NPASS Compound

Natural Product: NPC48637

Natural Product ID	NPC48637
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AKNNEGZIBPJZJG-QNSVNVJESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	19728
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002188] Phthalide isoquinolines

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 53 57 0 0 0 0 0 0 0 0999 V2000 -0.3732 -3.3334 -0.7157 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8325 -1.9954 -0.8875 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8372 -1.9513 -1.9036 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7763 -0.5345 -2.4844 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2480 0.3238 -1.3247 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9506 1.4468 -1.6561 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4501 2.2503 -0.6689 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2045 1.8617 0.6299 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4956 0.7292 0.9704 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9826 -0.0927 -0.0325 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2081 -1.2901 0.2809 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0202 -1.0102 1.1828 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0422 -0.2538 0.5322 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0934 0.9842 -0.0817 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2813 1.4784 -0.6290 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4394 0.7131 -0.5575 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4047 -0.5238 0.0515 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2102 -0.9738 0.5789 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9230 -2.2296 1.2525 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7471 -3.1477 1.4824 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5864 -2.2080 1.5816 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5592 -1.2930 0.1258 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4792 -1.2425 1.1773 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6415 1.1369 -1.0741 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8714 2.3511 -1.7226 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3318 0.4660 2.3215 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2107 -0.2948 3.0977 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8078 2.8290 1.4483 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2390 3.9248 0.6743 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1882 3.4323 -0.6567 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9588 -3.9923 -1.4093 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6801 -3.4792 -1.0324 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5712 -3.7600 0.3033 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8590 -2.0408 -1.4648 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7157 -2.7046 -2.6993 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4967 -0.4606 -3.3057 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7489 -0.3403 -2.7648 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1376 1.7418 -2.6894 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8817 -1.9680 0.8848 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3331 -0.4822 2.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2371 1.6204 -0.1688 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3340 2.4332 -1.1060 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4687 -0.2794 1.7306 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4998 -1.3736 0.7188 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3610 -2.0637 1.9123 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9301 2.6501 -1.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8506 2.2530 -2.8446 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2161 3.1734 -1.3733 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9288 -0.8862 2.5284 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7017 0.3828 3.8372 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5749 -0.9934 3.7156 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5235 4.7778 0.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2685 4.2386 0.9027 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 17 22 1 0 22 23 1 0 16 24 1 0 24 25 1 0 9 26 1 0 26 27 1 0 8 28 1 0 28 29 1 0 29 30 1 0 11 2 1 0 21 12 1 0 10 5 1 0 18 13 1 0 30 7 1 0 1 31 1 0 1 32 1 0 1 33 1 0 3 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 6 38 1 0 11 39 1 1 12 40 1 0 14 41 1 0 15 42 1 0 23 43 1 0 23 44 1 0 23 45 1 0 25 46 1 0 25 47 1 0 25 48 1 0 27 49 1 0 27 50 1 0 27 51 1 0 29 52 1 0 29 53 1 0 M END

Standard InCHIKey	AKNNEGZIBPJZJG-QNSVNVJESA-N
Standard InCHI	InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18?/m1/s1
SMILES	CN1CCc2cc3c(c(c2[C@@H]1C1c2ccc(c(c2C(=O)O1)OC)OC)OC)OCO3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	413.15	Volume:	400.359 ? Van der Waals volume.
Dense:	1.032	LogP:	1.989 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.241 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.683 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	26.0
TPSA:	75.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.709	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.553	Fsp³:	0.409
MCE-18:	93.032 ? 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:	0.102	Fluc inhibitor:	0.04 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.492 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.626 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.003	Promiscuous compounds:	0.305

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.77	MDCK Permeability:	-4.711
Pgp-inhibitor:	0.958	Pgp-substrate:	0.021
PAMPA:	0.016 ? 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%):	0.017	30% Bioavailability (F30%):	0.008
50% Bioavailability (F50%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968	MRP1:	0.977
Plasma Protein Binding (PPB):	71.63%	Volume Distribution (VD):	0.218
Fu:	29.782% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.993
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.669
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.996
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.247	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.399	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.765
CYP2B6-substrate:	0.936	CYP2C8-inhibitor:	0.0
HLM stability:	0.997 ? 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):

4.601

Half-life (T1/2):

2.216

ADMET: Toxicity

hERG Blockers:	0.165	hERG Blockers (10um):	0.639
Human Hepatotoxicity (H-HT):	0.334	Drug-induced Liver Injury (DILI):	0.264
AMES Toxicity:	0.5	Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.55	Skin Sensitization:	0.819
Carcinogencity:	0.811	Eye Corrosion:	0.018
Eye Irritation:	0.597	Respiratory Toxicity:	0.214
Drug-induced Neurotoxicity:	0.729	Ototoxicity:	0.42
Hematotoxicity:	0.229	Drug-induced Nephrotoxicity:	0.367
Genotoxicity:	0.552	RPMI-8226 Immunitoxicity:	0.061
A549 Cytotoxicity:	0.049	Hek293 Cytotoxicity:	0.192
BCF:	1.534 ? 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:	3.93 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.229 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.895 ? 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
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1042/BA20020118]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1556/abot.45.2003.3-4.15]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33937995]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34771092]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35143705]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37049761]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37685099]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38159180]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19787	Citrus sinensis	Species	Rutaceae	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

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

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 NPC48637 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	33260
0.1-0.2	15093
0.2-0.3	1323
0.3-0.4	147
0.4-0.5	18
0.5-0.6	1
0.6-0.7	4
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC119818
1.0	High Similarity	NPC328700
1.0	High Similarity	NPC202771
1.0	High Similarity	NPC2173
0.7812	Intermediate Similarity	NPC14622
0.7812	Intermediate Similarity	NPC70290
0.7812	Intermediate Similarity	NPC215098
0.7812	Intermediate Similarity	NPC124302
0.7812	Intermediate Similarity	NPC73020
0.7164	Intermediate Similarity	NPC46744
0.6866	Remote Similarity	NPC120671
0.6866	Remote Similarity	NPC226652
0.6866	Remote Similarity	NPC219113
0.6866	Remote Similarity	NPC72788
0.5065	Remote Similarity	NPC481430

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC48637 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5196
0.1-0.2	3781
0.2-0.3	162
0.3-0.4	7
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD5005	Approved
1.0	High Similarity	NPD5006	Phase 4
0.7812	Intermediate Similarity	NPD4420	Pre-clinical
0.6364	Remote Similarity	NPD6625	Phase 4

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