NPASS Compound

Natural Product: NPC21045

Natural Product ID	NPC21045
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RNVUDWOQYYWXBJ-NNEMTEQFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	22838903
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 48 51 0 0 0 0 0 0 0 0999 V2000 -0.0169 -2.4096 1.4486 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3820 -3.7637 1.4848 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2964 -4.6599 0.7230 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3309 -4.2305 -0.0731 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6753 -2.9251 -0.1026 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9989 -1.9595 0.6705 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4204 -0.5726 0.5242 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7028 0.4997 0.9383 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1777 1.8118 0.7649 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5311 2.8042 1.1425 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3885 1.9839 0.1613 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9374 3.2421 -0.0537 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1449 3.4055 -0.6576 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8395 2.2848 -1.0660 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3162 1.0269 -0.8639 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0757 0.8803 -0.2424 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5921 -0.3102 -0.0568 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0644 2.4463 -1.6789 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2143 4.3264 0.3673 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5634 0.4085 1.5581 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7167 0.5009 0.7227 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8155 -0.4374 1.0424 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1217 0.0617 0.4567 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8407 1.0295 -0.6591 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9394 2.1411 -0.2391 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2105 1.8324 0.9051 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2283 0.3002 -1.7025 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8931 -0.9945 0.0063 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9587 -0.5474 2.4493 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0587 -5.9991 0.7538 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5505 -1.7361 2.0874 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1945 -4.0331 2.1240 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8423 -4.9678 -0.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4895 -2.5929 -0.7307 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5488 4.3839 -0.8132 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8664 0.1518 -1.1868 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7378 3.0730 -1.2454 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4199 4.7312 -0.1068 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3824 0.3964 -0.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6602 -1.4573 0.6297 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7109 0.5831 1.2627 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8246 1.3965 -1.0465 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5161 3.0847 -0.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1898 2.3833 -1.0400 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8852 -0.2045 -2.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7793 -1.0415 0.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7999 0.3705 2.7994 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6273 -6.6978 0.5150 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 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 22 29 1 0 3 30 1 0 6 1 1 0 17 7 1 0 26 21 1 0 16 11 1 0 1 31 1 0 2 32 1 0 4 33 1 0 5 34 1 0 13 35 1 0 15 36 1 0 18 37 1 0 19 38 1 0 21 39 1 0 22 40 1 6 23 41 1 1 24 42 1 6 25 43 1 0 25 44 1 0 27 45 1 0 28 46 1 0 29 47 1 0 30 48 1 0 M END

Standard InCHIKey	RNVUDWOQYYWXBJ-NNEMTEQFSA-N
Standard InCHI	InChI=1S/C20H18O10/c21-9-3-1-8(2-4-9)18-19(30-20-17(27)15(25)12(24)7-28-20)16(26)14-11(23)5-10(22)6-13(14)29-18/h1-6,12,15,17,20-25,27H,7H2/t12-,15-,17+,20?/m1/s1
SMILES	c1cc(ccc1c1c(c(=O)c2c(cc(cc2o1)O)O)OC1[C@H]([C@@H]([C@@H](CO1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	418.09	Volume:	387.061 ? Van der Waals volume.
Dense:	1.08	LogP:	1.166 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.346 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.856 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	24.0
TPSA:	170.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.35	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.804	Fsp³:	0.25
MCE-18:	85.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.575	Fluc inhibitor:	0.296 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.867 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.705 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.09	Promiscuous compounds:	0.668

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.236	MDCK Permeability:	-5.085
Pgp-inhibitor:	0.001	Pgp-substrate:	0.828
PAMPA:	0.996 ? 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):	0.0
20% Bioavailability (F20%):	0.037	30% Bioavailability (F30%):	0.308
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.166
Plasma Protein Binding (PPB):	85.839%	Volume Distribution (VD):	-0.051
Fu:	13.137% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.943
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.944
BSEP inhibitor:	0.961

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.006	CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.124
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.946 ? 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):

2.762

Half-life (T1/2):

2.681

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.367
Human Hepatotoxicity (H-HT):	0.41	Drug-induced Liver Injury (DILI):	0.563
AMES Toxicity:	0.599	Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.543	Skin Sensitization:	0.896
Carcinogencity:	0.317	Eye Corrosion:	0.003
Eye Irritation:	0.974	Respiratory Toxicity:	0.117
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.369
Hematotoxicity:	0.03	Drug-induced Nephrotoxicity:	0.114
Genotoxicity:	0.889	RPMI-8226 Immunitoxicity:	0.06
A549 Cytotoxicity:	0.143	Hek293 Cytotoxicity:	0.659
BCF:	0.874 ? 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:	3.458 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.565 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.978 ? 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
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	Flowers	Muyang, China	n.a.	PMID[24621197]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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 NPC21045 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	19973
0.1-0.2	26818
0.2-0.3	2084
0.3-0.4	549
0.4-0.5	212
0.5-0.6	99
0.6-0.7	83
0.7-0.8	0
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC54802
1.0	High Similarity	NPC197304
0.8906	High Similarity	NPC276222
0.8906	High Similarity	NPC274618
0.8906	High Similarity	NPC118284
0.8906	High Similarity	NPC608147
0.7867	Intermediate Similarity	NPC471079
0.7571	Intermediate Similarity	NPC111929
0.7571	Intermediate Similarity	NPC320283
0.7571	Intermediate Similarity	NPC41121
0.7465	Intermediate Similarity	NPC77672
0.7465	Intermediate Similarity	NPC133671
0.7465	Intermediate Similarity	NPC135391
0.7465	Intermediate Similarity	NPC78263
0.7465	Intermediate Similarity	NPC250069
0.7286	Intermediate Similarity	NPC288084
0.7089	Intermediate Similarity	NPC67326
0.7	Intermediate Similarity	NPC304741
0.6875	Remote Similarity	NPC173582
0.6875	Remote Similarity	NPC265885
0.6875	Remote Similarity	NPC181465
0.6875	Remote Similarity	NPC215710
0.6875	Remote Similarity	NPC473438
0.6875	Remote Similarity	NPC253788
0.6842	Remote Similarity	NPC159579
0.6795	Remote Similarity	NPC276377
0.6757	Remote Similarity	NPC127546
0.6757	Remote Similarity	NPC57625
0.6757	Remote Similarity	NPC173637
0.6757	Remote Similarity	NPC317489
0.6757	Remote Similarity	NPC223424
0.6757	Remote Similarity	NPC600591
0.6667	Remote Similarity	NPC145038
0.6667	Remote Similarity	NPC56077
0.6667	Remote Similarity	NPC470405
0.6667	Remote Similarity	NPC281131
0.6667	Remote Similarity	NPC253662
0.6667	Remote Similarity	NPC179950
0.6667	Remote Similarity	NPC103342
0.6667	Remote Similarity	NPC88789
0.6667	Remote Similarity	NPC491374
0.6623	Remote Similarity	NPC175107
0.6623	Remote Similarity	NPC129217
0.6538	Remote Similarity	NPC85707
0.6522	Remote Similarity	NPC262699
0.6522	Remote Similarity	NPC131217
0.6506	Remote Similarity	NPC129264
0.65	Remote Similarity	NPC116864
0.65	Remote Similarity	NPC244776
0.6486	Remote Similarity	NPC67037
0.6486	Remote Similarity	NPC255615
0.6447	Remote Similarity	NPC64305
0.6437	Remote Similarity	NPC292929
0.6437	Remote Similarity	NPC221342
0.6437	Remote Similarity	NPC476470
0.6429	Remote Similarity	NPC470125
0.641	Remote Similarity	NPC235260
0.641	Remote Similarity	NPC155763
0.6341	Remote Similarity	NPC139320
0.6322	Remote Similarity	NPC85751
0.6322	Remote Similarity	NPC19240
0.631	Remote Similarity	NPC255157
0.631	Remote Similarity	NPC259896
0.6282	Remote Similarity	NPC216496
0.6282	Remote Similarity	NPC472459
0.6279	Remote Similarity	NPC270448
0.625	Remote Similarity	NPC223747
0.6203	Remote Similarity	NPC48093
0.619	Remote Similarity	NPC203259
0.619	Remote Similarity	NPC33054
0.619	Remote Similarity	NPC176740
0.619	Remote Similarity	NPC471725
0.619	Remote Similarity	NPC134532
0.619	Remote Similarity	NPC156869
0.619	Remote Similarity	NPC602582
0.6184	Remote Similarity	NPC135599
0.6184	Remote Similarity	NPC73855
0.6184	Remote Similarity	NPC113968
0.6184	Remote Similarity	NPC328940
0.6184	Remote Similarity	NPC277174
0.6184	Remote Similarity	NPC606877
0.6173	Remote Similarity	NPC203050
0.6173	Remote Similarity	NPC170052
0.6173	Remote Similarity	NPC225434
0.6173	Remote Similarity	NPC476215
0.6173	Remote Similarity	NPC135846
0.6136	Remote Similarity	NPC76831
0.6125	Remote Similarity	NPC259957
0.6125	Remote Similarity	NPC224530
0.6111	Remote Similarity	NPC214621
0.6111	Remote Similarity	NPC34267
0.6104	Remote Similarity	NPC19388
0.6104	Remote Similarity	NPC240431
0.6104	Remote Similarity	NPC104677
0.6104	Remote Similarity	NPC55786
0.6047	Remote Similarity	NPC296018
0.6047	Remote Similarity	NPC153755
0.6026	Remote Similarity	NPC265530
0.6	Remote Similarity	NPC60735
0.6	Remote Similarity	NPC219904
0.6	Remote Similarity	NPC26230
0.5978	Remote Similarity	NPC189564
0.5977	Remote Similarity	NPC12013
0.5977	Remote Similarity	NPC11432
0.5977	Remote Similarity	NPC477613
0.5949	Remote Similarity	NPC52550
0.5926	Remote Similarity	NPC120099
0.5921	Remote Similarity	NPC34531
0.5914	Remote Similarity	NPC219043
0.5909	Remote Similarity	NPC104883
0.5909	Remote Similarity	NPC488679
0.5897	Remote Similarity	NPC249281
0.5882	Remote Similarity	NPC163242
0.5882	Remote Similarity	NPC272068
0.5875	Remote Similarity	NPC138927
0.5875	Remote Similarity	NPC325555
0.5875	Remote Similarity	NPC226304
0.587	Remote Similarity	NPC203145
0.5824	Remote Similarity	NPC223426
0.5823	Remote Similarity	NPC297987
0.5821	Remote Similarity	NPC286342
0.5778	Remote Similarity	NPC476472
0.5778	Remote Similarity	NPC294815
0.5778	Remote Similarity	NPC16194
0.5765	Remote Similarity	NPC29958
0.5765	Remote Similarity	NPC609888
0.575	Remote Similarity	NPC46420
0.575	Remote Similarity	NPC488080
0.575	Remote Similarity	NPC169977
0.573	Remote Similarity	NPC37668
0.5698	Remote Similarity	NPC471748
0.5698	Remote Similarity	NPC39834
0.5682	Remote Similarity	NPC488074
0.5672	Remote Similarity	NPC184536
0.5667	Remote Similarity	NPC205824
0.5652	Remote Similarity	NPC602448
0.5632	Remote Similarity	NPC150164
0.5632	Remote Similarity	NPC605592
0.5625	Remote Similarity	NPC8573
0.5618	Remote Similarity	NPC245452
0.561	Remote Similarity	NPC182121
0.5604	Remote Similarity	NPC471669
0.5591	Remote Similarity	NPC96605
0.5591	Remote Similarity	NPC280642
0.5591	Remote Similarity	NPC81042
0.5588	Remote Similarity	NPC59951
0.5579	Remote Similarity	NPC48984
0.557	Remote Similarity	NPC476771
0.5568	Remote Similarity	NPC144097
0.5556	Remote Similarity	NPC473327
0.5542	Remote Similarity	NPC609478
0.5529	Remote Similarity	NPC254855
0.5529	Remote Similarity	NPC94610
0.5529	Remote Similarity	NPC95866
0.5521	Remote Similarity	NPC217520
0.5506	Remote Similarity	NPC154741
0.55	Remote Similarity	NPC476772
0.5493	Remote Similarity	NPC279989
0.5476	Remote Similarity	NPC209023
0.5476	Remote Similarity	NPC116458
0.5476	Remote Similarity	NPC246943
0.5455	Remote Similarity	NPC65563
0.5455	Remote Similarity	NPC470949
0.5417	Remote Similarity	NPC292019
0.5417	Remote Similarity	NPC202908
0.5417	Remote Similarity	NPC477895
0.5393	Remote Similarity	NPC473571
0.5393	Remote Similarity	NPC110941
0.5393	Remote Similarity	NPC186816
0.5385	Remote Similarity	NPC122467
0.5385	Remote Similarity	NPC72016
0.5366	Remote Similarity	NPC24043
0.5357	Remote Similarity	NPC189913
0.5347	Remote Similarity	NPC474522
0.534	Remote Similarity	NPC192539
0.5333	Remote Similarity	NPC61904
0.5326	Remote Similarity	NPC101399
0.5326	Remote Similarity	NPC221288
0.5326	Remote Similarity	NPC217822
0.5326	Remote Similarity	NPC11847
0.5326	Remote Similarity	NPC198938
0.5326	Remote Similarity	NPC194836
0.5326	Remote Similarity	NPC91493
0.5326	Remote Similarity	NPC603079
0.5326	Remote Similarity	NPC605081
0.5319	Remote Similarity	NPC218161
0.5281	Remote Similarity	NPC155877
0.5275	Remote Similarity	NPC297503
0.5275	Remote Similarity	NPC75574
0.5269	Remote Similarity	NPC135831
0.5269	Remote Similarity	NPC89127
0.5253	Remote Similarity	NPC139571
0.5248	Remote Similarity	NPC480445
0.5233	Remote Similarity	NPC66087
0.5217	Remote Similarity	NPC123886
0.5211	Remote Similarity	NPC82325
0.5204	Remote Similarity	NPC470712
0.5181	Remote Similarity	NPC305811
0.5149	Remote Similarity	NPC488734
0.5149	Remote Similarity	NPC474093

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC21045 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5085
0.1-0.2	4007
0.2-0.3	44
0.3-0.4	9
0.4-0.5	4
0.5-0.6	0
0.6-0.7	1
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
0.619	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