NPASS Natural Product

Natural Product: NPC224609

Natural Product ID:	NPC224609
Common Name:	Epothilone C5
IUPAC Name:	(4S,7R,8R,9E,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione
Synonyms:	Epothilone C5
Molecular Formula:	C26H37NO5S
Standard InCHIKey:	MVIPGYRWGVEDHK-DQUVJOKZSA-N
Standard InCHI:	InChI=1S/C26H37NO5S/c1-16-11-9-7-8-10-12-21(17(2)13-20-15-33-19(4)27-20)32-23(29)14-22(28)26(5,6)25(31)18(3)24(16)30/h8,10-11,13,15,18,21-22,24,28,30H,7,9,12,14H2,1-6H3/b10-8-,16-11+,17-13+/t18-,21+,22+,24+/m1/s1
Canonical SMILES:	O=C1O[C@@H](C/C=CCC/C=C(/[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	Isolation Part	Collection Location	Collection Time	Reference
NPO32627	sorangium cellulosum, strains so ce90/b2	Species	Polyangiaceae	Bacteria				PMID[11473410]

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	=	1.5	ug/ml	12617583

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 NPC224609 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	113
0.1-0.2	636
0.2-0.3	2504
0.3-0.4	16407
0.4-0.5	10924
0.5-0.6	230
0.6-0.7	30
0.7-0.8	8
0.8-0.85	2
0.85-0.9	1
0.9-0.95	6
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC268063
0.993	High Similarity	NPC252616
0.993	High Similarity	NPC32583
0.993	High Similarity	NPC109498
0.993	High Similarity	NPC474090
0.993	High Similarity	NPC154873
0.993	High Similarity	NPC61667
0.993	High Similarity	NPC45576
0.993	High Similarity	NPC163147
0.9859	High Similarity	NPC474067
0.9859	High Similarity	NPC475737
0.9859	High Similarity	NPC185665
0.9859	High Similarity	NPC474094
0.9793	High Similarity	NPC127775
0.9789	High Similarity	NPC474079
0.9789	High Similarity	NPC21449
0.9789	High Similarity	NPC157194
0.9789	High Similarity	NPC474102
0.9789	High Similarity	NPC474080
0.9789	High Similarity	NPC475683
0.9718	High Similarity	NPC474103
0.9718	High Similarity	NPC82436
0.9718	High Similarity	NPC474064
0.9718	High Similarity	NPC474068
0.9524	High Similarity	NPC52587
0.9521	High Similarity	NPC202591
0.9521	High Similarity	NPC212214
0.9507	High Similarity	NPC474069
0.9456	High Similarity	NPC21126
0.9392	High Similarity	NPC474538
0.9384	High Similarity	NPC206724
0.9384	High Similarity	NPC474515
0.9329	High Similarity	NPC231110
0.9267	High Similarity	NPC312887
0.8873	High Similarity	NPC474070
0.838	Intermediate Similarity	NPC475604
0.8169	Intermediate Similarity	NPC475568
0.75	Intermediate Similarity	NPC315252
0.7468	Intermediate Similarity	NPC190329
0.7312	Intermediate Similarity	NPC319751
0.7233	Intermediate Similarity	NPC469801
0.7202	Intermediate Similarity	NPC211555
0.7178	Intermediate Similarity	NPC119481
0.7143	Intermediate Similarity	NPC186452
0.7117	Intermediate Similarity	NPC473398
0.6977	Remote Similarity	NPC12660
0.6936	Remote Similarity	NPC54983
0.6897	Remote Similarity	NPC97078
0.6897	Remote Similarity	NPC101980
0.6897	Remote Similarity	NPC470146
0.6508	Remote Similarity	NPC165538
0.6489	Remote Similarity	NPC122427
0.648	Remote Similarity	NPC164006
0.642	Remote Similarity	NPC56058
0.642	Remote Similarity	NPC522
0.6402	Remote Similarity	NPC329961
0.6328	Remote Similarity	NPC210424
0.6321	Remote Similarity	NPC469858
0.6313	Remote Similarity	NPC475554
0.6304	Remote Similarity	NPC132662
0.6271	Remote Similarity	NPC216720
0.6269	Remote Similarity	NPC475350
0.6269	Remote Similarity	NPC14877
0.6269	Remote Similarity	NPC145178
0.6264	Remote Similarity	NPC14101
0.6243	Remote Similarity	NPC24990
0.6176	Remote Similarity	NPC251036
0.6129	Remote Similarity	NPC161242
0.6108	Remote Similarity	NPC473704
0.6054	Remote Similarity	NPC134480
0.6047	Remote Similarity	NPC475390
0.6044	Remote Similarity	NPC473886
0.6043	Remote Similarity	NPC476080
0.6043	Remote Similarity	NPC475534
0.6033	Remote Similarity	NPC476103
0.5979	Remote Similarity	NPC263485
0.5979	Remote Similarity	NPC229160
0.5979	Remote Similarity	NPC25316
0.5939	Remote Similarity	NPC239660
0.5939	Remote Similarity	NPC106235
0.5926	Remote Similarity	NPC475330
0.5917	Remote Similarity	NPC475196
0.5895	Remote Similarity	NPC174652
0.5833	Remote Similarity	NPC161143
0.5747	Remote Similarity	NPC478251
0.5747	Remote Similarity	NPC478252
0.569	Remote Similarity	NPC193753
0.569	Remote Similarity	NPC160222
0.5671	Remote Similarity	NPC267605
0.5654	Remote Similarity	NPC475455
0.5638	Remote Similarity	NPC30527
0.5631	Remote Similarity	NPC75498
0.5612	Remote Similarity	NPC96016

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC224609 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	126
0.1-0.2	389
0.2-0.3	1276
0.3-0.4	4985
0.4-0.5	2237
0.5-0.6	137
0.6-0.7	5
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9859	High Similarity	NPD6907	Phase 2
0.9456	High Similarity	NPD6910	Phase 3
0.9195	High Similarity	NPD6911	Discontinued
0.8968	High Similarity	NPD6916	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD6915	Approved
0.7165	Intermediate Similarity	NPD7496	Phase 2
0.6448	Remote Similarity	NPD2957	Phase 2
0.6416	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5634	Approved
0.622	Remote Similarity	NPD1083	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6870	Phase 1
0.5979	Remote Similarity	NPD6348	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD6349	Phase 1
0.5789	Remote Similarity	NPD6641	Approved
0.5789	Remote Similarity	NPD6642	Approved
0.567	Remote Similarity	NPD7977	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD4949	Discontinued
0.5625	Remote Similarity	NPD8071	Approved
0.5613	Remote Similarity	NPD6413	Approved

Structure

NPC224609 OpenBabel07101718202D 33 34 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 -8.1495 -2.0432 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 -0.3214 0.9469 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 -1.0000 -5.0273 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 -1.9239 -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 -2.6310 -3.9375 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 -1.9239 -0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0532 -3.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0137 -3.0137 0.0000 C 0 0 0 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 -7.2414 -2.4618 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 -3.0137 -3.0137 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 -6.3689 -1.9732 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 -3.0137 -2.0137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0463 -3.4426 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 4 19 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 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 16 2 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 20 2 0 0 0 0 15 33 1 0 0 0 0 16 24 1 0 0 0 0 18 3 1 6 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 27 2 0 0 0 0 19 33 1 0 0 0 0 20 27 1 0 0 0 0 21 17 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 32 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	10885254
ChEMBL	CHEMBL460039
ZINC

Physicochemical Properties

Molecular Weight:	475.24
ALogP:	3.522
MLogP:	3.55
XLogP:	2.97
# Rotatable Bonds:	10
Polar Surface Area:	124.96
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	33

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