NPASS Compound

Natural Product: NPC471901

Natural Product ID	NPC471901
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Acetyl-Lupeolic Acid
IUPAC Name	(1R,3aR,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-3a,5a,5b,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3289106
PubChem CID	90644331
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 86 90 0 0 0 0 0 0 0 0999 V2000 -4.4222 -2.8154 -0.2736 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1885 -1.6528 -0.8702 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4854 -1.7230 -0.7042 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5056 -0.6067 -1.5662 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3721 0.4961 -2.1135 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3497 1.5960 -1.0407 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3326 1.1100 0.0174 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5249 0.2377 -0.8294 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2570 -0.3567 -0.3782 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4741 -0.6338 -1.6375 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0342 -0.4462 -1.6348 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5853 0.5648 -0.7095 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0673 0.3595 -0.7693 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8414 1.6965 -0.6562 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3005 1.4214 -0.9541 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8925 0.2542 -0.2931 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0269 -0.8916 0.1407 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6325 -0.4478 0.3361 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6871 -1.4767 0.8931 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3016 -1.0119 1.0807 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0455 0.3900 0.6607 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5350 0.5537 0.5773 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9525 1.9471 0.2085 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4096 2.2398 0.4427 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0793 0.2931 1.9875 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3519 1.4632 1.6478 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5127 -1.2538 1.5839 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2814 -2.1373 -0.5677 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4306 -2.7813 -1.1918 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5641 -2.6593 -0.5557 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7604 0.6524 0.7715 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1137 0.4881 0.7928 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6638 -0.0584 -0.1995 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8707 0.9582 1.9778 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4658 -0.0676 -2.1645 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1557 0.5506 1.1039 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0559 -3.7534 -0.3168 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5357 -3.0826 -0.8771 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2324 -2.6784 0.8062 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9898 -2.5428 -0.1834 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1420 -0.9612 -1.0696 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9444 -1.0835 -2.4352 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3985 0.2196 -2.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8792 0.9155 -3.0486 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3404 1.7691 -0.6093 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9059 2.5204 -1.4735 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2078 0.9729 -1.6606 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3960 -1.2981 0.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7201 -1.7074 -1.9051 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9239 -0.0907 -2.5300 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2531 -0.2085 -2.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4395 -1.4617 -1.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3229 1.5739 -1.0801 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8391 1.9398 0.4257 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4588 2.4559 -1.3218 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8276 2.3473 -0.5490 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5413 1.5367 -2.0546 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6137 -0.1999 -1.0458 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7657 0.2603 1.2307 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6874 -2.4358 0.3140 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1725 -1.8129 1.8662 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4106 -1.6640 0.4818 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0195 -1.2628 2.1330 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3905 2.7626 0.6840 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7116 2.0735 -0.8901 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6462 3.0930 -0.2646 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6420 2.6379 1.4379 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6695 -0.6673 1.9813 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3021 0.0952 2.7415 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6304 1.1534 2.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0319 1.1752 2.4350 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5266 1.8726 2.2492 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6181 2.3702 1.0571 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6259 -1.3404 1.5115 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1777 -0.4936 2.2926 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1536 -2.2751 1.8211 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9207 -3.2238 -1.3417 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8255 0.4175 2.0803 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1245 2.0467 1.8500 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2920 0.8087 2.9115 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0294 -0.9749 -2.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5668 -0.2066 -2.2804 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2776 0.8317 -2.8322 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2609 0.6245 0.9605 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9816 1.1807 2.0290 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9673 -0.4816 1.4133 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 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 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 1 0 21 22 1 0 22 23 1 0 23 24 1 0 22 25 1 0 21 26 1 0 17 27 1 0 17 28 1 0 28 29 2 0 28 30 1 0 16 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 13 35 1 0 7 36 1 0 8 4 1 0 24 7 1 0 22 9 1 0 21 12 1 0 18 13 1 0 1 37 1 0 1 38 1 0 1 39 1 0 3 40 1 0 3 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 8 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 12 53 1 0 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 23 64 1 0 23 65 1 0 24 66 1 0 24 67 1 0 25 68 1 0 25 69 1 0 25 70 1 0 26 71 1 0 26 72 1 0 26 73 1 0 27 74 1 0 27 75 1 0 27 76 1 0 30 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 36 84 1 0 36 85 1 0 36 86 1 0 M END

Standard InCHIKey	DULLEXJVWYWBKQ-VDHVTXALSA-N
Standard InCHI	InChI=1S/C32H50O4/c1-19(2)21-11-14-28(4)17-18-30(6)22(26(21)28)9-10-23-29(5)15-13-25(36-20(3)33)32(8,27(34)35)24(29)12-16-31(23,30)7/h21-26H,1,9-18H2,2-8H3,(H,34,35)/t21-,22+,23+,24+,25-,26+,28+,29+,30+,31+,32+/m0/s1
SMILES	CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C(=O)O)OC(=O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	498.37	Volume:	546.497 ? Van der Waals volume.
Dense:	0.912	LogP:	4.453 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.851 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.524 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	28.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.32	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.879	Fsp³:	0.875
MCE-18:	105.3 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.251	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.047 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.326	Promiscuous compounds:	0.035

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.177	MDCK Permeability:	-4.87
Pgp-inhibitor:	0.005	Pgp-substrate:	0.0
PAMPA:	0.063 ? 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%):	0.0	30% Bioavailability (F30%):	0.008
50% Bioavailability (F50%):	0.832

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.887	MRP1:	1.0
Plasma Protein Binding (PPB):	95.624%	Volume Distribution (VD):	-0.184
Fu:	4.113% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.002
OATP1B3 inhibitor:	0.86	BCRP inhibitor:	0.0
BSEP inhibitor:	0.98

ADMET: Metabolism

CYP1A2-inhibitor:	0.163	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.029
CYP2C9-inhibitor:	0.536	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.251	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.129	CYP3A4-substrate:	0.031
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.984 ? 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):

2.654

Half-life (T1/2):

1.364

ADMET: Toxicity

hERG Blockers:	0.056	hERG Blockers (10um):	0.264
Human Hepatotoxicity (H-HT):	0.509	Drug-induced Liver Injury (DILI):	0.316
AMES Toxicity:	0.028	Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.714	Skin Sensitization:	0.038
Carcinogencity:	0.462	Eye Corrosion:	0.011
Eye Irritation:	0.303	Respiratory Toxicity:	0.467
Drug-induced Neurotoxicity:	0.117	Ototoxicity:	0.884
Hematotoxicity:	0.104	Drug-induced Nephrotoxicity:	0.081
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.015
A549 Cytotoxicity:	0.021	Hek293 Cytotoxicity:	0.102
BCF:	1.177 ? 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:	4.853 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.269 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.414 ? 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
NPO33055	boswellia spp.	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24844534]

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	1
IC50	6

Activity Type	# Activity
Individual protein	4
Cell line	1
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual protein	Cyclooxygenase-1	Ovis aries	IC50	>	10000.0	nM	PMID[18222568]
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	IC50	>	10000.0	nM	PMID[23149304]
NPT956	Individual protein	Prostaglandin E synthase	Homo sapiens	Activity	=	51.4	%	PMID[10543899]
NPT956	Individual protein	Prostaglandin E synthase	Homo sapiens	IC50	=	10000.0	nM	PMID[8126698]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT136	Cell line	SK-N-SH	Homo sapiens	IC50	=	4100.0	nM	PMID[21970540]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	4100.0	nM	PMID[24844534]

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 NPC471901 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	22937
0.1-0.2	23158
0.2-0.3	3347
0.3-0.4	335
0.4-0.5	63
0.5-0.6	13
0.6-0.7	2
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8095	Intermediate Similarity	NPC471902
0.7937	Intermediate Similarity	NPC287118
0.6452	Remote Similarity	NPC305835
0.6154	Remote Similarity	NPC471900
0.5821	Remote Similarity	NPC611062
0.5417	Remote Similarity	NPC23621
0.5417	Remote Similarity	NPC184006
0.5286	Remote Similarity	NPC473742
0.5286	Remote Similarity	NPC261616
0.527	Remote Similarity	NPC475416
0.5217	Remote Similarity	NPC98270
0.52	Remote Similarity	NPC78580
0.5139	Remote Similarity	NPC4309
0.5077	Remote Similarity	NPC43300
0.507	Remote Similarity	NPC35751
0.5067	Remote Similarity	NPC195715
0.5065	Remote Similarity	NPC239362

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471901 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5652
0.1-0.2	3414
0.2-0.3	78
0.3-0.4	4
0.4-0.5	2
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