NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.08
Volume:	270.459
LogP:	2.182
LogD:	1.9
LogS:	-3.173
# Rotatable Bonds:	4
TPSA:	65.13
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	3.849
Fsp3:	0.333
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:	-4.668
MDCK Permeability:	3.159827247145586e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.213

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	44.89703369140625%
Volume Distribution (VD):	0.779
Pgp-substrate:	67.97455596923828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.167
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.109
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	7.444
Half-life (T1/2):	0.699

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.267
Drug-inuced Liver Injury (DILI):	0.508
AMES Toxicity:	0.338
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.548
Skin Sensitization:	0.948
Carcinogencity:	0.416
Eye Corrosion:	0.956
Eye Irritation:	0.958
Respiratory Toxicity:	0.313

Download Data

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

Natural Product: NPC85977

Natural Product ID:	NPC85977
*Common Name:**	Cheliensisin A
IUPAC Name:	[(2R,3S)-6-oxo-2-[(2S,3R)-3-phenyloxiran-2-yl]-2,3-dihydropyran-3-yl] acetate
Synonyms:	Cheliensisin A
Standard InCHIKey:	AHZVYVPVHRHEHF-MYPMTAMASA-N
Standard InCHI:	InChI=1S/C15H14O5/c1-9(16)18-11-7-8-12(17)19-14(11)15-13(20-15)10-5-3-2-4-6-10/h2-8,11,13-15H,1H3/t11-,13+,14+,15-/m0/s1
SMILES:	CC(=O)O[C@H]1C=CC(=O)O[C@H]1[C@H]1O[C@@H]1c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1818734
PubChem CID:	56683717
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
NPO8674	Goniothalamus arvensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1970.0	nM	PMID[534511]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	4700.0	nM	PMID[534511]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5990.0	nM	PMID[534511]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	20310.0	nM	PMID[534511]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	25650.0	nM	PMID[534511]

☑ 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 NPC85977 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	247
0.1-0.2	1092
0.2-0.3	3098
0.3-0.4	9170
0.4-0.5	11031
0.5-0.6	13788
0.6-0.7	3895
0.7-0.8	347
0.8-0.85	16
0.85-0.9	9
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC472318
0.9583	High Similarity	NPC98911
0.949	High Similarity	NPC234305
0.902	High Similarity	NPC37115
0.902	High Similarity	NPC474376
0.902	High Similarity	NPC472315
0.902	High Similarity	NPC475203
0.902	High Similarity	NPC472316
0.8932	High Similarity	NPC277788
0.8835	High Similarity	NPC136962
0.8824	High Similarity	NPC280616
0.8824	High Similarity	NPC171831
0.8824	High Similarity	NPC242913
0.8692	High Similarity	NPC265002
0.8598	High Similarity	NPC234376
0.8542	High Similarity	NPC304760
0.8485	Intermediate Similarity	NPC23453
0.8455	Intermediate Similarity	NPC473507
0.8454	Intermediate Similarity	NPC173443
0.844	Intermediate Similarity	NPC308744
0.8426	Intermediate Similarity	NPC185840
0.8283	Intermediate Similarity	NPC119631
0.8229	Intermediate Similarity	NPC58616
0.8061	Intermediate Similarity	NPC169050
0.8061	Intermediate Similarity	NPC89377
0.8061	Intermediate Similarity	NPC96625
0.8061	Intermediate Similarity	NPC286608
0.8021	Intermediate Similarity	NPC308619
0.8021	Intermediate Similarity	NPC324835
0.8021	Intermediate Similarity	NPC127491
0.8019	Intermediate Similarity	NPC91820
0.8019	Intermediate Similarity	NPC82426
0.8	Intermediate Similarity	NPC240108
0.8	Intermediate Similarity	NPC474157
0.8	Intermediate Similarity	NPC213156
0.7982	Intermediate Similarity	NPC469636
0.7982	Intermediate Similarity	NPC474364
0.7965	Intermediate Similarity	NPC149691
0.7946	Intermediate Similarity	NPC307651
0.7909	Intermediate Similarity	NPC174099
0.79	Intermediate Similarity	NPC220893
0.789	Intermediate Similarity	NPC475465
0.789	Intermediate Similarity	NPC472314
0.7885	Intermediate Similarity	NPC325499
0.7885	Intermediate Similarity	NPC249912
0.7885	Intermediate Similarity	NPC276775
0.7885	Intermediate Similarity	NPC92754
0.787	Intermediate Similarity	NPC269457
0.787	Intermediate Similarity	NPC472919
0.7864	Intermediate Similarity	NPC5472
0.7857	Intermediate Similarity	NPC128368
0.7857	Intermediate Similarity	NPC474176
0.785	Intermediate Similarity	NPC301943
0.785	Intermediate Similarity	NPC474365
0.783	Intermediate Similarity	NPC42211
0.783	Intermediate Similarity	NPC70624
0.7818	Intermediate Similarity	NPC265407
0.7818	Intermediate Similarity	NPC83628
0.7812	Intermediate Similarity	NPC89950
0.781	Intermediate Similarity	NPC225060
0.781	Intermediate Similarity	NPC35448
0.781	Intermediate Similarity	NPC78701
0.7807	Intermediate Similarity	NPC476476
0.7798	Intermediate Similarity	NPC477251
0.7798	Intermediate Similarity	NPC119271
0.7788	Intermediate Similarity	NPC172525
0.7768	Intermediate Similarity	NPC158282
0.775	Intermediate Similarity	NPC125053
0.7745	Intermediate Similarity	NPC472319
0.7736	Intermediate Similarity	NPC118343
0.7736	Intermediate Similarity	NPC146351
0.7736	Intermediate Similarity	NPC203925
0.7727	Intermediate Similarity	NPC56493
0.7706	Intermediate Similarity	NPC209632
0.7699	Intermediate Similarity	NPC272524
0.7692	Intermediate Similarity	NPC130398
0.7679	Intermediate Similarity	NPC210089
0.7672	Intermediate Similarity	NPC469574
0.7667	Intermediate Similarity	NPC471466
0.7658	Intermediate Similarity	NPC17417
0.7658	Intermediate Similarity	NPC10251
0.7647	Intermediate Similarity	NPC185501
0.7642	Intermediate Similarity	NPC199204
0.7632	Intermediate Similarity	NPC474363
0.7623	Intermediate Similarity	NPC329272
0.7615	Intermediate Similarity	NPC114594
0.7615	Intermediate Similarity	NPC109637
0.7615	Intermediate Similarity	NPC31786
0.7611	Intermediate Similarity	NPC82899
0.7611	Intermediate Similarity	NPC270699
0.7611	Intermediate Similarity	NPC474314
0.7604	Intermediate Similarity	NPC170484
0.7604	Intermediate Similarity	NPC78517
0.7604	Intermediate Similarity	NPC167577
0.7593	Intermediate Similarity	NPC188895
0.7589	Intermediate Similarity	NPC196246
0.7589	Intermediate Similarity	NPC93084
0.7589	Intermediate Similarity	NPC251854
0.7589	Intermediate Similarity	NPC214067
0.7589	Intermediate Similarity	NPC273837
0.7586	Intermediate Similarity	NPC190298
0.7583	Intermediate Similarity	NPC325301
0.757	Intermediate Similarity	NPC325497
0.7565	Intermediate Similarity	NPC474685
0.7565	Intermediate Similarity	NPC210092
0.7563	Intermediate Similarity	NPC50872
0.7551	Intermediate Similarity	NPC99240
0.7551	Intermediate Similarity	NPC106313
0.7544	Intermediate Similarity	NPC161611
0.7541	Intermediate Similarity	NPC476033
0.7541	Intermediate Similarity	NPC85830
0.7526	Intermediate Similarity	NPC121800
0.7523	Intermediate Similarity	NPC60679
0.7523	Intermediate Similarity	NPC179686
0.7522	Intermediate Similarity	NPC260818
0.7522	Intermediate Similarity	NPC305912
0.7522	Intermediate Similarity	NPC1082
0.752	Intermediate Similarity	NPC80170
0.75	Intermediate Similarity	NPC469675
0.75	Intermediate Similarity	NPC99846
0.75	Intermediate Similarity	NPC176228
0.75	Intermediate Similarity	NPC40178
0.75	Intermediate Similarity	NPC475710
0.75	Intermediate Similarity	NPC77273
0.75	Intermediate Similarity	NPC269023
0.7479	Intermediate Similarity	NPC473243
0.7477	Intermediate Similarity	NPC154517
0.7456	Intermediate Similarity	NPC321852
0.7456	Intermediate Similarity	NPC477250
0.7449	Intermediate Similarity	NPC165212
0.7449	Intermediate Similarity	NPC71795
0.7449	Intermediate Similarity	NPC303245
0.7438	Intermediate Similarity	NPC327070
0.7434	Intermediate Similarity	NPC149545
0.7431	Intermediate Similarity	NPC154905
0.7431	Intermediate Similarity	NPC60373
0.7419	Intermediate Similarity	NPC473993
0.7417	Intermediate Similarity	NPC300827
0.7417	Intermediate Similarity	NPC473439
0.7417	Intermediate Similarity	NPC229600
0.7414	Intermediate Similarity	NPC87563
0.7414	Intermediate Similarity	NPC41851
0.7411	Intermediate Similarity	NPC20485
0.7411	Intermediate Similarity	NPC47536
0.7407	Intermediate Similarity	NPC80115
0.7398	Intermediate Similarity	NPC79608
0.7396	Intermediate Similarity	NPC287790
0.7396	Intermediate Similarity	NPC3672
0.7395	Intermediate Similarity	NPC98748
0.7387	Intermediate Similarity	NPC152384
0.7387	Intermediate Similarity	NPC37714
0.7387	Intermediate Similarity	NPC127676
0.7387	Intermediate Similarity	NPC128730
0.7385	Intermediate Similarity	NPC475195
0.7383	Intermediate Similarity	NPC270654
0.7381	Intermediate Similarity	NPC60825
0.7381	Intermediate Similarity	NPC291419
0.7381	Intermediate Similarity	NPC475478
0.7377	Intermediate Similarity	NPC138798
0.7374	Intermediate Similarity	NPC323103
0.7374	Intermediate Similarity	NPC103387
0.7368	Intermediate Similarity	NPC183700
0.7368	Intermediate Similarity	NPC323007
0.7368	Intermediate Similarity	NPC167504
0.7368	Intermediate Similarity	NPC476003
0.7364	Intermediate Similarity	NPC160382
0.7364	Intermediate Similarity	NPC304638
0.7364	Intermediate Similarity	NPC89886
0.7355	Intermediate Similarity	NPC475328
0.7355	Intermediate Similarity	NPC193484
0.735	Intermediate Similarity	NPC471616
0.735	Intermediate Similarity	NPC216387
0.7345	Intermediate Similarity	NPC85493
0.7345	Intermediate Similarity	NPC281604
0.7345	Intermediate Similarity	NPC182549
0.7345	Intermediate Similarity	NPC114741
0.7345	Intermediate Similarity	NPC206341
0.7345	Intermediate Similarity	NPC184633
0.7344	Intermediate Similarity	NPC167111
0.7344	Intermediate Similarity	NPC296624
0.7344	Intermediate Similarity	NPC318400
0.7344	Intermediate Similarity	NPC471910
0.7344	Intermediate Similarity	NPC133956
0.7344	Intermediate Similarity	NPC207002
0.7333	Intermediate Similarity	NPC328485
0.7328	Intermediate Similarity	NPC153053
0.7328	Intermediate Similarity	NPC87069
0.7327	Intermediate Similarity	NPC53299
0.7323	Intermediate Similarity	NPC238370
0.7321	Intermediate Similarity	NPC30594
0.7321	Intermediate Similarity	NPC37622
0.7321	Intermediate Similarity	NPC176971
0.7321	Intermediate Similarity	NPC326447
0.7317	Intermediate Similarity	NPC246166
0.7315	Intermediate Similarity	NPC135951
0.7311	Intermediate Similarity	NPC89324
0.7311	Intermediate Similarity	NPC309434
0.7311	Intermediate Similarity	NPC277460
0.7304	Intermediate Similarity	NPC79496
0.7304	Intermediate Similarity	NPC139946

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 NPC85977 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	801
0.2-0.3	1433
0.3-0.4	2958
0.4-0.5	2223
0.5-0.6	1252
0.6-0.7	260
0.7-0.8	16
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
0.8061	Intermediate Similarity	NPD1282	Approved
0.7768	Intermediate Similarity	NPD969	Suspended
0.7748	Intermediate Similarity	NPD2067	Discontinued
0.7736	Intermediate Similarity	NPD1238	Approved
0.7727	Intermediate Similarity	NPD1358	Approved
0.7679	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2182	Approved
0.7615	Intermediate Similarity	NPD164	Approved
0.75	Intermediate Similarity	NPD4198	Discontinued
0.7436	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3134	Approved
0.7232	Intermediate Similarity	NPD9697	Approved
0.7156	Intermediate Similarity	NPD5926	Approved
0.7119	Intermediate Similarity	NPD2629	Approved
0.7103	Intermediate Similarity	NPD1202	Approved
0.7091	Intermediate Similarity	NPD7798	Approved
0.7073	Intermediate Similarity	NPD6287	Discontinued
0.7054	Intermediate Similarity	NPD6647	Phase 2
0.7049	Intermediate Similarity	NPD5125	Phase 3
0.7049	Intermediate Similarity	NPD5126	Approved
0.7031	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2552	Approved
0.7027	Intermediate Similarity	NPD2549	Approved
0.7027	Intermediate Similarity	NPD2553	Approved
0.7027	Intermediate Similarity	NPD2558	Approved
0.7027	Intermediate Similarity	NPD2555	Approved
0.7027	Intermediate Similarity	NPD2550	Approved
0.7009	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9495	Approved
0.6992	Remote Similarity	NPD3496	Discontinued
0.6991	Remote Similarity	NPD5909	Discontinued
0.6983	Remote Similarity	NPD5240	Approved
0.6983	Remote Similarity	NPD5237	Approved
0.6983	Remote Similarity	NPD5235	Approved
0.6983	Remote Similarity	NPD5236	Approved
0.6983	Remote Similarity	NPD5239	Approved
0.6967	Remote Similarity	NPD5691	Approved
0.6964	Remote Similarity	NPD4189	Approved
0.6964	Remote Similarity	NPD4188	Approved
0.6949	Remote Similarity	NPD5535	Approved
0.6923	Remote Similarity	NPD9257	Approved
0.6923	Remote Similarity	NPD2201	Approved
0.6923	Remote Similarity	NPD9259	Approved
0.6891	Remote Similarity	NPD1241	Discontinued
0.6842	Remote Similarity	NPD3047	Approved
0.6842	Remote Similarity	NPD3046	Approved
0.6842	Remote Similarity	NPD3048	Approved
0.6842	Remote Similarity	NPD1237	Approved
0.6829	Remote Similarity	NPD5585	Approved
0.6818	Remote Similarity	NPD1989	Approved
0.681	Remote Similarity	NPD290	Approved
0.6786	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5667	Approved
0.6769	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2684	Approved
0.6748	Remote Similarity	NPD9545	Approved
0.6729	Remote Similarity	NPD689	Discontinued
0.6724	Remote Similarity	NPD3524	Approved
0.6724	Remote Similarity	NPD6685	Approved
0.6724	Remote Similarity	NPD2551	Approved
0.6724	Remote Similarity	NPD2559	Approved
0.6724	Remote Similarity	NPD3526	Approved
0.6721	Remote Similarity	NPD9493	Approved
0.6719	Remote Similarity	NPD3266	Approved
0.6719	Remote Similarity	NPD3267	Approved
0.6692	Remote Similarity	NPD6832	Phase 2
0.6691	Remote Similarity	NPD7266	Discontinued
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1019	Discontinued
0.6667	Remote Similarity	NPD9258	Approved
0.6667	Remote Similarity	NPD9256	Approved
0.6667	Remote Similarity	NPD1611	Approved
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD3672	Approved
0.6667	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD7843	Approved
0.6667	Remote Similarity	NPD9716	Approved
0.6667	Remote Similarity	NPD5536	Phase 2
0.6641	Remote Similarity	NPD2199	Approved
0.6641	Remote Similarity	NPD2198	Approved
0.6641	Remote Similarity	NPD7008	Discontinued
0.664	Remote Similarity	NPD4626	Approved
0.6639	Remote Similarity	NPD7157	Approved
0.6638	Remote Similarity	NPD5048	Discontinued
0.6637	Remote Similarity	NPD2066	Phase 3
0.6636	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD225	Approved
0.6634	Remote Similarity	NPD227	Approved
0.6617	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD4307	Phase 2
0.6614	Remote Similarity	NPD6637	Approved
0.6613	Remote Similarity	NPD7741	Discontinued
0.6612	Remote Similarity	NPD5283	Phase 1
0.6609	Remote Similarity	NPD1930	Approved
0.6609	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1929	Approved
0.6594	Remote Similarity	NPD1652	Phase 2
0.6593	Remote Similarity	NPD2567	Approved
0.6593	Remote Similarity	NPD2569	Approved
0.6591	Remote Similarity	NPD6798	Discontinued
0.6591	Remote Similarity	NPD2313	Discontinued
0.6589	Remote Similarity	NPD2797	Approved
0.6581	Remote Similarity	NPD812	Approved
0.6581	Remote Similarity	NPD5704	Approved
0.6581	Remote Similarity	NPD811	Approved
0.6581	Remote Similarity	NPD5706	Approved
0.6581	Remote Similarity	NPD5705	Approved
0.6581	Remote Similarity	NPD810	Approved
0.6569	Remote Similarity	NPD9490	Approved
0.6567	Remote Similarity	NPD6355	Discontinued
0.6567	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4359	Approved
0.6562	Remote Similarity	NPD7876	Discontinued
0.6547	Remote Similarity	NPD4628	Phase 3
0.6542	Remote Similarity	NPD1087	Approved
0.6535	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4480	Approved
0.6535	Remote Similarity	NPD9294	Approved
0.6532	Remote Similarity	NPD2347	Approved
0.6519	Remote Similarity	NPD6653	Approved
0.6508	Remote Similarity	NPD17	Approved
0.6508	Remote Similarity	NPD5306	Approved
0.6508	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5305	Approved
0.6496	Remote Similarity	NPD2438	Suspended
0.6496	Remote Similarity	NPD6032	Approved
0.6493	Remote Similarity	NPD4060	Phase 1
0.6484	Remote Similarity	NPD9717	Approved
0.6484	Remote Similarity	NPD1877	Discontinued
0.6481	Remote Similarity	NPD531	Approved
0.648	Remote Similarity	NPD1894	Discontinued
0.6476	Remote Similarity	NPD9491	Approved
0.6476	Remote Similarity	NPD3971	Phase 1
0.6475	Remote Similarity	NPD6010	Discontinued
0.6471	Remote Similarity	NPD7097	Phase 1
0.6466	Remote Similarity	NPD5765	Approved
0.6466	Remote Similarity	NPD3268	Approved
0.6462	Remote Similarity	NPD987	Approved
0.6457	Remote Similarity	NPD4106	Approved
0.6457	Remote Similarity	NPD3847	Discontinued
0.6457	Remote Similarity	NPD4136	Approved
0.6457	Remote Similarity	NPD4135	Approved
0.6454	Remote Similarity	NPD7236	Approved
0.6452	Remote Similarity	NPD5291	Approved
0.6452	Remote Similarity	NPD5292	Approved
0.6446	Remote Similarity	NPD4572	Approved
0.6446	Remote Similarity	NPD4573	Approved
0.6446	Remote Similarity	NPD4571	Approved
0.6444	Remote Similarity	NPD5124	Phase 1
0.6444	Remote Similarity	NPD230	Phase 1
0.6444	Remote Similarity	NPD1933	Approved
0.6444	Remote Similarity	NPD447	Suspended
0.6444	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4340	Discontinued
0.6442	Remote Similarity	NPD226	Approved
0.6441	Remote Similarity	NPD968	Approved
0.6439	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD9260	Approved
0.6423	Remote Similarity	NPD5951	Approved
0.6423	Remote Similarity	NPD4308	Phase 3
0.6422	Remote Similarity	NPD800	Approved
0.6418	Remote Similarity	NPD4062	Phase 3
0.6418	Remote Similarity	NPD4870	Approved
0.6417	Remote Similarity	NPD550	Approved
0.6417	Remote Similarity	NPD9713	Approved
0.6417	Remote Similarity	NPD551	Approved
0.6412	Remote Similarity	NPD6085	Phase 2
0.6412	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4807	Approved
0.6406	Remote Similarity	NPD4806	Approved
0.6406	Remote Similarity	NPD1281	Approved
0.6406	Remote Similarity	NPD1091	Approved
0.6403	Remote Similarity	NPD2424	Discontinued
0.6397	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6858	Approved
0.6393	Remote Similarity	NPD7094	Approved
0.6393	Remote Similarity	NPD2496	Approved
0.6393	Remote Similarity	NPD2497	Approved
0.6391	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD7095	Approved
0.6385	Remote Similarity	NPD3225	Approved
0.6383	Remote Similarity	NPD3887	Approved
0.6378	Remote Similarity	NPD1778	Approved
0.6377	Remote Similarity	NPD2935	Discontinued
0.637	Remote Similarity	NPD2979	Phase 3
0.6364	Remote Similarity	NPD1090	Approved
0.6364	Remote Similarity	NPD1089	Approved
0.6364	Remote Similarity	NPD1086	Approved
0.6357	Remote Similarity	NPD1608	Approved
0.6356	Remote Similarity	NPD794	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD1048	Approved
0.6343	Remote Similarity	NPD1296	Phase 2
0.6343	Remote Similarity	NPD3764	Approved
0.6339	Remote Similarity	NPD1563	Approved
0.6336	Remote Similarity	NPD1203	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