NPASS Compound

Natural Product: NPC539697

Natural Product ID	NPC539697
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-3-methoxy-2-(4-methoxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-3-methoxy-2-(4-methoxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-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 58 61 0 0 0 0 0 0 0 0999 V2000 8.2284 3.4926 0.8793 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8504 3.7786 0.7370 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9118 2.7564 0.5813 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2941 1.4414 0.5611 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3904 0.3832 0.4076 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0523 0.6351 0.2668 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0506 -0.3791 0.0569 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2620 -1.6898 -0.2509 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5150 -2.2264 -0.4153 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1447 -2.2984 -1.6969 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1937 -2.5838 -0.4296 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3960 -3.7894 -0.7108 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9050 -2.1271 -0.2935 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2035 -2.9263 -0.4504 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0332 -4.2528 -0.7585 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4808 -2.3786 -0.2947 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6753 -1.0496 0.0145 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9022 -0.4591 0.1789 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1654 -1.0308 0.0780 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9345 -0.4979 -0.9492 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3602 0.7797 -0.7456 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3144 1.8360 -1.0530 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9320 3.0795 -0.7859 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9845 1.0152 0.6159 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1205 1.7913 0.5278 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2878 -0.3823 1.1729 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0185 -0.3354 2.3309 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9129 -1.0152 1.4028 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9967 -2.2537 1.9906 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5155 -0.2855 0.1622 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7564 -0.7851 0.0176 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -0.0018 0.1730 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6710 1.9889 0.2896 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5695 3.0101 0.4414 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3693 3.1107 1.9213 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5349 2.7533 0.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7825 4.4668 0.7504 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3447 1.1897 0.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7692 -0.6320 0.4287 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2223 -2.0847 -1.5498 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6666 -1.5432 -2.3295 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0794 -3.3291 -2.1157 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6367 -4.7917 -1.3669 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3200 -3.0371 -0.4257 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0511 -2.1034 -0.1705 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1932 0.9696 -1.4865 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1444 1.8243 -2.1504 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4003 1.7302 -0.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8987 3.0499 -1.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2341 1.4938 1.2761 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3996 2.0140 1.4593 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7487 -0.9641 0.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7331 -1.0463 2.2601 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3639 -0.3017 2.0536 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9493 -3.0043 1.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6652 0.7589 0.4051 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5947 2.2029 0.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2322 4.0336 0.4524 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 8 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 17 30 1 0 30 31 2 0 31 32 1 0 6 33 1 0 33 34 2 0 34 3 1 0 32 7 1 0 31 13 1 0 28 19 1 0 1 35 1 0 1 36 1 0 1 37 1 0 4 38 1 0 5 39 1 0 10 40 1 0 10 41 1 0 10 42 1 0 15 43 1 0 16 44 1 0 19 45 1 6 21 46 1 6 22 47 1 0 22 48 1 0 23 49 1 0 24 50 1 1 25 51 1 0 26 52 1 6 27 53 1 0 28 54 1 1 29 55 1 0 30 56 1 0 33 57 1 0 34 58 1 0 M END

Standard InCHIKey	ZRARLHYGVFWDGL-BPAZWDACSA-N
Standard InCHI	InChI=1S/C23H24O11/c1-30-11-5-3-10(4-6-11)21-22(31-2)18(27)16-13(25)7-12(8-14(16)33-21)32-23-20(29)19(28)17(26)15(9-24)34-23/h3-8,15,17,19-20,23-26,28-29H,9H2,1-2H3/t15-,17-,19+,20-,23-/m1/s1
SMILES	COC1=CC=C(C2=C(OC)C(=O)C3=C(O)C=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	476.13	Volume:	447.739 ? Van der Waals volume.
Dense:	1.063	LogP:	1.543 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.955 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.266 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	168.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.333	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.804	Fsp³:	0.348
MCE-18:	86.387 ? 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:	0.591	Fluc inhibitor:	0.41 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.93 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.902 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.09	Promiscuous compounds:	0.358

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.111	MDCK Permeability:	-5.194
Pgp-inhibitor:	0.047	Pgp-substrate:	0.414
PAMPA:	0.96 ? 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):	0.898
20% Bioavailability (F20%):	0.025	30% Bioavailability (F30%):	0.939
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.255
Plasma Protein Binding (PPB):	89.307%	Volume Distribution (VD):	-0.074
Fu:	10.587% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.967
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.759
BSEP inhibitor:	0.138

ADMET: Metabolism

CYP1A2-inhibitor:	0.237	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.964
HLM stability:	0.595 ? 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):

2.877

Half-life (T1/2):

3.027

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.109
Human Hepatotoxicity (H-HT):	0.613	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.908	Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.043	Skin Sensitization:	0.973
Carcinogencity:	0.516	Eye Corrosion:	0.0
Eye Irritation:	0.3	Respiratory Toxicity:	0.038
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.812
Hematotoxicity:	0.304	Drug-induced Nephrotoxicity:	0.615
Genotoxicity:	0.756	RPMI-8226 Immunitoxicity:	0.112
A549 Cytotoxicity:	0.206	Hek293 Cytotoxicity:	0.281
BCF:	0.465 ? 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:	3.23 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.635 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.856 ? 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
NPO55964	Carduus pycnocephalus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO47979	Asplenium marinum	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO50273	Asplenium platyneuron	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC539697 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	20635
0.1-0.2	24804
0.2-0.3	2968
0.3-0.4	848
0.4-0.5	358
0.5-0.6	107
0.6-0.7	78
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8971	High Similarity	NPC289667
0.8451	Intermediate Similarity	NPC84362
0.8056	Intermediate Similarity	NPC297987
0.7808	Intermediate Similarity	NPC95090
0.7808	Intermediate Similarity	NPC27408
0.7808	Intermediate Similarity	NPC136042
0.76	Intermediate Similarity	NPC472459
0.7532	Intermediate Similarity	NPC116458
0.7532	Intermediate Similarity	NPC246943
0.7468	Intermediate Similarity	NPC251417
0.7308	Intermediate Similarity	NPC605784
0.7229	Intermediate Similarity	NPC64425
0.7179	Intermediate Similarity	NPC22832
0.7105	Intermediate Similarity	NPC64305
0.7051	Intermediate Similarity	NPC611303
0.6962	Remote Similarity	NPC243930
0.6962	Remote Similarity	NPC21666
0.6962	Remote Similarity	NPC486578
0.6835	Remote Similarity	NPC285197
0.6795	Remote Similarity	NPC46420
0.6753	Remote Similarity	NPC249281
0.675	Remote Similarity	NPC148710
0.675	Remote Similarity	NPC609478
0.6667	Remote Similarity	NPC277532
0.6667	Remote Similarity	NPC277205
0.6667	Remote Similarity	NPC37919
0.6667	Remote Similarity	NPC262094
0.6667	Remote Similarity	NPC35119
0.6667	Remote Similarity	NPC189142
0.6667	Remote Similarity	NPC77660
0.6667	Remote Similarity	NPC607707
0.6632	Remote Similarity	NPC295625
0.6582	Remote Similarity	NPC24043
0.6582	Remote Similarity	NPC271692
0.6559	Remote Similarity	NPC470715
0.6543	Remote Similarity	NPC120099
0.6538	Remote Similarity	NPC261866
0.6538	Remote Similarity	NPC39360
0.6538	Remote Similarity	NPC29763
0.6538	Remote Similarity	NPC210003
0.6477	Remote Similarity	NPC32641
0.6477	Remote Similarity	NPC256188
0.6463	Remote Similarity	NPC311830
0.6456	Remote Similarity	NPC158674
0.6456	Remote Similarity	NPC323593
0.6456	Remote Similarity	NPC203500
0.6421	Remote Similarity	NPC470716
0.642	Remote Similarity	NPC488071
0.6383	Remote Similarity	NPC164704
0.6375	Remote Similarity	NPC186807
0.6375	Remote Similarity	NPC181712
0.6375	Remote Similarity	NPC73511
0.6375	Remote Similarity	NPC603655
0.6329	Remote Similarity	NPC58053
0.6329	Remote Similarity	NPC77672
0.6329	Remote Similarity	NPC133671
0.6329	Remote Similarity	NPC135391
0.6329	Remote Similarity	NPC78263
0.6329	Remote Similarity	NPC250069
0.6327	Remote Similarity	NPC470717
0.6304	Remote Similarity	NPC14187
0.6263	Remote Similarity	NPC470720
0.625	Remote Similarity	NPC240306
0.625	Remote Similarity	NPC234739
0.6222	Remote Similarity	NPC5319
0.622	Remote Similarity	NPC60735
0.622	Remote Similarity	NPC26230
0.6211	Remote Similarity	NPC25523
0.619	Remote Similarity	NPC276377
0.619	Remote Similarity	NPC601586
0.6173	Remote Similarity	NPC488080
0.6173	Remote Similarity	NPC169977
0.6162	Remote Similarity	NPC470719
0.6145	Remote Similarity	NPC601144
0.6111	Remote Similarity	NPC606657
0.6098	Remote Similarity	NPC42773
0.6098	Remote Similarity	NPC45522
0.6098	Remote Similarity	NPC325555
0.6098	Remote Similarity	NPC226304
0.6049	Remote Similarity	NPC145038
0.6049	Remote Similarity	NPC56077
0.6049	Remote Similarity	NPC281131
0.6049	Remote Similarity	NPC253662
0.6049	Remote Similarity	NPC179950
0.6049	Remote Similarity	NPC88789
0.6049	Remote Similarity	NPC491374
0.6042	Remote Similarity	NPC480441
0.6024	Remote Similarity	NPC168584
0.6024	Remote Similarity	NPC307938
0.6023	Remote Similarity	NPC150164
0.6	Remote Similarity	NPC203050
0.6	Remote Similarity	NPC488072
0.6	Remote Similarity	NPC225434
0.5926	Remote Similarity	NPC19388
0.5926	Remote Similarity	NPC240431
0.5926	Remote Similarity	NPC55786
0.5904	Remote Similarity	NPC60966
0.5904	Remote Similarity	NPC599850
0.5854	Remote Similarity	NPC197896
0.5854	Remote Similarity	NPC313163
0.5844	Remote Similarity	NPC191154
0.5806	Remote Similarity	NPC475382
0.5806	Remote Similarity	NPC76831
0.5795	Remote Similarity	NPC480466
0.5783	Remote Similarity	NPC22195
0.5783	Remote Similarity	NPC21190
0.5778	Remote Similarity	NPC186816
0.5769	Remote Similarity	NPC134819
0.5765	Remote Similarity	NPC101026
0.5765	Remote Similarity	NPC80188
0.5765	Remote Similarity	NPC488077
0.5765	Remote Similarity	NPC605067
0.5761	Remote Similarity	NPC72016
0.5732	Remote Similarity	NPC143851
0.5729	Remote Similarity	NPC121703
0.5714	Remote Similarity	NPC103904
0.5699	Remote Similarity	NPC486577
0.5698	Remote Similarity	NPC220169
0.5694	Remote Similarity	NPC270620
0.5684	Remote Similarity	NPC135358
0.5682	Remote Similarity	NPC480463
0.5667	Remote Similarity	NPC22062
0.5667	Remote Similarity	NPC473634
0.5667	Remote Similarity	NPC138811
0.5663	Remote Similarity	NPC8573
0.5647	Remote Similarity	NPC80140
0.5647	Remote Similarity	NPC609451
0.5634	Remote Similarity	NPC146679
0.5616	Remote Similarity	NPC236769
0.5604	Remote Similarity	NPC131745
0.5595	Remote Similarity	NPC45638
0.5556	Remote Similarity	NPC288084
0.5556	Remote Similarity	NPC275454
0.5543	Remote Similarity	NPC46202
0.5542	Remote Similarity	NPC19709
0.5542	Remote Similarity	NPC238376
0.5529	Remote Similarity	NPC27942
0.5529	Remote Similarity	NPC117260
0.5529	Remote Similarity	NPC201292
0.5506	Remote Similarity	NPC8856
0.5506	Remote Similarity	NPC473682
0.5479	Remote Similarity	NPC153758
0.5476	Remote Similarity	NPC93337
0.5476	Remote Similarity	NPC168822
0.5465	Remote Similarity	NPC219904
0.5465	Remote Similarity	NPC479402
0.5437	Remote Similarity	NPC470713
0.5426	Remote Similarity	NPC473623
0.5422	Remote Similarity	NPC473043
0.5422	Remote Similarity	NPC45165
0.5422	Remote Similarity	NPC331652
0.5417	Remote Similarity	NPC110070
0.5417	Remote Similarity	NPC188871
0.5412	Remote Similarity	NPC27640
0.5412	Remote Similarity	NPC105025
0.5412	Remote Similarity	NPC610763
0.5402	Remote Similarity	NPC284960
0.54	Remote Similarity	NPC470712
0.5368	Remote Similarity	NPC142142
0.5368	Remote Similarity	NPC488089
0.5357	Remote Similarity	NPC44558
0.5357	Remote Similarity	NPC108831
0.5357	Remote Similarity	NPC182634
0.5349	Remote Similarity	NPC182045
0.5349	Remote Similarity	NPC21100
0.5341	Remote Similarity	NPC88023
0.5341	Remote Similarity	NPC206123
0.5341	Remote Similarity	NPC309025
0.5333	Remote Similarity	NPC278419
0.5333	Remote Similarity	NPC179198
0.5315	Remote Similarity	NPC223860
0.5301	Remote Similarity	NPC67037
0.5301	Remote Similarity	NPC255615
0.53	Remote Similarity	NPC48984
0.5287	Remote Similarity	NPC191306
0.5281	Remote Similarity	NPC170052
0.5281	Remote Similarity	NPC190003
0.5281	Remote Similarity	NPC135846
0.5281	Remote Similarity	NPC267254
0.5275	Remote Similarity	NPC139320
0.5263	Remote Similarity	NPC124155
0.5263	Remote Similarity	NPC209296
0.5256	Remote Similarity	NPC99671
0.5238	Remote Similarity	NPC111929
0.5238	Remote Similarity	NPC320283
0.5238	Remote Similarity	NPC135345
0.5238	Remote Similarity	NPC41121
0.5238	Remote Similarity	NPC160515
0.5233	Remote Similarity	NPC245014
0.5233	Remote Similarity	NPC58716
0.5233	Remote Similarity	NPC600680
0.5227	Remote Similarity	NPC229729
0.5227	Remote Similarity	NPC608742
0.5213	Remote Similarity	NPC488073
0.5205	Remote Similarity	NPC59951
0.5205	Remote Similarity	NPC76376
0.52	Remote Similarity	NPC206604
0.5196	Remote Similarity	NPC311850
0.5181	Remote Similarity	NPC34531
0.5176	Remote Similarity	NPC210042

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC539697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5026
0.1-0.2	4018
0.2-0.3	89
0.3-0.4	9
0.4-0.5	4
0.5-0.6	3
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
0.6222	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5408	Remote Similarity	NPD7808	Phase 3
0.5312	Remote Similarity	NPD7251	Phase 2
0.5263	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