NPASS Compound

Natural Product: NPC3915

Natural Product ID	NPC3915
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Oxo-Erythrodiol
IUPAC Name	(4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1H-picen-3-one
Synonyms	3-Oxo-Erythrodiol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1631831
PubChem CID	15127783
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 84 0 0 0 0 0 0 0 0999 V2000 -5.6028 0.7759 -1.7951 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9580 1.1363 -0.4933 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4586 2.4921 -0.0551 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2910 0.1620 0.6212 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8399 -1.1824 0.1826 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3410 -1.2956 -0.0914 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7098 -1.4935 1.2563 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2390 -1.6267 1.1607 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6014 -0.3853 0.6159 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6711 0.6889 1.6842 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3357 0.1427 -0.5589 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6879 0.8870 -1.4203 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7256 1.2754 -1.3642 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4047 0.7485 -0.1188 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8823 0.8919 -0.1401 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4013 0.9920 -1.5423 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2657 2.2750 0.4478 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7359 2.5142 0.3046 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5645 1.3358 0.6125 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7336 1.5246 0.9127 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0829 -0.0634 0.5847 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6622 -0.7275 1.8467 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5922 -0.8526 -0.5808 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6020 -0.0734 0.7437 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0213 -1.4737 0.7442 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6172 -1.3244 1.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8469 -0.5968 0.1679 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8162 -1.5303 -0.9898 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7862 -0.1329 -0.7953 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4688 1.1946 -0.5528 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2994 -2.5872 -0.9294 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0553 -2.9521 -1.3289 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8510 0.4703 -2.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1452 1.6677 -2.2245 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3431 -0.0251 -1.7388 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9789 3.2905 -0.6613 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5599 2.5570 -0.1054 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1824 2.5924 1.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7595 0.4912 1.5142 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3866 0.1394 0.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0670 -1.9166 0.9806 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4017 -1.5210 -0.7201 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0626 -0.6516 1.8869 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1424 -2.4316 1.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8619 -1.7094 2.2310 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9531 -2.5530 0.6562 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2112 0.6912 2.3641 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5261 0.4579 2.3450 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8931 1.6989 1.2656 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2489 1.2750 -2.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2107 0.8992 -2.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7779 2.4015 -1.3355 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0353 1.4395 0.6991 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1308 0.2153 -2.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9734 1.9531 -1.9615 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4974 1.1367 -1.5972 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7315 3.0698 -0.0813 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0065 2.2306 1.5179 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0127 3.3153 1.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9996 2.9217 -0.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6350 -1.8203 1.6458 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7513 -0.4575 1.8742 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1192 -0.4175 2.7388 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1335 -1.7955 -0.2691 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3783 -0.2875 -1.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7814 -1.2218 -1.2561 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4170 0.2798 1.8065 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5831 -2.0106 1.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1139 -1.9979 -0.2008 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1633 -2.3263 1.3936 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6253 -0.7287 2.1852 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6206 -2.5910 -0.6496 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0308 -1.3395 -1.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7500 -1.6084 -1.5740 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9510 -0.3179 -1.9038 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1926 1.8884 -1.3737 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1226 1.6539 0.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9271 -2.4415 -1.8453 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8422 -3.4003 -0.3646 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8997 -3.9051 -1.1003 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 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 11 29 1 0 29 30 1 0 6 31 1 6 31 32 1 0 30 2 1 0 29 6 1 0 27 9 1 0 27 14 1 0 24 15 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 10 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 1 16 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 22 61 1 0 22 62 1 0 22 63 1 0 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 1 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 6 30 76 1 0 30 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 M END

Standard InCHIKey	LCZGVWKWRGLAFX-CHMVMOPFSA-N
Standard InCHI	InChI=1S/C30H48O2/c1-25(2)14-16-30(19-31)17-15-28(6)20(21(30)18-25)8-9-23-27(5)12-11-24(32)26(3,4)22(27)10-13-29(23,28)7/h8,21-23,31H,9-19H2,1-7H3/t21-,22-,23+,27-,28+,29+,30+/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.37	Volume:	496.961 ? Van der Waals volume.
Dense:	0.886	LogP:	4.614 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.118 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.148 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.433	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.668	Fsp³:	0.9
MCE-18:	101.333 ? 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:	0.832	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.662	Promiscuous compounds:	0.282

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.152	MDCK Permeability:	-4.88
Pgp-inhibitor:	0.49	Pgp-substrate:	0.0
PAMPA:	0.813 ? 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%):	0.182	30% Bioavailability (F30%):	0.082
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995	MRP1:	0.85
Plasma Protein Binding (PPB):	97.293%	Volume Distribution (VD):	0.277
Fu:	3.702% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.425	BCRP inhibitor:	0.538
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.984	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.722
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.628
HLM stability:	0.642 ? 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):

8.922

Half-life (T1/2):

0.353

ADMET: Toxicity

hERG Blockers:	0.046	hERG Blockers (10um):	0.173
Human Hepatotoxicity (H-HT):	0.693	Drug-induced Liver Injury (DILI):	0.518
AMES Toxicity:	0.391	Rat Oral Acute Toxicity:	0.443
Maximum Recommended Daily Dose:	0.406	Skin Sensitization:	0.913
Carcinogencity:	0.911	Eye Corrosion:	0.04
Eye Irritation:	0.534	Respiratory Toxicity:	0.771
Drug-induced Neurotoxicity:	0.473	Ototoxicity:	0.484
Hematotoxicity:	0.8	Drug-induced Nephrotoxicity:	0.874
Genotoxicity:	0.876	RPMI-8226 Immunitoxicity:	0.08
A549 Cytotoxicity:	0.362	Hek293 Cytotoxicity:	0.443
BCF:	2.08 ? 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:	4.184 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.45 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.947 ? 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
NPO17642	Chondropetalum paniculatum	Species	Restionaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15081	Aleuroglyphus ovatus	Species	Acaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17642	Chondropetalum paniculatum	Species	Restionaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21797	Derris brevipes	Species	Fabaceae	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
Inhibition	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	1.17	%	PMID[20964318]

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 NPC3915 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	23058
0.1-0.2	22853
0.2-0.3	2982
0.3-0.4	739
0.4-0.5	186
0.5-0.6	27
0.6-0.7	5
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
0.7818	Intermediate Similarity	NPC142754
0.7167	Intermediate Similarity	NPC267517
0.6667	Remote Similarity	NPC101475
0.6613	Remote Similarity	NPC133954
0.6562	Remote Similarity	NPC191965
0.6308	Remote Similarity	NPC99254
0.6066	Remote Similarity	NPC82477
0.5942	Remote Similarity	NPC193750
0.5909	Remote Similarity	NPC80784
0.5806	Remote Similarity	NPC474488
0.5735	Remote Similarity	NPC474845
0.5735	Remote Similarity	NPC263272
0.5735	Remote Similarity	NPC480926
0.5694	Remote Similarity	NPC480922
0.5672	Remote Similarity	NPC267691
0.5652	Remote Similarity	NPC38754
0.5625	Remote Similarity	NPC196753
0.5588	Remote Similarity	NPC213412
0.5556	Remote Similarity	NPC190035
0.5538	Remote Similarity	NPC235341
0.5479	Remote Similarity	NPC480923
0.5441	Remote Similarity	NPC274050
0.5441	Remote Similarity	NPC162632
0.5429	Remote Similarity	NPC158141
0.5417	Remote Similarity	NPC105189
0.5397	Remote Similarity	NPC290598
0.5397	Remote Similarity	NPC30590
0.5303	Remote Similarity	NPC478657
0.5294	Remote Similarity	NPC246708
0.5294	Remote Similarity	NPC606009
0.5139	Remote Similarity	NPC173089
0.5075	Remote Similarity	NPC253807
0.5075	Remote Similarity	NPC195334
0.5075	Remote Similarity	NPC158662

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC3915 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7308
0.1-0.2	1778
0.2-0.3	61
0.3-0.4	2
0.4-0.5	0
0.5-0.6	1
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
0.507	Remote Similarity	NPD7645	Phase 2

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