NPASS Compound

Natural Product: NPC472023

Natural Product ID	NPC472023
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CKUVNOCSBYYHIS-KRGTZXDDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3326514
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 106110 0 0 0 0 0 0 0 0999 V2000 -9.7776 1.4546 0.9070 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7039 0.2136 0.1008 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5327 -0.3241 -0.1643 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2286 0.2362 0.2985 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3701 0.5647 -0.8835 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0211 1.1470 -0.5092 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2680 2.3997 0.2630 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2132 0.1057 0.1041 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0440 -1.0262 -0.9168 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5954 -1.4918 -0.7818 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2282 -0.9756 0.5608 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8767 0.3924 0.6449 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0714 1.4734 0.0295 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6478 1.4118 0.6216 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0919 0.0937 0.1281 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7705 -0.9766 0.8954 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1874 -2.3174 0.5246 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3285 -2.2534 0.7761 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8729 -1.3115 -0.2526 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3983 0.0731 0.0803 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7811 0.8947 -1.1606 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2369 0.8983 -1.4520 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0306 -0.2768 -1.0530 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3358 -1.4429 -0.4810 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0633 -1.8394 0.8169 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4914 -2.6922 -1.3735 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0606 0.1876 -0.1993 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3196 0.0623 -0.7062 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0266 1.3754 -0.9369 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5219 1.2029 -0.7587 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8713 0.6567 0.5878 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8024 -0.2914 1.0448 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0329 -0.8248 0.0586 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0190 0.3663 2.1560 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8812 0.8854 3.1206 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1152 -0.0008 0.4584 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0791 2.4917 -0.9246 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8727 1.8053 -2.2769 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0698 0.7143 1.2406 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6630 -0.8398 2.3952 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8690 1.3504 -1.3364 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9457 -1.8407 1.5916 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4445 1.5059 -1.7566 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9570 -0.3973 -0.3913 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1444 2.2660 0.4592 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8030 1.8729 0.9456 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3840 1.2765 1.9374 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4998 -1.2289 -0.7537 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8111 -0.4790 1.0083 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4954 1.1444 0.8970 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.2640 -1.5397 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2051 -0.3494 -1.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1713 2.2729 1.3599 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3031 2.7733 0.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6366 3.2637 -0.1047 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8092 -0.3700 0.9404 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1976 -0.6509 -1.9493 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7434 -1.8442 -0.7606 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5475 -2.6115 -0.8272 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0201 -1.1132 -1.6200 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9477 0.6198 1.7341 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4213 2.4675 0.3559 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0834 2.2724 0.2416 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6993 1.4783 1.7137 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4426 -0.0146 -0.9423 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3183 -2.5479 -0.5548 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5470 -3.1568 1.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7022 -3.2784 0.5671 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4515 -1.9339 1.8106 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3563 -1.5788 -1.2232 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3844 1.9083 -1.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2534 0.3751 -2.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3222 1.0974 -2.5673 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6364 1.8690 -1.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5972 -0.6385 -1.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9184 -2.5374 0.5716 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4147 -2.3878 1.4976 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5534 -0.9508 1.2644 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4601 -2.5939 -1.8968 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3826 -3.6123 -0.7917 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7050 -2.6998 -2.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2327 -0.4050 -1.7318 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6399 2.1918 -0.3187 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8748 0.5774 -1.6032 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0463 1.4982 1.2741 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3430 -1.1569 1.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3832 -0.3873 2.7079 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3525 1.1604 1.8287 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9612 1.8629 2.9774 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9881 -0.8243 -0.0934 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4298 3.1169 -0.4734 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4229 1.0781 -2.7858 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4964 0.0454 1.9846 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8874 1.4242 0.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3373 1.3838 1.7775 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8571 -1.8669 2.8240 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4305 -0.1838 2.8343 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3098 -0.5410 2.7660 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7149 2.2017 -1.7881 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1873 -1.2904 2.5025 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4023 -2.7604 1.8432 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9349 -2.1940 1.1754 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9790 2.1928 -2.2074 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8488 0.0275 0.1022 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0698 -0.1327 -1.4819 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9626 -1.5021 -0.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 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 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 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 0 24 26 1 0 23 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 20 39 1 0 16 40 1 0 13 41 1 0 11 42 1 0 6 43 1 0 2 44 1 0 12 8 1 0 16 11 1 0 20 15 1 0 24 19 1 0 33 28 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 5 51 1 0 5 52 1 0 7 53 1 0 7 54 1 0 7 55 1 0 8 56 1 0 9 57 1 0 9 58 1 0 10 59 1 0 10 60 1 0 12 61 1 0 13 62 1 0 14 63 1 0 14 64 1 0 15 65 1 0 17 66 1 0 17 67 1 0 18 68 1 0 18 69 1 0 19 70 1 0 21 71 1 0 21 72 1 0 22 73 1 0 22 74 1 0 23 75 1 0 25 76 1 0 25 77 1 0 25 78 1 0 26 79 1 0 26 80 1 0 26 81 1 0 28 82 1 0 29 83 1 0 30 84 1 0 31 85 1 0 32 86 1 0 34 87 1 0 34 88 1 0 35 89 1 0 36 90 1 0 37 91 1 0 38 92 1 0 39 93 1 0 39 94 1 0 39 95 1 0 40 96 1 0 40 97 1 0 40 98 1 0 41 99 1 0 42100 1 0 42101 1 0 42102 1 0 43103 1 0 44104 1 0 44105 1 0 44106 1 0 M END

Standard InCHIKey	CKUVNOCSBYYHIS-KRGTZXDDSA-N
Standard InCHI	InChI=1S/C36H62O8/c1-20(2)10-9-14-36(8,42)21-11-16-35(7)27(21)22(38)18-25-33(5)15-13-26(32(3,4)24(33)12-17-34(25,35)6)44-31-30(41)29(40)28(39)23(19-37)43-31/h10,21-31,37-42H,9,11-19H2,1-8H3/t21-,22+,23+,24-,25+,26-,27-,28+,29-,30+,31-,33-,34+,35+,36?/m0/s1
SMILES	CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)C)C)O)C)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
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	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	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT41	Individual protein	Aldose reductase	Homo sapiens	IC50	>	200000.0	nM	PMID[19651906]

In vitro activity

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

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 NPC472023 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	19444
0.1-0.2	24318
0.2-0.3	4714
0.3-0.4	1143
0.4-0.5	180
0.5-0.6	33
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC88000
1.0	High Similarity	NPC4831
0.863	High Similarity	NPC8039
0.863	High Similarity	NPC120123
0.7342	Intermediate Similarity	NPC165033
0.7342	Intermediate Similarity	NPC273879
0.7317	Intermediate Similarity	NPC194842
0.7297	Intermediate Similarity	NPC234287
0.7294	Intermediate Similarity	NPC472988
0.7294	Intermediate Similarity	NPC38217
0.7105	Intermediate Similarity	NPC31907
0.7027	Intermediate Similarity	NPC280825
0.68	Remote Similarity	NPC473198
0.6795	Remote Similarity	NPC47566
0.6795	Remote Similarity	NPC129372
0.6579	Remote Similarity	NPC607273
0.6386	Remote Similarity	NPC312553
0.6353	Remote Similarity	NPC69737
0.6265	Remote Similarity	NPC472897
0.6265	Remote Similarity	NPC472896
0.6235	Remote Similarity	NPC208477
0.6235	Remote Similarity	NPC473020
0.6145	Remote Similarity	NPC159036
0.6092	Remote Similarity	NPC472252
0.6092	Remote Similarity	NPC245280
0.5857	Remote Similarity	NPC80530
0.5857	Remote Similarity	NPC273410
0.5833	Remote Similarity	NPC157659
0.5765	Remote Similarity	NPC611039
0.5732	Remote Similarity	NPC473200
0.5714	Remote Similarity	NPC16520
0.5714	Remote Similarity	NPC211879
0.5714	Remote Similarity	NPC189852
0.5714	Remote Similarity	NPC155010
0.5699	Remote Similarity	NPC208650
0.5604	Remote Similarity	NPC231340
0.5579	Remote Similarity	NPC220427
0.5568	Remote Similarity	NPC472987
0.5488	Remote Similarity	NPC140446
0.5488	Remote Similarity	NPC66654
0.5455	Remote Similarity	NPC90583
0.5455	Remote Similarity	NPC477927
0.5408	Remote Similarity	NPC14946
0.5408	Remote Similarity	NPC63368
0.5393	Remote Similarity	NPC16573
0.5333	Remote Similarity	NPC473199
0.5275	Remote Similarity	NPC181467
0.5263	Remote Similarity	NPC234160
0.5263	Remote Similarity	NPC286969
0.5253	Remote Similarity	NPC159005
0.5248	Remote Similarity	NPC135369
0.5233	Remote Similarity	NPC470312
0.5161	Remote Similarity	NPC269627
0.5135	Remote Similarity	NPC207013
0.5094	Remote Similarity	NPC488292
0.5065	Remote Similarity	NPC488508
0.5057	Remote Similarity	NPC473844
0.5048	Remote Similarity	NPC241381

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472023 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7294
0.1-0.2	1776
0.2-0.3	67
0.3-0.4	12
0.4-0.5	1
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