NPASS Compound

Natural Product: NPC41464

Natural Product ID	NPC41464
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OPJZLUXFQFQYAI-KHPGOBPMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5748375
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 53 56 0 0 0 0 0 0 0 0999 V2000 -1.1373 -2.4088 -0.8409 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3845 -3.7898 -0.8199 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5918 -4.3085 -0.4253 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6052 -3.4548 -0.0336 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3395 -2.1067 -0.0618 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1325 -1.5650 -0.4542 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9355 -0.1244 -0.3913 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7408 0.5208 -0.3906 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7247 1.9141 -0.3302 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3454 2.5663 -0.3296 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9232 2.5981 -0.2691 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9861 3.9716 -0.2059 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1892 4.6492 -0.1433 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3815 3.9472 -0.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3183 2.5862 -0.2056 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1044 1.8859 -0.2695 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0721 0.6007 -0.3283 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5900 4.6174 -0.0805 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7650 4.6717 -0.2071 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4763 -0.1222 -0.4346 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1906 -0.4376 0.7497 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9218 -1.7143 0.7800 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2907 -1.3177 0.2406 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2765 0.1767 0.2616 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5231 0.6864 0.9427 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7133 0.2260 0.0972 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5736 0.7510 -1.1935 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4745 2.0674 1.0155 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1601 0.5665 0.9927 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4725 -1.8144 -1.0646 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1069 -2.1931 2.0996 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8285 -3.9731 0.3658 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8322 -5.6821 -0.4062 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1716 -2.0744 -1.1989 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5615 -4.4437 -1.1361 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1655 -1.4526 0.2554 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2009 5.7374 -0.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2317 1.9947 -0.2077 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4615 4.2683 -0.4506 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6059 5.3835 0.5146 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4735 -0.3004 1.5975 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5759 -2.5289 0.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0765 -1.7773 0.8700 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2472 0.5875 -0.7822 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5993 0.2149 1.9452 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7043 -0.8781 0.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6619 0.6051 0.5253 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5848 1.7207 -1.1516 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3253 2.4980 0.7359 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2137 -2.4782 -1.1024 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0184 -1.4058 2.7009 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6718 -3.4074 0.2138 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3533 -6.2540 0.2837 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 26 27 1 0 25 28 1 0 24 29 1 0 23 30 1 0 22 31 1 0 4 32 1 0 3 33 1 0 6 1 1 0 17 7 1 0 29 21 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 21 41 1 1 22 42 1 6 23 43 1 1 24 44 1 6 25 45 1 1 26 46 1 0 26 47 1 0 27 48 1 0 28 49 1 0 30 50 1 0 31 51 1 0 32 52 1 0 33 53 1 0 M END

Standard InCHIKey	OPJZLUXFQFQYAI-KHPGOBPMSA-N
Standard InCHI	InChI=1S/C21H20O12/c22-6-12(27)19-16(29)17(30)21(32-19)33-20-15(28)14-11(26)4-8(23)5-13(14)31-18(20)7-1-2-9(24)10(25)3-7/h1-5,12,16-17,19,21-27,29-30H,6H2/t12-,16-,17-,19+,21+/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	464.1	Volume:	421.937 ? Van der Waals volume.
Dense:	1.1	LogP:	0.71 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.081 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.549 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
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:	0.224	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.158	Fsp³:	0.286
MCE-18:	89.0 ? 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:	1
Colloidal aggregators:	0.664	Fluc inhibitor:	0.299 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.919 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.517 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.305	Promiscuous compounds:	0.908

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.193	MDCK Permeability:	-4.919
Pgp-inhibitor:	0.0	Pgp-substrate:	0.176
PAMPA:	0.946 ? 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):	0.334
20% Bioavailability (F20%):	0.742	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.288
Plasma Protein Binding (PPB):	82.944%	Volume Distribution (VD):	-0.082
Fu:	15.717% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.94
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.877
BSEP inhibitor:	0.014

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.016	CYP2D6-substrate:	0.723
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.028
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.725 ? 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):

3.582

Half-life (T1/2):

2.602

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.236
Human Hepatotoxicity (H-HT):	0.472	Drug-induced Liver Injury (DILI):	0.826
AMES Toxicity:	0.889	Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.192	Skin Sensitization:	1.0
Carcinogencity:	0.171	Eye Corrosion:	0.001
Eye Irritation:	0.937	Respiratory Toxicity:	0.046
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.793
Hematotoxicity:	0.025	Drug-induced Nephrotoxicity:	0.076
Genotoxicity:	0.986	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.812	Hek293 Cytotoxicity:	0.529
BCF:	0.492 ? 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:	3.043 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.529 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.833 ? 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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21072	Rhododendron dauricum	Species	Ericaceae	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 NPC41464 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	23310
0.1-0.2	23390
0.2-0.3	2216
0.3-0.4	504
0.4-0.5	202
0.5-0.6	90
0.6-0.7	76
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8529	High Similarity	NPC67037
0.8529	High Similarity	NPC255615
0.7917	Intermediate Similarity	NPC145038
0.7917	Intermediate Similarity	NPC56077
0.7917	Intermediate Similarity	NPC281131
0.7917	Intermediate Similarity	NPC253662
0.7917	Intermediate Similarity	NPC179950
0.7917	Intermediate Similarity	NPC88789
0.7917	Intermediate Similarity	NPC491374
0.7778	Intermediate Similarity	NPC127546
0.7778	Intermediate Similarity	NPC57625
0.7778	Intermediate Similarity	NPC173637
0.7778	Intermediate Similarity	NPC317489
0.7778	Intermediate Similarity	NPC223424
0.7778	Intermediate Similarity	NPC600591
0.7606	Intermediate Similarity	NPC288084
0.7468	Intermediate Similarity	NPC29958
0.7375	Intermediate Similarity	NPC471748
0.7368	Intermediate Similarity	NPC175107
0.7361	Intermediate Similarity	NPC34531
0.7284	Intermediate Similarity	NPC605592
0.7123	Intermediate Similarity	NPC276222
0.7123	Intermediate Similarity	NPC274618
0.7123	Intermediate Similarity	NPC118284
0.7123	Intermediate Similarity	NPC608147
0.7105	Intermediate Similarity	NPC52550
0.7073	Intermediate Similarity	NPC156869
0.7067	Intermediate Similarity	NPC77672
0.7067	Intermediate Similarity	NPC133671
0.7067	Intermediate Similarity	NPC135391
0.7067	Intermediate Similarity	NPC78263
0.7067	Intermediate Similarity	NPC250069
0.7	Intermediate Similarity	NPC116864
0.7	Intermediate Similarity	NPC244776
0.6951	Remote Similarity	NPC67326
0.6933	Remote Similarity	NPC111929
0.6933	Remote Similarity	NPC320283
0.6933	Remote Similarity	NPC41121
0.6923	Remote Similarity	NPC159579
0.6867	Remote Similarity	NPC203259
0.6867	Remote Similarity	NPC33054
0.6867	Remote Similarity	NPC176740
0.6867	Remote Similarity	NPC471725
0.6867	Remote Similarity	NPC134532
0.6867	Remote Similarity	NPC602582
0.6842	Remote Similarity	NPC19388
0.6842	Remote Similarity	NPC240431
0.6842	Remote Similarity	NPC55786
0.679	Remote Similarity	NPC254855
0.679	Remote Similarity	NPC94610
0.6711	Remote Similarity	NPC135599
0.6711	Remote Similarity	NPC73855
0.6711	Remote Similarity	NPC113968
0.6711	Remote Similarity	NPC328940
0.6711	Remote Similarity	NPC277174
0.6711	Remote Similarity	NPC606877
0.6709	Remote Similarity	NPC182121
0.6706	Remote Similarity	NPC154741
0.6627	Remote Similarity	NPC139320
0.6591	Remote Similarity	NPC471669
0.6585	Remote Similarity	NPC95866
0.6538	Remote Similarity	NPC64305
0.65	Remote Similarity	NPC235260
0.65	Remote Similarity	NPC60735
0.65	Remote Similarity	NPC155763
0.65	Remote Similarity	NPC26230
0.6471	Remote Similarity	NPC155877
0.6463	Remote Similarity	NPC203050
0.6463	Remote Similarity	NPC225434
0.642	Remote Similarity	NPC120099
0.6418	Remote Similarity	NPC286342
0.6404	Remote Similarity	NPC135831
0.6395	Remote Similarity	NPC255157
0.6395	Remote Similarity	NPC259896
0.6375	Remote Similarity	NPC472459
0.6364	Remote Similarity	NPC37668
0.6344	Remote Similarity	NPC292019
0.6344	Remote Similarity	NPC202908
0.6341	Remote Similarity	NPC223747
0.6316	Remote Similarity	NPC54802
0.6316	Remote Similarity	NPC197304
0.6296	Remote Similarity	NPC219904
0.6282	Remote Similarity	NPC476771
0.625	Remote Similarity	NPC245452
0.6235	Remote Similarity	NPC471079
0.6173	Remote Similarity	NPC42773
0.6173	Remote Similarity	NPC45522
0.6173	Remote Similarity	NPC325555
0.6173	Remote Similarity	NPC226304
0.6163	Remote Similarity	NPC173582
0.6163	Remote Similarity	NPC265885
0.6163	Remote Similarity	NPC181465
0.6163	Remote Similarity	NPC215710
0.6163	Remote Similarity	NPC473438
0.6163	Remote Similarity	NPC253788
0.6145	Remote Similarity	NPC209023
0.6136	Remote Similarity	NPC296018
0.6125	Remote Similarity	NPC265530
0.6125	Remote Similarity	NPC136042
0.6098	Remote Similarity	NPC129217
0.6087	Remote Similarity	NPC223426
0.6071	Remote Similarity	NPC170052
0.6071	Remote Similarity	NPC135846
0.6049	Remote Similarity	NPC305811
0.6024	Remote Similarity	NPC609478
0.6022	Remote Similarity	NPC81042
0.6	Remote Similarity	NPC122467
0.6	Remote Similarity	NPC104883
0.6	Remote Similarity	NPC488679
0.6	Remote Similarity	NPC476772
0.5977	Remote Similarity	NPC39834
0.5976	Remote Similarity	NPC599850
0.5955	Remote Similarity	NPC253521
0.5955	Remote Similarity	NPC113836
0.5882	Remote Similarity	NPC476215
0.587	Remote Similarity	NPC89127
0.5854	Remote Similarity	NPC271692
0.5843	Remote Similarity	NPC129264
0.5843	Remote Similarity	NPC35167
0.5833	Remote Similarity	NPC85707
0.5833	Remote Similarity	NPC224530
0.5824	Remote Similarity	NPC270448
0.5795	Remote Similarity	NPC470405
0.5795	Remote Similarity	NPC163242
0.5795	Remote Similarity	NPC272068
0.5783	Remote Similarity	NPC216496
0.5778	Remote Similarity	NPC470125
0.5778	Remote Similarity	NPC153755
0.5765	Remote Similarity	NPC605784
0.5743	Remote Similarity	NPC156785
0.573	Remote Similarity	NPC304741
0.5729	Remote Similarity	NPC189564
0.5714	Remote Similarity	NPC488071
0.5699	Remote Similarity	NPC476472
0.5699	Remote Similarity	NPC294815
0.5699	Remote Similarity	NPC16194
0.5682	Remote Similarity	NPC476773
0.5667	Remote Similarity	NPC144097
0.5663	Remote Similarity	NPC84362
0.5663	Remote Similarity	NPC27640
0.5652	Remote Similarity	NPC473327
0.5647	Remote Similarity	NPC259957
0.5647	Remote Similarity	NPC189913
0.5625	Remote Similarity	NPC203145
0.5612	Remote Similarity	NPC303694
0.5604	Remote Similarity	NPC488073
0.5604	Remote Similarity	NPC488074
0.5595	Remote Similarity	NPC138927
0.5591	Remote Similarity	NPC97119
0.5571	Remote Similarity	NPC103342
0.5543	Remote Similarity	NPC75574
0.5542	Remote Similarity	NPC8573
0.5542	Remote Similarity	NPC297987
0.5532	Remote Similarity	NPC85751
0.5532	Remote Similarity	NPC19240
0.5529	Remote Similarity	NPC48093
0.5521	Remote Similarity	NPC214621
0.5521	Remote Similarity	NPC34267
0.5506	Remote Similarity	NPC609888
0.5481	Remote Similarity	NPC241781
0.5476	Remote Similarity	NPC488080
0.5476	Remote Similarity	NPC169977
0.5465	Remote Similarity	NPC484158
0.5444	Remote Similarity	NPC196127
0.5435	Remote Similarity	NPC61904
0.5435	Remote Similarity	NPC126784
0.5435	Remote Similarity	NPC241423
0.5426	Remote Similarity	NPC205824
0.5422	Remote Similarity	NPC249281
0.5422	Remote Similarity	NPC104677
0.5422	Remote Similarity	NPC254306
0.5412	Remote Similarity	NPC59534
0.5385	Remote Similarity	NPC473862
0.5385	Remote Similarity	NPC480444
0.5376	Remote Similarity	NPC12013
0.5376	Remote Similarity	NPC11432
0.5376	Remote Similarity	NPC477613
0.5368	Remote Similarity	NPC76831
0.5368	Remote Similarity	NPC220173
0.5354	Remote Similarity	NPC219043
0.5333	Remote Similarity	NPC480466
0.5312	Remote Similarity	NPC292929
0.5294	Remote Similarity	NPC46420
0.5281	Remote Similarity	NPC265115
0.5258	Remote Similarity	NPC470446
0.5258	Remote Similarity	NPC602448
0.5227	Remote Similarity	NPC116458
0.5227	Remote Similarity	NPC246943
0.5213	Remote Similarity	NPC297503
0.5213	Remote Similarity	NPC483415
0.52	Remote Similarity	NPC279989
0.5196	Remote Similarity	NPC139571
0.5165	Remote Similarity	NPC258044
0.5165	Remote Similarity	NPC217387
0.5155	Remote Similarity	NPC221342
0.5155	Remote Similarity	NPC476470
0.5149	Remote Similarity	NPC217520
0.5143	Remote Similarity	NPC162394
0.5143	Remote Similarity	NPC488740
0.5143	Remote Similarity	NPC474522

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC41464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5765
0.1-0.2	3335
0.2-0.3	38
0.3-0.4	7
0.4-0.5	3
0.5-0.6	1
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
0.6867	Remote Similarity	NPD6797	Phase 2
0.5208	Remote Similarity	NPD7251	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