NPASS Compound

Natural Product: NPC87500

Natural Product ID	NPC87500
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ISVJQJMGKFYXBW-OQZZIDIHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11972334
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides

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 83 87 0 0 0 0 0 0 0 0999 V2000 -7.1666 -1.4889 -0.4791 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5615 -0.0724 -0.1623 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6880 0.1984 1.3111 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2697 1.6507 1.5147 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8068 1.8498 1.1794 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5037 0.8935 0.0390 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3622 1.2236 -0.6454 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3315 0.3092 -0.5207 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1050 0.7410 -1.3217 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5193 0.6941 -2.7849 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0784 -0.6294 -3.4219 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5744 -0.7259 -3.3811 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0915 -0.1760 -2.0346 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9755 -0.8560 -1.5361 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2369 -0.5799 -1.1342 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0578 -1.6402 -0.6953 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3425 -1.4618 -0.2759 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1472 -2.5006 0.1539 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6970 -3.6735 0.1689 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4391 -2.2149 0.5597 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9507 -0.9205 0.5487 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2964 -0.5764 0.9645 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1634 -1.5315 1.4198 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4661 -1.1901 1.8160 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8852 0.1090 1.7507 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0022 1.0871 1.2865 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7071 0.7294 0.8954 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1616 0.4614 2.1344 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0401 -0.5406 2.5988 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1196 0.0063 0.1263 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8903 -0.1905 -0.2706 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0910 0.8470 -0.6974 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7978 0.6696 -1.1191 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1120 1.8304 -1.5166 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5115 2.6078 -0.4769 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6783 2.1218 -0.6793 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1333 -0.2422 -1.0962 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0356 0.0930 -4.3662 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6684 -1.7229 -2.8144 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8674 1.7027 -3.4543 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6242 0.7769 -0.7448 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0501 1.4542 2.2861 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5985 2.0963 2.7913 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0262 0.1213 1.7644 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4683 -0.6479 2.7991 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6731 -1.3555 3.4253 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9063 -0.6283 3.1661 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0708 -1.6603 -0.4902 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5101 -1.7885 -1.5109 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5717 -2.2216 0.2796 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5901 0.1135 -0.5867 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0075 -0.4378 1.8878 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8431 2.2363 0.7390 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6594 2.8949 0.9193 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3220 -0.0842 0.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6978 -0.6203 -1.0286 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0885 0.0106 0.5024 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7015 1.7011 -1.0074 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6265 0.7311 -2.9065 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3511 -0.5375 -4.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3003 -1.7854 -3.5082 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1158 0.8969 -2.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6170 -2.6489 -0.7006 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0825 -3.0161 0.8974 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9272 -2.5757 1.5084 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1378 -1.9508 2.1754 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3481 2.1094 1.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0756 1.5349 0.5467 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6233 -0.9137 3.5475 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0790 -0.1503 2.7123 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0453 -1.3644 1.8503 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7412 3.2334 -0.9750 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2489 3.3072 -0.0605 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0053 1.9773 0.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1216 2.3828 -1.5703 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1669 -0.2574 -5.2770 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0195 -2.3935 -2.4828 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4056 2.5468 -3.5386 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9992 0.4815 2.3505 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1011 1.5644 3.4565 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2066 -1.7094 3.2956 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0442 -0.1673 4.1784 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5443 -0.1478 2.4073 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 1 0 8 9 1 0 9 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 2 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 25 28 1 0 28 29 1 0 21 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 32 36 1 0 13 37 1 0 12 38 1 0 11 39 1 0 10 40 1 0 6 41 1 0 5 42 1 0 4 43 1 0 3 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 41 2 1 0 37 9 1 0 33 15 1 0 31 17 2 0 27 22 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 6 3 52 1 1 4 53 1 6 5 54 1 6 6 55 1 1 8 56 1 0 8 57 1 0 9 58 1 1 10 59 1 1 11 60 1 6 12 61 1 6 13 62 1 6 16 63 1 0 20 64 1 0 23 65 1 0 24 66 1 0 26 67 1 0 27 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 35 72 1 0 35 73 1 0 35 74 1 0 36 75 1 0 38 76 1 0 39 77 1 0 40 78 1 0 42 79 1 0 43 80 1 0 47 81 1 0 47 82 1 0 47 83 1 0 M END

Standard InCHIKey	ISVJQJMGKFYXBW-OQZZIDIHSA-N
Standard InCHI	InChI=1S/C31H36O16/c1-12-27(44-13(2)32)23(36)25(38)30(43-12)42-11-20-21(34)22(35)24(37)31(47-20)46-19-9-16-17(33)10-18(14-5-7-15(40-3)8-6-14)45-28(16)26(39)29(19)41-4/h5-10,12,20-25,27,30-31,34-39H,11H2,1-4H3/t12-,20+,21+,22-,23-,24+,25+,27-,30+,31+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3cc4c(=O)cc(c5ccc(cc5)OC)oc4c(c3OC)O)O2)O)O)O)O1)O)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	664.2	Volume:	618.865 ? Van der Waals volume.
Dense:	1.073	LogP:	1.041 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.471 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.846 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	31.0
TPSA:	233.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.162	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.794	Fsp³:	0.484
MCE-18:	120.217 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.652	Fluc inhibitor:	0.282 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.834 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.577 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.048	Promiscuous compounds:	0.206

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.062	MDCK Permeability:	-5.331
Pgp-inhibitor:	0.027	Pgp-substrate:	0.32
PAMPA:	0.96 ? 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):	0.901
20% Bioavailability (F20%):	0.305	30% Bioavailability (F30%):	0.95
50% Bioavailability (F50%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.642
Plasma Protein Binding (PPB):	80.948%	Volume Distribution (VD):	-0.261
Fu:	17.57% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.151
BSEP inhibitor:	0.049

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.551
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.651 ? 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):

1.941

Half-life (T1/2):

4.012

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.099
Human Hepatotoxicity (H-HT):	0.374	Drug-induced Liver Injury (DILI):	0.972
AMES Toxicity:	0.861	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.032	Skin Sensitization:	0.84
Carcinogencity:	0.111	Eye Corrosion:	0.0
Eye Irritation:	0.025	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.949
Hematotoxicity:	0.297	Drug-induced Nephrotoxicity:	0.547
Genotoxicity:	0.595	RPMI-8226 Immunitoxicity:	0.169
A549 Cytotoxicity:	0.109	Hek293 Cytotoxicity:	0.258
BCF:	0.419 ? 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:	3.258 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.875 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.028 ? 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
NPO20134	Dicliptera riparia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20134	Dicliptera riparia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20134	Dicliptera riparia	Species	Acanthaceae	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 NPC87500 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	14538
0.1-0.2	31328
0.2-0.3	3252
0.3-0.4	592
0.4-0.5	121
0.5-0.6	20
0.6-0.7	2
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
0.7234	Intermediate Similarity	NPC488089
0.6289	Remote Similarity	NPC204693
0.6105	Remote Similarity	NPC211594
0.5941	Remote Similarity	NPC483707
0.5926	Remote Similarity	NPC488087
0.5859	Remote Similarity	NPC22062
0.5859	Remote Similarity	NPC473634
0.5859	Remote Similarity	NPC138811
0.578	Remote Similarity	NPC488083
0.5769	Remote Similarity	NPC470449
0.5714	Remote Similarity	NPC470446
0.5631	Remote Similarity	NPC473623
0.55	Remote Similarity	NPC295613
0.55	Remote Similarity	NPC473657
0.5446	Remote Similarity	NPC488088
0.53	Remote Similarity	NPC172807
0.5288	Remote Similarity	NPC475366
0.5189	Remote Similarity	NPC209296
0.5098	Remote Similarity	NPC254540
0.5096	Remote Similarity	NPC473512
0.5096	Remote Similarity	NPC129827
0.5046	Remote Similarity	NPC101636
0.5046	Remote Similarity	NPC298171

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC87500 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4622
0.1-0.2	4460
0.2-0.3	59
0.3-0.4	4
0.4-0.5	3
0.5-0.6	2
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
0.5189	Remote Similarity	NPD7054	Phase 4
0.5045	Remote Similarity	NPD7472	Pre-clinical

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