NPASS Compound

Natural Product: NPC294123

Natural Product ID	NPC294123
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FDCJZTPSXKQIGE-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5482939
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

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 43 45 0 0 0 0 0 0 0 0999 V2000 -3.1052 -1.9391 -2.7034 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4393 -2.4715 -1.4306 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5344 -3.0533 -0.5695 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8132 -1.3645 -0.6677 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1326 -1.0634 0.5083 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7957 -0.5677 -1.2393 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2391 0.4592 -0.4837 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0424 1.6085 -0.3852 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1645 1.6417 -0.9636 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5587 2.6551 0.3472 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3524 3.7952 0.4473 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8900 4.8472 1.1716 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3371 4.7929 1.7959 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1002 3.6562 1.6811 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6716 2.5475 0.9488 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4007 1.4832 0.8488 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9742 0.4246 0.1401 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8248 -0.7364 0.0602 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6283 -1.7990 -0.7527 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4862 -2.9144 -0.7477 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5635 -2.9528 0.0958 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7633 -1.8800 0.9159 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9269 -0.7986 0.9082 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8680 -1.9143 1.7832 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4379 -4.0324 0.1360 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7856 5.8873 2.5323 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5796 3.7858 -0.2061 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4904 -0.9173 -2.4187 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3731 -1.7905 -3.5085 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9410 -2.6021 -2.9503 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6546 -3.2022 -1.6758 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9397 -2.2357 0.0467 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0646 -3.8292 0.0718 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3694 -3.4655 -1.1740 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4975 5.7421 1.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0694 3.5849 2.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8359 -1.8731 -1.4715 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3234 -3.7612 -1.3994 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1089 0.0282 1.5637 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6649 -2.2726 2.7183 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4043 -3.8350 0.3623 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3802 6.1772 3.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5783 4.1550 -1.1640 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 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 22 24 1 0 21 25 1 0 13 26 1 0 11 27 1 0 17 7 2 0 23 18 1 0 15 10 1 0 1 28 1 0 1 29 1 0 1 30 1 0 2 31 1 0 3 32 1 0 3 33 1 0 3 34 1 0 12 35 1 0 14 36 1 0 19 37 1 0 20 38 1 0 23 39 1 0 24 40 1 0 25 41 1 0 26 42 1 0 27 43 1 0 M END

Standard InCHIKey	FDCJZTPSXKQIGE-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C19H16O8/c1-8(2)19(25)27-18-16(24)15-13(23)6-10(20)7-14(15)26-17(18)9-3-4-11(21)12(22)5-9/h3-8,20-23H,1-2H3
SMILES	CC(C)C(=O)Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	372.08	Volume:	358.104 ? Van der Waals volume.
Dense:	1.039	LogP:	2.715 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.393 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.378 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	19.0
TPSA:	137.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.407	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.673	Fsp³:	0.158
MCE-18:	21.0 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.632	Fluc inhibitor:	0.234 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.991 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.699 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.379	Promiscuous compounds:	0.466

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.268	MDCK Permeability:	-4.839
Pgp-inhibitor:	0.178	Pgp-substrate:	0.001
PAMPA:	0.087 ? 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):	0.021
20% Bioavailability (F20%):	0.748	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.858
Plasma Protein Binding (PPB):	96.782%	Volume Distribution (VD):	-0.231
Fu:	3.052% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.971
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.495
BSEP inhibitor:	0.984

ADMET: Metabolism

CYP1A2-inhibitor:	0.112	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.009	CYP2C19-substrate:	0.701
CYP2C9-inhibitor:	0.049	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.973 ? 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):

8.364

Half-life (T1/2):

1.161

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.503
Human Hepatotoxicity (H-HT):	0.401	Drug-induced Liver Injury (DILI):	0.859
AMES Toxicity:	0.481	Rat Oral Acute Toxicity:	0.548
Maximum Recommended Daily Dose:	0.573	Skin Sensitization:	0.962
Carcinogencity:	0.256	Eye Corrosion:	0.389
Eye Irritation:	0.989	Respiratory Toxicity:	0.502
Drug-induced Neurotoxicity:	0.02	Ototoxicity:	0.22
Hematotoxicity:	0.046	Drug-induced Nephrotoxicity:	0.011
Genotoxicity:	0.971	RPMI-8226 Immunitoxicity:	0.02
A549 Cytotoxicity:	0.779	Hek293 Cytotoxicity:	0.549
BCF:	1.148 ? 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:	3.965 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.008 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.681 ? 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
NPO8355	Zaluzania triloba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)97900-1]
NPO9285	Eupatorium kiirunense	Species	Asteraceae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15921421]
NPO9285	Eupatorium kiirunense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921421]
NPO10978	Annona senegalensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623038]
NPO10649	Guatteria ouregou	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8676127]
NPO10978	Annona senegalensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882434]
NPO8355	Zaluzania triloba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO785	Nephroma parile	Species	Nephromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO285	Homeria glauca	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10649	Guatteria ouregou	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9285	Eupatorium kiirunense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11096	Earina autumnalis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10978	Annona senegalensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO10649	Guatteria ouregou	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11096	Earina autumnalis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO785	Nephroma parile	Species	Nephromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9285	Eupatorium kiirunense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8355	Zaluzania triloba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10978	Annona senegalensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO285	Homeria glauca	n.a.	n.a.	n.a.	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 NPC294123 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	21097
0.1-0.2	25812
0.2-0.3	1933
0.3-0.4	628
0.4-0.5	272
0.5-0.6	97
0.6-0.7	15
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
0.7679	Intermediate Similarity	NPC286342
0.6897	Remote Similarity	NPC103342
0.629	Remote Similarity	NPC82325
0.6286	Remote Similarity	NPC276222
0.6286	Remote Similarity	NPC274618
0.6286	Remote Similarity	NPC118284
0.6286	Remote Similarity	NPC608147
0.623	Remote Similarity	NPC59951
0.6094	Remote Similarity	NPC279989
0.6066	Remote Similarity	NPC184536
0.6027	Remote Similarity	NPC127546
0.6027	Remote Similarity	NPC57625
0.6027	Remote Similarity	NPC173637
0.6027	Remote Similarity	NPC317489
0.6027	Remote Similarity	NPC223424
0.6027	Remote Similarity	NPC600591
0.5972	Remote Similarity	NPC67037
0.5972	Remote Similarity	NPC255615
0.5938	Remote Similarity	NPC603596
0.5921	Remote Similarity	NPC175107
0.5867	Remote Similarity	NPC52550
0.5844	Remote Similarity	NPC259957
0.5833	Remote Similarity	NPC179271
0.5823	Remote Similarity	NPC116864
0.5823	Remote Similarity	NPC244776
0.5811	Remote Similarity	NPC104677
0.5806	Remote Similarity	NPC123886
0.5733	Remote Similarity	NPC145038
0.5733	Remote Similarity	NPC56077
0.5733	Remote Similarity	NPC281131
0.5733	Remote Similarity	NPC253662
0.5733	Remote Similarity	NPC179950
0.5733	Remote Similarity	NPC88789
0.5733	Remote Similarity	NPC491374
0.5714	Remote Similarity	NPC214138
0.5714	Remote Similarity	NPC159579
0.5714	Remote Similarity	NPC149127
0.5714	Remote Similarity	NPC48093
0.5714	Remote Similarity	NPC163524
0.5714	Remote Similarity	NPC610359
0.5694	Remote Similarity	NPC54802
0.5694	Remote Similarity	NPC197304
0.5667	Remote Similarity	NPC20791
0.5641	Remote Similarity	NPC85707
0.5584	Remote Similarity	NPC216496
0.5574	Remote Similarity	NPC279121
0.5556	Remote Similarity	NPC269285
0.5556	Remote Similarity	NPC287979
0.5542	Remote Similarity	NPC473862
0.5513	Remote Similarity	NPC235260
0.5513	Remote Similarity	NPC155763
0.5513	Remote Similarity	NPC129217
0.5493	Remote Similarity	NPC97255
0.5469	Remote Similarity	NPC260895
0.5469	Remote Similarity	NPC176665
0.5469	Remote Similarity	NPC188871
0.5467	Remote Similarity	NPC111929
0.5467	Remote Similarity	NPC320283
0.5467	Remote Similarity	NPC41121
0.5455	Remote Similarity	NPC162351
0.5443	Remote Similarity	NPC484158
0.5443	Remote Similarity	NPC224530
0.5432	Remote Similarity	NPC95866
0.5405	Remote Similarity	NPC288084
0.5395	Remote Similarity	NPC470461
0.5362	Remote Similarity	NPC158874
0.5357	Remote Similarity	NPC203259
0.5357	Remote Similarity	NPC33054
0.5357	Remote Similarity	NPC176740
0.5357	Remote Similarity	NPC471725
0.5357	Remote Similarity	NPC134532
0.5357	Remote Similarity	NPC602582
0.5316	Remote Similarity	NPC182121
0.5294	Remote Similarity	NPC35167
0.5294	Remote Similarity	NPC144097
0.5286	Remote Similarity	NPC153512
0.5263	Remote Similarity	NPC476771
0.525	Remote Similarity	NPC189913
0.5244	Remote Similarity	NPC254855
0.5244	Remote Similarity	NPC94610
0.5238	Remote Similarity	NPC471748
0.5238	Remote Similarity	NPC67326
0.5205	Remote Similarity	NPC56786
0.5195	Remote Similarity	NPC77672
0.5195	Remote Similarity	NPC133671
0.5195	Remote Similarity	NPC135391
0.5195	Remote Similarity	NPC78263
0.5195	Remote Similarity	NPC250069
0.5195	Remote Similarity	NPC476772
0.5176	Remote Similarity	NPC155877
0.5176	Remote Similarity	NPC156869
0.5176	Remote Similarity	NPC605592
0.5172	Remote Similarity	NPC245452
0.5169	Remote Similarity	NPC471669
0.5169	Remote Similarity	NPC89127
0.5152	Remote Similarity	NPC305663
0.5152	Remote Similarity	NPC18772
0.5119	Remote Similarity	NPC29958
0.5116	Remote Similarity	NPC255157
0.5116	Remote Similarity	NPC259896
0.5114	Remote Similarity	NPC122467
0.5077	Remote Similarity	NPC266960
0.5075	Remote Similarity	NPC153758
0.5065	Remote Similarity	NPC135599
0.5065	Remote Similarity	NPC73855
0.5065	Remote Similarity	NPC113968
0.5065	Remote Similarity	NPC328940
0.5065	Remote Similarity	NPC277174
0.5065	Remote Similarity	NPC606877
0.5057	Remote Similarity	NPC253521
0.5057	Remote Similarity	NPC154741
0.5057	Remote Similarity	NPC113836
0.5055	Remote Similarity	NPC223426

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC294123 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4528
0.1-0.2	4547
0.2-0.3	68
0.3-0.4	4
0.4-0.5	0
0.5-0.6	3
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
0.5667	Remote Similarity	NPD1512	Phase 3
0.5574	Remote Similarity	NPD1511	Phase 2
0.5357	Remote Similarity	NPD6797	Phase 2

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