NPASS Compound

Natural Product: NPC489625

Natural Product ID	NPC489625
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HGGAWGHAMKKZMS-KJCFDAGBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101893681
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

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 139144 0 0 0 0 0 0 0 0999 V2000 -5.2752 6.1179 0.5951 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8221 4.6465 0.7164 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3860 4.6039 0.2859 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3794 5.1270 -1.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7435 3.2698 0.2953 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3088 3.3896 -0.1778 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9845 2.9685 -1.2754 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2745 3.9783 0.5812 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3390 4.7383 1.7573 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0588 4.8505 2.3010 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 4.1204 1.3721 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0897 3.8856 0.1475 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4022 2.4692 -0.2495 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0855 2.1396 -1.1665 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8820 2.5321 -2.2495 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9840 3.4120 -1.7249 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9447 3.9631 -2.6996 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7499 3.0231 -3.5089 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3286 5.0053 -3.6210 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5293 1.1853 -2.7060 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9217 0.3991 -1.9116 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4603 -0.6861 -1.2420 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9703 -0.1365 0.0790 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6560 -1.0127 0.9849 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2125 -1.5169 2.1838 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2099 -2.2749 2.7212 N 0 0 0 0 0 0 0 0 0 0 0 0 7.2687 -2.2648 1.8977 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5401 -2.8453 1.9035 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4502 -2.6741 0.8952 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1097 -1.8775 -0.2076 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8773 -1.2917 -0.2511 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9719 -1.4883 0.7955 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3217 -1.6598 -1.0431 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1697 -1.1792 -1.1469 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3517 -3.0013 -0.7660 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4003 -3.9122 -0.4111 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8131 -4.5110 0.8744 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2827 -4.2927 0.7455 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2008 -3.8602 -0.7265 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9089 -3.4814 -1.1974 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1460 -3.7472 -0.5162 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5184 -3.4112 -0.9271 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8283 -4.3804 -2.0523 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1686 -4.2516 -2.6642 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6575 -5.8201 -1.5724 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3576 -3.6031 0.2720 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4244 -3.0641 0.5832 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.4056 -2.1696 0.2411 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7681 -2.7789 0.5950 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9196 -1.8961 0.2600 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8745 -4.0141 -0.3110 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1782 -4.7345 -0.0971 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3004 -0.7777 0.6392 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5276 -0.0479 -0.0748 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8770 -0.0406 1.6713 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5850 -0.3678 2.8391 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5445 0.7944 3.0976 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9110 1.9606 2.4373 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7182 1.4325 1.7029 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4226 1.8639 2.1787 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5631 2.6399 1.5958 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9583 1.4147 3.4464 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8291 -4.5696 1.1925 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7367 -2.8179 -2.3968 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5950 1.0082 -4.0873 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8012 1.5094 0.5808 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2998 6.2031 0.2119 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1702 6.6614 1.5416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5946 6.5765 -0.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8504 4.4611 1.8171 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5040 4.0079 0.1324 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8680 5.3312 0.9607 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3781 5.1138 -1.5857 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8702 6.1129 -1.1959 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7320 4.4440 -1.7433 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3015 2.5784 -0.3458 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6735 5.8054 1.5356 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9703 4.3132 2.5712 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3811 5.9142 2.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1180 4.3499 3.3187 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8952 4.6356 1.1796 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2606 3.1245 1.8204 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2683 4.5742 -0.6769 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4357 2.9745 -3.1224 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5732 2.7516 -1.0134 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5919 4.2124 -1.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6894 4.5715 -2.0851 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8170 3.4114 -3.5599 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4483 2.9643 -4.5647 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8097 2.0519 -3.0216 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0440 5.8021 -3.8726 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9207 4.5083 -4.5170 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4162 5.4322 -3.0906 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2340 -1.2748 -1.7866 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5897 0.7710 -0.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0377 0.2722 0.5836 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2468 -1.3591 2.6522 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1661 -2.7756 3.6203 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7972 -3.4571 2.7505 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4375 -3.1158 0.8793 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7742 -1.7052 -1.0209 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5549 -0.6737 -1.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3947 -3.5268 -0.3186 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4524 -4.7587 -1.1656 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0020 -5.5999 0.8522 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2147 -4.0906 1.7895 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9096 -3.5239 1.4090 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7581 -5.2400 0.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5076 -4.8520 -1.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6286 -2.3910 -1.2852 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0364 -4.1975 -2.8396 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5772 -3.2300 -2.7287 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9403 -4.9133 -2.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0890 -4.6758 -3.7371 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8443 -5.7863 -0.8216 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5795 -6.2921 -1.2566 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2126 -6.3987 -2.4342 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4274 -2.1262 -0.9186 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7591 -3.1527 1.6221 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6665 -1.9709 1.0961 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7017 -0.8367 0.1291 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4789 -2.2435 -0.6468 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8226 -3.7080 -1.3773 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0534 -4.7213 -0.1489 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9435 -4.1073 0.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5902 -5.2046 -1.0254 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9833 -5.5719 0.6052 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1788 -1.2644 2.8979 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8770 -0.4476 3.7387 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6391 0.8944 4.1944 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5501 0.6066 2.7066 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6204 2.5205 1.7716 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5774 2.6517 3.2806 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8182 1.8088 0.6417 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9826 1.2009 3.5923 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4588 -5.0656 1.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0247 -2.1017 -2.5489 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9427 0.1420 -4.4782 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2899 0.6151 0.7311 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 3 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 3 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 15 20 1 0 20 21 2 3 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 22 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 2 3 41 42 1 0 42 43 1 0 43 44 1 0 43 45 1 0 42 46 1 0 46 47 2 3 47 48 1 0 48 49 1 0 49 50 1 0 49 51 1 0 51 52 1 0 48 53 1 0 53 54 2 0 53 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 2 3 60 62 1 0 46 63 1 0 40 64 1 0 20 65 1 0 13 66 1 0 61 5 1 0 12 8 1 0 32 24 1 0 39 35 1 0 59 55 1 0 32 27 1 0 1 67 1 0 1 68 1 0 1 69 1 0 2 70 1 0 2 71 1 0 3 72 1 1 4 73 1 0 4 74 1 0 4 75 1 0 5 76 1 6 9 77 1 0 9 78 1 0 10 79 1 0 10 80 1 0 11 81 1 0 11 82 1 0 12 83 1 6 15 84 1 6 16 85 1 0 16 86 1 0 17 87 1 0 18 88 1 0 18 89 1 0 18 90 1 0 19 91 1 0 19 92 1 0 19 93 1 0 22 94 1 6 23 95 1 0 23 96 1 0 25 97 1 0 26 98 1 0 28 99 1 0 29100 1 0 30101 1 0 31102 1 0 36103 1 0 36104 1 0 37105 1 0 37106 1 0 38107 1 0 38108 1 0 39109 1 6 42110 1 6 43111 1 0 44112 1 0 44113 1 0 44114 1 0 45115 1 0 45116 1 0 45117 1 0 48118 1 6 49119 1 1 50120 1 0 50121 1 0 50122 1 0 51123 1 0 51124 1 0 52125 1 0 52126 1 0 52127 1 0 56128 1 0 56129 1 0 57130 1 0 57131 1 0 58132 1 0 58133 1 0 59134 1 6 62135 1 0 63136 1 0 64137 1 0 65138 1 0 66139 1 0 M END

Standard InCHIKey	HGGAWGHAMKKZMS-KJCFDAGBSA-N
Standard InCHI	InChI=1S/C49H73N9O8/c1-9-29(7)40-48(65)57-22-14-18-36(57)43(60)51-34(24-27(3)4)42(59)52-35(25-31-26-50-33-17-12-11-16-32(31)33)47(64)56-21-13-19-37(56)44(61)53-39(28(5)6)46(63)55-41(30(8)10-2)49(66)58-23-15-20-38(58)45(62)54-40/h11-12,16-17,26-30,34-41,50H,9-10,13-15,18-25H2,1-8H3,(H,51,60)(H,52,59)(H,53,61)(H,54,62)(H,55,63)/t29-,30-,34-,35-,36-,37-,38-,39-,40-,41-/m0/s1
SMILES	CC[C@H](C)[C@H]1C(=O)N2CCC[C@H]2C(=N[C@@H](CC(C)C)C(=N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCC[C@H]2C(=N[C@@H](C(C)C)C(=N[C@@H]([C@@H](C)CC)C(=O)N2CCC[C@H]2C(=N1)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
NPO40317	Reniochalina stalagmitis	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25490132]
NPO40317	Reniochalina stalagmitis	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	13

Activity Type	# Activity
Cell line	10
Non-molecular	1
Others	2

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT389	Cell line	RPMI-8226	Homo sapiens	IC50	=	4900.0	nM	PMID[25490132]
NPT3140	Cell line	MGC-803	Homo sapiens	IC50	=	9700.0	nM	PMID[25490132]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	20000.0	nM	PMID[25490132]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	17300.0	nM	PMID[25490132]
NPT3140	Cell line	MGC-803	Homo sapiens	IC50	=	9700.0	nM	PMID[29220182]
NPT389	Cell line	RPMI-8226	Homo sapiens	IC50	=	4900.0	nM	PMID[29220182]
NPT389	Cell line	RPMI-8226	Homo sapiens	IC50	=	4500.0	nM	PMID[29220182]
NPT466	Cell line	U-937	Homo sapiens	IC50	=	12400.0	nM	PMID[29220182]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	16900.0	nM	PMID[29220182]
NPT81	Cell line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[29220182]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[25490132]
NPT2	Others	Unspecified	n.a.	IC50	>	11200.0	nM	PMID[29220182]
NPT2	Others	Unspecified	n.a.	IC50	>	20000.0	nM	PMID[29220182]

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 NPC489625 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	31252
0.1-0.2	16841
0.2-0.3	1285
0.3-0.4	371
0.4-0.5	68
0.5-0.6	28
0.6-0.7	8
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	Natural Product ID
0.7204	Intermediate Similarity	NPC223791
0.7143	Intermediate Similarity	NPC17059
0.6702	Remote Similarity	NPC107077
0.6633	Remote Similarity	NPC54420
0.6596	Remote Similarity	NPC293917
0.6337	Remote Similarity	NPC162860
0.6263	Remote Similarity	NPC31385
0.617	Remote Similarity	NPC213629
0.6139	Remote Similarity	NPC110602
0.6139	Remote Similarity	NPC479071
0.5904	Remote Similarity	NPC200589
0.5865	Remote Similarity	NPC479075
0.5794	Remote Similarity	NPC479076
0.5789	Remote Similarity	NPC325976
0.5789	Remote Similarity	NPC326363
0.5783	Remote Similarity	NPC228835
0.5758	Remote Similarity	NPC171317
0.5755	Remote Similarity	NPC479065
0.5701	Remote Similarity	NPC479073
0.5688	Remote Similarity	NPC75726
0.5652	Remote Similarity	NPC489592
0.5596	Remote Similarity	NPC479066
0.5566	Remote Similarity	NPC284549
0.5536	Remote Similarity	NPC100321
0.5514	Remote Similarity	NPC482001
0.547	Remote Similarity	NPC479574
0.5444	Remote Similarity	NPC485876
0.5431	Remote Similarity	NPC69843
0.5421	Remote Similarity	NPC155143
0.5392	Remote Similarity	NPC483341
0.5366	Remote Similarity	NPC49954
0.5366	Remote Similarity	NPC11126
0.5339	Remote Similarity	NPC489555
0.5294	Remote Similarity	NPC486282
0.5229	Remote Similarity	NPC54744
0.5152	Remote Similarity	NPC484874
0.5109	Remote Similarity	NPC91179
0.5043	Remote Similarity	NPC480300

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC489625 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4439
0.1-0.2	4442
0.2-0.3	212
0.3-0.4	45
0.4-0.5	10
0.5-0.6	1
0.6-0.7	1
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
0.6596	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5044	Remote Similarity	NPD7711	Discontinued

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