NPASS drugs

Drug Information

Drug ID:	NPD21
Drug Name:	Benzathine benzylpenicillin
Molecular Formula:	2C16H18N2O4S.C16H20N2
Canonical SMILES:	N(Cc1ccccc1)CCNCc1ccccc1.OC(=N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)Cc1ccccc1.OC(=N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)Cc1ccccc1
Standard InCHI:	"InChI=1S/2C16H18N2O4S.C16H20N2/c21-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h23-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);1-10,17-18H,11-14H2/t2*11-,12+,14-;/m11./s1"
Standard InCHIKey:	BVGLIYRKPOITBQ-ANPZCEIESA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD21

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	112259
0.1-0.2	96813
0.2-0.3	2638
0.3-0.4	17
0.4-0.5	7
0.5-0.6	4
0.6-0.7	0
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
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
Intermediate Similarity	0.7937	NPC90478
Remote Similarity	0.5775	NPC330588
Remote Similarity	0.5753	NPC468984
Remote Similarity	0.5556	NPC485035
Remote Similarity	0.5556	NPC469134

Drug Structure

NPD21 OpenBabel08201723032D 70 75 0 0 1 0 0 0 0 0999 V2000 3.5032 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5032 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7811 -4.2838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5223 -5.2497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0740 -3.5767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5564 -5.5085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1081 -3.8355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8834 -5.0603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8493 -4.8014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1763 -4.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5032 -3.9049 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1942 -1.9538 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5032 -3.9049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5032 -2.9049 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2431 -1.6448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0032 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2103 -4.6120 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5032 -2.9049 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4351 -3.3872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7961 -4.6120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0352 -0.6666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.3139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8122 -1.9538 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 8.7345 -9.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7345 -8.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -8.2177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2071 -7.5106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7588 -9.1836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1730 -7.7694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7247 -9.4424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3978 -8.9941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4319 -8.7353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6566 -9.9601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3296 -9.5118 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2807 -8.2028 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3296 -8.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3296 -9.5118 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5897 -7.2517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8685 -9.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6225 -10.2189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3296 -8.5118 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9495 -10.6672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6225 -7.8047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5679 -7.0438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9206 -6.5085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2807 -9.8208 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 10.6472 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.7093 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7811 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5132 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8433 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.7093 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7811 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5132 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9773 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8433 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3792 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2452 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6472 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1113 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6472 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9773 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5132 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 14.1113 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.4010 -3.1284 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7079 -3.2921 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9836 -10.4083 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9424 -6.7165 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5132 -0.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9773 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 9 2 0 0 0 0 7 9 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 17 2 3 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 6 0 0 0 12 15 1 1 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 18 1 0 0 0 0 14 23 1 6 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 19 65 1 0 0 0 0 22 66 1 0 0 0 0 24 39 1 0 0 0 0 25 39 1 0 0 0 0 26 27 2 0 0 0 0 26 28 1 0 0 0 0 27 29 1 0 0 0 0 28 30 2 0 0 0 0 29 32 2 0 0 0 0 30 32 1 0 0 0 0 31 32 1 0 0 0 0 31 33 1 0 0 0 0 33 40 2 3 0 0 0 33 42 1 0 0 0 0 34 36 1 0 0 0 0 34 37 1 0 0 0 0 34 40 1 6 0 0 0 35 38 1 1 0 0 0 35 39 1 0 0 0 0 35 41 1 0 0 0 0 36 41 1 0 0 0 0 36 43 2 0 0 0 0 37 41 1 0 0 0 0 37 46 1 6 0 0 0 38 44 2 0 0 0 0 38 45 1 0 0 0 0 39 46 1 0 0 0 0 42 67 1 0 0 0 0 45 68 1 0 0 0 0 47 49 2 0 0 0 0 47 50 1 0 0 0 0 48 51 2 0 0 0 0 48 52 1 0 0 0 0 49 53 1 0 0 0 0 50 54 2 0 0 0 0 51 55 1 0 0 0 0 52 56 2 0 0 0 0 53 61 2 0 0 0 0 54 61 1 0 0 0 0 55 62 2 0 0 0 0 56 62 1 0 0 0 0 57 58 1 0 0 0 0 57 63 1 0 0 0 0 58 64 1 0 0 0 0 59 61 1 0 0 0 0 59 63 1 0 0 0 0 60 62 1 0 0 0 0 60 64 1 0 0 0 0 63 69 1 0 0 0 0 64 70 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank	DB09323
ChEMBL	CHEMBL3182097
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	0
ChEBI	51352
CAS Number	1538-09-6

Drug Properties

Molecular Weight	334.1
ALogP	0.0813
MLogP	2.45
XLogP	2.874
HDA	6
HBD	2
Rotatable Bonds	8
TPSA	115.5
RO5 Violation	0