NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.08
Volume:	220.923
LogP:	2.403
LogD:	1.852
LogS:	-2.564
# Rotatable Bonds:	2
TPSA:	38.83
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.56
Synthetic Accessibility Score:	3.572
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.617
MDCK Permeability:	3.156030652462505e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.167
30% Bioavailability (F30%):	0.393

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.634
Plasma Protein Binding (PPB):	88.37267303466797%
Volume Distribution (VD):	1.648
Pgp-substrate:	10.15719223022461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.368
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.61
CYP2C19-substrate:	0.173
CYP2C9-inhibitor:	0.346
CYP2C9-substrate:	0.217
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.315
CYP3A4-inhibitor:	0.24
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	9.186
Half-life (T1/2):	0.425

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.241
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.515
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.938
Carcinogencity:	0.378
Eye Corrosion:	0.707
Eye Irritation:	0.942
Respiratory Toxicity:	0.82

Download Data

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

Natural Product: NPC98911

Natural Product ID:	NPC98911
*Common Name:**	Goniothalamin Epoxide
IUPAC Name:	(2R)-2-[(2S,3S)-3-phenyloxiran-2-yl]-2,3-dihydropyran-6-one
Synonyms:	Goniothalamin Epoxide
Standard InCHIKey:	GMKNQTQLCWOLSD-WXHSDQCUSA-N
Standard InCHI:	InChI=1S/C13H12O3/c14-11-8-4-7-10(15-11)13-12(16-13)9-5-2-1-3-6-9/h1-6,8,10,12-13H,7H2/t10-,12+,13+/m1/s1
SMILES:	c1ccc(cc1)[C@H]1[C@H]([C@H]2CC=CC(=O)O2)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468242
PubChem CID:	11042149
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713398]
NPO21404	Anagallis monelli	Species	Primulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17329877]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791473]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21404	Anagallis monelli	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20329	Gymnacranthera paniculata	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27877	Eliokarmos thyrsoides	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15866	Goniothalamus amuyon	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

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4162	Cell Line	NUGC	Homo sapiens	IC50	=	32.1	ug.mL-1	PMID[503793]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	36.3	ug.mL-1	PMID[503793]

☑ 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 NPC98911 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	256
0.1-0.2	1311
0.2-0.3	3794
0.3-0.4	11064
0.4-0.5	11117
0.5-0.6	12579
0.6-0.7	2296
0.7-0.8	249
0.8-0.85	17
0.85-0.9	11
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472318
0.9583	High Similarity	NPC85977
0.9278	High Similarity	NPC234305
0.9	High Similarity	NPC472316
0.9	High Similarity	NPC474376
0.9	High Similarity	NPC475203
0.9	High Similarity	NPC472315
0.899	High Similarity	NPC242913
0.899	High Similarity	NPC171831
0.899	High Similarity	NPC280616
0.8911	High Similarity	NPC277788
0.8812	High Similarity	NPC37115
0.8812	High Similarity	NPC136962
0.871	High Similarity	NPC304760
0.8646	High Similarity	NPC23453
0.8632	High Similarity	NPC119631
0.8617	High Similarity	NPC173443
0.8585	High Similarity	NPC308744
0.8491	Intermediate Similarity	NPC265002
0.8396	Intermediate Similarity	NPC234376
0.8387	Intermediate Similarity	NPC58616
0.837	Intermediate Similarity	NPC324835
0.837	Intermediate Similarity	NPC127491
0.837	Intermediate Similarity	NPC308619
0.8333	Intermediate Similarity	NPC213156
0.8333	Intermediate Similarity	NPC240108
0.8257	Intermediate Similarity	NPC473507
0.8224	Intermediate Similarity	NPC185840
0.8211	Intermediate Similarity	NPC96625
0.8211	Intermediate Similarity	NPC169050
0.8211	Intermediate Similarity	NPC286608
0.8211	Intermediate Similarity	NPC89377
0.819	Intermediate Similarity	NPC472314
0.819	Intermediate Similarity	NPC475465
0.8155	Intermediate Similarity	NPC82426
0.8155	Intermediate Similarity	NPC91820
0.8137	Intermediate Similarity	NPC42211
0.8131	Intermediate Similarity	NPC474157
0.8061	Intermediate Similarity	NPC472319
0.8056	Intermediate Similarity	NPC158282
0.8041	Intermediate Similarity	NPC220893
0.8039	Intermediate Similarity	NPC118343
0.802	Intermediate Similarity	NPC249912
0.802	Intermediate Similarity	NPC325499
0.802	Intermediate Similarity	NPC276775
0.802	Intermediate Similarity	NPC92754
0.8	Intermediate Similarity	NPC269457
0.8	Intermediate Similarity	NPC5472
0.8	Intermediate Similarity	NPC472919
0.7982	Intermediate Similarity	NPC474176
0.7957	Intermediate Similarity	NPC89950
0.7944	Intermediate Similarity	NPC83628
0.7944	Intermediate Similarity	NPC474364
0.7944	Intermediate Similarity	NPC469636
0.7944	Intermediate Similarity	NPC265407
0.7941	Intermediate Similarity	NPC225060
0.7941	Intermediate Similarity	NPC35448
0.7941	Intermediate Similarity	NPC78701
0.7905	Intermediate Similarity	NPC114594
0.7864	Intermediate Similarity	NPC146351
0.783	Intermediate Similarity	NPC209632
0.7826	Intermediate Similarity	NPC176228
0.7822	Intermediate Similarity	NPC130398
0.7818	Intermediate Similarity	NPC128368
0.7818	Intermediate Similarity	NPC272524
0.781	Intermediate Similarity	NPC301943
0.781	Intermediate Similarity	NPC474365
0.781	Intermediate Similarity	NPC60679
0.78	Intermediate Similarity	NPC77273
0.7798	Intermediate Similarity	NPC210089
0.7788	Intermediate Similarity	NPC70624
0.7778	Intermediate Similarity	NPC185501
0.7768	Intermediate Similarity	NPC149691
0.7766	Intermediate Similarity	NPC165212
0.7766	Intermediate Similarity	NPC71795
0.7748	Intermediate Similarity	NPC172525
0.7742	Intermediate Similarity	NPC78517
0.7742	Intermediate Similarity	NPC170484
0.7742	Intermediate Similarity	NPC167577
0.7727	Intermediate Similarity	NPC474314
0.7706	Intermediate Similarity	NPC174099
0.7706	Intermediate Similarity	NPC149545
0.7706	Intermediate Similarity	NPC273837
0.7692	Intermediate Similarity	NPC325497
0.7684	Intermediate Similarity	NPC99240
0.7679	Intermediate Similarity	NPC474685
0.767	Intermediate Similarity	NPC270654
0.766	Intermediate Similarity	NPC121800
0.7642	Intermediate Similarity	NPC179686
0.7642	Intermediate Similarity	NPC89886
0.7636	Intermediate Similarity	NPC167504
0.7632	Intermediate Similarity	NPC469574
0.7629	Intermediate Similarity	NPC475710
0.7615	Intermediate Similarity	NPC206341
0.7615	Intermediate Similarity	NPC99846
0.7615	Intermediate Similarity	NPC40178
0.7615	Intermediate Similarity	NPC269023
0.7604	Intermediate Similarity	NPC208183
0.7604	Intermediate Similarity	NPC243289
0.7593	Intermediate Similarity	NPC119271
0.7593	Intermediate Similarity	NPC477251
0.7589	Intermediate Similarity	NPC474363
0.7589	Intermediate Similarity	NPC307651
0.7579	Intermediate Similarity	NPC303245
0.757	Intermediate Similarity	NPC109637
0.7568	Intermediate Similarity	NPC79496
0.7547	Intermediate Similarity	NPC188895
0.7544	Intermediate Similarity	NPC190298
0.7527	Intermediate Similarity	NPC287790
0.7527	Intermediate Similarity	NPC3672
0.7524	Intermediate Similarity	NPC203925
0.7523	Intermediate Similarity	NPC20485
0.7523	Intermediate Similarity	NPC47536
0.7523	Intermediate Similarity	NPC56493
0.7522	Intermediate Similarity	NPC210092
0.75	Intermediate Similarity	NPC323103
0.75	Intermediate Similarity	NPC161611
0.75	Intermediate Similarity	NPC106313
0.75	Intermediate Similarity	NPC139891
0.75	Intermediate Similarity	NPC128730
0.75	Intermediate Similarity	NPC103387
0.7479	Intermediate Similarity	NPC471466
0.7477	Intermediate Similarity	NPC160382
0.7477	Intermediate Similarity	NPC183700
0.7477	Intermediate Similarity	NPC304638
0.7477	Intermediate Similarity	NPC476003
0.7456	Intermediate Similarity	NPC476476
0.7456	Intermediate Similarity	NPC100353
0.7455	Intermediate Similarity	NPC10251
0.7455	Intermediate Similarity	NPC17417
0.7449	Intermediate Similarity	NPC53299
0.7434	Intermediate Similarity	NPC87069
0.7431	Intermediate Similarity	NPC176971
0.7431	Intermediate Similarity	NPC326447
0.7431	Intermediate Similarity	NPC37622
0.7431	Intermediate Similarity	NPC30594
0.7429	Intermediate Similarity	NPC154517
0.7423	Intermediate Similarity	NPC270507
0.7419	Intermediate Similarity	NPC175393
0.7417	Intermediate Similarity	NPC125053
0.7411	Intermediate Similarity	NPC139946
0.7411	Intermediate Similarity	NPC270699
0.7411	Intermediate Similarity	NPC82899
0.7407	Intermediate Similarity	NPC31786
0.7407	Intermediate Similarity	NPC269644
0.7387	Intermediate Similarity	NPC93084
0.7387	Intermediate Similarity	NPC214067
0.7387	Intermediate Similarity	NPC251854
0.7387	Intermediate Similarity	NPC196246
0.7383	Intermediate Similarity	NPC45613
0.7383	Intermediate Similarity	NPC154905
0.7383	Intermediate Similarity	NPC60373
0.7373	Intermediate Similarity	NPC50872
0.7373	Intermediate Similarity	NPC229600
0.7368	Intermediate Similarity	NPC306740
0.7364	Intermediate Similarity	NPC151530
0.7364	Intermediate Similarity	NPC157473
0.7364	Intermediate Similarity	NPC260952
0.7358	Intermediate Similarity	NPC80115
0.7355	Intermediate Similarity	NPC476033
0.7355	Intermediate Similarity	NPC85830
0.7345	Intermediate Similarity	NPC266116
0.7339	Intermediate Similarity	NPC127676
0.7339	Intermediate Similarity	NPC227255
0.7339	Intermediate Similarity	NPC473855
0.7339	Intermediate Similarity	NPC152384
0.7339	Intermediate Similarity	NPC37714
0.7321	Intermediate Similarity	NPC323007
0.7321	Intermediate Similarity	NPC1082
0.7321	Intermediate Similarity	NPC305912
0.7321	Intermediate Similarity	NPC473809
0.7321	Intermediate Similarity	NPC260818
0.7321	Intermediate Similarity	NPC243355
0.7317	Intermediate Similarity	NPC199204
0.7304	Intermediate Similarity	NPC216387
0.7304	Intermediate Similarity	NPC471616
0.7297	Intermediate Similarity	NPC182549
0.7297	Intermediate Similarity	NPC114741
0.7297	Intermediate Similarity	NPC281604
0.7297	Intermediate Similarity	NPC184633
0.7295	Intermediate Similarity	NPC329272
0.729	Intermediate Similarity	NPC253746
0.7288	Intermediate Similarity	NPC473243
0.7281	Intermediate Similarity	NPC477411
0.7281	Intermediate Similarity	NPC196075
0.7273	Intermediate Similarity	NPC294134
0.7264	Intermediate Similarity	NPC160548
0.7264	Intermediate Similarity	NPC175852
0.7264	Intermediate Similarity	NPC135951
0.7264	Intermediate Similarity	NPC210529
0.7257	Intermediate Similarity	NPC321852
0.7257	Intermediate Similarity	NPC477250
0.725	Intermediate Similarity	NPC325301
0.725	Intermediate Similarity	NPC475692
0.725	Intermediate Similarity	NPC474283
0.7248	Intermediate Similarity	NPC148060
0.7248	Intermediate Similarity	NPC2518
0.7241	Intermediate Similarity	NPC128633
0.7232	Intermediate Similarity	NPC75272
0.7232	Intermediate Similarity	NPC471954

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 NPC98911 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	873
0.2-0.3	1438
0.3-0.4	3130
0.4-0.5	2106
0.5-0.6	1108
0.6-0.7	233
0.7-0.8	14
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
0.8211	Intermediate Similarity	NPD1282	Approved
0.8039	Intermediate Similarity	NPD1238	Approved
0.7798	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD969	Suspended
0.7685	Intermediate Similarity	NPD1358	Approved
0.7545	Intermediate Similarity	NPD2067	Discontinued
0.75	Intermediate Similarity	NPD9697	Approved
0.7455	Intermediate Similarity	NPD2182	Approved
0.7431	Intermediate Similarity	NPD3134	Approved
0.7407	Intermediate Similarity	NPD164	Approved
0.7391	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD4198	Discontinued
0.7264	Intermediate Similarity	NPD5926	Approved
0.7264	Intermediate Similarity	NPD9495	Approved
0.7212	Intermediate Similarity	NPD1202	Approved
0.72	Intermediate Similarity	NPD9257	Approved
0.72	Intermediate Similarity	NPD9259	Approved
0.713	Intermediate Similarity	NPD2558	Approved
0.713	Intermediate Similarity	NPD2552	Approved
0.713	Intermediate Similarity	NPD2555	Approved
0.713	Intermediate Similarity	NPD2550	Approved
0.713	Intermediate Similarity	NPD2549	Approved
0.713	Intermediate Similarity	NPD2553	Approved
0.7105	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1237	Approved
0.7091	Intermediate Similarity	NPD5909	Discontinued
0.708	Intermediate Similarity	NPD5239	Approved
0.708	Intermediate Similarity	NPD5240	Approved
0.708	Intermediate Similarity	NPD5236	Approved
0.708	Intermediate Similarity	NPD5235	Approved
0.708	Intermediate Similarity	NPD5237	Approved
0.7069	Intermediate Similarity	NPD2629	Approved
0.7064	Intermediate Similarity	NPD4189	Approved
0.7064	Intermediate Similarity	NPD4188	Approved
0.7037	Intermediate Similarity	NPD7798	Approved
0.7018	Intermediate Similarity	NPD2201	Approved
0.7	Intermediate Similarity	NPD6647	Phase 2
0.699	Remote Similarity	NPD689	Discontinued
0.6983	Remote Similarity	NPD1241	Discontinued
0.6947	Remote Similarity	NPD9716	Approved
0.6937	Remote Similarity	NPD3047	Approved
0.6937	Remote Similarity	NPD3048	Approved
0.6937	Remote Similarity	NPD3046	Approved
0.6923	Remote Similarity	NPD9258	Approved
0.6923	Remote Similarity	NPD9256	Approved
0.6917	Remote Similarity	NPD5691	Approved
0.6916	Remote Similarity	NPD1989	Approved
0.6903	Remote Similarity	NPD290	Approved
0.6897	Remote Similarity	NPD5535	Approved
0.6885	Remote Similarity	NPD6287	Discontinued
0.6855	Remote Similarity	NPD5667	Approved
0.685	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2684	Approved
0.6837	Remote Similarity	NPD9490	Approved
0.6833	Remote Similarity	NPD9545	Approved
0.6814	Remote Similarity	NPD3524	Approved
0.6814	Remote Similarity	NPD2559	Approved
0.6814	Remote Similarity	NPD2551	Approved
0.6814	Remote Similarity	NPD3526	Approved
0.6807	Remote Similarity	NPD9493	Approved
0.6804	Remote Similarity	NPD9294	Approved
0.6762	Remote Similarity	NPD3672	Approved
0.6762	Remote Similarity	NPD3673	Approved
0.6748	Remote Similarity	NPD422	Phase 1
0.6748	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD225	Approved
0.6735	Remote Similarity	NPD227	Approved
0.6733	Remote Similarity	NPD9491	Approved
0.6727	Remote Similarity	NPD2066	Phase 3
0.6721	Remote Similarity	NPD5126	Approved
0.6721	Remote Similarity	NPD5125	Phase 3
0.672	Remote Similarity	NPD2198	Approved
0.672	Remote Similarity	NPD2199	Approved
0.6696	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD812	Approved
0.6667	Remote Similarity	NPD9260	Approved
0.6667	Remote Similarity	NPD5705	Approved
0.6667	Remote Similarity	NPD5706	Approved
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD5704	Approved
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD811	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD810	Approved
0.6641	Remote Similarity	NPD6832	Phase 2
0.6639	Remote Similarity	NPD5585	Approved
0.6638	Remote Similarity	NPD9713	Approved
0.6635	Remote Similarity	NPD1087	Approved
0.6614	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7843	Approved
0.6589	Remote Similarity	NPD7008	Discontinued
0.6585	Remote Similarity	NPD5305	Approved
0.6585	Remote Similarity	NPD5306	Approved
0.6585	Remote Similarity	NPD4626	Approved
0.6579	Remote Similarity	NPD5048	Discontinued
0.6579	Remote Similarity	NPD794	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD531	Approved
0.6569	Remote Similarity	NPD3971	Phase 1
0.6555	Remote Similarity	NPD6010	Discontinued
0.6549	Remote Similarity	NPD1929	Approved
0.6549	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD9261	Approved
0.6549	Remote Similarity	NPD1930	Approved
0.6549	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD1239	Approved
0.6541	Remote Similarity	NPD2567	Approved
0.6541	Remote Similarity	NPD2569	Approved
0.6538	Remote Similarity	NPD6798	Discontinued
0.6535	Remote Similarity	NPD226	Approved
0.6535	Remote Similarity	NPD9250	Approved
0.6532	Remote Similarity	NPD4106	Approved
0.6532	Remote Similarity	NPD4135	Approved
0.6532	Remote Similarity	NPD4136	Approved
0.6529	Remote Similarity	NPD5291	Approved
0.6529	Remote Similarity	NPD5292	Approved
0.6525	Remote Similarity	NPD4572	Approved
0.6525	Remote Similarity	NPD4573	Approved
0.6525	Remote Similarity	NPD4571	Approved
0.6522	Remote Similarity	NPD968	Approved
0.6515	Remote Similarity	NPD4340	Discontinued
0.6509	Remote Similarity	NPD800	Approved
0.65	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD550	Approved
0.6496	Remote Similarity	NPD551	Approved
0.6489	Remote Similarity	NPD6233	Phase 2
0.6484	Remote Similarity	NPD1019	Discontinued
0.648	Remote Similarity	NPD4480	Approved
0.648	Remote Similarity	NPD4806	Approved
0.648	Remote Similarity	NPD4807	Approved
0.6475	Remote Similarity	NPD5536	Phase 2
0.6475	Remote Similarity	NPD2347	Approved
0.6471	Remote Similarity	NPD2497	Approved
0.6471	Remote Similarity	NPD2496	Approved
0.6466	Remote Similarity	NPD9532	Phase 3
0.6457	Remote Similarity	NPD3225	Approved
0.6452	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD17	Approved
0.6449	Remote Similarity	NPD1090	Approved
0.6449	Remote Similarity	NPD1086	Approved
0.6449	Remote Similarity	NPD1089	Approved
0.6446	Remote Similarity	NPD7157	Approved
0.6442	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD4307	Phase 2
0.6429	Remote Similarity	NPD6637	Approved
0.6429	Remote Similarity	NPD9717	Approved
0.6429	Remote Similarity	NPD1877	Discontinued
0.6423	Remote Similarity	NPD7741	Discontinued
0.6423	Remote Similarity	NPD1652	Phase 2
0.6422	Remote Similarity	NPD1563	Approved
0.6417	Remote Similarity	NPD5283	Phase 1
0.6412	Remote Similarity	NPD3268	Approved
0.6412	Remote Similarity	NPD2313	Discontinued
0.6412	Remote Similarity	NPD1296	Phase 2
0.6406	Remote Similarity	NPD987	Approved
0.6406	Remote Similarity	NPD1203	Approved
0.64	Remote Similarity	NPD3847	Discontinued
0.6397	Remote Similarity	NPD7266	Discontinued
0.6391	Remote Similarity	NPD1933	Approved
0.6391	Remote Similarity	NPD5124	Phase 1
0.6391	Remote Similarity	NPD6355	Discontinued
0.6391	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6685	Approved
0.6378	Remote Similarity	NPD7876	Discontinued
0.6378	Remote Similarity	NPD4359	Approved
0.6377	Remote Similarity	NPD4628	Phase 3
0.6371	Remote Similarity	NPD4105	Approved
0.6371	Remote Similarity	NPD4102	Approved
0.6364	Remote Similarity	NPD4062	Phase 3
0.6364	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1693	Approved
0.6364	Remote Similarity	NPD5951	Approved
0.6356	Remote Similarity	NPD4234	Approved
0.6356	Remote Similarity	NPD5451	Approved
0.6356	Remote Similarity	NPD4233	Approved
0.6349	Remote Similarity	NPD1281	Approved
0.6349	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD1611	Approved
0.6349	Remote Similarity	NPD1091	Approved
0.6343	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD6039	Approved
0.6333	Remote Similarity	NPD7094	Approved
0.6333	Remote Similarity	NPD6858	Approved
0.6331	Remote Similarity	NPD3887	Approved
0.633	Remote Similarity	NPD1088	Approved
0.6325	Remote Similarity	NPD9267	Approved
0.6325	Remote Similarity	NPD9263	Approved
0.6325	Remote Similarity	NPD9264	Approved
0.6324	Remote Similarity	NPD2438	Suspended
0.6321	Remote Similarity	NPD4793	Discontinued
0.632	Remote Similarity	NPD6516	Phase 2
0.632	Remote Similarity	NPD1778	Approved
0.632	Remote Similarity	NPD5846	Approved
0.6316	Remote Similarity	NPD3373	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