NPASS Compound

Natural Product: NPC539482

Natural Product ID	NPC539482
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7-dihydroxy-2-[3-hydroxy-4-[(2~{S},3~{S},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-6-methoxy-chromen-4-one
IUPAC Name	5,7-dihydroxy-2-[3-hydroxy-4-[(2~{S},3~{S},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-6-methoxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 56 59 0 0 0 0 0 0 0 0999 V2000 9.4609 0.0790 0.5089 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6698 0.0599 -0.6675 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3100 0.2378 -0.5937 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8128 1.5195 -0.6790 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7014 2.5917 -0.8368 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4530 1.7016 -0.6056 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5879 0.6280 -0.4492 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2989 0.7750 -0.3772 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4161 -0.1969 -0.2290 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0050 0.1168 -0.1644 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0756 -0.8637 -0.0124 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2841 -0.5360 0.0475 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7096 0.7672 -0.0443 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0157 1.1929 0.0031 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1344 0.3878 0.1514 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0330 0.5495 -0.8711 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1401 -0.2349 -0.8167 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9690 -1.5963 -1.4991 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9578 -2.3135 -0.9002 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8028 -0.3582 0.5081 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4270 -1.6150 0.5737 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9077 -0.2591 1.7003 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6819 0.2399 2.7672 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7907 0.7485 1.4866 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2778 2.0321 1.5073 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7282 1.7556 -0.2005 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1355 3.0768 -0.2952 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5953 1.4215 -0.2574 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9039 -1.4810 -0.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2786 -1.7145 -0.2126 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7341 -2.8785 -0.1354 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1387 -0.6532 -0.3675 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5053 -0.8685 -0.4383 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0240 -2.1657 -0.3530 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2697 0.8513 0.4542 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9650 -0.8898 0.6740 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8137 0.2942 1.3843 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0737 2.8892 -1.7068 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0224 2.6852 -0.6677 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2955 -1.9177 0.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0209 -1.3289 0.1695 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8568 -0.6634 0.2296 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9098 0.2805 -1.4941 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7378 -1.3686 -2.5791 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9271 -2.1304 -1.5012 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5571 -2.9847 -1.4990 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5973 0.4290 0.5909 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2850 -1.5989 0.0592 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5310 -1.2425 2.0319 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2415 0.9810 2.3855 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0224 0.6243 2.2670 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2062 2.4366 2.4101 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9805 3.3490 0.2110 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3092 2.2500 -0.3811 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2238 -2.3137 -0.0210 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9245 -2.7290 -1.1922 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 13 26 1 0 26 27 1 0 26 28 2 0 9 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 33 3 1 0 32 7 1 0 28 10 1 0 24 15 1 0 1 35 1 0 1 36 1 0 1 37 1 0 5 38 1 0 6 39 1 0 11 40 1 0 12 41 1 0 15 42 1 1 17 43 1 6 18 44 1 0 18 45 1 0 19 46 1 0 20 47 1 1 21 48 1 0 22 49 1 1 23 50 1 0 24 51 1 1 25 52 1 0 27 53 1 0 28 54 1 0 29 55 1 0 34 56 1 0 M END

Standard InCHIKey	FKEFURJFBYTFMP-NFXVSDQMSA-N
Standard InCHI	InChI=1S/C22H22O12/c1-31-21-11(26)6-14-16(18(21)28)10(25)5-13(32-14)8-2-3-12(9(24)4-8)33-22-20(30)19(29)17(27)15(7-23)34-22/h2-6,15,17,19-20,22-24,26-30H,7H2,1H3/t15-,17+,19-,20-,22+/m0/s1
SMILES	COC1=C(O)C=C2OC(C3=CC=C(O[C@@H]4O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]4O)C(O)=C3)=CC(=O)C2=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	478.11	Volume:	439.233 ? Van der Waals volume.
Dense:	1.089	LogP:	0.785 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.195 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.881 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	199.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.254	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.041	Fsp³:	0.318
MCE-18:	90.31 ? 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:	0.68	Fluc inhibitor:	0.303 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.971 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.888 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.117	Promiscuous compounds:	0.796

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.326	MDCK Permeability:	-5.279
Pgp-inhibitor:	0.0	Pgp-substrate:	0.832
PAMPA:	1.0 ? 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):	0.68
20% Bioavailability (F20%):	0.978	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.919
Plasma Protein Binding (PPB):	83.391%	Volume Distribution (VD):	-0.089
Fu:	14.781% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.326
OATP1B3 inhibitor:	0.72	BCRP inhibitor:	0.235
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.113	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.738	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.268
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.966
HLM stability:	0.041 ? 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):

2.439

Half-life (T1/2):

2.613

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.151
Human Hepatotoxicity (H-HT):	0.519	Drug-induced Liver Injury (DILI):	0.838
AMES Toxicity:	0.88	Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.104	Skin Sensitization:	0.995
Carcinogencity:	0.313	Eye Corrosion:	0.0
Eye Irritation:	0.884	Respiratory Toxicity:	0.173
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.68
Hematotoxicity:	0.339	Drug-induced Nephrotoxicity:	0.408
Genotoxicity:	0.849	RPMI-8226 Immunitoxicity:	0.165
A549 Cytotoxicity:	0.727	Hek293 Cytotoxicity:	0.448
BCF:	0.334 ? 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:	2.839 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.27 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.428 ? 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
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35889256]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36677644]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38474654]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38617605]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38695450]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39063231]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39135848]
NPO17698	Cirsium oligophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO17698	Cirsium oligophyllum	Species	Asteraceae	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 NPC539482 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	19300
0.1-0.2	26394
0.2-0.3	2736
0.3-0.4	975
0.4-0.5	321
0.5-0.6	83
0.6-0.7	38
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8267	Intermediate Similarity	NPC605067
0.7895	Intermediate Similarity	NPC191306
0.7342	Intermediate Similarity	NPC22832
0.6923	Remote Similarity	NPC58053
0.675	Remote Similarity	NPC186807
0.675	Remote Similarity	NPC45638
0.6707	Remote Similarity	NPC609478
0.6667	Remote Similarity	NPC256760
0.6667	Remote Similarity	NPC256283
0.6667	Remote Similarity	NPC201292
0.6585	Remote Similarity	NPC609451
0.6506	Remote Similarity	NPC486578
0.65	Remote Similarity	NPC143851
0.6463	Remote Similarity	NPC42773
0.6463	Remote Similarity	NPC21100
0.6463	Remote Similarity	NPC45522
0.6429	Remote Similarity	NPC88023
0.6429	Remote Similarity	NPC309025
0.6429	Remote Similarity	NPC602805
0.642	Remote Similarity	NPC93337
0.642	Remote Similarity	NPC95090
0.642	Remote Similarity	NPC27408
0.6386	Remote Similarity	NPC60735
0.6386	Remote Similarity	NPC26230
0.6341	Remote Similarity	NPC58716
0.6341	Remote Similarity	NPC105025
0.6341	Remote Similarity	NPC488080
0.6341	Remote Similarity	NPC169977
0.631	Remote Similarity	NPC101026
0.631	Remote Similarity	NPC120099
0.631	Remote Similarity	NPC488077
0.631	Remote Similarity	NPC601710
0.619	Remote Similarity	NPC285197
0.6118	Remote Similarity	NPC243930
0.6118	Remote Similarity	NPC21666
0.6098	Remote Similarity	NPC45618
0.6047	Remote Similarity	NPC311830
0.6047	Remote Similarity	NPC607707
0.6024	Remote Similarity	NPC146792
0.6024	Remote Similarity	NPC189142
0.6024	Remote Similarity	NPC77660
0.593	Remote Similarity	NPC601144
0.5833	Remote Similarity	NPC168822
0.5778	Remote Similarity	NPC603300
0.5747	Remote Similarity	NPC284960
0.5714	Remote Similarity	NPC261866
0.5714	Remote Similarity	NPC39360
0.5714	Remote Similarity	NPC254306
0.5714	Remote Similarity	NPC29763
0.5714	Remote Similarity	NPC210003
0.5698	Remote Similarity	NPC222936
0.5698	Remote Similarity	NPC472459
0.5694	Remote Similarity	NPC156222
0.5679	Remote Similarity	NPC183036
0.5667	Remote Similarity	NPC251417
0.5647	Remote Similarity	NPC259152
0.5616	Remote Similarity	NPC100887
0.5581	Remote Similarity	NPC610763
0.5532	Remote Similarity	NPC488073
0.5529	Remote Similarity	NPC83283
0.5517	Remote Similarity	NPC182045
0.55	Remote Similarity	NPC470402
0.5467	Remote Similarity	NPC255350
0.5465	Remote Similarity	NPC64305
0.5444	Remote Similarity	NPC203050
0.5444	Remote Similarity	NPC225434
0.5417	Remote Similarity	NPC209296
0.5402	Remote Similarity	NPC305811
0.5395	Remote Similarity	NPC160951
0.5385	Remote Similarity	NPC4390
0.5385	Remote Similarity	NPC600989
0.5361	Remote Similarity	NPC472991
0.5349	Remote Similarity	NPC110349
0.5342	Remote Similarity	NPC293183
0.5341	Remote Similarity	NPC475942
0.5341	Remote Similarity	NPC325555
0.5341	Remote Similarity	NPC226304
0.5341	Remote Similarity	NPC117260
0.5333	Remote Similarity	NPC307518
0.5326	Remote Similarity	NPC254540
0.5319	Remote Similarity	NPC3583
0.5319	Remote Similarity	NPC607513
0.5283	Remote Similarity	NPC198199
0.5281	Remote Similarity	NPC219904
0.5275	Remote Similarity	NPC601586
0.527	Remote Similarity	NPC241498
0.527	Remote Similarity	NPC284552
0.5263	Remote Similarity	NPC83508
0.5227	Remote Similarity	NPC245014
0.5227	Remote Similarity	NPC181712
0.5222	Remote Similarity	NPC229729
0.5222	Remote Similarity	NPC197285
0.5222	Remote Similarity	NPC606560
0.5217	Remote Similarity	NPC211594
0.5208	Remote Similarity	NPC472992
0.5195	Remote Similarity	NPC52005
0.5172	Remote Similarity	NPC289667
0.5172	Remote Similarity	NPC77672
0.5172	Remote Similarity	NPC133671
0.5172	Remote Similarity	NPC135391
0.5172	Remote Similarity	NPC78263
0.5172	Remote Similarity	NPC250069
0.5165	Remote Similarity	NPC607201
0.5161	Remote Similarity	NPC8856
0.5143	Remote Similarity	NPC470718
0.5138	Remote Similarity	NPC120952
0.5128	Remote Similarity	NPC25292
0.5114	Remote Similarity	NPC145038
0.5114	Remote Similarity	NPC56077
0.5114	Remote Similarity	NPC281131
0.5114	Remote Similarity	NPC253662
0.5114	Remote Similarity	NPC179950
0.5114	Remote Similarity	NPC88789
0.5114	Remote Similarity	NPC491374
0.5111	Remote Similarity	NPC488071
0.5109	Remote Similarity	NPC469931
0.5109	Remote Similarity	NPC488072
0.5102	Remote Similarity	NPC124155
0.5102	Remote Similarity	NPC150767
0.5056	Remote Similarity	NPC84265
0.5056	Remote Similarity	NPC24043
0.5056	Remote Similarity	NPC84362
0.5056	Remote Similarity	NPC603655
0.5054	Remote Similarity	NPC172807

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC539482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4922
0.1-0.2	4136
0.2-0.3	75
0.3-0.4	10
0.4-0.5	5
0.5-0.6	2
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
0.5467	Remote Similarity	NPD2801	Pre-clinical
0.5417	Remote Similarity	NPD7054	Phase 4

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