NPASS Natural Product

Natural Product: NPC154873

Natural Product ID:	NPC154873
Common Name:	Epothilone D5
IUPAC Name:	(4S,7R,8R,9E,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-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 D5
Molecular Formula:	C27H39NO5S
Standard InCHIKey:	OQUHUZWYEYDRMH-JGMJILQLSA-N
Standard InCHI:	InChI=1S/C27H39NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h10-11,13,15,19,22-23,25,29,31H,8-9,12,14H2,1-7H3/b16-11-,17-10+,18-13+/t19-,22+,23+,25+/m1/s1
Canonical SMILES:	O=C1O[C@@H](C/C=C(/C)CC/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	=	0.2	ug/ml	10785421

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 NPC154873 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	112
0.1-0.2	635
0.2-0.3	2548
0.3-0.4	16860
0.4-0.5	10479
0.5-0.6	185
0.6-0.7	24
0.7-0.8	9
0.8-0.85	2
0.85-0.9	1
0.9-0.95	7
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC268063
0.993	High Similarity	NPC224609
0.9929	High Similarity	NPC475737
0.9929	High Similarity	NPC474094
0.9929	High Similarity	NPC185665
0.9859	High Similarity	NPC163147
0.9859	High Similarity	NPC61667
0.9859	High Similarity	NPC32583
0.9859	High Similarity	NPC45576
0.9859	High Similarity	NPC474090
0.9859	High Similarity	NPC252616
0.9859	High Similarity	NPC109498
0.9789	High Similarity	NPC474067
0.9787	High Similarity	NPC82436
0.9787	High Similarity	NPC474064
0.9787	High Similarity	NPC474068
0.9787	High Similarity	NPC474103
0.9724	High Similarity	NPC127775
0.9718	High Similarity	NPC475683
0.9718	High Similarity	NPC474079
0.9718	High Similarity	NPC474102
0.9718	High Similarity	NPC157194
0.9718	High Similarity	NPC474080
0.9718	High Similarity	NPC21449
0.9589	High Similarity	NPC52587
0.9586	High Similarity	NPC212214
0.9521	High Similarity	NPC21126
0.9456	High Similarity	NPC474538
0.9452	High Similarity	NPC202591
0.9448	High Similarity	NPC474515
0.9448	High Similarity	NPC206724
0.9437	High Similarity	NPC474069
0.9392	High Similarity	NPC231110
0.9329	High Similarity	NPC312887
0.8803	High Similarity	NPC474070
0.831	Intermediate Similarity	NPC475604
0.8099	Intermediate Similarity	NPC475568
0.7439	Intermediate Similarity	NPC315252
0.7405	Intermediate Similarity	NPC190329
0.725	Intermediate Similarity	NPC319751
0.7186	Intermediate Similarity	NPC186452
0.717	Intermediate Similarity	NPC469801
0.7143	Intermediate Similarity	NPC211555
0.7117	Intermediate Similarity	NPC119481
0.7055	Intermediate Similarity	NPC473398
0.7018	Intermediate Similarity	NPC12660
0.6977	Remote Similarity	NPC54983
0.6839	Remote Similarity	NPC97078
0.6839	Remote Similarity	NPC470146
0.6839	Remote Similarity	NPC101980
0.6517	Remote Similarity	NPC164006
0.6457	Remote Similarity	NPC56058
0.6457	Remote Similarity	NPC522
0.6455	Remote Similarity	NPC165538
0.6436	Remote Similarity	NPC122427
0.6364	Remote Similarity	NPC210424
0.6349	Remote Similarity	NPC329961
0.6348	Remote Similarity	NPC475554
0.6339	Remote Similarity	NPC132662
0.6307	Remote Similarity	NPC216720
0.6274	Remote Similarity	NPC469858
0.6219	Remote Similarity	NPC145178
0.6219	Remote Similarity	NPC475350
0.6219	Remote Similarity	NPC14877
0.6207	Remote Similarity	NPC14101
0.6188	Remote Similarity	NPC24990
0.6141	Remote Similarity	NPC473704
0.6127	Remote Similarity	NPC251036
0.6087	Remote Similarity	NPC134480
0.6075	Remote Similarity	NPC161242
0.5989	Remote Similarity	NPC475534
0.5989	Remote Similarity	NPC473886
0.5989	Remote Similarity	NPC476080
0.5988	Remote Similarity	NPC475390
0.5978	Remote Similarity	NPC476103
0.5926	Remote Similarity	NPC229160
0.5926	Remote Similarity	NPC25316
0.5926	Remote Similarity	NPC263485
0.5888	Remote Similarity	NPC239660
0.5888	Remote Similarity	NPC106235
0.5873	Remote Similarity	NPC475330
0.5872	Remote Similarity	NPC475196
0.5842	Remote Similarity	NPC174652
0.5781	Remote Similarity	NPC161143
0.5706	Remote Similarity	NPC267605
0.569	Remote Similarity	NPC478251
0.569	Remote Similarity	NPC478252
0.5632	Remote Similarity	NPC193753
0.5632	Remote Similarity	NPC160222
0.5602	Remote Similarity	NPC475455

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC154873 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	124
0.1-0.2	385
0.2-0.3	1354
0.3-0.4	5126
0.4-0.5	2044
0.5-0.6	117
0.6-0.7	5
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9929	High Similarity	NPD6907	Phase 2
0.9521	High Similarity	NPD6910	Phase 3
0.9257	High Similarity	NPD6911	Discontinued
0.9026	High Similarity	NPD6916	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD6915	Approved
0.7113	Intermediate Similarity	NPD7496	Phase 2
0.6484	Remote Similarity	NPD2957	Phase 2
0.6358	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5634	Approved
0.6258	Remote Similarity	NPD1083	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6870	Phase 1
0.5928	Remote Similarity	NPD6348	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD6349	Phase 1
0.5737	Remote Similarity	NPD6642	Approved
0.5737	Remote Similarity	NPD6641	Approved
0.5619	Remote Similarity	NPD7977	Clinical (unspecified phase)

Structure

NPC154873 OpenBabel07101719132D 34 35 0 0 1 0 0 0 0 0999 V2000 -1.1951 -6.0081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 0.9239 -4.6447 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 1.6310 -3.9375 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 -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 -1.0000 -5.0273 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 3 18 1 0 0 0 0 5 20 1 0 0 0 0 6 27 1 0 0 0 0 7 27 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 22 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 14 24 1 0 0 0 0 15 21 2 0 0 0 0 15 34 1 0 0 0 0 17 25 1 0 0 0 0 19 4 1 6 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 28 2 0 0 0 0 20 34 1 0 0 0 0 21 28 1 0 0 0 0 22 18 1 1 0 0 0 22 33 1 0 0 0 0 23 27 1 0 0 0 0 23 29 1 6 0 0 0 24 30 2 0 0 0 0 24 33 1 0 0 0 0 25 31 1 1 0 0 0 26 27 1 0 0 0 0 26 32 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11134719
ChEMBL	CHEMBL460241
ZINC

Physicochemical Properties

Molecular Weight:	489.25
ALogP:	3.7752
MLogP:	3.66
XLogP:	3.032
# Rotatable Bonds:	11
Polar Surface Area:	124.96
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	34

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