NPASS Compound

Natural Product: NPC221491

Natural Product ID	NPC221491
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BKXIGVQZLPZYLM-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	2737151
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

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 57 57 0 0 0 0 0 0 0 0999 V2000 0.1293 1.9538 0.5721 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3441 1.0408 0.4582 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5704 1.7400 0.9535 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7864 0.8583 0.8823 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0669 0.4333 -0.5147 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3174 -0.4269 -0.6134 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1489 -1.6700 0.2142 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3894 -2.5153 0.0851 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5626 -1.8016 0.5959 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6905 -2.3400 0.3824 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5335 -0.6020 1.2858 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1011 1.2411 0.0768 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0134 0.8192 -1.3528 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2479 0.1101 -1.8431 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4828 0.9366 -1.7492 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7117 0.2528 -2.2161 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1278 -0.9725 -1.4898 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4449 -0.7748 -0.0545 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5259 -0.9139 0.9519 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8587 -0.7162 2.2980 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1400 -0.3710 2.6556 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0754 -0.2275 1.6556 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7455 -0.4222 0.3339 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2635 2.8591 -0.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0063 2.2152 1.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5109 0.7472 -0.6003 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1398 0.1161 1.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8122 2.6466 0.3264 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4237 2.1322 1.9895 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6792 1.3583 1.3158 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5702 -0.0169 1.5459 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2054 -0.1935 -0.8975 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1899 1.2539 -1.2238 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1773 0.1876 -0.3448 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4623 -0.6996 -1.6850 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0048 -1.3514 1.2815 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2426 -2.2061 -0.1536 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2271 -3.4985 0.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5497 -2.6589 -1.0169 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3370 0.0120 1.2316 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9931 1.8313 0.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1858 0.3051 0.7052 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7879 1.7070 -1.9773 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1774 0.1026 -1.4953 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4072 -0.8500 -1.3288 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0570 -0.0536 -2.9499 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3352 1.8311 -2.4122 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6729 1.3170 -0.7144 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5924 0.9558 -2.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5969 -0.0202 -3.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4220 -1.8216 -1.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0753 -1.3316 -1.9885 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5029 -1.1892 0.7157 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1135 -0.8329 3.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4055 -0.2148 3.7141 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0735 0.0422 1.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4677 -0.3138 -0.4667 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 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 1 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 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 18 1 0 1 24 1 0 1 25 1 0 2 26 1 0 2 27 1 0 3 28 1 0 3 29 1 0 4 30 1 0 4 31 1 0 5 32 1 0 5 33 1 0 6 34 1 0 6 35 1 0 7 36 1 0 7 37 1 0 8 38 1 0 8 39 1 0 11 40 1 0 12 41 1 0 12 42 1 0 13 43 1 0 13 44 1 0 14 45 1 0 14 46 1 0 15 47 1 0 15 48 1 0 16 49 1 0 16 50 1 0 17 51 1 0 17 52 1 0 19 53 1 0 20 54 1 0 21 55 1 0 22 56 1 0 23 57 1 0 M END

Standard InCHIKey	BKXIGVQZLPZYLM-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C21H34O2/c22-21(23)19-15-10-8-6-4-2-1-3-5-7-9-12-16-20-17-13-11-14-18-20/h11,13-14,17-18H,1-10,12,15-16,19H2,(H,22,23)
SMILES	C(CCCCCCCC(=O)O)CCCCCCc1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	318.26	Volume:	370.25 ? Van der Waals volume.
Dense:	0.86	LogP:	5.819 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.425 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.231 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	7.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.381	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.707	Fsp³:	0.667
MCE-18:	5.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.444	Fluc inhibitor:	0.32 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.075 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.944	Promiscuous compounds:	0.582

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.119	MDCK Permeability:	-4.791
Pgp-inhibitor:	0.003	Pgp-substrate:	0.005
PAMPA:	0.179 ? 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):	0.456
20% Bioavailability (F20%):	0.498	30% Bioavailability (F30%):	0.939
50% Bioavailability (F50%):	0.514

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041	MRP1:	0.959
Plasma Protein Binding (PPB):	99.534%	Volume Distribution (VD):	0.059
Fu:	0.128% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.627
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.161
BSEP inhibitor:	0.886

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.012
CYP2C19-inhibitor:	0.095	CYP2C19-substrate:	0.355
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.287
CYP2D6-inhibitor:	0.161	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.725
CYP2B6-substrate:	0.998	CYP2C8-inhibitor:	0.602
HLM stability:	0.011 ? 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):

3.406

Half-life (T1/2):

0.954

ADMET: Toxicity

hERG Blockers:	0.383	hERG Blockers (10um):	0.605
Human Hepatotoxicity (H-HT):	0.505	Drug-induced Liver Injury (DILI):	0.191
AMES Toxicity:	0.053	Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.199	Skin Sensitization:	0.95
Carcinogencity:	0.149	Eye Corrosion:	0.892
Eye Irritation:	0.995	Respiratory Toxicity:	0.883
Drug-induced Neurotoxicity:	0.053	Ototoxicity:	0.29
Hematotoxicity:	0.195	Drug-induced Nephrotoxicity:	0.34
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.15	Hek293 Cytotoxicity:	0.1
BCF:	0.824 ? 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:	3.894 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.698 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.045 ? 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
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	bark	Indonesia	n.a.	PMID[15270571]
NPO21076	Nephthea armata	Species	Nephtheidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15387641]
NPO22180	Dracaena mannii	Species	Asparagaceae	Eukaryota	n.a.	stem	n.a.	PMID[18481024]
NPO22180	Dracaena mannii	Species	Asparagaceae	Eukaryota	stems	Yaound, village of Bangoua, near Bangangt	2007-APR	PMID[20553003]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22313254]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38139796]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39147955]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22525	Lobophytum denticulatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29112	Streptomyces luteosporeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17813	Pittosporum undulatum	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22923	Parthenium bipinnatifidum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21076	Nephthea armata	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21819	Domohinea perrieri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22064	Mannia fragrans	Species	Aytoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19330	Cephalaria procera	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20571	Limnodynastes interioris	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22180	Dracaena mannii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18284	Cytisus ciliatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20708	Mesua beccariana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21076	Nephthea armata	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22525	Lobophytum denticulatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22125	Helipterum propinquum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22923	Parthenium bipinnatifidum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19330	Cephalaria procera	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22007	Acer spicatum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21819	Domohinea perrieri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22064	Mannia fragrans	Species	Aytoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17813	Pittosporum undulatum	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22867	Stephanitis rhododendri	Species	Tingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29112	Streptomyces luteosporeus	Species	Streptomycetaceae	Bacteria	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 NPC221491 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	31433
0.1-0.2	16543
0.2-0.3	1556
0.3-0.4	240
0.4-0.5	74
0.5-0.6	8
0.6-0.7	1
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC44830
0.6216	Remote Similarity	NPC599840
0.56	Remote Similarity	NPC94487
0.5556	Remote Similarity	NPC210849
0.55	Remote Similarity	NPC611530
0.5283	Remote Similarity	NPC307915
0.5152	Remote Similarity	NPC214610
0.5152	Remote Similarity	NPC118968
0.5152	Remote Similarity	NPC183424
0.5152	Remote Similarity	NPC294085

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC221491 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3431
0.1-0.2	4987
0.2-0.3	630
0.3-0.4	74
0.4-0.5	23
0.5-0.6	3
0.6-0.7	1
0.7-0.8	1
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
0.725	Intermediate Similarity	NPD4793	Discontinued
0.6216	Remote Similarity	NPD226	Phase 4
0.5476	Remote Similarity	NPD9589	Approved
0.5476	Remote Similarity	NPD9590	Approved
0.5152	Remote Similarity	NPD9655	Phase 4

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