NPASS Compound

Natural Product: NPC479184

Natural Product ID	NPC479184
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PRSNJXPAQBUJBL-DXKHDLERSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101676777
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

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 135141 0 0 0 0 0 0 0 0999 V2000 10.7179 1.6259 0.4173 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6580 0.6353 0.9541 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5921 0.8656 2.4252 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6820 0.0146 3.2102 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2337 0.0442 2.9069 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9084 -0.3988 1.5604 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0707 0.1661 0.8039 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2421 1.2976 0.9767 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4576 2.3538 -0.0284 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4552 3.6963 0.3618 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6834 4.7221 -0.5353 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9272 4.4443 -1.8722 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9288 3.1200 -2.2481 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6998 2.0942 -1.3546 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8229 0.8726 1.1734 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2517 0.0402 0.1208 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9736 -0.6580 -0.6214 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8764 -0.0450 -0.1330 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3415 -0.8675 -1.1862 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8548 -2.1776 -0.5937 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5460 -2.6009 -0.9963 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4304 -2.1155 0.0057 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9200 -2.0796 0.0192 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7135 -1.0106 -0.5509 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6977 -1.1861 -1.6546 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6764 -0.5195 0.5664 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0105 -1.6305 1.5099 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8456 -3.0365 1.1242 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6111 -3.3968 0.3306 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5903 -3.9964 -0.5354 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6991 -3.6828 0.2865 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6550 -4.1672 1.0223 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8310 -5.4180 1.5344 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9355 -5.9700 1.3975 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6919 -6.0689 2.2363 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6894 0.2210 0.1047 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8022 1.5479 0.4295 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0847 2.4728 -0.6955 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2058 3.4160 -0.3830 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4863 2.6380 -0.0674 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0819 1.3918 0.7195 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8600 1.6124 1.3323 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3982 3.4209 0.6062 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4284 4.3017 -1.4294 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9600 3.1229 -1.1927 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8127 0.0865 -0.9919 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7651 0.9888 -0.2180 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9433 0.2611 -2.2482 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8559 -0.6883 -2.2264 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3058 -0.0929 -1.8638 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4223 1.3592 -2.1739 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7128 -2.1465 -2.4311 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5004 -2.4035 -3.2888 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8257 -2.8506 -3.1073 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7352 -0.0719 -3.3805 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1897 0.7913 -4.3335 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8922 2.0127 -4.2138 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0239 0.3195 -5.5011 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0111 -0.9008 0.6388 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6030 -0.8126 1.9615 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6115 -1.9214 2.6130 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1859 0.3835 2.6447 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2335 0.3074 3.9557 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6167 1.4198 4.6742 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5857 2.6584 4.0734 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1781 2.7631 2.7817 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2052 1.6218 2.0762 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5377 -4.0089 -1.0524 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9546 1.9403 1.3847 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5751 -1.5575 1.0570 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7437 1.2632 0.6570 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5826 1.6464 -0.6770 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5316 2.6389 0.8123 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7189 0.8346 0.4169 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9895 -0.3935 0.7726 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6440 0.7009 2.8123 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4182 1.9647 2.6612 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0865 -1.0401 3.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7904 0.3133 4.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6742 -0.6313 3.6183 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7921 1.0590 3.1071 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5066 1.8132 1.9709 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2710 3.9439 1.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6738 5.7451 -0.2151 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1107 5.2562 -2.5912 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1200 2.8380 -3.2912 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7222 1.0852 -1.7008 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7658 0.2442 2.1346 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2379 -1.1588 -1.7626 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9892 -2.0925 0.5017 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5862 -3.0300 -0.8137 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2118 -2.8841 0.8548 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9631 -1.7549 1.1634 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9825 -0.1083 -1.9350 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7098 -1.5308 -1.3603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3164 -1.5794 -2.6048 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0150 0.1845 1.1389 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4652 -1.4707 2.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0906 -1.5501 1.8640 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8098 -3.6603 2.0793 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7346 -3.6817 -1.5906 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -5.1073 -0.5877 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3155 -6.9384 1.6646 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9863 -6.3137 3.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8203 -5.3826 2.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9446 1.8997 1.0782 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4497 1.8596 -1.5770 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9427 4.0088 0.5103 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9117 2.3028 -1.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0429 0.4871 0.1255 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8382 1.2678 1.5177 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5013 3.0988 1.5432 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7918 5.1493 -1.0212 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2571 3.8816 -1.7222 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7579 1.3089 -2.2956 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5294 1.5317 -2.3145 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0270 1.6300 -3.1758 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1388 2.0329 -1.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2663 -3.0401 -2.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9177 -1.4598 -3.7233 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2582 -2.9894 -4.2340 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5004 -3.7878 -3.6255 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5323 -3.1930 -2.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3969 -2.2754 -3.8519 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8614 -0.2859 -5.1165 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3337 1.1488 -6.1329 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3726 -0.3666 -6.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2820 -0.6450 4.4899 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9512 1.3613 5.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 3.5528 4.6311 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1532 3.7335 2.3119 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5066 1.7829 1.0706 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2889 -4.3623 -0.6692 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1906 2.6748 0.7703 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0655 -2.1009 0.3842 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 1 0 5 6 1 0 6 7 2 3 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 8 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 1 32 33 1 0 33 34 2 0 33 35 1 0 26 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 38 45 1 0 24 46 1 0 46 47 2 0 46 48 1 0 48 49 1 0 49 50 2 0 50 51 1 0 49 52 1 0 52 53 1 0 52 54 1 0 48 55 1 0 55 56 1 0 56 57 2 0 56 58 1 0 22 59 1 0 59 60 1 0 60 61 2 0 60 62 1 0 62 63 2 0 63 64 1 0 64 65 2 0 65 66 1 0 66 67 2 0 21 68 1 6 15 69 1 0 6 70 1 0 14 9 1 0 50 19 1 0 67 62 1 0 52 21 1 0 29 23 1 0 42 37 1 0 31 28 1 0 1 71 1 0 1 72 1 0 1 73 1 0 2 74 1 0 2 75 1 0 3 76 1 0 3 77 1 0 4 78 1 0 4 79 1 0 5 80 1 0 5 81 1 0 8 82 1 1 10 83 1 0 11 84 1 0 12 85 1 0 13 86 1 0 14 87 1 0 15 88 1 1 19 89 1 6 20 90 1 0 20 91 1 0 22 92 1 1 23 93 1 1 25 94 1 0 25 95 1 0 25 96 1 0 26 97 1 1 27 98 1 0 27 99 1 0 28100 1 1 30101 1 0 30102 1 0 35103 1 0 35104 1 0 35105 1 0 37106 1 1 38107 1 6 39108 1 1 40109 1 6 41110 1 0 41111 1 0 43112 1 0 44113 1 0 45114 1 0 48115 1 6 51116 1 0 51117 1 0 51118 1 0 53119 1 0 53120 1 0 53121 1 0 54122 1 0 54123 1 0 54124 1 0 58125 1 0 58126 1 0 58127 1 0 63128 1 0 64129 1 0 65130 1 0 66131 1 0 67132 1 0 68133 1 0 69134 1 0 70135 1 0 M END

Standard InCHIKey	PRSNJXPAQBUJBL-DXKHDLERSA-N
Standard InCHI	InChI=1S/C51H65NO18/c1-8-9-12-21-35(56)52-37(29-17-13-10-14-18-29)39(58)46(62)67-32-23-51(63)44(69-45(61)30-19-15-11-16-20-30)42-49(7,43(60)41(66-27(3)53)36(26(32)2)48(51,5)6)33(22-34-50(42,25-65-34)70-28(4)54)68-47-40(59)38(57)31(55)24-64-47/h10-11,13-20,31-34,37-42,44,47,55,57-59,63H,8-9,12,21-25H2,1-7H3,(H,52,56)/t31-,32+,33+,34-,37+,38+,39-,40-,41-,42+,44+,47+,49-,50+,51-/m1/s1
SMILES	CCCCCC(=N[C@@H](c1ccccc1)[C@H](C(=O)O[C@H]1C[C@]2([C@H]([C@H]3[C@@](C)([C@H](C[C@@H]4[C@]3(CO4)OC(=O)C)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C)OC(=O)c1ccccc1)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
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	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
Cell line	1
Others	1

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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	1.5	nM	PMID[28240909]
NPT2	Others	Unspecified	n.a.	IC50	=	94100.0	nM	PMID[28240909]

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 NPC479184 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	11987
0.1-0.2	34723
0.2-0.3	3063
0.3-0.4	27
0.4-0.5	13
0.5-0.6	16
0.6-0.7	17
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8807	High Similarity	NPC472391
0.8727	High Similarity	NPC479185
0.8482	Intermediate Similarity	NPC472375
0.8455	Intermediate Similarity	NPC116862
0.7568	Intermediate Similarity	NPC471629
0.7568	Intermediate Similarity	NPC306001
0.7521	Intermediate Similarity	NPC479173
0.7373	Intermediate Similarity	NPC479186
0.7321	Intermediate Similarity	NPC324251
0.7321	Intermediate Similarity	NPC206211
0.713	Intermediate Similarity	NPC275170
0.7119	Intermediate Similarity	NPC289383
0.6724	Remote Similarity	NPC33372
0.6724	Remote Similarity	NPC67246
0.6667	Remote Similarity	NPC487360
0.6667	Remote Similarity	NPC479182
0.6667	Remote Similarity	NPC479180
0.6667	Remote Similarity	NPC471493
0.6581	Remote Similarity	NPC471754
0.65	Remote Similarity	NPC486061
0.65	Remote Similarity	NPC486060
0.6496	Remote Similarity	NPC208553
0.6496	Remote Similarity	NPC181964
0.6496	Remote Similarity	NPC307628
0.6446	Remote Similarity	NPC487361
0.6356	Remote Similarity	NPC471623
0.6134	Remote Similarity	NPC473490
0.6111	Remote Similarity	NPC472392
0.6	Remote Similarity	NPC478328
0.595	Remote Similarity	NPC453583
0.5868	Remote Similarity	NPC327699
0.5854	Remote Similarity	NPC478329
0.5772	Remote Similarity	NPC479183
0.5772	Remote Similarity	NPC479181
0.561	Remote Similarity	NPC321072
0.561	Remote Similarity	NPC215892
0.561	Remote Similarity	NPC242662
0.5565	Remote Similarity	NPC191193
0.5484	Remote Similarity	NPC102167
0.5484	Remote Similarity	NPC488127
0.544	Remote Similarity	NPC453588
0.544	Remote Similarity	NPC473400
0.5403	Remote Similarity	NPC36607
0.5378	Remote Similarity	NPC603140
0.5197	Remote Similarity	NPC603171

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479184 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3878
0.1-0.2	5147
0.2-0.3	112
0.3-0.4	0
0.4-0.5	6
0.5-0.6	4
0.6-0.7	3
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
0.693	Remote Similarity	NPD8435	Phase 4
0.6496	Remote Similarity	NPD8485	Phase 4
0.6134	Remote Similarity	NPD8424	Phase 3
0.5887	Remote Similarity	NPD8486	Phase 1
0.5484	Remote Similarity	NPD8360	Approved
0.5484	Remote Similarity	NPD8361	Phase 4
0.5145	Remote Similarity	NPD8462	Phase 2

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