NPASS Compound

Natural Product: NPC576285

Natural Product ID	NPC576285
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-dihydroxyphenyl)-5-methoxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dihydroxyphenyl)-5-methoxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-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 55 58 0 0 0 0 0 0 0 0999 V2000 -1.2635 3.7967 -0.1783 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0587 3.2907 -0.1845 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2423 1.9324 -0.1068 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8067 1.0268 -0.0223 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6446 -0.3351 0.0561 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6518 -1.2605 0.1407 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9992 -0.9566 0.1596 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6045 -1.3463 1.3606 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9317 -1.0333 1.4426 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1246 0.4546 1.7438 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5118 0.7158 1.8173 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7779 -1.4886 0.2966 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0243 -0.8701 0.3884 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1893 -1.0875 -1.0452 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9043 -1.7217 -2.0416 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7491 -1.5304 -1.0330 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1253 -1.0674 -2.1863 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6948 -0.7617 0.0446 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7742 0.0916 -0.0375 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5253 1.4435 -0.1129 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6192 2.2969 -0.1955 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4104 3.5182 -0.2640 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 1.7045 -0.1940 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0728 0.3512 -0.1176 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4130 -0.2429 -0.1190 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5240 -1.6154 -0.0393 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7584 -2.2555 -0.0351 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9042 -1.4854 -0.1135 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1585 -2.0783 -0.1128 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7766 -0.1158 -0.1926 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9467 0.6302 -0.2703 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5253 0.5112 -0.1955 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0070 -0.3997 -0.0421 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7447 3.5495 -1.1258 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8703 3.3819 0.6535 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2213 4.9026 0.0132 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8037 1.4534 -0.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1569 0.1296 0.0962 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3383 -1.5540 2.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6615 0.6700 2.7187 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7251 1.1004 0.9568 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7932 1.3827 1.1612 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9097 -2.5935 0.3625 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6495 -1.3580 0.9871 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2796 -0.0010 -1.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8047 -2.6848 -1.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6500 -2.6185 -0.9896 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4037 -0.4313 -2.0201 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8850 -1.8247 0.1042 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7192 2.3539 -0.2576 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6575 -2.2607 0.0239 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8439 -3.3358 0.0276 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3587 -2.8390 0.5373 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0345 1.4518 -0.8351 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5528 1.5847 -0.2611 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 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 9 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 5 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 2 0 24 33 1 0 20 3 1 0 32 25 1 0 16 7 1 0 33 19 1 0 1 34 1 0 1 35 1 0 1 36 1 0 4 37 1 0 7 38 1 6 9 39 1 1 10 40 1 0 10 41 1 0 11 42 1 0 12 43 1 6 13 44 1 0 14 45 1 6 15 46 1 0 16 47 1 1 17 48 1 0 18 49 1 0 23 50 1 0 26 51 1 0 27 52 1 0 29 53 1 0 31 54 1 0 32 55 1 0 M END

Standard InCHIKey	FAFFFXZNMUEBBD-AOIWZFSPSA-N
Standard InCHI	InChI=1S/C22H22O11/c1-30-15-5-10(31-22-21(29)20(28)19(27)17(8-23)33-22)6-16-18(15)13(26)7-14(32-16)9-2-3-11(24)12(25)4-9/h2-7,17,19-25,27-29H,8H2,1H3/t17-,19+,20-,21+,22+/m0/s1
SMILES	COC1=CC(O[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC2=C1C(=O)C=C(C1=CC=C(O)C(O)=C1)O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	462.12	Volume:	430.443 ? Van der Waals volume.
Dense:	1.074	LogP:	0.733 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.288 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.408 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	179.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.282	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.888	Fsp³:	0.318
MCE-18:	86.966 ? 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:	0.672	Fluc inhibitor:	0.296 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.99 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.881 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.102	Promiscuous compounds:	0.399

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.332	MDCK Permeability:	-5.319
Pgp-inhibitor:	0.0	Pgp-substrate:	0.107
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):	0.354
20% Bioavailability (F20%):	0.934	30% Bioavailability (F30%):	0.982
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.773
Plasma Protein Binding (PPB):	80.312%	Volume Distribution (VD):	-0.044
Fu:	18.042% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.99
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.785
BSEP inhibitor:	0.079

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.242
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.013
HLM stability:	0.0 ? 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):

3.738

Half-life (T1/2):

3.335

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.265
Human Hepatotoxicity (H-HT):	0.508	Drug-induced Liver Injury (DILI):	0.938
AMES Toxicity:	0.831	Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.075	Skin Sensitization:	0.989
Carcinogencity:	0.265	Eye Corrosion:	0.0
Eye Irritation:	0.601	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.899
Hematotoxicity:	0.121	Drug-induced Nephrotoxicity:	0.285
Genotoxicity:	0.946	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.328	Hek293 Cytotoxicity:	0.186
BCF:	0.537 ? 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:	3.201 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.748 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.943 ? 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
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30892891]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO47792	Juncus acutus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO58545	Luzula arcuata	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO60443	Luzula nutans	Genus	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO63946	Luzula sylvatica	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1150	Juncus effusus	Species	Juncaceae	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 NPC576285 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	23518
0.1-0.2	22242
0.2-0.3	2714
0.3-0.4	950
0.4-0.5	297
0.5-0.6	85
0.6-0.7	31
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8857	High Similarity	NPC610763
0.7532	Intermediate Similarity	NPC284960
0.7467	Intermediate Similarity	NPC168822
0.7467	Intermediate Similarity	NPC189142
0.7467	Intermediate Similarity	NPC77660
0.7368	Intermediate Similarity	NPC45638
0.7333	Intermediate Similarity	NPC110349
0.7273	Intermediate Similarity	NPC182045
0.7273	Intermediate Similarity	NPC201292
0.6923	Remote Similarity	NPC58716
0.6667	Remote Similarity	NPC83283
0.6512	Remote Similarity	NPC473512
0.65	Remote Similarity	NPC84362
0.6463	Remote Similarity	NPC22832
0.6456	Remote Similarity	NPC39360
0.6456	Remote Similarity	NPC29763
0.6456	Remote Similarity	NPC210003
0.6386	Remote Similarity	NPC311830
0.6375	Remote Similarity	NPC93337
0.6375	Remote Similarity	NPC95090
0.6375	Remote Similarity	NPC27408
0.6296	Remote Similarity	NPC105025
0.625	Remote Similarity	NPC58053
0.625	Remote Similarity	NPC19709
0.622	Remote Similarity	NPC222936
0.622	Remote Similarity	NPC599850
0.6173	Remote Similarity	NPC277205
0.6173	Remote Similarity	NPC37919
0.6173	Remote Similarity	NPC136042
0.6136	Remote Similarity	NPC129827
0.6136	Remote Similarity	NPC607513
0.6098	Remote Similarity	NPC186807
0.6071	Remote Similarity	NPC243930
0.6071	Remote Similarity	NPC601144
0.6071	Remote Similarity	NPC605067
0.6049	Remote Similarity	NPC261866
0.6024	Remote Similarity	NPC100720
0.6024	Remote Similarity	NPC117260
0.6	Remote Similarity	NPC602805
0.6	Remote Similarity	NPC607707
0.5977	Remote Similarity	NPC8856
0.5976	Remote Similarity	NPC146792
0.5976	Remote Similarity	NPC609879
0.5952	Remote Similarity	NPC488071
0.5909	Remote Similarity	NPC473657
0.587	Remote Similarity	NPC150767
0.5833	Remote Similarity	NPC42773
0.5833	Remote Similarity	NPC45522
0.5814	Remote Similarity	NPC479406
0.5814	Remote Similarity	NPC605784
0.5778	Remote Similarity	NPC3583
0.5765	Remote Similarity	NPC169404
0.5765	Remote Similarity	NPC176186
0.5765	Remote Similarity	NPC479402
0.5765	Remote Similarity	NPC609451
0.5747	Remote Similarity	NPC190003
0.5747	Remote Similarity	NPC479407
0.5714	Remote Similarity	NPC245014
0.5663	Remote Similarity	NPC45618
0.5663	Remote Similarity	NPC143851
0.5652	Remote Similarity	NPC475366
0.5652	Remote Similarity	NPC475497
0.5618	Remote Similarity	NPC254540
0.5595	Remote Similarity	NPC145038
0.5595	Remote Similarity	NPC56077
0.5595	Remote Similarity	NPC297987
0.5595	Remote Similarity	NPC281131
0.5595	Remote Similarity	NPC253662
0.5595	Remote Similarity	NPC179950
0.5595	Remote Similarity	NPC88789
0.5595	Remote Similarity	NPC259152
0.5595	Remote Similarity	NPC491374
0.5581	Remote Similarity	NPC191306
0.5556	Remote Similarity	NPC295613
0.5543	Remote Similarity	NPC115674
0.5542	Remote Similarity	NPC183357
0.5517	Remote Similarity	NPC601710
0.5479	Remote Similarity	NPC604569
0.5455	Remote Similarity	NPC88023
0.5455	Remote Similarity	NPC309025
0.5435	Remote Similarity	NPC210073
0.5426	Remote Similarity	NPC65711
0.5412	Remote Similarity	NPC282987
0.5412	Remote Similarity	NPC323593
0.5412	Remote Similarity	NPC203500
0.5393	Remote Similarity	NPC601586
0.5357	Remote Similarity	NPC473043
0.5357	Remote Similarity	NPC331652
0.5349	Remote Similarity	NPC24043
0.5349	Remote Similarity	NPC271692
0.5341	Remote Similarity	NPC486578
0.5326	Remote Similarity	NPC15358
0.5319	Remote Similarity	NPC284277
0.5294	Remote Similarity	NPC289667
0.5287	Remote Similarity	NPC27942
0.5281	Remote Similarity	NPC116458
0.5281	Remote Similarity	NPC246943
0.5275	Remote Similarity	NPC606546
0.527	Remote Similarity	NPC605047
0.5217	Remote Similarity	NPC480466
0.5208	Remote Similarity	NPC229409
0.5172	Remote Similarity	NPC22195
0.5172	Remote Similarity	NPC181712
0.5172	Remote Similarity	NPC21190
0.5172	Remote Similarity	NPC488080
0.5172	Remote Similarity	NPC169977
0.5169	Remote Similarity	NPC606560
0.5132	Remote Similarity	NPC473044
0.5116	Remote Similarity	NPC77672
0.5116	Remote Similarity	NPC133671
0.5116	Remote Similarity	NPC135391
0.5116	Remote Similarity	NPC78263
0.5116	Remote Similarity	NPC250069
0.5116	Remote Similarity	NPC238376
0.5114	Remote Similarity	NPC472459
0.5111	Remote Similarity	NPC150442
0.51	Remote Similarity	NPC244875
0.5067	Remote Similarity	NPC108406
0.5056	Remote Similarity	NPC20505
0.5056	Remote Similarity	NPC285197
0.5055	Remote Similarity	NPC203050
0.5055	Remote Similarity	NPC469931
0.5055	Remote Similarity	NPC488072
0.5055	Remote Similarity	NPC225434
0.5054	Remote Similarity	NPC603300

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC576285 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5507
0.1-0.2	3539
0.2-0.3	87
0.3-0.4	9
0.4-0.5	7
0.5-0.6	1
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
0.5833	Remote Similarity	NPD7472	Pre-clinical

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