NPASS drugs

Drug Information

Drug ID:	NPD6782
Drug Name:	Doxorubicin
Molecular Formula:	C27H29NO11
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
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"
Standard InCHIKey:	AOJJSUZBOXZQNB-TZSSRYMLSA-N
Max Developmental Stage:	Phase 4
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6782

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	49223
0.1-0.2	154734
0.2-0.3	7397
0.3-0.4	260
0.4-0.5	37
0.5-0.6	20
0.6-0.7	34
0.7-0.8	5
0.8-0.85	11
0.85-0.9	2
0.9-0.95	5
0.95-1	6

Similar Natural Products

High Similarity: Tc>=0.85; Intermediate Similarity: 0.7 <= Tc < 0.85; Remote Similarity: 0.5 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC261012
High Similarity	1.0	NPC314738
High Similarity	1.0	NPC23467
High Similarity	1.0	NPC599904
High Similarity	0.9865	NPC468994
High Similarity	0.9865	NPC599791
High Similarity	0.9067	NPC55094
High Similarity	0.9067	NPC109403
High Similarity	0.9067	NPC37318
High Similarity	0.9067	NPC559703
High Similarity	0.9067	NPC612087
High Similarity	0.8947	NPC487573
High Similarity	0.8947	NPC611676
Intermediate Similarity	0.8312	NPC503116
Intermediate Similarity	0.8228	NPC510219
Intermediate Similarity	0.8228	NPC572620
Intermediate Similarity	0.8205	NPC532268
Intermediate Similarity	0.8205	NPC574720
Intermediate Similarity	0.8205	NPC582713
Intermediate Similarity	0.8205	NPC603200
Intermediate Similarity	0.8148	NPC580365
Intermediate Similarity	0.8148	NPC594153
Intermediate Similarity	0.8125	NPC549797
Intermediate Similarity	0.8125	NPC601855
Intermediate Similarity	0.7403	NPC569653
Intermediate Similarity	0.7403	NPC611971
Intermediate Similarity	0.7349	NPC515159
Intermediate Similarity	0.7349	NPC517461
Intermediate Similarity	0.7349	NPC569191
Remote Similarity	0.6932	NPC524103
Remote Similarity	0.6932	NPC551304
Remote Similarity	0.6932	NPC573717
Remote Similarity	0.6932	NPC587726
Remote Similarity	0.6932	NPC593984
Remote Similarity	0.6932	NPC600087
Remote Similarity	0.6923	NPC558539
Remote Similarity	0.6923	NPC559618
Remote Similarity	0.6923	NPC573204
Remote Similarity	0.6824	NPC541072
Remote Similarity	0.6824	NPC576886
Remote Similarity	0.6778	NPC512117
Remote Similarity	0.6778	NPC548113
Remote Similarity	0.6778	NPC567919
Remote Similarity	0.6706	NPC502879
Remote Similarity	0.6392	NPC496533
Remote Similarity	0.6392	NPC582117
Remote Similarity	0.6327	NPC530848
Remote Similarity	0.6327	NPC544248
Remote Similarity	0.6327	NPC583546
Remote Similarity	0.6327	NPC586088
Remote Similarity	0.6264	NPC498484
Remote Similarity	0.6264	NPC555495
Remote Similarity	0.6264	NPC579843
Remote Similarity	0.625	NPC57174
Remote Similarity	0.625	NPC547493
Remote Similarity	0.625	NPC560300
Remote Similarity	0.6235	NPC303373
Remote Similarity	0.6235	NPC517282
Remote Similarity	0.6235	NPC541278
Remote Similarity	0.6235	NPC602774
Remote Similarity	0.6019	NPC99361
Remote Similarity	0.6019	NPC577128
Remote Similarity	0.6	NPC522051
Remote Similarity	0.5794	NPC496202
Remote Similarity	0.5794	NPC532430
Remote Similarity	0.5794	NPC597507
Remote Similarity	0.5741	NPC256596
Remote Similarity	0.5741	NPC307834
Remote Similarity	0.5696	NPC136943
Remote Similarity	0.5657	NPC495567
Remote Similarity	0.5556	NPC553292
Remote Similarity	0.5392	NPC521532
Remote Similarity	0.5222	NPC540376
Remote Similarity	0.5222	NPC585123
Remote Similarity	0.5204	NPC505892
Remote Similarity	0.5204	NPC548484
Remote Similarity	0.5204	NPC575491
Remote Similarity	0.5204	NPC596187
Remote Similarity	0.5106	NPC509403
Remote Similarity	0.5053	NPC530319
Remote Similarity	0.5053	NPC555117
Remote Similarity	0.5053	NPC603758
Remote Similarity	0.505	NPC588029

Drug Structure

NPD6782 OpenBabel08211710072D 46 50 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 2 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 6.0622 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -4.7321 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -3.8660 0.0000 H 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 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 6 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 16 1 6 0 0 0 27 36 1 0 0 0 0 28 40 1 0 0 0 0 28 41 1 0 0 0 0 29 42 1 0 0 0 0 31 43 1 0 0 0 0 33 44 1 0 0 0 0 35 45 1 0 0 0 0 36 46 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000192; DNC000163
DrugBank	DB00997
ChEMBL	CHEMBL53463
IUPHAR/BPS	7069
PharmaGKB	PA449412
KEGG Drug	D03899
PubChem CID	31703
ChEBI	28748
CAS Number	23214-92-8

Drug Properties

Molecular Weight	543.17
ALogP	-4.4188
MLogP	3.11
XLogP	-1.679
HDA	9
HBD	6
Rotatable Bonds	13
TPSA	206.07
RO5 Violation	1