NPASS Compound

Natural Product: NPC41561

Natural Product ID	NPC41561
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OIUBYZLTFSLSBY-HMFCTUEFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	91363802
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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 53 56 0 0 0 0 0 0 0 0999 V2000 0.9216 -1.4032 -1.3948 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4373 -1.2479 -1.3617 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0477 -0.4378 -0.3993 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2065 0.1773 0.4903 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1772 0.0032 0.4361 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7821 -0.8080 -0.5283 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2287 -0.9266 -0.5040 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9364 -1.6893 -1.3952 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3325 -1.7034 -1.2433 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9895 -2.3979 -2.0531 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9583 -0.9902 -0.2532 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3257 -0.9872 -0.0829 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9143 -0.2450 0.9399 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1147 0.4917 1.7865 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7596 0.4918 1.6217 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1743 -0.2485 0.6017 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8991 -0.2532 0.4404 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7117 1.2369 2.8140 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0959 -1.7313 -0.9426 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3526 -2.4270 -2.4115 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7328 0.9955 1.4731 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 -0.3388 -0.4360 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3151 0.3319 0.3088 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0630 1.3129 -0.5774 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1590 2.0195 0.1874 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4199 1.3435 1.5179 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3863 -0.1320 1.2957 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5355 -0.6177 0.4369 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6177 -2.0153 0.4538 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1731 -0.5917 0.8959 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6135 1.7524 2.0805 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3452 1.9885 -0.5394 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1447 2.2815 -0.9760 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3182 -2.0403 -2.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0703 -1.7475 -2.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7676 0.5252 1.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9779 -0.2469 1.0670 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1163 1.0619 2.2738 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0284 2.1623 2.6400 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8397 -1.3524 -1.5247 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4856 -2.2283 -3.3956 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3587 1.9139 1.6083 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8822 0.9210 1.1127 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4701 0.8521 -1.4966 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9098 3.0785 0.3830 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5955 1.6127 2.1957 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5818 -0.5960 2.3109 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3533 -0.3438 -0.6214 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4932 -0.2424 0.8142 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0489 -2.3741 -0.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3561 1.7426 1.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2256 2.1913 -1.4923 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2763 1.8755 -1.2823 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 4 21 1 0 3 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 26 31 1 0 25 32 1 0 24 33 1 0 6 1 1 0 17 7 1 0 30 23 1 0 16 11 1 0 1 34 1 0 2 35 1 0 5 36 1 0 13 37 1 0 15 38 1 0 18 39 1 0 19 40 1 0 20 41 1 0 21 42 1 0 23 43 1 1 24 44 1 6 25 45 1 1 26 46 1 1 27 47 1 1 28 48 1 0 28 49 1 0 29 50 1 0 31 51 1 0 32 52 1 0 33 53 1 0 M END

Standard InCHIKey	OIUBYZLTFSLSBY-HMFCTUEFSA-N
Standard InCHI	InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)32-11-2-1-7(3-9(11)24)20-18(29)16(27)14-10(25)4-8(23)5-12(14)31-20/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15+,17+,19-,21-/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	464.1	Volume:	421.937 ? Van der Waals volume.
Dense:	1.1	LogP:	0.75 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.182 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.856 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	210.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.245	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.031	Fsp³:	0.286
MCE-18:	91.0 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.674	Fluc inhibitor:	0.314 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.843 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.764 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.309	Promiscuous compounds:	0.934

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.311	MDCK Permeability:	-5.009
Pgp-inhibitor:	0.0	Pgp-substrate:	0.34
PAMPA:	0.997 ? 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):	0.976
20% Bioavailability (F20%):	0.657	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.635
Plasma Protein Binding (PPB):	89.063%	Volume Distribution (VD):	-0.316
Fu:	7.471% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.955
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.764
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.115	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:	0.999
HLM stability:	0.86 ? 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):

2.648

Half-life (T1/2):

2.891

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.098
Human Hepatotoxicity (H-HT):	0.596	Drug-induced Liver Injury (DILI):	0.938
AMES Toxicity:	0.942	Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.149	Skin Sensitization:	0.998
Carcinogencity:	0.472	Eye Corrosion:	0.001
Eye Irritation:	0.919	Respiratory Toxicity:	0.165
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.61
Hematotoxicity:	0.281	Drug-induced Nephrotoxicity:	0.197
Genotoxicity:	0.956	RPMI-8226 Immunitoxicity:	0.119
A549 Cytotoxicity:	0.811	Hek293 Cytotoxicity:	0.683
BCF:	0.42 ? 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:	2.875 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.311 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.65 ? 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
NPO20196	Aplysia vaccaria	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22231	Fagara naranjillo	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20516	Hydrocotyle ranunculoides	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22430	Parnassius phoebus	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1956	Polygonatum multiflorum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3851	Silene tatarica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22430	Parnassius phoebus	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20516	Hydrocotyle ranunculoides	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7943	Micromelum tephrocarpum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20196	Aplysia vaccaria	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22231	Fagara naranjillo	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1956	Polygonatum multiflorum	Species	Asparagaceae	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 NPC41561 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	20087
0.1-0.2	25686
0.2-0.3	2683
0.3-0.4	900
0.4-0.5	332
0.5-0.6	109
0.6-0.7	42
0.7-0.8	0
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC21100
0.8986	High Similarity	NPC254306
0.8133	Intermediate Similarity	NPC197285
0.8	Intermediate Similarity	NPC191306
0.8	Intermediate Similarity	NPC60735
0.8	Intermediate Similarity	NPC26230
0.8	Intermediate Similarity	NPC285197
0.7895	Intermediate Similarity	NPC486578
0.7895	Intermediate Similarity	NPC609478
0.7436	Intermediate Similarity	NPC120099
0.6923	Remote Similarity	NPC64305
0.6914	Remote Similarity	NPC136761
0.6795	Remote Similarity	NPC143851
0.675	Remote Similarity	NPC472459
0.6585	Remote Similarity	NPC601710
0.6582	Remote Similarity	NPC77672
0.6582	Remote Similarity	NPC133671
0.6582	Remote Similarity	NPC135391
0.6582	Remote Similarity	NPC78263
0.6582	Remote Similarity	NPC250069
0.6506	Remote Similarity	NPC88023
0.6506	Remote Similarity	NPC309025
0.65	Remote Similarity	NPC145038
0.65	Remote Similarity	NPC282987
0.65	Remote Similarity	NPC56077
0.65	Remote Similarity	NPC281131
0.65	Remote Similarity	NPC253662
0.65	Remote Similarity	NPC179950
0.65	Remote Similarity	NPC277205
0.65	Remote Similarity	NPC37919
0.65	Remote Similarity	NPC323593
0.65	Remote Similarity	NPC88789
0.65	Remote Similarity	NPC203500
0.65	Remote Similarity	NPC491374
0.6484	Remote Similarity	NPC287889
0.6429	Remote Similarity	NPC203050
0.6429	Remote Similarity	NPC54394
0.6429	Remote Similarity	NPC225434
0.6429	Remote Similarity	NPC601586
0.642	Remote Similarity	NPC245014
0.642	Remote Similarity	NPC84265
0.6375	Remote Similarity	NPC19388
0.6375	Remote Similarity	NPC240431
0.6375	Remote Similarity	NPC55786
0.6341	Remote Similarity	NPC325555
0.6341	Remote Similarity	NPC226304
0.6265	Remote Similarity	NPC219904
0.6207	Remote Similarity	NPC187379
0.6122	Remote Similarity	NPC470718
0.6098	Remote Similarity	NPC609879
0.6071	Remote Similarity	NPC307938
0.6	Remote Similarity	NPC605067
0.5952	Remote Similarity	NPC117260
0.5909	Remote Similarity	NPC251417
0.5904	Remote Similarity	NPC156457
0.5897	Remote Similarity	NPC78697
0.5814	Remote Similarity	NPC22832
0.5802	Remote Similarity	NPC288084
0.5765	Remote Similarity	NPC138540
0.5732	Remote Similarity	NPC67037
0.5732	Remote Similarity	NPC255615
0.5714	Remote Similarity	NPC156869
0.5684	Remote Similarity	NPC256760
0.5684	Remote Similarity	NPC76831
0.5657	Remote Similarity	NPC219043
0.5638	Remote Similarity	NPC473327
0.5632	Remote Similarity	NPC21666
0.561	Remote Similarity	NPC34531
0.5595	Remote Similarity	NPC112755
0.5595	Remote Similarity	NPC170675
0.5529	Remote Similarity	NPC265530
0.5506	Remote Similarity	NPC170052
0.5506	Remote Similarity	NPC135846
0.55	Remote Similarity	NPC48984
0.5495	Remote Similarity	NPC29958
0.5495	Remote Similarity	NPC139320
0.5479	Remote Similarity	NPC50403
0.5479	Remote Similarity	NPC241838
0.5476	Remote Similarity	NPC111929
0.5476	Remote Similarity	NPC320283
0.5476	Remote Similarity	NPC41121
0.5446	Remote Similarity	NPC470712
0.5444	Remote Similarity	NPC4390
0.5444	Remote Similarity	NPC254855
0.5444	Remote Similarity	NPC94610
0.5444	Remote Similarity	NPC600989
0.5435	Remote Similarity	NPC471748
0.5435	Remote Similarity	NPC275454
0.5421	Remote Similarity	NPC192539
0.5412	Remote Similarity	NPC289667
0.5412	Remote Similarity	NPC127546
0.5412	Remote Similarity	NPC57625
0.5412	Remote Similarity	NPC108831
0.5412	Remote Similarity	NPC173637
0.5412	Remote Similarity	NPC317489
0.5412	Remote Similarity	NPC238376
0.5412	Remote Similarity	NPC223424
0.5412	Remote Similarity	NPC182634
0.5412	Remote Similarity	NPC600591
0.5393	Remote Similarity	NPC223747
0.5349	Remote Similarity	NPC8573
0.5341	Remote Similarity	NPC175107
0.5341	Remote Similarity	NPC481043
0.5333	Remote Similarity	NPC159103
0.5333	Remote Similarity	NPC470713
0.5319	Remote Similarity	NPC131745
0.5294	Remote Similarity	NPC135599
0.5294	Remote Similarity	NPC73855
0.5294	Remote Similarity	NPC113968
0.5294	Remote Similarity	NPC328940
0.5294	Remote Similarity	NPC277174
0.5294	Remote Similarity	NPC606877
0.5287	Remote Similarity	NPC488080
0.5287	Remote Similarity	NPC169977
0.5275	Remote Similarity	NPC116864
0.5275	Remote Similarity	NPC244776
0.5269	Remote Similarity	NPC470405
0.5263	Remote Similarity	NPC153755
0.5263	Remote Similarity	NPC609179
0.5253	Remote Similarity	NPC135358
0.5233	Remote Similarity	NPC261866
0.5233	Remote Similarity	NPC476405
0.5227	Remote Similarity	NPC42773
0.5227	Remote Similarity	NPC45522
0.5222	Remote Similarity	NPC607707
0.5213	Remote Similarity	NPC183672
0.5195	Remote Similarity	NPC125062
0.5172	Remote Similarity	NPC297987
0.5172	Remote Similarity	NPC95090
0.5172	Remote Similarity	NPC146792
0.5172	Remote Similarity	NPC27408
0.5161	Remote Similarity	NPC609888
0.5152	Remote Similarity	NPC292929
0.5139	Remote Similarity	NPC179271
0.5114	Remote Similarity	NPC58716
0.5111	Remote Similarity	NPC101026
0.5111	Remote Similarity	NPC243930
0.5111	Remote Similarity	NPC488077
0.5111	Remote Similarity	NPC224530
0.5111	Remote Similarity	NPC601144
0.5109	Remote Similarity	NPC477848
0.5106	Remote Similarity	NPC163242
0.5106	Remote Similarity	NPC272068
0.51	Remote Similarity	NPC602448
0.5098	Remote Similarity	NPC189564
0.5067	Remote Similarity	NPC28274
0.5059	Remote Similarity	NPC171821
0.5057	Remote Similarity	NPC58053
0.5057	Remote Similarity	NPC39360
0.5057	Remote Similarity	NPC45618
0.5057	Remote Similarity	NPC29763
0.5057	Remote Similarity	NPC83283
0.5057	Remote Similarity	NPC210003
0.5056	Remote Similarity	NPC599850
0.5055	Remote Similarity	NPC206123
0.5055	Remote Similarity	NPC606270
0.5053	Remote Similarity	NPC155877
0.5051	Remote Similarity	NPC220173
0.5049	Remote Similarity	NPC292019
0.5049	Remote Similarity	NPC202908
0.5048	Remote Similarity	NPC279473

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC41561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5269
0.1-0.2	3792
0.2-0.3	70
0.3-0.4	12
0.4-0.5	6
0.5-0.6	0
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
		NPD

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