NPASS Compound

Structure

NPC98892 OpenBabel07101719522D 50 53 0 0 0 0 0 0 0 0999 V2000 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 43 1 0 0 0 0 4 44 1 0 0 0 0 5 45 1 0 0 0 0 6 46 1 0 0 0 0 7 47 1 0 0 0 0 8 16 2 0 0 0 0 8 22 1 0 0 0 0 9 17 2 0 0 0 0 9 23 1 0 0 0 0 10 16 1 0 0 0 0 10 24 2 0 0 0 0 11 17 1 0 0 0 0 11 25 2 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 26 2 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 19 1 0 0 0 0 15 27 2 0 0 0 0 18 36 1 0 0 0 0 19 48 1 0 0 0 0 20 30 2 0 0 0 0 20 32 1 0 0 0 0 21 31 2 0 0 0 0 21 33 1 0 0 0 0 22 28 2 0 0 0 0 22 37 1 0 0 0 0 23 29 2 0 0 0 0 23 38 1 0 0 0 0 24 28 1 0 0 0 0 24 49 1 0 0 0 0 25 29 1 0 0 0 0 25 50 1 0 0 0 0 26 30 1 0 0 0 0 26 43 1 0 0 0 0 27 31 1 0 0 0 0 27 44 1 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 30 50 1 0 0 0 0 31 49 1 0 0 0 0 32 39 2 0 0 0 0 32 45 1 0 0 0 0 33 40 2 0 0 0 0 33 46 1 0 0 0 0 34 41 2 0 0 0 0 34 47 1 0 0 0 0 35 42 2 0 0 0 0 35 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	692.17
Volume:	669.36
LogP:	5.762
LogD:	3.541
LogS:	-5.768
# Rotatable Bonds:	15
TPSA:	202.81
# H-Bond Aceptor:	15
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.099
Synthetic Accessibility Score:	3.195
Fsp3:	0.2
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:	-5.85
MDCK Permeability:	4.8632955440552905e-05
Pgp-inhibitor:	0.843
Pgp-substrate:	0.346
Human Intestinal Absorption (HIA):	0.897
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.649

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	97.19416046142578%
Volume Distribution (VD):	0.375
Pgp-substrate:	14.266429901123047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.32
CYP1A2-substrate:	0.901
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.784
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.425
CYP3A4-inhibitor:	0.504
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	10.199
Half-life (T1/2):	0.635

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.005
Drug-inuced Liver Injury (DILI):	0.515
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.528
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.703
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.814
Respiratory Toxicity:	0.183

Download Data

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

Natural Product: NPC98892

Natural Product ID:	NPC98892
*Common Name:**	Geomycin A
IUPAC Name:	[4-(3-hydroxy-2-methoxycarbonyl-5-methylphenoxy)-3-methoxy-5-methoxycarbonylphenyl] 2-hydroxy-6-(4-hydroxy-2-methoxy-6-methoxycarbonylphenoxy)-4-methylbenzoate
Synonyms:
Standard InCHIKey:	IVXIKZPNFFNFSO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C35H32O15/c1-16-8-22(37)28(34(41)47-7)24(10-16)49-31-21(33(40)46-6)14-19(15-27(31)44-4)48-35(42)29-23(38)9-17(2)11-25(29)50-30-20(32(39)45-5)12-18(36)13-26(30)43-3/h8-15,36-38H,1-7H3
SMILES:	COC(=O)c1cc(cc(c1Oc1cc(C)cc(c1C(=O)OC)O)OC)OC(=O)c1c(O)cc(cc1Oc1c(OC)cc(cc1C(=O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501396
PubChem CID:	25111484
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO32625	geomyces sp.	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18720971]

☑ 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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IC50	>	50000.0	nM	PMID[544188]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	50000.0	nM	PMID[544188]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	IC50	>	50000.0	nM	PMID[544188]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>	50000.0	nM	PMID[544188]

☑ 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 NPC98892 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	380
0.1-0.2	1784
0.2-0.3	4976
0.3-0.4	10807
0.4-0.5	6948
0.5-0.6	3926
0.6-0.7	5636
0.7-0.8	6770
0.8-0.85	1353
0.85-0.9	105
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC287458
0.9404	High Similarity	NPC285527
0.9404	High Similarity	NPC106334
0.9342	High Similarity	NPC213382
0.9342	High Similarity	NPC164527
0.9136	High Similarity	NPC72696
0.9114	High Similarity	NPC188967
0.9074	High Similarity	NPC476279
0.9051	High Similarity	NPC190487
0.9051	High Similarity	NPC154304
0.8968	High Similarity	NPC225129
0.8882	High Similarity	NPC476200
0.8882	High Similarity	NPC192258
0.8848	High Similarity	NPC476370
0.8841	High Similarity	NPC49487
0.8841	High Similarity	NPC280493
0.8841	High Similarity	NPC99613
0.8795	High Similarity	NPC476374
0.8788	High Similarity	NPC19273
0.8788	High Similarity	NPC476365
0.8788	High Similarity	NPC17884
0.8773	High Similarity	NPC280893
0.8765	High Similarity	NPC476371
0.8765	High Similarity	NPC476372
0.8765	High Similarity	NPC174311
0.875	High Similarity	NPC185526
0.8735	High Similarity	NPC158226
0.8734	High Similarity	NPC75069
0.8734	High Similarity	NPC289968
0.872	High Similarity	NPC29160
0.8712	High Similarity	NPC272064
0.8675	High Similarity	NPC124470
0.8675	High Similarity	NPC109827
0.8667	High Similarity	NPC234331
0.8659	High Similarity	NPC142614
0.8655	High Similarity	NPC154527
0.8654	High Similarity	NPC46941
0.865	High Similarity	NPC55121
0.8647	High Similarity	NPC117668
0.8642	High Similarity	NPC476373
0.8642	High Similarity	NPC130955
0.8639	High Similarity	NPC297807
0.8634	High Similarity	NPC183
0.8625	High Similarity	NPC125709
0.8625	High Similarity	NPC292385
0.8625	High Similarity	NPC208197
0.8614	High Similarity	NPC163130
0.8614	High Similarity	NPC165979
0.8605	High Similarity	NPC226725
0.8598	High Similarity	NPC300984
0.8598	High Similarity	NPC474350
0.8589	High Similarity	NPC196179
0.8589	High Similarity	NPC34089
0.8589	High Similarity	NPC217950
0.858	High Similarity	NPC36354
0.858	High Similarity	NPC87317
0.858	High Similarity	NPC216307
0.8571	High Similarity	NPC54928
0.8562	High Similarity	NPC75279
0.8562	High Similarity	NPC280937
0.8562	High Similarity	NPC250822
0.8562	High Similarity	NPC472915
0.8562	High Similarity	NPC276409
0.8554	High Similarity	NPC76647
0.8553	High Similarity	NPC208043
0.8553	High Similarity	NPC226973
0.8553	High Similarity	NPC474663
0.8553	High Similarity	NPC308451
0.8545	High Similarity	NPC267153
0.8544	High Similarity	NPC200221
0.8544	High Similarity	NPC294502
0.8544	High Similarity	NPC328119
0.8538	High Similarity	NPC47883
0.8537	High Similarity	NPC108767
0.8529	High Similarity	NPC98546
0.8528	High Similarity	NPC53889
0.8521	High Similarity	NPC99591
0.8519	High Similarity	NPC36077
0.8512	High Similarity	NPC475669
0.8512	High Similarity	NPC174700
0.8509	High Similarity	NPC4455
0.8509	High Similarity	NPC20830
0.8509	High Similarity	NPC128863
0.8509	High Similarity	NPC183597
0.8509	High Similarity	NPC50715
0.8509	High Similarity	NPC222185
0.8509	High Similarity	NPC201136
0.8509	High Similarity	NPC196439
0.8509	High Similarity	NPC146165
0.8509	High Similarity	NPC92659
0.8509	High Similarity	NPC227325
0.8509	High Similarity	NPC163780
0.8509	High Similarity	NPC471800
0.8509	High Similarity	NPC2476
0.8509	High Similarity	NPC256612
0.8509	High Similarity	NPC280339
0.8509	High Similarity	NPC167815
0.8509	High Similarity	NPC138360
0.8494	Intermediate Similarity	NPC20216
0.8494	Intermediate Similarity	NPC30027
0.8491	Intermediate Similarity	NPC29056
0.8491	Intermediate Similarity	NPC179183
0.8491	Intermediate Similarity	NPC306821
0.8485	Intermediate Similarity	NPC284007
0.8485	Intermediate Similarity	NPC156082
0.848	Intermediate Similarity	NPC471030
0.8476	Intermediate Similarity	NPC303565
0.8466	Intermediate Similarity	NPC238381
0.8466	Intermediate Similarity	NPC83763
0.8466	Intermediate Similarity	NPC168616
0.8462	Intermediate Similarity	NPC181523
0.8462	Intermediate Similarity	NPC88560
0.8462	Intermediate Similarity	NPC172033
0.8462	Intermediate Similarity	NPC175230
0.8457	Intermediate Similarity	NPC178854
0.8457	Intermediate Similarity	NPC291948
0.8457	Intermediate Similarity	NPC88803
0.8457	Intermediate Similarity	NPC300845
0.8457	Intermediate Similarity	NPC472916
0.8457	Intermediate Similarity	NPC250436
0.8457	Intermediate Similarity	NPC257277
0.8457	Intermediate Similarity	NPC104983
0.8457	Intermediate Similarity	NPC146211
0.8457	Intermediate Similarity	NPC474520
0.8457	Intermediate Similarity	NPC318432
0.8452	Intermediate Similarity	NPC246716
0.8452	Intermediate Similarity	NPC476641
0.8452	Intermediate Similarity	NPC17219
0.8452	Intermediate Similarity	NPC180768
0.8452	Intermediate Similarity	NPC214919
0.8452	Intermediate Similarity	NPC124467
0.8452	Intermediate Similarity	NPC10576
0.8448	Intermediate Similarity	NPC269625
0.8448	Intermediate Similarity	NPC469649
0.8448	Intermediate Similarity	NPC260521
0.8447	Intermediate Similarity	NPC475895
0.8447	Intermediate Similarity	NPC471981
0.8447	Intermediate Similarity	NPC47781
0.8447	Intermediate Similarity	NPC86485
0.8447	Intermediate Similarity	NPC246204
0.8447	Intermediate Similarity	NPC186507
0.8447	Intermediate Similarity	NPC255350
0.8447	Intermediate Similarity	NPC160951
0.8447	Intermediate Similarity	NPC183878
0.8447	Intermediate Similarity	NPC176775
0.8447	Intermediate Similarity	NPC145379
0.8447	Intermediate Similarity	NPC22519
0.8447	Intermediate Similarity	NPC69394
0.8447	Intermediate Similarity	NPC274327
0.8447	Intermediate Similarity	NPC469888
0.8447	Intermediate Similarity	NPC231018
0.8443	Intermediate Similarity	NPC14662
0.8443	Intermediate Similarity	NPC243877
0.8443	Intermediate Similarity	NPC473818
0.8438	Intermediate Similarity	NPC117579
0.8438	Intermediate Similarity	NPC198615
0.8438	Intermediate Similarity	NPC149614
0.8434	Intermediate Similarity	NPC112981
0.8434	Intermediate Similarity	NPC477840
0.8424	Intermediate Similarity	NPC93739
0.8421	Intermediate Similarity	NPC472387
0.8418	Intermediate Similarity	NPC48366
0.8418	Intermediate Similarity	NPC33265
0.8418	Intermediate Similarity	NPC62536
0.8418	Intermediate Similarity	NPC139839
0.8418	Intermediate Similarity	NPC119660
0.8418	Intermediate Similarity	NPC93034
0.8415	Intermediate Similarity	NPC24164
0.8405	Intermediate Similarity	NPC156818
0.8405	Intermediate Similarity	NPC38779
0.8405	Intermediate Similarity	NPC227192
0.8405	Intermediate Similarity	NPC108456
0.8405	Intermediate Similarity	NPC472438
0.8405	Intermediate Similarity	NPC78302
0.8405	Intermediate Similarity	NPC476981
0.8405	Intermediate Similarity	NPC36852
0.8405	Intermediate Similarity	NPC160512
0.8405	Intermediate Similarity	NPC75215
0.8405	Intermediate Similarity	NPC29841
0.8405	Intermediate Similarity	NPC68324
0.8405	Intermediate Similarity	NPC235215
0.8405	Intermediate Similarity	NPC112954
0.8405	Intermediate Similarity	NPC183851
0.8405	Intermediate Similarity	NPC63454
0.8405	Intermediate Similarity	NPC7973
0.8405	Intermediate Similarity	NPC189179
0.8405	Intermediate Similarity	NPC114179
0.8405	Intermediate Similarity	NPC224137
0.8405	Intermediate Similarity	NPC289322
0.8405	Intermediate Similarity	NPC93376
0.8405	Intermediate Similarity	NPC262286
0.8405	Intermediate Similarity	NPC181960
0.8402	Intermediate Similarity	NPC188618
0.8402	Intermediate Similarity	NPC212038
0.8402	Intermediate Similarity	NPC271848
0.8402	Intermediate Similarity	NPC81332
0.8402	Intermediate Similarity	NPC262580
0.8402	Intermediate Similarity	NPC289396
0.84	Intermediate Similarity	NPC223534
0.84	Intermediate Similarity	NPC158214

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 NPC98892 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	998
0.2-0.3	1923
0.3-0.4	2657
0.4-0.5	1781
0.5-0.6	957
0.6-0.7	346
0.7-0.8	129
0.8-0.85	19
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8457	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD2801	Approved
0.8424	Intermediate Similarity	NPD6232	Discontinued
0.8393	Intermediate Similarity	NPD5844	Phase 1
0.8383	Intermediate Similarity	NPD7473	Discontinued
0.8282	Intermediate Similarity	NPD5402	Approved
0.8232	Intermediate Similarity	NPD7768	Phase 2
0.8229	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD447	Suspended
0.8187	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3817	Phase 2
0.8129	Intermediate Similarity	NPD1551	Phase 2
0.8107	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6166	Phase 2
0.8092	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD1934	Approved
0.8012	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD1465	Phase 2
0.7965	Intermediate Similarity	NPD7054	Approved
0.7943	Intermediate Similarity	NPD8313	Approved
0.7943	Intermediate Similarity	NPD8312	Approved
0.7929	Intermediate Similarity	NPD6959	Discontinued
0.7919	Intermediate Similarity	NPD7472	Approved
0.7919	Intermediate Similarity	NPD7074	Phase 3
0.7907	Intermediate Similarity	NPD3818	Discontinued
0.7895	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7819	Suspended
0.7892	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1511	Approved
0.7886	Intermediate Similarity	NPD7808	Phase 3
0.7879	Intermediate Similarity	NPD7411	Suspended
0.787	Intermediate Similarity	NPD5494	Approved
0.7866	Intermediate Similarity	NPD3226	Approved
0.7857	Intermediate Similarity	NPD7075	Discontinued
0.7853	Intermediate Similarity	NPD5403	Approved
0.7791	Intermediate Similarity	NPD1512	Approved
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7756	Intermediate Similarity	NPD1933	Approved
0.7751	Intermediate Similarity	NPD3749	Approved
0.7738	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD5401	Approved
0.7727	Intermediate Similarity	NPD7251	Discontinued
0.7727	Intermediate Similarity	NPD6559	Discontinued
0.7702	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1203	Approved
0.7679	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6797	Phase 2
0.7669	Intermediate Similarity	NPD6799	Approved
0.7662	Intermediate Similarity	NPD6832	Phase 2
0.7647	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6599	Discontinued
0.7605	Intermediate Similarity	NPD4380	Phase 2
0.7593	Intermediate Similarity	NPD3750	Approved
0.759	Intermediate Similarity	NPD1653	Approved
0.7578	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD411	Approved
0.7532	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7515	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD6801	Discontinued
0.7515	Intermediate Similarity	NPD2532	Approved
0.7515	Intermediate Similarity	NPD2534	Approved
0.7515	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD9717	Approved
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7484	Intermediate Similarity	NPD1607	Approved
0.7469	Intermediate Similarity	NPD1549	Phase 2
0.7458	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3926	Phase 2
0.7414	Intermediate Similarity	NPD8127	Discontinued
0.7407	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7228	Approved
0.7399	Intermediate Similarity	NPD919	Approved
0.7391	Intermediate Similarity	NPD4308	Phase 3
0.7391	Intermediate Similarity	NPD1510	Phase 2
0.7363	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1240	Approved
0.7349	Intermediate Similarity	NPD7390	Discontinued
0.7349	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5404	Approved
0.7346	Intermediate Similarity	NPD5405	Approved
0.7346	Intermediate Similarity	NPD5406	Approved
0.7346	Intermediate Similarity	NPD5408	Approved
0.7346	Intermediate Similarity	NPD2796	Approved
0.7342	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2313	Discontinued
0.7337	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6190	Approved
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.732	Intermediate Similarity	NPD8151	Discontinued
0.7317	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7199	Phase 2
0.7314	Intermediate Similarity	NPD1247	Approved
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3748	Approved
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.7245	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7783	Phase 2
0.724	Intermediate Similarity	NPD7435	Discontinued
0.7239	Intermediate Similarity	NPD6099	Approved
0.7239	Intermediate Similarity	NPD6100	Approved
0.7238	Intermediate Similarity	NPD7685	Pre-registration
0.7238	Intermediate Similarity	NPD7038	Approved
0.7238	Intermediate Similarity	NPD7039	Approved
0.7232	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7870	Phase 2
0.7202	Intermediate Similarity	NPD7871	Phase 2
0.7198	Intermediate Similarity	NPD7549	Discontinued
0.7191	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3225	Approved
0.7178	Intermediate Similarity	NPD2799	Discontinued
0.7168	Intermediate Similarity	NPD8455	Phase 2
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7696	Phase 3
0.715	Intermediate Similarity	NPD7697	Approved
0.715	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD2797	Approved
0.7126	Intermediate Similarity	NPD5353	Approved
0.7118	Intermediate Similarity	NPD920	Approved
0.7111	Intermediate Similarity	NPD7177	Discontinued
0.7111	Intermediate Similarity	NPD3751	Discontinued
0.711	Intermediate Similarity	NPD6844	Discontinued
0.7108	Intermediate Similarity	NPD1243	Approved
0.7107	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7874	Approved
0.7107	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6823	Phase 2
0.7089	Intermediate Similarity	NPD1019	Discontinued
0.7088	Intermediate Similarity	NPD5953	Discontinued
0.7083	Intermediate Similarity	NPD6780	Approved
0.7083	Intermediate Similarity	NPD6776	Approved
0.7083	Intermediate Similarity	NPD6777	Approved
0.7083	Intermediate Similarity	NPD6781	Approved
0.7083	Intermediate Similarity	NPD6778	Approved
0.7083	Intermediate Similarity	NPD6779	Approved
0.7083	Intermediate Similarity	NPD6782	Approved
0.7081	Intermediate Similarity	NPD6233	Phase 2
0.7079	Intermediate Similarity	NPD3787	Discontinued
0.7073	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7286	Phase 2
0.7066	Intermediate Similarity	NPD7003	Approved
0.7049	Intermediate Similarity	NPD7240	Approved
0.7045	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD9493	Approved
0.7037	Intermediate Similarity	NPD1613	Approved
0.7037	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7458	Discontinued
0.7019	Intermediate Similarity	NPD3268	Approved
0.7006	Intermediate Similarity	NPD2800	Approved
0.7005	Intermediate Similarity	NPD7701	Phase 2
0.7	Intermediate Similarity	NPD4908	Phase 1
0.7	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD422	Phase 1
0.6983	Remote Similarity	NPD5711	Approved
0.6983	Remote Similarity	NPD5710	Approved
0.6959	Remote Similarity	NPD6273	Approved
0.6957	Remote Similarity	NPD3027	Phase 3
0.6954	Remote Similarity	NPD6386	Approved
0.6954	Remote Similarity	NPD6385	Approved
0.6949	Remote Similarity	NPD6971	Discontinued
0.6944	Remote Similarity	NPD5242	Approved
0.6943	Remote Similarity	NPD9269	Phase 2
0.6914	Remote Similarity	NPD6798	Discontinued
0.6914	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3764	Approved
0.6903	Remote Similarity	NPD9268	Approved
0.69	Remote Similarity	NPD7801	Approved
0.6899	Remote Similarity	NPD4749	Approved
0.6899	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7699	Phase 2
0.6891	Remote Similarity	NPD7700	Phase 2
0.6889	Remote Similarity	NPD7229	Phase 3
0.6886	Remote Similarity	NPD2344	Approved
0.6886	Remote Similarity	NPD7266	Discontinued
0.6882	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4287	Approved
0.6875	Remote Similarity	NPD2798	Approved
0.6872	Remote Similarity	NPD6746	Phase 2
0.6867	Remote Similarity	NPD7033	Discontinued
0.6864	Remote Similarity	NPD8166	Discontinued
0.686	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1778	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