NPASS Compound

Natural Product: NPC17140

Natural Product ID	NPC17140
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XHEKEYHCIIMZRR-WJTVCTBASA-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:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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 38 39 0 0 0 0 0 0 0 0999 V2000 2.3680 2.3771 -0.0134 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9104 1.0046 -0.1548 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2545 0.7925 -0.2383 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7188 -0.5175 -0.3708 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8370 -1.5673 -0.4155 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4647 -1.3079 -0.3267 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9735 -0.0429 -0.1967 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6460 0.2066 -0.1109 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4500 -0.6512 -0.1291 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3179 -0.2535 -1.2793 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4215 0.6854 -1.0214 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8225 0.7550 0.4361 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4461 -0.5980 1.0057 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1277 -0.8507 2.3228 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7784 -2.0503 2.8827 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0652 -0.5787 1.1076 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1775 1.0218 0.5861 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1331 1.9667 -1.5101 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8257 -1.4198 -1.8522 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0874 -0.7173 -0.4544 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1703 2.8404 -1.0079 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4219 2.3832 0.5606 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1054 3.0203 0.4979 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9519 1.6138 -0.2037 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1954 -2.5746 -0.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8057 -2.1768 -0.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0930 -1.6909 -0.2339 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6779 0.1995 -2.0962 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3523 0.3461 -1.5648 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2009 1.5679 0.8869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7152 -1.4114 0.3008 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2244 -0.8387 2.1273 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9374 -0.0230 3.0363 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1408 -2.8193 2.3713 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3721 1.5312 1.3925 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9207 2.5333 -1.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1159 -1.2794 -2.7897 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4055 -1.4764 -1.0561 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 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 13 16 1 0 12 17 1 0 11 18 1 0 10 19 1 0 4 20 1 0 7 2 1 0 16 9 1 0 1 21 1 0 1 22 1 0 1 23 1 0 3 24 1 0 5 25 1 0 6 26 1 0 9 27 1 6 10 28 1 6 11 29 1 6 12 30 1 1 13 31 1 6 14 32 1 0 14 33 1 0 15 34 1 0 17 35 1 0 18 36 1 0 19 37 1 0 20 38 1 0 M END

Standard InCHIKey	XHEKEYHCIIMZRR-WJTVCTBASA-N
Standard InCHI	InChI=1S/C13H18O7/c1-6-4-7(15)2-3-8(6)19-13-12(18)11(17)10(16)9(5-14)20-13/h2-4,9-18H,5H2,1H3/t9-,10-,11+,12-,13-/m0/s1
SMILES	Cc1cc(ccc1O[C@@H]1[C@H]([C@@H]([C@H]([C@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	286.11	Volume:	269.914 ? Van der Waals volume.
Dense:	1.06	LogP:	-0.284 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.117 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.307 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	12.0
TPSA:	119.61 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	5.0	Rings:	2.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.477	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.463	Fsp³:	0.538
MCE-18:	49.0 ? 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:	0.53	Fluc inhibitor:	0.017 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.177 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.07 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.243	Promiscuous compounds:	0.107

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.422	MDCK Permeability:	-5.128
Pgp-inhibitor:	0.0	Pgp-substrate:	0.191
PAMPA:	0.991 ? 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):	0.554
20% Bioavailability (F20%):	0.488	30% Bioavailability (F30%):	0.91
50% Bioavailability (F50%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.605	MRP1:	0.128
Plasma Protein Binding (PPB):	67.425%	Volume Distribution (VD):	-0.215
Fu:	33.119% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.049
BSEP inhibitor:	0.01

ADMET: Metabolism

CYP1A2-inhibitor:	0.022	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.005	CYP2D6-substrate:	0.025
CYP3A4-inhibitor:	0.418	CYP3A4-substrate:	0.962
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.841
HLM stability:	0.325 ? 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):

2.441

Half-life (T1/2):

2.299

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.277
Human Hepatotoxicity (H-HT):	0.498	Drug-induced Liver Injury (DILI):	0.416
AMES Toxicity:	0.721	Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.023	Skin Sensitization:	0.974
Carcinogencity:	0.177	Eye Corrosion:	0.008
Eye Irritation:	0.918	Respiratory Toxicity:	0.035
Drug-induced Neurotoxicity:	0.032	Ototoxicity:	0.694
Hematotoxicity:	0.123	Drug-induced Nephrotoxicity:	0.534
Genotoxicity:	0.085	RPMI-8226 Immunitoxicity:	0.099
A549 Cytotoxicity:	0.168	Hek293 Cytotoxicity:	0.127
BCF:	0.401 ? 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:	2.535 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.994 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.152 ? 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
NPO18028	Isodon scoparius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19072209]
NPO22059	Eurythoe complanata	Species	Amphinomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20028030]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23707257]
NPO18028	Isodon scoparius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28654256]
NPO22059	Eurythoe complanata	Species	Amphinomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17103	Phellodendron lavallei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16376	Careya arborea	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18028	Isodon scoparius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15241	Lamium amplexicaule	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15241	Lamium amplexicaule	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15241	Lamium amplexicaule	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14124	Virola minutiflora	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22059	Eurythoe complanata	Species	Amphinomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17103	Phellodendron lavallei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1163	Mantella expectata	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18028	Isodon scoparius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16376	Careya arborea	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15241	Lamium amplexicaule	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17404	Rumex ecklonianus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5670	Chimaphila japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	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 NPC17140 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	17431
0.1-0.2	27120
0.2-0.3	4142
0.3-0.4	708
0.4-0.5	328
0.5-0.6	107
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	Natural Product ID
0.76	Intermediate Similarity	NPC40377
0.7021	Intermediate Similarity	NPC142319
0.6786	Remote Similarity	NPC97326
0.6346	Remote Similarity	NPC12308
0.6275	Remote Similarity	NPC152722
0.6071	Remote Similarity	NPC606892
0.6032	Remote Similarity	NPC92054
0.5962	Remote Similarity	NPC9248
0.5938	Remote Similarity	NPC299435
0.5882	Remote Similarity	NPC217854
0.5882	Remote Similarity	NPC484157
0.5833	Remote Similarity	NPC228907
0.5769	Remote Similarity	NPC192810
0.5763	Remote Similarity	NPC106025
0.5758	Remote Similarity	NPC260604
0.5741	Remote Similarity	NPC226712
0.5741	Remote Similarity	NPC608788
0.5738	Remote Similarity	NPC611586
0.5714	Remote Similarity	NPC310661
0.569	Remote Similarity	NPC26080
0.569	Remote Similarity	NPC165686
0.5686	Remote Similarity	NPC276195
0.5686	Remote Similarity	NPC212729
0.5686	Remote Similarity	NPC604498
0.5636	Remote Similarity	NPC221090
0.5588	Remote Similarity	NPC145319
0.5577	Remote Similarity	NPC269242
0.5574	Remote Similarity	NPC199335
0.5574	Remote Similarity	NPC475628
0.5574	Remote Similarity	NPC477240
0.5556	Remote Similarity	NPC299144
0.5556	Remote Similarity	NPC60589
0.5556	Remote Similarity	NPC469708
0.5538	Remote Similarity	NPC271385
0.5538	Remote Similarity	NPC5029
0.5536	Remote Similarity	NPC166168
0.5536	Remote Similarity	NPC214454
0.5517	Remote Similarity	NPC205054
0.5517	Remote Similarity	NPC23084
0.5517	Remote Similarity	NPC19470
0.55	Remote Similarity	NPC599943
0.5484	Remote Similarity	NPC134260
0.5484	Remote Similarity	NPC190217
0.5472	Remote Similarity	NPC294470
0.5469	Remote Similarity	NPC210192
0.5424	Remote Similarity	NPC214910
0.5424	Remote Similarity	NPC210015
0.5424	Remote Similarity	NPC481303
0.541	Remote Similarity	NPC59324
0.541	Remote Similarity	NPC85799
0.541	Remote Similarity	NPC303422
0.5385	Remote Similarity	NPC177742
0.5385	Remote Similarity	NPC99233
0.5357	Remote Similarity	NPC69513
0.5352	Remote Similarity	NPC474422
0.5345	Remote Similarity	NPC218685
0.5333	Remote Similarity	NPC57751
0.5333	Remote Similarity	NPC105827
0.5323	Remote Similarity	NPC478871
0.5323	Remote Similarity	NPC478870
0.5323	Remote Similarity	NPC478872
0.5323	Remote Similarity	NPC478873
0.5312	Remote Similarity	NPC600107
0.5312	Remote Similarity	NPC604892
0.5303	Remote Similarity	NPC278329
0.5303	Remote Similarity	NPC146837
0.5303	Remote Similarity	NPC601828
0.5273	Remote Similarity	NPC609376
0.5263	Remote Similarity	NPC48863
0.5263	Remote Similarity	NPC251981
0.5263	Remote Similarity	NPC13745
0.5263	Remote Similarity	NPC604209
0.5254	Remote Similarity	NPC83975
0.5238	Remote Similarity	NPC242028
0.5238	Remote Similarity	NPC294166
0.5238	Remote Similarity	NPC203230
0.5238	Remote Similarity	NPC252169
0.5238	Remote Similarity	NPC115022
0.5238	Remote Similarity	NPC469661
0.5238	Remote Similarity	NPC65530
0.5231	Remote Similarity	NPC302989
0.5224	Remote Similarity	NPC169248
0.5224	Remote Similarity	NPC72649
0.5217	Remote Similarity	NPC257963
0.5185	Remote Similarity	NPC153149
0.5179	Remote Similarity	NPC200092
0.5172	Remote Similarity	NPC215833
0.5172	Remote Similarity	NPC9912
0.5167	Remote Similarity	NPC164599
0.5167	Remote Similarity	NPC210478
0.5161	Remote Similarity	NPC218003
0.5156	Remote Similarity	NPC111536
0.5156	Remote Similarity	NPC8497
0.5156	Remote Similarity	NPC185778
0.5156	Remote Similarity	NPC604095
0.5156	Remote Similarity	NPC610808
0.5147	Remote Similarity	NPC328093
0.5147	Remote Similarity	NPC259182
0.5147	Remote Similarity	NPC88484
0.5147	Remote Similarity	NPC76128
0.5143	Remote Similarity	NPC22324
0.5091	Remote Similarity	NPC25817
0.5088	Remote Similarity	NPC80098
0.5088	Remote Similarity	NPC145900
0.5085	Remote Similarity	NPC49074
0.5082	Remote Similarity	NPC609351
0.5079	Remote Similarity	NPC100389
0.5077	Remote Similarity	NPC260681
0.5077	Remote Similarity	NPC121001
0.5075	Remote Similarity	NPC148273
0.5075	Remote Similarity	NPC30432
0.5075	Remote Similarity	NPC606849
0.5072	Remote Similarity	NPC471457
0.507	Remote Similarity	NPC287294

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC17140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4630
0.1-0.2	4346
0.2-0.3	150
0.3-0.4	19
0.4-0.5	4
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	Drug ID	Developmental Stage
0.5741	Remote Similarity	NPD1091	Pre-clinical

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