NPASS Compound

Natural Product: NPC294050

Natural Product ID	NPC294050
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hyperibone A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL593291
PubChem CID	45484342
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

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 80 83 0 0 0 0 0 0 0 0999 V2000 3.2431 0.0624 5.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3385 0.1329 3.6240 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2921 0.4483 2.8897 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4080 0.5119 1.4062 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4752 -0.4593 0.8058 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0511 -0.1867 1.1434 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5961 0.8585 0.3059 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0693 2.0523 1.1109 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0392 1.5964 2.1180 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8947 1.7889 3.4113 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7810 2.4718 4.0895 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9702 1.2673 4.3629 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7597 0.3418 -0.4549 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4869 -0.4858 -1.4584 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2239 -0.4229 -2.1889 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1955 -0.8736 -3.3389 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0075 0.1799 -1.5540 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6904 -0.7669 -0.6788 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1884 -0.9113 -0.8362 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1409 -2.1975 -0.8405 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4193 1.2942 -0.7152 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6977 2.4524 -0.8105 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7670 0.8166 -2.6318 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8470 2.1107 -2.4945 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4227 0.3202 -3.7790 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0007 1.2177 -4.6940 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6653 0.7882 -5.8256 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7851 -0.5558 -6.0982 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2295 -1.4689 -5.2205 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5652 -0.9918 -4.0861 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7175 -1.3538 -1.5723 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7801 -0.3036 -1.3282 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1521 0.5167 -0.3774 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0583 -0.9276 -0.8264 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7916 -1.7031 0.2744 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5426 -1.8627 -1.9412 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1263 0.0794 -0.5796 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6296 -0.1513 2.9414 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2474 0.3582 5.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9276 -0.9394 5.4675 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5379 0.8396 5.4664 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3741 0.6568 3.4273 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2342 1.5847 1.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4773 0.3567 1.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6983 -1.4421 1.3721 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5688 -1.1353 1.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0374 0.0726 2.1958 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5508 2.7424 0.3590 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2663 2.6009 1.5808 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9590 1.0575 1.8203 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2675 3.1937 4.8202 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2353 1.7672 4.7825 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1094 3.0579 3.4738 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5110 0.4464 4.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2780 2.0965 5.0277 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8417 0.9138 3.7880 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4745 -1.7688 -1.5160 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7244 0.0113 -1.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5593 -1.3313 0.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9202 -2.8442 -1.3321 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1869 -2.2333 -1.3604 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9880 -2.6682 0.1499 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9383 2.2856 -4.5335 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1017 1.4854 -6.5154 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3096 -0.8643 -6.9899 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3081 -2.5191 -5.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1815 -1.7575 -3.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7884 -1.8212 -2.5599 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6689 -2.0919 -0.7369 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9286 0.2300 -2.2961 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6562 -2.1340 0.5617 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9067 -2.7710 -1.9848 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3354 -1.3068 -2.8962 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6188 -2.1016 -1.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2005 0.2896 0.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9792 0.9901 -1.1834 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1116 -0.3635 -0.8704 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5930 -1.0162 2.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3848 -0.4050 3.7308 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9735 0.7924 2.4559 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 1 0 6 7 1 0 7 8 1 1 8 9 1 0 9 10 2 3 10 11 1 0 10 12 1 0 7 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 17 21 1 0 21 22 2 0 17 23 1 6 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 14 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 34 37 1 0 2 38 1 0 18 5 1 0 30 25 1 0 21 7 1 0 33 13 1 0 1 39 1 0 1 40 1 0 1 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 1 6 46 1 0 6 47 1 0 8 48 1 0 8 49 1 0 9 50 1 0 11 51 1 0 11 52 1 0 11 53 1 0 12 54 1 0 12 55 1 0 12 56 1 0 19 57 1 0 19 58 1 0 19 59 1 0 20 60 1 0 20 61 1 0 20 62 1 0 26 63 1 0 27 64 1 0 28 65 1 0 29 66 1 0 30 67 1 0 31 68 1 0 31 69 1 0 32 70 1 6 35 71 1 0 36 72 1 0 36 73 1 0 36 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 38 78 1 0 38 79 1 0 38 80 1 0 M END

Standard InCHIKey	PHBDYBJOGVFIQU-JVDFBSCCSA-N
Standard InCHI	InChI=1S/C33H42O5/c1-20(2)14-15-23-19-32(17-16-21(3)4)28-24(18-25(38-28)31(7,8)37)27(35)33(29(32)36,30(23,5)6)26(34)22-12-10-9-11-13-22/h9-14,16,23,25,37H,15,17-19H2,1-8H3/t23-,25-,32+,33-/m0/s1
SMILES	CC(=CC[C@H]1C[C@]2(CC=C(C)C)C3=C(C(=O)[C@](C1(C)C)(C2=O)C(=O)c1ccccc1)C[C@H](O3)C(O)(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.3	Volume:	565.321 ? Van der Waals volume.
Dense:	0.917	LogP:	5.82 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.479 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.75 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	25.0
TPSA:	80.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.251	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.509	Fsp³:	0.545
MCE-18:	111.333 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.85	Fluc inhibitor:	0.094 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.096 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.607 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.295	Promiscuous compounds:	0.018

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.612	MDCK Permeability:	-4.703
Pgp-inhibitor:	0.006	Pgp-substrate:	0.82
PAMPA:	0.519 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999	MRP1:	0.897
Plasma Protein Binding (PPB):	70.138%	Volume Distribution (VD):	0.063
Fu:	27.136% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.314
OATP1B3 inhibitor:	0.006	BCRP inhibitor:	0.004
BSEP inhibitor:	0.592

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.999
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.956 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.995

Half-life (T1/2):

0.657

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.17
Human Hepatotoxicity (H-HT):	0.726	Drug-induced Liver Injury (DILI):	0.51
AMES Toxicity:	0.463	Rat Oral Acute Toxicity:	0.595
Maximum Recommended Daily Dose:	0.382	Skin Sensitization:	1.0
Carcinogencity:	0.962	Eye Corrosion:	0.001
Eye Irritation:	0.551	Respiratory Toxicity:	0.967
Drug-induced Neurotoxicity:	0.233	Ototoxicity:	0.307
Hematotoxicity:	0.39	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.016
A549 Cytotoxicity:	0.007	Hek293 Cytotoxicity:	0.136
BCF:	1.944 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.984 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.844 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.478 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

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
MBC	4
MIC	4
IC50	1

Activity Type	# Activity
Cell line	1
Organism	8

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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	175.6	nM	PMID[19497755]
NPT4401	Organism	Streptococcus oralis	Streptococcus oralis	MBC	=	26.0	ug ml-1	PMID[19497755]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.73	ug.mL-1	PMID[19497755]
NPT4401	Organism	Streptococcus oralis	Streptococcus oralis	MIC	=	1.65	ug.mL-1	PMID[19497755]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	5.85	ug ml-1	PMID[19497755]
NPT4399	Organism	Actinomyces naeslundii	Actinomyces naeslundii	MIC	=	1.65	ug.mL-1	PMID[19497755]
NPT4402	Organism	Streptococcus gordonii	Streptococcus gordonii	MIC	=	1.65	ug.mL-1	PMID[19497755]
NPT4402	Organism	Streptococcus gordonii	Streptococcus gordonii	MBC	=	26.0	ug ml-1	PMID[19497755]
NPT4399	Organism	Actinomyces naeslundii	Actinomyces naeslundii	MBC	=	6.6	ug ml-1	PMID[19497755]

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 NPC294050 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	8651
0.1-0.2	39362
0.2-0.3	1648
0.3-0.4	90
0.4-0.5	74
0.5-0.6	16
0.6-0.7	10
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC328997
1.0	High Similarity	NPC610705
0.8382	Intermediate Similarity	NPC47466
0.8382	Intermediate Similarity	NPC116274
0.8143	Intermediate Similarity	NPC483077
0.7183	Intermediate Similarity	NPC316553
0.7083	Intermediate Similarity	NPC325740
0.6849	Remote Similarity	NPC482993
0.68	Remote Similarity	NPC146239
0.68	Remote Similarity	NPC483095
0.6667	Remote Similarity	NPC483065
0.6667	Remote Similarity	NPC483079
0.6389	Remote Similarity	NPC483066
0.6301	Remote Similarity	NPC260886
0.6296	Remote Similarity	NPC273798
0.619	Remote Similarity	NPC144257
0.6184	Remote Similarity	NPC482995
0.5844	Remote Similarity	NPC61651
0.5753	Remote Similarity	NPC218855
0.575	Remote Similarity	NPC483098
0.5733	Remote Similarity	NPC483060
0.5641	Remote Similarity	NPC482999
0.5641	Remote Similarity	NPC483070
0.5634	Remote Similarity	NPC177680
0.5634	Remote Similarity	NPC153776
0.5513	Remote Similarity	NPC483061
0.5513	Remote Similarity	NPC483062
0.5375	Remote Similarity	NPC483000
0.5256	Remote Similarity	NPC483069
0.5238	Remote Similarity	NPC483099
0.5135	Remote Similarity	NPC27105
0.5122	Remote Similarity	NPC482994
0.5063	Remote Similarity	NPC268930

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC294050 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2867
0.1-0.2	6205
0.2-0.3	78
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