NPASS Compound

Structure

CID12156 OpenBabel06191715342D 27 26 0 0 0 0 0 0 0 0999 V2000 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 2 0 0 0 0 23 27 1 0 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.34
Volume:	444.758
LogP:	9.042
LogD:	4.502
LogS:	-6.997
# Rotatable Bonds:	22
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.122
Synthetic Accessibility Score:	1.883
Fsp3:	0.917
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.94
MDCK Permeability:	1.1620074474194553e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	96.3260269165039%
Volume Distribution (VD):	1.022
Pgp-substrate:	0.9933433532714844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.158
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.319
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.264
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	4.954
Half-life (T1/2):	0.269

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.016
Drug-inuced Liver Injury (DILI):	0.162
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.978
Carcinogencity:	0.07
Eye Corrosion:	0.998
Eye Irritation:	0.95
Respiratory Toxicity:	0.885

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC12156

Natural Product ID:	NPC12156
*Common Name:**	Dodecanoic Anhydride
IUPAC Name:	dodecanoyl dodecanoate
Synonyms:	Dodecanoic Anhydride
Standard InCHIKey:	NWADXBLMWHFGGU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H46O3/c1-3-5-7-9-11-13-15-17-19-21-23(25)27-24(26)22-20-18-16-14-12-10-8-6-4-2/h3-22H2,1-2H3
SMILES:	CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL420797
PubChem CID:	69527
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	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	NP ID	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	2

Activity Type	# Activity
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1180	Protein Complex	Protein farnesyltransferase	Homo sapiens	IC50	=	854000.0	nM	PMID[550749]
NPT1181	Protein Complex	Geranylgeranyl transferase type I	Homo sapiens	IC50	=	229000.0	nM	PMID[550749]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC12156 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1030
0.1-0.2	15216
0.2-0.3	15684
0.3-0.4	8338
0.4-0.5	1915
0.5-0.6	285
0.6-0.7	115
0.7-0.8	61
0.8-0.85	21
0.85-0.9	15
0.9-0.95	16
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC236579
0.9487	High Similarity	NPC203531
0.9474	High Similarity	NPC28598
0.9474	High Similarity	NPC161097
0.925	High Similarity	NPC317128
0.9024	High Similarity	NPC287231
0.9024	High Similarity	NPC47363
0.8974	High Similarity	NPC256163
0.8974	High Similarity	NPC40597
0.8974	High Similarity	NPC165533
0.8974	High Similarity	NPC250028
0.8974	High Similarity	NPC149299
0.8947	High Similarity	NPC201622
0.8947	High Similarity	NPC22903
0.8947	High Similarity	NPC305660
0.8947	High Similarity	NPC54980
0.875	High Similarity	NPC216630
0.875	High Similarity	NPC196924
0.875	High Similarity	NPC307783
0.875	High Similarity	NPC149184
0.875	High Similarity	NPC209970
0.875	High Similarity	NPC53541
0.875	High Similarity	NPC171736
0.8718	High Similarity	NPC219536
0.8718	High Similarity	NPC31551
0.8718	High Similarity	NPC80234
0.8718	High Similarity	NPC223249
0.8649	High Similarity	NPC156630
0.8537	High Similarity	NPC67462
0.8372	Intermediate Similarity	NPC30195
0.8372	Intermediate Similarity	NPC12438
0.8333	Intermediate Similarity	NPC74845
0.825	Intermediate Similarity	NPC154186
0.825	Intermediate Similarity	NPC301696
0.825	Intermediate Similarity	NPC113928
0.825	Intermediate Similarity	NPC201844
0.825	Intermediate Similarity	NPC279026
0.825	Intermediate Similarity	NPC14227
0.825	Intermediate Similarity	NPC301585
0.825	Intermediate Similarity	NPC261080
0.8222	Intermediate Similarity	NPC26253
0.8205	Intermediate Similarity	NPC128996
0.814	Intermediate Similarity	NPC8219
0.8043	Intermediate Similarity	NPC55678
0.8	Intermediate Similarity	NPC106872
0.7955	Intermediate Similarity	NPC52700
0.7955	Intermediate Similarity	NPC63182
0.7955	Intermediate Similarity	NPC105329
0.7955	Intermediate Similarity	NPC145045
0.7949	Intermediate Similarity	NPC80396
0.7949	Intermediate Similarity	NPC154642
0.7949	Intermediate Similarity	NPC80641
0.7907	Intermediate Similarity	NPC255837
0.7907	Intermediate Similarity	NPC19305
0.7872	Intermediate Similarity	NPC287811
0.7805	Intermediate Similarity	NPC183424
0.7805	Intermediate Similarity	NPC214610
0.7805	Intermediate Similarity	NPC118968
0.7805	Intermediate Similarity	NPC294085
0.7778	Intermediate Similarity	NPC328497
0.7778	Intermediate Similarity	NPC21844
0.7778	Intermediate Similarity	NPC324004
0.7778	Intermediate Similarity	NPC249754
0.7778	Intermediate Similarity	NPC326957
0.7727	Intermediate Similarity	NPC273545
0.7708	Intermediate Similarity	NPC310746
0.7692	Intermediate Similarity	NPC301398
0.7692	Intermediate Similarity	NPC196442
0.7692	Intermediate Similarity	NPC223374
0.7692	Intermediate Similarity	NPC86545
0.7674	Intermediate Similarity	NPC129972
0.7674	Intermediate Similarity	NPC71317
0.7674	Intermediate Similarity	NPC301528
0.7609	Intermediate Similarity	NPC324793
0.7609	Intermediate Similarity	NPC477878
0.7561	Intermediate Similarity	NPC268826
0.7556	Intermediate Similarity	NPC308301
0.75	Intermediate Similarity	NPC155263
0.7442	Intermediate Similarity	NPC103286
0.7442	Intermediate Similarity	NPC163746
0.7436	Intermediate Similarity	NPC286498
0.7436	Intermediate Similarity	NPC154396
0.7436	Intermediate Similarity	NPC57499
0.74	Intermediate Similarity	NPC23155
0.74	Intermediate Similarity	NPC320588
0.74	Intermediate Similarity	NPC469937
0.74	Intermediate Similarity	NPC53463
0.7381	Intermediate Similarity	NPC81263
0.7333	Intermediate Similarity	NPC55023
0.7292	Intermediate Similarity	NPC305182
0.7292	Intermediate Similarity	NPC90904
0.7273	Intermediate Similarity	NPC176500
0.7255	Intermediate Similarity	NPC200845
0.7255	Intermediate Similarity	NPC10316
0.7255	Intermediate Similarity	NPC223677
0.7255	Intermediate Similarity	NPC128061
0.7255	Intermediate Similarity	NPC28779
0.7234	Intermediate Similarity	NPC216130
0.72	Intermediate Similarity	NPC139545
0.72	Intermediate Similarity	NPC309606
0.72	Intermediate Similarity	NPC39633
0.7179	Intermediate Similarity	NPC286695
0.7179	Intermediate Similarity	NPC322892
0.7174	Intermediate Similarity	NPC314679
0.7143	Intermediate Similarity	NPC314084
0.7143	Intermediate Similarity	NPC262968
0.7083	Intermediate Similarity	NPC304162
0.7083	Intermediate Similarity	NPC250919
0.7073	Intermediate Similarity	NPC134782
0.7	Intermediate Similarity	NPC161366
0.6957	Remote Similarity	NPC469781
0.6939	Remote Similarity	NPC224227
0.6923	Remote Similarity	NPC149101
0.6923	Remote Similarity	NPC225318
0.6923	Remote Similarity	NPC228473
0.6923	Remote Similarity	NPC76608
0.6923	Remote Similarity	NPC12904
0.6923	Remote Similarity	NPC16578
0.6923	Remote Similarity	NPC40965
0.6905	Remote Similarity	NPC14608
0.6875	Remote Similarity	NPC131770
0.6875	Remote Similarity	NPC200618
0.6863	Remote Similarity	NPC72722
0.6863	Remote Similarity	NPC71761
0.6829	Remote Similarity	NPC289344
0.6829	Remote Similarity	NPC155872
0.6809	Remote Similarity	NPC282440
0.68	Remote Similarity	NPC470410
0.68	Remote Similarity	NPC470412
0.675	Remote Similarity	NPC175342
0.6744	Remote Similarity	NPC73245
0.6731	Remote Similarity	NPC25417
0.6731	Remote Similarity	NPC88966
0.6731	Remote Similarity	NPC85813
0.6731	Remote Similarity	NPC290563
0.6731	Remote Similarity	NPC6095
0.6731	Remote Similarity	NPC424
0.6731	Remote Similarity	NPC87394
0.6731	Remote Similarity	NPC154245
0.6731	Remote Similarity	NPC281972
0.6731	Remote Similarity	NPC87564
0.6731	Remote Similarity	NPC32467
0.6731	Remote Similarity	NPC261831
0.6727	Remote Similarity	NPC469924
0.6727	Remote Similarity	NPC470363
0.6667	Remote Similarity	NPC248763
0.6667	Remote Similarity	NPC168982
0.6667	Remote Similarity	NPC325452
0.6607	Remote Similarity	NPC229252
0.6607	Remote Similarity	NPC45097
0.6607	Remote Similarity	NPC143857
0.6591	Remote Similarity	NPC94368
0.6585	Remote Similarity	NPC49615
0.6538	Remote Similarity	NPC294548
0.6538	Remote Similarity	NPC36061
0.6538	Remote Similarity	NPC1813
0.6538	Remote Similarity	NPC321062
0.6538	Remote Similarity	NPC70387
0.6538	Remote Similarity	NPC139029
0.6531	Remote Similarity	NPC180534
0.6522	Remote Similarity	NPC289686
0.6512	Remote Similarity	NPC158179
0.6481	Remote Similarity	NPC477201
0.6481	Remote Similarity	NPC18951
0.6471	Remote Similarity	NPC100096
0.6458	Remote Similarity	NPC166287
0.6458	Remote Similarity	NPC172042
0.6429	Remote Similarity	NPC226602
0.6429	Remote Similarity	NPC472020
0.6429	Remote Similarity	NPC472019
0.6415	Remote Similarity	NPC319589
0.641	Remote Similarity	NPC221192
0.641	Remote Similarity	NPC153439
0.641	Remote Similarity	NPC79887
0.641	Remote Similarity	NPC29561
0.641	Remote Similarity	NPC196434
0.641	Remote Similarity	NPC222997
0.641	Remote Similarity	NPC42403
0.641	Remote Similarity	NPC4962
0.64	Remote Similarity	NPC223675
0.6383	Remote Similarity	NPC76051
0.6379	Remote Similarity	NPC235788
0.6379	Remote Similarity	NPC54925
0.6364	Remote Similarity	NPC316546
0.6346	Remote Similarity	NPC281245
0.6346	Remote Similarity	NPC92114
0.6346	Remote Similarity	NPC18357
0.6341	Remote Similarity	NPC147054
0.6341	Remote Similarity	NPC328710
0.6341	Remote Similarity	NPC18224
0.6316	Remote Similarity	NPC472021
0.6275	Remote Similarity	NPC50457
0.6271	Remote Similarity	NPC314103
0.6271	Remote Similarity	NPC68343
0.6271	Remote Similarity	NPC328089
0.6222	Remote Similarity	NPC3531
0.6207	Remote Similarity	NPC469922
0.6207	Remote Similarity	NPC469923
0.6207	Remote Similarity	NPC201939
0.62	Remote Similarity	NPC68577

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC12156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1537
0.1-0.2	5180
0.2-0.3	1685
0.3-0.4	534
0.4-0.5	146
0.5-0.6	38
0.6-0.7	18
0.7-0.8	7
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9459	High Similarity	NPD3206	Approved
0.9024	High Similarity	NPD2699	Approved
0.875	High Similarity	NPD2270	Approved
0.825	Intermediate Similarity	NPD9448	Phase 2
0.825	Intermediate Similarity	NPD633	Phase 3
0.814	Intermediate Similarity	NPD3199	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6125	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD9655	Approved
0.7674	Intermediate Similarity	NPD387	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3728	Approved
0.74	Intermediate Similarity	NPD3730	Approved
0.7174	Intermediate Similarity	NPD634	Phase 3
0.7143	Intermediate Similarity	NPD28	Approved
0.7143	Intermediate Similarity	NPD29	Approved
0.7	Intermediate Similarity	NPD3186	Phase 1
0.6905	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4266	Approved
0.6731	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3195	Phase 2
0.6731	Remote Similarity	NPD3196	Approved
0.6731	Remote Similarity	NPD3194	Approved
0.6538	Remote Similarity	NPD3172	Approved
0.6531	Remote Similarity	NPD622	Approved
0.6531	Remote Similarity	NPD2266	Phase 2
0.6458	Remote Similarity	NPD9430	Approved
0.6458	Remote Similarity	NPD9431	Approved
0.6429	Remote Similarity	NPD9447	Approved
0.6222	Remote Similarity	NPD9450	Approved
0.6222	Remote Similarity	NPD77	Approved
0.614	Remote Similarity	NPD3198	Approved
0.6122	Remote Similarity	NPD3174	Discontinued
0.6111	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9513	Phase 1
0.5882	Remote Similarity	NPD5343	Approved
0.5873	Remote Similarity	NPD8278	Approved
0.5849	Remote Similarity	NPD9638	Phase 2
0.5814	Remote Similarity	NPD900	Approved
0.5781	Remote Similarity	NPD8277	Approved
0.5781	Remote Similarity	NPD3725	Approved
0.5781	Remote Similarity	NPD3726	Approved
0.5769	Remote Similarity	NPD3173	Approved
0.5745	Remote Similarity	NPD7536	Approved
0.5738	Remote Similarity	NPD7909	Approved
0.5738	Remote Similarity	NPD3197	Phase 1
0.561	Remote Similarity	NPD62	Approved
0.5606	Remote Similarity	NPD5777	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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