NPASS drugs

Drug Information

Drug ID:	NPD6780
Drug Name:	Doxorubicin Hydrochloride
Molecular Formula:	C27H29NO11.ClH
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.Cl
Standard InCHI:	"InChI=1S/C27H29NO11.ClH/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;1H/t10-,13-,15-,17-,22+,27-;/m0./s1"
Standard InCHIKey:	MWWSFMDVAYGXBV-RUELKSSGSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD6780

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	49613
0.1-0.2	154648
0.2-0.3	7105
0.3-0.4	249
0.4-0.5	42
0.5-0.6	19
0.6-0.7	31
0.7-0.8	5
0.8-0.85	11
0.85-0.9	5
0.9-0.95	2
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	NPC468994
High Similarity	1.0	NPC599791
High Similarity	0.9865	NPC261012
High Similarity	0.9865	NPC314738
High Similarity	0.9865	NPC23467
High Similarity	0.9865	NPC599904
High Similarity	0.9079	NPC487573
High Similarity	0.9079	NPC611676
High Similarity	0.8947	NPC55094
High Similarity	0.8947	NPC109403
High Similarity	0.8947	NPC37318
High Similarity	0.8947	NPC559703
High Similarity	0.8947	NPC612087
Intermediate Similarity	0.8205	NPC503116
Intermediate Similarity	0.8125	NPC510219
Intermediate Similarity	0.8125	NPC572620
Intermediate Similarity	0.8101	NPC532268
Intermediate Similarity	0.8101	NPC574720
Intermediate Similarity	0.8101	NPC582713
Intermediate Similarity	0.8101	NPC603200
Intermediate Similarity	0.8049	NPC580365
Intermediate Similarity	0.8049	NPC594153
Intermediate Similarity	0.8025	NPC549797
Intermediate Similarity	0.8025	NPC601855
Intermediate Similarity	0.7308	NPC569653
Intermediate Similarity	0.7308	NPC611971
Intermediate Similarity	0.7262	NPC515159
Intermediate Similarity	0.7262	NPC517461
Intermediate Similarity	0.7262	NPC569191
Remote Similarity	0.6854	NPC524103
Remote Similarity	0.6854	NPC551304
Remote Similarity	0.6854	NPC573717
Remote Similarity	0.6854	NPC587726
Remote Similarity	0.6854	NPC593984
Remote Similarity	0.6854	NPC600087
Remote Similarity	0.6848	NPC558539
Remote Similarity	0.6848	NPC559618
Remote Similarity	0.6848	NPC573204
Remote Similarity	0.6744	NPC541072
Remote Similarity	0.6744	NPC576886
Remote Similarity	0.6703	NPC512117
Remote Similarity	0.6703	NPC548113
Remote Similarity	0.6703	NPC567919
Remote Similarity	0.6628	NPC502879
Remote Similarity	0.6327	NPC496533
Remote Similarity	0.6327	NPC582117
Remote Similarity	0.6263	NPC530848
Remote Similarity	0.6263	NPC544248
Remote Similarity	0.6263	NPC583546
Remote Similarity	0.6263	NPC586088
Remote Similarity	0.6196	NPC498484
Remote Similarity	0.6196	NPC555495
Remote Similarity	0.6196	NPC579843
Remote Similarity	0.618	NPC57174
Remote Similarity	0.618	NPC547493
Remote Similarity	0.618	NPC560300
Remote Similarity	0.6163	NPC303373
Remote Similarity	0.6163	NPC517282
Remote Similarity	0.6163	NPC541278
Remote Similarity	0.6163	NPC602774
Remote Similarity	0.5962	NPC99361
Remote Similarity	0.5962	NPC577128
Remote Similarity	0.5941	NPC522051
Remote Similarity	0.5741	NPC496202
Remote Similarity	0.5741	NPC532430
Remote Similarity	0.5741	NPC597507
Remote Similarity	0.5688	NPC256596
Remote Similarity	0.5688	NPC307834
Remote Similarity	0.5625	NPC136943
Remote Similarity	0.56	NPC495567
Remote Similarity	0.5495	NPC553292
Remote Similarity	0.534	NPC521532
Remote Similarity	0.5165	NPC540376
Remote Similarity	0.5165	NPC585123
Remote Similarity	0.5152	NPC505892
Remote Similarity	0.5152	NPC548484
Remote Similarity	0.5152	NPC575491
Remote Similarity	0.5152	NPC596187
Remote Similarity	0.5053	NPC509403

Drug Structure

NPD6780 OpenBabel08211710072D 47 50 0 0 1 0 0 0 0 0999 V2000 7.4282 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4641 -8.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -8.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -6.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -6.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -8.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -6.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -7.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -8.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1603 -6.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9641 -9.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -9.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -8.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -8.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6380 -1.0834 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 10.0263 -6.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -5.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9641 -9.7321 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -9.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -6.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4641 -8.8660 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 41 1 0 0 0 0 28 42 1 0 0 0 0 29 43 1 0 0 0 0 31 44 1 0 0 0 0 33 45 1 0 0 0 0 35 46 1 0 0 0 0 36 47 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	0
ChEBI
CAS Number

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