NPASS Compound

Natural Product: NPC552720

Natural Product ID	NPC552720
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2~{S},3~{S},4~{R},5~{R},6~{R})-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-chromen-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methoxy]-5-hydroxy-2-methyl-4-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] acetate
IUPAC Name	[(2~{S},3~{S},4~{R},5~{R},6~{R})-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-chromen-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methoxy]-5-hydroxy-2-methyl-4-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] acetate
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 101106 0 0 0 0 0 0 0 0999 V2000 -10.7814 -4.4568 -0.1532 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3645 -3.1966 -0.6025 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1500 -2.6296 -0.2304 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2881 -3.2930 0.6143 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0805 -2.7594 0.9990 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1971 -3.4215 1.8550 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7125 -1.5186 0.5276 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5092 -0.9777 0.8967 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7094 -1.5696 1.6661 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1727 0.2832 0.3899 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9224 0.8039 0.7805 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7398 0.3197 0.1680 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9245 -0.1804 1.1871 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5844 0.1089 1.0325 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1668 -0.4693 2.2080 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5124 -0.2668 2.1968 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2070 -0.8382 1.1268 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1132 -1.7766 1.6529 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4642 -2.6742 0.6419 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2651 -3.4468 0.1616 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1928 -1.9543 -0.4724 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5482 -2.3782 -0.5205 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0803 -3.0627 -1.5937 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5128 -3.5058 -1.6307 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3158 -3.3163 -2.5710 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1479 -0.4817 -0.3594 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3625 -0.0526 0.2399 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1225 0.7092 -0.6343 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3973 0.2995 -0.8409 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3426 0.5783 0.0853 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2450 -0.6367 0.3071 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8760 1.1212 1.4007 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4584 0.0475 2.1843 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7293 2.0830 1.2861 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6918 1.7459 2.1552 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1762 2.1511 -0.1180 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1063 2.8150 -0.9357 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9854 0.1446 0.3125 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1199 0.6904 -0.6467 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4432 1.6330 1.0669 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2013 2.0386 2.1899 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0696 2.1628 -0.1924 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5648 3.4431 -0.0424 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0500 1.1849 -0.7929 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3356 0.4012 -1.7664 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0199 0.9382 -0.4304 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7821 2.2783 -1.0116 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8407 3.1611 -0.5780 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6470 4.4026 -1.1865 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4177 4.7792 -2.2639 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2305 6.0229 -2.8814 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3728 3.8895 -2.7064 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1504 4.2751 -3.7969 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5492 2.6624 -2.0893 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1748 0.3421 -0.7473 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5465 -0.8143 -0.3235 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7577 -1.3979 -0.6829 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8691 -4.5742 -0.4078 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1963 -5.2833 -0.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6892 -4.5335 0.9333 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5841 -4.2625 0.9784 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5214 -4.2467 2.3696 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0574 -0.6106 -0.4177 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2542 -0.3512 0.1066 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0461 -1.5782 2.2764 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2425 -0.0366 3.1377 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4604 -1.3534 0.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1737 -3.3957 1.0883 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4294 -3.4245 0.9114 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9254 -3.0530 -0.8157 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4896 -4.5296 0.0089 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7145 -2.2721 -1.4213 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9684 -3.0447 -2.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5245 -4.6182 -1.6982 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0135 -3.1645 -0.7001 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1944 -0.0507 -1.4034 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6134 0.8045 -1.6388 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0345 1.3577 -0.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8219 -1.3420 1.0503 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4960 -1.1069 -0.6470 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1746 -0.2362 0.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7052 1.6160 1.9433 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8373 0.0545 3.0956 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0497 3.1169 1.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0158 1.2701 2.9739 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1952 2.6253 -0.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5759 3.5391 -0.4583 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3201 0.9423 1.0245 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6289 1.2553 -1.3001 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5890 1.9603 1.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3271 3.0220 2.1655 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2184 2.2608 -0.9312 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6365 3.9425 -0.8974 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7539 1.7414 -1.4242 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9991 -0.0239 -2.3694 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2205 2.9354 0.2578 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8803 5.0779 -0.8041 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9408 6.8027 -2.2724 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6766 5.1562 -3.7857 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3089 1.9867 -2.4628 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3782 -0.8164 -1.3462 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 5 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 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 19 20 1 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 2 0 21 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 26 38 1 0 38 39 1 0 14 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 10 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 50 52 1 0 52 53 1 0 52 54 2 0 46 55 1 0 55 56 1 0 56 57 2 0 57 3 1 0 56 7 1 0 44 12 1 0 54 47 1 0 38 17 1 0 36 28 1 0 1 58 1 0 1 59 1 0 1 60 1 0 4 61 1 0 6 62 1 0 12 63 1 6 14 64 1 6 15 65 1 0 15 66 1 0 17 67 1 6 19 68 1 1 20 69 1 0 20 70 1 0 20 71 1 0 21 72 1 6 24 73 1 0 24 74 1 0 24 75 1 0 26 76 1 6 28 77 1 6 30 78 1 6 31 79 1 0 31 80 1 0 31 81 1 0 32 82 1 1 33 83 1 0 34 84 1 1 35 85 1 0 36 86 1 1 37 87 1 0 38 88 1 1 39 89 1 0 40 90 1 1 41 91 1 0 42 92 1 6 43 93 1 0 44 94 1 6 45 95 1 0 48 96 1 0 49 97 1 0 51 98 1 0 53 99 1 0 54100 1 0 57101 1 0 M END

Standard InCHIKey	SNWSDJIWOIJZFI-IWNNWYHFSA-N
Standard InCHI	InChI=1S/C36H44O21/c1-11-22(41)25(44)27(46)35(51-11)57-33-29(48)34(52-12(2)30(33)53-13(3)37)50-10-20-23(42)26(45)28(47)36(55-20)56-32-24(43)21-18(40)8-15(49-4)9-19(21)54-31(32)14-5-6-16(38)17(39)7-14/h5-9,11-12,20,22-23,25-30,33-36,38-42,44-48H,10H2,1-4H3/t11-,12+,20-,22+,23+,25+,26+,27-,28-,29-,30+,33-,34-,35+,36+/m1/s1
SMILES	COC1=CC(O)=C2C(=O)C(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](OC(C)=O)[C@H](O[C@@H]5O[C@H](C)[C@H](O)[C@H](O)[C@H]5O)[C@H]4O)[C@H](O)[C@H](O)[C@H]3O)=C(C3=CC=C(O)C(O)=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25243	Rhamnus saxatilis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25243	Rhamnus saxatilis	Species	Rhamnaceae	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 NPC552720 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	18164
0.1-0.2	27848
0.2-0.3	3010
0.3-0.4	422
0.4-0.5	273
0.5-0.6	102
0.6-0.7	36
0.7-0.8	1
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
0.7071	Intermediate Similarity	NPC186816
0.6989	Remote Similarity	NPC271692
0.6931	Remote Similarity	NPC470443
0.6667	Remote Similarity	NPC126784
0.6667	Remote Similarity	NPC241423
0.6634	Remote Similarity	NPC203259
0.6634	Remote Similarity	NPC33054
0.6634	Remote Similarity	NPC176740
0.6634	Remote Similarity	NPC471725
0.6634	Remote Similarity	NPC134532
0.6634	Remote Similarity	NPC602582
0.6606	Remote Similarity	NPC480441
0.6535	Remote Similarity	NPC67105
0.6471	Remote Similarity	NPC210073
0.6449	Remote Similarity	NPC470446
0.6415	Remote Similarity	NPC473073
0.6321	Remote Similarity	NPC142142
0.6321	Remote Similarity	NPC486577
0.6289	Remote Similarity	NPC46420
0.62	Remote Similarity	NPC605784
0.6186	Remote Similarity	NPC158674
0.6091	Remote Similarity	NPC14187
0.6075	Remote Similarity	NPC473327
0.6071	Remote Similarity	NPC292019
0.6071	Remote Similarity	NPC202908
0.6058	Remote Similarity	NPC173582
0.6058	Remote Similarity	NPC265885
0.6058	Remote Similarity	NPC181465
0.6058	Remote Similarity	NPC215710
0.6058	Remote Similarity	NPC473438
0.6058	Remote Similarity	NPC253788
0.6055	Remote Similarity	NPC470445
0.6018	Remote Similarity	NPC25523
0.6	Remote Similarity	NPC22062
0.6	Remote Similarity	NPC473634
0.6	Remote Similarity	NPC138811
0.6	Remote Similarity	NPC611303
0.5981	Remote Similarity	NPC483415
0.5963	Remote Similarity	NPC476472
0.5963	Remote Similarity	NPC294815
0.5963	Remote Similarity	NPC16194
0.5963	Remote Similarity	NPC471669
0.5943	Remote Similarity	NPC473571
0.5943	Remote Similarity	NPC110941
0.5926	Remote Similarity	NPC209296
0.5926	Remote Similarity	NPC606657
0.5922	Remote Similarity	NPC116864
0.5922	Remote Similarity	NPC244776
0.5918	Remote Similarity	NPC249281
0.5905	Remote Similarity	NPC44931
0.5905	Remote Similarity	NPC67326
0.5905	Remote Similarity	NPC39834
0.5905	Remote Similarity	NPC227508
0.5888	Remote Similarity	NPC488073
0.5888	Remote Similarity	NPC488074
0.5859	Remote Similarity	NPC136042
0.5849	Remote Similarity	NPC65563
0.5849	Remote Similarity	NPC470949
0.5849	Remote Similarity	NPC156869
0.5841	Remote Similarity	NPC470451
0.5825	Remote Similarity	NPC276377
0.5818	Remote Similarity	NPC89127
0.58	Remote Similarity	NPC84362
0.58	Remote Similarity	NPC27640
0.578	Remote Similarity	NPC483416
0.5766	Remote Similarity	NPC101636
0.5766	Remote Similarity	NPC470449
0.5752	Remote Similarity	NPC121703
0.5727	Remote Similarity	NPC488089
0.5688	Remote Similarity	NPC483414
0.5636	Remote Similarity	NPC122467
0.5636	Remote Similarity	NPC72016
0.5619	Remote Similarity	NPC265115
0.5596	Remote Similarity	NPC240306
0.5588	Remote Similarity	NPC59534
0.5577	Remote Similarity	NPC116458
0.5577	Remote Similarity	NPC246943
0.5565	Remote Similarity	NPC189564
0.5556	Remote Similarity	NPC150164
0.5556	Remote Similarity	NPC605592
0.5495	Remote Similarity	NPC32641
0.5495	Remote Similarity	NPC256188
0.5492	Remote Similarity	NPC209550
0.549	Remote Similarity	NPC305811
0.5446	Remote Similarity	NPC127546
0.5446	Remote Similarity	NPC57625
0.5446	Remote Similarity	NPC173637
0.5446	Remote Similarity	NPC317489
0.5446	Remote Similarity	NPC238376
0.5446	Remote Similarity	NPC223424
0.5446	Remote Similarity	NPC600591
0.5421	Remote Similarity	NPC251417
0.5405	Remote Similarity	NPC65711
0.5398	Remote Similarity	NPC470447
0.5391	Remote Similarity	NPC470455
0.537	Remote Similarity	NPC471079
0.5366	Remote Similarity	NPC138990
0.5366	Remote Similarity	NPC241781
0.5357	Remote Similarity	NPC35119
0.5351	Remote Similarity	NPC298171
0.5323	Remote Similarity	NPC175429
0.5315	Remote Similarity	NPC153755
0.5304	Remote Similarity	NPC135358
0.5294	Remote Similarity	NPC19709
0.5294	Remote Similarity	NPC277532
0.5273	Remote Similarity	NPC303913
0.5263	Remote Similarity	NPC483413
0.5263	Remote Similarity	NPC483412
0.5254	Remote Similarity	NPC173837
0.5243	Remote Similarity	NPC297987
0.5229	Remote Similarity	NPC480466
0.5225	Remote Similarity	NPC204693
0.5221	Remote Similarity	NPC229409
0.5214	Remote Similarity	NPC203145
0.5214	Remote Similarity	NPC11468
0.5203	Remote Similarity	NPC156785
0.5182	Remote Similarity	NPC471748
0.5182	Remote Similarity	NPC275454
0.5179	Remote Similarity	NPC64425
0.5154	Remote Similarity	NPC223860
0.5147	Remote Similarity	NPC482520
0.5147	Remote Similarity	NPC482519
0.5146	Remote Similarity	NPC289667
0.5138	Remote Similarity	NPC254540
0.5133	Remote Similarity	NPC12013
0.5133	Remote Similarity	NPC11432
0.5133	Remote Similarity	NPC477613
0.5094	Remote Similarity	NPC175107
0.5094	Remote Similarity	NPC488071
0.5091	Remote Similarity	NPC609888
0.5088	Remote Similarity	NPC37668
0.5088	Remote Similarity	NPC473623
0.5085	Remote Similarity	NPC89052
0.5083	Remote Similarity	NPC303694
0.5081	Remote Similarity	NPC162394
0.5046	Remote Similarity	NPC95866
0.5043	Remote Similarity	NPC223426
0.5041	Remote Similarity	NPC488086
0.5038	Remote Similarity	NPC72554

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC552720 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5375
0.1-0.2	3715
0.2-0.3	51
0.3-0.4	3
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
0.7-0.8	1
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
0.74	Intermediate Similarity	NPD7251	Phase 2
0.6634	Remote Similarity	NPD6797	Phase 2
0.633	Remote Similarity	NPD7808	Phase 3
0.5926	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