(=O)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
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota				PMID[16499326]

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Biological Activity

Activity Type	# Activity
MIC	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
NPT1655	Organism	Actinobacillus actinomycetemcomitans	Aggregatibacter actinomycetemcomitans	MIC	>	250	ug/ml	22515429
NPT4399	Organism	Actinomyces naeslundii	Actinomyces naeslundii	MIC	=	62.5	ug/ml	22524636
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	62.5	ug/ml	23013356

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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 NPC69143 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	87
0.1-0.2	649
0.2-0.3	3114
0.3-0.4	10130
0.4-0.5	7160
0.5-0.6	4774
0.6-0.7	3430
0.7-0.8	1296
0.8-0.85	173
0.85-0.9	50
0.9-0.95	17
0.95-1	9

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Similarity Score	Similarity Level	Natural Product ID
0.8072	Intermediate Similarity	NPC262085
0.8072	Intermediate Similarity	NPC72638
0.8072	Intermediate Similarity	NPC322159
0.8072	Intermediate Similarity	NPC94666
0.8072	Intermediate Similarity	NPC264127

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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 NPC69143 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	117
0.1-0.2	1049
0.2-0.3	3590
0.3-0.4	2860
0.4-0.5	943
0.5-0.6	261
0.6-0.7	245
0.7-0.8	90
0.8-0.85	6
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
0.6429	Remote Similarity	NPD3173	Approved
0.6429	Remote Similarity	NPD4225	Approved
0.6449	Remote Similarity	NPD6868	Approved
0.6452	Remote Similarity	NPD6051	Approved
0.6456	Remote Similarity	NPD3171	Clinical (unspecified phase)

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Structure

NPC69143 OpenBabel07101719512D 22 24 0 0 1 0 0 0 0 0999 V2000 5.5549 2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1235 0.8912 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 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5889 2.4659 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 -1.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 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 2 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 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 16 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 1 0 0 0 15 16 1 0 0 0 0 15 19 1 1 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 2 1 6 0 0 0 19 3 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	11493191
ChEMBL	CHEMBL447656
ZINC

Physicochemical Properties

Molecular Weight:	302.22
ALogP:	1.6579
MLogP:	3.44
XLogP:	6.935
# Rotatable Bonds:	6
Polar Surface Area:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	22

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