NPASS Compound

Natural Product: NPC527002

Natural Product ID	NPC527002
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	38784-81-5
IUPAC Name	2-(3,4-dihydroxyphenyl)-5-hydroxy-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-7-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-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 73 77 0 0 0 0 0 0 0 0999 V2000 7.2702 2.2841 1.4127 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3895 1.6407 0.0208 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1454 1.7498 -0.5444 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5754 0.4904 -0.8577 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3262 0.6614 -1.4260 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1407 0.3197 -0.8033 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0329 -0.1894 0.4568 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7994 -0.4934 0.9727 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6646 -1.0130 2.2528 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6247 -0.3017 0.2520 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5994 -0.5863 0.7192 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6973 -1.0627 1.8934 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8012 -0.3823 -0.0347 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9060 -0.7166 0.5397 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9793 -0.6353 1.2517 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7588 -0.9952 2.6512 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6640 -0.2744 3.3783 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7860 -0.8492 4.7777 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7131 -0.0648 5.4557 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9691 0.0149 2.7284 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9807 -0.0802 3.7128 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3588 -0.8856 1.5986 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2841 -1.8745 1.9923 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1728 -1.5005 0.9040 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3415 -1.7534 -0.4303 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6030 0.1395 -1.2929 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6538 0.4364 -2.2383 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9634 0.6402 -1.9551 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9256 0.8514 -2.9495 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5718 0.8602 -4.2665 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4860 1.0640 -5.2842 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2463 0.6572 -4.5673 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8195 0.6564 -5.8975 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3163 0.4527 -3.5941 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3702 0.3998 -1.7040 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7251 0.2150 -1.0249 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9565 0.5167 -1.5356 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5568 -0.1863 -1.7865 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9854 -1.2859 -2.4238 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7946 -0.5423 -1.0267 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6577 -1.8952 -0.6697 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8446 0.2241 0.2643 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1731 0.2000 0.7198 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7904 1.5129 2.0899 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5854 3.1579 1.3218 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2605 2.5882 1.7754 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1760 2.1964 -0.5271 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5113 -0.0943 0.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9032 -0.3512 1.0564 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4598 -1.1329 2.8753 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3452 0.4267 1.3777 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1655 0.7394 3.5426 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9994 -1.9141 4.8129 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8039 -0.6567 5.2837 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4596 0.8780 5.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0458 1.0894 2.3862 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1302 -1.0378 3.8791 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8873 -0.2783 0.8327 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1699 -1.7550 1.5710 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9990 -2.4935 1.4288 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4452 -2.0032 -0.7938 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3442 0.6897 -0.9552 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9600 1.0106 -2.6827 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6868 2.0521 -5.5120 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5105 0.6478 -6.6127 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2869 0.2966 -3.8762 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0387 0.9190 -2.5385 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8892 0.5154 -2.5988 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9648 -1.2111 -3.4059 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7227 -0.4048 -1.6337 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2233 -2.5029 -1.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2374 -0.2726 1.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7817 0.4817 -0.0128 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 1 0 8 10 2 0 10 11 1 0 11 12 2 0 11 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 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 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 2 0 26 35 1 0 35 36 1 0 36 37 2 0 4 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 42 2 1 0 37 6 1 0 36 10 1 0 24 15 1 0 34 27 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 6 4 48 1 1 7 49 1 0 9 50 1 0 15 51 1 1 17 52 1 1 18 53 1 0 18 54 1 0 19 55 1 0 20 56 1 6 21 57 1 0 22 58 1 6 23 59 1 0 24 60 1 1 25 61 1 0 28 62 1 0 29 63 1 0 31 64 1 0 33 65 1 0 34 66 1 0 37 67 1 0 38 68 1 6 39 69 1 0 40 70 1 6 41 71 1 0 42 72 1 1 43 73 1 0 M END

Standard InCHIKey	OTUCXMIQUNROBJ-KFGMVVDJSA-N
Standard InCHI	InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(39-8)40-10-5-13(31)16-14(6-10)41-24(9-2-3-11(29)12(30)4-9)25(19(16)34)43-27-23(38)21(36)18(33)15(7-28)42-27/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18-,20+,21-,22+,23+,26-,27-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)=C(C4=CC=C(O)C(O)=C4)OC3=C2)[C@H](O)[C@H](O)[C@H]1O

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
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[16180811]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	branch	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39355945]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23510	Vicia faba	Species	Fabaceae	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 NPC527002 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	22870
0.1-0.2	23360
0.2-0.3	2460
0.3-0.4	625
0.4-0.5	269
0.5-0.6	80
0.6-0.7	77
0.7-0.8	1
0.8-0.85	3
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC605784
0.9286	High Similarity	NPC136042
0.8919	High Similarity	NPC116458
0.8919	High Similarity	NPC246943
0.863	High Similarity	NPC84362
0.863	High Similarity	NPC271692
0.8333	Intermediate Similarity	NPC251417
0.8243	Intermediate Similarity	NPC297987
0.8108	Intermediate Similarity	NPC249281
0.7867	Intermediate Similarity	NPC289667
0.7816	Intermediate Similarity	NPC14187
0.7662	Intermediate Similarity	NPC46420
0.7561	Intermediate Similarity	NPC480466
0.7532	Intermediate Similarity	NPC158674
0.7473	Intermediate Similarity	NPC480441
0.7468	Intermediate Similarity	NPC611303
0.7442	Intermediate Similarity	NPC35119
0.7407	Intermediate Similarity	NPC276377
0.7308	Intermediate Similarity	NPC145038
0.7308	Intermediate Similarity	NPC56077
0.7308	Intermediate Similarity	NPC281131
0.7308	Intermediate Similarity	NPC253662
0.7308	Intermediate Similarity	NPC179950
0.7308	Intermediate Similarity	NPC277205
0.7308	Intermediate Similarity	NPC37919
0.7308	Intermediate Similarity	NPC88789
0.7308	Intermediate Similarity	NPC189142
0.7308	Intermediate Similarity	NPC77660
0.7308	Intermediate Similarity	NPC491374
0.725	Intermediate Similarity	NPC488071
0.7241	Intermediate Similarity	NPC32641
0.7241	Intermediate Similarity	NPC256188
0.7215	Intermediate Similarity	NPC27640
0.7179	Intermediate Similarity	NPC127546
0.7179	Intermediate Similarity	NPC57625
0.7179	Intermediate Similarity	NPC19709
0.7179	Intermediate Similarity	NPC173637
0.7179	Intermediate Similarity	NPC317489
0.7179	Intermediate Similarity	NPC238376
0.7179	Intermediate Similarity	NPC223424
0.7179	Intermediate Similarity	NPC600591
0.7176	Intermediate Similarity	NPC150164
0.7011	Intermediate Similarity	NPC64425
0.6914	Remote Similarity	NPC42773
0.6914	Remote Similarity	NPC59534
0.6914	Remote Similarity	NPC45522
0.6914	Remote Similarity	NPC599850
0.6897	Remote Similarity	NPC186816
0.679	Remote Similarity	NPC305811
0.6737	Remote Similarity	NPC25523
0.6667	Remote Similarity	NPC72016
0.6628	Remote Similarity	NPC480463
0.6543	Remote Similarity	NPC39360
0.6543	Remote Similarity	NPC77672
0.6543	Remote Similarity	NPC133671
0.6543	Remote Similarity	NPC135391
0.6543	Remote Similarity	NPC29763
0.6543	Remote Similarity	NPC78263
0.6543	Remote Similarity	NPC210003
0.6543	Remote Similarity	NPC250069
0.6512	Remote Similarity	NPC265115
0.65	Remote Similarity	NPC67037
0.65	Remote Similarity	NPC255615
0.6484	Remote Similarity	NPC606657
0.6463	Remote Similarity	NPC323593
0.6463	Remote Similarity	NPC203500
0.6444	Remote Similarity	NPC240306
0.642	Remote Similarity	NPC111929
0.642	Remote Similarity	NPC320283
0.642	Remote Similarity	NPC473043
0.642	Remote Similarity	NPC331652
0.642	Remote Similarity	NPC41121
0.6386	Remote Similarity	NPC24043
0.6341	Remote Similarity	NPC19388
0.6341	Remote Similarity	NPC240431
0.6341	Remote Similarity	NPC55786
0.6341	Remote Similarity	NPC108831
0.6341	Remote Similarity	NPC182634
0.6292	Remote Similarity	NPC471748
0.6265	Remote Similarity	NPC64305
0.6237	Remote Similarity	NPC486577
0.6222	Remote Similarity	NPC156869
0.6222	Remote Similarity	NPC605592
0.622	Remote Similarity	NPC135599
0.622	Remote Similarity	NPC73855
0.622	Remote Similarity	NPC113968
0.622	Remote Similarity	NPC328940
0.622	Remote Similarity	NPC277174
0.622	Remote Similarity	NPC606877
0.6196	Remote Similarity	NPC483414
0.6196	Remote Similarity	NPC483415
0.618	Remote Similarity	NPC29958
0.6163	Remote Similarity	NPC601144
0.6154	Remote Similarity	NPC115674
0.6145	Remote Similarity	NPC261866
0.6129	Remote Similarity	NPC483416
0.6118	Remote Similarity	NPC472459
0.6111	Remote Similarity	NPC67105
0.6092	Remote Similarity	NPC311830
0.6071	Remote Similarity	NPC95090
0.6071	Remote Similarity	NPC27408
0.6061	Remote Similarity	NPC164704
0.6047	Remote Similarity	NPC60735
0.6047	Remote Similarity	NPC26230
0.6047	Remote Similarity	NPC285197
0.6044	Remote Similarity	NPC203259
0.6044	Remote Similarity	NPC33054
0.6044	Remote Similarity	NPC210073
0.6044	Remote Similarity	NPC155877
0.6044	Remote Similarity	NPC176740
0.6044	Remote Similarity	NPC471725
0.6044	Remote Similarity	NPC134532
0.6044	Remote Similarity	NPC602582
0.6023	Remote Similarity	NPC203050
0.6023	Remote Similarity	NPC488072
0.6023	Remote Similarity	NPC225434
0.6022	Remote Similarity	NPC470443
0.6	Remote Similarity	NPC488080
0.6	Remote Similarity	NPC349108
0.6	Remote Similarity	NPC169977
0.5977	Remote Similarity	NPC22832
0.5977	Remote Similarity	NPC120099
0.5941	Remote Similarity	NPC470716
0.5914	Remote Similarity	NPC488073
0.5909	Remote Similarity	NPC223747
0.5909	Remote Similarity	NPC223860
0.59	Remote Similarity	NPC470715
0.5895	Remote Similarity	NPC5319
0.5889	Remote Similarity	NPC8856
0.5882	Remote Similarity	NPC8573
0.5882	Remote Similarity	NPC168822
0.5862	Remote Similarity	NPC307938
0.5862	Remote Similarity	NPC175107
0.5862	Remote Similarity	NPC219904
0.5843	Remote Similarity	NPC190003
0.5843	Remote Similarity	NPC601586
0.5842	Remote Similarity	NPC277532
0.5833	Remote Similarity	NPC473073
0.5833	Remote Similarity	NPC473071
0.5814	Remote Similarity	NPC245014
0.5814	Remote Similarity	NPC58716
0.5814	Remote Similarity	NPC45638
0.581	Remote Similarity	NPC470720
0.58	Remote Similarity	NPC292019
0.58	Remote Similarity	NPC202908
0.5795	Remote Similarity	NPC101026
0.5795	Remote Similarity	NPC243930
0.5795	Remote Similarity	NPC21666
0.5795	Remote Similarity	NPC488077
0.5795	Remote Similarity	NPC486578
0.5783	Remote Similarity	NPC288084
0.5778	Remote Similarity	NPC254855
0.5778	Remote Similarity	NPC116864
0.5778	Remote Similarity	NPC244776
0.5778	Remote Similarity	NPC94610
0.5747	Remote Similarity	NPC325555
0.5747	Remote Similarity	NPC226304
0.5747	Remote Similarity	NPC117260
0.5747	Remote Similarity	NPC201292
0.5745	Remote Similarity	NPC126784
0.5745	Remote Similarity	NPC241423
0.5729	Remote Similarity	NPC64755
0.5714	Remote Similarity	NPC470719
0.5714	Remote Similarity	NPC470717
0.5698	Remote Similarity	NPC265530
0.5698	Remote Similarity	NPC609879
0.5679	Remote Similarity	NPC191154
0.5676	Remote Similarity	NPC188871
0.5673	Remote Similarity	NPC295625
0.5667	Remote Similarity	NPC355481
0.5652	Remote Similarity	NPC139320
0.5618	Remote Similarity	NPC609478
0.561	Remote Similarity	NPC134819
0.5604	Remote Similarity	NPC95866
0.56	Remote Similarity	NPC121703
0.5595	Remote Similarity	NPC34531
0.5591	Remote Similarity	NPC275454
0.5567	Remote Similarity	NPC142142
0.5556	Remote Similarity	NPC607707
0.5532	Remote Similarity	NPC65003
0.5517	Remote Similarity	NPC282987
0.5517	Remote Similarity	NPC197896
0.5517	Remote Similarity	NPC313163
0.5484	Remote Similarity	NPC476773
0.5455	Remote Similarity	NPC52550
0.5455	Remote Similarity	NPC603655
0.5426	Remote Similarity	NPC173582
0.5426	Remote Similarity	NPC44931
0.5426	Remote Similarity	NPC265885
0.5426	Remote Similarity	NPC181465
0.5426	Remote Similarity	NPC67326
0.5426	Remote Similarity	NPC215710
0.5426	Remote Similarity	NPC163242
0.5426	Remote Similarity	NPC272068
0.5426	Remote Similarity	NPC473438
0.5426	Remote Similarity	NPC227508
0.5426	Remote Similarity	NPC253788
0.5412	Remote Similarity	NPC276222
0.5412	Remote Similarity	NPC274618
0.5412	Remote Similarity	NPC118284

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC527002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5647
0.1-0.2	3439
0.2-0.3	51
0.3-0.4	7
0.4-0.5	1
0.5-0.6	2
0.6-0.7	1
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
0.7079	Intermediate Similarity	NPD7251	Phase 2
0.6044	Remote Similarity	NPD6797	Phase 2
0.5895	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7808	Phase 3

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