NPASS Compound

Natural Product: NPC481018

Natural Product ID	NPC481018
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SSGLNIQQJMACGD-FNXRTXNCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	127042991
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

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 74 76 0 0 0 0 0 0 0 0999 V2000 -4.8020 -1.3507 1.0929 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0300 -0.3508 1.8960 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5058 0.9729 1.7220 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8200 1.9167 2.5836 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6280 1.3049 0.5778 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2541 0.7593 0.7100 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2356 0.9731 -0.3344 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1373 2.5323 -0.4180 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3377 0.5047 -1.6999 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7335 0.3275 -2.2949 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5629 -0.6827 -2.1705 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7657 -0.9335 -1.5593 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5798 -0.8144 -0.0563 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9010 -0.9491 0.6890 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7860 -0.0224 0.5772 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5776 1.1823 -0.2453 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1432 1.4891 -0.5023 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1549 0.5468 0.2182 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1031 2.2616 0.5690 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1073 3.0796 0.1135 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5564 2.8530 -1.0474 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6195 4.1714 0.9714 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7217 4.9056 0.2073 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7773 -2.2417 1.4696 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5366 -2.2466 2.6028 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3319 -3.4084 2.5878 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3860 -2.1627 1.7485 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0378 -2.0381 0.3904 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3050 -2.4442 0.1760 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7024 -3.6566 -0.3900 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8174 -4.4536 -0.7350 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1607 -3.9269 -0.5485 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0843 -2.2900 -1.8050 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2833 -2.4336 -2.4695 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1901 -1.2361 0.2259 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2097 -2.3522 1.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6846 -0.5971 2.7624 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4224 2.9356 2.4581 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4709 1.6668 3.4069 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5658 2.4412 0.6069 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1437 1.1420 -0.3876 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3518 -0.2638 1.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8404 1.4156 1.5980 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1869 2.8464 -0.7249 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5618 2.7810 -1.3280 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8260 2.9789 0.5083 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9375 1.3497 -2.3845 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3140 -0.4727 -1.8554 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2395 1.2805 -2.5035 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5172 -0.0598 -3.3533 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3378 -0.5126 -3.2764 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2044 -1.6065 -2.2407 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5826 -0.3669 -1.9773 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7270 -0.1292 1.1092 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1252 1.1817 -1.2153 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9900 2.5344 -0.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9322 1.4996 -1.6131 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2297 0.8125 1.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8526 4.9408 1.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9881 3.8030 1.9483 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0480 5.8185 0.7255 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2597 5.2404 -0.7546 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5533 4.1942 0.0335 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9463 -3.1031 0.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9722 -3.4508 3.5036 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6816 -4.3248 2.6465 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9262 -3.3832 1.6548 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6036 -2.8864 -0.0670 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3393 -4.9255 -0.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5824 -3.9235 0.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6818 -3.1392 -1.1278 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2817 -1.9246 -3.4607 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1332 -2.0686 -1.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4294 -3.5108 -2.6663 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 7 6 1 1 7 8 1 0 7 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 14 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 12 33 1 0 33 34 1 0 18 7 1 0 18 13 1 0 28 13 1 0 1 35 1 0 1 36 1 0 2 37 1 0 4 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 8 44 1 0 8 45 1 0 8 46 1 0 9 47 1 6 10 48 1 0 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 12 53 1 6 15 54 1 0 16 55 1 6 17 56 1 0 17 57 1 0 18 58 1 1 22 59 1 0 22 60 1 0 23 61 1 0 23 62 1 0 23 63 1 0 24 64 1 6 26 65 1 0 26 66 1 0 26 67 1 0 28 68 1 6 32 69 1 0 32 70 1 0 32 71 1 0 34 72 1 0 34 73 1 0 34 74 1 0 M END

Standard InCHIKey	SSGLNIQQJMACGD-FNXRTXNCSA-N
Standard InCHI	InChI=1S/C27H40O7/c1-9-16(3)11-12-26(6)17(4)13-22(30-7)27-20(24(31-8)34-25(27)32-18(5)28)14-19(15-21(26)27)33-23(29)10-2/h9,14,17,19,21-22,24-25H,1,3,10-13,15H2,2,4-8H3/t17-,19+,21+,22+,24+,25-,26-,27-/m1/s1
SMILES	C=CC(=C)CC[C@]1(C)[C@H](C)C[C@@H]([C@@]23C(=C[C@@H](C[C@@H]12)OC(=O)CC)[C@@H](OC)O[C@H]3OC(=O)C)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	476.28	Volume:	498.228 ? Van der Waals volume.
Dense:	0.956	LogP:	3.477 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.156 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.994 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	19.0
TPSA:	80.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.271	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.798	Fsp³:	0.704
MCE-18:	85.87 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.455	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.38	Promiscuous compounds:	0.7

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.107	MDCK Permeability:	-4.812
Pgp-inhibitor:	0.98	Pgp-substrate:	0.622
PAMPA:	0.055 ? 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):	0.003
20% Bioavailability (F20%):	0.978	30% Bioavailability (F30%):	0.971
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.288	MRP1:	0.985
Plasma Protein Binding (PPB):	71.074%	Volume Distribution (VD):	-0.157
Fu:	28.094% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.969
OATP1B3 inhibitor:	0.622	BCRP inhibitor:	0.816
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.125	CYP1A2-substrate:	0.231
CYP2C19-inhibitor:	0.957	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.544
CYP3A4-inhibitor:	0.071	CYP3A4-substrate:	0.987
CYP2B6-substrate:	0.027	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

10.659

Half-life (T1/2):

1.113

ADMET: Toxicity

hERG Blockers:	0.121	hERG Blockers (10um):	0.523
Human Hepatotoxicity (H-HT):	0.428	Drug-induced Liver Injury (DILI):	0.45
AMES Toxicity:	0.868	Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.975	Skin Sensitization:	0.953
Carcinogencity:	0.66	Eye Corrosion:	0.002
Eye Irritation:	0.19	Respiratory Toxicity:	0.952
Drug-induced Neurotoxicity:	0.809	Ototoxicity:	0.538
Hematotoxicity:	0.496	Drug-induced Nephrotoxicity:	0.615
Genotoxicity:	0.91	RPMI-8226 Immunitoxicity:	0.243
A549 Cytotoxicity:	0.267	Hek293 Cytotoxicity:	0.34
BCF:	0.783 ? 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:	3.719 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.552 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.903 ? 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
NPO40063	Casearia graveolens	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26474353]
NPO40063	Casearia graveolens	Species	Salicaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31916761]

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
EC50	1

Activity Type	# Activity
Cell line	1

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
NPT681	Cell line	PC-12	Rattus norvegicus	EC50	=	4400.0	nM	PMID[26474353]

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 NPC481018 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	22337
0.1-0.2	25035
0.2-0.3	2338
0.3-0.4	38
0.4-0.5	53
0.5-0.6	26
0.6-0.7	13
0.7-0.8	0
0.8-0.85	5
0.85-0.9	7
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9434	High Similarity	NPC472189
0.9091	High Similarity	NPC481020
0.8909	High Similarity	NPC171598
0.8793	High Similarity	NPC481017
0.8772	High Similarity	NPC472188
0.8596	High Similarity	NPC471362
0.8596	High Similarity	NPC471372
0.8596	High Similarity	NPC318917
0.8596	High Similarity	NPC481019
0.8448	Intermediate Similarity	NPC472186
0.8305	Intermediate Similarity	NPC471366
0.8305	Intermediate Similarity	NPC476800
0.8305	Intermediate Similarity	NPC488649
0.8305	Intermediate Similarity	NPC488237
0.7778	Intermediate Similarity	NPC472187
0.7541	Intermediate Similarity	NPC488236
0.7213	Intermediate Similarity	NPC600724
0.7188	Intermediate Similarity	NPC473545
0.6935	Remote Similarity	NPC488651
0.6935	Remote Similarity	NPC488648
0.6774	Remote Similarity	NPC606965
0.6667	Remote Similarity	NPC132395
0.6667	Remote Similarity	NPC471364
0.6406	Remote Similarity	NPC479934
0.6364	Remote Similarity	NPC473204
0.6269	Remote Similarity	NPC471365
0.6212	Remote Similarity	NPC479943
0.619	Remote Similarity	NPC603601
0.6087	Remote Similarity	NPC48548
0.6032	Remote Similarity	NPC488650
0.6032	Remote Similarity	NPC481022
0.5942	Remote Similarity	NPC238397
0.5821	Remote Similarity	NPC479935
0.5821	Remote Similarity	NPC479936
0.5821	Remote Similarity	NPC488235
0.5797	Remote Similarity	NPC479940
0.5797	Remote Similarity	NPC7644
0.575	Remote Similarity	NPC488962
0.5634	Remote Similarity	NPC488963
0.5588	Remote Similarity	NPC479939
0.5556	Remote Similarity	NPC488219
0.5507	Remote Similarity	NPC479937
0.5493	Remote Similarity	NPC475889
0.5493	Remote Similarity	NPC7613
0.5493	Remote Similarity	NPC479942
0.5479	Remote Similarity	NPC488221
0.5479	Remote Similarity	NPC488220
0.5479	Remote Similarity	NPC488216
0.5429	Remote Similarity	NPC479938
0.5417	Remote Similarity	NPC479941
0.5342	Remote Similarity	NPC471363
0.5278	Remote Similarity	NPC217921
0.5278	Remote Similarity	NPC88013
0.5278	Remote Similarity	NPC135015
0.52	Remote Similarity	NPC127933
0.5195	Remote Similarity	NPC486752
0.5139	Remote Similarity	NPC128795

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC481018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7197
0.1-0.2	1934
0.2-0.3	19
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