NPASS Compound

Natural Product: NPC474970

Natural Product ID	NPC474970
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	12Beta-Acetoxyergost-5-Ene-3Beta,23-Diol
IUPAC Name	[(3S,8R,9S,10R,12R,13R,14S,17R)-3-hydroxy-17-[(2R,5R)-4-hydroxy-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-12-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL490526
PubChem CID	44566213
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols and derivatives

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 84 87 0 0 0 0 0 0 0 0999 V2000 -7.2344 0.7102 0.5666 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6483 1.3174 -0.6804 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1833 2.7087 -0.3839 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5798 0.4449 -1.2991 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1728 -0.8753 -1.6600 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4172 0.3775 -0.3659 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2969 -0.4811 -0.9105 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1236 -0.5284 0.0646 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6682 -1.1146 1.3318 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0541 -1.3361 -0.5891 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6598 -0.6680 -1.8832 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8105 -1.0146 -2.1115 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2450 -1.7011 -0.8701 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2066 -1.5087 0.1974 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5110 -0.4058 1.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5463 0.5739 0.5730 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8204 -0.2494 0.4518 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6616 -1.4314 -0.4293 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5222 -1.4782 -1.6569 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8584 -0.8745 -1.4329 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0812 0.0546 -0.5485 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0279 0.5904 0.3130 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7944 2.0167 -0.1542 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8942 2.5430 -1.0297 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2794 2.1420 -0.6674 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4436 0.6510 -0.3980 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8777 2.9322 0.3101 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6355 0.7568 1.7269 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1447 -0.9685 2.2974 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7140 -0.7427 3.5806 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2904 -0.0028 3.7503 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4067 -1.3504 4.7491 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0610 -2.7877 0.9944 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9291 1.6687 -0.1752 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6208 -0.2997 0.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0751 1.3635 0.8829 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5164 0.6879 1.4103 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4782 1.3870 -1.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7962 2.8039 0.6638 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4903 3.1187 -1.1350 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1022 3.3652 -0.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2418 0.9590 -2.2256 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3313 -1.4617 -0.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2103 -0.6711 -2.0544 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5877 -1.4267 -2.4244 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6787 -0.0254 0.6342 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6789 -1.5200 -1.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0268 -0.1015 -1.8937 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8287 0.5459 0.1926 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4903 -1.8006 1.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1226 -0.2625 1.9205 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9056 -1.5364 2.0078 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4757 -2.3305 -0.8427 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7801 0.4390 -1.6962 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2156 -1.0163 -2.7531 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9152 -1.6663 -3.0315 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3018 -0.0847 -2.3810 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2077 -2.8078 -1.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3177 0.1877 1.5035 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2090 1.0597 -0.3226 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7037 1.3357 1.3643 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8780 -0.6841 1.5170 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9646 -2.3750 0.1393 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6748 -2.5543 -1.9481 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0665 -1.0138 -2.5546 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7352 -1.2068 -2.0307 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6814 2.7151 0.7004 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8551 2.1281 -0.7490 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8601 3.6662 -0.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7271 2.3265 -2.1059 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9079 2.3298 -1.5933 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8728 0.4759 0.6152 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1375 0.1560 -1.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1754 3.7969 -0.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3944 -0.0273 1.9215 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8063 0.5901 2.4413 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0100 1.7593 1.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2287 -0.7094 5.1328 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6978 -1.5906 5.5507 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8899 -2.3264 4.4471 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8721 -3.4722 0.6752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2187 -2.6369 2.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8853 -3.3225 0.7787 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4199 1.7645 0.6653 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 22 28 1 0 15 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 14 33 1 0 6 34 1 0 14 10 1 0 18 13 1 0 22 17 1 0 26 21 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 5 45 1 0 6 46 1 0 7 47 1 0 7 48 1 0 8 49 1 0 9 50 1 0 9 51 1 0 9 52 1 0 10 53 1 0 11 54 1 0 11 55 1 0 12 56 1 0 12 57 1 0 13 58 1 0 15 59 1 0 16 60 1 0 16 61 1 0 17 62 1 0 18 63 1 0 19 64 1 0 19 65 1 0 20 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 27 74 1 0 28 75 1 0 28 76 1 0 28 77 1 0 32 78 1 0 32 79 1 0 32 80 1 0 33 81 1 0 33 82 1 0 33 83 1 0 34 84 1 0 M END

Standard InCHIKey	FWOFLAFLCPNJMF-XMZRPQIDSA-N
Standard InCHI	InChI=1S/C30H50O4/c1-17(2)19(4)27(33)14-18(3)24-10-11-25-23-9-8-21-15-22(32)12-13-29(21,6)26(23)16-28(30(24,25)7)34-20(5)31/h8,17-19,22-28,32-33H,9-16H2,1-7H3/t18-,19-,22+,23+,24-,25+,26+,27?,28-,29+,30-/m1/s1
SMILES	CC(C)C(C)C(CC(C)C1CCC2C1(C(CC3C2CC=C4C3(CCC(C4)O)C)OC(=O)C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	474.37	Volume:	523.098 ? Van der Waals volume.
Dense:	0.907	LogP:	4.767 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.286 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.402 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	21.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.358	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.846	Fsp³:	0.9
MCE-18:	75.789 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.674	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.025 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.267	Promiscuous compounds:	0.009

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.975	MDCK Permeability:	-4.745
Pgp-inhibitor:	0.0	Pgp-substrate:	0.266
PAMPA:	0.595 ? 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%):	0.001	30% Bioavailability (F30%):	0.037
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.612	MRP1:	1.0
Plasma Protein Binding (PPB):	63.904%	Volume Distribution (VD):	-0.262
Fu:	35.519% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.303	BCRP inhibitor:	0.007
BSEP inhibitor:	0.668

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.681	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.023
CYP2B6-substrate:	0.204	CYP2C8-inhibitor:	1.0
HLM stability:	0.73 ? 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):

12.805

Half-life (T1/2):

1.367

ADMET: Toxicity

hERG Blockers:	0.196	hERG Blockers (10um):	0.66
Human Hepatotoxicity (H-HT):	0.654	Drug-induced Liver Injury (DILI):	0.088
AMES Toxicity:	0.037	Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.834	Skin Sensitization:	0.038
Carcinogencity:	0.131	Eye Corrosion:	0.0
Eye Irritation:	0.02	Respiratory Toxicity:	0.247
Drug-induced Neurotoxicity:	0.252	Ototoxicity:	0.974
Hematotoxicity:	0.072	Drug-induced Nephrotoxicity:	0.176
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.04
A549 Cytotoxicity:	0.269	Hek293 Cytotoxicity:	0.392
BCF:	1.391 ? 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:	4.094 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.81 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.893 ? 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
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608844]
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	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
Activity	1
IZ	1

Activity Type	# Activity
Individual protein	1
Organism	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT13	Individual protein	Tyrosine-protein kinase LCK	Homo sapiens	Activity	=	42.0	%	PMID[18077363]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	3.0	mm	PMID[18077363]

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 NPC474970 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	17211
0.1-0.2	25815
0.2-0.3	6507
0.3-0.4	241
0.4-0.5	59
0.5-0.6	17
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	Natural Product ID
0.5735	Remote Similarity	NPC475032
0.5645	Remote Similarity	NPC162742
0.5645	Remote Similarity	NPC304309
0.5645	Remote Similarity	NPC470228
0.5352	Remote Similarity	NPC475033
0.5312	Remote Similarity	NPC221758
0.5231	Remote Similarity	NPC136188
0.5231	Remote Similarity	NPC28657
0.5205	Remote Similarity	NPC276103
0.5152	Remote Similarity	NPC230301
0.5147	Remote Similarity	NPC472265
0.5147	Remote Similarity	NPC59453
0.5077	Remote Similarity	NPC22105
0.5077	Remote Similarity	NPC34019
0.5077	Remote Similarity	NPC107059
0.5077	Remote Similarity	NPC600590
0.5075	Remote Similarity	NPC51014

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474970 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6438
0.1-0.2	2486
0.2-0.3	215
0.3-0.4	6
0.4-0.5	1
0.5-0.6	3
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
0.5312	Remote Similarity	NPD4786	Phase 1
0.5231	Remote Similarity	NPD6942	Phase 4
0.5152	Remote Similarity	NPD7339	Approved

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