NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	214.06
Volume:	224.207
LogP:	2.192
LogD:	2.229
LogS:	-2.683
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.676
Synthetic Accessibility Score:	3.143
Fsp3:	0.154
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:	-4.694
MDCK Permeability:	1.9686369341798127e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.146
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.724
Plasma Protein Binding (PPB):	94.0644302368164%
Volume Distribution (VD):	0.566
Pgp-substrate:	3.968451976776123%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.638
CYP2C19-inhibitor:	0.876
CYP2C19-substrate:	0.44
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.798
CYP3A4-inhibitor:	0.075
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	4.928
Half-life (T1/2):	0.395

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.737
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.199
Rat Oral Acute Toxicity:	0.572
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.843
Carcinogencity:	0.65
Eye Corrosion:	0.56
Eye Irritation:	0.971
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC474685

Natural Product ID:	NPC474685
*Common Name:**	3'-Hydroxycorfin
IUPAC Name:	3-(3-hydroxybut-1-ynyl)isochromen-1-one
Synonyms:	3'-Hydroxycorfin
Standard InCHIKey:	XNVUGJDBKZLVPX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10O3/c1-9(14)6-7-11-8-10-4-2-3-5-12(10)13(15)16-11/h2-5,8-9,14H,1H3
SMILES:	CC(C#CC1=CC2=CC=CC=C2C(=O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479329
PubChem CID:	11229631
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001890] Isocoumarins and derivatives

*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
NPO24016	Cladanthus mixtus	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14738379]
NPO24016	Cladanthus mixtus	Species	Asteraceae	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
EC50	1
MIC	2

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	=	100.0	ug	PMID[560245]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	50.0	ug.mL-1	PMID[560245]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	0.9	ug.mL-1	PMID[560245]

☑ 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 NPC474685 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	287
0.1-0.2	1514
0.2-0.3	4131
0.3-0.4	10235
0.4-0.5	8943
0.5-0.6	6052
0.6-0.7	9201
0.7-0.8	2250
0.8-0.85	71
0.85-0.9	5
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9626	High Similarity	NPC272524
0.9434	High Similarity	NPC269023
0.9434	High Similarity	NPC99846
0.9273	High Similarity	NPC210092
0.9259	High Similarity	NPC474157
0.9151	High Similarity	NPC209632
0.9057	High Similarity	NPC114594
0.9009	High Similarity	NPC308744
0.8962	High Similarity	NPC60679
0.8909	High Similarity	NPC476003
0.8739	High Similarity	NPC243355
0.8727	High Similarity	NPC265407
0.8727	High Similarity	NPC83628
0.8716	High Similarity	NPC30594
0.8716	High Similarity	NPC37622
0.8684	High Similarity	NPC100353
0.8571	High Similarity	NPC260818
0.8571	High Similarity	NPC210089
0.8545	High Similarity	NPC119271
0.8522	High Similarity	NPC149691
0.8496	Intermediate Similarity	NPC158282
0.8496	Intermediate Similarity	NPC321852
0.8496	Intermediate Similarity	NPC474314
0.8491	Intermediate Similarity	NPC92754
0.8491	Intermediate Similarity	NPC249912
0.8491	Intermediate Similarity	NPC276775
0.8468	Intermediate Similarity	NPC56493
0.844	Intermediate Similarity	NPC89886
0.8435	Intermediate Similarity	NPC306740
0.8426	Intermediate Similarity	NPC42211
0.8411	Intermediate Similarity	NPC225060
0.8411	Intermediate Similarity	NPC78701
0.8411	Intermediate Similarity	NPC35448
0.8393	Intermediate Similarity	NPC10251
0.8393	Intermediate Similarity	NPC85493
0.8393	Intermediate Similarity	NPC474364
0.8393	Intermediate Similarity	NPC17417
0.8364	Intermediate Similarity	NPC31786
0.8348	Intermediate Similarity	NPC196075
0.8348	Intermediate Similarity	NPC153053
0.8348	Intermediate Similarity	NPC477411
0.8348	Intermediate Similarity	NPC307651
0.8333	Intermediate Similarity	NPC118343
0.8333	Intermediate Similarity	NPC146351
0.8319	Intermediate Similarity	NPC174099
0.8319	Intermediate Similarity	NPC93084
0.8319	Intermediate Similarity	NPC214067
0.8319	Intermediate Similarity	NPC196246
0.8319	Intermediate Similarity	NPC251854
0.8302	Intermediate Similarity	NPC130398
0.8273	Intermediate Similarity	NPC301943
0.8273	Intermediate Similarity	NPC474365
0.8264	Intermediate Similarity	NPC223351
0.8261	Intermediate Similarity	NPC128368
0.8257	Intermediate Similarity	NPC70624
0.8246	Intermediate Similarity	NPC305912
0.8246	Intermediate Similarity	NPC1082
0.8246	Intermediate Similarity	NPC167504
0.8241	Intermediate Similarity	NPC229242
0.823	Intermediate Similarity	NPC469636
0.8205	Intermediate Similarity	NPC226093
0.819	Intermediate Similarity	NPC237366
0.819	Intermediate Similarity	NPC474363
0.8182	Intermediate Similarity	NPC45613
0.8174	Intermediate Similarity	NPC82899
0.8174	Intermediate Similarity	NPC270699
0.8174	Intermediate Similarity	NPC79496
0.8174	Intermediate Similarity	NPC212415
0.8165	Intermediate Similarity	NPC325497
0.8142	Intermediate Similarity	NPC470391
0.813	Intermediate Similarity	NPC246166
0.8115	Intermediate Similarity	NPC46634
0.8103	Intermediate Similarity	NPC13784
0.8103	Intermediate Similarity	NPC161611
0.808	Intermediate Similarity	NPC181715
0.8049	Intermediate Similarity	NPC228739
0.8018	Intermediate Similarity	NPC188895
0.8	Intermediate Similarity	NPC203925
0.7984	Intermediate Similarity	NPC295664
0.7982	Intermediate Similarity	NPC211439
0.7966	Intermediate Similarity	NPC228936
0.7965	Intermediate Similarity	NPC269457
0.7946	Intermediate Similarity	NPC255676
0.7934	Intermediate Similarity	NPC204784
0.792	Intermediate Similarity	NPC275576
0.7899	Intermediate Similarity	NPC135730
0.7895	Intermediate Similarity	NPC472316
0.7895	Intermediate Similarity	NPC475203
0.7895	Intermediate Similarity	NPC474376
0.7895	Intermediate Similarity	NPC472315
0.7881	Intermediate Similarity	NPC87069
0.7869	Intermediate Similarity	NPC473243
0.7857	Intermediate Similarity	NPC169913
0.7857	Intermediate Similarity	NPC284477
0.784	Intermediate Similarity	NPC265910
0.784	Intermediate Similarity	NPC91475
0.783	Intermediate Similarity	NPC173443
0.7815	Intermediate Similarity	NPC474408
0.7805	Intermediate Similarity	NPC50872
0.7797	Intermediate Similarity	NPC474176
0.7788	Intermediate Similarity	NPC91820
0.7788	Intermediate Similarity	NPC82426
0.7788	Intermediate Similarity	NPC160382
0.7778	Intermediate Similarity	NPC291799
0.7769	Intermediate Similarity	NPC45104
0.7768	Intermediate Similarity	NPC282895
0.776	Intermediate Similarity	NPC471466
0.7759	Intermediate Similarity	NPC281604
0.7739	Intermediate Similarity	NPC136962
0.7736	Intermediate Similarity	NPC304760
0.7719	Intermediate Similarity	NPC171831
0.7719	Intermediate Similarity	NPC242913
0.7719	Intermediate Similarity	NPC280616
0.7719	Intermediate Similarity	NPC249067
0.7717	Intermediate Similarity	NPC470753
0.7717	Intermediate Similarity	NPC473220
0.771	Intermediate Similarity	NPC136608
0.771	Intermediate Similarity	NPC38420
0.7706	Intermediate Similarity	NPC23453
0.7705	Intermediate Similarity	NPC94637
0.7705	Intermediate Similarity	NPC94298
0.7705	Intermediate Similarity	NPC27633
0.7699	Intermediate Similarity	NPC25458
0.7699	Intermediate Similarity	NPC304873
0.7692	Intermediate Similarity	NPC273837
0.768	Intermediate Similarity	NPC217756
0.7679	Intermediate Similarity	NPC217621
0.7679	Intermediate Similarity	NPC472318
0.7679	Intermediate Similarity	NPC98911
0.7674	Intermediate Similarity	NPC82712
0.7672	Intermediate Similarity	NPC277788
0.7672	Intermediate Similarity	NPC20485
0.7667	Intermediate Similarity	NPC81808
0.7667	Intermediate Similarity	NPC470764
0.7667	Intermediate Similarity	NPC474095
0.7661	Intermediate Similarity	NPC144547
0.7658	Intermediate Similarity	NPC253423
0.7658	Intermediate Similarity	NPC270654
0.7652	Intermediate Similarity	NPC105899
0.7642	Intermediate Similarity	NPC89377
0.7642	Intermediate Similarity	NPC328459
0.7642	Intermediate Similarity	NPC90522
0.7642	Intermediate Similarity	NPC96625
0.7638	Intermediate Similarity	NPC470765
0.7632	Intermediate Similarity	NPC234305
0.7623	Intermediate Similarity	NPC217423
0.7623	Intermediate Similarity	NPC240664
0.7615	Intermediate Similarity	NPC77273
0.7615	Intermediate Similarity	NPC72915
0.7611	Intermediate Similarity	NPC112552
0.7607	Intermediate Similarity	NPC40178
0.7607	Intermediate Similarity	NPC318327
0.7603	Intermediate Similarity	NPC471616
0.7593	Intermediate Similarity	NPC62765
0.7589	Intermediate Similarity	NPC160548
0.7589	Intermediate Similarity	NPC210529
0.7589	Intermediate Similarity	NPC175852
0.7586	Intermediate Similarity	NPC37115
0.7586	Intermediate Similarity	NPC477251
0.7581	Intermediate Similarity	NPC289432
0.7581	Intermediate Similarity	NPC233282
0.7581	Intermediate Similarity	NPC72977
0.7581	Intermediate Similarity	NPC988
0.7578	Intermediate Similarity	NPC472706
0.7578	Intermediate Similarity	NPC110211
0.7565	Intermediate Similarity	NPC85977
0.7563	Intermediate Similarity	NPC66208
0.7557	Intermediate Similarity	NPC214702
0.7557	Intermediate Similarity	NPC104854
0.7557	Intermediate Similarity	NPC470831
0.7547	Intermediate Similarity	NPC318107
0.7545	Intermediate Similarity	NPC261181
0.7542	Intermediate Similarity	NPC234639
0.7541	Intermediate Similarity	NPC190298
0.7541	Intermediate Similarity	NPC128825
0.7541	Intermediate Similarity	NPC131192
0.754	Intermediate Similarity	NPC472703
0.754	Intermediate Similarity	NPC65627
0.754	Intermediate Similarity	NPC69403
0.754	Intermediate Similarity	NPC291189
0.7523	Intermediate Similarity	NPC119631
0.7521	Intermediate Similarity	NPC186933
0.7521	Intermediate Similarity	NPC156648
0.7521	Intermediate Similarity	NPC47536
0.7519	Intermediate Similarity	NPC472707
0.7519	Intermediate Similarity	NPC474097
0.7519	Intermediate Similarity	NPC470841
0.75	Intermediate Similarity	NPC49938
0.75	Intermediate Similarity	NPC470160
0.75	Intermediate Similarity	NPC4164
0.75	Intermediate Similarity	NPC476599
0.75	Intermediate Similarity	NPC236405
0.75	Intermediate Similarity	NPC61779
0.75	Intermediate Similarity	NPC220893
0.7481	Intermediate Similarity	NPC475195
0.7481	Intermediate Similarity	NPC475478
0.7481	Intermediate Similarity	NPC473271
0.748	Intermediate Similarity	NPC469574
0.748	Intermediate Similarity	NPC228318
0.748	Intermediate Similarity	NPC45794

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 NPC474685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	974
0.2-0.3	1389
0.3-0.4	2618
0.4-0.5	2134
0.5-0.6	1262
0.6-0.7	420
0.7-0.8	87
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD2181	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD2182	Approved
0.8364	Intermediate Similarity	NPD164	Approved
0.8333	Intermediate Similarity	NPD1238	Approved
0.8174	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5909	Discontinued
0.7719	Intermediate Similarity	NPD1237	Approved
0.7705	Intermediate Similarity	NPD9545	Approved
0.7593	Intermediate Similarity	NPD9258	Approved
0.7593	Intermediate Similarity	NPD9256	Approved
0.7589	Intermediate Similarity	NPD9495	Approved
0.7547	Intermediate Similarity	NPD9257	Approved
0.7547	Intermediate Similarity	NPD9259	Approved
0.7545	Intermediate Similarity	NPD1202	Approved
0.7541	Intermediate Similarity	NPD9493	Approved
0.7538	Intermediate Similarity	NPD7008	Discontinued
0.7538	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1282	Approved
0.7458	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1241	Discontinued
0.7395	Intermediate Similarity	NPD2067	Discontinued
0.7377	Intermediate Similarity	NPD5951	Approved
0.7328	Intermediate Similarity	NPD1930	Approved
0.7328	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6647	Phase 2
0.7328	Intermediate Similarity	NPD1929	Approved
0.7266	Intermediate Similarity	NPD9717	Approved
0.7236	Intermediate Similarity	NPD2629	Approved
0.7218	Intermediate Similarity	NPD3764	Approved
0.7217	Intermediate Similarity	NPD2066	Phase 3
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.7188	Intermediate Similarity	NPD6287	Discontinued
0.7188	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2798	Approved
0.7154	Intermediate Similarity	NPD2198	Approved
0.7154	Intermediate Similarity	NPD2199	Approved
0.7154	Intermediate Similarity	NPD1283	Approved
0.7154	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD1894	Discontinued
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7133	Intermediate Similarity	NPD6273	Approved
0.7105	Intermediate Similarity	NPD1989	Approved
0.7103	Intermediate Similarity	NPD9491	Approved
0.7099	Intermediate Similarity	NPD2797	Approved
0.7099	Intermediate Similarity	NPD1203	Approved
0.709	Intermediate Similarity	NPD2313	Discontinued
0.7054	Intermediate Similarity	NPD1281	Approved
0.705	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2346	Discontinued
0.7049	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1019	Discontinued
0.7031	Intermediate Similarity	NPD5306	Approved
0.7031	Intermediate Similarity	NPD5305	Approved
0.7018	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD9260	Approved
0.7007	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD3972	Approved
0.7	Intermediate Similarity	NPD3134	Approved
0.6984	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1090	Approved
0.6964	Remote Similarity	NPD1089	Approved
0.6964	Remote Similarity	NPD1086	Approved
0.6949	Remote Similarity	NPD1932	Approved
0.6942	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1358	Approved
0.6942	Remote Similarity	NPD9267	Approved
0.6942	Remote Similarity	NPD9263	Approved
0.6942	Remote Similarity	NPD9264	Approved
0.693	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7236	Approved
0.6917	Remote Similarity	NPD9697	Approved
0.6906	Remote Similarity	NPD3748	Approved
0.6906	Remote Similarity	NPD2799	Discontinued
0.6906	Remote Similarity	NPD4308	Phase 3
0.6903	Remote Similarity	NPD1239	Approved
0.6901	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7003	Approved
0.6901	Remote Similarity	NPD3750	Approved
0.6899	Remote Similarity	NPD17	Approved
0.6891	Remote Similarity	NPD9261	Approved
0.6887	Remote Similarity	NPD9490	Approved
0.6885	Remote Similarity	NPD74	Approved
0.6885	Remote Similarity	NPD9266	Approved
0.6875	Remote Similarity	NPD800	Approved
0.6871	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1693	Approved
0.6861	Remote Similarity	NPD4307	Phase 2
0.6855	Remote Similarity	NPD969	Suspended
0.685	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD1087	Approved
0.6847	Remote Similarity	NPD650	Approved
0.6842	Remote Similarity	NPD1088	Approved
0.6842	Remote Similarity	NPD3266	Approved
0.6842	Remote Similarity	NPD3267	Approved
0.6838	Remote Similarity	NPD3268	Approved
0.6831	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5401	Approved
0.6822	Remote Similarity	NPD5691	Approved
0.6822	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3672	Approved
0.6814	Remote Similarity	NPD3673	Approved
0.6812	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6004	Phase 3
0.6809	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6005	Phase 3
0.6809	Remote Similarity	NPD6002	Phase 3
0.68	Remote Similarity	NPD5277	Phase 2
0.6772	Remote Similarity	NPD4198	Discontinued
0.6769	Remote Similarity	NPD4626	Approved
0.6767	Remote Similarity	NPD5667	Approved
0.6759	Remote Similarity	NPD226	Approved
0.6757	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1565	Approved
0.6752	Remote Similarity	NPD1566	Phase 3
0.6752	Remote Similarity	NPD1564	Approved
0.6748	Remote Similarity	NPD2329	Discontinued
0.6746	Remote Similarity	NPD6010	Discontinued
0.6742	Remote Similarity	NPD6637	Approved
0.6742	Remote Similarity	NPD1481	Phase 2
0.6739	Remote Similarity	NPD2979	Phase 3
0.6738	Remote Similarity	NPD4477	Approved
0.6738	Remote Similarity	NPD2935	Discontinued
0.6738	Remote Similarity	NPD1551	Phase 2
0.6738	Remote Similarity	NPD4476	Approved
0.6735	Remote Similarity	NPD5403	Approved
0.672	Remote Similarity	NPD9508	Approved
0.6718	Remote Similarity	NPD4136	Approved
0.6718	Remote Similarity	NPD4106	Approved
0.6718	Remote Similarity	NPD4135	Approved
0.6716	Remote Similarity	NPD552	Approved
0.6716	Remote Similarity	NPD9567	Approved
0.6716	Remote Similarity	NPD553	Approved
0.6715	Remote Similarity	NPD411	Approved
0.6715	Remote Similarity	NPD6798	Discontinued
0.6714	Remote Similarity	NPD2567	Approved
0.6714	Remote Similarity	NPD2569	Approved
0.6692	Remote Similarity	NPD5157	Phase 1
0.6692	Remote Similarity	NPD5159	Phase 2
0.6692	Remote Similarity	NPD1651	Approved
0.6692	Remote Similarity	NPD5585	Approved
0.6692	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD230	Phase 1
0.6691	Remote Similarity	NPD6355	Discontinued
0.6691	Remote Similarity	NPD447	Suspended
0.6691	Remote Similarity	NPD1933	Approved
0.6689	Remote Similarity	NPD7239	Suspended
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4807	Approved
0.6667	Remote Similarity	NPD4806	Approved
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD2347	Approved
0.6667	Remote Similarity	NPD7713	Phase 3
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD1535	Discovery
0.6644	Remote Similarity	NPD2649	Approved
0.6644	Remote Similarity	NPD6799	Approved
0.6644	Remote Similarity	NPD2651	Approved
0.6642	Remote Similarity	NPD6966	Discovery
0.6642	Remote Similarity	NPD6039	Approved
0.6641	Remote Similarity	NPD1778	Approved
0.6639	Remote Similarity	NPD5048	Discontinued
0.6638	Remote Similarity	NPD1563	Approved
0.6636	Remote Similarity	NPD227	Approved
0.6636	Remote Similarity	NPD225	Approved
0.6636	Remote Similarity	NPD3971	Phase 1
0.6621	Remote Similarity	NPD3887	Approved
0.662	Remote Similarity	NPD2796	Approved
0.662	Remote Similarity	NPD2438	Suspended
0.6619	Remote Similarity	NPD3142	Approved
0.6619	Remote Similarity	NPD3140	Approved
0.6619	Remote Similarity	NPD1240	Approved
0.6619	Remote Similarity	NPD3373	Approved
0.6618	Remote Similarity	NPD454	Approved
0.6618	Remote Similarity	NPD9494	Approved
0.6617	Remote Similarity	NPD1877	Discontinued
0.6617	Remote Similarity	NPD4878	Approved
0.6612	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7609	Phase 3
0.6594	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1164	Approved
0.6593	Remote Similarity	NPD2625	Approved
0.6593	Remote Similarity	NPD2160	Approved
0.6593	Remote Similarity	NPD2159	Approved
0.6593	Remote Similarity	NPD2626	Approved
0.6593	Remote Similarity	NPD2628	Approved
0.6593	Remote Similarity	NPD2627	Approved
0.6593	Remote Similarity	NPD6362	Approved
0.6591	Remote Similarity	NPD3847	Discontinued

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