NPASS Natural Product

Natural Product: NPC233455

Natural Product ID:	NPC233455
Common Name:	Enoxolone
IUPAC Name:	(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-carboxylic acid
Synonyms:	Enoxolone; Glycyrrhetic Acid; NSC-35347; NSC-35350; Rhetinic Acid; Uralenic Acid
Molecular Formula:	C30H46O4
Standard InCHIKey:	MPDGHEJMBKOTSU-YKLVYJNSSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1
Canonical SMILES:	O=C1C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C([C@@H]1CC2)(C)C)O)C)C)C(=O)O
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
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota		UNPD*
NPO15711	Radix glycyrrhizae preparata	Species	Lymnaeidae	Eukaryota		TCMID*
NPO15835	Glycyrrhiza	Species	Fabaceae	Eukaryota		TCMSP*
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota		TM-MC*
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	blood	PMID[18850581]
NPO24837	Radix glycyrrhizae uralensis	Species	Lymnaeidae	Eukaryota		TCMID*
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	PMID[23541646]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota		TM-MC*
NPO29703	Abri herba	NA	NA	NA		TCMSP*
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota		HerDing*

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Biological Activity

Activity Type	# Activity
EC50	6
ED50	7
GI50	12
IC50	89
Kd	1
Ki	4
Others	68
Potency	75

Activity Type	# Activity
Cell Line	78
Individual Protein	80
Organism	14
Others	89
Protein-Protein Interaction	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		24813.5	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		7307.8	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency		10840.2	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT1125	Cell Line	T98G	Homo sapiens	GI50	=	85000	nM	21888390
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1300	nM	19278854
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	187880	nM	23373965
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	5.12	%	23373965
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	102	%	6677713
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	58	%	6677713

Showing 1 to 10 of 237 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 NPC233455 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	131
0.1-0.2	718
0.2-0.3	2849
0.3-0.4	6699
0.4-0.5	9286
0.5-0.6	4561
0.6-0.7	3490
0.7-0.8	2496
0.8-0.85	347
0.85-0.9	157
0.9-0.95	111
0.95-1	44

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Similarity Score	Similarity Level	Natural Product ID
0.8842	High Similarity	NPC476890
0.8864	High Similarity	NPC162107
0.8864	High Similarity	NPC46912
0.8876	High Similarity	NPC69627
0.8876	High Similarity	NPC477973

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 NPC233455 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1216
0.2-0.3	3518
0.3-0.4	2753
0.4-0.5	963
0.5-0.6	236
0.6-0.7	156
0.7-0.8	154
0.8-0.85	17
0.85-0.9	3
0.9-0.95	1
0.95-1	2

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6809	Remote Similarity	NPD4195	Approved
0.681	Remote Similarity	NPD6054	Approved
0.681	Remote Similarity	NPD6059	Approved
0.6814	Remote Similarity	NPD5167	Approved
0.6832	Remote Similarity	NPD5694	Approved

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Structure

CID233455 OpenBabel06191716032D 34 38 0 0 1 0 0 0 0 0999 V2000 1.8425 2.1505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4316 1.8344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0186 -4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -1.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3753 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0443 -4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5315 -3.4103 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 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 1.6876 -1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -5.0979 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0699 -4.2541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 6 29 1 0 0 0 0 8 11 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 28 1 0 0 0 0 11 30 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 29 1 0 0 0 0 19 26 1 6 0 0 0 20 23 1 0 0 0 0 20 31 2 0 0 0 0 21 25 1 0 0 0 0 21 28 1 1 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 6 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	10114
ChEMBL	CHEMBL230006
ZINC

Physicochemical Properties

Molecular Weight:	470.34
ALogP:	1.6831
MLogP:	4.32
XLogP:	6.745
# Rotatable Bonds:	10
Polar Surface Area:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	34

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