NPASS Compound

Natural Product: NPC488902

Natural Product ID	NPC488902
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RCYFFNPLRZUBBL-JENNFBKLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 3D 89 93 0 0 0 0 0 0 0 0999 V2000 -1.0562 -2.4496 3.7252 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1037 -2.5887 2.5531 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2894 -2.3065 3.0429 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1263 -1.3875 2.2639 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6195 -0.9028 0.9450 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1387 -0.5721 1.0504 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0050 0.3892 2.2079 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7409 1.5769 2.0026 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7815 2.6066 2.8918 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1265 2.5214 3.9638 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5944 3.8096 2.5836 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3917 0.0677 -0.1913 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1608 -0.8377 -1.1063 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0249 -1.8273 -0.4092 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9767 -1.6391 1.1250 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5322 -1.9072 1.3211 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1348 -2.7394 0.2480 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2444 -3.1387 -0.4384 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0160 -4.2860 0.0732 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8946 -3.4040 -1.8939 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8974 -2.4254 1.7695 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0178 -1.9876 2.4538 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2272 -0.7521 2.4980 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9919 -2.8735 3.1396 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9461 -0.0022 -1.9698 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7306 0.1381 -3.3128 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7913 -0.4923 -3.8528 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5525 1.0074 -4.1996 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2161 1.1858 0.0415 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8746 2.4623 -0.3711 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2390 2.5759 -0.9812 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7255 3.6165 -0.1298 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9242 3.4621 0.5309 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7567 4.5555 0.7747 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3601 5.8141 0.3404 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1839 5.9377 -0.3027 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3832 4.8855 -0.5373 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2737 0.3132 0.6444 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0476 0.4126 -0.5492 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0447 -0.6354 -1.1952 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6637 1.6681 -0.7675 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4521 2.0102 -1.7275 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9058 1.1764 -2.7974 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1461 -0.1488 -2.8557 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4625 -0.7998 -4.0361 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5540 -0.1250 -5.2218 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3230 1.2225 -5.2147 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0095 1.8537 -4.0438 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5051 -1.4658 3.8088 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8056 -3.2958 3.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4527 -2.6176 4.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1098 -3.7165 2.3843 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8930 -3.2699 3.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2174 -2.0251 4.1452 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1556 -1.8017 2.0729 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3532 -0.4900 2.9175 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7867 -1.6845 0.1668 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0613 0.7127 2.3350 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3933 -0.0036 3.1658 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7819 3.8959 1.4882 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6121 3.7575 3.0519 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0934 4.7543 2.9120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5152 0.4566 -0.7443 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3969 -1.3005 -1.7960 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0416 -1.9225 -0.7697 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2761 -0.5636 1.2486 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7182 -5.2107 -0.5003 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1120 -4.1608 -0.1749 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9684 -4.5260 1.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1170 -4.4803 -2.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1639 -3.2250 -2.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5072 -2.8136 -2.5896 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6753 -2.9619 4.2168 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9840 -2.3813 3.1629 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0055 -3.8896 2.7411 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3731 0.3541 -4.6012 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9943 1.3763 -5.0593 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0293 1.8065 -3.5974 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2745 2.5211 0.8844 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6852 4.4242 1.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0137 6.6459 0.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4525 5.0260 -1.0531 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4673 2.5108 -0.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8455 3.0923 -1.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1832 -0.7471 -1.9421 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6419 -1.8751 -4.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8000 -0.6246 -6.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3983 1.7596 -6.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8385 2.9190 -4.1032 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 1 1 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 6 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 17 18 1 0 18 19 1 0 18 20 1 0 15 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 13 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 12 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 5 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 41 42 2 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 16 2 1 0 37 32 1 0 48 43 1 0 16 6 1 0 18 14 1 0 1 49 1 0 1 50 1 0 1 51 1 0 2 52 1 6 3 53 1 0 3 54 1 0 4 55 1 0 4 56 1 0 5 57 1 6 7 58 1 0 7 59 1 0 11 60 1 0 11 61 1 0 11 62 1 0 12 63 1 6 13 64 1 6 14 65 1 6 15 66 1 6 19 67 1 0 19 68 1 0 19 69 1 0 20 70 1 0 20 71 1 0 20 72 1 0 24 73 1 0 24 74 1 0 24 75 1 0 28 76 1 0 28 77 1 0 28 78 1 0 33 79 1 0 34 80 1 0 35 81 1 0 37 82 1 0 41 83 1 0 42 84 1 0 44 85 1 0 45 86 1 0 46 87 1 0 47 88 1 0 48 89 1 0 M END

Standard InCHIKey	RCYFFNPLRZUBBL-JENNFBKLSA-N
Standard InCHI	InChI=1S/C36H41NO11/c1-21-14-16-27(46-28(41)17-15-25-11-8-7-9-12-25)35(20-43-22(2)38)32(47-33(42)26-13-10-18-37-19-26)30(44-23(3)39)29-31(45-24(4)40)36(21,35)48-34(29,5)6/h7-13,15,17-19,21,27,29-32H,14,16,20H2,1-6H3/b17-15-/t21-,27+,29-,30-,31-,32-,35+,36-/m1/s1
SMILES	C[C@@H]1CC[C@@H]([C@@]2(COC(=O)C)[C@@H]([C@@H]([C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)C)OC(=O)C)OC(=O)c1cccnc1)OC(=O)/C=Cc1ccccc1

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
Activity	1

Activity Type	# Activity
Cell line	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
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	75.7	%	PMID[29355322]

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 NPC488902 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	13796
0.1-0.2	33432
0.2-0.3	2167
0.3-0.4	313
0.4-0.5	108
0.5-0.6	22
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC488903
0.7667	Intermediate Similarity	NPC6981
0.7381	Intermediate Similarity	NPC488899
0.7176	Intermediate Similarity	NPC488900
0.6867	Remote Similarity	NPC481059
0.6742	Remote Similarity	NPC473115
0.6632	Remote Similarity	NPC294579
0.6632	Remote Similarity	NPC144779
0.6386	Remote Similarity	NPC90257
0.6386	Remote Similarity	NPC69357
0.6146	Remote Similarity	NPC96801
0.6146	Remote Similarity	NPC150698
0.6111	Remote Similarity	NPC212768
0.6111	Remote Similarity	NPC4421
0.6	Remote Similarity	NPC483845
0.5977	Remote Similarity	NPC483844
0.5778	Remote Similarity	NPC483848
0.5543	Remote Similarity	NPC483849
0.5521	Remote Similarity	NPC148896
0.5484	Remote Similarity	NPC483887
0.5484	Remote Similarity	NPC158020
0.5385	Remote Similarity	NPC483880
0.5385	Remote Similarity	NPC156941
0.5361	Remote Similarity	NPC180668
0.5294	Remote Similarity	NPC471013
0.5263	Remote Similarity	NPC488917
0.5263	Remote Similarity	NPC603877
0.5213	Remote Similarity	NPC481050
0.5204	Remote Similarity	NPC75600
0.5204	Remote Similarity	NPC483884
0.5204	Remote Similarity	NPC10904
0.5104	Remote Similarity	NPC608007
0.5102	Remote Similarity	NPC6576
0.5053	Remote Similarity	NPC481062
0.5053	Remote Similarity	NPC481058
0.5053	Remote Similarity	NPC481060
0.5053	Remote Similarity	NPC609221

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488902 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3266
0.1-0.2	5788
0.2-0.3	95
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