NPASS Compound

Natural Product: NPC587557

Natural Product ID	NPC587557
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(10~{R},13~{R},17~{R})-17-[(1~{R})-4-hydroperoxy-4-isopropyl-1-methyl-hex-5-enyl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
IUPAC Name	(10~{R},13~{R},17~{R})-17-[(1~{R})-4-hydroperoxy-4-isopropyl-1-methyl-hex-5-enyl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-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 78 81 0 0 0 0 0 0 0 0999 V2000 -4.4838 -2.3019 0.1833 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8429 -1.2930 0.9683 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9372 0.0886 0.4381 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8546 0.9794 0.9304 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4498 0.5753 0.6249 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0886 0.5042 -0.8316 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2751 1.8453 -1.4618 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8558 -0.2264 -1.0576 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5074 -0.3101 -2.5774 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8114 -1.0557 -2.5703 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3130 -0.9309 -1.2020 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7536 -0.5792 -1.0502 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6519 -1.5073 -1.8436 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0941 -1.3167 -1.5613 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4083 -0.7777 -0.2370 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6891 -0.7736 0.1372 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1400 -0.2671 1.4259 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3164 0.1207 1.6448 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1733 -0.2000 2.5451 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8264 -0.7434 2.1032 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4385 -0.2314 0.7363 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4843 1.2576 0.7335 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0764 -0.7960 0.4059 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0212 -0.4154 1.3646 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7347 0.1063 0.8946 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4653 0.1840 -0.5713 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0001 1.4657 -1.1871 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1189 0.0533 -0.9288 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2286 -0.5955 -1.2086 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2534 0.6710 0.9901 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2636 0.6970 2.4707 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4945 2.0492 0.4194 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4112 -3.3135 0.5578 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2608 -2.0804 -0.8652 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0612 -1.5230 1.9989 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9893 2.0104 0.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9167 1.1145 2.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7126 1.1705 1.2168 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3631 -0.4898 1.0106 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9177 -0.1399 -1.2860 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 1.9921 -1.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8333 1.9291 -2.4687 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0172 2.7096 -0.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9758 -1.3241 -0.8038 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3003 -0.8119 -3.1288 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3551 0.6941 -2.9927 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4889 -0.7178 -3.3741 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5613 -2.1366 -2.7804 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1030 -1.8392 -0.6002 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0477 0.4326 -1.3174 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3491 -2.5440 -1.5890 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3884 -1.3698 -2.9261 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4985 -0.5852 -2.3211 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6733 -2.2615 -1.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4258 -1.1649 -0.5497 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1018 0.8488 2.8881 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5326 -0.8520 3.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9318 -1.8501 2.0532 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1138 -0.5209 2.8978 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5601 1.5463 0.8982 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2145 1.7076 -0.2371 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9356 1.7125 1.5790 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2228 -1.9181 0.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8241 -1.2602 2.1070 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4861 0.3635 2.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6259 1.1707 1.2741 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0715 -0.5192 1.3813 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8386 1.8438 -0.5381 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4465 1.3102 -2.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2296 2.2451 -1.3304 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.1484 -2.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0438 -0.0439 0.6351 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2585 1.7572 2.8497 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4216 0.1813 2.9550 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2222 0.2681 2.8847 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3371 2.8448 1.1777 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5365 2.0772 0.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8094 2.2080 -0.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 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 2 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 3 28 1 0 28 29 1 0 3 30 1 0 30 31 1 0 30 32 1 0 26 8 1 0 26 11 1 0 23 12 1 0 21 15 1 0 1 33 1 0 1 34 1 0 2 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 5 39 1 0 6 40 1 6 7 41 1 0 7 42 1 0 7 43 1 0 8 44 1 1 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 16 55 1 0 19 56 1 0 19 57 1 0 20 58 1 0 20 59 1 0 22 60 1 0 22 61 1 0 22 62 1 0 23 63 1 0 24 64 1 0 24 65 1 0 25 66 1 0 25 67 1 0 27 68 1 0 27 69 1 0 27 70 1 0 29 71 1 0 30 72 1 0 31 73 1 0 31 74 1 0 31 75 1 0 32 76 1 0 32 77 1 0 32 78 1 0 M END

Standard InCHIKey	SICXMLBXUWOBEI-SJTOJMNLSA-N
Standard InCHI	InChI=1S/C29H46O3/c1-7-29(32-31,19(2)3)17-12-20(4)24-10-11-25-23-9-8-21-18-22(30)13-15-27(21,5)26(23)14-16-28(24,25)6/h7,18-20,23-26,31H,1,8-17H2,2-6H3/t20-,23?,24-,25?,26?,27+,28-,29?/m1/s1
SMILES	C=CC(CC[C@@H](C)[C@H]1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@@]21C)(OO)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.34	Volume:	494.375 ? Van der Waals volume.
Dense:	0.895	LogP:	5.959 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.511 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.837 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	22.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.25	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.732	Fsp³:	0.828
MCE-18:	73.321 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.797	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.402	Promiscuous compounds:	0.105

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.057	MDCK Permeability:	-5.018
Pgp-inhibitor:	0.854	Pgp-substrate:	0.001
PAMPA:	0.001 ? 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):	0.0
20% Bioavailability (F20%):	0.188	30% Bioavailability (F30%):	0.805
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.529	MRP1:	0.754
Plasma Protein Binding (PPB):	97.855%	Volume Distribution (VD):	-0.036
Fu:	1.7% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.967	BCRP inhibitor:	0.067
BSEP inhibitor:	0.97

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.799
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	0.974	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.115	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.933
CYP2B6-substrate:	0.998	CYP2C8-inhibitor:	0.998
HLM stability:	0.992 ? 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):

13.695

Half-life (T1/2):

0.469

ADMET: Toxicity

hERG Blockers:	0.283	hERG Blockers (10um):	0.609
Human Hepatotoxicity (H-HT):	0.787	Drug-induced Liver Injury (DILI):	0.695
AMES Toxicity:	0.61	Rat Oral Acute Toxicity:	0.367
Maximum Recommended Daily Dose:	0.681	Skin Sensitization:	0.972
Carcinogencity:	0.821	Eye Corrosion:	0.082
Eye Irritation:	0.259	Respiratory Toxicity:	0.545
Drug-induced Neurotoxicity:	0.659	Ototoxicity:	0.515
Hematotoxicity:	0.319	Drug-induced Nephrotoxicity:	0.191
Genotoxicity:	0.729	RPMI-8226 Immunitoxicity:	0.098
A549 Cytotoxicity:	0.1	Hek293 Cytotoxicity:	0.675
BCF:	2.337 ? 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:	5.006 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.273 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.87 ? 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
NPO16318	Turbinaria conoides	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075746]
NPO16318	Turbinaria conoides	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16318	Turbinaria conoides	Species	Sargassaceae	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 NPC587557 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	20392
0.1-0.2	26499
0.2-0.3	2745
0.3-0.4	163
0.4-0.5	27
0.5-0.6	14
0.6-0.7	9
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
0.7414	Intermediate Similarity	NPC489872
0.7222	Intermediate Similarity	NPC282593
0.7091	Intermediate Similarity	NPC35734
0.7091	Intermediate Similarity	NPC159577
0.7091	Intermediate Similarity	NPC602429
0.7049	Intermediate Similarity	NPC489873
0.6964	Remote Similarity	NPC149203
0.6364	Remote Similarity	NPC307176
0.6364	Remote Similarity	NPC321874
0.6316	Remote Similarity	NPC214043
0.6316	Remote Similarity	NPC85774
0.629	Remote Similarity	NPC320514
0.6207	Remote Similarity	NPC115023
0.6102	Remote Similarity	NPC237712
0.6	Remote Similarity	NPC249312
0.5692	Remote Similarity	NPC488870
0.5556	Remote Similarity	NPC469948
0.5484	Remote Similarity	NPC303613
0.5385	Remote Similarity	NPC309603
0.5345	Remote Similarity	NPC139397
0.5246	Remote Similarity	NPC227064
0.5246	Remote Similarity	NPC329043
0.5246	Remote Similarity	NPC58841
0.5246	Remote Similarity	NPC161423
0.5167	Remote Similarity	NPC2634
0.5167	Remote Similarity	NPC265782
0.5167	Remote Similarity	NPC251929
0.5161	Remote Similarity	NPC144258
0.5161	Remote Similarity	NPC327115

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC587557 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6802
0.1-0.2	2100
0.2-0.3	169
0.3-0.4	55
0.4-0.5	12
0.5-0.6	7
0.6-0.7	1
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
0.6364	Remote Similarity	NPD4747	Phase 4
0.5902	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6939	Phase 3
0.5556	Remote Similarity	NPD5737	Phase 4
0.5385	Remote Similarity	NPD6672	Phase 4
0.5246	Remote Similarity	NPD3666	Phase 4
0.5246	Remote Similarity	NPD4221	Phase 4
0.5167	Remote Similarity	NPD4691	Approved

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