NPASS Compound

Natural Product: NPC471013

Natural Product ID	NPC471013
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Triptersinin L
IUPAC Name	n.a.
Synonyms	Triptersinin L
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2335701
PubChem CID	71716430
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids 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 2D 90 94 0 0 0 0 0 0 0 0999 V2000 -8.1749 1.0666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6786 1.1712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8398 -0.0724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3434 0.0323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0406 -0.8001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6859 1.3805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1895 1.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3463 -0.0067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0039 -1.3549 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5002 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3129 -0.7279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1578 -2.8077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8192 2.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0328 2.9769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2463 3.8586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0895 5.3503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0289 6.4111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3030 6.2320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6624 3.5870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7079 4.1971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9214 3.3154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7646 1.8236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1275 0.3682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2610 1.9283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1588 3.4824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9976 4.7259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5093 6.1442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4939 4.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2888 3.3492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7442 3.7121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8489 5.2084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4581 5.7703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6933 -1.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2158 -2.5838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3442 2.2172 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2294 3.2209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1971 2.7574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5413 4.6881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5734 5.6918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2615 7.1591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1650 7.6226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2798 6.6189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9679 5.1517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4974 -1.4206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2796 2.5629 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6385 2.4931 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6713 0.9619 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0210 2.5194 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1934 2.5997 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8454 0.0456 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6521 -2.6771 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8096 -3.4653 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8154 -4.1559 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1293 -1.7730 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5177 0.9588 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0068 4.4767 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3810 2.3195 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4213 7.4455 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4521 5.2679 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4000 7.2550 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2000 4.9873 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9059 5.0998 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1949 5.6067 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3633 2.9020 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7384 4.5734 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6163 0.5510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8031 -0.3361 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6651 -1.0322 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2451 0.7962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7269 1.9584 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0925 3.0546 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2753 7.2592 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1073 -3.3443 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5961 -0.7656 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9924 -2.7135 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0699 -3.3564 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6503 -2.1453 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8259 -3.9542 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0698 5.5873 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3763 8.1628 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4769 9.0898 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4234 4.7889 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8455 -0.7630 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3483 -2.3848 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3143 -2.6785 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 8 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 16 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 6 22 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 15 36 1 6 36 37 1 0 37 38 1 0 37 39 1 0 14 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 3 49 1 0 16 7 1 0 35 31 2 0 48 43 1 0 37 13 1 0 25 15 1 0 1 50 1 0 1 51 1 0 1 52 1 0 2 53 1 0 7 54 1 1 8 55 1 6 12 56 1 0 12 57 1 0 12 58 1 0 13 59 1 1 14 60 1 6 17 61 1 0 17 62 1 0 21 63 1 0 21 64 1 0 21 65 1 0 22 66 1 6 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 26 71 1 0 26 72 1 0 26 73 1 0 27 74 1 0 32 75 1 0 33 76 1 0 35 77 1 0 38 78 1 0 38 79 1 0 38 80 1 0 39 81 1 0 39 82 1 0 39 83 1 0 44 84 1 0 45 85 1 0 46 86 1 0 48 87 1 0 49 88 1 0 49 89 1 0 49 90 1 0 M END

Standard InCHIKey	LFXDNVNKLUPWOC-BRZNNSIUSA-N
Standard InCHI	InChI=1S/C35H41NO13/c1-8-19(2)29(39)48-28-26(45-21(4)38)25-27(47-30(40)22-10-9-14-36-16-22)35(49-32(25,5)6)33(7,42)13-11-24(34(28,35)18-44-20(3)37)46-31(41)23-12-15-43-17-23/h8-10,12,14-17,24-28,42H,11,13,18H2,1-7H3/b19-8+/t24-,25+,26+,27+,28-,33-,34-,35-/m0/s1
SMILES	C/C=C(/C(=O)O[C@H]1[C@H](OC(=O)C)[C@@H]2[C@H]([C@]3([C@@]1(COC(=O)C)[C@H](CC[C@]3(C)O)OC(=O)c1ccoc1)OC2(C)C)OC(=O)c1cccnc1)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
IC50	5

Activity Type	# Activity
Cell line	5

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
NPT179	Cell line	A2780	Homo sapiens	IC50	>	1000.0	nM	DrugMatrix in vivo data: Pathology
NPT180	Cell line	HCT-8	Homo sapiens	IC50	>	1000.0	nM	PMID[25993496]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	>	1000.0	nM	PMID[3236010]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	>	1000.0	nM	PMID[15104485]
NPT81	Cell line	A549	Homo sapiens	IC50	>	1000.0	nM	PMID[20930123]

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 NPC471013 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	13073
0.1-0.2	34268
0.2-0.3	2151
0.3-0.4	274
0.4-0.5	58
0.5-0.6	19
0.6-0.7	7
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
0.8395	Intermediate Similarity	NPC148896
0.7952	Intermediate Similarity	NPC10904
0.7654	Intermediate Similarity	NPC294803
0.7529	Intermediate Similarity	NPC180668
0.7229	Intermediate Similarity	NPC481062
0.7229	Intermediate Similarity	NPC481058
0.7229	Intermediate Similarity	NPC481060
0.6824	Remote Similarity	NPC481064
0.6737	Remote Similarity	NPC6981
0.6591	Remote Similarity	NPC488899
0.6404	Remote Similarity	NPC488900
0.6333	Remote Similarity	NPC610927
0.6087	Remote Similarity	NPC301368
0.6087	Remote Similarity	NPC84815
0.5955	Remote Similarity	NPC147340
0.5934	Remote Similarity	NPC6815
0.5909	Remote Similarity	NPC57628
0.5824	Remote Similarity	NPC271460
0.5761	Remote Similarity	NPC479049
0.5638	Remote Similarity	NPC479048
0.5612	Remote Similarity	NPC176413
0.5612	Remote Similarity	NPC483885
0.5612	Remote Similarity	NPC294512
0.5579	Remote Similarity	NPC479041
0.5556	Remote Similarity	NPC481059
0.5495	Remote Similarity	NPC481063
0.5455	Remote Similarity	NPC479045
0.534	Remote Similarity	NPC294579
0.534	Remote Similarity	NPC144779
0.5294	Remote Similarity	NPC488902
0.5294	Remote Similarity	NPC488903
0.5049	Remote Similarity	NPC96801
0.5049	Remote Similarity	NPC150698

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471013 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3957
0.1-0.2	5139
0.2-0.3	53
0.3-0.4	1
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