NPASS Compound

Natural Product: NPC156745

Natural Product ID	NPC156745
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ALKHEZOKTHCOBM-MGZHOKCZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL518848
PubChem CID	5281385
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane 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 77 80 0 0 0 0 0 0 0 0999 V2000 9.0304 0.2577 -1.1196 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8663 -0.0574 -2.0168 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7763 0.9887 -1.8772 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3514 0.9612 -0.4423 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0716 0.6735 -0.1100 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6998 0.6560 1.2708 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4885 0.3885 1.6817 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4000 0.0837 0.8002 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4396 0.0286 -0.4474 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1089 -0.1968 1.3207 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0074 -0.4968 0.5317 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9094 0.7142 0.5829 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0239 1.8573 0.0335 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0848 0.4943 -0.3186 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8363 1.7517 -0.4283 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8583 2.6581 0.7279 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9059 3.4762 0.5681 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3156 4.5716 1.5074 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6153 3.1120 -0.6591 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3031 3.8151 -1.4063 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2893 1.6659 -0.7708 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4447 1.0678 -2.1177 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4698 -0.4127 -1.9036 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8261 -1.1200 -1.0222 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8461 -0.7057 0.0727 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0887 -1.8989 0.4788 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5663 -2.1143 1.8510 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6815 -1.1349 2.9625 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5750 -3.5633 2.3789 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6574 -1.7993 0.7062 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1453 -2.9206 0.3457 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2918 -3.3331 0.9355 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7422 -2.7284 1.9112 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0553 -4.5307 0.4327 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3503 -1.1477 -2.8298 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6751 -0.6785 -2.6714 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5183 0.2049 -1.5906 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9856 1.3458 -0.8524 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0035 0.1217 -1.6499 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9835 -0.3006 -0.1793 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4234 -1.0255 -1.7082 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2318 -0.1395 -3.0588 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9655 0.7060 -2.5486 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2353 1.9709 -2.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0570 1.1698 0.3473 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4600 0.4833 -0.9736 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4803 0.8798 2.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2674 0.3910 2.7507 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3739 -0.4751 -0.5419 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1839 1.0449 1.5776 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3327 1.6192 -0.9998 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5529 2.8019 -0.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8774 1.9943 0.6504 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3750 2.3624 -1.2660 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2292 2.7601 1.6049 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0299 4.3019 2.5379 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3545 4.8844 1.3838 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6685 5.4494 1.2125 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8730 1.1030 0.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3485 1.4131 -2.6635 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5843 1.2774 -2.7848 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0118 -2.1841 -1.0647 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5420 -0.3940 0.9100 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4239 -2.8654 -0.0206 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6938 -0.6626 3.1377 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5214 -0.4210 2.8537 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8996 -1.6160 3.9697 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9408 -3.6600 3.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3676 -4.2798 1.5775 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6274 -3.7499 2.7149 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7877 -4.2625 -0.3280 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2782 -5.1761 -0.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4650 -5.1100 1.2801 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0738 -0.8616 -3.8689 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3744 -2.2242 -2.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8147 -0.3393 -1.7371 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3361 1.0787 -2.0117 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 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 17 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 27 30 1 0 30 31 1 6 31 32 1 0 32 33 2 0 32 34 1 0 23 35 1 0 35 36 1 0 14 37 1 6 30 11 1 0 25 14 1 0 30 26 1 0 21 15 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 0 2 42 1 0 3 43 1 0 3 44 1 0 4 45 1 0 5 46 1 0 6 47 1 0 7 48 1 0 11 49 1 6 12 50 1 1 13 51 1 0 13 52 1 0 13 53 1 0 15 54 1 6 16 55 1 0 18 56 1 0 18 57 1 0 18 58 1 0 21 59 1 1 22 60 1 0 22 61 1 0 24 62 1 0 25 63 1 1 26 64 1 6 28 65 1 0 28 66 1 0 28 67 1 0 29 68 1 0 29 69 1 0 29 70 1 0 34 71 1 0 34 72 1 0 34 73 1 0 35 74 1 0 35 75 1 0 36 76 1 0 37 77 1 0 M END

Standard InCHIKey	ALKHEZOKTHCOBM-MGZHOKCZSA-N
Standard InCHI	InChI=1S/C30H40O7/c1-7-8-9-10-11-12-24(33)36-27-18(3)29(35)22-13-17(2)25(34)21(22)14-20(16-31)15-23(29)26-28(5,6)30(26,27)37-19(4)32/h9-13,15,18,21-23,26-27,31,35H,7-8,14,16H2,1-6H3/b10-9+,12-11-/t18-,21+,22-,23+,26-,27-,29+,30-/m1/s1
SMILES	CCC/C=C/C=CC(=O)O[C@@H]1[C@@H](C)[C@@]2([C@@H]3C=C(C)C(=O)[C@H]3CC(=C[C@H]2[C@@H]2C(C)(C)[C@]12OC(=O)C)CO)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.28	Volume:	536.287 ? Van der Waals volume.
Dense:	0.955	LogP:	3.429 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.5 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.411 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	23.0
TPSA:	110.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.231	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.312	Fsp³:	0.633
MCE-18:	77.061 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.554	Fluc inhibitor:	0.049 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.044 ? 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:	0.344	Promiscuous compounds:	0.369

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.342	MDCK Permeability:	-5.006
Pgp-inhibitor:	0.909	Pgp-substrate:	0.595
PAMPA:	0.867 ? 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):	0.141
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.295
Plasma Protein Binding (PPB):	74.986%	Volume Distribution (VD):	-0.327
Fu:	20.288% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.964	BCRP inhibitor:	0.001
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.168	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.501
CYP3A4-inhibitor:	0.024	CYP3A4-substrate:	0.99
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.985
HLM stability:	0.762 ? 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):

7.012

Half-life (T1/2):

0.944

ADMET: Toxicity

hERG Blockers:	0.096	hERG Blockers (10um):	0.335
Human Hepatotoxicity (H-HT):	0.849	Drug-induced Liver Injury (DILI):	0.538
AMES Toxicity:	0.955	Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.865	Skin Sensitization:	1.0
Carcinogencity:	0.758	Eye Corrosion:	0.001
Eye Irritation:	0.464	Respiratory Toxicity:	0.884
Drug-induced Neurotoxicity:	0.374	Ototoxicity:	0.574
Hematotoxicity:	0.25	Drug-induced Nephrotoxicity:	0.808
Genotoxicity:	0.441	RPMI-8226 Immunitoxicity:	0.199
A549 Cytotoxicity:	0.483	Hek293 Cytotoxicity:	0.752
BCF:	0.936 ? 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:	3.753 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.514 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.913 ? 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
NPO7612	Euphorbia tirucalli	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[469552]
NPO7612	Euphorbia tirucalli	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7612	Euphorbia tirucalli	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7612	Euphorbia tirucalli	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7612	Euphorbia tirucalli	Species	Euphorbiaceae	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
ID50	2

Activity Type	# Activity
Organism	2

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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.04	ug	PMID[22264170]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.07	ug	PMID[10217738]

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 NPC156745 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	18830
0.1-0.2	29301
0.2-0.3	1564
0.3-0.4	79
0.4-0.5	41
0.5-0.6	18
0.6-0.7	13
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC236918
0.9118	High Similarity	NPC482221
0.9091	High Similarity	NPC608501
0.8986	High Similarity	NPC482220
0.8571	High Similarity	NPC472759
0.8472	Intermediate Similarity	NPC482219
0.7838	Intermediate Similarity	NPC482222
0.7286	Intermediate Similarity	NPC154363
0.7246	Intermediate Similarity	NPC482406
0.7222	Intermediate Similarity	NPC485737
0.7123	Intermediate Similarity	NPC476111
0.7042	Intermediate Similarity	NPC472757
0.6923	Remote Similarity	NPC329080
0.6883	Remote Similarity	NPC145238
0.6806	Remote Similarity	NPC481522
0.68	Remote Similarity	NPC90814
0.68	Remote Similarity	NPC189393
0.6757	Remote Similarity	NPC475885
0.6712	Remote Similarity	NPC481520
0.6622	Remote Similarity	NPC234858
0.6622	Remote Similarity	NPC179207
0.6447	Remote Similarity	NPC471127
0.6447	Remote Similarity	NPC481525
0.6447	Remote Similarity	NPC481531
0.641	Remote Similarity	NPC10721
0.5952	Remote Similarity	NPC482199
0.5952	Remote Similarity	NPC482197
0.5897	Remote Similarity	NPC485734
0.5814	Remote Similarity	NPC482198
0.5802	Remote Similarity	NPC478999
0.5732	Remote Similarity	NPC484333
0.5698	Remote Similarity	NPC140021
0.5595	Remote Similarity	NPC481523
0.5568	Remote Similarity	NPC112752
0.5568	Remote Similarity	NPC311054
0.5568	Remote Similarity	NPC479001
0.5568	Remote Similarity	NPC479002
0.5465	Remote Similarity	NPC611138
0.5375	Remote Similarity	NPC482405
0.5287	Remote Similarity	NPC482200
0.5244	Remote Similarity	NPC481528
0.5063	Remote Similarity	NPC600179
0.5063	Remote Similarity	NPC602150

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC156745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6711
0.1-0.2	2404
0.2-0.3	35
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