NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.11
Volume:	246.776
LogP:	2.79
LogD:	2.78
LogS:	-3.642
# Rotatable Bonds:	4
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.813
Synthetic Accessibility Score:	2.895
Fsp3:	0.357
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:	-4.632
MDCK Permeability:	2.0162968212389387e-05
Pgp-inhibitor:	0.359
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.387
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.216
Plasma Protein Binding (PPB):	91.56354522705078%
Volume Distribution (VD):	0.719
Pgp-substrate:	6.130102157592773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.531
CYP2C19-substrate:	0.593
CYP2C9-inhibitor:	0.563
CYP2C9-substrate:	0.292
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.442
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.621

ADMET: Excretion

Clearance (CL):	4.884
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.508
Carcinogencity:	0.603
Eye Corrosion:	0.037
Eye Irritation:	0.787
Respiratory Toxicity:	0.088

Download Data

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

Natural Product: NPC474157

Natural Product ID:	NPC474157
*Common Name:**	(-)-(R)-2'-Methoxydihydroartemidin
IUPAC Name:	3-[(2R)-2-methoxybutyl]isochromen-1-one
Synonyms:
Standard InCHIKey:	JVPBEOSSMYEDID-LLVKDONJSA-N
Standard InCHI:	InChI=1S/C14H16O3/c1-3-11(16-2)9-12-8-10-6-4-5-7-13(10)14(15)17-12/h4-8,11H,3,9H2,1-2H3/t11-/m1/s1
SMILES:	CC[C@H](Cc1cc2ccccc2c(=O)o1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463082
PubChem CID:	44566647
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
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	leaves	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	dried aerial organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	dried aerial organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	roots and stolons	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	underground organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31815461]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21334	Artemisia dracunculus	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
MIC	1

Activity Type	# Activity
Organism	1

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[475413]

☑ 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 NPC474157 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	339
0.1-0.2	1601
0.2-0.3	4063
0.3-0.4	9358
0.4-0.5	9491
0.5-0.6	5490
0.6-0.7	8268
0.7-0.8	3717
0.8-0.85	323
0.85-0.9	38
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9528	High Similarity	NPC308744
0.951	High Similarity	NPC209632
0.9434	High Similarity	NPC272524
0.9412	High Similarity	NPC114594
0.9314	High Similarity	NPC60679
0.9259	High Similarity	NPC210092
0.9259	High Similarity	NPC474685
0.9238	High Similarity	NPC269023
0.9238	High Similarity	NPC99846
0.9057	High Similarity	NPC265407
0.9057	High Similarity	NPC83628
0.9048	High Similarity	NPC37622
0.9048	High Similarity	NPC30594
0.9	High Similarity	NPC149691
0.8962	High Similarity	NPC56493
0.8922	High Similarity	NPC78701
0.8922	High Similarity	NPC35448
0.8889	High Similarity	NPC210089
0.8879	High Similarity	NPC17417
0.8879	High Similarity	NPC10251
0.8868	High Similarity	NPC119271
0.8835	High Similarity	NPC146351
0.8824	High Similarity	NPC276775
0.8824	High Similarity	NPC92754
0.8824	High Similarity	NPC249912
0.8818	High Similarity	NPC307651
0.8796	High Similarity	NPC196246
0.8796	High Similarity	NPC93084
0.8796	High Similarity	NPC214067
0.8796	High Similarity	NPC174099
0.8796	High Similarity	NPC251854
0.8762	High Similarity	NPC301943
0.8762	High Similarity	NPC474365
0.8762	High Similarity	NPC89886
0.875	High Similarity	NPC42211
0.8738	High Similarity	NPC225060
0.8727	High Similarity	NPC128368
0.8716	High Similarity	NPC243355
0.8716	High Similarity	NPC1082
0.8716	High Similarity	NPC305912
0.8704	High Similarity	NPC469636
0.8704	High Similarity	NPC474364
0.8679	High Similarity	NPC31786
0.8654	High Similarity	NPC325497
0.8654	High Similarity	NPC118343
0.8649	High Similarity	NPC477411
0.8649	High Similarity	NPC196075
0.8636	High Similarity	NPC321852
0.8636	High Similarity	NPC82899
0.8636	High Similarity	NPC270699
0.8627	High Similarity	NPC130398
0.8571	High Similarity	NPC70624
0.8559	High Similarity	NPC161611
0.8545	High Similarity	NPC167504
0.8545	High Similarity	NPC260818
0.8496	Intermediate Similarity	NPC226093
0.8496	Intermediate Similarity	NPC100353
0.8491	Intermediate Similarity	NPC45613
0.8482	Intermediate Similarity	NPC153053
0.8468	Intermediate Similarity	NPC212415
0.8468	Intermediate Similarity	NPC79496
0.844	Intermediate Similarity	NPC470391
0.8426	Intermediate Similarity	NPC269457
0.8407	Intermediate Similarity	NPC228936
0.8393	Intermediate Similarity	NPC13784
0.8378	Intermediate Similarity	NPC476003
0.8376	Intermediate Similarity	NPC50872
0.8364	Intermediate Similarity	NPC85493
0.835	Intermediate Similarity	NPC23453
0.8318	Intermediate Similarity	NPC188895
0.8304	Intermediate Similarity	NPC474314
0.8304	Intermediate Similarity	NPC158282
0.8302	Intermediate Similarity	NPC203925
0.8291	Intermediate Similarity	NPC473243
0.825	Intermediate Similarity	NPC246166
0.8246	Intermediate Similarity	NPC306740
0.823	Intermediate Similarity	NPC474176
0.8208	Intermediate Similarity	NPC229242
0.8198	Intermediate Similarity	NPC40178
0.819	Intermediate Similarity	NPC45104
0.8174	Intermediate Similarity	NPC135730
0.8158	Intermediate Similarity	NPC474363
0.8137	Intermediate Similarity	NPC173443
0.8131	Intermediate Similarity	NPC472318
0.8131	Intermediate Similarity	NPC98911
0.8125	Intermediate Similarity	NPC273837
0.8108	Intermediate Similarity	NPC47536
0.8099	Intermediate Similarity	NPC295664
0.8087	Intermediate Similarity	NPC474408
0.8087	Intermediate Similarity	NPC474095
0.8083	Intermediate Similarity	NPC46634
0.8083	Intermediate Similarity	NPC223351
0.8077	Intermediate Similarity	NPC77273
0.8073	Intermediate Similarity	NPC234305
0.8053	Intermediate Similarity	NPC291799
0.8051	Intermediate Similarity	NPC204784
0.8039	Intermediate Similarity	NPC304760
0.8034	Intermediate Similarity	NPC469574
0.8034	Intermediate Similarity	NPC217423
0.8033	Intermediate Similarity	NPC476599
0.8018	Intermediate Similarity	NPC472315
0.8018	Intermediate Similarity	NPC474376
0.8018	Intermediate Similarity	NPC475203
0.8018	Intermediate Similarity	NPC472316
0.8	Intermediate Similarity	NPC85977
0.8	Intermediate Similarity	NPC237366
0.7967	Intermediate Similarity	NPC51292
0.7961	Intermediate Similarity	NPC220893
0.7951	Intermediate Similarity	NPC91475
0.7951	Intermediate Similarity	NPC265910
0.7944	Intermediate Similarity	NPC270654
0.7941	Intermediate Similarity	NPC286608
0.7941	Intermediate Similarity	NPC96625
0.7941	Intermediate Similarity	NPC89377
0.7941	Intermediate Similarity	NPC169050
0.7931	Intermediate Similarity	NPC470764
0.7925	Intermediate Similarity	NPC5472
0.7917	Intermediate Similarity	NPC144547
0.7909	Intermediate Similarity	NPC255676
0.7899	Intermediate Similarity	NPC328459
0.7899	Intermediate Similarity	NPC90522
0.789	Intermediate Similarity	NPC112552
0.7886	Intermediate Similarity	NPC275576
0.7886	Intermediate Similarity	NPC121272
0.7869	Intermediate Similarity	NPC228739
0.7863	Intermediate Similarity	NPC188907
0.7863	Intermediate Similarity	NPC471616
0.7857	Intermediate Similarity	NPC136962
0.7857	Intermediate Similarity	NPC475478
0.7857	Intermediate Similarity	NPC473271
0.7845	Intermediate Similarity	NPC87069
0.7843	Intermediate Similarity	NPC318107
0.7833	Intermediate Similarity	NPC232958
0.7833	Intermediate Similarity	NPC988
0.7833	Intermediate Similarity	NPC77000
0.7833	Intermediate Similarity	NPC72977
0.7833	Intermediate Similarity	NPC238861
0.7833	Intermediate Similarity	NPC289432
0.783	Intermediate Similarity	NPC261181
0.7823	Intermediate Similarity	NPC473220
0.7823	Intermediate Similarity	NPC169913
0.7823	Intermediate Similarity	NPC470753
0.7818	Intermediate Similarity	NPC284477
0.7815	Intermediate Similarity	NPC94637
0.781	Intermediate Similarity	NPC119631
0.7805	Intermediate Similarity	NPC470162
0.7805	Intermediate Similarity	NPC470163
0.7797	Intermediate Similarity	NPC190298
0.7795	Intermediate Similarity	NPC475569
0.7788	Intermediate Similarity	NPC211439
0.7788	Intermediate Similarity	NPC20485
0.7787	Intermediate Similarity	NPC217756
0.7787	Intermediate Similarity	NPC472703
0.7778	Intermediate Similarity	NPC82712
0.7778	Intermediate Similarity	NPC147561
0.776	Intermediate Similarity	NPC181715
0.7752	Intermediate Similarity	NPC311339
0.7745	Intermediate Similarity	NPC58616
0.7745	Intermediate Similarity	NPC294134
0.7742	Intermediate Similarity	NPC470765
0.7739	Intermediate Similarity	NPC137315
0.7731	Intermediate Similarity	NPC228318
0.7727	Intermediate Similarity	NPC282895
0.7724	Intermediate Similarity	NPC472704
0.7724	Intermediate Similarity	NPC471466
0.7719	Intermediate Similarity	NPC281604
0.7714	Intermediate Similarity	NPC240108
0.7714	Intermediate Similarity	NPC213156
0.7712	Intermediate Similarity	NPC220540
0.7705	Intermediate Similarity	NPC26285
0.7699	Intermediate Similarity	NPC1065
0.7692	Intermediate Similarity	NPC279916
0.7686	Intermediate Similarity	NPC233282
0.7686	Intermediate Similarity	NPC230951
0.768	Intermediate Similarity	NPC472706
0.7679	Intermediate Similarity	NPC242913
0.7679	Intermediate Similarity	NPC171831
0.7679	Intermediate Similarity	NPC280616
0.7679	Intermediate Similarity	NPC269644
0.7674	Intermediate Similarity	NPC38420
0.7674	Intermediate Similarity	NPC136608
0.7674	Intermediate Similarity	NPC43627
0.7672	Intermediate Similarity	NPC66208
0.7672	Intermediate Similarity	NPC23332
0.7667	Intermediate Similarity	NPC293424
0.7667	Intermediate Similarity	NPC94298
0.7667	Intermediate Similarity	NPC27633
0.7661	Intermediate Similarity	NPC125053
0.7661	Intermediate Similarity	NPC107846
0.7658	Intermediate Similarity	NPC25458
0.7658	Intermediate Similarity	NPC304873
0.7656	Intermediate Similarity	NPC470831
0.7656	Intermediate Similarity	NPC214702
0.7656	Intermediate Similarity	NPC7012
0.7656	Intermediate Similarity	NPC238370
0.7647	Intermediate Similarity	NPC128825
0.7647	Intermediate Similarity	NPC470860
0.7638	Intermediate Similarity	NPC473247
0.7638	Intermediate Similarity	NPC66246
0.7638	Intermediate Similarity	NPC238309

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 NPC474157 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	967
0.2-0.3	1374
0.3-0.4	2589
0.4-0.5	2105
0.5-0.6	1238
0.6-0.7	431
0.7-0.8	112
0.8-0.85	14
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9065	High Similarity	NPD2181	Clinical (unspecified phase)
0.8879	High Similarity	NPD2182	Approved
0.8679	High Similarity	NPD164	Approved
0.8654	High Similarity	NPD1238	Approved
0.8468	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1282	Approved
0.7843	Intermediate Similarity	NPD9257	Approved
0.7843	Intermediate Similarity	NPD9259	Approved
0.7838	Intermediate Similarity	NPD5909	Discontinued
0.7833	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD1202	Approved
0.7807	Intermediate Similarity	NPD2067	Discontinued
0.7778	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD6832	Phase 2
0.7692	Intermediate Similarity	NPD1241	Discontinued
0.7667	Intermediate Similarity	NPD9545	Approved
0.7647	Intermediate Similarity	NPD9493	Approved
0.7638	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD7008	Discontinued
0.7565	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6287	Discontinued
0.7547	Intermediate Similarity	NPD9256	Approved
0.7547	Intermediate Similarity	NPD9258	Approved
0.754	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD1989	Approved
0.7522	Intermediate Similarity	NPD1237	Approved
0.752	Intermediate Similarity	NPD2199	Approved
0.752	Intermediate Similarity	NPD2198	Approved
0.7479	Intermediate Similarity	NPD5951	Approved
0.7419	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD1019	Discontinued
0.7391	Intermediate Similarity	NPD3134	Approved
0.7387	Intermediate Similarity	NPD9495	Approved
0.7381	Intermediate Similarity	NPD1876	Approved
0.736	Intermediate Similarity	NPD3972	Approved
0.736	Intermediate Similarity	NPD9717	Approved
0.7328	Intermediate Similarity	NPD1358	Approved
0.7323	Intermediate Similarity	NPD2797	Approved
0.7321	Intermediate Similarity	NPD2066	Phase 3
0.7281	Intermediate Similarity	NPD1930	Approved
0.7281	Intermediate Similarity	NPD9261	Approved
0.7281	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD1929	Approved
0.7281	Intermediate Similarity	NPD6647	Phase 2
0.728	Intermediate Similarity	NPD1281	Approved
0.7273	Intermediate Similarity	NPD9260	Approved
0.7266	Intermediate Similarity	NPD2798	Approved
0.7264	Intermediate Similarity	NPD1087	Approved
0.7239	Intermediate Similarity	NPD3748	Approved
0.7222	Intermediate Similarity	NPD3672	Approved
0.7222	Intermediate Similarity	NPD3673	Approved
0.7197	Intermediate Similarity	NPD4307	Phase 2
0.719	Intermediate Similarity	NPD2629	Approved
0.7188	Intermediate Similarity	NPD1203	Approved
0.7188	Intermediate Similarity	NPD3266	Approved
0.7188	Intermediate Similarity	NPD3267	Approved
0.7177	Intermediate Similarity	NPD5691	Approved
0.7176	Intermediate Similarity	NPD3764	Approved
0.7164	Intermediate Similarity	NPD2569	Approved
0.7164	Intermediate Similarity	NPD2567	Approved
0.7157	Intermediate Similarity	NPD9490	Approved
0.7155	Intermediate Similarity	NPD9697	Approved
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD17	Approved
0.712	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1283	Approved
0.7109	Intermediate Similarity	NPD5667	Approved
0.7103	Intermediate Similarity	NPD650	Approved
0.7101	Intermediate Similarity	NPD4628	Phase 3
0.7097	Intermediate Similarity	NPD1894	Discontinued
0.7092	Intermediate Similarity	NPD6273	Approved
0.7087	Intermediate Similarity	NPD6637	Approved
0.708	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2979	Phase 3
0.7064	Intermediate Similarity	NPD1089	Approved
0.7064	Intermediate Similarity	NPD1090	Approved
0.7064	Intermediate Similarity	NPD1086	Approved
0.7059	Intermediate Similarity	NPD2796	Approved
0.7059	Intermediate Similarity	NPD2438	Suspended
0.7048	Intermediate Similarity	NPD9491	Approved
0.7045	Intermediate Similarity	NPD2313	Discontinued
0.7045	Intermediate Similarity	NPD3268	Approved
0.704	Intermediate Similarity	NPD1651	Approved
0.704	Intermediate Similarity	NPD5585	Approved
0.7034	Intermediate Similarity	NPD9264	Approved
0.7034	Intermediate Similarity	NPD9263	Approved
0.7034	Intermediate Similarity	NPD9267	Approved
0.7027	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7798	Approved
0.7015	Intermediate Similarity	NPD1933	Approved
0.7007	Intermediate Similarity	NPD2346	Discontinued
0.7007	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7236	Approved
0.7	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7609	Phase 3
0.6992	Remote Similarity	NPD7713	Phase 3
0.6985	Remote Similarity	NPD4308	Phase 3
0.6985	Remote Similarity	NPD2799	Discontinued
0.6978	Remote Similarity	NPD7003	Approved
0.6978	Remote Similarity	NPD3750	Approved
0.6975	Remote Similarity	NPD74	Approved
0.6975	Remote Similarity	NPD9266	Approved
0.6972	Remote Similarity	NPD800	Approved
0.697	Remote Similarity	NPD6039	Approved
0.6964	Remote Similarity	NPD1693	Approved
0.6964	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1608	Approved
0.6944	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD969	Suspended
0.694	Remote Similarity	NPD3142	Approved
0.694	Remote Similarity	NPD3373	Approved
0.694	Remote Similarity	NPD3140	Approved
0.6937	Remote Similarity	NPD7631	Approved
0.6937	Remote Similarity	NPD1088	Approved
0.6935	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2935	Discontinued
0.693	Remote Similarity	NPD5926	Approved
0.6929	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3887	Approved
0.6923	Remote Similarity	NPD3047	Approved
0.6923	Remote Similarity	NPD552	Approved
0.6923	Remote Similarity	NPD3048	Approved
0.6923	Remote Similarity	NPD9567	Approved
0.6923	Remote Similarity	NPD553	Approved
0.6923	Remote Similarity	NPD3046	Approved
0.6917	Remote Similarity	NPD5235	Approved
0.6917	Remote Similarity	NPD5237	Approved
0.6917	Remote Similarity	NPD5239	Approved
0.6917	Remote Similarity	NPD5240	Approved
0.6917	Remote Similarity	NPD5236	Approved
0.6906	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1932	Approved
0.6893	Remote Similarity	NPD225	Approved
0.6893	Remote Similarity	NPD227	Approved
0.6891	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6858	Approved
0.6885	Remote Similarity	NPD7094	Approved
0.6885	Remote Similarity	NPD5277	Phase 2
0.688	Remote Similarity	NPD2347	Approved
0.6875	Remote Similarity	NPD1563	Approved
0.6866	Remote Similarity	NPD6233	Phase 2
0.686	Remote Similarity	NPD2201	Approved
0.6857	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4198	Discontinued
0.685	Remote Similarity	NPD5306	Approved
0.685	Remote Similarity	NPD5305	Approved
0.685	Remote Similarity	NPD4626	Approved
0.6847	Remote Similarity	NPD1239	Approved
0.6838	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2897	Discontinued
0.6831	Remote Similarity	NPD6799	Approved
0.6829	Remote Similarity	NPD6010	Discontinued
0.6812	Remote Similarity	NPD4477	Approved
0.6812	Remote Similarity	NPD4476	Approved
0.6812	Remote Similarity	NPD2531	Phase 2
0.6812	Remote Similarity	NPD1551	Phase 2
0.6806	Remote Similarity	NPD5403	Approved
0.68	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4106	Approved
0.6797	Remote Similarity	NPD4136	Approved
0.6797	Remote Similarity	NPD4135	Approved
0.6791	Remote Similarity	NPD6798	Discontinued
0.6791	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD411	Approved
0.6783	Remote Similarity	NPD5401	Approved
0.6777	Remote Similarity	NPD1756	Approved
0.6777	Remote Similarity	NPD1752	Approved
0.6769	Remote Similarity	NPD4359	Approved
0.6765	Remote Similarity	NPD230	Phase 1
0.6765	Remote Similarity	NPD4618	Approved
0.6765	Remote Similarity	NPD6355	Discontinued
0.6765	Remote Similarity	NPD447	Suspended
0.6765	Remote Similarity	NPD4622	Approved
0.6759	Remote Similarity	NPD7239	Suspended
0.6757	Remote Similarity	NPD7819	Suspended
0.6748	Remote Similarity	NPD5535	Approved
0.6744	Remote Similarity	NPD4806	Approved
0.6744	Remote Similarity	NPD4807	Approved
0.6741	Remote Similarity	NPD8032	Phase 2
0.6741	Remote Similarity	NPD4062	Phase 3
0.6729	Remote Similarity	NPD3971	Phase 1
0.6723	Remote Similarity	NPD5048	Discontinued
0.6719	Remote Similarity	NPD1778	Approved
0.6712	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD226	Approved
0.6698	Remote Similarity	NPD942	Approved
0.6696	Remote Similarity	NPD1564	Approved
0.6696	Remote Similarity	NPD1566	Phase 3
0.6696	Remote Similarity	NPD1565	Approved
0.6696	Remote Similarity	NPD3495	Discontinued
0.6695	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2650	Approved
0.6694	Remote Similarity	NPD2652	Approved
0.6694	Remote Similarity	NPD2329	Discontinued
0.6692	Remote Similarity	NPD4878	Approved
0.6692	Remote Similarity	NPD1481	Phase 2
0.6691	Remote Similarity	NPD1240	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