NPASS Compound

Structure

NPC268744 OpenBabel07101719122D 26 30 0 0 1 0 0 0 0 0999 V2000 -4.2346 -2.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1006 -1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3686 -1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1006 -0.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6320 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7660 -2.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7660 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6389 -3.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0322 0.5862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6320 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3686 -0.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 -2.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6254 -0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2346 -0.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -1.6942 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 -4.4543 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.0267 0.4817 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 -4.2633 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 -1.4863 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 12 2 0 0 0 0 4 16 2 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 23 1 0 0 0 0 9 15 2 0 0 0 0 9 22 1 0 0 0 0 10 18 1 0 0 0 0 10 24 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 14 1 1 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 20 24 1 0 0 0 0 20 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.04
Volume:	357.39
LogP:	3.936
LogD:	3.752
LogS:	-2.962
# Rotatable Bonds:	2
TPSA:	73.04
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	3.755
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.204
MDCK Permeability:	9.378124559589196e-06
Pgp-inhibitor:	0.995
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.906

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.583
Plasma Protein Binding (PPB):	90.8592758178711%
Volume Distribution (VD):	1.603
Pgp-substrate:	11.23779296875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.653
CYP1A2-substrate:	0.417
CYP2C19-inhibitor:	0.906
CYP2C19-substrate:	0.302
CYP2C9-inhibitor:	0.687
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.712
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.966
CYP3A4-substrate:	0.63

ADMET: Excretion

Clearance (CL):	1.983
Half-life (T1/2):	0.407

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.777
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.749
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.072
Carcinogencity:	0.096
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC268744

Natural Product ID:	NPC268744
*Common Name:**	(R)-6'-Debromohamacanthin B
IUPAC Name:	(3R)-3-(6-bromo-1H-indol-3-yl)-5-(1H-indol-3-yl)-2,3-dihydro-1H-pyrazin-6-one
Synonyms:
Standard InCHIKey:	FGNFMNKARKPBGP-SFHVURJKSA-N
Standard InCHI:	InChI=1S/C20H15BrN4O/c21-11-5-6-13-14(8-23-17(13)7-11)18-10-24-20(26)19(25-18)15-9-22-16-4-2-1-3-12(15)16/h1-9,18,22-23H,10H2,(H,24,26)/t18-/m0/s1
SMILES:	Brc1ccc2c(c1)[nH]cc2[C@@H]1CNC(=O)C(=N1)c1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL371902
PubChem CID:	21778317
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921415]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16154746]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253840]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	southern australian	n.a.	PMID[9599272]

☑ 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
ED50	5
IC50	1
MIC	21

Activity Type	# Activity
Cell Line	5
Individual Protein	1
Organism	21

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	100.0	ug.mL-1	PMID[470971]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.71	ug ml-1	PMID[470972]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	8.5	ug ml-1	PMID[470972]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	7.6	ug ml-1	PMID[470972]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	8.3	ug ml-1	PMID[470972]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.2	ug ml-1	PMID[470972]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100.0	ug.mL-1	PMID[470971]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	25.0	ug.mL-1	PMID[470972]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	25.0	ug.mL-1	PMID[470972]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	25.0	ug.mL-1	PMID[470972]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	25.0	ug.mL-1	PMID[470972]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	25.0	ug.mL-1	PMID[470972]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>	25.0	ug.mL-1	PMID[470972]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	6.3	ug.mL-1	PMID[470972]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	12.5	ug.mL-1	PMID[470972]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[470972]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	25.0	ug.mL-1	PMID[470972]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[470972]
NPT4997	Organism	Klebsiella oxytoca	Klebsiella oxytoca	MIC	=	25.0	ug.mL-1	PMID[470972]

☑ 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 NPC268744 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	765
0.1-0.2	12431
0.2-0.3	19688
0.3-0.4	4378
0.4-0.5	2288
0.5-0.6	1668
0.6-0.7	1142
0.7-0.8	304
0.8-0.85	21
0.85-0.9	0
0.9-0.95	2
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474318
1.0	High Similarity	NPC220797
1.0	High Similarity	NPC201266
1.0	High Similarity	NPC153123
1.0	High Similarity	NPC475914
0.9944	High Similarity	NPC166209
0.9944	High Similarity	NPC13456
0.9944	High Similarity	NPC77241
0.9944	High Similarity	NPC269203
0.9209	High Similarity	NPC99939
0.9209	High Similarity	NPC308931
0.8571	High Similarity	NPC474389
0.8526	High Similarity	NPC477004
0.8492	Intermediate Similarity	NPC477611
0.8477	Intermediate Similarity	NPC470702
0.8477	Intermediate Similarity	NPC473218
0.8434	Intermediate Similarity	NPC470703
0.8385	Intermediate Similarity	NPC23420
0.8385	Intermediate Similarity	NPC205254
0.8385	Intermediate Similarity	NPC303820
0.8385	Intermediate Similarity	NPC106771
0.8342	Intermediate Similarity	NPC475935
0.8342	Intermediate Similarity	NPC94211
0.8342	Intermediate Similarity	NPC52909
0.8158	Intermediate Similarity	NPC476460
0.8105	Intermediate Similarity	NPC231536
0.8098	Intermediate Similarity	NPC474958
0.8095	Intermediate Similarity	NPC17059
0.8073	Intermediate Similarity	NPC188821
0.8073	Intermediate Similarity	NPC474180
0.8051	Intermediate Similarity	NPC237414
0.8032	Intermediate Similarity	NPC110158
0.8011	Intermediate Similarity	NPC274229
0.8011	Intermediate Similarity	NPC17751
0.8011	Intermediate Similarity	NPC11126
0.798	Intermediate Similarity	NPC317701
0.7979	Intermediate Similarity	NPC88315
0.7966	Intermediate Similarity	NPC141926
0.7937	Intermediate Similarity	NPC228835
0.7935	Intermediate Similarity	NPC82331
0.7887	Intermediate Similarity	NPC304203
0.7842	Intermediate Similarity	NPC477003
0.7831	Intermediate Similarity	NPC307191
0.7804	Intermediate Similarity	NPC63031
0.7796	Intermediate Similarity	NPC161861
0.7795	Intermediate Similarity	NPC326422
0.7789	Intermediate Similarity	NPC470205
0.7784	Intermediate Similarity	NPC288838
0.7772	Intermediate Similarity	NPC321708
0.7766	Intermediate Similarity	NPC284775
0.774	Intermediate Similarity	NPC475736
0.7727	Intermediate Similarity	NPC131887
0.7721	Intermediate Similarity	NPC935
0.7721	Intermediate Similarity	NPC267078
0.7708	Intermediate Similarity	NPC15102
0.7692	Intermediate Similarity	NPC92796
0.7692	Intermediate Similarity	NPC135141
0.7685	Intermediate Similarity	NPC474357
0.7684	Intermediate Similarity	NPC91179
0.7677	Intermediate Similarity	NPC227582
0.7676	Intermediate Similarity	NPC56233
0.7672	Intermediate Similarity	NPC59269
0.7668	Intermediate Similarity	NPC94752
0.7667	Intermediate Similarity	NPC474195
0.7663	Intermediate Similarity	NPC317105
0.766	Intermediate Similarity	NPC280297
0.7654	Intermediate Similarity	NPC53947
0.7653	Intermediate Similarity	NPC477166
0.7653	Intermediate Similarity	NPC477167
0.7653	Intermediate Similarity	NPC473342
0.7653	Intermediate Similarity	NPC304187
0.7632	Intermediate Similarity	NPC276540
0.7632	Intermediate Similarity	NPC233050
0.7622	Intermediate Similarity	NPC280864
0.7606	Intermediate Similarity	NPC474196
0.76	Intermediate Similarity	NPC74413
0.7594	Intermediate Similarity	NPC97343
0.7593	Intermediate Similarity	NPC470323
0.7588	Intermediate Similarity	NPC167710
0.7585	Intermediate Similarity	NPC207020
0.7574	Intermediate Similarity	NPC476073
0.7569	Intermediate Similarity	NPC325903
0.7568	Intermediate Similarity	NPC149265
0.7565	Intermediate Similarity	NPC108011
0.7562	Intermediate Similarity	NPC252338
0.7552	Intermediate Similarity	NPC275292
0.7552	Intermediate Similarity	NPC243381
0.755	Intermediate Similarity	NPC67288
0.7541	Intermediate Similarity	NPC216643
0.7527	Intermediate Similarity	NPC34844
0.7526	Intermediate Similarity	NPC133003
0.7524	Intermediate Similarity	NPC477715
0.7523	Intermediate Similarity	NPC201831
0.7523	Intermediate Similarity	NPC17487
0.7512	Intermediate Similarity	NPC54420
0.7511	Intermediate Similarity	NPC475746
0.75	Intermediate Similarity	NPC2272
0.75	Intermediate Similarity	NPC213629
0.7489	Intermediate Similarity	NPC477109
0.7489	Intermediate Similarity	NPC477107
0.7489	Intermediate Similarity	NPC477108
0.7488	Intermediate Similarity	NPC477714
0.7488	Intermediate Similarity	NPC260900
0.7487	Intermediate Similarity	NPC294693
0.7487	Intermediate Similarity	NPC478183
0.7474	Intermediate Similarity	NPC21429
0.7473	Intermediate Similarity	NPC21174
0.7473	Intermediate Similarity	NPC478184
0.7473	Intermediate Similarity	NPC271797
0.7473	Intermediate Similarity	NPC247987
0.7462	Intermediate Similarity	NPC324091
0.7452	Intermediate Similarity	NPC72956
0.745	Intermediate Similarity	NPC179701
0.744	Intermediate Similarity	NPC478158
0.744	Intermediate Similarity	NPC162860
0.7429	Intermediate Similarity	NPC478157
0.7419	Intermediate Similarity	NPC156003
0.7416	Intermediate Similarity	NPC471194
0.7416	Intermediate Similarity	NPC6865
0.7416	Intermediate Similarity	NPC153980
0.7416	Intermediate Similarity	NPC471193
0.7413	Intermediate Similarity	NPC262898
0.7409	Intermediate Similarity	NPC16659
0.7402	Intermediate Similarity	NPC473761
0.7398	Intermediate Similarity	NPC62749
0.7396	Intermediate Similarity	NPC240088
0.7396	Intermediate Similarity	NPC473380
0.7389	Intermediate Similarity	NPC316069
0.7385	Intermediate Similarity	NPC467063
0.7381	Intermediate Similarity	NPC477610
0.7379	Intermediate Similarity	NPC82053
0.7376	Intermediate Similarity	NPC171317
0.7373	Intermediate Similarity	NPC117980
0.7371	Intermediate Similarity	NPC191415
0.7366	Intermediate Similarity	NPC122141
0.7358	Intermediate Similarity	NPC265710
0.7354	Intermediate Similarity	NPC63751
0.7348	Intermediate Similarity	NPC469811
0.7344	Intermediate Similarity	NPC280852
0.734	Intermediate Similarity	NPC42372
0.7333	Intermediate Similarity	NPC102755
0.7333	Intermediate Similarity	NPC75634
0.7333	Intermediate Similarity	NPC470440
0.733	Intermediate Similarity	NPC105127
0.733	Intermediate Similarity	NPC473376
0.7318	Intermediate Similarity	NPC190296
0.7316	Intermediate Similarity	NPC471943
0.7312	Intermediate Similarity	NPC293487
0.7311	Intermediate Similarity	NPC471192
0.7308	Intermediate Similarity	NPC321911
0.7306	Intermediate Similarity	NPC111275
0.7293	Intermediate Similarity	NPC63545
0.7293	Intermediate Similarity	NPC143872
0.7292	Intermediate Similarity	NPC203468
0.7292	Intermediate Similarity	NPC110500
0.7292	Intermediate Similarity	NPC149155
0.7287	Intermediate Similarity	NPC478182
0.7283	Intermediate Similarity	NPC200214
0.7273	Intermediate Similarity	NPC96102
0.7268	Intermediate Similarity	NPC55772
0.7263	Intermediate Similarity	NPC78020
0.7255	Intermediate Similarity	NPC293917
0.7254	Intermediate Similarity	NPC267885
0.7253	Intermediate Similarity	NPC179787
0.7253	Intermediate Similarity	NPC201380
0.7247	Intermediate Similarity	NPC110126
0.7238	Intermediate Similarity	NPC314372
0.7238	Intermediate Similarity	NPC159856
0.7232	Intermediate Similarity	NPC84911
0.7231	Intermediate Similarity	NPC88110
0.723	Intermediate Similarity	NPC470732
0.723	Intermediate Similarity	NPC470731
0.7225	Intermediate Similarity	NPC194411
0.7222	Intermediate Similarity	NPC17273
0.7222	Intermediate Similarity	NPC141612
0.7222	Intermediate Similarity	NPC135601
0.7219	Intermediate Similarity	NPC206819
0.7219	Intermediate Similarity	NPC318065
0.7219	Intermediate Similarity	NPC475990
0.7216	Intermediate Similarity	NPC145885
0.7216	Intermediate Similarity	NPC14113
0.7216	Intermediate Similarity	NPC84827
0.7208	Intermediate Similarity	NPC165495
0.7207	Intermediate Similarity	NPC469783
0.7207	Intermediate Similarity	NPC469780
0.7207	Intermediate Similarity	NPC469767
0.7207	Intermediate Similarity	NPC469768
0.7207	Intermediate Similarity	NPC469784
0.7207	Intermediate Similarity	NPC469779
0.7207	Intermediate Similarity	NPC469761
0.7202	Intermediate Similarity	NPC293216
0.7202	Intermediate Similarity	NPC469529
0.7196	Intermediate Similarity	NPC477114
0.7189	Intermediate Similarity	NPC232798
0.7181	Intermediate Similarity	NPC279918
0.7179	Intermediate Similarity	NPC213468
0.7179	Intermediate Similarity	NPC126709
0.7179	Intermediate Similarity	NPC248041
0.7179	Intermediate Similarity	NPC283219
0.7175	Intermediate Similarity	NPC261195

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 NPC268744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	796
0.2-0.3	1203
0.3-0.4	2248
0.4-0.5	2215
0.5-0.6	1747
0.6-0.7	510
0.7-0.8	69
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
0.8063	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD7619	Phase 3
0.7846	Intermediate Similarity	NPD7618	Phase 3
0.7807	Intermediate Similarity	NPD4075	Phase 2
0.7668	Intermediate Similarity	NPD6217	Discontinued
0.7598	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6664	Approved
0.7586	Intermediate Similarity	NPD5426	Phase 3
0.7577	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD4922	Phase 2
0.7474	Intermediate Similarity	NPD7564	Discontinued
0.7474	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD3961	Discontinued
0.7427	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2880	Discontinued
0.7396	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2442	Approved
0.7391	Intermediate Similarity	NPD2443	Approved
0.7347	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3319	Phase 1
0.7333	Intermediate Similarity	NPD3318	Approved
0.7333	Intermediate Similarity	NPD3320	Approved
0.732	Intermediate Similarity	NPD6595	Phase 3
0.7292	Intermediate Similarity	NPD482	Approved
0.7292	Intermediate Similarity	NPD4128	Approved
0.7286	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4848	Phase 1
0.7273	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD786	Approved
0.7246	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7666	Phase 3
0.7225	Intermediate Similarity	NPD6459	Phase 2
0.7225	Intermediate Similarity	NPD7665	Phase 2
0.7213	Intermediate Similarity	NPD3100	Discontinued
0.7212	Intermediate Similarity	NPD2008	Discontinued
0.7208	Intermediate Similarity	NPD2091	Phase 2
0.7208	Intermediate Similarity	NPD2096	Phase 2
0.7196	Intermediate Similarity	NPD3583	Phase 2
0.719	Intermediate Similarity	NPD2408	Discontinued
0.7189	Intermediate Similarity	NPD2837	Discontinued
0.7186	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2172	Phase 1
0.7171	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6999	Discontinued
0.717	Intermediate Similarity	NPD8093	Discontinued
0.717	Intermediate Similarity	NPD2411	Approved
0.7167	Intermediate Similarity	NPD1722	Approved
0.7165	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD2095	Phase 2
0.7157	Intermediate Similarity	NPD2094	Phase 2
0.7157	Intermediate Similarity	NPD2092	Phase 2
0.7156	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7470	Discontinued
0.7113	Intermediate Similarity	NPD5065	Approved
0.71	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5901	Discontinued
0.7059	Intermediate Similarity	NPD7944	Discontinued
0.7056	Intermediate Similarity	NPD5473	Discontinued
0.7056	Intermediate Similarity	NPD8094	Discontinued
0.7054	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5400	Approved
0.7053	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6771	Discontinued
0.705	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3505	Approved
0.7041	Intermediate Similarity	NPD3506	Approved
0.7041	Intermediate Similarity	NPD4181	Approved
0.7033	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7781	Approved
0.7027	Intermediate Similarity	NPD7780	Approved
0.7023	Intermediate Similarity	NPD7970	Approved
0.7023	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1895	Discontinued
0.7016	Intermediate Similarity	NPD3323	Discontinued
0.7005	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4076	Approved
0.7005	Intermediate Similarity	NPD4079	Approved
0.6995	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6165	Phase 2
0.6982	Remote Similarity	NPD6164	Phase 2
0.698	Remote Similarity	NPD7175	Phase 1
0.6974	Remote Similarity	NPD750	Phase 2
0.6972	Remote Similarity	NPD5199	Approved
0.6972	Remote Similarity	NPD5198	Approved
0.6961	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD200	Phase 2
0.6944	Remote Similarity	NPD201	Phase 2
0.6942	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD2290	Phase 3
0.6942	Remote Similarity	NPD2289	Phase 3
0.6938	Remote Similarity	NPD5017	Discontinued
0.6938	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7603	Discontinued
0.6923	Remote Similarity	NPD7716	Approved
0.6923	Remote Similarity	NPD7717	Approved
0.6907	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.689	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7001	Phase 3
0.6884	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2479	Phase 3
0.6884	Remote Similarity	NPD2481	Approved
0.6881	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1982	Phase 1
0.6872	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD2069	Approved
0.6868	Remote Similarity	NPD2071	Approved
0.6868	Remote Similarity	NPD2070	Approved
0.6868	Remote Similarity	NPD2068	Approved
0.686	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD2639	Approved
0.6856	Remote Similarity	NPD2642	Approved
0.6849	Remote Similarity	NPD6470	Phase 3
0.6847	Remote Similarity	NPD8431	Approved
0.6834	Remote Similarity	NPD3076	Approved
0.6834	Remote Similarity	NPD3077	Approved
0.6834	Remote Similarity	NPD3079	Approved
0.6834	Remote Similarity	NPD3078	Approved
0.6832	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5446	Phase 2
0.6825	Remote Similarity	NPD2881	Approved
0.6825	Remote Similarity	NPD2879	Approved
0.6822	Remote Similarity	NPD2510	Approved
0.6822	Remote Similarity	NPD5421	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD2509	Approved
0.6821	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6044	Discontinued
0.6816	Remote Similarity	NPD5105	Approved
0.6816	Remote Similarity	NPD5106	Approved
0.6809	Remote Similarity	NPD4463	Approved
0.6809	Remote Similarity	NPD4462	Approved
0.6808	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4863	Approved
0.6798	Remote Similarity	NPD7026	Phase 2
0.6794	Remote Similarity	NPD4364	Phase 1
0.6782	Remote Similarity	NPD6178	Phase 3
0.678	Remote Similarity	NPD4499	Approved
0.6779	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1506	Discontinued
0.6776	Remote Similarity	NPD8322	Phase 2
0.6776	Remote Similarity	NPD3905	Phase 3
0.6774	Remote Similarity	NPD4852	Phase 2
0.6769	Remote Similarity	NPD6986	Phase 1
0.6768	Remote Similarity	NPD4883	Approved
0.6763	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD8272	Phase 2
0.6759	Remote Similarity	NPD4051	Discontinued
0.6759	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1183	Approved
0.6754	Remote Similarity	NPD7791	Approved
0.6754	Remote Similarity	NPD7790	Approved
0.6754	Remote Similarity	NPD7952	Approved
0.6754	Remote Similarity	NPD7951	Approved
0.6754	Remote Similarity	NPD7789	Approved
0.6754	Remote Similarity	NPD7953	Approved
0.6754	Remote Similarity	NPD7950	Approved
0.6751	Remote Similarity	NPD3610	Approved
0.6751	Remote Similarity	NPD3609	Approved
0.6743	Remote Similarity	NPD6787	Phase 2
0.6739	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5818	Discontinued
0.6727	Remote Similarity	NPD8256	Approved
0.6727	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7185	Discontinued
0.6727	Remote Similarity	NPD8257	Approved
0.6716	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3431	Approved
0.6715	Remote Similarity	NPD3430	Approved
0.6702	Remote Similarity	NPD4547	Phase 3
0.67	Remote Similarity	NPD2144	Approved
0.6699	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7657	Approved
0.6697	Remote Similarity	NPD7656	Approved
0.6697	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7394	Phase 2
0.6682	Remote Similarity	NPD7209	Approved
0.6682	Remote Similarity	NPD7207	Approved
0.6682	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7208	Approved
0.6681	Remote Similarity	NPD7731	Approved
0.6681	Remote Similarity	NPD7730	Approved

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