NPASS drugs

Drug Information

Drug ID:	NPD6778
Drug Name:	Daunorubicin
Molecular Formula:	C27H29NO10
Canonical SMILES:	COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@H]1C[C@H](N)[C@@H]([C@@H](O1)C)O)C[C@](C2)(O)C(=O)C
Standard InCHI:	"InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1"
Standard InCHIKey:	STQGQHZAVUOBTE-VGBVRHCVSA-N
Max Developmental Stage:	Phase 4
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6778

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	48444
0.1-0.2	154725
0.2-0.3	8152
0.3-0.4	286
0.4-0.5	35
0.5-0.6	27
0.6-0.7	24
0.7-0.8	16
0.8-0.85	7
0.85-0.9	9
0.9-0.95	4
0.95-1	7

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	NPC55094
High Similarity	1.0	NPC109403
High Similarity	1.0	NPC37318
High Similarity	1.0	NPC559703
High Similarity	1.0	NPC612087
High Similarity	0.9859	NPC487573
High Similarity	0.9859	NPC611676
High Similarity	0.9067	NPC261012
High Similarity	0.9067	NPC314738
High Similarity	0.9067	NPC23467
High Similarity	0.9067	NPC599904
High Similarity	0.8947	NPC468994
High Similarity	0.8947	NPC599791
High Similarity	0.8649	NPC503116
High Similarity	0.8553	NPC510219
High Similarity	0.8553	NPC572620
High Similarity	0.8533	NPC532268
High Similarity	0.8533	NPC574720
High Similarity	0.8533	NPC582713
High Similarity	0.8533	NPC603200
Intermediate Similarity	0.8205	NPC549797
Intermediate Similarity	0.8205	NPC601855
Intermediate Similarity	0.8194	NPC569653
Intermediate Similarity	0.8194	NPC611971
Intermediate Similarity	0.8077	NPC515159
Intermediate Similarity	0.8077	NPC517461
Intermediate Similarity	0.8077	NPC569191
Intermediate Similarity	0.7381	NPC524103
Intermediate Similarity	0.7381	NPC551304
Intermediate Similarity	0.7381	NPC573717
Intermediate Similarity	0.7381	NPC587726
Intermediate Similarity	0.7381	NPC593984
Intermediate Similarity	0.7381	NPC600087
Intermediate Similarity	0.7356	NPC558539
Intermediate Similarity	0.7356	NPC559618
Intermediate Similarity	0.7356	NPC573204
Intermediate Similarity	0.7349	NPC580365
Intermediate Similarity	0.7349	NPC594153
Intermediate Similarity	0.7209	NPC512117
Intermediate Similarity	0.7209	NPC548113
Intermediate Similarity	0.7209	NPC567919
Intermediate Similarity	0.7073	NPC541072
Intermediate Similarity	0.7073	NPC576886
Remote Similarity	0.6957	NPC496533
Remote Similarity	0.6957	NPC582117
Remote Similarity	0.6951	NPC502879
Remote Similarity	0.6882	NPC530848
Remote Similarity	0.6882	NPC544248
Remote Similarity	0.6882	NPC583546
Remote Similarity	0.6882	NPC586088
Remote Similarity	0.6531	NPC99361
Remote Similarity	0.6531	NPC577128
Remote Similarity	0.6463	NPC303373
Remote Similarity	0.6463	NPC517282
Remote Similarity	0.6463	NPC541278
Remote Similarity	0.6463	NPC602774
Remote Similarity	0.6354	NPC522051
Remote Similarity	0.6292	NPC498484
Remote Similarity	0.6292	NPC555495
Remote Similarity	0.6292	NPC579843
Remote Similarity	0.6275	NPC496202
Remote Similarity	0.6275	NPC532430
Remote Similarity	0.6275	NPC597507
Remote Similarity	0.6214	NPC256596
Remote Similarity	0.6214	NPC307834
Remote Similarity	0.6118	NPC553292
Remote Similarity	0.6	NPC495567
Remote Similarity	0.5556	NPC57174
Remote Similarity	0.5556	NPC547493
Remote Similarity	0.5556	NPC560300
Remote Similarity	0.5532	NPC505892
Remote Similarity	0.5532	NPC548484
Remote Similarity	0.5532	NPC575491
Remote Similarity	0.5532	NPC596187
Remote Similarity	0.5402	NPC540376
Remote Similarity	0.5402	NPC585123
Remote Similarity	0.54	NPC521532
Remote Similarity	0.5361	NPC588029
Remote Similarity	0.5306	NPC522622
Remote Similarity	0.5275	NPC509403
Remote Similarity	0.525	NPC571088
Remote Similarity	0.525	NPC606929
Remote Similarity	0.5217	NPC530319
Remote Similarity	0.5217	NPC555117
Remote Similarity	0.5217	NPC603758
Remote Similarity	0.5176	NPC549127
Remote Similarity	0.5172	NPC549287
Remote Similarity	0.5155	NPC270631
Remote Similarity	0.5155	NPC500189
Remote Similarity	0.5125	NPC136943
Remote Similarity	0.5109	NPC511030
Remote Similarity	0.5109	NPC538928
Remote Similarity	0.5109	NPC564710
Remote Similarity	0.5098	NPC523556

Drug Structure

NPD6778 OpenBabel08211710072D 44 48 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 1.5000 3.8660 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 -3.4641 3.0000 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 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 -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 -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 -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 11 1 0 0 0 0 3 36 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 12 1 0 0 0 0 6 15 2 0 0 0 0 7 14 1 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 27 1 0 0 0 0 9 16 1 0 0 0 0 9 27 1 0 0 0 0 10 1 1 6 0 0 0 10 22 1 0 0 0 0 10 37 1 0 0 0 0 11 29 2 0 0 0 0 12 18 2 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 24 2 0 0 0 0 14 22 1 0 0 0 0 14 28 1 6 0 0 0 15 18 1 0 0 0 0 15 36 1 0 0 0 0 16 19 1 0 0 0 0 16 38 1 1 0 0 0 17 37 1 0 0 0 0 17 38 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 30 1 6 0 0 0 23 31 2 0 0 0 0 24 32 1 0 0 0 0 25 33 2 0 0 0 0 26 34 1 0 0 0 0 27 11 1 6 0 0 0 27 35 1 0 0 0 0 28 39 1 0 0 0 0 28 40 1 0 0 0 0 30 41 1 0 0 0 0 32 42 1 0 0 0 0 34 43 1 0 0 0 0 35 44 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNC000215; DAP000788; DNC000517
DrugBank	DB00694
ChEMBL	CHEMBL178
IUPHAR/BPS	7063
PharmaGKB	PA449212
KEGG Drug
PubChem CID	30323
ChEBI	41977
CAS Number	20830-81-3

Drug Properties

Molecular Weight	527.18
ALogP	-3.7468
MLogP	3.22
XLogP	-1.071
HDA	8
HBD	5
Rotatable Bonds	12
TPSA	185.84
RO5 Violation	0