NPASS Compound

Natural Product: NPC167289

Natural Product ID	NPC167289
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DEJZBLSEQHTJRX-IWVOJEJNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5315276
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 115120 0 0 0 0 0 0 0 0999 V2000 7.6498 -0.5492 -3.0674 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6342 -1.4404 -3.7311 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1132 -2.8697 -3.6389 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2496 -3.2244 -2.1914 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6322 -4.3585 -1.8760 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9497 -2.2960 -1.2286 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0552 -2.5868 0.1479 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6459 -1.3293 0.9233 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6884 -1.6924 2.3989 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9392 -0.6510 3.1534 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6420 0.5218 2.2894 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8862 0.1814 1.0213 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3479 -1.0109 0.5300 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5426 0.2200 1.3105 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8130 1.1932 0.7221 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1976 2.2729 1.5226 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6924 2.3874 1.4213 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0534 1.0290 1.4597 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4194 0.5445 2.8127 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5314 0.2459 0.2793 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1454 -1.1509 0.5843 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3765 -1.2797 0.5350 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1547 -0.2233 1.2861 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2480 -0.8149 2.7255 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4483 1.0956 1.3355 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7732 2.0175 0.2394 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1197 1.8264 -0.3549 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9580 0.8528 -0.1488 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2973 0.7740 -0.8033 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4581 0.3682 -2.1876 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7680 1.0401 -2.6722 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6458 0.0682 -3.4220 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3194 2.0468 -3.7521 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4663 1.8371 -1.6423 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5640 1.3250 -0.2443 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3895 0.4235 0.1488 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8142 0.8238 1.5150 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6144 0.0306 1.9323 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5808 -0.2004 0.8252 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9221 -1.5947 0.3074 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6427 2.1885 1.4890 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9704 -0.8712 0.2438 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0628 -1.4136 1.4002 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4799 -1.6906 -0.7436 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8594 0.5606 -0.2752 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7711 1.5458 -1.4650 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5170 -0.6573 -0.8853 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7363 -1.2701 -1.8680 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7643 1.3176 2.0452 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7840 -1.1562 3.7496 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0120 -1.6844 2.7907 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1873 -0.0514 -2.1677 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4993 -1.1507 -2.6603 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9934 0.2202 -3.7694 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6473 -1.4156 -3.2128 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5018 -1.1679 -4.7820 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0835 -2.9430 -4.1601 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3645 -3.5376 -4.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4080 -3.4309 0.4699 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1022 -2.8697 0.3752 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3668 -0.5190 0.7610 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2920 -2.7149 2.5740 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5718 -0.2690 4.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9558 1.1951 2.8851 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1757 1.0226 0.3128 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5982 1.7112 0.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5556 2.3432 2.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5587 3.2889 1.1522 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3956 3.0512 0.6335 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3808 2.9084 2.3802 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2629 -0.4747 3.0848 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5122 0.7228 3.0679 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0659 1.2864 3.5267 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1698 0.4645 -0.5934 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4878 -1.8226 -0.2199 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5889 -1.5933 1.4985 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4647 -2.3012 0.9875 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6649 -1.2364 -0.5217 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0403 -0.0666 3.4827 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2494 -1.2075 2.9693 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6237 -1.7568 2.8008 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7739 1.5446 2.3349 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7124 3.0781 0.6982 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0810 2.1384 -0.6003 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4991 2.5923 -1.0773 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5070 1.9320 -0.9450 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4901 -0.6782 -2.4750 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5727 0.7842 -2.7616 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5456 -0.1436 -2.7808 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9221 0.3732 -4.4283 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0895 -0.9083 -3.4290 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6781 2.8370 -3.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2442 2.4420 -4.2197 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8148 1.4485 -4.5423 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1359 2.9197 -1.6553 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5342 1.9315 -2.0139 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5469 0.8813 -0.0279 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4820 2.2071 0.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6377 0.6002 2.2238 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1578 0.5556 2.7826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9913 -0.9367 2.2924 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5378 -2.1751 1.0722 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3877 -1.5680 -0.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0830 -2.2909 0.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8514 2.6622 2.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1576 -2.4260 -0.5834 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7805 1.4979 -1.9505 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6007 1.3563 -2.1829 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9432 2.5522 -1.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4535 -0.3317 -1.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7952 -1.3970 -0.0933 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0628 -0.6637 -2.2407 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5284 1.0047 2.6055 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3827 -1.7899 3.1251 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4765 -2.4382 2.3516 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 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 26 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 31 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 37 41 1 0 36 42 1 0 42 43 2 0 42 44 1 0 20 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 11 49 1 0 10 50 1 0 9 51 1 0 13 8 1 0 45 15 1 0 25 18 1 0 39 28 1 0 39 23 1 0 36 29 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 0 2 56 1 0 3 57 1 0 3 58 1 0 7 59 1 0 7 60 1 0 8 61 1 1 9 62 1 6 10 63 1 1 11 64 1 1 12 65 1 6 15 66 1 0 16 67 1 0 16 68 1 0 17 69 1 0 17 70 1 0 19 71 1 0 19 72 1 0 19 73 1 0 20 74 1 0 21 75 1 0 21 76 1 0 22 77 1 0 22 78 1 0 24 79 1 0 24 80 1 0 24 81 1 0 25 82 1 0 26 83 1 0 26 84 1 0 27 85 1 0 29 86 1 0 30 87 1 0 30 88 1 0 32 89 1 0 32 90 1 0 32 91 1 0 33 92 1 0 33 93 1 0 33 94 1 0 34 95 1 0 34 96 1 0 35 97 1 0 35 98 1 0 37 99 1 0 38100 1 0 38101 1 0 40102 1 0 40103 1 0 40104 1 0 41105 1 0 44106 1 0 46107 1 0 46108 1 0 46109 1 0 47110 1 0 47111 1 0 48112 1 0 49113 1 0 50114 1 0 51115 1 0 M END

Standard InCHIKey	DEJZBLSEQHTJRX-IWVOJEJNSA-N
Standard InCHI	InChI=1S/C40H64O11/c1-8-9-29(43)49-20-24-30(44)31(45)32(46)33(50-24)51-28-13-14-36(4)25(37(28,5)21-41)12-15-38(6)26(36)11-10-22-23-18-35(2,3)16-17-40(23,34(47)48)27(42)19-39(22,38)7/h10,23-28,30-33,41-42,44-46H,8-9,11-21H2,1-7H3,(H,47,48)/t23?,24-,25?,26?,27?,28?,30-,31+,32-,33+,36?,37?,38?,39?,40?/m1/s1
SMILES	CCCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC1CCC2(C)C(CCC3(C)C2CC=C2C4CC(C)(C)CCC4(C(CC32C)O)C(=O)O)C1(C)CO)O)O)O

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
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	whole plant	n.a.	n.a.	DOI[10.1016/j.tetlet.2016.12.029]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38732062]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17494	Prunella vulgaris	Species	Lamiaceae	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 NPC167289 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	18257
0.1-0.2	25911
0.2-0.3	4307
0.3-0.4	981
0.4-0.5	313
0.5-0.6	69
0.6-0.7	15
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
0.75	Intermediate Similarity	NPC488516
0.7253	Intermediate Similarity	NPC31839
0.7041	Intermediate Similarity	NPC480424
0.701	Intermediate Similarity	NPC136877
0.699	Remote Similarity	NPC488515
0.6809	Remote Similarity	NPC242611
0.6739	Remote Similarity	NPC204407
0.6569	Remote Similarity	NPC80843
0.6327	Remote Similarity	NPC284807
0.6316	Remote Similarity	NPC28198
0.6316	Remote Similarity	NPC476123
0.6306	Remote Similarity	NPC288205
0.6306	Remote Similarity	NPC51465
0.6168	Remote Similarity	NPC139044
0.6146	Remote Similarity	NPC606107
0.6139	Remote Similarity	NPC270667
0.6117	Remote Similarity	NPC59804
0.6091	Remote Similarity	NPC75318
0.6019	Remote Similarity	NPC471383
0.5982	Remote Similarity	NPC475486
0.5962	Remote Similarity	NPC174679
0.5962	Remote Similarity	NPC279554
0.5926	Remote Similarity	NPC104400
0.5926	Remote Similarity	NPC10320
0.5914	Remote Similarity	NPC601365
0.5865	Remote Similarity	NPC12288
0.5856	Remote Similarity	NPC37134
0.578	Remote Similarity	NPC473383
0.5778	Remote Similarity	NPC228784
0.5778	Remote Similarity	NPC324341
0.5778	Remote Similarity	NPC601810
0.5676	Remote Similarity	NPC257468
0.5673	Remote Similarity	NPC76999
0.5664	Remote Similarity	NPC323359
0.5664	Remote Similarity	NPC291903
0.5657	Remote Similarity	NPC283849
0.5657	Remote Similarity	NPC57362
0.5644	Remote Similarity	NPC100383
0.5607	Remote Similarity	NPC127056
0.5593	Remote Similarity	NPC323341
0.5591	Remote Similarity	NPC222047
0.5575	Remote Similarity	NPC276093
0.5543	Remote Similarity	NPC201657
0.5534	Remote Similarity	NPC473538
0.5524	Remote Similarity	NPC164194
0.5495	Remote Similarity	NPC180550
0.5495	Remote Similarity	NPC35405
0.5487	Remote Similarity	NPC119794
0.5478	Remote Similarity	NPC488564
0.547	Remote Similarity	NPC475119
0.5424	Remote Similarity	NPC473824
0.5413	Remote Similarity	NPC472949
0.5392	Remote Similarity	NPC286347
0.5385	Remote Similarity	NPC294112
0.5385	Remote Similarity	NPC62725
0.537	Remote Similarity	NPC25605
0.537	Remote Similarity	NPC56713
0.5364	Remote Similarity	NPC22956
0.5321	Remote Similarity	NPC114441
0.5321	Remote Similarity	NPC109079
0.5319	Remote Similarity	NPC471588
0.5294	Remote Similarity	NPC177246
0.5289	Remote Similarity	NPC219180
0.5273	Remote Similarity	NPC295371
0.5273	Remote Similarity	NPC488561
0.5238	Remote Similarity	NPC471385
0.5238	Remote Similarity	NPC475633
0.5234	Remote Similarity	NPC127853
0.5217	Remote Similarity	NPC79718
0.5208	Remote Similarity	NPC6255
0.5207	Remote Similarity	NPC133818
0.5182	Remote Similarity	NPC173583
0.5172	Remote Similarity	NPC145899
0.5164	Remote Similarity	NPC166422
0.514	Remote Similarity	NPC480938
0.5135	Remote Similarity	NPC473884
0.5135	Remote Similarity	NPC6377
0.5135	Remote Similarity	NPC208381
0.5133	Remote Similarity	NPC114304
0.513	Remote Similarity	NPC73829
0.5128	Remote Similarity	NPC324875
0.5128	Remote Similarity	NPC292677
0.5085	Remote Similarity	NPC488209
0.5083	Remote Similarity	NPC476992
0.5081	Remote Similarity	NPC54636
0.5046	Remote Similarity	NPC48499
0.5045	Remote Similarity	NPC473373
0.5044	Remote Similarity	NPC469945

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC167289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5919
0.1-0.2	3152
0.2-0.3	72
0.3-0.4	7
0.4-0.5	0
0.5-0.6	0
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
		NPD

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