NPASS drugs

Drug Information

Drug ID:	NPD6776
Drug Name:	Daunorubicin Citrate
Molecular Formula:	C27H29NO10.C6H8O7
Canonical SMILES:	OC(=O)C(CC(=O)O)(CC(=O)O)O.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.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t10-,14-,16-,17-,22+,27-;/m0./s1"
Standard InCHIKey:	VNTHYLVDGVBPOU-QQYBVWGSSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD6776

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	49636
0.1-0.2	156330
0.2-0.3	5479
0.3-0.4	181
0.4-0.5	44
0.5-0.6	19
0.6-0.7	23
0.7-0.8	20
0.8-0.85	2
0.85-0.9	5
0.9-0.95	0
0.95-1	0

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	0.8537	NPC55094
High Similarity	0.8537	NPC109403
High Similarity	0.8537	NPC37318
High Similarity	0.8537	NPC559703
High Similarity	0.8537	NPC612087
Intermediate Similarity	0.8434	NPC487573
Intermediate Similarity	0.8434	NPC611676
Intermediate Similarity	0.7816	NPC261012
Intermediate Similarity	0.7816	NPC314738
Intermediate Similarity	0.7816	NPC23467
Intermediate Similarity	0.7816	NPC599904
Intermediate Similarity	0.7727	NPC468994
Intermediate Similarity	0.7727	NPC599791
Intermediate Similarity	0.7442	NPC503116
Intermediate Similarity	0.7386	NPC510219
Intermediate Similarity	0.7386	NPC572620
Intermediate Similarity	0.7356	NPC532268
Intermediate Similarity	0.7356	NPC574720
Intermediate Similarity	0.7356	NPC582713
Intermediate Similarity	0.7356	NPC603200
Intermediate Similarity	0.7111	NPC549797
Intermediate Similarity	0.7111	NPC601855
Intermediate Similarity	0.7024	NPC569653
Intermediate Similarity	0.7024	NPC611971
Intermediate Similarity	0.7	NPC515159
Intermediate Similarity	0.7	NPC517461
Intermediate Similarity	0.7	NPC569191
Remote Similarity	0.69	NPC544248
Remote Similarity	0.69	NPC583546
Remote Similarity	0.69	NPC586088
Remote Similarity	0.6632	NPC524103
Remote Similarity	0.6632	NPC551304
Remote Similarity	0.6632	NPC573717
Remote Similarity	0.6632	NPC587726
Remote Similarity	0.6632	NPC593984
Remote Similarity	0.6632	NPC600087
Remote Similarity	0.6495	NPC512117
Remote Similarity	0.6495	NPC548113
Remote Similarity	0.6495	NPC567919
Remote Similarity	0.6465	NPC558539
Remote Similarity	0.6465	NPC559618
Remote Similarity	0.6465	NPC573204
Remote Similarity	0.6421	NPC580365
Remote Similarity	0.6421	NPC594153
Remote Similarity	0.625	NPC530848
Remote Similarity	0.617	NPC541072
Remote Similarity	0.617	NPC576886
Remote Similarity	0.6154	NPC496533
Remote Similarity	0.6154	NPC582117
Remote Similarity	0.6064	NPC502879
Remote Similarity	0.5963	NPC99361
Remote Similarity	0.5963	NPC577128
Remote Similarity	0.5893	NPC496202
Remote Similarity	0.5893	NPC532430
Remote Similarity	0.5893	NPC597507
Remote Similarity	0.5841	NPC256596
Remote Similarity	0.5841	NPC307834
Remote Similarity	0.581	NPC521532
Remote Similarity	0.57	NPC498484
Remote Similarity	0.57	NPC555495
Remote Similarity	0.57	NPC579843
Remote Similarity	0.5648	NPC522051
Remote Similarity	0.5638	NPC303373
Remote Similarity	0.5638	NPC517282
Remote Similarity	0.5638	NPC541278
Remote Similarity	0.5638	NPC602774
Remote Similarity	0.5361	NPC553292
Remote Similarity	0.5327	NPC495567
Remote Similarity	0.5149	NPC516556

Drug Structure

NPD6776 OpenBabel08211710072D 61 64 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 2.4641 -8.8660 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 7.4282 -8.0000 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 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 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 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 12.5263 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5263 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0263 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6603 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5263 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5263 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0263 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5263 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6603 -4.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7942 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.0263 -3.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.0263 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.5263 -1.2321 0.0000 O 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 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 13.5263 -0.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7942 -2.2321 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.0263 -1.3660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3923 -0.7321 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 52 1 0 0 0 0 28 53 1 0 0 0 0 30 54 1 0 0 0 0 32 55 1 0 0 0 0 34 56 1 0 0 0 0 35 57 1 0 0 0 0 39 41 1 0 0 0 0 39 44 1 0 0 0 0 40 42 1 0 0 0 0 40 44 1 0 0 0 0 41 45 2 0 0 0 0 41 46 1 0 0 0 0 42 47 2 0 0 0 0 42 48 1 0 0 0 0 43 44 1 0 0 0 0 43 49 2 0 0 0 0 43 50 1 0 0 0 0 44 51 1 0 0 0 0 46 58 1 0 0 0 0 48 59 1 0 0 0 0 50 60 1 0 0 0 0 51 61 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	527.18
ALogP	-3.7468
MLogP	3.22
XLogP	-1.071
HDA	8
HBD	5
Rotatable Bonds	12
TPSA	185.84
RO5 Violation	0