NPASS Compound

Natural Product: NPC246860

Natural Product ID	NPC246860
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	12-Deacetoxy-23-Hydroxyheteronemin
IUPAC Name	[(1S,4S,5aS,5bS,7aS,11aR,11bS,13aS,13bR)-1-acetyloxy-11a-(hydroxymethyl)-5b,8,8,13a-tetramethyl-1,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[2,1-e][2]benzofuran-4-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL574521
PubChem CID	11248811
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

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 79 83 0 0 0 0 0 0 0 0999 V2000 4.4329 -4.0371 3.7839 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5226 -3.6339 2.6997 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7378 -4.4035 2.1040 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5133 -2.3087 2.2877 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6840 -1.8354 1.2678 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6735 -0.8173 1.7628 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9964 -0.2479 0.5857 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4007 0.3185 0.8516 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3466 1.3794 1.8665 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1601 -0.8463 1.5170 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6694 -0.5521 1.4818 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0154 -0.4829 0.0225 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4549 -0.7457 -0.1792 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3807 0.0089 0.7418 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6538 -2.2335 0.1894 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9106 -0.6297 -1.6018 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1907 0.3699 -2.4234 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7286 0.5218 -2.1389 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4379 0.7254 -0.6380 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0575 2.0165 -0.2961 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0478 2.4118 1.0026 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9473 0.6453 -0.4867 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1913 1.7993 -1.0506 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1988 1.2965 -1.3766 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8933 0.6457 -0.2017 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5542 1.7366 0.5729 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9176 -0.2834 -0.8120 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4191 -1.3068 0.1000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6203 -1.6420 -0.3410 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9373 -0.8859 -1.4895 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1635 0.3335 -1.3150 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0443 0.9931 -2.5559 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6705 2.1837 -2.7831 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3616 2.6829 -1.8591 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5649 2.9195 -4.0952 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9514 -3.8142 4.7804 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6191 -5.1317 3.7885 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3849 -3.4707 3.7859 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0857 -2.7036 0.8990 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2265 -0.1075 2.4029 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0080 -1.3805 2.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7690 -1.1167 -0.1114 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3730 2.4102 1.5660 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1372 1.2730 2.6703 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6144 1.2456 2.4504 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9483 -1.8009 1.0409 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9355 -0.8368 2.6247 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1475 -1.4431 1.9277 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9132 0.3349 2.0614 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4705 -1.3621 -0.4483 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9675 0.7365 0.1089 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1898 -0.6546 1.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8947 0.4700 1.5987 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7627 -2.8216 -0.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5043 -2.6448 -0.3996 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8700 -2.3201 1.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9444 -1.6285 -2.1299 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9974 -0.3207 -1.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2406 0.0133 -3.4976 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7302 1.3620 -2.4740 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3627 1.3535 -2.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2416 -0.4462 -2.3879 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5394 2.8017 -0.9250 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1010 2.0253 -0.6579 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7468 3.3599 1.0885 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6626 -0.2324 -1.1558 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1790 2.7072 -0.4338 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6256 2.1104 -2.0311 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8099 2.1349 -1.7389 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0874 0.5597 -2.1980 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2990 2.2091 -0.1373 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8795 2.5857 0.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1467 1.4217 1.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4622 -0.8338 -1.6874 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3136 -2.3793 0.0693 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7797 0.8785 -0.5758 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0365 3.8796 -3.9260 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0932 2.3054 -4.8608 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6066 3.1758 -4.3856 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 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 13 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 20 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 28 5 1 0 25 7 1 0 31 27 1 0 22 8 1 0 19 12 1 0 1 36 1 0 1 37 1 0 1 38 1 0 5 39 1 6 6 40 1 0 6 41 1 0 7 42 1 6 9 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 12 50 1 6 14 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 20 63 1 0 20 64 1 0 21 65 1 0 22 66 1 6 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 26 71 1 0 26 72 1 0 26 73 1 0 27 74 1 6 29 75 1 0 31 76 1 1 35 77 1 0 35 78 1 0 35 79 1 0 M END

Standard InCHIKey	WJXDNRYRYAGILU-GJTCYCQFSA-N
Standard InCHI	InChI=1S/C29H44O6/c1-17(31)34-20-14-23-27(5)12-8-21-26(3,4)10-7-11-29(21,16-30)22(27)9-13-28(23,6)24-19(20)15-33-25(24)35-18(2)32/h15,20-25,30H,7-14,16H2,1-6H3/t20-,21-,22-,23-,24+,25-,27+,28-,29+/m0/s1
SMILES	CC(=O)O[C@H]1C[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(CO)[C@H]3CC[C@]2(C)[C@@H]2C1=CO[C@H]2OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.31	Volume:	512.19 ? Van der Waals volume.
Dense:	0.953	LogP:	2.629 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.893 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.258 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	27.0
TPSA:	82.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.537	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.172	Fsp³:	0.862
MCE-18:	96.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.43	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.184	Promiscuous compounds:	0.809

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.152	MDCK Permeability:	-4.993
Pgp-inhibitor:	0.652	Pgp-substrate:	0.013
PAMPA:	0.226 ? 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):	0.001
20% Bioavailability (F20%):	0.033	30% Bioavailability (F30%):	0.113
50% Bioavailability (F50%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071	MRP1:	0.607
Plasma Protein Binding (PPB):	75.877%	Volume Distribution (VD):	-0.141
Fu:	19.144% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.988
OATP1B3 inhibitor:	0.922	BCRP inhibitor:	0.38
BSEP inhibitor:	0.888

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.994	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.697
CYP2D6-inhibitor:	0.009	CYP2D6-substrate:	0.147
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.93
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.98
HLM stability:	0.214 ? 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):

8.675

Half-life (T1/2):

0.655

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.204
Human Hepatotoxicity (H-HT):	0.64	Drug-induced Liver Injury (DILI):	0.861
AMES Toxicity:	0.903	Rat Oral Acute Toxicity:	0.469
Maximum Recommended Daily Dose:	0.536	Skin Sensitization:	0.996
Carcinogencity:	0.942	Eye Corrosion:	0.005
Eye Irritation:	0.271	Respiratory Toxicity:	0.35
Drug-induced Neurotoxicity:	0.176	Ototoxicity:	0.384
Hematotoxicity:	0.585	Drug-induced Nephrotoxicity:	0.928
Genotoxicity:	0.885	RPMI-8226 Immunitoxicity:	0.075
A549 Cytotoxicity:	0.44	Hek293 Cytotoxicity:	0.333
BCF:	1.845 ? 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:	4.615 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.295 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.729 ? 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
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270579]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	Korean	n.a.	PMID[23489626]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621941]

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
IC50	6
MIC	6

Activity Type	# Activity
Individual protein	1
Cell line	4
Organism	6
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4391	Individual protein	Isocitrate lyase	Magnaporthe oryzae (strain 70-15 / FGSC 8958) (Rice blast fungus)(Pyricularia oryzae)	IC50	>	100.0	ug.mL-1	PMID[18198839]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3885	Cell line	CV-1	Chlorocebus aethiops	IC50	=	800.0	nM	PMID[26052978]
NPT376	Cell line	A498	Homo sapiens	IC50	=	700.0	nM	PMID[26052978]
NPT461	Cell line	PANC-1	Homo sapiens	IC50	=	400.0	nM	PMID[26052978]
NPT369	Cell line	ACHN	Homo sapiens	IC50	=	400.0	nM	PMID[26056748]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	100.0	ug.mL-1	DOI[10.6019/CHEMBL1201861]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	6.25	ug.mL-1	PMID[23829449]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.78	ug.mL-1	PMID[21035332]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	700.0	nM	PMID[23489626]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[18591277]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[19691312]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	Open TG-GATES in vivo data: Hematology

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 NPC246860 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	18657
0.1-0.2	27116
0.2-0.3	3906
0.3-0.4	156
0.4-0.5	16
0.5-0.6	2
0.6-0.7	2
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
0.7667	Intermediate Similarity	NPC164750
0.7077	Intermediate Similarity	NPC144069
0.6769	Remote Similarity	NPC163902
0.6716	Remote Similarity	NPC97867
0.5606	Remote Similarity	NPC120539
0.5588	Remote Similarity	NPC134077

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC246860 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6325
0.1-0.2	2789
0.2-0.3	36
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