NPASS Compound

Natural Product: NPC37592

Natural Product ID	NPC37592
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BSCUNSVAACYEAI-ZUSAUGBTSA-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:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

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 62 64 0 0 0 0 0 0 0 0999 V2000 3.9163 1.4417 -1.4354 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2527 0.0193 -0.9883 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3708 -0.4633 0.1003 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8754 -0.1953 1.4907 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3951 -0.3627 1.5685 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9306 0.5834 0.5128 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3161 0.5821 0.6475 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6039 0.0229 -0.6953 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6806 -1.6722 1.1881 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3462 -1.1010 2.4095 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1012 0.0731 -0.0885 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1264 -0.9053 -0.2470 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3984 -0.8711 -1.5447 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3976 0.3772 -1.7210 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5747 0.9945 -0.3584 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8083 0.0166 0.7107 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0635 -0.7700 0.7364 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2717 -0.2854 0.6569 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9279 0.3133 -0.3132 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1954 -0.5286 -0.7160 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6965 -1.0777 0.6022 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7262 0.0417 1.6185 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5094 1.3865 1.0225 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4651 1.5208 0.1566 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9047 -0.2236 2.7209 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9187 -1.7083 0.4514 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7811 -1.4974 -1.5971 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2966 -0.8603 0.8539 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5412 1.9648 -0.4142 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2615 1.3208 -2.5291 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2753 -0.9528 -2.6307 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6487 1.8079 -2.5508 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1144 2.1903 -0.6520 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8526 1.5389 -1.6971 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1263 -0.6191 -1.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2382 -1.5856 0.0579 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6711 0.8574 1.7533 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7277 -0.1164 2.5791 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5483 1.6131 0.6657 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5655 0.9767 1.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4564 -1.6595 0.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6505 -0.8556 3.3116 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5953 -1.9337 -0.1959 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2266 -1.7866 -1.5984 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3517 0.0910 -2.1980 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3774 1.5881 -0.0998 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7839 0.5957 1.6903 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9445 -1.6939 0.0469 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0129 -1.3451 1.7557 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4632 0.4794 -1.3009 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9298 0.1485 -1.1572 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9384 -1.8183 0.9471 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7757 0.0360 2.0396 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4851 1.7566 0.5926 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3193 2.0962 1.8813 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4729 0.6080 3.0697 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5096 -1.5460 1.2143 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5717 -2.0376 -1.8421 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4767 2.5795 -1.1597 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5591 0.9197 -3.3857 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6493 -1.8467 -2.7258 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1164 1.7775 -3.3904 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 0 6 8 1 0 5 9 1 0 4 10 1 0 3 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 22 25 1 0 21 26 1 0 20 27 1 0 16 28 1 0 15 29 1 0 14 30 1 0 13 31 1 0 1 32 1 0 8 2 1 0 28 12 1 0 24 19 1 0 1 33 1 0 1 34 1 0 2 35 1 6 3 36 1 6 4 37 1 1 5 38 1 1 6 39 1 1 7 40 1 0 9 41 1 0 10 42 1 0 12 43 1 1 13 44 1 1 14 45 1 6 15 46 1 1 16 47 1 1 17 48 1 0 17 49 1 0 19 50 1 6 20 51 1 6 21 52 1 1 22 53 1 1 23 54 1 0 23 55 1 0 25 56 1 0 26 57 1 0 27 58 1 0 29 59 1 0 30 60 1 0 31 61 1 0 32 62 1 0 M END

Standard InCHIKey	BSCUNSVAACYEAI-ZUSAUGBTSA-N
Standard InCHI	InChI=1S/C17H30O15/c18-1-5-14(10(23)11(24)15(27)30-5)32-17-13(26)9(22)8(21)6(31-17)3-29-16-12(25)7(20)4(19)2-28-16/h4-27H,1-3H2/t4-,5+,6+,7+,8-,9+,10-,11+,12-,13+,14-,15-,16-,17+/m0/s1
SMILES	C([C@@H]1[C@@H]([C@H]([C@H]([C@@H](O)O1)O)O)O[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](CO[C@H]2[C@H]([C@@H]([C@H](CO2)O)O)O)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	474.16	Volume:	408.772 ? Van der Waals volume.
Dense:	1.16	LogP:	-3.291 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-2.561 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	0.019 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	18.0
TPSA:	248.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	10.0	Rings:	3.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.172	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.859	Fsp³:	1.0
MCE-18:	66.294 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.344	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.044 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.503	Promiscuous compounds:	0.013

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.04	MDCK Permeability:	-4.944
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
PAMPA:	1.0 ? 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):	0.991
20% Bioavailability (F20%):	0.939	30% Bioavailability (F30%):	0.954
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.466
Plasma Protein Binding (PPB):	22.841%	Volume Distribution (VD):	-0.541
Fu:	83.215% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.094
OATP1B3 inhibitor:	0.05	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.978
HLM stability:	0.002 ? 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):

0.937

Half-life (T1/2):

2.572

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.048
Human Hepatotoxicity (H-HT):	0.562	Drug-induced Liver Injury (DILI):	0.832
AMES Toxicity:	0.991	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	1.0
Carcinogencity:	0.051	Eye Corrosion:	0.0
Eye Irritation:	0.357	Respiratory Toxicity:	0.025
Drug-induced Neurotoxicity:	0.018	Ototoxicity:	0.989
Hematotoxicity:	0.814	Drug-induced Nephrotoxicity:	0.905
Genotoxicity:	0.228	RPMI-8226 Immunitoxicity:	0.259
A549 Cytotoxicity:	0.781	Hek293 Cytotoxicity:	0.141
BCF:	0.043 ? 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:	1.417 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.057 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.214 ? 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
NPO3762	Amentotaxus argotaenia	Species	Taxaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[32633512]
NPO822	Cressa cretica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11832	Pinus banksiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9311	Parkia clappertoniana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9051	Delesseria sanguinea	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11832	Pinus banksiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12895	Polypodiodes niponica	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10177	Eria linearifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9051	Delesseria sanguinea	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10588	Diploschistes violarius	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9311	Parkia clappertoniana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5205	Gymnoascus reesii	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3762	Amentotaxus argotaenia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO822	Cressa cretica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	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 NPC37592 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	34857
0.1-0.2	11981
0.2-0.3	2711
0.3-0.4	277
0.4-0.5	16
0.5-0.6	10
0.6-0.7	6
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
0.6667	Remote Similarity	NPC303727
0.6327	Remote Similarity	NPC246558
0.6327	Remote Similarity	NPC67660
0.6327	Remote Similarity	NPC165198
0.6327	Remote Similarity	NPC209753
0.6327	Remote Similarity	NPC58629
0.5849	Remote Similarity	NPC317023
0.5849	Remote Similarity	NPC489878
0.5536	Remote Similarity	NPC472025
0.537	Remote Similarity	NPC89145
0.537	Remote Similarity	NPC157514
0.537	Remote Similarity	NPC322314
0.537	Remote Similarity	NPC269166
0.5254	Remote Similarity	NPC474078
0.5106	Remote Similarity	NPC323574
0.5094	Remote Similarity	NPC145112

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC37592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8196
0.1-0.2	856
0.2-0.3	78
0.3-0.4	12
0.4-0.5	2
0.5-0.6	1
0.6-0.7	5
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
0.6327	Remote Similarity	NPD888	Phase 3
0.6327	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD891	Phase 3
0.6327	Remote Similarity	NPD892	Phase 3
0.6327	Remote Similarity	NPD893	Approved
0.5263	Remote Similarity	NPD3181	Phase 3

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