NPASS Compound

Natural Product: NPC475601

Natural Product ID	NPC475601
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CBYCPANLHVYVDK-HGTSFGFTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL509041
PubChem CID	10557173
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

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 98102 0 0 0 0 0 0 0 0999 V2000 -6.4033 1.2325 0.6862 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1883 0.5866 1.1986 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1494 0.2276 2.4006 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0755 0.3547 0.4094 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9403 -0.2868 1.0302 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8174 -0.4494 0.0261 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4782 0.9405 -0.4447 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7615 1.7015 0.6586 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4207 0.8643 0.9544 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0428 -0.3552 1.7553 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6701 -1.1974 0.6791 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1480 -2.5465 0.9523 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7857 -3.1751 -0.4158 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6230 -2.4904 -1.4238 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7005 -3.0059 -2.5065 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3520 -1.2248 -1.1572 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7290 -1.4412 -0.9660 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7498 -1.0968 -1.7893 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5026 -0.5261 -2.8469 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1464 -1.4055 -1.4185 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6493 -2.6337 -0.5194 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4569 -1.3670 -0.1350 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1409 -2.5449 -1.9222 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3308 -1.8962 -2.0478 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6253 -2.0735 -1.7878 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9257 -3.2041 -1.2442 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7769 -1.1915 -2.0306 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1519 -0.0578 -1.3962 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4548 0.5724 -0.2677 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6609 2.0701 -0.2184 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7786 2.6594 0.9078 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4570 2.0766 0.5922 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0580 2.1762 -0.5933 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5978 1.4088 1.4687 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6702 4.1553 0.6860 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2616 2.4325 2.1503 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3278 0.5546 -1.8592 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0868 0.0686 -2.8914 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6972 -1.0496 -3.4991 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5886 -1.6549 -3.0859 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4780 -3.5911 0.2379 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6548 -3.1977 2.0536 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3864 -3.8867 3.0055 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6165 -3.9354 2.8735 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6261 -4.5181 4.1193 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2883 -0.9649 2.2242 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7325 -0.0933 2.8722 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2932 2.9570 0.1934 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7369 4.0905 0.8604 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5221 4.0302 1.8389 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2808 5.4345 0.4203 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5606 1.5833 -0.9879 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7048 2.0669 -2.2569 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7074 1.8848 -2.9953 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9380 2.7381 -2.6835 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2255 0.4887 0.7027 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6641 2.1031 1.3109 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2164 1.6232 -0.3343 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7100 0.3660 1.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3691 -1.1951 1.4287 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6990 0.8268 -1.2361 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4319 1.7974 1.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7212 0.4047 -0.0881 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2639 -2.6829 0.9742 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8504 -4.2510 -0.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2608 -0.6402 -2.0936 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2366 -1.6395 -0.3368 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8635 -0.6082 -1.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4142 -2.3528 -1.9582 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4164 -2.0120 -2.5981 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2031 -3.6135 -2.3050 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3902 0.2790 -0.3207 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8347 0.1707 0.6959 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6876 2.2594 0.1386 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4633 2.6130 -1.1220 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6390 4.4380 1.0395 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7790 4.3855 -0.3768 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3598 4.7017 1.3476 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1955 3.1589 2.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6567 1.4825 -1.3598 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9957 0.6126 -3.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2286 -2.5962 -3.5466 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8670 -4.4216 -0.4401 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8622 -4.2652 0.9449 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3250 -3.2293 0.7992 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2914 -5.1783 4.7062 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1462 -3.7374 4.7420 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2101 -5.1101 3.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0051 -0.9297 1.4014 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1692 -1.9142 2.7305 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6592 -0.2398 3.0053 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5471 0.8014 3.2335 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4415 5.8817 1.1226 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1401 6.1501 0.3460 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2441 5.3888 -0.5652 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5675 2.1556 -3.3850 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7345 3.7173 -3.1941 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5819 3.0056 -1.8144 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 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 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 13 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 31 35 1 0 31 36 1 0 28 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 21 41 1 0 12 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 10 46 1 0 10 47 1 0 8 48 1 0 48 49 1 0 49 50 2 0 49 51 1 0 7 52 1 0 52 53 1 0 53 54 2 0 53 55 1 0 11 6 1 0 16 6 1 0 34 9 1 0 22 11 1 0 40 27 1 0 1 56 1 0 1 57 1 0 1 58 1 0 5 59 1 0 5 60 1 0 7 61 1 0 8 62 1 0 9 63 1 0 12 64 1 0 13 65 1 0 16 66 1 0 20 67 1 0 20 68 1 0 20 69 1 0 23 70 1 0 23 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 35 76 1 0 35 77 1 0 35 78 1 0 36 79 1 0 37 80 1 0 38 81 1 0 40 82 1 0 41 83 1 0 41 84 1 0 41 85 1 0 45 86 1 0 45 87 1 0 45 88 1 0 46 89 1 0 46 90 1 0 46 91 1 0 47 92 1 0 51 93 1 0 51 94 1 0 51 95 1 0 55 96 1 0 55 97 1 0 55 98 1 0 M END

Standard InCHIKey	CBYCPANLHVYVDK-HGTSFGFTSA-N
Standard InCHI	InChI=1S/C36H43NO18/c1-16(38)48-15-35-27(52-19(4)41)24(43)23-26(51-18(3)40)36(35)34(8,47)28(25(50-17(2)39)29(35)53-20(5)42)54-31(45)32(6,46)11-9-21-10-12-37-13-22(21)30(44)49-14-33(23,7)55-36/h10,12-13,23,25-29,46-47H,9,11,14-15H2,1-8H3/t23-,25+,26-,27-,28+,29+,32?,33+,34+,35-,36+/m1/s1
SMILES	CC(=O)OCC12C(C(C3C(C14C(C(C(=O)C2OC(=O)C)C(O4)(COC(=O)C5=C(CCC(C(=O)O3)(C)O)C=CN=C5)C)OC(=O)C)(C)O)OC(=O)C)OC(=O)C

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
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	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
Inhibition	6

Activity Type	# Activity
Cell line	6

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
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	10.0	%	DOI[10.6019/CHEMBL1201861]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	18.0	%	DOI[10.6019/CHEMBL1201861]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	64.0	%	DOI[10.6019/CHEMBL1201861]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	47.0	%	PMID[17609121]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	77.0	%	PMID[17609121]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	62.0	%	PMID[17609121]

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 NPC475601 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	17470
0.1-0.2	31235
0.2-0.3	1016
0.3-0.4	67
0.4-0.5	40
0.5-0.6	23
0.6-0.7	7
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
0.6768	Remote Similarity	NPC471016
0.6509	Remote Similarity	NPC600224
0.6355	Remote Similarity	NPC604935
0.633	Remote Similarity	NPC253482
0.6238	Remote Similarity	NPC470306
0.6176	Remote Similarity	NPC35208
0.6036	Remote Similarity	NPC475648
0.5946	Remote Similarity	NPC600607
0.5804	Remote Similarity	NPC611166
0.5794	Remote Similarity	NPC146824
0.5766	Remote Similarity	NPC483895
0.5682	Remote Similarity	NPC483852
0.5614	Remote Similarity	NPC601643
0.5586	Remote Similarity	NPC475533
0.5536	Remote Similarity	NPC475315
0.5505	Remote Similarity	NPC473833
0.5505	Remote Similarity	NPC483892
0.5487	Remote Similarity	NPC324619
0.5417	Remote Similarity	NPC469748
0.5398	Remote Similarity	NPC328154
0.5278	Remote Similarity	NPC475408
0.5278	Remote Similarity	NPC250807
0.5278	Remote Similarity	NPC57797
0.5217	Remote Similarity	NPC13603
0.5128	Remote Similarity	NPC473689
0.5128	Remote Similarity	NPC292416
0.5091	Remote Similarity	NPC471014
0.5091	Remote Similarity	NPC76565
0.5091	Remote Similarity	NPC601313
0.5083	Remote Similarity	NPC471979

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475601 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4498
0.1-0.2	4633
0.2-0.3	19
0.3-0.4	0
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