NPASS Compound

Natural Product: NPC57690

Natural Product ID	NPC57690
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Chaetoglobosin A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL472850
PubChem CID	6438437
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001821] Cytochalasans [CHEMONTID:0003767] Chaetoglobosins

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 75 80 0 0 0 0 0 0 0 0999 V2000 -6.4328 1.0322 -1.3093 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9809 0.5673 -1.0443 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0187 1.6116 -1.5086 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6043 1.2552 -1.2369 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6729 1.0658 -2.1679 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2918 0.7242 -2.2054 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6364 1.7445 -2.7841 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0272 1.5302 -4.1522 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9485 1.1729 -3.0068 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1613 2.0254 -3.1514 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0239 -0.2882 -2.7799 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5299 -0.6567 -1.3878 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3725 0.1368 -0.9407 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9980 1.2145 -0.1318 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1965 0.9064 0.1532 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6151 -0.3512 -0.3627 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8063 -1.4145 0.6582 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8819 -0.9880 1.5898 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2155 -1.3877 1.5183 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9079 -0.7919 2.4889 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1115 0.0026 3.2297 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8391 -0.1217 2.6644 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8146 0.5915 3.2418 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0704 1.4011 4.3492 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3241 1.5227 4.9032 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3459 0.8080 4.3244 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4128 2.4221 0.2922 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6762 -0.5603 -0.2802 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5661 -1.0870 -1.0217 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9461 -0.7619 1.1673 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1773 -1.1283 1.3801 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0102 -1.4672 2.4873 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5841 -1.6563 3.5721 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4898 -1.5379 2.1546 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6640 -1.2408 0.6829 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8115 0.0543 0.2917 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6142 -2.3504 -0.2981 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1615 -2.5984 2.5656 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4436 -0.8248 -2.8984 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3666 1.6593 -2.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8196 1.5882 -0.4419 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0730 0.1660 -1.5569 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8825 -0.2731 -1.8312 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1760 1.8804 -2.5820 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2645 2.5488 -0.9123 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4078 1.2184 -0.1542 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1319 1.2260 -3.2023 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2570 -0.2262 -2.8928 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5348 2.8111 -2.4875 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8455 1.9892 -2.2870 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8310 3.0934 -3.2285 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7547 1.8222 -4.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4432 -0.9106 -3.4907 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4016 -1.7574 -1.3819 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5883 -0.1427 -0.8928 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1712 -2.3568 0.1679 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8819 -1.6237 1.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6042 -2.0812 0.7734 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9284 -0.9255 2.6493 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8312 0.4985 2.8272 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2178 1.9446 4.7664 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4655 2.1727 5.7712 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3550 0.8730 4.7284 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5260 2.7221 1.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1301 -0.5847 1.7728 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7963 -1.2448 0.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9580 -0.6319 2.7183 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7928 0.7721 1.1416 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6798 -2.6702 -0.4533 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2309 -2.0895 -1.2821 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0820 -3.2396 0.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6217 -3.3628 2.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5753 -1.2695 -3.9273 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2121 -0.0634 -2.8086 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5226 -1.6887 -2.2147 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 2 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 14 27 1 0 13 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 34 38 1 0 11 39 1 0 36 2 1 0 13 6 1 0 22 18 1 0 9 7 1 0 16 12 1 0 26 21 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 6 3 44 1 0 3 45 1 0 4 46 1 0 5 47 1 0 6 48 1 6 7 49 1 6 10 50 1 0 10 51 1 0 10 52 1 0 11 53 1 6 12 54 1 6 16 55 1 6 17 56 1 0 17 57 1 0 19 58 1 0 20 59 1 0 23 60 1 0 24 61 1 0 25 62 1 0 26 63 1 0 27 64 1 0 30 65 1 0 31 66 1 0 34 67 1 1 36 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 38 72 1 0 39 73 1 0 39 74 1 0 39 75 1 0 M END

Standard InCHIKey	OUMWCYMRLMEZJH-VOXRAUTJSA-N
Standard InCHI	InChI=1S/C32H36N2O5/c1-17-8-7-10-22-29-31(4,39-29)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(38)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-14,16-17,19,22,24,27-29,33,37H,8,15H2,1-4H3,(H,34,38)/b10-7+,13-12+,18-14+/t17-,19-,22-,24-,27-,28+,29-,31+,32+/m0/s1
SMILES	C[C@H]1C/C=C/[C@H]2[C@@H]3O[C@]3(C)[C@H]([C@@H]3[C@]2(C(=N[C@H]3Cc2c[nH]c3c2cccc3)O)C(=O)/C=C/C(=O)[C@@H](/C(=C/1)/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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25717	Maytenus hookeri	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
IZ	3
IC50	3

Activity Type	# Activity
Cell line	3
Organism	4

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	=	3.2	ug.mL-1	PMID[15497948]
NPT168	Cell line	P388	Mus musculus	IC50	=	1.94	ug.mL-1	PMID[15497948]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	6300.0	nM	PMID[27759375]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	3.0	mm	PMID[15497948]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	IZ	=	5.0	mm	PMID[15497948]
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	83.4	%	PMID[19246197]
NPT2526	Organism	Rhizomucor miehei	Rhizomucor miehei	IZ	=	25.0	mm	PMID[19246197]

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
-	Rattus norvegicus	LD50	>	400.0	mg/kg	ToxVal
-	Mus musculus	LD50	>	400.0	mg/kg	ToxVal

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 NPC57690 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	12026
0.1-0.2	36143
0.2-0.3	1481
0.3-0.4	169
0.4-0.5	11
0.5-0.6	11
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
0.7526	Intermediate Similarity	NPC225821
0.7475	Intermediate Similarity	NPC267926
0.7449	Intermediate Similarity	NPC141428
0.7449	Intermediate Similarity	NPC203614
0.7423	Intermediate Similarity	NPC266192
0.7374	Intermediate Similarity	NPC487663
0.7374	Intermediate Similarity	NPC487657
0.7273	Intermediate Similarity	NPC87856
0.7228	Intermediate Similarity	NPC487658
0.7059	Intermediate Similarity	NPC487660
0.6762	Remote Similarity	NPC487659
0.6571	Remote Similarity	NPC290529
0.6408	Remote Similarity	NPC98715
0.6286	Remote Similarity	NPC46225
0.6226	Remote Similarity	NPC204491
0.6111	Remote Similarity	NPC235885
0.6075	Remote Similarity	NPC151976
0.5981	Remote Similarity	NPC258062
0.5963	Remote Similarity	NPC2395
0.5962	Remote Similarity	NPC195239
0.5922	Remote Similarity	NPC157828
0.5833	Remote Similarity	NPC487664
0.5648	Remote Similarity	NPC487662
0.5607	Remote Similarity	NPC267965
0.5556	Remote Similarity	NPC271862
0.5455	Remote Similarity	NPC487661
0.5455	Remote Similarity	NPC132211
0.513	Remote Similarity	NPC70155

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC57690 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3568
0.1-0.2	5381
0.2-0.3	175
0.3-0.4	26
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