NPASS Natural Product

Natural Product: NPC298339

Natural Product ID:	NPC298339
Common Name:	Sinomenine
IUPAC Name:
Synonyms:	Sinomenine
Molecular Formula:	C19H23NO4
Standard InCHIKey:	INYYVPJSBIVGPH-QHRIQVFBSA-N
Standard InCHI:	InChI=1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1
Canonical SMILES:	COC1=C[C@@H]2[C@@H]3Cc4c([C@@]2(CC1=O)CCN3C)c(O)c(cc4)OC
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	TM-MC*
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	TM-MC*
NPO14677	Brachylaena neriifolia	Species	Asteraceae	Eukaryota	UNPD*
NPO15557	Menispermi rhizoma	NA	NA	NA	TCMSP*
NPO20961	Hugonia oreogena	Species	Linaceae	Eukaryota	UNPD*
NPO21740	Ajuga salicifolia	Species	Lamiaceae	Eukaryota	UNPD*
NPO22390	Virola theiodora	Species	Myristicaceae	Eukaryota	UNPD*
NPO22514	Cetraria cucullata	Species	Parmeliaceae	Eukaryota	UNPD*
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	HerDing*
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	TCMID*

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Biological Activity

Activity Type	# Activity
IC50	9
Others	8

Activity Type	# Activity
Cell Line	8
Individual Protein	5
Organism	3
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	-3	%	21530276
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	0.1	%	21530276
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	12.8	%	21530276
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000	nM	21530276
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	200000	nM	22325804
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	>	50000	nM	20097066
NPT2	Others	Unspecified		Ratio	=	4.41		22892114
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	152000	nM	11141105
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	4.63	%	23062825
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	5.14	%	23062825

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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 NPC298339 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	214
0.1-0.2	1074
0.2-0.3	2578
0.3-0.4	6518
0.4-0.5	6265
0.5-0.6	5883
0.6-0.7	7657
0.7-0.8	648
0.8-0.85	34
0.85-0.9	14
0.9-0.95	4
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7486	Intermediate Similarity	NPC133011
0.7486	Intermediate Similarity	NPC37272
0.7487	Intermediate Similarity	NPC94499
0.75	Intermediate Similarity	NPC476144
0.75	Intermediate Similarity	NPC225351

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 NPC298339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	695
0.2-0.3	1002
0.3-0.4	1933
0.4-0.5	2720
0.5-0.6	1720
0.6-0.7	779
0.7-0.8	100
0.8-0.85	19
0.85-0.9	12
0.9-0.95	2
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6774	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4110	Phase 3
0.6793	Remote Similarity	NPD2977	Approved
0.6793	Remote Similarity	NPD2978	Approved

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Structure

CID298339 OpenBabel06191716102D 24 27 0 0 1 0 0 0 0 0999 V2000 -2.1543 1.4997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3237 -1.3848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7980 -3.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7232 1.3857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5233 0.9241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4620 0.7995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4622 1.7232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1236 0.4616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7991 -1.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8001 -0.4613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9234 0.9237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7996 -0.4622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7998 0.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8006 -1.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5235 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0010 -1.8472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9236 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7236 -0.4617 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 -1.2620 1.2610 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6007 -1.8463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7239 -1.3853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3234 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0016 -2.7707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 15 1 0 0 0 0 6 7 1 0 0 0 0 7 20 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 16 2 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 12 13 1 0 0 0 0 12 19 1 1 0 0 0 13 8 1 1 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 21 2 0 0 0 0 15 18 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 22 1 0 0 0 0 19 6 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	5459308
ChEMBL	CHEMBL248095
ZINC

Physicochemical Properties

Molecular Weight:	329.16
ALogP:	-0.7813
MLogP:	3
XLogP:	1.294
# Rotatable Bonds:	6
Polar Surface Area:	59
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	24

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