NPASS Compound

Structure

NPC275393 OpenBabel07101719512D 58 59 0 0 1 0 0 0 0 0999 V2000 -8.3391 7.9999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1442 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4216 0.1801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2217 5.3338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9443 5.1527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4144 5.1081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4325 3.7068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8506 -0.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5551 1.3110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1120 4.6096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8848 1.2193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3713 3.3894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4578 2.9826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6488 3.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6918 4.9270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5370 2.7123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4255 7.5931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5120 7.1864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4075 6.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4939 5.7851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7861 -1.9305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3894 4.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7916 -2.0350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9941 -0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3352 0.5868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0307 4.7460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5189 4.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7461 0.7232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1984 4.2028 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0758 1.8070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4397 1.5814 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9262 3.7514 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7099 3.5258 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8325 1.1300 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0939 3.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1623 1.4003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6307 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0126 3.3447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8144 2.5312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0235 0.5422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1803 2.8016 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3532 1.9881 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7352 3.1637 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7964 3.9325 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7280 2.1245 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1280 -0.4523 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9029 2.6205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0577 0.4058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7171 1.7624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0919 2.3502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0054 1.9435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1100 0.9489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 3 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 29 1 0 0 0 0 8 30 1 0 0 0 0 9 30 1 0 0 0 0 12 46 1 0 0 0 0 13 47 1 0 0 0 0 14 48 1 0 0 0 0 15 49 1 0 0 0 0 16 50 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 21 25 1 0 0 0 0 22 31 1 0 0 0 0 23 33 1 0 0 0 0 24 26 2 0 0 0 0 24 45 1 0 0 0 0 25 51 1 0 0 0 0 26 58 1 0 0 0 0 31 10 1 6 0 0 0 31 39 1 0 0 0 0 32 11 1 6 0 0 0 32 40 1 0 0 0 0 32 46 1 0 0 0 0 33 38 1 1 0 0 0 33 51 1 0 0 0 0 34 27 1 6 0 0 0 34 41 1 0 0 0 0 34 47 1 0 0 0 0 35 28 1 1 0 0 0 35 42 1 0 0 0 0 35 48 1 0 0 0 0 36 29 1 1 0 0 0 36 43 1 0 0 0 0 36 49 1 0 0 0 0 37 30 1 1 0 0 0 37 44 1 0 0 0 0 37 50 1 0 0 0 0 38 45 2 0 0 0 0 38 58 1 0 0 0 0 39 46 1 0 0 0 0 39 52 2 0 0 0 0 40 47 1 0 0 0 0 40 53 2 0 0 0 0 41 48 1 0 0 0 0 41 54 2 0 0 0 0 42 49 1 0 0 0 0 42 55 2 0 0 0 0 43 50 1 0 0 0 0 43 56 2 0 0 0 0 44 51 1 0 0 0 0 44 57 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	827.53
Volume:	874.33
LogP:	3.939
LogD:	2.817
LogS:	-4.286
# Rotatable Bonds:	26
TPSA:	134.75
# H-Bond Aceptor:	13
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.127
Synthetic Accessibility Score:	5.298
Fsp3:	0.75
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982
MDCK Permeability:	1.4059773093322292e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.586
Human Intestinal Absorption (HIA):	0.936
20% Bioavailability (F20%):	0.57
30% Bioavailability (F30%):	0.722

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	95.8964614868164%
Volume Distribution (VD):	1.019
Pgp-substrate:	2.058520793914795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.359
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.217
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.963
CYP3A4-substrate:	0.945

ADMET: Excretion

Clearance (CL):	6.367
Half-life (T1/2):	0.092

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.968
Drug-inuced Liver Injury (DILI):	0.995
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.284
Skin Sensitization:	0.051
Carcinogencity:	0.012
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.966

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC275393

Natural Product ID:	NPC275393
*Common Name:**	Apramide G
IUPAC Name:	(2R)-N,2-dimethyl-N-[(2S)-1-[methyl-[(2S)-3-methyl-1-[methyl-[(2S)-3-methyl-1-[methyl-[(2S)-3-methyl-1-[methyl-[(2S)-3-methyl-1-oxo-1-[(2S)-2-(1,3-thiazol-2-yl)pyrrolidin-1-yl]butan-2-yl]amino]-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]oct-7-ynamide
Synonyms:	Apramide G
Standard InCHIKey:	HAXFUPMEEWESKW-DGELVMTCSA-N
Standard InCHI:	InChI=1S/C44H73N7O6S/c1-17-18-19-20-22-31(10)39(52)46(12)32(11)40(53)47(13)34(27(2)3)41(54)48(14)35(28(4)5)42(55)49(15)36(29(6)7)43(56)50(16)37(30(8)9)44(57)51-25-21-23-33(51)38-45-24-26-58-38/h1,24,26-37H,18-23,25H2,2-16H3/t31-,32+,33+,34+,35+,36+,37+/m1/s1
SMILES:	C#CCCCC[C@@H](C)C(=O)N(C)[C@@H](C)C(=O)N(C)[C@@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N1CCC[C@H]1c1nccs1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501066
PubChem CID:	10843163
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004310] Valine and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10514329]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10654420]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10691708]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	palauan	n.a.	PMID[10691729]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10843570]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10924172]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10978206]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076571]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076573]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076574]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11277744]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11389621]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11430000]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473443]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11922791]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762816]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[12828459]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14575437]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1517734]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[16643028]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125217]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17441769]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18444683]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Singapore	n.a.	PMID[19093843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19489598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	eastern Caribbean	n.a.	PMID[19739598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19839606]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20030365]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	panamanian	n.a.	PMID[20158242]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Floridian	n.a.	PMID[20166701]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20936843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21138309]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2128518]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21341718]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21539315]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21806011]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21999614]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22035372]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29792428]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3924698]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[7623050]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[8699186]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9584405]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599278]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599279]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9784156]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	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	NP ID	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.033	ug.mL-1	PMID[535996]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	0.011	ug.mL-1	PMID[535996]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC275393 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	509
0.1-0.2	28599
0.2-0.3	10074
0.3-0.4	3061
0.4-0.5	405
0.5-0.6	36
0.6-0.7	9
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7786	Intermediate Similarity	NPC145047
0.7786	Intermediate Similarity	NPC86490
0.7388	Intermediate Similarity	NPC137705
0.6828	Remote Similarity	NPC478254
0.6828	Remote Similarity	NPC478253
0.6623	Remote Similarity	NPC478251
0.6623	Remote Similarity	NPC478252
0.6467	Remote Similarity	NPC103268
0.6441	Remote Similarity	NPC239660
0.6441	Remote Similarity	NPC106235
0.6433	Remote Similarity	NPC161143
0.6429	Remote Similarity	NPC475390
0.6387	Remote Similarity	NPC261708
0.6162	Remote Similarity	NPC75498
0.6129	Remote Similarity	NPC257511
0.6	Remote Similarity	NPC278902
0.5882	Remote Similarity	NPC475920
0.5687	Remote Similarity	NPC469801
0.5685	Remote Similarity	NPC214375
0.5635	Remote Similarity	NPC96016
0.5632	Remote Similarity	NPC164006

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC275393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	2163
0.2-0.3	4428
0.3-0.4	2132
0.4-0.5	236
0.5-0.6	12
0.6-0.7	1
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
0.6441	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD221	Approved
0.5743	Remote Similarity	NPD222	Approved
0.5705	Remote Similarity	NPD2225	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD6632	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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