NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	493.12
Volume:	462.07
LogP:	3.52
LogD:	2.394
LogS:	-4.108
# Rotatable Bonds:	12
TPSA:	180.96
# H-Bond Aceptor:	13
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.226
Synthetic Accessibility Score:	3.41
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.749
MDCK Permeability:	3.829468187177554e-05
Pgp-inhibitor:	0.218
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.307
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.919

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	92.02970886230469%
Volume Distribution (VD):	0.629
Pgp-substrate:	8.852356910705566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.853
CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.927
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.88
CYP2C9-substrate:	0.84
CYP2D6-inhibitor:	0.666
CYP2D6-substrate:	0.238
CYP3A4-inhibitor:	0.64
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	9.558
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.426
Drug-inuced Liver Injury (DILI):	0.715
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.179
Skin Sensitization:	0.823
Carcinogencity:	0.022
Eye Corrosion:	0.004
Eye Irritation:	0.709
Respiratory Toxicity:	0.214

Download Data

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

Natural Product: NPC477826

Natural Product ID:	NPC477826
*Common Name:**	Pseudogymnoascin A
IUPAC Name:	methyl 5-hydroxy-2-[3-hydroxy-2-(3-methoxy-2-methyl-3-oxopropoxy)carbonyl-5-methylphenoxy]-3-methoxy-6-nitrobenzoate
Synonyms:
Standard InCHIKey:	KSPCJAHPTUZLJQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H23NO12/c1-10-6-12(24)16(22(28)34-9-11(2)20(26)32-4)14(7-10)35-19-15(31-3)8-13(25)18(23(29)30)17(19)21(27)33-5/h6-8,11,24-25H,9H2,1-5H3
SMILES:	CC1=CC(=C(C(=C1)OC2=C(C=C(C(=C2C(=O)OC)[N+](=O)[O-])O)OC)C(=O)OCC(C)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122177588
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO33556	Pseudogymnoascus sp.	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25732560]

☑ 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
Others	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	MIC95	=	64	ug/ml	PMID[25732560]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC95	=	64	ug/ml	PMID[25732560]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC95	=	64	ug/ml	PMID[25732560]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC95	=	64	ug/ml	PMID[25732560]
NPT20	Organism	Candida albicans	Candida albicans	MIC95	=	64	ug/ml	PMID[25732560]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC95	=	64	ug/ml	PMID[25732560]

☑ 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 NPC477826 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	398
0.1-0.2	2290
0.2-0.3	8400
0.3-0.4	10240
0.4-0.5	5998
0.5-0.6	11066
0.6-0.7	4280
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477827
0.984	High Similarity	NPC477825
0.9689	High Similarity	NPC477828
0.7778	Intermediate Similarity	NPC76478
0.7664	Intermediate Similarity	NPC148391
0.7615	Intermediate Similarity	NPC118189
0.7602	Intermediate Similarity	NPC13249
0.7576	Intermediate Similarity	NPC98416
0.7558	Intermediate Similarity	NPC182853
0.7513	Intermediate Similarity	NPC164527
0.7513	Intermediate Similarity	NPC213382
0.75	Intermediate Similarity	NPC2905
0.7477	Intermediate Similarity	NPC134702
0.7465	Intermediate Similarity	NPC240684
0.746	Intermediate Similarity	NPC106334
0.746	Intermediate Similarity	NPC285527
0.7455	Intermediate Similarity	NPC7560
0.7454	Intermediate Similarity	NPC268223
0.7454	Intermediate Similarity	NPC114468
0.7419	Intermediate Similarity	NPC290227
0.7361	Intermediate Similarity	NPC295479
0.7361	Intermediate Similarity	NPC220241
0.7345	Intermediate Similarity	NPC227033
0.733	Intermediate Similarity	NPC225129
0.7321	Intermediate Similarity	NPC285254
0.7256	Intermediate Similarity	NPC212123
0.7252	Intermediate Similarity	NPC157983
0.7252	Intermediate Similarity	NPC118154
0.7248	Intermediate Similarity	NPC305542
0.7235	Intermediate Similarity	NPC474366
0.7215	Intermediate Similarity	NPC30749
0.7202	Intermediate Similarity	NPC218303
0.7182	Intermediate Similarity	NPC176113
0.7162	Intermediate Similarity	NPC195120
0.7162	Intermediate Similarity	NPC87560
0.7157	Intermediate Similarity	NPC287458
0.7121	Intermediate Similarity	NPC98892
0.711	Intermediate Similarity	NPC171882
0.711	Intermediate Similarity	NPC85661
0.711	Intermediate Similarity	NPC121510
0.7091	Intermediate Similarity	NPC91234
0.7077	Intermediate Similarity	NPC289968
0.7064	Intermediate Similarity	NPC46679
0.7044	Intermediate Similarity	NPC9475
0.7035	Intermediate Similarity	NPC251071
0.7014	Intermediate Similarity	NPC116178
0.7	Intermediate Similarity	NPC217950
0.6982	Remote Similarity	NPC124658
0.6982	Remote Similarity	NPC227361
0.6982	Remote Similarity	NPC321166
0.6982	Remote Similarity	NPC217903
0.6968	Remote Similarity	NPC186569
0.6968	Remote Similarity	NPC61731
0.6946	Remote Similarity	NPC20216
0.6941	Remote Similarity	NPC198160
0.6931	Remote Similarity	NPC156082
0.6927	Remote Similarity	NPC246716
0.6927	Remote Similarity	NPC17219
0.6927	Remote Similarity	NPC38961
0.6919	Remote Similarity	NPC472909
0.6904	Remote Similarity	NPC75069
0.6904	Remote Similarity	NPC199773
0.6903	Remote Similarity	NPC256422
0.6897	Remote Similarity	NPC112981
0.6884	Remote Similarity	NPC54928
0.6878	Remote Similarity	NPC26568
0.6878	Remote Similarity	NPC49487
0.6878	Remote Similarity	NPC99613
0.6869	Remote Similarity	NPC276409
0.6869	Remote Similarity	NPC280937
0.6869	Remote Similarity	NPC75279
0.6869	Remote Similarity	NPC250822
0.6869	Remote Similarity	NPC472915
0.6869	Remote Similarity	NPC298802
0.6866	Remote Similarity	NPC130955
0.686	Remote Similarity	NPC181523
0.6853	Remote Similarity	NPC226973
0.6853	Remote Similarity	NPC208043
0.685	Remote Similarity	NPC472911
0.685	Remote Similarity	NPC472914
0.685	Remote Similarity	NPC181960
0.685	Remote Similarity	NPC108456
0.685	Remote Similarity	NPC469584
0.685	Remote Similarity	NPC222814
0.685	Remote Similarity	NPC245758
0.685	Remote Similarity	NPC472913
0.685	Remote Similarity	NPC472910
0.685	Remote Similarity	NPC96167
0.6847	Remote Similarity	NPC474350
0.6847	Remote Similarity	NPC300984
0.6845	Remote Similarity	NPC124470
0.6845	Remote Similarity	NPC239440
0.6845	Remote Similarity	NPC10576
0.6845	Remote Similarity	NPC20543
0.6845	Remote Similarity	NPC72696
0.6845	Remote Similarity	NPC109827
0.6845	Remote Similarity	NPC1827
0.6837	Remote Similarity	NPC204580
0.6837	Remote Similarity	NPC328119
0.6834	Remote Similarity	NPC167815
0.6834	Remote Similarity	NPC128863
0.6834	Remote Similarity	NPC92659
0.6834	Remote Similarity	NPC196439
0.6834	Remote Similarity	NPC50715
0.6834	Remote Similarity	NPC227325
0.6834	Remote Similarity	NPC280339
0.6834	Remote Similarity	NPC201136
0.6834	Remote Similarity	NPC286052
0.6834	Remote Similarity	NPC183597
0.6834	Remote Similarity	NPC146165
0.6834	Remote Similarity	NPC471800
0.6834	Remote Similarity	NPC163780
0.6834	Remote Similarity	NPC208197
0.6834	Remote Similarity	NPC4455
0.6834	Remote Similarity	NPC138360
0.6834	Remote Similarity	NPC37392
0.6834	Remote Similarity	NPC213622
0.6834	Remote Similarity	NPC2476
0.6832	Remote Similarity	NPC266314
0.6829	Remote Similarity	NPC272485
0.6829	Remote Similarity	NPC292788
0.6827	Remote Similarity	NPC139350
0.6821	Remote Similarity	NPC46941
0.6818	Remote Similarity	NPC317567
0.6816	Remote Similarity	NPC168616
0.6816	Remote Similarity	NPC83763
0.6816	Remote Similarity	NPC238381
0.6814	Remote Similarity	NPC267153
0.6814	Remote Similarity	NPC25361
0.6812	Remote Similarity	NPC158226
0.6812	Remote Similarity	NPC188618
0.6806	Remote Similarity	NPC83019
0.6802	Remote Similarity	NPC306821
0.68	Remote Similarity	NPC178854
0.68	Remote Similarity	NPC472916
0.68	Remote Similarity	NPC474520
0.6798	Remote Similarity	NPC93739
0.6796	Remote Similarity	NPC476279
0.6791	Remote Similarity	NPC170333
0.6784	Remote Similarity	NPC260604
0.6784	Remote Similarity	NPC231018
0.6784	Remote Similarity	NPC47781
0.6784	Remote Similarity	NPC183878
0.6784	Remote Similarity	NPC160951
0.6784	Remote Similarity	NPC274327
0.6784	Remote Similarity	NPC176775
0.6784	Remote Similarity	NPC299435
0.6784	Remote Similarity	NPC86485
0.6784	Remote Similarity	NPC22519
0.6784	Remote Similarity	NPC255350
0.6784	Remote Similarity	NPC145379
0.6784	Remote Similarity	NPC246204
0.6784	Remote Similarity	NPC69394
0.6782	Remote Similarity	NPC292415
0.678	Remote Similarity	NPC29160
0.6769	Remote Similarity	NPC329830
0.6768	Remote Similarity	NPC308451
0.6768	Remote Similarity	NPC117579
0.6766	Remote Similarity	NPC156057
0.6766	Remote Similarity	NPC75215
0.6766	Remote Similarity	NPC224137
0.6766	Remote Similarity	NPC189179
0.6766	Remote Similarity	NPC93376
0.6766	Remote Similarity	NPC78302
0.6766	Remote Similarity	NPC474208
0.6766	Remote Similarity	NPC7973
0.6766	Remote Similarity	NPC235215
0.6766	Remote Similarity	NPC472438
0.6766	Remote Similarity	NPC162869
0.6766	Remote Similarity	NPC227192
0.6766	Remote Similarity	NPC29841
0.6766	Remote Similarity	NPC474836
0.6766	Remote Similarity	NPC475267
0.6766	Remote Similarity	NPC470402
0.6766	Remote Similarity	NPC48208
0.6765	Remote Similarity	NPC197168
0.6765	Remote Similarity	NPC284007
0.6758	Remote Similarity	NPC15987
0.6751	Remote Similarity	NPC294502
0.6751	Remote Similarity	NPC200221
0.675	Remote Similarity	NPC255807
0.675	Remote Similarity	NPC2928
0.675	Remote Similarity	NPC32557
0.675	Remote Similarity	NPC20830
0.675	Remote Similarity	NPC189960
0.675	Remote Similarity	NPC31018
0.675	Remote Similarity	NPC476642
0.675	Remote Similarity	NPC256612
0.6749	Remote Similarity	NPC303565
0.6749	Remote Similarity	NPC66288
0.6749	Remote Similarity	NPC103201
0.6749	Remote Similarity	NPC473106
0.6748	Remote Similarity	NPC234331
0.6746	Remote Similarity	NPC289147
0.6742	Remote Similarity	NPC475768
0.6736	Remote Similarity	NPC214919
0.6736	Remote Similarity	NPC124467
0.6735	Remote Similarity	NPC33265
0.6735	Remote Similarity	NPC93034
0.6735	Remote Similarity	NPC119660

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 NPC477826 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	856
0.2-0.3	1744
0.3-0.4	2484
0.4-0.5	2383
0.5-0.6	1205
0.6-0.7	189
0.7-0.8	3
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
0.7685	Intermediate Similarity	NPD2899	Discontinued
0.7345	Intermediate Similarity	NPD8067	Phase 3
0.7256	Intermediate Similarity	NPD6296	Discontinued
0.7205	Intermediate Similarity	NPD6625	Approved
0.7	Intermediate Similarity	NPD2821	Approved
0.6961	Remote Similarity	NPD1221	Approved
0.6853	Remote Similarity	NPD2672	Discontinued
0.685	Remote Similarity	NPD955	Approved
0.6818	Remote Similarity	NPD8367	Approved
0.6814	Remote Similarity	NPD1220	Phase 1
0.6784	Remote Similarity	NPD2801	Approved
0.6776	Remote Similarity	NPD7125	Discontinued
0.6774	Remote Similarity	NPD6874	Approved
0.6768	Remote Similarity	NPD2366	Approved
0.6712	Remote Similarity	NPD7476	Discontinued
0.6707	Remote Similarity	NPD8492	Approved
0.67	Remote Similarity	NPD3251	Approved
0.6682	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1898	Discontinued
0.6667	Remote Similarity	NPD2339	Phase 3
0.6667	Remote Similarity	NPD3817	Phase 2
0.6634	Remote Similarity	NPD6232	Discontinued
0.6633	Remote Similarity	NPD3684	Discontinued
0.6624	Remote Similarity	NPD6723	Discontinued
0.6622	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD6104	Discontinued
0.6618	Remote Similarity	NPD7473	Discontinued
0.6606	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5242	Approved
0.6588	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD5402	Approved
0.6569	Remote Similarity	NPD3252	Approved
0.6567	Remote Similarity	NPD1934	Approved
0.6562	Remote Similarity	NPD1551	Phase 2
0.6552	Remote Similarity	NPD3882	Suspended
0.6552	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5006	Approved
0.6532	Remote Similarity	NPD5005	Approved
0.653	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7256	Discontinued
0.649	Remote Similarity	NPD2248	Approved
0.649	Remote Similarity	NPD2246	Approved
0.6482	Remote Similarity	NPD711	Discontinued
0.6476	Remote Similarity	NPD5844	Phase 1
0.6473	Remote Similarity	NPD7891	Discontinued
0.6453	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6045	Phase 3
0.644	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.644	Remote Similarity	NPD447	Suspended
0.6429	Remote Similarity	NPD3818	Discontinued
0.6422	Remote Similarity	NPD6198	Phase 1
0.6411	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD6166	Phase 2
0.6402	Remote Similarity	NPD9468	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7546	Discontinued
0.6398	Remote Similarity	NPD7054	Approved
0.6393	Remote Similarity	NPD1852	Discontinued
0.6389	Remote Similarity	NPD8461	Discontinued
0.6386	Remote Similarity	NPD3296	Phase 1
0.6385	Remote Similarity	NPD7038	Approved
0.6385	Remote Similarity	NPD7039	Approved
0.6384	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD5494	Approved
0.6376	Remote Similarity	NPD1945	Phase 1
0.6368	Remote Similarity	NPD7472	Approved
0.6368	Remote Similarity	NPD7074	Phase 3
0.6359	Remote Similarity	NPD3453	Discontinued
0.6356	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD3912	Discontinued
0.6355	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD4420	Approved
0.6346	Remote Similarity	NPD2680	Approved
0.6346	Remote Similarity	NPD2681	Approved
0.6345	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD6184	Discontinued
0.6335	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD5914	Approved
0.6332	Remote Similarity	NPD1511	Approved
0.633	Remote Similarity	NPD2845	Phase 2
0.633	Remote Similarity	NPD2843	Phase 2
0.6325	Remote Similarity	NPD5519	Discontinued
0.6304	Remote Similarity	NPD7783	Phase 2
0.6304	Remote Similarity	NPD683	Approved
0.6304	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD3437	Discontinued
0.6295	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7559	Phase 2
0.6284	Remote Similarity	NPD3398	Discontinued
0.6284	Remote Similarity	NPD2792	Approved
0.628	Remote Similarity	NPD7075	Discontinued
0.6279	Remote Similarity	NPD7808	Phase 3
0.6279	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6385	Approved
0.6275	Remote Similarity	NPD6386	Approved
0.6272	Remote Similarity	NPD7584	Approved
0.627	Remote Similarity	NPD4846	Phase 2
0.6269	Remote Similarity	NPD1512	Approved
0.6263	Remote Similarity	NPD1196	Approved
0.6262	Remote Similarity	NPD5353	Approved
0.6262	Remote Similarity	NPD6797	Phase 2
0.6261	Remote Similarity	NPD3925	Approved
0.625	Remote Similarity	NPD6799	Approved
0.625	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD4049	Phase 2
0.6244	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5403	Approved
0.6235	Remote Similarity	NPD1483	Discontinued
0.6233	Remote Similarity	NPD7251	Discontinued
0.6233	Remote Similarity	NPD6559	Discontinued
0.6225	Remote Similarity	NPD6599	Discontinued
0.6224	Remote Similarity	NPD2935	Discontinued
0.6219	Remote Similarity	NPD2533	Approved
0.6219	Remote Similarity	NPD2534	Approved
0.6219	Remote Similarity	NPD2532	Approved
0.6214	Remote Similarity	NPD1465	Phase 2
0.6214	Remote Similarity	NPD7819	Suspended
0.6212	Remote Similarity	NPD1195	Approved
0.6211	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD4668	Phase 2
0.6204	Remote Similarity	NPD7549	Discontinued
0.6204	Remote Similarity	NPD2802	Phase 3
0.6188	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD3298	Approved
0.6179	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD2906	Approved
0.6174	Remote Similarity	NPD2907	Approved
0.6174	Remote Similarity	NPD7585	Approved
0.6172	Remote Similarity	NPD6234	Discontinued
0.6171	Remote Similarity	NPD6213	Phase 3
0.6171	Remote Similarity	NPD6212	Phase 3
0.6171	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.617	Remote Similarity	NPD8404	Phase 2
0.6169	Remote Similarity	NPD1543	Discontinued
0.6165	Remote Similarity	NPD37	Approved
0.6161	Remote Similarity	NPD4604	Approved
0.6161	Remote Similarity	NPD5711	Approved
0.6161	Remote Similarity	NPD4605	Approved
0.6161	Remote Similarity	NPD5710	Approved
0.6161	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4967	Phase 2
0.6154	Remote Similarity	NPD4966	Approved
0.6154	Remote Similarity	NPD4965	Approved
0.615	Remote Similarity	NPD6777	Approved
0.615	Remote Similarity	NPD6782	Approved
0.615	Remote Similarity	NPD6778	Approved
0.615	Remote Similarity	NPD6779	Approved
0.615	Remote Similarity	NPD6780	Approved
0.615	Remote Similarity	NPD6781	Approved
0.615	Remote Similarity	NPD6776	Approved
0.6146	Remote Similarity	NPD4678	Approved
0.6146	Remote Similarity	NPD4675	Approved
0.6143	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD6746	Phase 2
0.6139	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5401	Approved
0.6137	Remote Similarity	NPD7827	Phase 1
0.6135	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.613	Remote Similarity	NPD7583	Approved
0.6124	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5860	Discontinued
0.6119	Remote Similarity	NPD3154	Approved
0.6119	Remote Similarity	NPD3153	Approved
0.6117	Remote Similarity	NPD7411	Suspended
0.6114	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6959	Discontinued
0.6114	Remote Similarity	NPD2247	Approved
0.6114	Remote Similarity	NPD2249	Approved
0.6109	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD230	Phase 1
0.6103	Remote Similarity	NPD1933	Approved
0.61	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.61	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3226	Approved
0.6098	Remote Similarity	NPD3455	Phase 2
0.6096	Remote Similarity	NPD6823	Phase 2
0.6092	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6801	Discontinued
0.6087	Remote Similarity	NPD6844	Discontinued
0.6082	Remote Similarity	NPD7922	Phase 1
0.608	Remote Similarity	NPD75	Approved
0.608	Remote Similarity	NPD9277	Approved
0.6077	Remote Similarity	NPD7768	Phase 2
0.6073	Remote Similarity	NPD1019	Discontinued
0.6071	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.607	Remote Similarity	NPD7435	Discontinued
0.607	Remote Similarity	NPD7698	Approved
0.607	Remote Similarity	NPD7697	Approved
0.607	Remote Similarity	NPD7696	Phase 3
0.6068	Remote Similarity	NPD4380	Phase 2
0.6067	Remote Similarity	NPD7907	Approved
0.6066	Remote Similarity	NPD5677	Discontinued
0.6062	Remote Similarity	NPD7862	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