NPASS Compound

Natural Product: NPC517736

Natural Product ID	NPC517736
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RTJZUCGIUVBZCN-UHFFFAOYSA-N
IUPAC Name	octadeca-6,11-dienoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 52 51 0 0 0 0 0 0 0 0999 V2000 6.5111 -1.4862 -0.5684 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4390 -1.4455 -1.5921 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6044 -0.2288 -1.6697 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7675 0.1454 -0.4987 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5348 0.4012 0.7576 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5521 0.8283 1.8853 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9074 2.0455 1.3895 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6320 2.1883 1.1943 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6415 1.1362 1.4455 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0884 0.8140 0.1678 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0782 -0.3013 0.4311 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0438 0.1430 1.4423 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3073 0.3251 1.4653 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4236 0.1896 0.5151 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0699 -0.2555 -0.8285 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1142 -0.4166 -1.8727 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1635 -1.3894 -1.5500 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1032 -1.0802 -0.4891 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3465 0.0712 -0.1003 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7849 -2.1255 0.1451 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3310 -2.1778 0.2859 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8217 -0.4814 -0.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4309 -1.9229 -1.0605 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7620 -2.3322 -1.4810 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9171 -1.5667 -2.6095 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8845 -0.3466 -2.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1899 0.6887 -1.9435 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2232 1.0938 -0.8114 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9883 -0.6662 -0.3467 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2131 1.2528 0.6296 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9894 -0.5141 1.1826 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 1.1062 2.7737 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9456 0.0061 2.1934 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6083 2.8927 1.1757 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2250 3.1455 0.8163 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1271 0.2265 1.7917 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0563 1.5685 2.2134 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6537 1.7464 -0.1065 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6362 0.5558 -0.6182 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4464 -1.1713 0.8948 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4342 -0.6768 -0.5130 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5080 0.3442 2.4371 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6826 0.6945 2.5013 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0443 1.1404 0.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1171 -0.5746 1.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2349 0.4186 -1.2420 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5831 -1.2862 -0.7456 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5736 -0.8080 -2.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5171 0.5747 -2.2241 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7587 -1.6995 -2.4667 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6164 -2.3771 -1.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3410 -1.9786 0.9805 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 3 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 3 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 1 21 1 0 1 22 1 0 1 23 1 0 2 24 1 0 2 25 1 0 3 26 1 0 3 27 1 0 4 28 1 0 4 29 1 0 5 30 1 0 5 31 1 0 6 32 1 0 6 33 1 0 7 34 1 0 8 35 1 0 9 36 1 0 9 37 1 0 10 38 1 0 10 39 1 0 11 40 1 0 11 41 1 0 12 42 1 0 13 43 1 0 14 44 1 0 14 45 1 0 15 46 1 0 15 47 1 0 16 48 1 0 16 49 1 0 17 50 1 0 17 51 1 0 20 52 1 0 M END

Standard InCHIKey	RTJZUCGIUVBZCN-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8,12-13H,2-6,9-11,14-17H2,1H3,(H,19,20)
SMILES	CCCCCCC=CCCCC=CCCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	280.24	Volume:	329.555 ? Van der Waals volume.
Dense:	0.85	LogP:	7.021 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.668 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.57 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	3.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.318	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.342	Fsp³:	0.722
MCE-18:	0.0 ? 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:	0.059	Fluc inhibitor:	0.23 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.012 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.996	Promiscuous compounds:	0.882

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.155	MDCK Permeability:	-4.832
Pgp-inhibitor:	0.001	Pgp-substrate:	0.003
PAMPA:	0.067 ? 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):	0.141
20% Bioavailability (F20%):	0.095	30% Bioavailability (F30%):	0.604
50% Bioavailability (F50%):	0.185

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109	MRP1:	0.976
Plasma Protein Binding (PPB):	98.447%	Volume Distribution (VD):	-0.77
Fu:	0.928% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.416
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.043
BSEP inhibitor:	0.694

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.16	CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.147	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.001 ? 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):

5.093

Half-life (T1/2):

0.381

ADMET: Toxicity

hERG Blockers:	0.192	hERG Blockers (10um):	0.319
Human Hepatotoxicity (H-HT):	0.172	Drug-induced Liver Injury (DILI):	0.001
AMES Toxicity:	0.116	Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.094	Skin Sensitization:	1.0
Carcinogencity:	0.052	Eye Corrosion:	0.999
Eye Irritation:	0.998	Respiratory Toxicity:	0.613
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.266
Hematotoxicity:	0.019	Drug-induced Nephrotoxicity:	0.452
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.262	Hek293 Cytotoxicity:	0.095
BCF:	1.15 ? 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:	3.963 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.389 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.642 ? 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
NPO10745	Stereospermum personatum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309309]
NPO10745	Stereospermum personatum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10745	Stereospermum personatum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10745	Stereospermum personatum	Species	Bignoniaceae	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

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

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 NPC517736 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	37934
0.1-0.2	10085
0.2-0.3	1419
0.3-0.4	222
0.4-0.5	85
0.5-0.6	45
0.6-0.7	43
0.7-0.8	1
0.8-0.85	8
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC92114
0.8929	High Similarity	NPC424
0.8929	High Similarity	NPC36061
0.8929	High Similarity	NPC69510
0.8929	High Similarity	NPC77272
0.8929	High Similarity	NPC290563
0.8929	High Similarity	NPC139029
0.8929	High Similarity	NPC281972
0.8929	High Similarity	NPC261831
0.8929	High Similarity	NPC87564
0.8571	High Similarity	NPC281245
0.8333	Intermediate Similarity	NPC5413
0.8065	Intermediate Similarity	NPC154245
0.8065	Intermediate Similarity	NPC85813
0.8065	Intermediate Similarity	NPC223697
0.8065	Intermediate Similarity	NPC6095
0.8	Intermediate Similarity	NPC95145
0.8	Intermediate Similarity	NPC325642
0.8	Intermediate Similarity	NPC65174
0.7742	Intermediate Similarity	NPC321062
0.75	Intermediate Similarity	NPC59051
0.7188	Intermediate Similarity	NPC91495
0.697	Remote Similarity	NPC52955
0.697	Remote Similarity	NPC88966
0.697	Remote Similarity	NPC25417
0.697	Remote Similarity	NPC1813
0.6875	Remote Similarity	NPC149821
0.6786	Remote Similarity	NPC171736
0.6786	Remote Similarity	NPC301585
0.6786	Remote Similarity	NPC261080
0.6786	Remote Similarity	NPC132565
0.6786	Remote Similarity	NPC209970
0.6786	Remote Similarity	NPC216630
0.6786	Remote Similarity	NPC201844
0.6786	Remote Similarity	NPC301696
0.6786	Remote Similarity	NPC196924
0.6786	Remote Similarity	NPC307783
0.6786	Remote Similarity	NPC154186
0.6786	Remote Similarity	NPC149184
0.6786	Remote Similarity	NPC279026
0.6786	Remote Similarity	NPC113928
0.6786	Remote Similarity	NPC14227
0.6757	Remote Similarity	NPC477201
0.6667	Remote Similarity	NPC70387
0.6429	Remote Similarity	NPC155263
0.641	Remote Similarity	NPC243532
0.6364	Remote Similarity	NPC207292
0.6316	Remote Similarity	NPC106851
0.6316	Remote Similarity	NPC282788
0.6316	Remote Similarity	NPC274927
0.625	Remote Similarity	NPC68343
0.625	Remote Similarity	NPC328089
0.6216	Remote Similarity	NPC487561
0.6216	Remote Similarity	NPC606120
0.6154	Remote Similarity	NPC179764
0.6129	Remote Similarity	NPC180534
0.6129	Remote Similarity	NPC611531
0.6071	Remote Similarity	NPC175342
0.6	Remote Similarity	NPC251042
0.6	Remote Similarity	NPC255863
0.6	Remote Similarity	NPC473863
0.6	Remote Similarity	NPC174447
0.6	Remote Similarity	NPC136164
0.6	Remote Similarity	NPC122521
0.6	Remote Similarity	NPC245947
0.5854	Remote Similarity	NPC318420
0.5854	Remote Similarity	NPC326268
0.5789	Remote Similarity	NPC225929
0.5758	Remote Similarity	NPC34416
0.5714	Remote Similarity	NPC214610
0.5714	Remote Similarity	NPC118968
0.5714	Remote Similarity	NPC183424
0.5714	Remote Similarity	NPC48162
0.5714	Remote Similarity	NPC294085
0.561	Remote Similarity	NPC323597
0.561	Remote Similarity	NPC211752
0.561	Remote Similarity	NPC318814
0.561	Remote Similarity	NPC320669
0.561	Remote Similarity	NPC323498
0.5588	Remote Similarity	NPC129972
0.5588	Remote Similarity	NPC8219
0.5588	Remote Similarity	NPC301528
0.5588	Remote Similarity	NPC71317
0.5588	Remote Similarity	NPC163746
0.5588	Remote Similarity	NPC103286
0.5556	Remote Similarity	NPC174368
0.5476	Remote Similarity	NPC317583
0.5429	Remote Similarity	NPC18712
0.5429	Remote Similarity	NPC74845
0.5357	Remote Similarity	NPC134782
0.5357	Remote Similarity	NPC268826
0.5349	Remote Similarity	NPC320642
0.5349	Remote Similarity	NPC329550
0.5294	Remote Similarity	NPC117572
0.5294	Remote Similarity	NPC262968
0.5278	Remote Similarity	NPC87394
0.5278	Remote Similarity	NPC324004
0.5278	Remote Similarity	NPC328497
0.5278	Remote Similarity	NPC602547
0.5263	Remote Similarity	NPC40082
0.5238	Remote Similarity	NPC187777
0.5227	Remote Similarity	NPC323045
0.5227	Remote Similarity	NPC49863
0.5227	Remote Similarity	NPC317881
0.5152	Remote Similarity	NPC55023
0.5152	Remote Similarity	NPC21844
0.5135	Remote Similarity	NPC174560
0.5135	Remote Similarity	NPC125312
0.5122	Remote Similarity	NPC28205
0.5111	Remote Similarity	NPC322461

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC517736 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6640
0.1-0.2	2242
0.2-0.3	200
0.3-0.4	41
0.4-0.5	8
0.5-0.6	7
0.6-0.7	6
0.7-0.8	1
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD3195	Phase 2
0.8929	High Similarity	NPD3196	Approved
0.8333	Intermediate Similarity	NPD3173	Phase 4
0.8065	Intermediate Similarity	NPD4266	Phase 2
0.7143	Intermediate Similarity	NPD3194	Phase 4
0.697	Remote Similarity	NPD3172	Approved
0.6786	Remote Similarity	NPD2270	Pre-clinical
0.6786	Remote Similarity	NPD633	Phase 3
0.6786	Remote Similarity	NPD9448	Phase 2
0.6667	Remote Similarity	NPD39	Phase 4
0.6129	Remote Similarity	NPD622	Pre-clinical
0.5714	Remote Similarity	NPD9655	Phase 4
0.5294	Remote Similarity	NPD28	Approved
0.5294	Remote Similarity	NPD29	Phase 4
0.5294	Remote Similarity	NPD4222	Phase 3
0.5278	Remote Similarity	NPD3197	Phase 1
0.5278	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5227	Remote Similarity	NPD4247	Clinical (unspecified phase)

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