NPASS Compound

Natural Product: NPC481361

Natural Product ID	NPC481361
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YZTMIVVMHVEJFP-FBFNHCROSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44575932
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 -5.3316 2.5550 -1.2718 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7818 1.1873 -1.6075 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1697 0.9003 -3.0550 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4604 0.1398 -0.7546 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8469 0.2079 0.6062 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3992 -0.3230 0.5531 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7375 0.3156 1.7595 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3237 -0.1180 1.8278 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5564 0.2997 0.6293 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3065 1.8095 0.7753 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2734 0.1291 -0.6452 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5438 0.1144 -1.7535 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9227 0.2519 -1.8436 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5839 0.3153 -0.5139 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0480 -0.0505 -0.5513 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3573 -1.2593 -1.3503 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7442 1.1152 -1.2776 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2418 0.9778 -1.2041 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7662 0.8480 0.1772 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0173 -0.1215 1.0561 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6058 -1.5010 1.0226 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5526 -0.0323 0.8439 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8234 -1.0394 1.7349 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4103 -0.5348 1.8473 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7733 -0.4341 0.4840 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4348 -1.8457 0.0653 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2393 0.3531 2.3797 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0956 0.4009 0.1172 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7817 2.1351 -1.7674 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7560 -0.0238 -0.7475 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2903 1.2138 -1.4276 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5422 -1.7664 0.8320 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2042 -2.5982 -0.0223 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0496 -2.1786 2.0377 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2248 -3.5352 2.3983 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2164 3.1772 -2.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4172 2.5138 -1.0554 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7592 3.0334 -0.4388 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2700 1.8560 -3.6166 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4320 0.2169 -3.4956 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1699 0.4247 -3.0763 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5225 0.4231 -0.6734 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3603 -0.8631 -1.2158 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4658 -0.4000 1.2977 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8768 1.2384 0.9678 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3116 -0.0729 2.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9255 1.3991 1.7354 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2823 -1.1822 2.0923 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8659 0.4094 2.7190 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1843 2.2593 1.2782 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2467 2.3044 -0.2161 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5485 2.0262 1.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0449 -0.0114 -2.7353 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2709 -0.5857 -2.4826 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1130 1.2316 -2.3730 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5718 1.3953 -0.1933 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2622 -0.9820 -2.4427 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4419 -1.4782 -1.2381 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8123 -2.1622 -1.1052 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4645 2.0365 -0.7463 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4506 1.1450 -2.3317 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6206 0.1265 -1.8101 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7807 1.8557 0.6408 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2410 -1.7305 1.9303 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8940 -2.3215 0.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3664 -1.4984 0.1863 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2348 0.9702 1.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3393 -1.0576 2.7058 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9106 -2.0248 1.2873 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8097 -1.2706 2.4281 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4512 0.4468 2.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1107 -2.5946 0.5311 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4203 -2.0100 -1.0228 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5721 -2.1174 0.4393 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7308 1.1864 2.4661 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3233 0.0995 1.0300 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6574 1.9702 -2.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9630 -0.8758 -1.4388 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8489 1.2530 -2.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9321 2.0899 -0.8618 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5891 -3.5473 3.4461 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2196 -4.0149 2.4203 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9506 -4.0681 1.7832 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 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 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 20 27 1 1 19 28 1 0 18 29 1 0 11 30 1 0 30 31 1 0 6 32 1 1 32 33 2 0 32 34 1 0 34 35 1 0 31 2 1 0 30 6 1 0 25 9 1 0 25 14 1 0 22 15 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 10 50 1 0 10 51 1 0 10 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 14 56 1 1 16 57 1 0 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 18 62 1 6 19 63 1 1 21 64 1 0 21 65 1 0 21 66 1 0 22 67 1 1 23 68 1 0 23 69 1 0 24 70 1 0 24 71 1 0 26 72 1 0 26 73 1 0 26 74 1 0 27 75 1 0 28 76 1 0 29 77 1 0 30 78 1 6 31 79 1 0 31 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 M END

Standard InCHIKey	YZTMIVVMHVEJFP-FBFNHCROSA-N
Standard InCHI	InChI=1S/C30H48O5/c1-25(2)12-14-30(24(33)35-7)15-13-27(4)18(19(30)16-25)8-9-21-26(3)17-20(31)23(32)29(6,34)22(26)10-11-28(21,27)5/h8,19-23,31-32,34H,9-17H2,1-7H3/t19-,20+,21+,22+,23-,26+,27+,28+,29-,30-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@](C)([C@@H]5CC[C@@]34C)O)O)O)[C@@H]2C1)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	523.332 ? Van der Waals volume.
Dense:	0.933	LogP:	3.925 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.853 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.761 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	86.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.356	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.979	Fsp³:	0.9
MCE-18:	108.07 ? 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:	0.804	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.023 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.327	Promiscuous compounds:	0.238

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.149	MDCK Permeability:	-4.947
Pgp-inhibitor:	0.004	Pgp-substrate:	0.017
PAMPA:	0.998 ? 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%):	0.143	30% Bioavailability (F30%):	0.172
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977	MRP1:	0.221
Plasma Protein Binding (PPB):	91.704%	Volume Distribution (VD):	0.094
Fu:	9.969% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.774
BSEP inhibitor:	0.961

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.658
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.976 ? 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):

5.516

Half-life (T1/2):

0.985

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.135
Human Hepatotoxicity (H-HT):	0.66	Drug-induced Liver Injury (DILI):	0.186
AMES Toxicity:	0.238	Rat Oral Acute Toxicity:	0.286
Maximum Recommended Daily Dose:	0.307	Skin Sensitization:	0.657
Carcinogencity:	0.672	Eye Corrosion:	0.002
Eye Irritation:	0.143	Respiratory Toxicity:	0.686
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.769
Hematotoxicity:	0.422	Drug-induced Nephrotoxicity:	0.88
Genotoxicity:	0.397	RPMI-8226 Immunitoxicity:	0.04
A549 Cytotoxicity:	0.116	Hek293 Cytotoxicity:	0.192
BCF:	2.201 ? 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:	4.31 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.624 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.078 ? 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
NPO3165	Cochlospermum tinctorium	Species	Bixaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350157]
NPO3165	Cochlospermum tinctorium	Species	Bixaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553872]
NPO3165	Cochlospermum tinctorium	Species	Bixaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3165	Cochlospermum tinctorium	Species	Bixaceae	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

Activity Type	# Activity
Activity	9

Activity Type	# Activity
Cell line	4
Others	5

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
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[2553872]
NPT2	Others	Unspecified	n.a.	Activity	=	11.4	%	PMID[2553872]
NPT2	Others	Unspecified	n.a.	Activity	=	47.1	%	PMID[2553872]
NPT2	Others	Unspecified	n.a.	Activity	=	79.4	%	PMID[2553872]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[2553872]
NPT2	Others	Unspecified	n.a.	Activity	=	0.1	%	PMID[2553872]

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 NPC481361 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	13141
0.1-0.2	30775
0.2-0.3	5135
0.3-0.4	645
0.4-0.5	136
0.5-0.6	17
0.6-0.7	4
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
0.7344	Intermediate Similarity	NPC136313
0.6769	Remote Similarity	NPC246708
0.6176	Remote Similarity	NPC162107
0.6176	Remote Similarity	NPC46912
0.6119	Remote Similarity	NPC267517
0.5694	Remote Similarity	NPC481360
0.5676	Remote Similarity	NPC481363
0.5556	Remote Similarity	NPC259788
0.5556	Remote Similarity	NPC255589
0.5342	Remote Similarity	NPC488519
0.5309	Remote Similarity	NPC167383
0.5195	Remote Similarity	NPC488520
0.5181	Remote Similarity	NPC237503
0.5143	Remote Similarity	NPC235341
0.5143	Remote Similarity	NPC478657
0.5135	Remote Similarity	NPC307335
0.5135	Remote Similarity	NPC74855
0.5125	Remote Similarity	NPC488524
0.5119	Remote Similarity	NPC199457
0.507	Remote Similarity	NPC470588
0.5063	Remote Similarity	NPC488522
0.5056	Remote Similarity	NPC214484

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC481361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5797
0.1-0.2	3279
0.2-0.3	73
0.3-0.4	0
0.4-0.5	1
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