NPASS Compound

Natural Product: NPC551670

Natural Product ID	NPC551670
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{R},3~{R})-2-[3-[5-[(3~{S},3~{a}~{R},6~{S},6~{a}~{R})-3-(4-hydroxy-3-methoxy-phenyl)-1,3,3~{a},4,6,6~{a}-hexahydrofuro[3,4-c]furan-6-yl]-2-hydroxy-3-methoxy-phenyl]-4,5-dihydroxy-phenyl]-3,5,7-trihydroxy-chroman-4-one
IUPAC Name	(2~{R},3~{R})-2-[3-[5-[(3~{S},3~{a}~{R},6~{S},6~{a}~{R})-3-(4-hydroxy-3-methoxy-phenyl)-1,3,3~{a},4,6,6~{a}-hexahydrofuro[3,4-c]furan-6-yl]-2-hydroxy-3-methoxy-phenyl]-4,5-dihydroxy-phenyl]-3,5,7-trihydroxy-chroman-4-one
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 80 86 0 0 0 0 0 0 0 0999 V2000 7.3249 2.0825 0.4024 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1125 1.0368 0.9204 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7695 -0.2991 0.8141 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6094 -0.6458 0.1770 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1827 -1.9409 0.0205 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9447 -2.3172 -0.6591 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3199 -3.2928 0.1546 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9232 -2.5522 1.2660 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4050 -1.2245 0.7365 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8908 -1.2594 -0.6961 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6802 -1.7934 -1.4280 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7899 -2.2467 -0.4562 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9281 -1.3400 0.6194 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2344 -0.1066 0.1854 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7514 1.1625 0.3487 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0787 2.2932 -0.0684 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6873 3.5186 0.1436 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9282 3.6906 0.7477 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1437 2.1172 -0.6621 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8350 3.2423 -1.0877 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7157 0.8772 -0.8548 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0117 0.6926 -1.4847 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1955 0.6712 -0.7817 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4181 0.4953 -1.3801 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6921 0.4684 -0.6530 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6196 -0.3371 0.5329 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8143 -0.4737 1.2424 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0555 -1.5706 2.0680 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2289 -1.7232 2.7768 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4401 -2.8280 3.5919 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2064 -0.7549 2.6682 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0079 0.3461 1.8623 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9958 1.3148 1.7587 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8205 0.4690 1.1652 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5716 1.6339 0.2923 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5160 2.4117 0.0067 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1747 1.8235 -0.2130 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1076 2.7484 -1.2237 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4151 0.3350 -2.7631 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2614 0.3483 -3.5139 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2484 0.1892 -4.8937 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0523 0.5300 -2.8550 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.5516 -3.5747 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0200 -0.2326 -0.4278 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9923 -2.9494 0.5485 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1695 -2.6231 1.1969 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5566 -1.3023 1.3290 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7352 -0.9304 1.9750 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9281 3.0181 0.4231 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9512 1.8979 -0.6111 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4385 2.2096 1.0838 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9911 0.1396 -0.2274 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1072 -2.8133 -1.6367 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7786 -2.3334 1.9192 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1480 -3.0716 1.8644 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7902 -0.3972 1.3245 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1984 -0.2942 -1.0878 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2618 -0.9670 -2.0419 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9615 -2.6024 -2.1207 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4257 -1.7936 1.4981 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7152 1.2538 0.8205 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9052 3.2663 1.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6980 3.1016 0.1681 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1798 4.7756 0.7191 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3016 3.2777 -1.9916 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1388 0.7998 0.2857 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4842 0.0401 -1.3040 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2684 -2.3123 2.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8870 -3.6866 3.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1446 -0.8664 3.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7029 1.2614 1.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5297 2.1411 0.6531 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0718 3.6714 -0.8318 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3711 0.1939 -3.2615 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8513 -0.6679 -5.2517 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0392 0.1490 -3.1296 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4550 -1.2121 -0.5718 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7347 -3.9946 0.4717 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8264 -3.3651 1.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6033 -1.1249 1.4903 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 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 2 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 2 0 19 20 1 0 19 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 29 31 2 0 31 32 1 0 32 33 1 0 32 34 2 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 1 0 24 39 2 0 39 40 1 0 40 41 1 0 40 42 2 0 42 43 1 0 21 44 2 0 5 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 47 3 1 0 10 6 1 0 44 14 1 0 13 9 1 0 42 22 1 0 37 25 1 0 34 27 1 0 1 49 1 0 1 50 1 0 1 51 1 0 4 52 1 0 6 53 1 6 8 54 1 0 8 55 1 0 9 56 1 1 10 57 1 6 11 58 1 0 11 59 1 0 13 60 1 1 15 61 1 0 18 62 1 0 18 63 1 0 18 64 1 0 20 65 1 0 23 66 1 0 25 67 1 6 28 68 1 0 30 69 1 0 31 70 1 0 33 71 1 0 37 72 1 1 38 73 1 0 39 74 1 0 41 75 1 0 43 76 1 0 44 77 1 0 45 78 1 0 46 79 1 0 48 80 1 0 M END

Standard InCHIKey	TXOKTGDAECRVPW-WEKAZSQWSA-N
Standard InCHI	InChI=1S/C35H32O13/c1-44-25-8-14(3-4-22(25)37)33-20-12-47-34(21(20)13-46-33)16-6-19(30(41)27(9-16)45-2)18-5-15(7-24(39)29(18)40)35-32(43)31(42)28-23(38)10-17(36)11-26(28)48-35/h3-11,20-21,32-41,43H,12-13H2,1-2H3/t20-,21-,32-,33+,34+,35+/m0/s1
SMILES	COC1=CC([C@H]2OC[C@H]3[C@@H]2CO[C@@H]3C2=CC(OC)=C(O)C(C3=CC([C@H]4OC5=CC(O)=CC(O)=C5C(=O)[C@@H]4O)=CC(O)=C3O)=C2)=CC=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	660.18	Volume:	634.02 ? Van der Waals volume.
Dense:	1.041	LogP:	1.318 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.546 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.674 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	39.0
TPSA:	204.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.144	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.825	Fsp³:	0.286
MCE-18:	144.289 ? 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:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.843	Fluc inhibitor:	0.324 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.421 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.639 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.27	Promiscuous compounds:	0.237

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.301	MDCK Permeability:	-5.415
Pgp-inhibitor:	0.057	Pgp-substrate:	0.051
PAMPA:	0.068 ? 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):	0.001
20% Bioavailability (F20%):	0.022	30% Bioavailability (F30%):	0.931
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.982
Plasma Protein Binding (PPB):	95.61%	Volume Distribution (VD):	-0.061
Fu:	4.14% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.959
BSEP inhibitor:	0.194

ADMET: Metabolism

CYP1A2-inhibitor:	0.848	CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.01	CYP2C19-substrate:	0.011
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.721	CYP2D6-substrate:	0.984
CYP3A4-inhibitor:	0.7	CYP3A4-substrate:	0.906
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.803 ? 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):

6.438

Half-life (T1/2):

3.263

ADMET: Toxicity

hERG Blockers:	0.1	hERG Blockers (10um):	0.461
Human Hepatotoxicity (H-HT):	0.973	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.84	Rat Oral Acute Toxicity:	0.764
Maximum Recommended Daily Dose:	0.934	Skin Sensitization:	0.993
Carcinogencity:	0.269	Eye Corrosion:	0.0
Eye Irritation:	0.569	Respiratory Toxicity:	0.615
Drug-induced Neurotoxicity:	0.136	Ototoxicity:	0.673
Hematotoxicity:	0.441	Drug-induced Nephrotoxicity:	0.948
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.576
A549 Cytotoxicity:	0.993	Hek293 Cytotoxicity:	0.946
BCF:	1.18 ? 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:	4.081 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.15 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.607 ? 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
NPO20918	Pseudotsuga menziesii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34216094]
NPO20918	Pseudotsuga menziesii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20918	Pseudotsuga menziesii	Species	Pinaceae	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 NPC551670 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	18391
0.1-0.2	27593
0.2-0.3	3388
0.3-0.4	390
0.4-0.5	75
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
0.6154	Remote Similarity	NPC326037
0.6154	Remote Similarity	NPC13858
0.5844	Remote Similarity	NPC36835
0.5844	Remote Similarity	NPC246162
0.5844	Remote Similarity	NPC9743
0.5844	Remote Similarity	NPC260491
0.5844	Remote Similarity	NPC61506
0.5844	Remote Similarity	NPC240476
0.5435	Remote Similarity	NPC138688
0.5435	Remote Similarity	NPC72787
0.5435	Remote Similarity	NPC217795
0.5435	Remote Similarity	NPC58223
0.5326	Remote Similarity	NPC36916
0.5326	Remote Similarity	NPC36
0.5326	Remote Similarity	NPC7154
0.5326	Remote Similarity	NPC125039
0.5326	Remote Similarity	NPC7688
0.5309	Remote Similarity	NPC320825
0.5275	Remote Similarity	NPC606364
0.5213	Remote Similarity	NPC279209
0.5213	Remote Similarity	NPC102277
0.5213	Remote Similarity	NPC479117

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC551670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4681
0.1-0.2	4426
0.2-0.3	35
0.3-0.4	3
0.4-0.5	2
0.5-0.6	3
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
0.5326	Remote Similarity	NPD6166	Phase 2
0.5326	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.5326	Remote Similarity	NPD6168	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