NPASS Natural Product

Natural Product: NPC314738

Natural Product ID:	NPC314738
Common Name:	Epirubicin
IUPAC Name:	(7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
Synonyms:	Ellence; Epirubicin
Molecular Formula:	C27H29NO11
Standard InCHIKey:	AOJJSUZBOXZQNB-VTZDEGQISA-N
Standard InCHI:	InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22-,27-/m0/s1
Canonical SMILES:	OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@H]([C@@H](O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
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	Collection Location	Collection Time	Reference
NPO28556.2	Streptomyces peucetius atcc 29050	Subspecies	Streptomycetaceae	Bacteria				StreptomeDB*
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria				StreptomeDB*

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Biological Activity

Activity Type	# Activity
IC50	40
Ki	1
Others	6

Activity Type	# Activity
Cell Line	35
Individual Protein	4
Others	8

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1097	Cell Line	MKN-45	Homo sapiens	IC50	=	660000	nM	22940450
NPT14	Individual Protein	Tyrosine-protein kinase FYN	Homo sapiens	IC50	=	5181	nM	DrugMatrix in vitro pharmacology data
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	0.51	ug/ml	21545109
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	24.3	%	25066952
NPT1668	Cell Line	NCI-H157	Homo sapiens	IC50	=	1720000	nM	22940450
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	1230000	nM	22940450
NPT1872	Cell Line	Bcap37	Homo sapiens	IC50	=	890000	nM	22940450
NPT2	Others	Unspecified		Activity	=	66	%	19481462
NPT2	Others	Unspecified		Activity	=	64	%	19481462
NPT2	Others	Unspecified		Activity	=	78.6	%	19481462

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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 NPC314738 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	223
0.1-0.2	1041
0.2-0.3	2510
0.3-0.4	6018
0.4-0.5	6781
0.5-0.6	4427
0.6-0.7	5749
0.7-0.8	3965
0.8-0.85	146
0.85-0.9	25
0.9-0.95	0
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.7947	Intermediate Similarity	NPC478000
0.7947	Intermediate Similarity	NPC477683
0.7949	Intermediate Similarity	NPC264302
0.795	Intermediate Similarity	NPC314946
0.7957	Intermediate Similarity	NPC225419

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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 NPC314738 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	686
0.2-0.3	1459
0.3-0.4	2461
0.4-0.5	2393
0.5-0.6	1363
0.6-0.7	464
0.7-0.8	113
0.8-0.85	2
0.85-0.9	11
0.9-0.95	7
0.95-1	16

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6794	Remote Similarity	NPD7282	Approved
0.68	Remote Similarity	NPD8469	Approved
0.68	Remote Similarity	NPD4956	Approved
0.6802	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2675	Approved

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Structure

CID314738 OpenBabel06191716132D 39 43 0 0 1 0 0 0 0 0999 V2000 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 -0.8660 -2.5000 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 -1.5000 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 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 0.0000 -1.0000 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 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 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 1.5000 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 0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -4.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.7321 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 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 37 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 11 1 0 0 0 0 5 14 2 0 0 0 0 6 13 1 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 7 27 1 0 0 0 0 8 15 1 0 0 0 0 8 27 1 0 0 0 0 9 16 1 0 0 0 0 9 29 1 0 0 0 0 10 1 1 6 0 0 0 10 22 1 0 0 0 0 10 38 1 0 0 0 0 11 18 2 0 0 0 0 11 23 1 0 0 0 0 12 19 1 0 0 0 0 12 24 2 0 0 0 0 13 22 1 0 0 0 0 13 28 1 6 0 0 0 14 18 1 0 0 0 0 14 37 1 0 0 0 0 15 19 1 0 0 0 0 15 39 1 1 0 0 0 16 27 1 0 0 0 0 16 30 2 0 0 0 0 17 38 1 0 0 0 0 17 39 1 1 0 0 0 18 25 1 0 0 0 0 19 26 2 0 0 0 0 20 21 2 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 22 31 1 1 0 0 0 23 32 2 0 0 0 0 24 33 1 0 0 0 0 25 34 2 0 0 0 0 26 35 1 0 0 0 0 27 36 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	41867
ChEMBL	CHEMBL417
ZINC

Physicochemical Properties

Molecular Weight:	543.17
ALogP:	-4.4188
MLogP:	3.11
XLogP:	-1.679
# Rotatable Bonds:	13
Polar Surface Area:	206.07
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	39

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