NPASS Compound

Natural Product: NPC477289

Natural Product ID	NPC477289
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-Cyano-2,3-seco-4-yliden-olean-12-enoic acid
IUPAC Name	(1S,2S,4aR,4bS,6aS,9R,10S,10aS,12aR)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-prop-1-en-2-yl-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44562528
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 78 81 0 0 0 0 0 0 0 0999 V2000 -3.2818 -2.6910 -1.0897 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1671 -2.1466 -0.0138 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1570 -1.2147 -0.6074 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4672 0.0139 -1.0380 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5825 0.6898 -0.0105 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8783 1.7554 -0.7988 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4321 1.9347 -0.5878 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6664 0.6553 -0.4861 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3138 -0.2950 0.4837 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5224 -1.1802 1.0223 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9308 -1.3696 0.8005 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5004 -0.3681 -0.1685 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7850 0.9192 -0.0139 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3715 2.0267 -0.8080 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8112 2.0530 -1.0275 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6670 0.8911 -0.6351 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9928 -0.3687 -0.2591 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5659 -0.9298 1.0243 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3093 -1.4388 -1.3218 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6705 -1.7316 -1.6749 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4809 -2.2825 -0.5937 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1330 -2.7296 0.2491 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7661 1.3394 0.3012 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0335 1.4254 -0.0789 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4454 1.7732 1.6790 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6223 1.3809 1.4255 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7438 -0.2145 0.8123 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4355 -1.4976 1.1201 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4732 -1.2871 2.2397 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7119 -0.0141 -1.8320 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5135 1.4404 0.8847 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7299 1.4294 0.6573 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0205 2.1428 1.9606 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0379 -1.9588 -1.8787 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7890 -3.5790 -1.5424 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2868 -3.0512 -0.6972 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7069 -3.0229 0.4358 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5214 -1.7176 -1.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0799 -1.0461 -0.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9300 -0.1042 -2.0005 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2748 0.7711 -1.2857 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0390 1.6456 -1.9154 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3353 2.7839 -0.6362 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2880 2.6155 0.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0357 2.5074 -1.4536 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9506 -1.8729 1.7368 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0798 -2.3879 0.3275 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4237 -1.4418 1.7661 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1234 -0.7686 -1.1732 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8585 2.0128 -1.8192 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9742 2.9893 -0.3615 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2156 2.9487 -0.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0385 2.3782 -2.0904 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2603 0.6733 -1.5848 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5407 -2.0542 0.9945 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1409 -0.5264 1.9414 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6690 -0.6866 1.0967 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7854 -2.3552 -0.9063 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6338 -1.1587 -2.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2596 -0.9335 -2.1748 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6491 -2.5459 -2.4804 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3462 1.1772 -1.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7821 1.7470 0.6184 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9090 2.8154 1.8589 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9861 1.1595 2.4313 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3921 1.7929 1.9402 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4326 1.5007 1.7375 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1021 2.3481 1.6094 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0868 0.6751 2.1426 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7195 0.2855 1.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8020 -2.2923 1.5583 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0758 -0.5386 2.9831 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6380 -2.2603 2.7844 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4479 -0.9853 1.8870 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7926 -1.1337 -1.7467 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6332 0.2758 -2.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1018 0.2849 -2.5270 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5304 2.9224 2.3922 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 2 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 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 3 0 16 23 1 0 23 24 2 0 23 25 1 0 13 26 1 1 9 27 1 0 27 28 1 0 28 29 1 0 8 30 1 6 5 31 1 1 31 32 2 0 31 33 1 0 28 2 1 0 27 5 1 0 13 8 1 0 17 12 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 1 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 6 42 1 0 6 43 1 0 7 44 1 0 7 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 12 49 1 6 14 50 1 0 14 51 1 0 15 52 1 0 15 53 1 0 16 54 1 6 18 55 1 0 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 20 60 1 0 20 61 1 0 24 62 1 0 24 63 1 0 25 64 1 0 25 65 1 0 25 66 1 0 26 67 1 0 26 68 1 0 26 69 1 0 27 70 1 1 28 71 1 1 29 72 1 0 29 73 1 0 29 74 1 0 30 75 1 0 30 76 1 0 30 77 1 0 33 78 1 0 M END

Standard InCHIKey	SXPZSMMJUUHTBE-MTCIRRIFSA-N
Standard InCHI	InChI=1S/C30H45NO2/c1-19(2)22-12-14-29(7)24(27(22,5)13-8-18-31)10-9-23-25-21(4)20(3)11-15-30(25,26(32)33)17-16-28(23,29)6/h9,20-22,24-25H,1,8,10-17H2,2-7H3,(H,32,33)/t20-,21+,22+,24-,25+,27+,28-,29-,30+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@H]([C@]4(C)CCC#N)C(=C)C)C)[C@@H]2[C@H]1C)C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	451.35	Volume:	508.605 ? Van der Waals volume.
Dense:	0.887	LogP:	4.257 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.549 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.034 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	61.09 ? 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:	0.444	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.973	Fsp³:	0.8
MCE-18:	82.963 ? 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:	0.762	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.049 ? 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:	0.254	Promiscuous compounds:	0.074

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.372	MDCK Permeability:	-4.846
Pgp-inhibitor:	0.807	Pgp-substrate:	0.0
PAMPA:	0.861 ? 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):	0.001
20% Bioavailability (F20%):	0.077	30% Bioavailability (F30%):	0.11
50% Bioavailability (F50%):	0.661

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.383	MRP1:	0.934
Plasma Protein Binding (PPB):	84.987%	Volume Distribution (VD):	-0.058
Fu:	10.992% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.82	BCRP inhibitor:	0.074
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.931	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.987	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.993	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.001 ? 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):

4.379

Half-life (T1/2):

0.631

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.239
Human Hepatotoxicity (H-HT):	0.618	Drug-induced Liver Injury (DILI):	0.259
AMES Toxicity:	0.143	Rat Oral Acute Toxicity:	0.467
Maximum Recommended Daily Dose:	0.824	Skin Sensitization:	0.929
Carcinogencity:	0.77	Eye Corrosion:	0.03
Eye Irritation:	0.839	Respiratory Toxicity:	0.992
Drug-induced Neurotoxicity:	0.212	Ototoxicity:	0.726
Hematotoxicity:	0.477	Drug-induced Nephrotoxicity:	0.634
Genotoxicity:	0.652	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.061	Hek293 Cytotoxicity:	0.162
BCF:	1.074 ? 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:	3.845 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.376 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.723 ? 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
NPO26571	Ilex paraguariensis	Species	Aquifoliaceae	Eukaryota	leaves	Mato Leitao, RS, Brazil	n.a.	PMID[18192087]
NPO26571	Ilex paraguariensis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25955847]
NPO26571	Ilex paraguariensis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26571	Ilex paraguariensis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26571	Ilex paraguariensis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26571	Ilex paraguariensis	Species	Aquifoliaceae	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
IC50	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual protein	Cytochrome P450 19A1	Homo sapiens	IC50	>	500000	nM	PMID[18192087]

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 NPC477289 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	28923
0.1-0.2	18057
0.2-0.3	2288
0.3-0.4	403
0.4-0.5	149
0.5-0.6	19
0.6-0.7	17
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
0.7121	Intermediate Similarity	NPC87095
0.6567	Remote Similarity	NPC51700
0.6567	Remote Similarity	NPC88716
0.6567	Remote Similarity	NPC68160
0.6515	Remote Similarity	NPC274050
0.6515	Remote Similarity	NPC162632
0.6471	Remote Similarity	NPC61543
0.6471	Remote Similarity	NPC293048
0.6471	Remote Similarity	NPC225585
0.6471	Remote Similarity	NPC71074
0.6471	Remote Similarity	NPC605937
0.6377	Remote Similarity	NPC173089
0.6377	Remote Similarity	NPC32407
0.6377	Remote Similarity	NPC263548
0.6377	Remote Similarity	NPC477288
0.6377	Remote Similarity	NPC606320
0.6081	Remote Similarity	NPC230151
0.6056	Remote Similarity	NPC485589
0.5972	Remote Similarity	NPC477290
0.5915	Remote Similarity	NPC305464
0.5915	Remote Similarity	NPC19376
0.5915	Remote Similarity	NPC25848
0.5733	Remote Similarity	NPC485586
0.5733	Remote Similarity	NPC485588
0.5588	Remote Similarity	NPC107039
0.5493	Remote Similarity	NPC274330
0.5375	Remote Similarity	NPC485585
0.5366	Remote Similarity	NPC57362
0.5342	Remote Similarity	NPC37221
0.5301	Remote Similarity	NPC177246
0.527	Remote Similarity	NPC293564
0.5181	Remote Similarity	NPC485882
0.5132	Remote Similarity	NPC127689
0.5132	Remote Similarity	NPC25299
0.5132	Remote Similarity	NPC481322
0.5065	Remote Similarity	NPC20235
0.5065	Remote Similarity	NPC299996

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7048
0.1-0.2	2070
0.2-0.3	27
0.3-0.4	5
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