NPASS Compound

Natural Product: NPC218140

Natural Product ID	NPC218140
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZFYMKPNQPGHLAR-GJMRBZRTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102230698
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

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 72 75 0 0 0 0 0 0 0 0999 V2000 -6.7747 -1.4282 -4.1739 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1540 -2.1820 -3.0095 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3218 -1.5855 -2.1943 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6782 -2.2763 -1.0278 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5352 -3.4793 -0.7113 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6046 -4.3035 -1.9787 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5688 -3.6035 -2.8882 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0406 -3.8538 0.4975 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8387 -5.1010 0.7198 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5889 -3.1801 1.8004 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8899 -2.9311 -0.3319 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6256 -1.3479 -0.0078 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4590 -0.7032 0.3648 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2307 -0.8803 -0.2054 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0918 -0.2160 0.1950 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1497 0.6771 1.2147 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0030 1.4299 1.6896 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2121 1.3510 1.1794 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3295 2.1582 1.7285 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5328 2.0798 1.2175 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6906 2.8177 1.6701 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4876 3.6030 2.6560 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0069 2.7185 1.0905 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3481 1.9599 0.0785 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6611 1.8470 -0.5178 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8773 0.9906 -1.5702 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1265 0.8778 -2.1485 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1899 1.6138 -1.6951 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9878 2.4724 -0.6461 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7188 2.5847 -0.0600 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0442 3.2179 -0.1808 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8363 4.1017 0.8933 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4638 1.5186 -2.2640 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1103 3.0055 2.7926 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3985 0.8636 1.8023 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5392 0.2294 1.4360 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7719 0.3990 2.0011 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0341 1.2600 3.0558 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1862 -2.1107 -4.9212 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5392 -0.7419 -3.7794 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9402 -0.8606 -4.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1020 -0.5264 -2.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7064 -2.6418 -1.4188 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8433 -5.3632 -1.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6047 -4.2654 -2.4772 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6250 -3.6833 -2.4962 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5819 -4.0567 -3.9035 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6277 -5.5051 1.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5767 -5.9144 0.0101 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9390 -4.9516 0.6872 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8791 -2.1065 1.8027 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0681 -3.6240 2.6808 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4773 -3.2099 1.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1345 -1.5872 -1.0294 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1690 -0.4278 -0.3216 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1102 2.1202 2.5273 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3697 0.6847 0.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6430 1.3844 0.3767 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7885 3.3335 1.5416 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5327 1.3478 -0.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0475 0.4013 -1.9400 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2783 0.2060 -2.9655 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6058 3.2725 0.7623 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7259 3.5763 1.8684 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9842 4.7936 0.7070 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7332 4.7783 1.0215 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1282 2.3038 -2.1962 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7370 2.6917 3.6754 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4181 1.5922 2.6179 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1015 1.5572 3.5560 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5842 2.1671 2.6843 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6904 0.7141 3.7806 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 5 8 1 0 8 9 1 0 8 10 1 0 8 11 1 0 4 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 28 33 1 0 19 34 1 0 16 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 7 2 1 0 36 13 1 0 11 5 1 0 30 25 1 0 1 39 1 0 1 40 1 0 1 41 1 0 3 42 1 0 4 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 9 48 1 0 9 49 1 0 9 50 1 0 10 51 1 0 10 52 1 0 10 53 1 0 14 54 1 0 15 55 1 0 17 56 1 0 18 57 1 0 20 58 1 0 23 59 1 0 24 60 1 0 26 61 1 0 27 62 1 0 30 63 1 0 32 64 1 0 32 65 1 0 32 66 1 0 33 67 1 0 34 68 1 0 35 69 1 0 38 70 1 0 38 71 1 0 38 72 1 0 M END

Standard InCHIKey	ZFYMKPNQPGHLAR-GJMRBZRTSA-N
Standard InCHI	InChI=1S/C31H34O7/c1-20-14-15-31(30(2,3)38-31)29(16-20)37-26-13-9-22(18-28(26)36-5)7-11-24(33)19-23(32)10-6-21-8-12-25(34)27(17-21)35-4/h6-13,16-19,29,33-34H,14-15H2,1-5H3/b10-6+,11-7+,24-19-
SMILES	CC1=CC(C2(CC1)C(C)(C)O2)Oc1ccc(/C=C/C(=C/C(=O)/C=C/c2ccc(c(c2)OC)O)/O)cc1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.23	Volume:	543.037 ? Van der Waals volume.
Dense:	0.954	LogP:	4.287 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.493 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.508 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	25.0
TPSA:	97.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.134	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.457	Fsp³:	0.323
MCE-18:	118.829 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.214 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.988 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.256	Promiscuous compounds:	0.065

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.152	MDCK Permeability:	-4.837
Pgp-inhibitor:	0.992	Pgp-substrate:	0.002
PAMPA:	0.006 ? 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):	0.004
20% Bioavailability (F20%):	0.99	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.007
Plasma Protein Binding (PPB):	96.898%	Volume Distribution (VD):	-0.22
Fu:	2.571% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.951
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.831
CYP2C19-inhibitor:	0.092	CYP2C19-substrate:	0.19
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.997	CYP2D6-substrate:	0.588
CYP3A4-inhibitor:	0.314	CYP3A4-substrate:	0.664
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	1.0
HLM stability:	0.994 ? 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):

6.902

Half-life (T1/2):

1.127

ADMET: Toxicity

hERG Blockers:	0.15	hERG Blockers (10um):	0.132
Human Hepatotoxicity (H-HT):	0.705	Drug-induced Liver Injury (DILI):	0.917
AMES Toxicity:	0.488	Rat Oral Acute Toxicity:	0.316
Maximum Recommended Daily Dose:	0.625	Skin Sensitization:	0.861
Carcinogencity:	0.476	Eye Corrosion:	0.0
Eye Irritation:	0.378	Respiratory Toxicity:	0.475
Drug-induced Neurotoxicity:	0.441	Ototoxicity:	0.649
Hematotoxicity:	0.198	Drug-induced Nephrotoxicity:	0.716
Genotoxicity:	0.472	RPMI-8226 Immunitoxicity:	0.213
A549 Cytotoxicity:	0.097	Hek293 Cytotoxicity:	0.437
BCF:	1.717 ? 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:	4.642 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.289 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.731 ? 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
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	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 NPC218140 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	10532
0.1-0.2	35255
0.2-0.3	3785
0.3-0.4	245
0.4-0.5	28
0.5-0.6	6
0.6-0.7	8
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
0.6761	Remote Similarity	NPC269843
0.6292	Remote Similarity	NPC478448
0.6222	Remote Similarity	NPC478449
0.6143	Remote Similarity	NPC109083
0.6111	Remote Similarity	NPC478444
0.6044	Remote Similarity	NPC478453
0.6044	Remote Similarity	NPC478450
0.6027	Remote Similarity	NPC189844
0.5914	Remote Similarity	NPC478451
0.5806	Remote Similarity	NPC478452
0.5714	Remote Similarity	NPC478447
0.5352	Remote Similarity	NPC280001
0.5269	Remote Similarity	NPC478443
0.5065	Remote Similarity	NPC158949

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC218140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3854
0.1-0.2	5161
0.2-0.3	132
0.3-0.4	2
0.4-0.5	1
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