NPASS Compound

Structure

NPC161611 OpenBabel07101719242D 22 23 0 0 1 0 0 0 0 0999 V2000 -1.5637 -1.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1564 3.0633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1564 2.0633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2903 3.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2903 1.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4243 3.0633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3209 1.2256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8209 2.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9010 1.5605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6923 0.0633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6328 -1.6123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4243 2.0633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8262 0.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9556 0.2948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5583 1.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4837 -2.6012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6357 -0.4383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6923 2.0633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1679 2.2407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5583 0.5633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1490 -0.9888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 20 1 0 0 0 0 9 13 2 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 17 2 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 22 1 1 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	299.829
LogP:	1.528
LogD:	1.626
LogS:	-2.796
# Rotatable Bonds:	6
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.789
Synthetic Accessibility Score:	2.764
Fsp3:	0.188
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:	-4.641
MDCK Permeability:	3.4522494388511404e-05
Pgp-inhibitor:	0.083
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.438
Plasma Protein Binding (PPB):	88.09896087646484%
Volume Distribution (VD):	1.003
Pgp-substrate:	14.897910118103027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.876
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.72
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.139
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.159
CYP3A4-substrate:	0.202

ADMET: Excretion

Clearance (CL):	6.695
Half-life (T1/2):	0.945

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.979
Rat Oral Acute Toxicity:	0.786
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.847
Carcinogencity:	0.941
Eye Corrosion:	0.066
Eye Irritation:	0.959
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC161611

Natural Product ID:	NPC161611
*Common Name:**	Grandiuvarone A
IUPAC Name:	[(4R)-4-acetyloxy-5-oxo-4H-oxepin-3-yl]methyl benzoate
Synonyms:
Standard InCHIKey:	WSNISKVPPPGLFK-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-11(17)22-15-13(9-20-8-7-14(15)18)10-21-16(19)12-5-3-2-4-6-12/h2-9,15H,10H2,1H3/t15-/m1/s1
SMILES:	CC(=O)O[C@@H]1C(=COC=CC1=O)COC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522552
PubChem CID:	11507728
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO10791	Uvaria grandiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643056]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	Leaf; Twig	n.a.	n.a.	PMID[30835120]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10791	Uvaria grandiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10791	Uvaria grandiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	2

Activity Type	# Activity
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	0.7	ug.mL-1	PMID[558995]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	1.5	ug.mL-1	PMID[558995]
NPT2	Others	Unspecified		Inhibition	=	98.2	%	PMID[558996]
NPT2	Others	Unspecified		IC50	=	3100.0	nM	PMID[558996]

☑ 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 NPC161611 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	249
0.1-0.2	1309
0.2-0.3	4098
0.3-0.4	9164
0.4-0.5	10800
0.5-0.6	10825
0.6-0.7	5662
0.7-0.8	515
0.8-0.85	61
0.85-0.9	11
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.8952	High Similarity	NPC474365
0.8952	High Similarity	NPC301943
0.8889	High Similarity	NPC474364
0.8654	High Similarity	NPC276775
0.8654	High Similarity	NPC92754
0.8654	High Similarity	NPC249912
0.8571	High Similarity	NPC78701
0.8571	High Similarity	NPC35448
0.8571	High Similarity	NPC225060
0.8559	High Similarity	NPC474157
0.8545	High Similarity	NPC469636
0.8491	Intermediate Similarity	NPC146351
0.8491	Intermediate Similarity	NPC325497
0.8462	Intermediate Similarity	NPC130398
0.8411	Intermediate Similarity	NPC70624
0.8407	Intermediate Similarity	NPC474176
0.8378	Intermediate Similarity	NPC17417
0.8378	Intermediate Similarity	NPC10251
0.8378	Intermediate Similarity	NPC265407
0.8378	Intermediate Similarity	NPC83628
0.8364	Intermediate Similarity	NPC30594
0.8364	Intermediate Similarity	NPC37622
0.8364	Intermediate Similarity	NPC119271
0.8333	Intermediate Similarity	NPC308744
0.8333	Intermediate Similarity	NPC307651
0.8333	Intermediate Similarity	NPC474363
0.8319	Intermediate Similarity	NPC474314
0.8318	Intermediate Similarity	NPC203925
0.8318	Intermediate Similarity	NPC118343
0.8305	Intermediate Similarity	NPC473243
0.8304	Intermediate Similarity	NPC251854
0.8304	Intermediate Similarity	NPC93084
0.8304	Intermediate Similarity	NPC214067
0.8304	Intermediate Similarity	NPC196246
0.8288	Intermediate Similarity	NPC56493
0.8273	Intermediate Similarity	NPC209632
0.8273	Intermediate Similarity	NPC269457
0.8261	Intermediate Similarity	NPC210092
0.8246	Intermediate Similarity	NPC272524
0.8241	Intermediate Similarity	NPC42211
0.823	Intermediate Similarity	NPC305912
0.823	Intermediate Similarity	NPC1082
0.823	Intermediate Similarity	NPC476003
0.8197	Intermediate Similarity	NPC476599
0.819	Intermediate Similarity	NPC149691
0.8182	Intermediate Similarity	NPC31786
0.8182	Intermediate Similarity	NPC114594
0.8165	Intermediate Similarity	NPC188895
0.8158	Intermediate Similarity	NPC82899
0.8158	Intermediate Similarity	NPC270699
0.8142	Intermediate Similarity	NPC174099
0.8125	Intermediate Similarity	NPC470391
0.8103	Intermediate Similarity	NPC474685
0.8091	Intermediate Similarity	NPC89886
0.8091	Intermediate Similarity	NPC60679
0.8087	Intermediate Similarity	NPC128368
0.807	Intermediate Similarity	NPC260818
0.807	Intermediate Similarity	NPC210089
0.8053	Intermediate Similarity	NPC269023
0.8053	Intermediate Similarity	NPC99846
0.8034	Intermediate Similarity	NPC216387
0.8017	Intermediate Similarity	NPC153053
0.8017	Intermediate Similarity	NPC477411
0.8	Intermediate Similarity	NPC321852
0.7981	Intermediate Similarity	NPC173443
0.7953	Intermediate Similarity	NPC475569
0.7949	Intermediate Similarity	NPC474408
0.7937	Intermediate Similarity	NPC42234
0.7899	Intermediate Similarity	NPC469574
0.7899	Intermediate Similarity	NPC217423
0.7899	Intermediate Similarity	NPC45104
0.7895	Intermediate Similarity	NPC85493
0.7895	Intermediate Similarity	NPC40178
0.7881	Intermediate Similarity	NPC226093
0.7863	Intermediate Similarity	NPC196075
0.7845	Intermediate Similarity	NPC158282
0.7838	Intermediate Similarity	NPC45613
0.7823	Intermediate Similarity	NPC246166
0.7823	Intermediate Similarity	NPC295664
0.7815	Intermediate Similarity	NPC190298
0.7812	Intermediate Similarity	NPC477360
0.7807	Intermediate Similarity	NPC47536
0.7797	Intermediate Similarity	NPC470764
0.7795	Intermediate Similarity	NPC272946
0.7788	Intermediate Similarity	NPC89377
0.7787	Intermediate Similarity	NPC50872
0.7778	Intermediate Similarity	NPC5472
0.7769	Intermediate Similarity	NPC204784
0.7752	Intermediate Similarity	NPC477364
0.7742	Intermediate Similarity	NPC471466
0.7734	Intermediate Similarity	NPC469519
0.7731	Intermediate Similarity	NPC188907
0.7714	Intermediate Similarity	NPC304760
0.7705	Intermediate Similarity	NPC230951
0.7692	Intermediate Similarity	NPC477368
0.7692	Intermediate Similarity	NPC212415
0.7692	Intermediate Similarity	NPC318107
0.7686	Intermediate Similarity	NPC94637
0.7686	Intermediate Similarity	NPC152159
0.7685	Intermediate Similarity	NPC261181
0.7664	Intermediate Similarity	NPC119631
0.7661	Intermediate Similarity	NPC475692
0.7661	Intermediate Similarity	NPC474283
0.7656	Intermediate Similarity	NPC471832
0.7656	Intermediate Similarity	NPC473247
0.7647	Intermediate Similarity	NPC228936
0.7647	Intermediate Similarity	NPC81808
0.7642	Intermediate Similarity	NPC220893
0.7638	Intermediate Similarity	NPC472707
0.7636	Intermediate Similarity	NPC270654
0.7634	Intermediate Similarity	NPC477367
0.7634	Intermediate Similarity	NPC265459
0.7634	Intermediate Similarity	NPC472247
0.7634	Intermediate Similarity	NPC232888
0.7634	Intermediate Similarity	NPC290833
0.7634	Intermediate Similarity	NPC475262
0.7634	Intermediate Similarity	NPC270364
0.7627	Intermediate Similarity	NPC13784
0.7623	Intermediate Similarity	NPC90522
0.7623	Intermediate Similarity	NPC328459
0.7619	Intermediate Similarity	NPC121272
0.7611	Intermediate Similarity	NPC160382
0.7611	Intermediate Similarity	NPC234305
0.7607	Intermediate Similarity	NPC291799
0.7607	Intermediate Similarity	NPC167504
0.7607	Intermediate Similarity	NPC243355
0.7603	Intermediate Similarity	NPC240664
0.76	Intermediate Similarity	NPC475691
0.76	Intermediate Similarity	NPC472704
0.7597	Intermediate Similarity	NPC282230
0.7597	Intermediate Similarity	NPC183348
0.7596	Intermediate Similarity	NPC58616
0.7593	Intermediate Similarity	NPC77273
0.7589	Intermediate Similarity	NPC112552
0.7586	Intermediate Similarity	NPC281604
0.7583	Intermediate Similarity	NPC220540
0.7583	Intermediate Similarity	NPC471616
0.7583	Intermediate Similarity	NPC135730
0.7583	Intermediate Similarity	NPC100353
0.7578	Intermediate Similarity	NPC301857
0.7576	Intermediate Similarity	NPC477358
0.7576	Intermediate Similarity	NPC194769
0.7576	Intermediate Similarity	NPC285221
0.7565	Intermediate Similarity	NPC51174
0.7563	Intermediate Similarity	NPC87069
0.7561	Intermediate Similarity	NPC72977
0.7557	Intermediate Similarity	NPC477359
0.7557	Intermediate Similarity	NPC472250
0.7545	Intermediate Similarity	NPC12695
0.7544	Intermediate Similarity	NPC269644
0.7544	Intermediate Similarity	NPC249067
0.7544	Intermediate Similarity	NPC85977
0.7542	Intermediate Similarity	NPC54626
0.7542	Intermediate Similarity	NPC79496
0.7542	Intermediate Similarity	NPC23332
0.7541	Intermediate Similarity	NPC94298
0.7541	Intermediate Similarity	NPC27633
0.7541	Intermediate Similarity	NPC293424
0.754	Intermediate Similarity	NPC125053
0.7538	Intermediate Similarity	NPC470977
0.7538	Intermediate Similarity	NPC196979
0.7538	Intermediate Similarity	NPC15083
0.7538	Intermediate Similarity	NPC470976
0.7537	Intermediate Similarity	NPC251294
0.7523	Intermediate Similarity	NPC23453
0.7522	Intermediate Similarity	NPC25458
0.7521	Intermediate Similarity	NPC470860
0.7521	Intermediate Similarity	NPC128825
0.752	Intermediate Similarity	NPC472703
0.752	Intermediate Similarity	NPC223351
0.7519	Intermediate Similarity	NPC66246
0.7519	Intermediate Similarity	NPC86772
0.7519	Intermediate Similarity	NPC170546
0.75	Intermediate Similarity	NPC20485
0.75	Intermediate Similarity	NPC472318
0.75	Intermediate Similarity	NPC110704
0.75	Intermediate Similarity	NPC144547
0.75	Intermediate Similarity	NPC79699
0.75	Intermediate Similarity	NPC98911
0.75	Intermediate Similarity	NPC476484
0.748	Intermediate Similarity	NPC4164
0.7477	Intermediate Similarity	NPC253423
0.7477	Intermediate Similarity	NPC103048
0.7463	Intermediate Similarity	NPC272523
0.7463	Intermediate Similarity	NPC276652
0.7463	Intermediate Similarity	NPC325805
0.746	Intermediate Similarity	NPC473942
0.7458	Intermediate Similarity	NPC183648
0.7456	Intermediate Similarity	NPC91820
0.7456	Intermediate Similarity	NPC82426
0.7453	Intermediate Similarity	NPC286608
0.7453	Intermediate Similarity	NPC169050
0.7429	Intermediate Similarity	NPC294134
0.7422	Intermediate Similarity	NPC110211
0.7422	Intermediate Similarity	NPC169913
0.7422	Intermediate Similarity	NPC475236
0.7422	Intermediate Similarity	NPC51292
0.7422	Intermediate Similarity	NPC472706
0.7422	Intermediate Similarity	NPC204579
0.7419	Intermediate Similarity	NPC233282

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 NPC161611 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	880
0.2-0.3	1497
0.3-0.4	2853
0.4-0.5	2281
0.5-0.6	1055
0.6-0.7	328
0.7-0.8	28
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8393	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD2182	Approved
0.8318	Intermediate Similarity	NPD1238	Approved
0.8304	Intermediate Similarity	NPD2067	Discontinued
0.8182	Intermediate Similarity	NPD164	Approved
0.8103	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9259	Approved
0.7692	Intermediate Similarity	NPD9257	Approved
0.7685	Intermediate Similarity	NPD1202	Approved
0.7544	Intermediate Similarity	NPD1237	Approved
0.7541	Intermediate Similarity	NPD9545	Approved
0.7521	Intermediate Similarity	NPD9493	Approved
0.7453	Intermediate Similarity	NPD1282	Approved
0.7442	Intermediate Similarity	NPD6832	Phase 2
0.744	Intermediate Similarity	NPD6287	Discontinued
0.7422	Intermediate Similarity	NPD1019	Discontinued
0.7417	Intermediate Similarity	NPD1241	Discontinued
0.7411	Intermediate Similarity	NPD9495	Approved
0.7407	Intermediate Similarity	NPD9256	Approved
0.7407	Intermediate Similarity	NPD9258	Approved
0.7381	Intermediate Similarity	NPD9717	Approved
0.728	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2198	Approved
0.7266	Intermediate Similarity	NPD2199	Approved
0.7265	Intermediate Similarity	NPD3134	Approved
0.725	Intermediate Similarity	NPD969	Suspended
0.7203	Intermediate Similarity	NPD1358	Approved
0.7194	Intermediate Similarity	NPD3887	Approved
0.7165	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD9261	Approved
0.7155	Intermediate Similarity	NPD6647	Phase 2
0.7154	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9260	Approved
0.7143	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5909	Discontinued
0.7092	Intermediate Similarity	NPD6799	Approved
0.7077	Intermediate Similarity	NPD1203	Approved
0.7073	Intermediate Similarity	NPD2629	Approved
0.7068	Intermediate Similarity	NPD2313	Discontinued
0.7042	Intermediate Similarity	NPD5401	Approved
0.7037	Intermediate Similarity	NPD1933	Approved
0.7029	Intermediate Similarity	NPD2353	Approved
0.7029	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7236	Approved
0.7015	Intermediate Similarity	NPD6233	Phase 2
0.7009	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1929	Approved
0.7009	Intermediate Similarity	NPD1930	Approved
0.7007	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD5667	Approved
0.6992	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3972	Approved
0.6963	Remote Similarity	NPD4307	Phase 2
0.6947	Remote Similarity	NPD3267	Approved
0.6947	Remote Similarity	NPD3266	Approved
0.6944	Remote Similarity	NPD5403	Approved
0.694	Remote Similarity	NPD6798	Discontinued
0.6934	Remote Similarity	NPD2569	Approved
0.6934	Remote Similarity	NPD2567	Approved
0.693	Remote Similarity	NPD1989	Approved
0.6917	Remote Similarity	NPD9264	Approved
0.6917	Remote Similarity	NPD9263	Approved
0.6917	Remote Similarity	NPD9267	Approved
0.6912	Remote Similarity	NPD447	Suspended
0.6912	Remote Similarity	NPD230	Phase 1
0.6906	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2066	Phase 3
0.6894	Remote Similarity	NPD2788	Approved
0.6889	Remote Similarity	NPD4062	Phase 3
0.688	Remote Similarity	NPD4198	Discontinued
0.687	Remote Similarity	NPD1876	Approved
0.6866	Remote Similarity	NPD7008	Discontinued
0.686	Remote Similarity	NPD74	Approved
0.686	Remote Similarity	NPD9266	Approved
0.6857	Remote Similarity	NPD9490	Approved
0.685	Remote Similarity	NPD1894	Discontinued
0.6831	Remote Similarity	NPD2354	Approved
0.6825	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3496	Discontinued
0.6818	Remote Similarity	NPD9567	Approved
0.6818	Remote Similarity	NPD552	Approved
0.6818	Remote Similarity	NPD553	Approved
0.6815	Remote Similarity	NPD3764	Approved
0.6815	Remote Similarity	NPD411	Approved
0.6809	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6599	Discontinued
0.6788	Remote Similarity	NPD6355	Discontinued
0.6786	Remote Similarity	NPD3673	Approved
0.6786	Remote Similarity	NPD2346	Discontinued
0.6786	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3672	Approved
0.6781	Remote Similarity	NPD7239	Suspended
0.678	Remote Similarity	NPD1932	Approved
0.6779	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5277	Phase 2
0.6772	Remote Similarity	NPD2347	Approved
0.6767	Remote Similarity	NPD2798	Approved
0.6763	Remote Similarity	NPD4308	Phase 3
0.6763	Remote Similarity	NPD3748	Approved
0.6761	Remote Similarity	NPD4628	Phase 3
0.6759	Remote Similarity	NPD9491	Approved
0.6754	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7798	Approved
0.675	Remote Similarity	NPD9697	Approved
0.6741	Remote Similarity	NPD6039	Approved
0.6733	Remote Similarity	NPD5402	Approved
0.6715	Remote Similarity	NPD3142	Approved
0.6715	Remote Similarity	NPD3140	Approved
0.6714	Remote Similarity	NPD2935	Discontinued
0.6714	Remote Similarity	NPD1551	Phase 2
0.6714	Remote Similarity	NPD2796	Approved
0.6711	Remote Similarity	NPD6801	Discontinued
0.6692	Remote Similarity	NPD2797	Approved
0.6691	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD9281	Approved
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD1087	Approved
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD5951	Approved
0.6667	Remote Similarity	NPD957	Approved
0.6645	Remote Similarity	NPD7075	Discontinued
0.6644	Remote Similarity	NPD5049	Phase 3
0.6642	Remote Similarity	NPD6085	Phase 2
0.6642	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD5647	Approved
0.6642	Remote Similarity	NPD7713	Phase 3
0.6619	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD17	Approved
0.6615	Remote Similarity	NPD5305	Approved
0.6615	Remote Similarity	NPD5306	Approved
0.6604	Remote Similarity	NPD227	Approved
0.6604	Remote Similarity	NPD225	Approved
0.6597	Remote Similarity	NPD6190	Approved
0.6594	Remote Similarity	NPD3373	Approved
0.6594	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD9494	Approved
0.6585	Remote Similarity	NPD2329	Discontinued
0.6569	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD4106	Approved
0.6565	Remote Similarity	NPD4135	Approved
0.6565	Remote Similarity	NPD4136	Approved
0.656	Remote Similarity	NPD9508	Approved
0.6552	Remote Similarity	NPD1693	Approved
0.6549	Remote Similarity	NPD800	Approved
0.6538	Remote Similarity	NPD5691	Approved
0.6533	Remote Similarity	NPD958	Approved
0.6532	Remote Similarity	NPD1317	Discontinued
0.6528	Remote Similarity	NPD3750	Approved
0.6525	Remote Similarity	NPD5926	Approved
0.6522	Remote Similarity	NPD520	Approved
0.6515	Remote Similarity	NPD1281	Approved
0.6515	Remote Similarity	NPD4807	Approved
0.6515	Remote Similarity	NPD4806	Approved
0.6513	Remote Similarity	NPD3817	Phase 2
0.6512	Remote Similarity	NPD5536	Phase 2
0.6508	Remote Similarity	NPD5535	Approved
0.6503	Remote Similarity	NPD2897	Discontinued
0.6503	Remote Similarity	NPD1549	Phase 2
0.65	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD3225	Approved
0.6491	Remote Similarity	NPD1086	Approved
0.6491	Remote Similarity	NPD1090	Approved
0.6491	Remote Similarity	NPD1089	Approved
0.6489	Remote Similarity	NPD1778	Approved
0.6486	Remote Similarity	NPD920	Approved
0.648	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD2438	Suspended
0.6475	Remote Similarity	NPD2979	Phase 3
0.6475	Remote Similarity	NPD5048	Discontinued
0.6475	Remote Similarity	NPD1240	Approved
0.6471	Remote Similarity	NPD7057	Phase 3
0.6471	Remote Similarity	NPD7058	Phase 2
0.6466	Remote Similarity	NPD1608	Approved
0.6466	Remote Similarity	NPD1481	Phase 2
0.6454	Remote Similarity	NPD2670	Approved
0.6449	Remote Similarity	NPD1296	Phase 2
0.6446	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD2625	Approved
0.6444	Remote Similarity	NPD2628	Approved
0.6444	Remote Similarity	NPD2627	Approved
0.6444	Remote Similarity	NPD2159	Approved
0.6444	Remote Similarity	NPD2160	Approved
0.6444	Remote Similarity	NPD2626	Approved
0.6444	Remote Similarity	NPD6362	Approved
0.6439	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3847	Discontinued
0.6438	Remote Similarity	NPD7440	Discontinued
0.6434	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4622	Approved
0.6429	Remote Similarity	NPD4618	Approved
0.6424	Remote Similarity	NPD7411	Suspended
0.6424	Remote Similarity	NPD5889	Approved
0.6424	Remote Similarity	NPD5890	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