NPASS Compound

Natural Product: NPC279871

Natural Product ID	NPC279871
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Molassamide
IUPAC Name	(2S,3R)-N-[(2S,5S,8S,11R,12S,15Z,18S,21R)-2-benzyl-15-ethylidene-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-[[(2S)-2-(butanoylamino)propanoyl]amino]-3-hydroxybutanamide
Synonyms	Molassamide
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1077010
PubChem CID	45379965
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 135138 0 0 0 0 0 0 0 0999 V2000 9.9527 1.3771 5.4848 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4847 0.1844 4.6840 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5005 0.5615 3.2030 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0555 -0.5862 2.3756 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1953 -0.4749 1.4565 N 0 0 0 0 0 0 0 0 0 0 0 0 7.4675 0.6459 0.9756 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3653 1.8083 0.6329 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7268 0.2594 -0.3000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8100 -0.9369 -0.6512 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3303 -1.7223 -1.6933 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6863 -3.1756 -1.3851 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3042 -3.5725 0.0193 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2597 -4.0641 -2.3341 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8938 -1.5841 -2.0743 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1374 -0.8310 -1.4659 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7818 -0.4396 -1.5160 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4360 0.4691 -2.6362 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6430 -0.1581 -4.0237 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0497 0.8734 -2.6591 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7096 2.1816 -2.8489 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7137 2.9717 -2.9946 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6148 2.7535 -2.9056 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5188 4.1285 -2.1963 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4839 5.0361 -2.9098 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8487 4.8345 -2.1541 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7571 2.0671 -2.6094 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3226 1.0287 -2.2973 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8051 0.9703 -2.1116 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3427 2.3769 -2.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8080 2.4691 -2.2833 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4571 2.8060 -1.1298 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8286 2.8799 -1.0678 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5478 2.6041 -2.2083 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9410 2.2594 -3.3982 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5578 2.1991 -3.4066 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9553 2.6738 -2.1719 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 0.5463 -0.7758 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6281 1.2181 0.3263 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0849 -0.4814 -0.5552 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5242 -0.9286 -1.6141 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5525 -1.0534 0.7622 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5590 -0.0923 1.2221 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2854 -0.1854 2.4492 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4070 -0.9580 2.6605 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1377 -1.0058 3.8109 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7253 -0.2125 4.8639 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6110 0.5882 4.7275 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8944 0.6084 3.5394 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5031 -1.5531 1.5338 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.4071 -1.9971 2.8922 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5081 -1.0026 3.5962 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1417 -0.8926 2.9548 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0594 -1.9087 1.8649 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2052 -1.7999 0.9860 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1917 -1.9005 -0.1887 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7841 -1.9828 1.1814 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3342 -3.0964 0.7087 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9195 -3.2195 0.0283 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2895 -4.4067 -0.4157 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6009 -4.5652 -1.1323 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7663 -2.1203 -0.1790 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8631 -1.5960 -1.3735 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1136 -2.1629 -2.3651 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1097 -4.2267 0.8718 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5734 -2.1554 3.5539 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5526 -0.1325 -2.1112 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4927 -2.3584 -3.1492 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0318 1.2318 -0.9644 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5844 -1.8675 2.5798 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0625 1.4164 5.5355 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5050 1.3254 6.4956 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6306 2.2976 4.9900 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1604 -0.6694 4.8765 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4342 -0.0441 4.9525 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7853 1.4247 3.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5035 0.9378 2.9559 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6975 1.0128 1.6823 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2619 2.0013 -0.4708 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4318 1.5323 0.7721 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0777 2.7105 1.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8887 -1.4557 -2.6329 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8171 -3.2012 -1.4069 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4441 -2.6912 0.6886 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2664 -3.9093 0.1158 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0183 -4.3624 0.3450 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0104 -4.9373 -1.9070 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6051 0.1670 -0.5650 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1054 1.3812 -2.6980 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0539 0.5118 -4.7283 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1858 -1.1302 -4.0884 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6990 -0.0715 -4.3418 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7565 3.1202 -4.0181 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1613 4.0045 -1.1604 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3974 5.0805 -2.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0412 6.0705 -2.8783 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6009 4.6806 -3.9326 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6360 5.9366 -2.2729 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4776 4.4800 -2.9778 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2846 4.7407 -1.1465 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2624 0.3495 -2.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0260 2.6607 -3.3858 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9173 3.0960 -1.6563 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9219 3.0337 -0.1976 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3503 3.1535 -0.1365 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5301 2.0438 -4.2949 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1007 1.9230 -4.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5095 1.9316 -2.6292 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9472 0.9053 1.3391 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5198 0.9540 0.3364 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6942 2.3328 0.2178 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1315 -2.0188 0.4244 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3660 -0.1351 0.3886 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2151 0.9848 1.0513 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7619 -1.6006 1.8402 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0204 -1.6312 3.9403 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2958 -0.2299 5.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3195 1.2000 5.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0368 1.2357 3.4470 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9398 -3.0421 2.9580 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0099 -0.0029 3.5936 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3459 -1.2939 4.6639 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0610 0.1176 2.5081 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3358 -1.0349 3.7246 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0804 -2.9096 2.4351 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6627 -5.3020 -0.2784 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1771 -3.6432 -1.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3478 -4.7773 -2.1896 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1238 -5.4287 -0.6426 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2765 -2.6638 -2.1599 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1132 -4.1371 0.9012 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1544 -2.7751 3.0808 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0612 -0.5715 -2.9005 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5952 -2.7786 -3.1676 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9842 1.1743 -1.9954 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1119 -2.6854 2.1835 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 3 5 6 1 0 6 7 1 0 6 8 1 0 8 9 2 3 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 10 14 1 0 14 15 2 3 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 22 26 1 0 26 27 2 3 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 28 37 1 0 37 38 1 0 37 39 1 0 39 40 2 0 39 41 1 0 41 42 1 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 41 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 2 0 53 56 1 0 56 57 2 0 57 58 1 0 58 59 2 0 59 60 1 0 58 61 1 0 61 62 2 0 62 63 1 0 57 64 1 0 50 65 1 0 27 66 1 0 14 67 1 0 8 68 1 0 4 69 1 0 62 16 1 0 35 30 1 0 48 43 1 0 54 49 1 0 1 70 1 0 1 71 1 0 1 72 1 0 2 73 1 0 2 74 1 0 3 75 1 0 3 76 1 0 6 77 1 1 7 78 1 0 7 79 1 0 7 80 1 0 10 81 1 6 11 82 1 1 12 83 1 0 12 84 1 0 12 85 1 0 13 86 1 0 16 87 1 1 17 88 1 6 18 89 1 0 18 90 1 0 18 91 1 0 22 92 1 6 23 93 1 0 24 94 1 0 24 95 1 0 24 96 1 0 25 97 1 0 25 98 1 0 25 99 1 0 28100 1 6 29101 1 0 29102 1 0 31103 1 0 32104 1 0 34105 1 0 35106 1 0 36107 1 0 38108 1 0 38109 1 0 38110 1 0 41111 1 6 42112 1 0 42113 1 0 44114 1 0 45115 1 0 46116 1 0 47117 1 0 48118 1 0 50119 1 6 51120 1 0 51121 1 0 52122 1 0 52123 1 0 53124 1 1 59125 1 0 60126 1 0 60127 1 0 60128 1 0 63129 1 0 64130 1 0 65131 1 0 66132 1 0 67133 1 0 68134 1 0 69135 1 0 M END

Standard InCHIKey	KXSGCAPYMUMVSH-VFYPFKDGSA-N
Standard InCHI	InChI=1S/C48H66N8O13/c1-9-14-36(59)49-26(5)41(61)53-39(27(6)57)44(64)54-40-28(7)69-48(68)38(25(3)4)52-43(63)34(23-30-17-19-31(58)20-18-30)55(8)47(67)35(24-29-15-12-11-13-16-29)56-37(60)22-21-33(46(56)66)51-42(62)32(10-2)50-45(40)65/h10-13,15-20,25-28,33-35,37-40,57-58,60H,9,14,21-24H2,1-8H3,(H,49,59)(H,50,65)(H,51,62)(H,52,63)(H,53,61)(H,54,64)/b32-10-/t26-,27+,28+,33-,34-,35-,37+,38-,39-,40-/m0/s1
SMILES	CCCC(=N[C@@H](C)C(=N[C@@H]([C@@H](C)O)C(=N[C@H]1[C@@H](C)OC(=O)[C@H](C(C)C)N=C([C@H](Cc2ccc(cc2)O)N(C)C(=O)[C@H](Cc2ccccc2)N2[C@@H](CC[C@@H](C2=O)N=C(/C(=C/C)/N=C1O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4193	Dichothrix utahensis	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20020755]
NPO4193	Dichothrix utahensis	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2682	Individual protein	Alpha-chymotrypsin	Bos taurus	IC50	=	234.0	nM	PMID[18271552]
NPT4417	Individual protein	Elastase 1	Sus scrofa	IC50	=	32.0	nM	PMID[18271552]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

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.

● The left chart: Distribution of similarity level between NPC279871 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	10743
0.1-0.2	37069
0.2-0.3	1861
0.3-0.4	125
0.4-0.5	24
0.5-0.6	22
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8302	Intermediate Similarity	NPC194671
0.7982	Intermediate Similarity	NPC269750
0.7818	Intermediate Similarity	NPC294951
0.735	Intermediate Similarity	NPC163961
0.7034	Intermediate Similarity	NPC488263
0.6696	Remote Similarity	NPC137627
0.6607	Remote Similarity	NPC306804
0.6387	Remote Similarity	NPC471050
0.6364	Remote Similarity	NPC159767
0.6311	Remote Similarity	NPC155506
0.6055	Remote Similarity	NPC163392
0.6031	Remote Similarity	NPC473305
0.6016	Remote Similarity	NPC240130
0.5982	Remote Similarity	NPC239762
0.5968	Remote Similarity	NPC471048
0.584	Remote Similarity	NPC302715
0.5785	Remote Similarity	NPC471052
0.5714	Remote Similarity	NPC476227
0.5714	Remote Similarity	NPC40234
0.5702	Remote Similarity	NPC50016
0.5591	Remote Similarity	NPC487289
0.5581	Remote Similarity	NPC61332
0.552	Remote Similarity	NPC471053
0.5397	Remote Similarity	NPC45037
0.5397	Remote Similarity	NPC471051
0.5391	Remote Similarity	NPC230611
0.5328	Remote Similarity	NPC281049
0.5312	Remote Similarity	NPC107938
0.5271	Remote Similarity	NPC294516
0.5191	Remote Similarity	NPC46009
0.5152	Remote Similarity	NPC65714
0.5152	Remote Similarity	NPC473371
0.5149	Remote Similarity	NPC473404
0.5116	Remote Similarity	NPC471526
0.5076	Remote Similarity	NPC102959

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC279871 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2965
0.1-0.2	5931
0.2-0.3	249
0.3-0.4	5
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data