NPASS Natural Product

Natural Product: NPC295643

Natural Product ID:	NPC295643
Common Name:	Methyl Glycyrrhetinate
IUPAC Name:	methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
Synonyms:
Molecular Formula:	C31H48O4
Standard InCHIKey:	RMIVRCBSQPCSCQ-BDANYOJNSA-N
Standard InCHI:	InChI=1S/C31H48O4/c1-26(2)22-9-12-31(7)24(29(22,5)11-10-23(26)33)21(32)17-19-20-18-28(4,25(34)35-8)14-13-27(20,3)15-16-30(19,31)6/h17,20,22-24,33H,9-16,18H2,1-8H3/t20-,22-,23-,24+,27+,28-,29-,30+,31+/m0/s1
Canonical SMILES:	COC(=O)[C@@]1(C)CC[C@]2([C@@H](C1)C1=CC(=O)[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)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	Reference
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	UNPD*
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	UNPD*
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
EC50	5
IC50	48
Ki	1
Others	2

Activity Type	# Activity
Cell Line	35
Individual Protein	3
Organism	3
Others	15

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1215	Cell Line	8505C	Homo sapiens	IC50	=	26070	nM	20932766
NPT1215	Cell Line	8505C	Homo sapiens	IC50	=	26070	nM	20884085
NPT1215	Cell Line	8505C	Homo sapiens	IC50	=	26070	nM	24361520
NPT1215	Cell Line	8505C	Homo sapiens	EC50	>	30000	nM	26177446
NPT1216	Cell Line	FaDu	Homo sapiens	IC50	=	23410	nM	20932766
NPT1216	Cell Line	FaDu	Homo sapiens	IC50	=	23410	nM	20884085
NPT1218	Individual Protein	Carbonic anhydrase II	Bos taurus	Ki	>	10000	nM	25147151
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	27540	nM	20932766
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	27540	nM	20884085
NPT139	Cell Line	HT-29	Homo sapiens	EC50	>	30000	nM	26177446

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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 NPC295643 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	135
0.1-0.2	716
0.2-0.3	2763
0.3-0.4	6207
0.4-0.5	9634
0.5-0.6	4541
0.6-0.7	3539
0.7-0.8	2707
0.8-0.85	341
0.85-0.9	155
0.9-0.95	135
0.95-1	16

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Similarity Score	Similarity Level	Natural Product ID
0.8817	High Similarity	NPC476327
0.8817	High Similarity	NPC132824
0.883	High Similarity	NPC260149
0.883	High Similarity	NPC188833
0.883	High Similarity	NPC164349

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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 NPC295643 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1190
0.2-0.3	3460
0.3-0.4	2798
0.4-0.5	989
0.5-0.6	249
0.6-0.7	157
0.7-0.8	144
0.8-0.85	26
0.85-0.9	0
0.9-0.95	3
0.95-1	2

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6854	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4137	Phase 3
0.6854	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5779	Approved
0.6863	Remote Similarity	NPD5778	Approved

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Structure

CID295643 OpenBabel06191716102D 35 39 0 0 1 0 0 0 0 0999 V2000 -1.8437 -2.1519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4339 -1.8356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0206 4.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5831 5.1012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 1.9500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3775 -0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0456 4.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5331 3.4125 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6887 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 0.4875 0.0000 C 0 0 1 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 -1.6887 1.9500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -1.4625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 5.1012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0706 4.2569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 6 30 1 0 0 0 0 8 35 1 0 0 0 0 9 12 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 29 1 0 0 0 0 12 31 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 30 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 27 1 6 0 0 0 21 24 1 0 0 0 0 21 32 2 0 0 0 0 22 26 1 0 0 0 0 22 29 1 1 0 0 0 23 26 1 0 0 0 0 23 33 1 1 0 0 0 24 29 1 1 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 25 34 2 0 0 0 0 25 35 1 0 0 0 0 27 3 1 1 0 0 0 28 4 1 6 0 0 0 29 5 1 1 0 0 0 30 31 1 1 0 0 0 31 7 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	102135
ChEMBL	CHEMBL1271483
ZINC

Physicochemical Properties

Molecular Weight:	484.36
ALogP:	1.9341
MLogP:	4.43
XLogP:	7.066
# Rotatable Bonds:	11
Polar Surface Area:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	35

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