NPASS Natural Product

Natural Product: NPC112454

Natural Product ID:	NPC112454
Common Name:	Celastrol
IUPAC Name:	(2R,4aS,6aR,6aS,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid
Synonyms:	Celastrol
Molecular Formula:	C29H38O4
Standard InCHIKey:	KQJSQWZMSAGSHN-JJWQIEBTSA-N
Standard InCHI:	InChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
Canonical SMILES:	O=C1C=C2C(=CC=C3[C@@]2(C)CC[C@@]2([C@]3(C)CC[C@@]3([C@H]2C[C@@](C)(CC3)C(=O)O)C)C)C(=C1O)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
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota		TM-MC*
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Root	DOI[10.1186/1471-2202-6-1]
NPO13668	Taraxacum platycarpum	Species	Asteraceae	Eukaryota		TM-MC*
NPO14544	Maytenus chuchuhuasca	Species	Celastraceae	Eukaryota		PMID[18164197]
NPO15815	Macrophomina phaseolina	Species	Botryosphaeriaceae	Eukaryota		UNPD*
NPO1596	Taraxacum borealisinense	Species	Asteraceae	Eukaryota		TM-MC*
NPO17746	Tripterygii radix	NA	NA	NA		TCMSP*
NPO23327	Taraxacum coreanum	Species	Asteraceae	Eukaryota		TM-MC*
NPO25915	Sinularia brassica	Species	Alcyoniidae	Eukaryota		UNPD*

Showing 1 to 10 of 27 entries

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Biological Activity

Activity Type	# Activity
EC50	4
ED50	24
GI50	60
IC50	44
Ki	1
Others	20

Activity Type	# Activity
Cell Line	112
Individual Protein	11
Organism	10
Others	20

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	1.3	ug/ml	8158155
NPT111	Cell Line	K562	Homo sapiens	GI50		20.09	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		12.39	nM	PubChem BioAssay data set
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	230	nM	11809076
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	270	nM	11809076
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1000	nM	21978676
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1000	nM	22024033
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000	nM	22705020
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1000	nM	23127886
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	800	nM	23234407

Showing 1 to 10 of 149 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 NPC112454 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	134
0.1-0.2	752
0.2-0.3	2809
0.3-0.4	7840
0.4-0.5	9533
0.5-0.6	5272
0.6-0.7	3418
0.7-0.8	991
0.8-0.85	102
0.85-0.9	28
0.9-0.95	7
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.7849	Intermediate Similarity	NPC64872
0.7849	Intermediate Similarity	NPC118011
0.7849	Intermediate Similarity	NPC470588
0.7849	Intermediate Similarity	NPC270768
0.7849	Intermediate Similarity	NPC25906

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 NPC112454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1163
0.2-0.3	3385
0.3-0.4	2903
0.4-0.5	1019
0.5-0.6	278
0.6-0.7	184
0.7-0.8	78
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6283	Remote Similarity	NPD5247	Approved
0.6283	Remote Similarity	NPD5251	Approved
0.6283	Remote Similarity	NPD5250	Approved
0.6283	Remote Similarity	NPD5169	Approved
0.6283	Remote Similarity	NPD5248	Approved

Showing 1 to 5 of 200 entries

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Structure

CID112454 OpenBabel06191715462D 33 37 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 0.5000 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 1.7321 1.0000 0.0000 C 0 0 0 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 3.4641 0.0000 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 -1.7321 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 0 0 0 0 0 0 0 0 0 0 -0.0000 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 0.8660 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 18 2 0 0 0 0 8 21 2 0 0 0 0 9 10 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 23 2 0 0 0 0 18 19 1 0 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 20 30 2 0 0 0 0 21 27 1 0 0 0 0 21 28 1 0 0 0 0 22 25 1 6 0 0 0 22 29 1 0 0 0 0 23 31 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 2 1 1 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	122724
ChEMBL	CHEMBL301982
ZINC

Physicochemical Properties

Molecular Weight:	450.28
ALogP:	2.4831
MLogP:	4.21
XLogP:	7.98
# Rotatable Bonds:	9
Polar Surface Area:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	33

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