NPASS Natural Product

Natural Product: NPC212214

Natural Product ID:	NPC212214
Common Name:	Epothilone A
IUPAC Name:	(1R,5S,6S,7R,10S,14S,16S)-6,10-dihydroxy-5,7,9,9-tetramethyl-14-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-13,17-dioxabicyclo[14.1.0]heptadecane-8,12-dione
Synonyms:
Molecular Formula:	C26H39NO6S
Standard InCHIKey:	HESCAJZNRMSMJG-KKQRBIROSA-N
Standard InCHI:	InChI=1S/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3/b15-10+/t14-,16+,19+,20-,21-,22-,24-/m0/s1
Canonical SMILES:	O=C1O[C@@H](C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](C1)O)(C)C)C)O)C)/C(=C/c1csc(n1)C)/C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO32627	sorangium cellulosum, strains so ce90/b2	Species	Polyangiaceae	Bacteria	PMID[11473410]
NPO8615	Streptomyces cellulosum	Species	Streptomycetaceae	Bacteria	StreptomeDB*
NPO10330.13	Streptomyces coelicolor ch999	Subspecies	Streptomycetaceae	Bacteria	StreptomeDB*

Biological Activity

Activity Type	# Activity
EC50	2
GI50	58
IC50	26
Kd	1
MIC	2
Others	11

Activity Type	# Activity
Cell Line	80
Organism	1
Others	17
Protein Family	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	IC50	=	2.15	nM	11133086
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.91	nM	11133086
NPT2688	Organism	Sus scrofa	Sus scrofa	EC50	=	1120	nM	11133086
NPT309	Cell Line	1A9	Homo sapiens	IC50	=	2.2	nM	16134928
NPT310	Cell Line	1A9/ptx-10	Homo sapiens	IC50	=	20	nM	16134928
NPT5191	Cell Line	1A9/ptx-22	Homo sapiens	IC50	=	5.9	nM	16134928
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.9	nM	18271516
NPT2	Others	Unspecified		IC50	=	6.4	nM	18271516
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	2.8	nM	18271516
NPT2	Others	Unspecified		EC50	=	4600	nM	18271516
NPT1460	Cell Line	L929	Mus musculus	IC50	=	0.004	ug/ml	11473410
NPT2	Others	Unspecified		Activity	=	89	%	19433359
NPT2	Others	Unspecified		Activity	=	83	%	19433359
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2.2	nM	19433359
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.6	nM	19433359
NPT3014	Protein Family	Tubulin	Sus scrofa	Inhibition	=	99.8	%	19804980
NPT3014	Protein Family	Tubulin	Sus scrofa	Inhibition	=	92.2	%	19804980
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2.6	nM	19804980
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.5	nM	19804980
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	1.3	nM	19804980
NPT2	Others	Unspecified		IC50	=	70	nM	19804980
NPT2	Others	Unspecified		MIC	=	5	nM	19804980
NPT306	Cell Line	PC-3	Homo sapiens	FC	=	0.291		16680159
NPT2	Others	Unspecified		Kd	=	28	nM	17206139
NPT2	Others	Unspecified		Activity	=	95	%	17206139
NPT2	Others	Unspecified		Activity	=	96	%	17206139
NPT2	Others	Unspecified		Activity	=	49	%	17206139
NPT2	Others	Unspecified		Activity	=	46	%	17206139
NPT367	Cell Line	MDA-N	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT368	Cell Line	SN12C	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT369	Cell Line	ACHN	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT371	Cell Line	UO-31	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT372	Cell Line	HOP-92	Homo sapiens	GI50		3.899	nM	PubChem BioAssay data set
NPT374	Cell Line	SF-539	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT90	Cell Line	DU-145	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT376	Cell Line	A498	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT111	Cell Line	K562	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT379	Cell Line	HOP-62	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50		0.1132	nM	PubChem BioAssay data set
NPT380	Cell Line	U-251	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT383	Cell Line	SNB-19	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT385	Cell Line	SR	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT384	Cell Line	TK-10	Homo sapiens	GI50		16.71	nM	PubChem BioAssay data set
NPT323	Cell Line	SW-620	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT386	Cell Line	KM12	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT387	Cell Line	M14	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50		123.88	nM	PubChem BioAssay data set
NPT457	Cell Line	BT-549	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT81	Cell Line	A549	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT392	Cell Line	SNB-75	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT393	Cell Line	HCT-116	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT395	Cell Line	SF-268	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT394	Cell Line	EKVX	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT83	Cell Line	MCF7	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT306	Cell Line	PC-3	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT396	Cell Line	T47D	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT398	Cell Line	UACC-62	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT399	Cell Line	SF-295	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT401	Cell Line	786-0	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT403	Cell Line	UACC-257	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT407	Cell Line	COLO 205	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT406	Cell Line	RXF 393	Homo sapiens	GI50		0.1	nM	PubChem BioAssay data set
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.9	nM	25084144
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.8	nM	25084144
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5000	nM	25084144
NPT1460	Cell Line	L929	Mus musculus	IC50	=	7.7	nM	25397992
NPT2	Others	Unspecified		IC50	=	2.4	nM	25397992
NPT2	Others	Unspecified		IC50	=	9.6	nM	25397992
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.2	nM	25397992
NPT2	Others	Unspecified		IC50	=	1.3	nM	25397992

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 NPC212214 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	116
0.1-0.2	652
0.2-0.3	2633
0.3-0.4	17484
0.4-0.5	9748
0.5-0.6	188
0.6-0.7	25
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	8
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC21126
0.9862	High Similarity	NPC52587
0.9862	High Similarity	NPC474538
0.9861	High Similarity	NPC202591
0.986	High Similarity	NPC206724
0.986	High Similarity	NPC474515
0.9795	High Similarity	NPC231110
0.9728	High Similarity	NPC312887
0.9653	High Similarity	NPC185665
0.9653	High Similarity	NPC475737
0.9653	High Similarity	NPC474094
0.9586	High Similarity	NPC163147
0.9586	High Similarity	NPC45576
0.9586	High Similarity	NPC61667
0.9586	High Similarity	NPC474090
0.9586	High Similarity	NPC154873
0.9586	High Similarity	NPC32583
0.9586	High Similarity	NPC109498
0.9586	High Similarity	NPC252616
0.9521	High Similarity	NPC268063
0.9521	High Similarity	NPC224609
0.9517	High Similarity	NPC474067
0.9514	High Similarity	NPC474068
0.9514	High Similarity	NPC474103
0.9514	High Similarity	NPC82436
0.9514	High Similarity	NPC474064
0.9448	High Similarity	NPC157194
0.9448	High Similarity	NPC21449
0.9448	High Similarity	NPC474080
0.9448	High Similarity	NPC475683
0.9448	High Similarity	NPC474102
0.9448	High Similarity	NPC474079
0.9329	High Similarity	NPC127775
0.9172	High Similarity	NPC474069
0.8425	Intermediate Similarity	NPC474070
0.7945	Intermediate Similarity	NPC475604
0.774	Intermediate Similarity	NPC475568
0.7246	Intermediate Similarity	NPC315252
0.7235	Intermediate Similarity	NPC12660
0.7205	Intermediate Similarity	NPC190329
0.7193	Intermediate Similarity	NPC54983
0.7081	Intermediate Similarity	NPC469801
0.7	Intermediate Similarity	NPC186452
0.6959	Remote Similarity	NPC211555
0.6951	Remote Similarity	NPC319751
0.6826	Remote Similarity	NPC119481
0.6766	Remote Similarity	NPC473398
0.6667	Remote Similarity	NPC470146
0.6667	Remote Similarity	NPC97078
0.6667	Remote Similarity	NPC101980
0.6477	Remote Similarity	NPC522
0.6477	Remote Similarity	NPC56058
0.6354	Remote Similarity	NPC164006
0.6302	Remote Similarity	NPC165538
0.6292	Remote Similarity	NPC210424
0.6283	Remote Similarity	NPC122427
0.6278	Remote Similarity	NPC475554
0.6236	Remote Similarity	NPC216720
0.6215	Remote Similarity	NPC469858
0.6198	Remote Similarity	NPC329961
0.6183	Remote Similarity	NPC132662
0.6162	Remote Similarity	NPC473704
0.6108	Remote Similarity	NPC134480
0.6045	Remote Similarity	NPC14101
0.6033	Remote Similarity	NPC24990
0.6	Remote Similarity	NPC475350
0.6	Remote Similarity	NPC145178
0.6	Remote Similarity	NPC14877
0.5926	Remote Similarity	NPC161242
0.5913	Remote Similarity	NPC251036
0.5842	Remote Similarity	NPC475534
0.5842	Remote Similarity	NPC476080
0.5838	Remote Similarity	NPC473886
0.5829	Remote Similarity	NPC476103
0.5829	Remote Similarity	NPC239660
0.5829	Remote Similarity	NPC475390
0.5829	Remote Similarity	NPC106235
0.5781	Remote Similarity	NPC263485
0.5781	Remote Similarity	NPC229160
0.5781	Remote Similarity	NPC25316
0.5747	Remote Similarity	NPC475196
0.5729	Remote Similarity	NPC475330
0.5722	Remote Similarity	NPC161143
0.5699	Remote Similarity	NPC174652
0.5625	Remote Similarity	NPC478252
0.5625	Remote Similarity	NPC478251
0.5608	Remote Similarity	NPC30527

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC212214 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	125
0.1-0.2	393
0.2-0.3	1432
0.3-0.4	5308
0.4-0.5	1792
0.5-0.6	101
0.6-0.7	4
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9931	High Similarity	NPD6910	Phase 3
0.9658	High Similarity	NPD6911	Discontinued
0.9653	High Similarity	NPD6907	Phase 2
0.9408	High Similarity	NPD6916	Clinical (unspecified phase)
0.8693	High Similarity	NPD6915	Approved
0.7306	Intermediate Similarity	NPD7496	Phase 2
0.6379	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD2957	Phase 2
0.6307	Remote Similarity	NPD5634	Approved
0.6031	Remote Similarity	NPD6348	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD1083	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6349	Phase 1
0.5882	Remote Similarity	NPD6870	Phase 1
0.5829	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD7977	Clinical (unspecified phase)

Structure

CID212214 OpenBabel06191716002D 34 36 0 0 1 0 0 0 0 0999 V2000 2.9945 -3.2088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3159 -4.1557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4625 -0.5342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7251 -4.1769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3214 0.9469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6593 0.7518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9239 -4.6447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6310 -3.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6538 -2.4569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6310 -3.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9239 -0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3689 -1.9732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0137 -3.0137 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9945 -3.2088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6310 -1.0898 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0463 -3.4426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6346 -2.6520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -5.0273 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0137 -3.0137 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9239 -4.6447 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6310 -1.0898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0137 -2.0137 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9239 -0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0532 -3.5602 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1951 0.9808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4625 -0.5342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9945 -1.8186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4794 0.4488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7934 -5.6361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0137 -2.0137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2414 -2.4618 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 15 1 0 0 0 0 4 17 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 14 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 12 23 1 0 0 0 0 13 18 2 0 0 0 0 13 34 1 0 0 0 0 14 1 1 1 0 0 0 14 24 1 0 0 0 0 16 3 1 6 0 0 0 16 24 1 0 0 0 0 16 25 1 0 0 0 0 17 27 2 0 0 0 0 17 34 1 0 0 0 0 18 27 1 0 0 0 0 19 9 1 1 0 0 0 19 21 1 0 0 0 0 19 32 1 0 0 0 0 20 15 1 1 0 0 0 20 33 1 0 0 0 0 21 11 1 1 0 0 0 21 32 1 0 0 0 0 22 26 1 0 0 0 0 22 28 1 6 0 0 0 23 29 2 0 0 0 0 23 33 1 0 0 0 0 24 30 1 1 0 0 0 25 26 1 0 0 0 0 25 31 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	448799
ChEMBL	CHEMBL329993
ZINC

Physicochemical Properties

Molecular Weight:	493.25
ALogP:	0.6433
MLogP:	3.44
XLogP:	2.507
# Rotatable Bonds:	10
Polar Surface Area:	137.49
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	34

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General Info & Identifiers & Properties
Structure MOL file
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Similar NPs/Drugs