NPASS Compound

Natural Product: NPC476856

Natural Product ID	NPC476856
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	methyl (3S)-3-acetyloxy-3-[(1R,2R,5R,6R,7R,8S,10S,11S,14S)-11-(furan-3-yl)-8-hydroxy-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.01,14.02,7]pentadecan-6-yl]propanoate
IUPAC Name	methyl (3S)-3-acetyloxy-3-[(1R,2R,5R,6R,7R,8S,10S,11S,14S)-11-(furan-3-yl)-8-hydroxy-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.01,14.02,7]pentadecan-6-yl]propanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	86302656
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

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 78 82 0 0 0 0 0 0 0 0999 V2000 -4.3519 -0.5209 -3.6453 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0676 -0.1381 -3.0045 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0660 0.0403 -3.7176 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0098 0.0140 -1.6169 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8426 0.3707 -0.9484 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2096 1.8672 -0.7784 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5469 2.0692 -0.1519 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4521 1.2395 -0.0169 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8737 3.3473 0.3682 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1289 3.5877 0.9713 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2868 -0.2780 0.2113 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0010 -1.7481 0.2240 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4014 -2.1120 1.5680 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5500 -1.1934 2.1493 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2474 -1.5836 3.0645 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7466 0.2239 1.7057 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1456 0.2922 0.3694 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6464 1.4479 -0.3447 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1262 1.1470 -0.7944 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8741 0.3880 0.2906 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2271 0.4951 1.6197 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9977 0.4911 2.8040 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6612 1.7462 2.3035 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4392 0.1798 2.6347 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0837 -0.4557 3.4869 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0232 0.6447 1.4597 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2336 1.0384 0.3423 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0939 0.7642 -0.8459 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0265 -0.2382 -1.0127 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5447 -0.1185 -2.1977 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0315 0.8903 -2.8412 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0940 1.4928 -2.0174 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0858 -1.0682 -0.0623 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9507 2.5555 0.5094 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1894 1.0960 2.7894 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8225 -2.8533 -0.1834 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2577 -2.9730 -1.6221 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0537 -3.1797 0.6465 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0276 -4.0077 0.0078 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1443 -0.0275 1.3966 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0461 0.3500 -3.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2732 -0.6269 -4.7277 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7918 -1.3842 -3.1307 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0510 0.3494 -1.7840 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5509 2.4536 -0.1834 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2697 2.2742 -1.8008 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0557 3.4045 2.0625 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3929 4.6653 0.8338 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9218 2.9276 0.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1011 -1.8436 -0.4933 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1893 -3.0653 1.3593 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1598 -2.4968 2.2987 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7268 -0.5428 -0.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2498 1.7527 -1.3070 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0639 0.4664 -1.6661 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5760 2.0944 -1.0721 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5712 0.2180 3.7653 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1044 2.1737 0.4346 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3024 -1.0185 -0.2746 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3013 1.1885 -3.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5006 2.3831 -2.2941 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5314 -1.7374 0.6682 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1208 -1.4228 0.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7928 -1.2961 -1.1150 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7914 3.3550 -0.0453 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0483 1.6385 3.3097 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2033 0.5202 3.6767 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4332 1.9302 2.4782 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5579 -2.4777 -2.3227 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2410 -4.0487 -1.9878 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3258 -2.7096 -1.7630 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3450 -4.2572 0.4248 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9498 -2.6222 0.3027 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8913 -3.1625 1.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4861 -4.1993 -0.8003 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7785 -0.5627 2.3210 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4209 0.9778 1.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0982 -0.5814 1.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 5 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 2 0 20 33 1 6 18 34 1 0 16 35 1 1 12 36 1 0 36 37 1 0 36 38 1 0 36 39 1 0 11 40 1 1 17 11 1 0 21 16 1 0 27 20 1 0 21 23 1 6 32 28 1 0 1 41 1 0 1 42 1 0 1 43 1 0 5 44 1 6 6 45 1 0 6 46 1 0 10 47 1 0 10 48 1 0 10 49 1 0 12 50 1 6 13 51 1 0 13 52 1 0 17 53 1 6 18 54 1 6 19 55 1 0 19 56 1 0 22 57 1 1 27 58 1 1 29 59 1 0 31 60 1 0 32 61 1 0 33 62 1 0 33 63 1 0 33 64 1 0 34 65 1 0 35 66 1 0 35 67 1 0 35 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 38 72 1 0 38 73 1 0 38 74 1 0 39 75 1 0 40 76 1 0 40 77 1 0 40 78 1 0 M END

Standard InCHIKey	IEUIPXVPQYMCJQ-IJMSCJJWSA-N
Standard InCHI	InChI=1S/C29H38O11/c1-14(30)38-19(11-20(33)36-7)27(5)17(25(2,3)35)10-18(32)28(6)21(27)16(31)12-26(4)22(15-8-9-37-13-15)39-24(34)23-29(26,28)40-23/h8-9,13,16-17,19,21-23,31,35H,10-12H2,1-7H3/t16-,17-,19-,21+,22-,23+,26-,27+,28+,29+/m0/s1
SMILES	CC(=O)O[C@@H](CC(=O)OC)[C@]1([C@@H](CC(=O)[C@@]2([C@@H]1[C@H](C[C@@]3([C@]24[C@H](O4)C(=O)O[C@H]3C5=COC=C5)C)O)C)C(C)(C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	562.24	Volume:	548.231 ? Van der Waals volume.
Dense:	1.026	LogP:	1.304 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.64 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.328 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	27.0
TPSA:	162.1 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.297	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.937	Fsp³:	0.724
MCE-18:	182.04 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.389	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.018 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.044	Promiscuous compounds:	0.561

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.147	MDCK Permeability:	-4.749
Pgp-inhibitor:	0.281	Pgp-substrate:	0.055
PAMPA:	0.978 ? 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):	0.007
20% Bioavailability (F20%):	0.018	30% Bioavailability (F30%):	0.122
50% Bioavailability (F50%):	0.861

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.893
Plasma Protein Binding (PPB):	65.089%	Volume Distribution (VD):	-0.38
Fu:	31.474% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.978
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.425
BSEP inhibitor:	0.941

ADMET: Metabolism

CYP1A2-inhibitor:	0.118	CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.651	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.631	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.246
CYP3A4-inhibitor:	0.905	CYP3A4-substrate:	0.206
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.79
HLM stability:	0.536 ? 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):

5.879

Half-life (T1/2):

1.331

ADMET: Toxicity

hERG Blockers:	0.041	hERG Blockers (10um):	0.286
Human Hepatotoxicity (H-HT):	0.51	Drug-induced Liver Injury (DILI):	0.531
AMES Toxicity:	0.581	Rat Oral Acute Toxicity:	0.823
Maximum Recommended Daily Dose:	0.892	Skin Sensitization:	0.835
Carcinogencity:	0.613	Eye Corrosion:	0.0
Eye Irritation:	0.359	Respiratory Toxicity:	0.893
Drug-induced Neurotoxicity:	0.196	Ototoxicity:	0.605
Hematotoxicity:	0.525	Drug-induced Nephrotoxicity:	0.842
Genotoxicity:	0.967	RPMI-8226 Immunitoxicity:	0.267
A549 Cytotoxicity:	0.003	Hek293 Cytotoxicity:	0.035
BCF:	0.392 ? 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:	3.153 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.151 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.431 ? 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
NPO33678	Clausena emarginata	Species	Rutaceae	Eukaryota	stems	Xishuangbanna, Yunnan Province, China	2010-AUG	PMID[24593150]

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
IC50	6

Activity Type	# Activity
Cell line	4
Others	2

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
NPT393	Cell line	HCT-116	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT1820	Cell line	NCI-H1650	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT2	Others	Unspecified	n.a.	IC50	=	8800	nM	PMID[24593150]
NPT2	Others	Unspecified	n.a.	IC50	>	10000	nM	PMID[24593150]

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 NPC476856 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	10490
0.1-0.2	37382
0.2-0.3	1754
0.3-0.4	165
0.4-0.5	46
0.5-0.6	12
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9067	High Similarity	NPC476858
0.775	Intermediate Similarity	NPC476853
0.7722	Intermediate Similarity	NPC476861
0.7722	Intermediate Similarity	NPC476850
0.7375	Intermediate Similarity	NPC476857
0.6353	Remote Similarity	NPC609366
0.6092	Remote Similarity	NPC472653
0.6092	Remote Similarity	NPC237155
0.5909	Remote Similarity	NPC23387
0.5824	Remote Similarity	NPC25255
0.5632	Remote Similarity	NPC470939
0.5556	Remote Similarity	NPC96443
0.5556	Remote Similarity	NPC290400
0.5556	Remote Similarity	NPC476860
0.5385	Remote Similarity	NPC305016
0.5269	Remote Similarity	NPC193798
0.5172	Remote Similarity	NPC604270
0.5109	Remote Similarity	NPC611370
0.5055	Remote Similarity	NPC51568
0.5055	Remote Similarity	NPC234660

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476856 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3648
0.1-0.2	5458
0.2-0.3	44
0.3-0.4	0
0.4-0.5	0
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