NPASS Compound

Natural Product: NPC519289

Natural Product ID	NPC519289
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,6-dihydroxy-7-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-[4-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxyphenyl]chromen-4-one
IUPAC Name	5,6-dihydroxy-7-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-[4-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxyphenyl]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 71 75 0 0 0 0 0 0 0 0999 V2000 8.3024 1.3682 -2.5041 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8233 0.0128 -2.0214 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8113 -0.0491 -0.6410 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9988 -1.1513 -0.2675 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7234 -1.0327 -0.8291 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5440 -0.7429 -0.2004 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4973 -0.4779 1.1341 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2569 -0.1901 1.7205 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0833 -0.1617 1.0134 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7972 0.1512 1.6264 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6457 0.4873 2.9410 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5805 0.7840 3.5104 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7363 1.0922 4.7058 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 0.7326 2.6984 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9506 1.0022 3.1400 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1480 1.3484 4.4657 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0325 0.9269 2.2504 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2751 1.2163 2.7824 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9068 0.5928 0.9357 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8912 0.4984 0.0290 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2291 0.7454 0.1376 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8867 -0.5059 0.0625 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2438 -0.4083 0.3293 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8233 -1.7901 0.0188 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9602 0.5763 -0.5353 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1245 0.0205 -1.8113 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2217 1.8897 -0.6681 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8529 2.5854 -1.7200 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7933 1.5294 -1.0491 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0057 2.6443 -1.2277 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5801 0.3206 0.5185 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5047 0.3894 1.3774 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2856 0.1154 0.8946 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1652 -0.4378 -0.3511 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3780 -0.7218 -0.9380 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6960 -2.4220 -0.6823 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7874 -3.1943 -1.4061 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9484 -2.1333 -1.4396 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9672 -1.7441 -0.5666 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7509 -1.0786 -2.5292 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1356 -1.6910 -3.5940 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6915 1.6917 -3.3621 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3529 1.3263 -2.8583 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1731 2.1532 -1.7100 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7857 -0.1269 -2.3779 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0127 -1.1216 0.8514 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3663 -0.4716 1.7842 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2493 0.0140 2.7720 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5131 0.5314 3.5871 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1038 1.3649 4.8176 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7892 0.6675 3.4371 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5242 1.2866 1.0280 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4518 -0.2625 1.4272 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4059 -2.5524 0.7183 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4452 -2.0547 -0.9913 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9215 -1.8026 0.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9553 0.7777 -0.1009 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7730 -0.7218 -1.7790 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2239 2.4588 0.2580 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8366 2.5420 -1.5533 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8430 0.8701 -1.9549 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5802 2.6894 -2.1230 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4426 0.0496 -0.5223 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2277 -0.4114 -0.8899 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3924 -0.9305 -2.0021 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9976 -3.0327 0.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2319 -3.6690 -0.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2851 -3.0569 -1.9679 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4369 -2.5271 -0.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7359 -0.6509 -2.7415 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2602 -1.1376 -4.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 15 17 1 0 17 18 1 0 17 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 19 31 1 0 31 32 2 0 32 33 1 0 9 34 1 0 34 35 2 0 4 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 40 2 1 0 35 6 1 0 33 10 1 0 32 14 1 0 29 21 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 6 4 46 1 1 7 47 1 0 8 48 1 0 11 49 1 0 16 50 1 0 18 51 1 0 21 52 1 1 23 53 1 1 24 54 1 0 24 55 1 0 24 56 1 0 25 57 1 1 26 58 1 0 27 59 1 1 28 60 1 0 29 61 1 6 30 62 1 0 31 63 1 0 34 64 1 0 35 65 1 0 36 66 1 1 37 67 1 0 38 68 1 6 39 69 1 0 40 70 1 6 41 71 1 0 M END

Standard InCHIKey	PATAJOYWUAAQGX-JUSLCMBCSA-N
Standard InCHI	InChI=1S/C27H30O14/c1-9-18(29)22(33)24(35)26(37-9)39-12-5-3-11(4-6-12)14-7-13(28)17-15(40-14)8-16(20(31)21(17)32)41-27-25(36)23(34)19(30)10(2)38-27/h3-10,18-19,22-27,29-36H,1-2H3/t9-,10+,18-,19-,22+,23-,24-,25+,26-,27-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC2=CC=C(C3=CC(=O)C4=C(O)C(O)=C(O[C@@H]5O[C@H](C)[C@H](O)[C@H](O)[C@H]5O)C=C4O3)C=C2)[C@@H](O)[C@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.16	Volume:	534.737 ? Van der Waals volume.
Dense:	1.081	LogP:	1.462 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.763 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.6 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	30.0
TPSA:	228.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.175	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.662	Fsp³:	0.444
MCE-18:	119.436 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.632	Fluc inhibitor:	0.332 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.89 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.699 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.241	Promiscuous compounds:	0.43

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.338	MDCK Permeability:	-5.18
Pgp-inhibitor:	0.0	Pgp-substrate:	0.798
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):	0.61
20% Bioavailability (F20%):	0.51	30% Bioavailability (F30%):	0.954
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.463
Plasma Protein Binding (PPB):	85.695%	Volume Distribution (VD):	-0.032
Fu:	11.779% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.494
BSEP inhibitor:	0.006

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.775
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.969
HLM stability:	0.03 ? 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):

1.773

Half-life (T1/2):

5.714

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.227
Human Hepatotoxicity (H-HT):	0.489	Drug-induced Liver Injury (DILI):	0.985
AMES Toxicity:	0.962	Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.044	Skin Sensitization:	0.987
Carcinogencity:	0.06	Eye Corrosion:	0.0
Eye Irritation:	0.122	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.968
Hematotoxicity:	0.276	Drug-induced Nephrotoxicity:	0.777
Genotoxicity:	0.903	RPMI-8226 Immunitoxicity:	0.216
A549 Cytotoxicity:	0.588	Hek293 Cytotoxicity:	0.418
BCF:	0.384 ? 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:	3.081 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.627 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.808 ? 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
NPO50863	Atraphaxis pyrifolia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38398586]
NPO50863	Atraphaxis pyrifolia	Species	Polygonaceae	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 NPC519289 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	18028
0.1-0.2	28355
0.2-0.3	2523
0.3-0.4	645
0.4-0.5	217
0.5-0.6	64
0.6-0.7	16
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	Natural Product ID
0.7297	Intermediate Similarity	NPC45618
0.72	Intermediate Similarity	NPC146792
0.6883	Remote Similarity	NPC58716
0.6711	Remote Similarity	NPC331652
0.641	Remote Similarity	NPC58053
0.641	Remote Similarity	NPC19709
0.6282	Remote Similarity	NPC473043
0.625	Remote Similarity	NPC186807
0.6207	Remote Similarity	NPC204693
0.6176	Remote Similarity	NPC57030
0.6125	Remote Similarity	NPC95090
0.6125	Remote Similarity	NPC27408
0.6092	Remote Similarity	NPC22062
0.6092	Remote Similarity	NPC473634
0.6092	Remote Similarity	NPC138811
0.6049	Remote Similarity	NPC181712
0.6	Remote Similarity	NPC211594
0.6	Remote Similarity	NPC143851
0.5904	Remote Similarity	NPC237435
0.5833	Remote Similarity	NPC43211
0.5833	Remote Similarity	NPC605067
0.573	Remote Similarity	NPC3583
0.5652	Remote Similarity	NPC209296
0.5647	Remote Similarity	NPC22832
0.5618	Remote Similarity	NPC44931
0.561	Remote Similarity	NPC39360
0.561	Remote Similarity	NPC29763
0.561	Remote Similarity	NPC210003
0.5595	Remote Similarity	NPC27942
0.5532	Remote Similarity	NPC475382
0.5529	Remote Similarity	NPC609451
0.5529	Remote Similarity	NPC611303
0.5488	Remote Similarity	NPC160515
0.5476	Remote Similarity	NPC245014
0.5476	Remote Similarity	NPC84265
0.5476	Remote Similarity	NPC105025
0.5465	Remote Similarity	NPC243930
0.5465	Remote Similarity	NPC601144
0.5455	Remote Similarity	NPC477848
0.5422	Remote Similarity	NPC261866
0.5402	Remote Similarity	NPC607707
0.5393	Remote Similarity	NPC251417
0.5385	Remote Similarity	NPC210073
0.5357	Remote Similarity	NPC93337
0.5357	Remote Similarity	NPC189142
0.5357	Remote Similarity	NPC77660
0.5352	Remote Similarity	NPC275722
0.5349	Remote Similarity	NPC191306
0.5342	Remote Similarity	NPC212678
0.5341	Remote Similarity	NPC190003
0.5333	Remote Similarity	NPC603300
0.5326	Remote Similarity	NPC257566
0.5319	Remote Similarity	NPC473623
0.5319	Remote Similarity	NPC483707
0.5287	Remote Similarity	NPC115760
0.5287	Remote Similarity	NPC181616
0.5287	Remote Similarity	NPC606560
0.5281	Remote Similarity	NPC172807
0.5278	Remote Similarity	NPC198826
0.527	Remote Similarity	NPC283600
0.5269	Remote Similarity	NPC46202
0.5263	Remote Similarity	NPC485299
0.5263	Remote Similarity	NPC488089
0.5238	Remote Similarity	NPC249281
0.5238	Remote Similarity	NPC108831
0.5238	Remote Similarity	NPC238376
0.5238	Remote Similarity	NPC182634
0.5233	Remote Similarity	NPC201292
0.5227	Remote Similarity	NPC311830
0.5227	Remote Similarity	NPC602805
0.5217	Remote Similarity	NPC65003
0.5155	Remote Similarity	NPC298171
0.5152	Remote Similarity	NPC11468
0.5122	Remote Similarity	NPC25547
0.5116	Remote Similarity	NPC46420
0.5116	Remote Similarity	NPC271692
0.5116	Remote Similarity	NPC27640
0.5116	Remote Similarity	NPC45638
0.5068	Remote Similarity	NPC145379
0.5059	Remote Similarity	NPC289667
0.5055	Remote Similarity	NPC254540
0.5053	Remote Similarity	NPC470443

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC519289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4604
0.1-0.2	4463
0.2-0.3	71
0.3-0.4	4
0.4-0.5	6
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
0.5904	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5652	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