NPASS drugs

Drug Information

Drug ID:	NPD37
Drug Name:	Podophyllin
Molecular Formula:	2C22H24O9.2C22H22O8
Canonical SMILES:	OCC1C(O)c2cc3OCOc3cc2C(C1C(=O)O)c1cc(OC)c(c(c1)OC)OC.OCC1C(O)c2cc3OCOc3cc2C(C1C(=O)O)c1cc(OC)c(c(c1)OC)OC.COc1cc(cc(c1OC)OC)C1C2C(=O)OCC2C(c2c1cc1OCOc1c2)O.COc1cc(cc(c1OC)OC)C1C2C(=O)OCC2C(c2c1cc1OCOc1c2)O
Standard InCHI:	"InChI=1S/2C22H24O9.2C22H22O8/c21-27-16-4-10(5-17(28-2)21(16)29-3)18-11-6-14-15(31-9-30-14)7-12(11)20(24)13(8-23)19(18)22(25)26;21-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h24-7,13,18-20,23-24H,8-9H2,1-3H3,(H,25,26);24-7,13,18-20,23H,8-9H2,1-3H3"
Standard InCHIKey:	KOUZYZCESNTXJO-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD37

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	98846
0.1-0.2	110058
0.2-0.3	2596
0.3-0.4	143
0.4-0.5	64
0.5-0.6	15
0.6-0.7	7
0.7-0.8	10
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	0.7429	NPC237946
Intermediate Similarity	0.7429	NPC226168
Intermediate Similarity	0.7429	NPC32373
Intermediate Similarity	0.7429	NPC318335
Intermediate Similarity	0.7429	NPC10635
Intermediate Similarity	0.7429	NPC494981
Intermediate Similarity	0.7429	NPC608448
Intermediate Similarity	0.7429	NPC611758
Intermediate Similarity	0.7286	NPC315054
Intermediate Similarity	0.7286	NPC245948
Remote Similarity	0.68	NPC119910
Remote Similarity	0.6479	NPC321164
Remote Similarity	0.6479	NPC306487
Remote Similarity	0.6479	NPC220722
Remote Similarity	0.6234	NPC91634
Remote Similarity	0.6234	NPC150943
Remote Similarity	0.6234	NPC268718
Remote Similarity	0.5897	NPC207584
Remote Similarity	0.5897	NPC19947
Remote Similarity	0.5843	NPC272234
Remote Similarity	0.5732	NPC258388
Remote Similarity	0.5488	NPC509671
Remote Similarity	0.5455	NPC239890
Remote Similarity	0.5455	NPC94759
Remote Similarity	0.5455	NPC169037
Remote Similarity	0.5455	NPC209411
Remote Similarity	0.5455	NPC279624
Remote Similarity	0.5455	NPC515784
Remote Similarity	0.5316	NPC178574
Remote Similarity	0.5301	NPC288149
Remote Similarity	0.5119	NPC258499
Remote Similarity	0.5059	NPC8838

Drug Structure

NPD37 OpenBabel08201723032D 130144 0 0 1 0 0 0 0 0999 V2000 15.1632 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2972 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.0292 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4311 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5651 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8331 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1010 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8331 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7646 -0.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5651 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8331 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9670 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8331 -5.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.9670 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1010 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2972 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4311 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6991 -4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.6991 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.9670 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 14.2972 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5651 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9670 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1010 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.4311 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5651 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.1632 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.4311 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.1632 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7591 -1.0219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3579 -1.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 23.9574 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 23.0914 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 24.8235 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 22.2254 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 21.3593 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.6273 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.8952 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.6273 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.5588 -0.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 21.3593 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.6273 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.7613 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.6273 -5.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 18.7613 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.8952 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 23.0914 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 22.2254 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.4933 -4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 20.4933 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 18.7613 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 23.0914 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 21.3593 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.4933 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 17.8952 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 21.3593 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 22.2254 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 23.9574 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 22.2254 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 23.9574 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.5534 -1.0219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 17.1521 -1.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2810 -2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.6962 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.2321 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0981 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0981 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2810 -3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9720 -4.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -8.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6932 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6472 -3.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6472 -2.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2350 -15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5651 -16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9670 -17.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9670 -14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6991 -14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5651 -12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5651 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0160 -10.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9700 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8331 -13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6991 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6991 -11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9670 -11.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.4311 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4311 -11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9670 -15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6991 -15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8331 -12.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.9670 -12.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.8331 -10.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.8331 -15.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0160 -12.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8331 -9.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7070 -13.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1010 -15.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5651 -15.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8331 -16.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4282 -11.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.3822 -12.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.3822 -10.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1010 -6.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2350 -5.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6991 -7.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 20.4933 -8.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.0292 -5.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 23.0914 -5.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -0.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6991 -9.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 10 1 0 0 0 0 5 17 2 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 23 1 0 0 0 0 9 30 1 0 0 0 0 9 31 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 21 2 0 0 0 0 16 27 1 0 0 0 0 17 21 1 0 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 19 22 1 0 0 0 0 20 24 1 0 0 0 0 21 29 1 0 0 0 0 22 25 2 0 0 0 0 22 26 1 0 0 0 0 23123 1 0 0 0 0 24124 1 0 0 0 0 26125 1 0 0 0 0 32 58 1 0 0 0 0 33 59 1 0 0 0 0 34 60 1 0 0 0 0 35 41 2 0 0 0 0 35 47 1 0 0 0 0 36 41 1 0 0 0 0 36 48 2 0 0 0 0 37 42 2 0 0 0 0 37 45 1 0 0 0 0 38 43 2 0 0 0 0 38 46 1 0 0 0 0 39 44 1 0 0 0 0 39 54 1 0 0 0 0 40 61 1 0 0 0 0 40 62 1 0 0 0 0 41 49 1 0 0 0 0 42 43 1 0 0 0 0 42 49 1 0 0 0 0 43 51 1 0 0 0 0 44 50 1 0 0 0 0 44 51 1 0 0 0 0 45 46 2 0 0 0 0 45 61 1 0 0 0 0 46 62 1 0 0 0 0 47 52 2 0 0 0 0 47 58 1 0 0 0 0 48 52 1 0 0 0 0 48 59 1 0 0 0 0 49 50 1 0 0 0 0 50 53 1 0 0 0 0 51 55 1 0 0 0 0 52 60 1 0 0 0 0 53 56 2 0 0 0 0 53 57 1 0 0 0 0 54126 1 0 0 0 0 55127 1 0 0 0 0 57128 1 0 0 0 0 63 87 1 0 0 0 0 64 88 1 0 0 0 0 65 89 1 0 0 0 0 66 72 2 0 0 0 0 66 78 1 0 0 0 0 67 72 1 0 0 0 0 67 79 2 0 0 0 0 68 73 2 0 0 0 0 68 76 1 0 0 0 0 69 74 2 0 0 0 0 69 77 1 0 0 0 0 70 75 1 0 0 0 0 70 90 1 0 0 0 0 71 91 1 0 0 0 0 71 92 1 0 0 0 0 72 80 1 0 0 0 0 73 74 1 0 0 0 0 73 80 1 0 0 0 0 74 82 1 0 0 0 0 75 81 1 0 0 0 0 75 82 1 0 0 0 0 76 77 2 0 0 0 0 76 91 1 0 0 0 0 77 92 1 0 0 0 0 78 83 2 0 0 0 0 78 87 1 0 0 0 0 79 83 1 0 0 0 0 79 88 1 0 0 0 0 80 81 1 0 0 0 0 81 84 1 0 0 0 0 82 85 1 0 0 0 0 83 89 1 0 0 0 0 84 86 2 0 0 0 0 84 90 1 0 0 0 0 85129 1 0 0 0 0 93117 1 0 0 0 0 94118 1 0 0 0 0 95119 1 0 0 0 0 96102 2 0 0 0 0 96108 1 0 0 0 0 97102 1 0 0 0 0 97109 2 0 0 0 0 98103 2 0 0 0 0 98106 1 0 0 0 0 99104 2 0 0 0 0 99107 1 0 0 0 0 100105 1 0 0 0 0 100120 1 0 0 0 0 101121 1 0 0 0 0 101122 1 0 0 0 0 102110 1 0 0 0 0 103104 1 0 0 0 0 103110 1 0 0 0 0 104112 1 0 0 0 0 105111 1 0 0 0 0 105112 1 0 0 0 0 106107 2 0 0 0 0 106121 1 0 0 0 0 107122 1 0 0 0 0 108113 2 0 0 0 0 108117 1 0 0 0 0 109113 1 0 0 0 0 109118 1 0 0 0 0 110111 1 0 0 0 0 111114 1 0 0 0 0 112115 1 0 0 0 0 113119 1 0 0 0 0 114116 2 0 0 0 0 114120 1 0 0 0 0 115130 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank	DB09094
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	0
ChEBI
CAS Number	9000-55-9

Drug Properties

Molecular Weight	432.14
ALogP	-2.1096
MLogP	2.89
XLogP	0.868
HDA	4
HBD	3
Rotatable Bonds	12
TPSA	123.91
RO5 Violation	0