NPASS Compound

Natural Product: NPC207993

Natural Product ID	NPC207993
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TZTNBBJNIUDTRA-CWXVXMPOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	53231520
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic 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 49 51 0 0 0 0 0 0 0 0999 V2000 5.9379 -0.6889 -0.2994 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4514 -0.5096 -0.3084 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7546 -0.5046 -1.4258 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4466 -0.6802 -2.7172 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3349 -0.3295 -1.3810 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6648 -0.3258 -2.4699 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5996 -0.1583 -0.2254 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1915 0.0126 -0.2194 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0040 1.4648 0.1309 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3339 2.0286 -0.1982 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4855 1.4149 -0.3205 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7934 1.9354 -0.6362 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0715 3.0917 -0.9625 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7673 0.8227 -0.5009 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1413 -0.2857 -0.1499 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8151 -1.5838 0.0815 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7103 -0.0686 -0.1180 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9285 -0.4588 1.0493 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5500 -0.9761 0.5396 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0748 -1.6142 1.7567 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9582 -0.9017 2.5677 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2608 -1.8749 2.6156 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2302 -2.3568 3.7828 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3667 -1.4853 1.8759 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3425 3.4542 -0.3892 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1659 4.0034 -0.2623 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3394 4.3290 -0.6738 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2048 -1.7775 -0.3229 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4171 -0.1404 -1.1523 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3755 -0.2895 0.6294 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9774 -0.3822 0.6773 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1378 0.1629 -2.9386 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7010 -0.7071 -3.5363 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9921 -1.6486 -2.7640 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1026 -0.0300 -1.3169 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7331 2.0361 -0.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3064 1.6960 1.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8110 0.9715 -0.6778 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5270 -1.9913 1.0802 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4163 -2.3357 -0.6560 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9146 -1.5265 -0.0448 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2599 -0.5248 -1.0609 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7534 0.4229 1.7129 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8692 -1.8032 -0.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3539 -2.6447 1.5553 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0926 -1.5159 3.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9302 -0.9033 2.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6253 0.0887 2.9370 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1597 5.0882 -1.3380 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 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 2 0 22 24 1 0 10 25 1 0 25 26 2 0 25 27 1 0 19 8 1 0 17 11 1 0 24 18 1 0 1 28 1 0 1 29 1 0 1 30 1 0 2 31 1 0 4 32 1 0 4 33 1 0 4 34 1 0 8 35 1 6 9 36 1 0 9 37 1 0 14 38 1 0 16 39 1 0 16 40 1 0 16 41 1 0 17 42 1 6 18 43 1 1 19 44 1 6 20 45 1 6 21 46 1 0 21 47 1 0 21 48 1 0 27 49 1 0 M END

Standard InCHIKey	TZTNBBJNIUDTRA-CWXVXMPOSA-N
Standard InCHI	InChI=1S/C20H22O7/c1-5-8(2)19(24)26-13-7-11(18(22)23)16-12(21)6-9(3)14(16)17-15(13)10(4)20(25)27-17/h5-6,10,13-15,17H,7H2,1-4H3,(H,22,23)/b8-5+/t10-,13-,14+,15-,17-/m1/s1
SMILES	C/C=C(C)/C(=O)O[C@@H]1CC(=C2C(=O)C=C(C)[C@@H]2[C@@H]2[C@@H]1[C@@H](C)C(=O)O2)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	374.14	Volume:	371.883 ? Van der Waals volume.
Dense:	1.006	LogP:	1.466 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.618 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.273 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	20.0
TPSA:	106.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.594	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.607	Fsp³:	0.5
MCE-18:	52.8 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.265	Fluc inhibitor:	0.215 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.142 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.385	Promiscuous compounds:	0.478

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.167	MDCK Permeability:	-4.825
Pgp-inhibitor:	0.002	Pgp-substrate:	0.337
PAMPA:	0.989 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.165
20% Bioavailability (F20%):	0.542	30% Bioavailability (F30%):	0.896
50% Bioavailability (F50%):	0.886

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.993
Plasma Protein Binding (PPB):	92.309%	Volume Distribution (VD):	-0.556
Fu:	7.526% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.976
OATP1B3 inhibitor:	0.975	BCRP inhibitor:	0.001
BSEP inhibitor:	0.388

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.026	CYP3A4-substrate:	0.281
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.667
HLM stability:	0.15 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

2.483

Half-life (T1/2):

1.651

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.045
Human Hepatotoxicity (H-HT):	0.662	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.299	Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.262	Skin Sensitization:	0.997
Carcinogencity:	0.439	Eye Corrosion:	0.485
Eye Irritation:	0.794	Respiratory Toxicity:	0.47
Drug-induced Neurotoxicity:	0.514	Ototoxicity:	0.554
Hematotoxicity:	0.807	Drug-induced Nephrotoxicity:	0.917
Genotoxicity:	0.988	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.084	Hek293 Cytotoxicity:	0.129
BCF:	0.327 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	2.959 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.273 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.591 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO22460	Vernonia pachyclada	Species	Asteraceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[16180816]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19388660]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21524573]
NPO12737.1	Torreya fargesii var. yunnanensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25495612]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28362501]
NPO15473	Ocotea heterochroma	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[30188730]
NPO22460	Vernonia pachyclada	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12737.1	Torreya fargesii var. yunnanensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17407	Bauhinia splendens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17875	Erythroxylum microphyllum	Species	Erythroxylaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14133	Eupatorium perfoliatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2709	Flindersia dissosperma	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17949	Gentiana thunbergii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17032	Knautia silvatica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16738	Leptogorgia gilchristi	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26459	Lissoclinum fragile	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15473	Ocotea heterochroma	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17640	Omphalotus nidiformis	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17792	Penicillium lapidosum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29082	Persicaria hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17105	Phaenocoma prolifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20969	Pseudognaphalium affine	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16515	Siphonoglossa mexicana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15971	Teclea boiviniana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17949	Gentiana thunbergii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29082	Persicaria hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20969	Pseudognaphalium affine	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17949	Gentiana thunbergii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12737.1	Torreya fargesii var. yunnanensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17105	Phaenocoma prolifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16738	Leptogorgia gilchristi	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17949	Gentiana thunbergii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22460	Vernonia pachyclada	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2709	Flindersia dissosperma	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17792	Penicillium lapidosum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12737.1	Torreya fargesii var. yunnanensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16515	Siphonoglossa mexicana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17875	Erythroxylum microphyllum	Species	Erythroxylaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29082	Persicaria hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17407	Bauhinia splendens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14133	Eupatorium perfoliatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26459	Lissoclinum fragile	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20969	Pseudognaphalium affine	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17640	Omphalotus nidiformis	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15971	Teclea boiviniana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17032	Knautia silvatica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15473	Ocotea heterochroma	Species	Lauraceae	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
EC50	1

Activity Type	# Activity
Organism	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
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	EC50	=	20700.0	nM	PMID[30234295]

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 NPC207993 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	23924
0.1-0.2	24284
0.2-0.3	1597
0.3-0.4	46
0.4-0.5	6
0.5-0.6	1
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	Natural Product ID
0.5932	Remote Similarity	NPC107787

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC207993 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6087
0.1-0.2	3025
0.2-0.3	38
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