NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.08
Volume:	226.843
LogP:	2.78
LogD:	2.931
LogS:	-3.283
# Rotatable Bonds:	2
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.839
Synthetic Accessibility Score:	2.608
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:	-4.785
MDCK Permeability:	1.6798085198388435e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.36
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.885
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	96.33821868896484%
Volume Distribution (VD):	0.334
Pgp-substrate:	6.357003688812256%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.649
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.514
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.483
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.383
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	3.28
Half-life (T1/2):	0.369

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.339
Skin Sensitization:	0.676
Carcinogencity:	0.778
Eye Corrosion:	0.25
Eye Irritation:	0.984
Respiratory Toxicity:	0.34

Download Data

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

Natural Product: NPC46634

Natural Product ID:	NPC46634
*Common Name:**	Artemidinol
IUPAC Name:	3-[(E)-but-1-enyl]-5-hydroxyisochromen-1-one
Synonyms:	Artemidinol
Standard InCHIKey:	QBZHMYUXUVZDQT-HWKANZROSA-N
Standard InCHI:	InChI=1S/C13H12O3/c1-2-3-5-9-8-11-10(13(15)16-9)6-4-7-12(11)14/h3-8,14H,2H2,1H3/b5-3+
SMILES:	CC/C=C/c1cc2c(cccc2O)c(=O)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471176
PubChem CID:	23264915
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	underground organs	n.a.	n.a.	PMID[14738379]
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	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
EC50	1
MIC	2
Others	1

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	50.0	ug.mL-1	PMID[534128]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	32.0	ug ml-1	PMID[534128]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	12.0	ug.mL-1	PMID[534128]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	>	100.0	ug	PMID[534128]

☑ 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 NPC46634 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	341
0.1-0.2	1685
0.2-0.3	4462
0.3-0.4	10420
0.4-0.5	7519
0.5-0.6	4542
0.6-0.7	7668
0.7-0.8	5708
0.8-0.85	313
0.85-0.9	33
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC265910
0.9333	High Similarity	NPC91475
0.9106	High Similarity	NPC181715
0.9052	High Similarity	NPC81808
0.8852	High Similarity	NPC217756
0.8824	High Similarity	NPC240664
0.8672	High Similarity	NPC7012
0.8667	High Similarity	NPC125252
0.8667	High Similarity	NPC160199
0.8629	High Similarity	NPC275145
0.8538	High Similarity	NPC472591
0.8537	High Similarity	NPC165197
0.8527	High Similarity	NPC470831
0.8527	High Similarity	NPC214702
0.8522	High Similarity	NPC187913
0.8504	High Similarity	NPC470841
0.8504	High Similarity	NPC71525
0.8485	Intermediate Similarity	NPC156307
0.8473	Intermediate Similarity	NPC175943
0.8468	Intermediate Similarity	NPC25168
0.8462	Intermediate Similarity	NPC477406
0.8455	Intermediate Similarity	NPC206778
0.8455	Intermediate Similarity	NPC285829
0.8448	Intermediate Similarity	NPC34715
0.8443	Intermediate Similarity	NPC94637
0.8435	Intermediate Similarity	NPC209632
0.843	Intermediate Similarity	NPC108288
0.843	Intermediate Similarity	NPC128825
0.8425	Intermediate Similarity	NPC51037
0.8421	Intermediate Similarity	NPC62907
0.8403	Intermediate Similarity	NPC272524
0.84	Intermediate Similarity	NPC297193
0.8397	Intermediate Similarity	NPC43627
0.8387	Intermediate Similarity	NPC222876
0.8387	Intermediate Similarity	NPC179092
0.8387	Intermediate Similarity	NPC272454
0.8387	Intermediate Similarity	NPC178395
0.8387	Intermediate Similarity	NPC301987
0.8387	Intermediate Similarity	NPC115188
0.8387	Intermediate Similarity	NPC159760
0.8387	Intermediate Similarity	NPC35856
0.8387	Intermediate Similarity	NPC26433
0.8387	Intermediate Similarity	NPC292665
0.8387	Intermediate Similarity	NPC244994
0.8374	Intermediate Similarity	NPC184579
0.8374	Intermediate Similarity	NPC90522
0.8374	Intermediate Similarity	NPC328459
0.8374	Intermediate Similarity	NPC472593
0.8374	Intermediate Similarity	NPC233165
0.8358	Intermediate Similarity	NPC197666
0.8358	Intermediate Similarity	NPC61590
0.8358	Intermediate Similarity	NPC126739
0.8348	Intermediate Similarity	NPC114594
0.8347	Intermediate Similarity	NPC240163
0.8333	Intermediate Similarity	NPC474097
0.832	Intermediate Similarity	NPC198336
0.8308	Intermediate Similarity	NPC7569
0.8306	Intermediate Similarity	NPC72977
0.8306	Intermediate Similarity	NPC233282
0.8306	Intermediate Similarity	NPC216297
0.8306	Intermediate Similarity	NPC473662
0.8306	Intermediate Similarity	NPC7151
0.8296	Intermediate Similarity	NPC256463
0.8296	Intermediate Similarity	NPC216312
0.8296	Intermediate Similarity	NPC471602
0.8296	Intermediate Similarity	NPC29771
0.8296	Intermediate Similarity	NPC134969
0.8296	Intermediate Similarity	NPC299405
0.8296	Intermediate Similarity	NPC111422
0.8296	Intermediate Similarity	NPC306835
0.8296	Intermediate Similarity	NPC476477
0.8296	Intermediate Similarity	NPC295339
0.8295	Intermediate Similarity	NPC237225
0.8279	Intermediate Similarity	NPC477453
0.8271	Intermediate Similarity	NPC22222
0.8271	Intermediate Similarity	NPC142027
0.8271	Intermediate Similarity	NPC27407
0.8271	Intermediate Similarity	NPC281513
0.8271	Intermediate Similarity	NPC298900
0.8268	Intermediate Similarity	NPC310540
0.8268	Intermediate Similarity	NPC4012
0.8268	Intermediate Similarity	NPC117794
0.8264	Intermediate Similarity	NPC41851
0.8261	Intermediate Similarity	NPC13426
0.8261	Intermediate Similarity	NPC274085
0.8261	Intermediate Similarity	NPC89664
0.8258	Intermediate Similarity	NPC289572
0.8258	Intermediate Similarity	NPC157478
0.8258	Intermediate Similarity	NPC263817
0.8258	Intermediate Similarity	NPC200422
0.8258	Intermediate Similarity	NPC295406
0.8258	Intermediate Similarity	NPC171968
0.8258	Intermediate Similarity	NPC59459
0.8254	Intermediate Similarity	NPC244351
0.8254	Intermediate Similarity	NPC283514
0.8254	Intermediate Similarity	NPC307174
0.825	Intermediate Similarity	NPC231717
0.8244	Intermediate Similarity	NPC205360
0.8235	Intermediate Similarity	NPC32749
0.8235	Intermediate Similarity	NPC220496
0.8235	Intermediate Similarity	NPC290664
0.8235	Intermediate Similarity	NPC42262
0.8235	Intermediate Similarity	NPC260818
0.8235	Intermediate Similarity	NPC37992
0.8235	Intermediate Similarity	NPC147542
0.8235	Intermediate Similarity	NPC241349
0.8235	Intermediate Similarity	NPC327916
0.8226	Intermediate Similarity	NPC232178
0.822	Intermediate Similarity	NPC269023
0.822	Intermediate Similarity	NPC99846
0.822	Intermediate Similarity	NPC85493
0.8217	Intermediate Similarity	NPC209959
0.8211	Intermediate Similarity	NPC269414
0.8209	Intermediate Similarity	NPC291454
0.8209	Intermediate Similarity	NPC326847
0.8209	Intermediate Similarity	NPC50455
0.8205	Intermediate Similarity	NPC37622
0.8205	Intermediate Similarity	NPC30594
0.8203	Intermediate Similarity	NPC4164
0.8203	Intermediate Similarity	NPC472592
0.8203	Intermediate Similarity	NPC287473
0.8197	Intermediate Similarity	NPC161304
0.8195	Intermediate Similarity	NPC274876
0.8189	Intermediate Similarity	NPC477153
0.8189	Intermediate Similarity	NPC135062
0.8189	Intermediate Similarity	NPC182646
0.8189	Intermediate Similarity	NPC248786
0.8188	Intermediate Similarity	NPC476473
0.8182	Intermediate Similarity	NPC470160
0.8182	Intermediate Similarity	NPC477407
0.8175	Intermediate Similarity	NPC257003
0.8175	Intermediate Similarity	NPC91546
0.8175	Intermediate Similarity	NPC149533
0.8175	Intermediate Similarity	NPC158634
0.8175	Intermediate Similarity	NPC471444
0.8168	Intermediate Similarity	NPC31539
0.8168	Intermediate Similarity	NPC278787
0.8167	Intermediate Similarity	NPC321852
0.8167	Intermediate Similarity	NPC228609
0.8162	Intermediate Similarity	NPC268052
0.8162	Intermediate Similarity	NPC32360
0.8162	Intermediate Similarity	NPC92655
0.816	Intermediate Similarity	NPC14177
0.816	Intermediate Similarity	NPC474874
0.8154	Intermediate Similarity	NPC81261
0.8154	Intermediate Similarity	NPC165257
0.8145	Intermediate Similarity	NPC27633
0.8145	Intermediate Similarity	NPC94298
0.814	Intermediate Similarity	NPC306765
0.8136	Intermediate Similarity	NPC141523
0.8134	Intermediate Similarity	NPC254832
0.8134	Intermediate Similarity	NPC29317
0.8134	Intermediate Similarity	NPC176102
0.8134	Intermediate Similarity	NPC229638
0.8134	Intermediate Similarity	NPC267539
0.8134	Intermediate Similarity	NPC204257
0.8134	Intermediate Similarity	NPC71108
0.813	Intermediate Similarity	NPC131192
0.813	Intermediate Similarity	NPC163398
0.813	Intermediate Similarity	NPC312800
0.8129	Intermediate Similarity	NPC103910
0.8125	Intermediate Similarity	NPC234890
0.8125	Intermediate Similarity	NPC74507
0.8125	Intermediate Similarity	NPC470163
0.8125	Intermediate Similarity	NPC236189
0.8125	Intermediate Similarity	NPC184219
0.8125	Intermediate Similarity	NPC145134
0.8125	Intermediate Similarity	NPC470162
0.812	Intermediate Similarity	NPC153783
0.8116	Intermediate Similarity	NPC314271
0.8116	Intermediate Similarity	NPC474300
0.8115	Intermediate Similarity	NPC474685
0.811	Intermediate Similarity	NPC300274
0.811	Intermediate Similarity	NPC132518
0.811	Intermediate Similarity	NPC477151
0.811	Intermediate Similarity	NPC311219
0.811	Intermediate Similarity	NPC67300
0.8106	Intermediate Similarity	NPC189823
0.8106	Intermediate Similarity	NPC219892
0.8106	Intermediate Similarity	NPC141549
0.8099	Intermediate Similarity	NPC17693
0.8095	Intermediate Similarity	NPC190971
0.8092	Intermediate Similarity	NPC226855
0.8092	Intermediate Similarity	NPC94810
0.8088	Intermediate Similarity	NPC221104
0.8083	Intermediate Similarity	NPC474157
0.8077	Intermediate Similarity	NPC95034
0.8077	Intermediate Similarity	NPC142087
0.8077	Intermediate Similarity	NPC45537
0.8077	Intermediate Similarity	NPC158654
0.8074	Intermediate Similarity	NPC472881
0.8074	Intermediate Similarity	NPC235115
0.8074	Intermediate Similarity	NPC141934
0.8071	Intermediate Similarity	NPC131766
0.8067	Intermediate Similarity	NPC224584
0.8065	Intermediate Similarity	NPC45104
0.8062	Intermediate Similarity	NPC240744
0.8062	Intermediate Similarity	NPC167055
0.8058	Intermediate Similarity	NPC21873
0.8047	Intermediate Similarity	NPC477152

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 NPC46634 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	978
0.2-0.3	1453
0.3-0.4	2556
0.4-0.5	1990
0.5-0.6	1222
0.6-0.7	469
0.7-0.8	136
0.8-0.85	16
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.843	Intermediate Similarity	NPD9493	Approved
0.843	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD2346	Discontinued
0.8168	Intermediate Similarity	NPD3764	Approved
0.8162	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8145	Intermediate Similarity	NPD9545	Approved
0.812	Intermediate Similarity	NPD447	Suspended
0.811	Intermediate Similarity	NPD9717	Approved
0.8062	Intermediate Similarity	NPD1203	Approved
0.803	Intermediate Similarity	NPD2313	Discontinued
0.8015	Intermediate Similarity	NPD2935	Discontinued
0.7923	Intermediate Similarity	NPD2797	Approved
0.7923	Intermediate Similarity	NPD1470	Approved
0.7917	Intermediate Similarity	NPD9266	Approved
0.7917	Intermediate Similarity	NPD74	Approved
0.7914	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD411	Approved
0.7891	Intermediate Similarity	NPD1201	Approved
0.7881	Intermediate Similarity	NPD164	Approved
0.7863	Intermediate Similarity	NPD2798	Approved
0.7847	Intermediate Similarity	NPD3226	Approved
0.7846	Intermediate Similarity	NPD1283	Approved
0.7833	Intermediate Similarity	NPD9267	Approved
0.7833	Intermediate Similarity	NPD9263	Approved
0.7833	Intermediate Similarity	NPD9264	Approved
0.7829	Intermediate Similarity	NPD1608	Approved
0.781	Intermediate Similarity	NPD4308	Phase 3
0.781	Intermediate Similarity	NPD2799	Discontinued
0.7769	Intermediate Similarity	NPD2182	Approved
0.7734	Intermediate Similarity	NPD4626	Approved
0.7724	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD230	Phase 1
0.7698	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7003	Approved
0.766	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD1164	Approved
0.7642	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3268	Approved
0.7615	Intermediate Similarity	NPD1281	Approved
0.7597	Intermediate Similarity	NPD17	Approved
0.7591	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD2344	Approved
0.7557	Intermediate Similarity	NPD1481	Phase 2
0.7554	Intermediate Similarity	NPD3748	Approved
0.7538	Intermediate Similarity	NPD3496	Discontinued
0.7537	Intermediate Similarity	NPD9494	Approved
0.7521	Intermediate Similarity	NPD9697	Approved
0.7519	Intermediate Similarity	NPD5691	Approved
0.7518	Intermediate Similarity	NPD4307	Phase 2
0.75	Intermediate Similarity	NPD9261	Approved
0.75	Intermediate Similarity	NPD1551	Phase 2
0.7483	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1535	Discovery
0.7481	Intermediate Similarity	NPD422	Phase 1
0.7481	Intermediate Similarity	NPD6832	Phase 2
0.7463	Intermediate Similarity	NPD1019	Discontinued
0.7462	Intermediate Similarity	NPD1778	Approved
0.746	Intermediate Similarity	NPD1241	Discontinued
0.7448	Intermediate Similarity	NPD2534	Approved
0.7448	Intermediate Similarity	NPD2533	Approved
0.7448	Intermediate Similarity	NPD2532	Approved
0.7444	Intermediate Similarity	NPD1876	Approved
0.7413	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD9281	Approved
0.7402	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6273	Approved
0.7395	Intermediate Similarity	NPD1238	Approved
0.7391	Intermediate Similarity	NPD1240	Approved
0.7388	Intermediate Similarity	NPD3266	Approved
0.7388	Intermediate Similarity	NPD3267	Approved
0.7376	Intermediate Similarity	NPD5406	Approved
0.7376	Intermediate Similarity	NPD5405	Approved
0.7376	Intermediate Similarity	NPD5408	Approved
0.7376	Intermediate Similarity	NPD5404	Approved
0.7361	Intermediate Similarity	NPD2309	Approved
0.7348	Intermediate Similarity	NPD1611	Approved
0.7348	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6671	Approved
0.7343	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3225	Approved
0.7305	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1510	Phase 2
0.7305	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD9256	Approved
0.7304	Intermediate Similarity	NPD9258	Approved
0.7295	Intermediate Similarity	NPD5909	Discontinued
0.7293	Intermediate Similarity	NPD9269	Phase 2
0.7292	Intermediate Similarity	NPD4628	Phase 3
0.7286	Intermediate Similarity	NPD1607	Approved
0.7285	Intermediate Similarity	NPD7819	Suspended
0.7285	Intermediate Similarity	NPD1465	Phase 2
0.7266	Intermediate Similarity	NPD5951	Approved
0.7266	Intermediate Similarity	NPD4060	Phase 1
0.7266	Intermediate Similarity	NPD2979	Phase 3
0.726	Intermediate Similarity	NPD1511	Approved
0.7254	Intermediate Similarity	NPD4476	Approved
0.7254	Intermediate Similarity	NPD4477	Approved
0.7252	Intermediate Similarity	NPD5585	Approved
0.7252	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9268	Approved
0.7252	Intermediate Similarity	NPD1651	Approved
0.7227	Intermediate Similarity	NPD288	Approved
0.7209	Intermediate Similarity	NPD709	Approved
0.72	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2932	Approved
0.7197	Intermediate Similarity	NPD3019	Approved
0.7194	Intermediate Similarity	NPD6663	Approved
0.7194	Intermediate Similarity	NPD520	Approved
0.7179	Intermediate Similarity	NPD6232	Discontinued
0.7176	Intermediate Similarity	NPD1894	Discontinued
0.7174	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD8166	Discontinued
0.7164	Intermediate Similarity	NPD3972	Approved
0.7162	Intermediate Similarity	NPD1512	Approved
0.7153	Intermediate Similarity	NPD5736	Approved
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD844	Approved
0.7143	Intermediate Similarity	NPD3749	Approved
0.7133	Intermediate Similarity	NPD2649	Approved
0.7133	Intermediate Similarity	NPD2651	Approved
0.7124	Intermediate Similarity	NPD5402	Approved
0.7095	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6355	Discontinued
0.7092	Intermediate Similarity	NPD1184	Approved
0.7092	Intermediate Similarity	NPD1933	Approved
0.7083	Intermediate Similarity	NPD1471	Phase 3
0.7078	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1929	Approved
0.7073	Intermediate Similarity	NPD1930	Approved
0.7073	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8032	Phase 2
0.7067	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2801	Approved
0.705	Intermediate Similarity	NPD7008	Discontinued
0.7044	Intermediate Similarity	NPD7473	Discontinued
0.704	Intermediate Similarity	NPD3134	Approved
0.7039	Intermediate Similarity	NPD2672	Discontinued
0.7034	Intermediate Similarity	NPD1549	Phase 2
0.702	Intermediate Similarity	NPD3455	Phase 2
0.702	Intermediate Similarity	NPD7458	Discontinued
0.7014	Intermediate Similarity	NPD6100	Approved
0.7014	Intermediate Similarity	NPD6099	Approved
0.7013	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD6844	Discontinued
0.6986	Remote Similarity	NPD1243	Approved
0.6985	Remote Similarity	NPD4359	Approved
0.6985	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1358	Approved
0.6977	Remote Similarity	NPD7635	Approved
0.6975	Remote Similarity	NPD1202	Approved
0.6974	Remote Similarity	NPD3684	Discontinued
0.6972	Remote Similarity	NPD4618	Approved
0.6972	Remote Similarity	NPD4622	Approved
0.6968	Remote Similarity	NPD7768	Phase 2
0.6966	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7440	Discontinued
0.6957	Remote Similarity	NPD9257	Approved
0.6957	Remote Similarity	NPD9259	Approved
0.6957	Remote Similarity	NPD5844	Phase 1
0.6947	Remote Similarity	NPD255	Approved
0.6947	Remote Similarity	NPD256	Approved
0.694	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7095	Approved
0.6923	Remote Similarity	NPD1398	Phase 1
0.6923	Remote Similarity	NPD6653	Approved
0.6917	Remote Similarity	NPD1759	Phase 1
0.6913	Remote Similarity	NPD6799	Approved
0.6913	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD968	Approved
0.6903	Remote Similarity	NPD3817	Phase 2
0.6899	Remote Similarity	NPD228	Approved
0.6897	Remote Similarity	NPD2531	Phase 2
0.6897	Remote Similarity	NPD2796	Approved
0.6897	Remote Similarity	NPD2438	Suspended
0.6897	Remote Similarity	NPD6032	Approved
0.6894	Remote Similarity	NPD7177	Discontinued
0.6892	Remote Similarity	NPD2354	Approved
0.6892	Remote Similarity	NPD6190	Approved
0.6889	Remote Similarity	NPD3847	Discontinued
0.6887	Remote Similarity	NPD5403	Approved
0.6887	Remote Similarity	NPD920	Approved
0.6883	Remote Similarity	NPD1934	Approved
0.688	Remote Similarity	NPD1237	Approved
0.6879	Remote Similarity	NPD1296	Phase 2
0.6879	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5688	Approved
0.6875	Remote Similarity	NPD5689	Approved
0.6871	Remote Similarity	NPD2800	Approved
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5401	Approved
0.6867	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1578	Phase 2

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