NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	257.12
Volume:	259.783
LogP:	2.409
LogD:	2.051
LogS:	-3.002
# Rotatable Bonds:	2
TPSA:	77.31
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.659
Synthetic Accessibility Score:	3.731
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.727
MDCK Permeability:	1.0168256267206743e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.083
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.471
Plasma Protein Binding (PPB):	93.7322769165039%
Volume Distribution (VD):	1.051
Pgp-substrate:	13.92379379272461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.227
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.429
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.165
CYP2D6-substrate:	0.188
CYP3A4-inhibitor:	0.678
CYP3A4-substrate:	0.567

ADMET: Excretion

Clearance (CL):	3.807
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.257
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.825
Carcinogencity:	0.439
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC163421

Natural Product ID:	NPC163421
*Common Name:**	Indomycin
IUPAC Name:	(5S)-5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-(methylamino)-1,3-oxazol-4-one
Synonyms:	Indomycin
Standard InCHIKey:	GNTVWGDQPXCYBV-PELKAZGASA-N
Standard InCHI:	InChI=1S/C14H15N3O2/c1-8(12-13(18)17-14(15-2)19-12)10-7-16-11-6-4-3-5-9(10)11/h3-8,12,16H,1-2H3,(H,15,17,18)/t8-,12+/m1/s1
SMILES:	CN=C1N=C([C@@H](O1)[C@@H](c1c[nH]c2c1cccc2)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL417852
PubChem CID:	210263
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
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11551769]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1593278]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18232659]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21693706]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21939253]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22101040]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25730866]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[5447649]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[809439]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[TCMID]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	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	3
MIC	28
Others	20

Activity Type	# Activity
NON-MOLECULAR	1
Organism	46
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.125	ug.mL-1	PMID[524785]
NPT2	Others	Unspecified		IC50	=	0.016	ug.mL-1	PMID[524785]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	FC	=	60.0	n.a.	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	MIC	>	150.0	ug.mL-1	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	MIC	=	0.25	ug.mL-1	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	MIC	=	10.0	ug.mL-1	PMID[524786]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	5.0	ug.mL-1	PMID[524786]
NPT4890	Organism	Streptomyces griseus	Streptomyces griseus	MIC	=	15.0	ug.mL-1	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	MIC	=	5.0	ug.mL-1	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	MIC	>	75.0	ug.mL-1	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	MIC	=	3.0	ug.mL-1	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	MIC	=	8.0	ug.mL-1	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	MIC	=	2.0	ug.mL-1	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	MIC	=	12.0	ug.mL-1	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	FC	=	1.0	n.a.	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	FC	=	20.0	n.a.	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	FC	>	300.0	n.a.	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	FC	=	12.0	n.a.	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	FC	=	32.0	n.a.	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	FC	=	8.0	n.a.	PMID[524786]
NPT2908	Organism	Streptomyces coelicolor	Streptomyces coelicolor	FC	=	48.0	n.a.	PMID[524786]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC90	=	5000.0	nM	PMID[524787]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	20.0	ug.mL-1	PMID[524788]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[524788]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	2.0	ug.mL-1	PMID[524788]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	200.0	ug.mL-1	PMID[524788]
NPT742	Organism	Influenza A virus	Influenza A virus	PDD50	>	100.0	ug ml-1	PMID[524788]
NPT27	Others	Unspecified		MCC	>	100.0	ug.mL-1	PMID[524788]
NPT742	Organism	Influenza A virus	Influenza A virus	IZ	=	0.0	mm	PMID[524788]
NPT1833	Organism	Human coxsackievirus B1	Human coxsackievirus B1	IZ	=	0.0	mm	PMID[524788]
NPT2	Others	Unspecified		IC50	=	4040000.0	nM	PMID[524789]
NPT2	Others	Unspecified		IC50	=	9.25	nM	PMID[524789]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	0.016	ug.mL-1	PMID[524790]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.5	ug.mL-1	PMID[524790]

☑ 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 NPC163421 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	334
0.1-0.2	2722
0.2-0.3	15616
0.3-0.4	16171
0.4-0.5	3551
0.5-0.6	2259
0.6-0.7	1509
0.7-0.8	477
0.8-0.85	53
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188387
0.8788	High Similarity	NPC230869
0.8743	High Similarity	NPC311276
0.8736	High Similarity	NPC469358
0.8521	High Similarity	NPC40779
0.8483	Intermediate Similarity	NPC315555
0.8462	Intermediate Similarity	NPC282231
0.8421	Intermediate Similarity	NPC49954
0.8421	Intermediate Similarity	NPC54988
0.8421	Intermediate Similarity	NPC160105
0.8421	Intermediate Similarity	NPC474561
0.8402	Intermediate Similarity	NPC279918
0.8393	Intermediate Similarity	NPC469762
0.8333	Intermediate Similarity	NPC469785
0.8324	Intermediate Similarity	NPC470499
0.8323	Intermediate Similarity	NPC469763
0.8323	Intermediate Similarity	NPC259644
0.8323	Intermediate Similarity	NPC73952
0.8323	Intermediate Similarity	NPC469786
0.8323	Intermediate Similarity	NPC469760
0.8323	Intermediate Similarity	NPC25008
0.8323	Intermediate Similarity	NPC469765
0.8304	Intermediate Similarity	NPC102423
0.8294	Intermediate Similarity	NPC131718
0.8276	Intermediate Similarity	NPC470498
0.8274	Intermediate Similarity	NPC212376
0.8274	Intermediate Similarity	NPC211572
0.8274	Intermediate Similarity	NPC75540
0.8274	Intermediate Similarity	NPC80597
0.8274	Intermediate Similarity	NPC70922
0.8258	Intermediate Similarity	NPC71037
0.8249	Intermediate Similarity	NPC141377
0.8242	Intermediate Similarity	NPC95783
0.8229	Intermediate Similarity	NPC314603
0.8192	Intermediate Similarity	NPC151939
0.8182	Intermediate Similarity	NPC314372
0.8171	Intermediate Similarity	NPC190296
0.8161	Intermediate Similarity	NPC201700
0.8161	Intermediate Similarity	NPC63751
0.8156	Intermediate Similarity	NPC233936
0.8138	Intermediate Similarity	NPC470497
0.8125	Intermediate Similarity	NPC313791
0.8122	Intermediate Similarity	NPC314002
0.8122	Intermediate Similarity	NPC62510
0.8108	Intermediate Similarity	NPC267343
0.8092	Intermediate Similarity	NPC194640
0.809	Intermediate Similarity	NPC111275
0.8066	Intermediate Similarity	NPC204717
0.8057	Intermediate Similarity	NPC78020
0.8034	Intermediate Similarity	NPC267885
0.8033	Intermediate Similarity	NPC46580
0.8031	Intermediate Similarity	NPC314957
0.8021	Intermediate Similarity	NPC251090
0.8011	Intermediate Similarity	NPC220765
0.8011	Intermediate Similarity	NPC163055
0.8	Intermediate Similarity	NPC49217
0.8	Intermediate Similarity	NPC300688
0.7989	Intermediate Similarity	NPC59269
0.7989	Intermediate Similarity	NPC248454
0.7978	Intermediate Similarity	NPC110500
0.7978	Intermediate Similarity	NPC171171
0.7978	Intermediate Similarity	NPC149155
0.7978	Intermediate Similarity	NPC203468
0.7964	Intermediate Similarity	NPC159856
0.7946	Intermediate Similarity	NPC154339
0.7944	Intermediate Similarity	NPC126709
0.7944	Intermediate Similarity	NPC248041
0.7935	Intermediate Similarity	NPC317030
0.7923	Intermediate Similarity	NPC15102
0.7914	Intermediate Similarity	NPC307963
0.7912	Intermediate Similarity	NPC472444
0.7884	Intermediate Similarity	NPC77555
0.7882	Intermediate Similarity	NPC24678
0.7882	Intermediate Similarity	NPC105818
0.788	Intermediate Similarity	NPC474707
0.788	Intermediate Similarity	NPC235684
0.7877	Intermediate Similarity	NPC472586
0.787	Intermediate Similarity	NPC471957
0.7866	Intermediate Similarity	NPC84911
0.7865	Intermediate Similarity	NPC193761
0.7853	Intermediate Similarity	NPC317430
0.7846	Intermediate Similarity	NPC127677
0.7845	Intermediate Similarity	NPC472443
0.7845	Intermediate Similarity	NPC283219
0.7845	Intermediate Similarity	NPC55772
0.7838	Intermediate Similarity	NPC204565
0.7819	Intermediate Similarity	NPC474177
0.7814	Intermediate Similarity	NPC48938
0.7805	Intermediate Similarity	NPC261195
0.7805	Intermediate Similarity	NPC96102
0.7805	Intermediate Similarity	NPC29886
0.7803	Intermediate Similarity	NPC285469
0.7796	Intermediate Similarity	NPC296527
0.7796	Intermediate Similarity	NPC65215
0.7796	Intermediate Similarity	NPC173028
0.7796	Intermediate Similarity	NPC213629
0.7795	Intermediate Similarity	NPC46225
0.779	Intermediate Similarity	NPC184964
0.7778	Intermediate Similarity	NPC151976
0.7772	Intermediate Similarity	NPC476073
0.7771	Intermediate Similarity	NPC110126
0.7771	Intermediate Similarity	NPC73767
0.7766	Intermediate Similarity	NPC99666
0.776	Intermediate Similarity	NPC314394
0.7758	Intermediate Similarity	NPC105127
0.7754	Intermediate Similarity	NPC76748
0.775	Intermediate Similarity	NPC204491
0.7749	Intermediate Similarity	NPC131887
0.7747	Intermediate Similarity	NPC213468
0.7737	Intermediate Similarity	NPC242209
0.7737	Intermediate Similarity	NPC11445
0.7732	Intermediate Similarity	NPC98715
0.7725	Intermediate Similarity	NPC469780
0.7725	Intermediate Similarity	NPC469767
0.7725	Intermediate Similarity	NPC469784
0.7725	Intermediate Similarity	NPC469768
0.7725	Intermediate Similarity	NPC469783
0.7725	Intermediate Similarity	NPC469779
0.7725	Intermediate Similarity	NPC469761
0.772	Intermediate Similarity	NPC475506
0.772	Intermediate Similarity	NPC300183
0.7717	Intermediate Similarity	NPC472108
0.7717	Intermediate Similarity	NPC139291
0.7717	Intermediate Similarity	NPC19679
0.7713	Intermediate Similarity	NPC92111
0.7708	Intermediate Similarity	NPC100321
0.7704	Intermediate Similarity	NPC88008
0.7701	Intermediate Similarity	NPC141353
0.7692	Intermediate Similarity	NPC68354
0.7692	Intermediate Similarity	NPC84827
0.7692	Intermediate Similarity	NPC14113
0.7692	Intermediate Similarity	NPC145885
0.7684	Intermediate Similarity	NPC133366
0.7684	Intermediate Similarity	NPC195239
0.7684	Intermediate Similarity	NPC157828
0.768	Intermediate Similarity	NPC275305
0.768	Intermediate Similarity	NPC329688
0.768	Intermediate Similarity	NPC37423
0.768	Intermediate Similarity	NPC476874
0.768	Intermediate Similarity	NPC155143
0.768	Intermediate Similarity	NPC189812
0.7679	Intermediate Similarity	NPC469766
0.7676	Intermediate Similarity	NPC284678
0.7665	Intermediate Similarity	NPC258062
0.7657	Intermediate Similarity	NPC212742
0.7656	Intermediate Similarity	NPC473640
0.765	Intermediate Similarity	NPC270009
0.7638	Intermediate Similarity	NPC320968
0.7634	Intermediate Similarity	NPC280290
0.7632	Intermediate Similarity	NPC106937
0.763	Intermediate Similarity	NPC216713
0.7627	Intermediate Similarity	NPC16667
0.7626	Intermediate Similarity	NPC271862
0.7624	Intermediate Similarity	NPC472123
0.7624	Intermediate Similarity	NPC477114
0.7624	Intermediate Similarity	NPC34508
0.7622	Intermediate Similarity	NPC472109
0.7622	Intermediate Similarity	NPC472110
0.7619	Intermediate Similarity	NPC279081
0.7614	Intermediate Similarity	NPC92796
0.7614	Intermediate Similarity	NPC225821
0.7614	Intermediate Similarity	NPC135141
0.7611	Intermediate Similarity	NPC194411
0.7606	Intermediate Similarity	NPC32771
0.7606	Intermediate Similarity	NPC321708
0.7604	Intermediate Similarity	NPC227582
0.7604	Intermediate Similarity	NPC156704
0.7602	Intermediate Similarity	NPC143872
0.76	Intermediate Similarity	NPC316981
0.76	Intermediate Similarity	NPC87856
0.7596	Intermediate Similarity	NPC96890
0.7594	Intermediate Similarity	NPC62749
0.7592	Intermediate Similarity	NPC326634
0.7579	Intermediate Similarity	NPC473342
0.7579	Intermediate Similarity	NPC477167
0.7574	Intermediate Similarity	NPC132211
0.7574	Intermediate Similarity	NPC203614
0.7572	Intermediate Similarity	NPC53947
0.7562	Intermediate Similarity	NPC54744
0.7562	Intermediate Similarity	NPC266931
0.7562	Intermediate Similarity	NPC267965
0.7561	Intermediate Similarity	NPC82295
0.7557	Intermediate Similarity	NPC129721
0.7552	Intermediate Similarity	NPC13880
0.7543	Intermediate Similarity	NPC471458
0.7543	Intermediate Similarity	NPC207726
0.7539	Intermediate Similarity	NPC88315
0.7537	Intermediate Similarity	NPC472285
0.7526	Intermediate Similarity	NPC293917
0.7525	Intermediate Similarity	NPC313640
0.7515	Intermediate Similarity	NPC230002
0.7513	Intermediate Similarity	NPC46413
0.75	Intermediate Similarity	NPC288838
0.75	Intermediate Similarity	NPC94752
0.75	Intermediate Similarity	NPC5145
0.7488	Intermediate Similarity	NPC89987
0.7487	Intermediate Similarity	NPC213308
0.7487	Intermediate Similarity	NPC472294
0.7487	Intermediate Similarity	NPC315491
0.7487	Intermediate Similarity	NPC45459

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 NPC163421 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	593
0.2-0.3	935
0.3-0.4	1529
0.4-0.5	2828
0.5-0.6	2115
0.6-0.7	838
0.7-0.8	124
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8324	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD6595	Phase 3
0.8192	Intermediate Similarity	NPD2144	Approved
0.8156	Intermediate Similarity	NPD3038	Discontinued
0.8034	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD482	Approved
0.7914	Intermediate Similarity	NPD1038	Approved
0.7814	Intermediate Similarity	NPD2094	Phase 2
0.7814	Intermediate Similarity	NPD2095	Phase 2
0.7814	Intermediate Similarity	NPD2092	Phase 2
0.7805	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD1592	Phase 3
0.7778	Intermediate Similarity	NPD5065	Approved
0.7772	Intermediate Similarity	NPD2091	Phase 2
0.7772	Intermediate Similarity	NPD2096	Phase 2
0.7771	Intermediate Similarity	NPD786	Approved
0.7747	Intermediate Similarity	NPD4076	Approved
0.7747	Intermediate Similarity	NPD4079	Approved
0.773	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD750	Phase 2
0.7709	Intermediate Similarity	NPD1326	Approved
0.7709	Intermediate Similarity	NPD1325	Approved
0.7704	Intermediate Similarity	NPD1392	Approved
0.7701	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3505	Approved
0.7692	Intermediate Similarity	NPD5426	Phase 3
0.7692	Intermediate Similarity	NPD3506	Approved
0.7679	Intermediate Similarity	NPD1722	Approved
0.7647	Intermediate Similarity	NPD8431	Approved
0.7632	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD802	Phase 2
0.7632	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5612	Discontinued
0.7563	Intermediate Similarity	NPD7957	Phase 1
0.7563	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7470	Discontinued
0.7526	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7948	Phase 1
0.7487	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD484	Approved
0.7486	Intermediate Similarity	NPD5138	Approved
0.7486	Intermediate Similarity	NPD5140	Approved
0.7475	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2172	Phase 1
0.7462	Intermediate Similarity	NPD8072	Approved
0.7459	Intermediate Similarity	NPD2844	Phase 3
0.7433	Intermediate Similarity	NPD5596	Phase 2
0.7419	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3100	Discontinued
0.7405	Intermediate Similarity	NPD4181	Approved
0.7391	Intermediate Similarity	NPD4128	Approved
0.7387	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5067	Phase 2
0.7376	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5066	Phase 2
0.7368	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD8386	Phase 2
0.7356	Intermediate Similarity	NPD4703	Approved
0.7356	Intermediate Similarity	NPD4702	Approved
0.7351	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1768	Approved
0.7337	Intermediate Similarity	NPD8272	Phase 2
0.7327	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD8073	Approved
0.7323	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD2189	Approved
0.7313	Intermediate Similarity	NPD2187	Approved
0.7304	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD3003	Approved
0.73	Intermediate Similarity	NPD7001	Phase 3
0.7278	Intermediate Similarity	NPD1404	Approved
0.7278	Intermediate Similarity	NPD1403	Approved
0.7277	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4463	Approved
0.7273	Intermediate Similarity	NPD4462	Approved
0.7268	Intermediate Similarity	NPD4638	Approved
0.7268	Intermediate Similarity	NPD4640	Approved
0.7268	Intermediate Similarity	NPD4639	Approved
0.7255	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5901	Discontinued
0.7238	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD4427	Phase 2
0.7228	Intermediate Similarity	NPD2510	Approved
0.7228	Intermediate Similarity	NPD2509	Approved
0.7222	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3404	Approved
0.7213	Intermediate Similarity	NPD2639	Approved
0.7213	Intermediate Similarity	NPD2642	Approved
0.7209	Intermediate Similarity	NPD7558	Phase 2
0.7204	Intermediate Similarity	NPD2928	Phase 2
0.7198	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2640	Approved
0.7174	Intermediate Similarity	NPD2641	Approved
0.7172	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3825	Phase 3
0.7172	Intermediate Similarity	NPD6999	Discontinued
0.7165	Intermediate Similarity	NPD5913	Phase 3
0.7165	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5003	Discontinued
0.7136	Intermediate Similarity	NPD6165	Phase 2
0.7136	Intermediate Similarity	NPD4601	Approved
0.7136	Intermediate Similarity	NPD4600	Approved
0.7136	Intermediate Similarity	NPD6164	Phase 2
0.7135	Intermediate Similarity	NPD706	Phase 1
0.7126	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3717	Discontinued
0.7113	Intermediate Similarity	NPD5117	Phase 2
0.7111	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD3323	Discontinued
0.7098	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2837	Discontinued
0.709	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4075	Phase 2
0.7074	Intermediate Similarity	NPD2381	Approved
0.7074	Intermediate Similarity	NPD2380	Approved
0.7074	Intermediate Similarity	NPD5100	Phase 3
0.7074	Intermediate Similarity	NPD2382	Approved
0.7073	Intermediate Similarity	NPD8321	Discontinued
0.7067	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7944	Discontinued
0.7048	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5255	Approved
0.703	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD4499	Approved
0.7026	Intermediate Similarity	NPD6281	Approved
0.7024	Intermediate Similarity	NPD6545	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5902	Approved
0.7019	Intermediate Similarity	NPD5903	Approved
0.7016	Intermediate Similarity	NPD8408	Discontinued
0.701	Intermediate Similarity	NPD3961	Discontinued
0.701	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3330	Phase 1
0.7	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6555	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3013	Phase 3
0.6989	Remote Similarity	NPD5862	Discovery
0.6986	Remote Similarity	NPD3394	Approved
0.6986	Remote Similarity	NPD3393	Approved
0.6986	Remote Similarity	NPD3389	Approved
0.6985	Remote Similarity	NPD6664	Approved
0.6983	Remote Similarity	NPD3833	Phase 3
0.6983	Remote Similarity	NPD3835	Phase 3
0.698	Remote Similarity	NPD5486	Discontinued
0.6978	Remote Similarity	NPD2582	Approved
0.6978	Remote Similarity	NPD2581	Approved
0.6973	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8094	Discontinued
0.6966	Remote Similarity	NPD1661	Suspended
0.6963	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7271	Approved
0.6957	Remote Similarity	NPD8026	Phase 1
0.6957	Remote Similarity	NPD949	Phase 1
0.6954	Remote Similarity	NPD4615	Phase 2
0.695	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2565	Phase 2
0.6939	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2564	Approved
0.6939	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1248	Discontinued
0.6931	Remote Similarity	NPD4511	Phase 1
0.6931	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD1707	Approved
0.6927	Remote Similarity	NPD1708	Approved
0.6919	Remote Similarity	NPD8129	Discovery
0.6915	Remote Similarity	NPD3814	Phase 1
0.6915	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD3610	Approved
0.6915	Remote Similarity	NPD3609	Approved
0.6914	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4699	Discontinued
0.6902	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7730	Approved
0.6898	Remote Similarity	NPD7731	Approved
0.6898	Remote Similarity	NPD5021	Discontinued
0.6898	Remote Similarity	NPD6978	Phase 2
0.6898	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4670	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