NPASS Compound

Natural Product: NPC145957

Natural Product ID	NPC145957
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ABEPLDYBWOKMCT-PUWSOPCHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44258792
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 105110 0 0 0 0 0 0 0 0999 V2000 -3.8074 1.0147 -2.6576 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5471 2.0963 -1.9658 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4975 2.4090 -0.7123 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7538 1.8540 0.3939 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8797 0.7005 0.1660 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4146 -0.5819 0.0220 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5786 -1.6439 -0.1619 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2155 -1.4672 -0.2073 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6842 -0.2158 -0.0670 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6675 0.0062 -0.1011 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4077 -0.9858 -0.2695 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1443 1.2895 0.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2777 2.3208 0.2245 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6519 3.7108 0.3819 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8806 4.2544 0.1002 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1761 5.6012 0.3169 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2131 6.4378 0.8321 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0202 5.9242 1.1213 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2811 4.6035 0.8996 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4562 7.7962 1.0690 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0349 2.0709 0.2560 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4954 0.8776 0.1199 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5288 1.4220 0.0094 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3238 1.1276 1.1609 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6097 0.5179 0.7079 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5408 1.7144 0.4302 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9534 2.2383 1.7881 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6946 2.2800 2.6293 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7376 3.5564 3.4421 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5500 2.3303 1.8384 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5896 3.4639 1.7120 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5940 1.3624 -0.3731 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5578 -0.3189 -0.3762 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1723 -1.5394 -0.1177 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2586 -2.6491 -0.4502 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9450 -3.9968 -0.4806 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3935 -3.8866 -0.1532 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0681 -2.7133 -0.7445 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7199 -3.0035 -2.0796 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3519 -1.5507 -0.8584 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0208 -5.0404 -0.6849 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7297 -4.6058 -1.6996 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6702 -2.4394 -1.7037 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3748 -2.5416 -0.3934 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7767 -0.6763 0.0786 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5705 -1.8126 -0.0318 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3162 -1.9486 1.3035 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2193 -3.1482 1.1841 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1574 -2.8822 0.0252 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3995 -2.5903 -1.2367 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8438 -3.8517 -1.8693 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8472 -4.8160 -1.9979 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4518 -1.6112 -1.0872 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0598 -3.9013 -0.1693 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9757 -3.3658 2.3111 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0704 -0.7765 1.4418 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4769 2.9219 -2.8705 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7819 0.8700 -2.3477 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3669 0.0455 -2.5533 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8316 1.2164 -3.7709 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1599 3.2804 -0.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1207 2.6843 0.8322 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4361 1.6076 1.2822 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0355 -2.6248 -0.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6460 3.6439 -0.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1384 6.0145 0.0940 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7652 6.5925 1.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2742 4.2504 1.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2784 8.2128 0.6373 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6853 0.4597 1.7863 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1191 0.0014 1.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9072 2.5059 -0.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6259 1.5078 2.2549 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6163 1.4476 3.3368 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6626 3.6251 4.0503 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8239 3.5845 4.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6446 4.4083 2.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2912 4.0099 0.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3168 1.4759 -1.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4854 -1.5260 0.9524 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4437 -2.7058 0.2883 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4955 -4.6884 0.2908 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 -3.9771 0.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9371 -2.4635 -0.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5413 -2.2626 -2.2397 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9869 -2.8273 -2.8929 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0899 -4.0463 -2.1573 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8754 -5.2182 -0.2191 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5339 -4.6347 -2.2727 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3414 -2.3391 -2.3998 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6479 -3.4285 -0.7998 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0603 -2.7612 -0.1834 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5498 -2.0464 2.0803 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5704 -4.0297 1.0138 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6988 -1.9293 0.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1522 -2.1930 -1.9728 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4731 -3.6625 -2.8963 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9993 -4.2367 -1.2740 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6481 -4.4184 -2.4155 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9867 -3.5481 -0.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8917 -3.6827 2.0902 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6671 -0.8143 2.2208 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9736 2.1903 -3.5126 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8879 3.6917 -3.3906 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2287 3.3963 -2.2305 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 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 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 17 20 1 0 13 21 1 0 21 22 1 0 12 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 27 31 1 0 26 32 1 0 25 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 38 40 1 0 37 41 1 0 36 42 1 0 35 43 1 0 8 44 1 0 6 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 48 55 1 0 47 56 1 0 2 57 1 0 22 5 1 0 30 24 1 0 40 34 1 0 53 46 1 0 22 9 2 0 19 14 1 0 1 58 1 0 1 59 1 0 1 60 1 0 3 61 1 0 4 62 1 0 4 63 1 0 7 64 1 0 15 65 1 0 16 66 1 0 18 67 1 0 19 68 1 0 20 69 1 0 24 70 1 1 25 71 1 1 26 72 1 0 27 73 1 1 28 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 31 78 1 0 32 79 1 0 34 80 1 1 35 81 1 1 36 82 1 0 37 83 1 1 38 84 1 0 39 85 1 0 39 86 1 0 39 87 1 0 41 88 1 0 42 89 1 0 43 90 1 0 44 91 1 0 46 92 1 6 47 93 1 0 48 94 1 6 49 95 1 1 50 96 1 0 51 97 1 0 51 98 1 0 52 99 1 0 54100 1 0 55101 1 0 56102 1 0 57103 1 0 57104 1 0 57105 1 0 M END

Standard InCHIKey	ABEPLDYBWOKMCT-PUWSOPCHSA-N
Standard InCHI	InChI=1S/C38H48O19/c1-13(2)5-10-18-20(53-37-31(50)28(47)25(44)21(12-39)54-37)11-19(41)22-26(45)34(32(55-33(18)22)16-6-8-17(40)9-7-16)56-38-35(29(48)24(43)15(4)52-38)57-36-30(49)27(46)23(42)14(3)51-36/h5-9,11,14-15,21,23-25,27-31,35-44,46-50H,10,12H2,1-4H3/t14?,15?,21?,23-,24-,25+,27?,28-,29?,30-,31?,35-,36-,37+,38-/m0/s1
SMILES	CC(=CCc1c(cc(c2c(=O)c(c(c3ccc(cc3)O)oc12)O[C@H]1[C@H](C([C@H](C(C)O1)O)O)O[C@H]1[C@H](C([C@H](C(C)O1)O)O)O)O)O[C@H]1C([C@H]([C@@H](C(CO)O1)O)O)O)C

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
NPO28569	Epimedium acuminatum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[1442064]
NPO28569	Epimedium acuminatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36300020]
NPO28569	Epimedium acuminatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10214	Epimedium wanshanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28569	Epimedium acuminatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10214	Epimedium wanshanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10214	Epimedium wanshanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28569	Epimedium acuminatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28569	Epimedium acuminatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10214	Epimedium wanshanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28569	Epimedium acuminatum	Species	Berberidaceae	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
NPO28569	Epimedium acuminatum	n.a.	n.a.	205.579	n.a.	n.a.	Î¼g/g	PMID[36300020]
NPO28569	Epimedium acuminatum	n.a.	n.a.	354.095	n.a.	n.a.	Î¼g/g	PMID[36300020]
NPO28569	Epimedium acuminatum	n.a.	n.a.	1,461.200	n.a.	n.a.	Î¼g/g	PMID[36300020]
NPO28569	Epimedium acuminatum	n.a.	n.a.	65.928	n.a.	n.a.	Î¼g/g	PMID[36300020]

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 NPC145957 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	18227
0.1-0.2	26932
0.2-0.3	3827
0.3-0.4	577
0.4-0.5	228
0.5-0.6	52
0.6-0.7	9
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
0.7449	Intermediate Similarity	NPC5319
0.6667	Remote Similarity	NPC32641
0.6667	Remote Similarity	NPC256188
0.6667	Remote Similarity	NPC35119
0.6422	Remote Similarity	NPC25523
0.6311	Remote Similarity	NPC240306
0.6176	Remote Similarity	NPC163242
0.6176	Remote Similarity	NPC272068
0.61	Remote Similarity	NPC476215
0.61	Remote Similarity	NPC66087
0.5905	Remote Similarity	NPC470444
0.5905	Remote Similarity	NPC131745
0.5842	Remote Similarity	NPC116458
0.5842	Remote Similarity	NPC246943
0.5841	Remote Similarity	NPC480441
0.5818	Remote Similarity	NPC602448
0.5784	Remote Similarity	NPC170052
0.5784	Remote Similarity	NPC135846
0.5766	Remote Similarity	NPC14187
0.5701	Remote Similarity	NPC64425
0.566	Remote Similarity	NPC155877
0.5577	Remote Similarity	NPC95866
0.5545	Remote Similarity	NPC142142
0.5524	Remote Similarity	NPC473682
0.5514	Remote Similarity	NPC183672
0.55	Remote Similarity	NPC297987
0.5431	Remote Similarity	NPC164704
0.5377	Remote Similarity	NPC278419
0.5377	Remote Similarity	NPC179198
0.537	Remote Similarity	NPC65003
0.5364	Remote Similarity	NPC12013
0.5364	Remote Similarity	NPC11432
0.5364	Remote Similarity	NPC477613
0.5357	Remote Similarity	NPC220173
0.5285	Remote Similarity	NPC480443
0.5283	Remote Similarity	NPC254855
0.5283	Remote Similarity	NPC94610
0.5278	Remote Similarity	NPC470405
0.5248	Remote Similarity	NPC249281
0.5248	Remote Similarity	NPC77672
0.5248	Remote Similarity	NPC133671
0.5248	Remote Similarity	NPC135391
0.5248	Remote Similarity	NPC78263
0.5248	Remote Similarity	NPC250069
0.5238	Remote Similarity	NPC605784
0.5196	Remote Similarity	NPC8573
0.5169	Remote Similarity	NPC470715
0.5161	Remote Similarity	NPC192539
0.5146	Remote Similarity	NPC46420
0.5091	Remote Similarity	NPC304741
0.5088	Remote Similarity	NPC76831
0.5088	Remote Similarity	NPC473071
0.5083	Remote Similarity	NPC255799
0.5081	Remote Similarity	NPC209550
0.5048	Remote Similarity	NPC168584
0.5046	Remote Similarity	NPC480466
0.5046	Remote Similarity	NPC139320
0.5045	Remote Similarity	NPC186816
0.5043	Remote Similarity	NPC292929
0.5043	Remote Similarity	NPC221342
0.5043	Remote Similarity	NPC476470
0.5041	Remote Similarity	NPC470717

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC145957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5013
0.1-0.2	4073
0.2-0.3	55
0.3-0.4	5
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
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
0.7449	Intermediate Similarity	NPD7804	Clinical (unspecified phase)

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