NPASS Natural Product

Natural Product: NPC118162

Natural Product ID:	NPC118162
Common Name:	Gomisin C
IUPAC Name:
Synonyms:	Gomisin C
Molecular Formula:	C30H32O9
Standard InCHIKey:	UFCGDBKFOKKVAC-DSASHONVSA-N
Standard InCHI:	InChI=1S/C30H32O9/c1-16-12-18-13-21-25(38-15-37-21)26(35-5)22(18)23-19(14-20(33-3)24(34-4)27(23)36-6)28(30(16,2)32)39-29(31)17-10-8-7-9-11-17/h7-11,13-14,16,28,32H,12,15H2,1-6H3/t16-,28-,30-/m0/s1
Canonical SMILES:	COc1cc2c(c(c1OC)OC)c1c(cc3c(c1OC)OCO3)C[C@@H]([C@]([C@H]2OC(=O)c1ccccc1)(C)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	Reference
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota		PMID[12350139]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	PMID[23265871]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota		TM-MC*
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota		TM-MC*
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	PMID[23265871]

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Biological Activity

Activity Type	# Activity
GI50	7
IC50	7
Ki	1
Others	6

Activity Type	# Activity
Cell Line	11
Individual Protein	1
Others	9

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1086	Cell Line	SK-HEP1	Homo sapiens	IC50	=	70400	nM	18063366
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	399	nM	16248836
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000	nM	18063366
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	100000	nM	18063366
NPT2	Others	Unspecified		Activity	=	19.7	%	12350139
NPT2	Others	Unspecified		Activity	=	60.2	%	12350139
NPT2	Others	Unspecified		Activity	=	87.4	%	12350139
NPT2	Others	Unspecified		Activity	=	100	%	12350139
NPT2	Others	Unspecified		Inhibition	=	-139	%	23265871
NPT2	Others	Unspecified		GI50	>	100000	nM	10.1039/C6MD00097E

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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 NPC118162 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	282
0.1-0.2	1098
0.2-0.3	2121
0.3-0.4	4563
0.4-0.5	7337
0.5-0.6	3991
0.6-0.7	3723
0.7-0.8	6788
0.8-0.85	815
0.85-0.9	130
0.9-0.95	33
0.95-1	8

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Similarity Score	Similarity Level	Natural Product ID
0.8443	Intermediate Similarity	NPC209411
0.8443	Intermediate Similarity	NPC469889
0.8443	Intermediate Similarity	NPC239890
0.8448	Intermediate Similarity	NPC80956
0.8452	Intermediate Similarity	NPC116759

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 NPC118162 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	839
0.2-0.3	1546
0.3-0.4	2516
0.4-0.5	2094
0.5-0.6	1170
0.6-0.7	517
0.7-0.8	165
0.8-0.85	15
0.85-0.9	8
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6954	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6746	Phase 2
0.6964	Remote Similarity	NPD4308	Phase 3
0.6973	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD643	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

CID118162 OpenBabel06191715472D 39 43 0 0 1 0 0 0 0 0999 V2000 0.3100 -1.5585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9474 0.1247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6757 4.9414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0646 4.1138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9620 3.8222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4979 3.2863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2894 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5313 2.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1646 0.8892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6485 2.0526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2818 0.5235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6312 -0.6757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1345 -0.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1979 2.4588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4324 0.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6757 -0.6757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5237 1.1052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3069 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6757 1.6312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6757 3.2863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9620 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3069 0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6312 1.6312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6312 3.2863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9620 0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1345 1.4333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1090 2.4588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6409 0.7395 0.0000 C 0 0 0 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 -1.5162 -0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5817 -0.7581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1979 4.1138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1090 4.1138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1345 3.3444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0201 2.4588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8708 -0.2953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8708 1.2508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8828 1.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 5 35 1 0 0 0 0 6 36 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 37 1 0 0 0 0 15 38 1 0 0 0 0 16 30 1 6 0 0 0 17 29 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 28 1 0 0 0 0 20 24 2 0 0 0 0 20 33 1 0 0 0 0 21 25 2 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 26 2 0 0 0 0 23 27 2 0 0 0 0 24 27 1 0 0 0 0 24 34 1 0 0 0 0 25 26 1 0 0 0 0 25 38 1 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 28 30 1 1 0 0 0 28 39 1 0 0 0 0 29 31 2 0 0 0 0 29 39 1 0 0 0 0 30 2 1 1 0 0 0 30 32 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	151529
ChEMBL	CHEMBL404875
ZINC

Physicochemical Properties

Molecular Weight:	536.20
ALogP:	-0.5025
MLogP:	3.77
XLogP:	4.763
# Rotatable Bonds:	14
Polar Surface Area:	101.91
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	39

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