NPASS Compound

Natural Product: NPC475660

Natural Product ID	NPC475660
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Euphotuckeyanol
IUPAC Name	[(1R,2R,3aR,5S,6E,9S,10S,11R,13R,13aS)-1,3a,9,10,13-pentaacetyloxy-2-benzoyloxy-2,5,8,8-tetramethyl-12-methylidene-4-oxo-1,3,5,9,10,11,13,13a-octahydrocyclopenta[12]annulen-11-yl] benzoate
Synonyms	Euphotuckeyanol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL510846
PubChem CID	44588923
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002877] Jatrophane and cyclojatrophane diterpenoids

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 109112 0 0 0 0 0 0 0 0999 V2000 -1.3707 0.5025 -3.6219 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6777 1.0113 -2.3916 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0909 2.1075 -2.4293 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6340 0.3437 -1.2238 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0695 0.7308 -0.0521 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7221 1.2747 1.0448 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2064 1.9313 2.0752 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2550 1.1726 1.0823 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7328 1.7757 -0.1315 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5966 2.8828 -0.0011 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8935 3.2724 1.1783 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1501 3.5837 -1.1308 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9923 4.6695 -0.8967 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5467 5.3704 -1.9433 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2789 5.0102 -3.2456 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4498 3.9409 -3.4801 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8775 3.2180 -2.4352 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6679 -0.2616 1.2496 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1148 -0.5394 2.5154 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6891 -1.1819 3.5920 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6037 -1.7698 3.6866 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5219 -1.2639 4.8747 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5155 -0.9145 0.2505 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4875 -0.5315 -1.0835 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7440 -0.3462 -1.6906 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7910 -0.5462 -0.9690 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0063 0.0539 -3.0665 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0662 -2.4284 0.1812 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7046 -3.0545 -1.0252 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7389 -3.1258 1.3828 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6407 -2.6176 0.3436 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6928 -3.0461 -0.4631 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7451 -3.1392 -0.0260 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9774 -2.4369 1.2196 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7852 -3.1276 2.2367 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4286 -0.9829 1.3723 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2283 -0.1674 0.1721 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5626 0.3825 -0.3122 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5419 1.6980 -0.7435 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9214 2.0501 -2.0596 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2788 1.1152 -2.8197 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9277 3.4096 -2.5927 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5549 0.0951 0.7653 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9752 -1.1575 1.3766 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5815 1.1931 1.8144 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8480 -0.2275 0.3556 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7820 0.5042 -0.2813 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5043 1.7058 -0.5576 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1043 -0.0432 -0.6650 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0541 0.6752 -1.3219 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2815 0.0975 -1.6623 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5275 -1.2172 -1.3257 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5707 -1.9554 -0.6591 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3516 -1.3502 -0.3315 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0159 -0.5085 2.5892 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3288 -0.9202 3.8296 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0973 -1.8873 4.0069 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7771 -0.2408 5.0718 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0948 -4.6124 0.0076 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5554 0.1091 -4.3004 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9022 1.2609 -4.1856 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9702 -0.3657 -3.3681 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5846 1.6920 -0.4686 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8452 2.3116 2.8616 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8553 2.1422 2.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6855 1.7379 1.9057 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2082 4.9580 0.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2108 6.2260 -1.7560 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6928 5.5305 -4.0948 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1861 3.5868 -4.4824 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2314 2.3889 -2.6377 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6288 -0.7971 1.2145 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3428 -2.1989 5.4035 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3808 -0.3389 5.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5782 -1.2651 4.5382 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5801 -1.0255 0.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4630 -0.8504 -3.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1592 0.4314 -3.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8524 0.7947 -3.0552 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3459 -4.0977 -1.1372 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4756 -2.4880 -1.9517 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7985 -3.1075 -0.8520 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2781 -4.0320 0.9675 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9752 -3.5399 2.0373 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4710 -2.4432 1.8316 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2453 -2.4359 1.3688 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8690 -3.3653 -1.4988 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3948 -2.7321 -0.8775 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0718 -1.0070 -0.6504 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9379 -0.2193 -1.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2763 4.0816 -2.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9690 3.8391 -2.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5922 3.4066 -3.6670 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4019 -1.2432 2.3597 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2244 -2.0035 0.6932 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1041 2.1198 1.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6653 1.4480 1.9894 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1322 0.8719 2.7300 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8633 1.6904 -1.5810 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0421 0.6402 -2.1787 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4885 -1.6421 -1.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7827 -2.9861 -0.4046 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6361 -1.9619 0.1870 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5746 -1.0660 5.7845 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5870 0.3758 5.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1326 0.3405 4.8215 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5434 -5.0595 0.8709 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1923 -4.7826 0.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6887 -5.1058 -0.9027 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 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 8 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 18 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 23 28 1 0 28 29 1 0 28 30 1 0 28 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 38 43 1 0 43 44 1 0 43 45 1 0 43 46 1 6 46 47 1 0 47 48 2 0 47 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 36 55 1 1 55 56 1 0 56 57 2 0 56 58 1 0 33 59 1 0 37 5 1 0 54 49 1 0 17 12 1 0 44 36 1 0 1 60 1 0 1 61 1 0 1 62 1 0 5 63 1 6 7 64 1 0 7 65 1 0 8 66 1 1 13 67 1 0 14 68 1 0 15 69 1 0 16 70 1 0 17 71 1 0 18 72 1 1 22 73 1 0 22 74 1 0 22 75 1 0 23 76 1 1 27 77 1 0 27 78 1 0 27 79 1 0 29 80 1 0 29 81 1 0 29 82 1 0 30 83 1 0 30 84 1 0 30 85 1 0 31 86 1 0 32 87 1 0 33 88 1 6 37 89 1 6 38 90 1 6 42 91 1 0 42 92 1 0 42 93 1 0 44 94 1 0 44 95 1 0 45 96 1 0 45 97 1 0 45 98 1 0 50 99 1 0 51100 1 0 52101 1 0 53102 1 0 54103 1 0 58104 1 0 58105 1 0 58106 1 0 59107 1 0 59108 1 0 59109 1 0 M END

Standard InCHIKey	FFSRBMPSPCZRMK-GWPHZUIASA-N
Standard InCHI	InChI=1S/C44H50O15/c1-24-21-22-42(8,9)39(56-29(6)48)36(54-27(4)46)35(57-40(51)31-17-13-11-14-18-31)25(2)34(53-26(3)45)33-38(55-28(5)47)43(10,23-44(33,37(24)50)58-30(7)49)59-41(52)32-19-15-12-16-20-32/h11-22,24,33-36,38-39H,2,23H2,1,3-10H3/b22-21+/t24-,33-,34-,35+,36+,38+,39+,43+,44+/m0/s1
SMILES	CC(=O)O[C@H]1C(=C)[C@@H](OC(=O)c2ccccc2)[C@@H](OC(=O)C)[C@@H](OC(=O)C)C(C)(C)/C=C/[C@@H](C(=O)[C@@]2([C@@H]1[C@@H](OC(=O)C)[C@](C2)(C)OC(=O)c1ccccc1)OC(=O)C)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
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18824363]
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[6736971]
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	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

Activity Type	# Activity
Ratio	2
Flu intensity	2
FICI	1
ID50	2

Activity Type	# Activity
Individual protein	4
Non-molecular	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	81.0	n.a.	PMID[23398362]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	1127.4	n.a.	PMID[18824363]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	106.2	n.a.	PMID[18694945]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	1476.7	n.a.	PMID[18824363]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	FICI	=	0.08	n.a.	PMID[18824363]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ID50	=	45.0	ug ml-1	PMID[18824363]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ID50	=	22.8	ug ml-1	PMID[18824363]

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 NPC475660 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	13255
0.1-0.2	34524
0.2-0.3	1627
0.3-0.4	368
0.4-0.5	38
0.5-0.6	25
0.6-0.7	14
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC285221
0.9143	High Similarity	NPC194769
0.8243	Intermediate Similarity	NPC482254
0.7403	Intermediate Similarity	NPC265459
0.7403	Intermediate Similarity	NPC482304
0.7403	Intermediate Similarity	NPC482265
0.7179	Intermediate Similarity	NPC272523
0.6962	Remote Similarity	NPC475262
0.6962	Remote Similarity	NPC482249
0.6923	Remote Similarity	NPC325805
0.6829	Remote Similarity	NPC482253
0.6806	Remote Similarity	NPC482404
0.679	Remote Similarity	NPC482267
0.6543	Remote Similarity	NPC290833
0.6463	Remote Similarity	NPC482248
0.6395	Remote Similarity	NPC482250
0.6364	Remote Similarity	NPC471757
0.618	Remote Similarity	NPC482258
0.6118	Remote Similarity	NPC482255
0.6071	Remote Similarity	NPC482251
0.6024	Remote Similarity	NPC482266
0.5814	Remote Similarity	NPC482268
0.573	Remote Similarity	NPC319556
0.5647	Remote Similarity	NPC86772
0.5647	Remote Similarity	NPC482315
0.5638	Remote Similarity	NPC482260
0.5581	Remote Similarity	NPC482270
0.5543	Remote Similarity	NPC482154
0.5506	Remote Similarity	NPC482201
0.5495	Remote Similarity	NPC482155
0.5465	Remote Similarity	NPC482300
0.5444	Remote Similarity	NPC40919
0.5435	Remote Similarity	NPC482204
0.5393	Remote Similarity	NPC482252
0.5385	Remote Similarity	NPC482202
0.5281	Remote Similarity	NPC482269
0.5227	Remote Similarity	NPC482247
0.519	Remote Similarity	NPC78127
0.5172	Remote Similarity	NPC482308
0.5158	Remote Similarity	NPC470189
0.5122	Remote Similarity	NPC482403
0.5114	Remote Similarity	NPC482314
0.5111	Remote Similarity	NPC472247
0.5111	Remote Similarity	NPC482359
0.5104	Remote Similarity	NPC482259
0.5055	Remote Similarity	NPC482263

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475660 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4049
0.1-0.2	5033
0.2-0.3	68
0.3-0.4	0
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