NPASS Compound

Natural Product: NPC259644

Natural Product ID	NPC259644
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	N-Arachidoyltryptamine
IUPAC Name	N-[2-(1H-indol-3-yl)ethyl]icosanamide
Synonyms	N-Arachidoyltryptamine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL491708
PubChem CID	10127573
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

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 84 0 0 0 0 0 0 0 0999 V2000 -5.1930 1.8434 3.6197 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0324 1.5444 2.4214 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2536 1.1365 1.2061 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4295 -0.1020 1.4095 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1628 -1.3206 1.7735 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2451 -1.8707 0.9676 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0497 -2.3197 -0.4248 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6778 -1.2095 -1.3536 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5458 -1.7238 -2.7946 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5026 -2.7809 -2.9441 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1160 -2.3240 -2.5501 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6832 -1.1547 -3.4107 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2745 -0.7359 -2.9814 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2306 -0.3245 -1.5598 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2090 0.1217 -1.2052 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1149 -1.0162 -1.4089 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5351 -0.9772 -1.0587 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4171 0.0141 -1.6803 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2247 1.4668 -1.3725 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4255 1.6951 0.0705 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3067 2.4677 0.5243 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2329 3.2348 -0.2107 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5147 2.4933 -0.5072 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2547 2.0848 0.6939 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3302 2.8103 1.2159 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7652 2.1955 2.3236 N 0 0 0 0 0 0 0 0 0 0 0 0 8.0304 1.0925 2.5655 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0962 1.0290 1.5518 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2227 -0.0185 1.5636 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2264 -1.0111 2.5352 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1659 -0.9280 3.5383 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0535 0.1223 3.5382 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6106 1.0338 0.9764 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8562 0.8682 4.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8746 2.2859 4.3926 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3732 2.5447 3.4496 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8061 0.8156 2.7119 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5831 2.4799 2.1491 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5173 1.9723 1.0135 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9184 1.1177 0.3452 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6771 -0.2086 0.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7833 0.1412 2.3456 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4489 -1.2942 2.8952 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3582 -2.1481 1.8237 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1439 -1.1470 0.9100 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6763 -2.7472 1.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2953 -3.1582 -0.4815 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0194 -2.8136 -0.7619 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7337 -0.7422 -1.1277 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5270 -0.4656 -1.4205 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3472 -0.8230 -3.4067 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5141 -2.1287 -3.1486 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4828 -3.1602 -4.0096 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7761 -3.6725 -2.3514 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4299 -3.1757 -2.6708 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1735 -2.0301 -1.4865 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3534 -0.2962 -3.2461 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6020 -1.4685 -4.4705 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6654 -1.6623 -3.2096 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9384 0.0980 -3.6186 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9253 0.5124 -1.4125 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4674 -1.1335 -0.8435 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3515 0.9432 -1.9878 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2406 0.5237 -0.1942 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0736 -1.3872 -2.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6211 -1.9058 -0.8721 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6758 -1.0369 0.0706 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9487 -2.0149 -1.4063 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5119 -0.2371 -1.4147 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4518 -0.1418 -2.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2304 1.8601 -1.6163 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0068 2.0666 -1.9637 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4819 4.1812 0.3875 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7838 3.6241 -1.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1269 3.1360 -1.1765 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2304 1.6036 -1.1106 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7206 3.7197 0.7678 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5569 2.5192 2.9162 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4973 -0.0816 0.7658 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4951 -1.8171 2.4768 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1825 -1.7064 4.3169 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7866 0.1691 4.3386 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9534 0.8534 1.9117 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 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 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 3 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 20 33 1 0 28 24 1 0 32 27 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 0 2 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 7 47 1 0 7 48 1 0 8 49 1 0 8 50 1 0 9 51 1 0 9 52 1 0 10 53 1 0 10 54 1 0 11 55 1 0 11 56 1 0 12 57 1 0 12 58 1 0 13 59 1 0 13 60 1 0 14 61 1 0 14 62 1 0 15 63 1 0 15 64 1 0 16 65 1 0 16 66 1 0 17 67 1 0 17 68 1 0 18 69 1 0 18 70 1 0 19 71 1 0 19 72 1 0 22 73 1 0 22 74 1 0 23 75 1 0 23 76 1 0 25 77 1 0 26 78 1 0 29 79 1 0 30 80 1 0 31 81 1 0 32 82 1 0 33 83 1 0 M END

Standard InCHIKey	PMYMGHIVWFOOOS-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C30H50N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23-30(33)31-25-24-27-26-32-29-22-20-19-21-28(27)29/h19-22,26,32H,2-18,23-25H2,1H3,(H,31,33)
SMILES	CCCCCCCCCCCCCCCCCCCC(=NCCc1c[nH]c2c1cccc2)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.39	Volume:	527.925 ? Van der Waals volume.
Dense:	0.861	LogP:	8.496 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.563 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.299 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	21.0	Rigid Bonds:	11.0
TPSA:	48.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.11	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.486	Fsp³:	0.7
MCE-18:	10.0 ? 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:	0.715	Fluc inhibitor:	0.018 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.058 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.35 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.006	Promiscuous compounds:	0.246

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.057	MDCK Permeability:	-4.859
Pgp-inhibitor:	0.0	Pgp-substrate:	0.271
PAMPA:	0.0 ? 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):	0.925
20% Bioavailability (F20%):	0.981	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.901
Plasma Protein Binding (PPB):	100.237%	Volume Distribution (VD):	1.579
Fu:	0.627% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.674
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.972
BSEP inhibitor:	0.799

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.1	CYP2C19-substrate:	0.44
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.535
CYP3A4-inhibitor:	0.512	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.359	CYP2C8-inhibitor:	1.0
HLM stability:	0.777 ? 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):

4.924

Half-life (T1/2):

1.202

ADMET: Toxicity

hERG Blockers:	0.582	hERG Blockers (10um):	0.839
Human Hepatotoxicity (H-HT):	0.829	Drug-induced Liver Injury (DILI):	0.342
AMES Toxicity:	0.218	Rat Oral Acute Toxicity:	0.532
Maximum Recommended Daily Dose:	0.603	Skin Sensitization:	0.998
Carcinogencity:	0.66	Eye Corrosion:	0.008
Eye Irritation:	0.889	Respiratory Toxicity:	0.992
Drug-induced Neurotoxicity:	0.03	Ototoxicity:	0.435
Hematotoxicity:	0.249	Drug-induced Nephrotoxicity:	0.413
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.013
A549 Cytotoxicity:	0.64	Hek293 Cytotoxicity:	0.136
BCF:	0.837 ? 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:	5.004 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.398 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.208 ? 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
NPO32731	rollinia mucosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10479316]
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20579892]
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23513739]
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26920282]
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
ED50	6
Activity	2

Activity Type	# Activity
Cell line	7
Non-molecular	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
NPT81	Cell line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[20409719]
NPT83	Cell line	MCF7	Homo sapiens	ED50	>	10.0	ug ml-1	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	ED50	>	10.0	ug ml-1	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[23434131]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[23434131]
NPT4564	Cell line	Neurons	n.a.	Activity	=	121.8	%	PMID[21859082]
NPT4564	Cell line	Neurons	n.a.	Activity	=	147.4	%	PMID[23891163]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[10479316]

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
-	Artemia salina	LC50	>	500.0	ug.mL-1	PMID[24601675]

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 NPC259644 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	34292
0.1-0.2	14042
0.2-0.3	1107
0.3-0.4	293
0.4-0.5	90
0.5-0.6	10
0.6-0.7	1
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC70922
1.0	High Similarity	NPC211572
1.0	High Similarity	NPC75540
1.0	High Similarity	NPC212376
1.0	High Similarity	NPC469765
1.0	High Similarity	NPC80597
1.0	High Similarity	NPC25008
1.0	High Similarity	NPC73952
0.8475	Intermediate Similarity	NPC469763
0.75	Intermediate Similarity	NPC190296
0.7333	Intermediate Similarity	NPC105818
0.7273	Intermediate Similarity	NPC311276
0.6769	Remote Similarity	NPC24678
0.5968	Remote Similarity	NPC469760
0.5968	Remote Similarity	NPC469786
0.5932	Remote Similarity	NPC471957
0.5254	Remote Similarity	NPC59269
0.5195	Remote Similarity	NPC486585
0.5156	Remote Similarity	NPC279918
0.5143	Remote Similarity	NPC75907
0.5079	Remote Similarity	NPC282231
0.5079	Remote Similarity	NPC267885
0.5068	Remote Similarity	NPC277920

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC259644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3837
0.1-0.2	5086
0.2-0.3	155
0.3-0.4	54
0.4-0.5	17
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