NPASS Compound

Natural Product: NPC86143

Natural Product ID	NPC86143
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JPUKWEQWGBDDQB-YSBXYMAXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	72551446
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 52 55 0 0 0 0 0 0 0 0999 V2000 1.2306 2.8255 0.3209 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4961 4.1884 0.1501 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7223 4.5873 -0.3156 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6476 3.6165 -0.5969 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3648 2.2882 -0.4223 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1154 1.8386 0.0529 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8909 0.4105 0.0938 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6918 -0.2210 -0.0380 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7502 -1.6380 0.0307 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2984 -2.3009 -0.0788 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9170 -2.3268 0.2137 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9684 -3.7117 0.2796 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1610 -4.3586 0.4635 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3296 -3.6508 0.5864 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2782 -2.2806 0.5212 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0786 -1.5921 0.3346 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0162 -0.3067 0.2717 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5494 -4.3151 0.7746 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7459 -4.3879 0.1483 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5424 0.2840 -0.2284 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5987 0.6345 0.5713 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4908 1.6513 -0.0222 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3602 0.9574 -1.0939 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2296 -0.0044 -0.3116 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2340 -1.0307 0.2392 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0933 -1.9941 1.0687 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7267 -1.3245 2.1140 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3085 -0.4919 1.0472 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1097 -0.6381 -1.1720 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0792 1.8685 -1.8246 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8456 2.6626 -0.6812 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0390 5.9410 -0.5047 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2828 2.5840 0.7264 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7464 4.9310 0.3806 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6226 3.9498 -0.9709 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1100 1.5562 -0.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1467 -5.4528 0.5083 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1914 -1.7164 0.6167 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0135 -4.7389 -0.0170 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5750 -5.0533 -0.5943 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1817 1.0329 1.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2168 2.0227 0.7406 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6647 0.3364 -1.7043 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7082 0.5541 0.4964 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8915 -1.6014 -0.6332 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8695 -2.4257 0.3994 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4825 -2.8395 1.4524 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6249 -1.0407 1.7828 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2858 0.0198 -1.9166 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8558 1.7963 -2.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7343 2.5003 -1.6656 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7516 6.4050 0.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 12 19 1 0 8 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 24 29 1 0 23 30 1 0 22 31 1 0 3 32 1 0 6 1 1 0 17 7 1 0 28 21 1 0 16 11 1 0 1 33 1 0 2 34 1 0 4 35 1 0 5 36 1 0 13 37 1 0 15 38 1 0 18 39 1 0 19 40 1 0 21 41 1 1 22 42 1 1 23 43 1 6 24 44 1 1 25 45 1 6 26 46 1 0 26 47 1 0 27 48 1 0 29 49 1 0 30 50 1 0 31 51 1 0 32 52 1 0 M END

Standard InCHIKey	JPUKWEQWGBDDQB-YSBXYMAXSA-N
Standard InCHI	InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15-,17+,18-,21-/m0/s1
SMILES	c1cc(ccc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@H]([C@@H]([C@H]([C@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	448.1	Volume:	413.147 ? Van der Waals volume.
Dense:	1.085	LogP:	1.055 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.341 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.527 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	190.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.279	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.884	Fsp³:	0.286
MCE-18:	87.63 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.63	Fluc inhibitor:	0.304 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.864 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.613 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.267	Promiscuous compounds:	0.579

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.408	MDCK Permeability:	-4.979
Pgp-inhibitor:	0.0	Pgp-substrate:	0.481
PAMPA:	0.987 ? 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):	0.333
20% Bioavailability (F20%):	0.529	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.307
Plasma Protein Binding (PPB):	86.348%	Volume Distribution (VD):	-0.006
Fu:	12.946% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.939
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.961
BSEP inhibitor:	0.052

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.167	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.009	CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.048
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.642 ? 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):

2.911

Half-life (T1/2):

2.071

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.19
Human Hepatotoxicity (H-HT):	0.606	Drug-induced Liver Injury (DILI):	0.886
AMES Toxicity:	0.899	Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.249	Skin Sensitization:	0.997
Carcinogencity:	0.342	Eye Corrosion:	0.0
Eye Irritation:	0.941	Respiratory Toxicity:	0.085
Drug-induced Neurotoxicity:	0.015	Ototoxicity:	0.417
Hematotoxicity:	0.07	Drug-induced Nephrotoxicity:	0.179
Genotoxicity:	0.981	RPMI-8226 Immunitoxicity:	0.111
A549 Cytotoxicity:	0.721	Hek293 Cytotoxicity:	0.752
BCF:	0.743 ? 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:	3.272 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.431 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.881 ? 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
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	root	n.a.	n.a.	PMID[2778455]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29300477]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	Database[Article]
NPO24246	Bebryce indica	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23359	Alstonia somersetensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21806	Helenium tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18876	Cynanchum ascyrifolium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24215	Cheiloclinium cognatum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21806	Helenium tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22290	Garcinia linii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22290	Garcinia linii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21806	Helenium tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18876	Cynanchum ascyrifolium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21806	Helenium tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21806	Helenium tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24363	Calophyllum sclerophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22799	Melianthus comosus	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22131	Nepeta citriodora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19978	Sphagnum fallax	Species	Sphagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20350	Gouania obtusifolia	Species	Gobiesocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19513	Venturia inaequalis	Species	Venturiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20939	Oreocereus bruennowii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8917	Millettia sericea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23830	Helenium hoopesii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23498	Sigmatanthus trifoliatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23408	Anisochilus harmandii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23002	Popowia pisocarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18876	Cynanchum ascyrifolium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23652	Pycnanthemum incanum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21248	Delphinus phocoena	Species	Delphinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24246	Bebryce indica	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22581	Cortinarius claricolor	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22425	Strychnos macrophylla	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22290	Garcinia linii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23359	Alstonia somersetensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21572	Poiretia latifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24215	Cheiloclinium cognatum	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

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

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 NPC86143 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	22667
0.1-0.2	23289
0.2-0.3	2489
0.3-0.4	831
0.4-0.5	250
0.5-0.6	23
0.6-0.7	106
0.7-0.8	0
0.8-0.85	14
0.85-0.9	9
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC77672
1.0	High Similarity	NPC133671
1.0	High Similarity	NPC135391
1.0	High Similarity	NPC78263
1.0	High Similarity	NPC250069
0.8971	High Similarity	NPC145038
0.8971	High Similarity	NPC56077
0.8971	High Similarity	NPC281131
0.8971	High Similarity	NPC253662
0.8971	High Similarity	NPC179950
0.8971	High Similarity	NPC88789
0.8971	High Similarity	NPC491374
0.8939	High Similarity	NPC288084
0.8696	High Similarity	NPC64305
0.8451	Intermediate Similarity	NPC472459
0.8406	Intermediate Similarity	NPC111929
0.8406	Intermediate Similarity	NPC320283
0.8406	Intermediate Similarity	NPC41121
0.8286	Intermediate Similarity	NPC19388
0.8286	Intermediate Similarity	NPC240431
0.8286	Intermediate Similarity	NPC55786
0.8243	Intermediate Similarity	NPC203050
0.8243	Intermediate Similarity	NPC225434
0.8158	Intermediate Similarity	NPC139320
0.8082	Intermediate Similarity	NPC60735
0.8082	Intermediate Similarity	NPC26230
0.8	Intermediate Similarity	NPC67037
0.8	Intermediate Similarity	NPC255615
0.7973	Intermediate Similarity	NPC120099
0.7945	Intermediate Similarity	NPC325555
0.7945	Intermediate Similarity	NPC226304
0.7917	Intermediate Similarity	NPC297987
0.7808	Intermediate Similarity	NPC488080
0.7808	Intermediate Similarity	NPC169977
0.7763	Intermediate Similarity	NPC170052
0.7763	Intermediate Similarity	NPC135846
0.7671	Intermediate Similarity	NPC8573
0.7534	Intermediate Similarity	NPC127546
0.7534	Intermediate Similarity	NPC57625
0.7534	Intermediate Similarity	NPC173637
0.7534	Intermediate Similarity	NPC317489
0.7534	Intermediate Similarity	NPC223424
0.7534	Intermediate Similarity	NPC600591
0.75	Intermediate Similarity	NPC156869
0.75	Intermediate Similarity	NPC609478
0.7468	Intermediate Similarity	NPC29958
0.7465	Intermediate Similarity	NPC54802
0.7465	Intermediate Similarity	NPC197304
0.7403	Intermediate Similarity	NPC116458
0.7403	Intermediate Similarity	NPC246943
0.7375	Intermediate Similarity	NPC470405
0.7375	Intermediate Similarity	NPC471748
0.7361	Intermediate Similarity	NPC34531
0.7333	Intermediate Similarity	NPC24043
0.725	Intermediate Similarity	NPC471079
0.716	Intermediate Similarity	NPC173582
0.716	Intermediate Similarity	NPC265885
0.716	Intermediate Similarity	NPC181465
0.716	Intermediate Similarity	NPC215710
0.716	Intermediate Similarity	NPC163242
0.716	Intermediate Similarity	NPC272068
0.716	Intermediate Similarity	NPC473438
0.716	Intermediate Similarity	NPC253788
0.7159	Intermediate Similarity	NPC189564
0.7143	Intermediate Similarity	NPC159579
0.7143	Intermediate Similarity	NPC175107
0.7051	Intermediate Similarity	NPC224530
0.7013	Intermediate Similarity	NPC42773
0.7013	Intermediate Similarity	NPC45522
0.7	Intermediate Similarity	NPC254855
0.7	Intermediate Similarity	NPC94610
0.6988	Remote Similarity	NPC129264
0.6974	Remote Similarity	NPC136042
0.6962	Remote Similarity	NPC223747
0.6933	Remote Similarity	NPC135599
0.6933	Remote Similarity	NPC73855
0.6933	Remote Similarity	NPC113968
0.6933	Remote Similarity	NPC328940
0.6933	Remote Similarity	NPC277174
0.6933	Remote Similarity	NPC606877
0.6905	Remote Similarity	NPC470125
0.6867	Remote Similarity	NPC304741
0.6854	Remote Similarity	NPC203145
0.6842	Remote Similarity	NPC289667
0.6795	Remote Similarity	NPC599850
0.679	Remote Similarity	NPC116864
0.679	Remote Similarity	NPC244776
0.6782	Remote Similarity	NPC76831
0.6753	Remote Similarity	NPC265530
0.6744	Remote Similarity	NPC270448
0.6709	Remote Similarity	NPC219904
0.6705	Remote Similarity	NPC292929
0.6667	Remote Similarity	NPC276222
0.6667	Remote Similarity	NPC476215
0.6667	Remote Similarity	NPC274618
0.6667	Remote Similarity	NPC118284
0.6667	Remote Similarity	NPC605592
0.6667	Remote Similarity	NPC608147
0.663	Remote Similarity	NPC470712
0.6629	Remote Similarity	NPC602448
0.6625	Remote Similarity	NPC101026
0.6625	Remote Similarity	NPC488077
0.6625	Remote Similarity	NPC197285
0.6625	Remote Similarity	NPC601710
0.6623	Remote Similarity	NPC249281
0.6623	Remote Similarity	NPC143851
0.6591	Remote Similarity	NPC85751
0.6591	Remote Similarity	NPC19240
0.6582	Remote Similarity	NPC21100
0.6575	Remote Similarity	NPC78697
0.6548	Remote Similarity	NPC67326
0.6543	Remote Similarity	NPC605784
0.6522	Remote Similarity	NPC219043
0.6522	Remote Similarity	NPC292019
0.6522	Remote Similarity	NPC202908
0.6512	Remote Similarity	NPC64425
0.65	Remote Similarity	NPC191306
0.65	Remote Similarity	NPC129217
0.65	Remote Similarity	NPC488071
0.6471	Remote Similarity	NPC203259
0.6471	Remote Similarity	NPC33054
0.6471	Remote Similarity	NPC155877
0.6471	Remote Similarity	NPC176740
0.6471	Remote Similarity	NPC471725
0.6471	Remote Similarity	NPC134532
0.6471	Remote Similarity	NPC602582
0.6456	Remote Similarity	NPC46420
0.6456	Remote Similarity	NPC84362
0.642	Remote Similarity	NPC85707
0.6375	Remote Similarity	NPC216496
0.6374	Remote Similarity	NPC214621
0.6374	Remote Similarity	NPC34267
0.6341	Remote Similarity	NPC206123
0.6322	Remote Similarity	NPC61904
0.6322	Remote Similarity	NPC296018
0.6322	Remote Similarity	NPC153755
0.6316	Remote Similarity	NPC470718
0.6296	Remote Similarity	NPC168584
0.6292	Remote Similarity	NPC205824
0.6269	Remote Similarity	NPC103342
0.6207	Remote Similarity	NPC255157
0.6207	Remote Similarity	NPC259896
0.618	Remote Similarity	NPC37668
0.618	Remote Similarity	NPC104883
0.618	Remote Similarity	NPC35119
0.618	Remote Similarity	NPC488679
0.617	Remote Similarity	NPC48984
0.6145	Remote Similarity	NPC88023
0.6145	Remote Similarity	NPC309025
0.6125	Remote Similarity	NPC323593
0.6125	Remote Similarity	NPC203500
0.6122	Remote Similarity	NPC470713
0.6098	Remote Similarity	NPC235260
0.6098	Remote Similarity	NPC155763
0.6098	Remote Similarity	NPC48093
0.6087	Remote Similarity	NPC223426
0.6076	Remote Similarity	NPC476771
0.6071	Remote Similarity	NPC488072
0.6071	Remote Similarity	NPC276377
0.6067	Remote Similarity	NPC12013
0.6067	Remote Similarity	NPC11432
0.6067	Remote Similarity	NPC477613
0.6049	Remote Similarity	NPC52550
0.6047	Remote Similarity	NPC609888
0.6044	Remote Similarity	NPC476472
0.6044	Remote Similarity	NPC294815
0.6044	Remote Similarity	NPC16194
0.6044	Remote Similarity	NPC220173
0.6024	Remote Similarity	NPC259957
0.6	Remote Similarity	NPC39360
0.6	Remote Similarity	NPC104677
0.6	Remote Similarity	NPC95866
0.6	Remote Similarity	NPC29763
0.6	Remote Similarity	NPC32641
0.6	Remote Similarity	NPC83283
0.6	Remote Similarity	NPC256188
0.6	Remote Similarity	NPC210003
0.5979	Remote Similarity	NPC279473
0.5977	Remote Similarity	NPC39834
0.5955	Remote Similarity	NPC488073
0.593	Remote Similarity	NPC251417
0.5926	Remote Similarity	NPC282987
0.5909	Remote Similarity	NPC150164
0.5904	Remote Similarity	NPC182121
0.5889	Remote Similarity	NPC297503
0.5882	Remote Similarity	NPC192539
0.5882	Remote Similarity	NPC66087
0.587	Remote Similarity	NPC471669
0.5862	Remote Similarity	NPC480466
0.5854	Remote Similarity	NPC305811
0.5854	Remote Similarity	NPC84265
0.5851	Remote Similarity	NPC81042
0.5824	Remote Similarity	NPC473327
0.5806	Remote Similarity	NPC221342
0.5806	Remote Similarity	NPC476470
0.5802	Remote Similarity	NPC112755
0.5802	Remote Similarity	NPC170675
0.5802	Remote Similarity	NPC254306
0.5778	Remote Similarity	NPC253521
0.5778	Remote Similarity	NPC154741

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC86143 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5738
0.1-0.2	3328
0.2-0.3	70
0.3-0.4	6
0.4-0.5	6
0.5-0.6	1
0.6-0.7	1
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
0.6471	Remote Similarity	NPD6797	Phase 2
0.5104	Remote Similarity	NPD7804	Clinical (unspecified phase)

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