NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.08
Volume:	226.843
LogP:	3.113
LogD:	3.138
LogS:	-3.385
# 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:	2.694
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.793
MDCK Permeability:	1.724653884593863e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.344
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.614
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	97.36809539794922%
Volume Distribution (VD):	0.367
Pgp-substrate:	4.21351957321167%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.805
CYP2C19-inhibitor:	0.692
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.669
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.45
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	2.612
Half-life (T1/2):	0.407

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.229
Skin Sensitization:	0.815
Carcinogencity:	0.767
Eye Corrosion:	0.542
Eye Irritation:	0.983
Respiratory Toxicity:	0.337

Download Data

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

Natural Product: NPC91475

Natural Product ID:	NPC91475
*Common Name:**	8-Hydroxyartemidin
IUPAC Name:	3-[(E)-but-1-enyl]-8-hydroxyisochromen-1-one
Synonyms:	8-Hydroxyartemidin
Standard InCHIKey:	KIVJBPPONQCANS-ZZXKWVIFSA-N
Standard InCHI:	InChI=1S/C13H12O3/c1-2-3-6-10-8-9-5-4-7-11(14)12(9)13(15)16-10/h3-8,14H,2H2,1H3/b6-3+
SMILES:	CC/C=C/c1cc2cccc(c2c(=O)o1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446590
PubChem CID:	44575586
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	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	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	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	=	25.0	ug.mL-1	PMID[492287]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	19.0	ug ml-1	PMID[492287]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	4.0	ug.mL-1	PMID[492287]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	>	100.0	ug	PMID[492287]

☑ 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 NPC91475 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	366
0.1-0.2	1760
0.2-0.3	4630
0.3-0.4	10559
0.4-0.5	7351
0.5-0.6	4188
0.6-0.7	6243
0.7-0.8	5879
0.8-0.85	1389
0.85-0.9	291
0.9-0.95	37
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC265910
0.975	High Similarity	NPC181715
0.9333	High Similarity	NPC46634
0.9316	High Similarity	NPC125252
0.9127	High Similarity	NPC214702
0.9127	High Similarity	NPC470831
0.9062	High Similarity	NPC175943
0.9008	High Similarity	NPC222876
0.9008	High Similarity	NPC26433
0.9008	High Similarity	NPC244994
0.9008	High Similarity	NPC301987
0.9008	High Similarity	NPC272454
0.9008	High Similarity	NPC115188
0.9008	High Similarity	NPC178395
0.9008	High Similarity	NPC35856
0.9008	High Similarity	NPC179092
0.9008	High Similarity	NPC292665
0.9008	High Similarity	NPC159760
0.9	High Similarity	NPC184579
0.9	High Similarity	NPC233165
0.8976	High Similarity	NPC7012
0.8934	High Similarity	NPC198336
0.8917	High Similarity	NPC94637
0.8908	High Similarity	NPC128825
0.8862	High Similarity	NPC244351
0.8862	High Similarity	NPC283514
0.8846	High Similarity	NPC142027
0.8846	High Similarity	NPC27407
0.8843	High Similarity	NPC90522
0.8843	High Similarity	NPC328459
0.8837	High Similarity	NPC43627
0.8779	High Similarity	NPC50455
0.8779	High Similarity	NPC291454
0.877	High Similarity	NPC233282
0.877	High Similarity	NPC72977
0.8769	High Similarity	NPC474097
0.876	High Similarity	NPC470160
0.8731	High Similarity	NPC158634
0.8722	High Similarity	NPC268052
0.8722	High Similarity	NPC134969
0.8722	High Similarity	NPC32360
0.872	High Similarity	NPC470162
0.872	High Similarity	NPC470163
0.8712	High Similarity	NPC62907
0.871	High Similarity	NPC217756
0.8692	High Similarity	NPC153783
0.8682	High Similarity	NPC219892
0.8682	High Similarity	NPC189823
0.8661	High Similarity	NPC71525
0.8651	High Similarity	NPC240744
0.8651	High Similarity	NPC167055
0.8651	High Similarity	NPC4164
0.8647	High Similarity	NPC126739
0.8647	High Similarity	NPC197666
0.8636	High Similarity	NPC235115
0.8605	High Similarity	NPC473271
0.8595	High Similarity	NPC477453
0.8593	High Similarity	NPC149533
0.8582	High Similarity	NPC92655
0.8582	High Similarity	NPC247409
0.8571	High Similarity	NPC135837
0.8571	High Similarity	NPC261292
0.8571	High Similarity	NPC301915
0.8571	High Similarity	NPC236189
0.8561	High Similarity	NPC298900
0.8561	High Similarity	NPC180905
0.8561	High Similarity	NPC182496
0.856	High Similarity	NPC311219
0.8516	High Similarity	NPC470841
0.8507	High Similarity	NPC33144
0.8507	High Similarity	NPC61590
0.8507	High Similarity	NPC478200
0.8507	High Similarity	NPC221104
0.8504	High Similarity	NPC262671
0.8504	High Similarity	NPC201728
0.8496	Intermediate Similarity	NPC242712
0.8473	Intermediate Similarity	NPC477406
0.8468	Intermediate Similarity	NPC206778
0.8468	Intermediate Similarity	NPC285829
0.8467	Intermediate Similarity	NPC478202
0.8456	Intermediate Similarity	NPC130485
0.8456	Intermediate Similarity	NPC220106
0.8456	Intermediate Similarity	NPC470842
0.845	Intermediate Similarity	NPC95537
0.8444	Intermediate Similarity	NPC52358
0.8444	Intermediate Similarity	NPC295339
0.8443	Intermediate Similarity	NPC108288
0.8433	Intermediate Similarity	NPC70380
0.8433	Intermediate Similarity	NPC71256
0.843	Intermediate Similarity	NPC81808
0.8425	Intermediate Similarity	NPC193805
0.8409	Intermediate Similarity	NPC289572
0.8409	Intermediate Similarity	NPC157478
0.8409	Intermediate Similarity	NPC295406
0.8409	Intermediate Similarity	NPC200422
0.8406	Intermediate Similarity	NPC257025
0.8394	Intermediate Similarity	NPC105648
0.8394	Intermediate Similarity	NPC250755
0.8394	Intermediate Similarity	NPC314271
0.8394	Intermediate Similarity	NPC474385
0.8394	Intermediate Similarity	NPC82913
0.839	Intermediate Similarity	NPC100551
0.8387	Intermediate Similarity	NPC472593
0.8382	Intermediate Similarity	NPC155205
0.8382	Intermediate Similarity	NPC158472
0.8374	Intermediate Similarity	NPC217423
0.837	Intermediate Similarity	NPC191835
0.837	Intermediate Similarity	NPC94248
0.837	Intermediate Similarity	NPC212693
0.837	Intermediate Similarity	NPC472602
0.8361	Intermediate Similarity	NPC188907
0.8358	Intermediate Similarity	NPC158481
0.8347	Intermediate Similarity	NPC211421
0.8345	Intermediate Similarity	NPC312789
0.8333	Intermediate Similarity	NPC469542
0.8321	Intermediate Similarity	NPC247477
0.8321	Intermediate Similarity	NPC313123
0.8321	Intermediate Similarity	NPC472035
0.8321	Intermediate Similarity	NPC475730
0.8321	Intermediate Similarity	NPC53649
0.8321	Intermediate Similarity	NPC17840
0.8321	Intermediate Similarity	NPC478201
0.8321	Intermediate Similarity	NPC31539
0.8321	Intermediate Similarity	NPC67650
0.8321	Intermediate Similarity	NPC90411
0.8321	Intermediate Similarity	NPC12694
0.8321	Intermediate Similarity	NPC1704
0.8321	Intermediate Similarity	NPC478217
0.832	Intermediate Similarity	NPC7151
0.832	Intermediate Similarity	NPC474874
0.832	Intermediate Similarity	NPC473662
0.832	Intermediate Similarity	NPC216297
0.8309	Intermediate Similarity	NPC88269
0.8309	Intermediate Similarity	NPC57380
0.8309	Intermediate Similarity	NPC105456
0.8309	Intermediate Similarity	NPC139634
0.8308	Intermediate Similarity	NPC41263
0.8298	Intermediate Similarity	NPC37139
0.8296	Intermediate Similarity	NPC194579
0.8295	Intermediate Similarity	NPC160499
0.8295	Intermediate Similarity	NPC51037
0.8293	Intermediate Similarity	NPC312800
0.8286	Intermediate Similarity	NPC60389
0.8284	Intermediate Similarity	NPC254832
0.8284	Intermediate Similarity	NPC71108
0.8284	Intermediate Similarity	NPC29317
0.8284	Intermediate Similarity	NPC176102
0.8284	Intermediate Similarity	NPC470844
0.8284	Intermediate Similarity	NPC229638
0.8284	Intermediate Similarity	NPC267539
0.8284	Intermediate Similarity	NPC204257
0.8281	Intermediate Similarity	NPC6888
0.8273	Intermediate Similarity	NPC95123
0.8273	Intermediate Similarity	NPC151607
0.8273	Intermediate Similarity	NPC280404
0.8273	Intermediate Similarity	NPC66404
0.8273	Intermediate Similarity	NPC86373
0.8273	Intermediate Similarity	NPC277426
0.8273	Intermediate Similarity	NPC210425
0.8273	Intermediate Similarity	NPC42540
0.8271	Intermediate Similarity	NPC472591
0.8268	Intermediate Similarity	NPC307174
0.8261	Intermediate Similarity	NPC322112
0.8254	Intermediate Similarity	NPC165197
0.8248	Intermediate Similarity	NPC472601
0.8248	Intermediate Similarity	NPC165172
0.8248	Intermediate Similarity	NPC472600
0.8248	Intermediate Similarity	NPC168471
0.8244	Intermediate Similarity	NPC187907
0.8239	Intermediate Similarity	NPC84142
0.8235	Intermediate Similarity	NPC224584
0.8226	Intermediate Similarity	NPC240664
0.8217	Intermediate Similarity	NPC287473
0.8214	Intermediate Similarity	NPC134621
0.8214	Intermediate Similarity	NPC472034
0.8214	Intermediate Similarity	NPC29577
0.8214	Intermediate Similarity	NPC32470
0.8211	Intermediate Similarity	NPC240163
0.8211	Intermediate Similarity	NPC161304
0.8203	Intermediate Similarity	NPC248786
0.8203	Intermediate Similarity	NPC182646
0.8201	Intermediate Similarity	NPC159721
0.8201	Intermediate Similarity	NPC66593
0.8201	Intermediate Similarity	NPC471731
0.8201	Intermediate Similarity	NPC472006
0.8201	Intermediate Similarity	NPC21873
0.8201	Intermediate Similarity	NPC51106
0.8201	Intermediate Similarity	NPC258307
0.8189	Intermediate Similarity	NPC25168
0.8188	Intermediate Similarity	NPC472604
0.8188	Intermediate Similarity	NPC37530
0.8188	Intermediate Similarity	NPC244923
0.8188	Intermediate Similarity	NPC257003
0.8188	Intermediate Similarity	NPC472603
0.8188	Intermediate Similarity	NPC472605
0.8182	Intermediate Similarity	NPC158866
0.8182	Intermediate Similarity	NPC7569
0.8182	Intermediate Similarity	NPC472891
0.8182	Intermediate Similarity	NPC295036
0.8182	Intermediate Similarity	NPC164762

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 NPC91475 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	989
0.2-0.3	1624
0.3-0.4	2615
0.4-0.5	1873
0.5-0.6	1157
0.6-0.7	375
0.7-0.8	129
0.8-0.85	28
0.85-0.9	8
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8908	High Similarity	NPD9493	Approved
0.8722	High Similarity	NPD970	Clinical (unspecified phase)
0.856	High Similarity	NPD9717	Approved
0.8504	High Similarity	NPD1203	Approved
0.8443	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.839	Intermediate Similarity	NPD74	Approved
0.839	Intermediate Similarity	NPD9266	Approved
0.8321	Intermediate Similarity	NPD411	Approved
0.8305	Intermediate Similarity	NPD9263	Approved
0.8305	Intermediate Similarity	NPD9267	Approved
0.8305	Intermediate Similarity	NPD9264	Approved
0.8296	Intermediate Similarity	NPD2935	Discontinued
0.8271	Intermediate Similarity	NPD447	Suspended
0.8189	Intermediate Similarity	NPD1201	Approved
0.8102	Intermediate Similarity	NPD2346	Discontinued
0.8077	Intermediate Similarity	NPD2797	Approved
0.8077	Intermediate Similarity	NPD1164	Approved
0.8015	Intermediate Similarity	NPD2798	Approved
0.7966	Intermediate Similarity	NPD9261	Approved
0.7939	Intermediate Similarity	NPD1470	Approved
0.7929	Intermediate Similarity	NPD3750	Approved
0.7929	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD2313	Discontinued
0.7899	Intermediate Similarity	NPD1551	Phase 2
0.7895	Intermediate Similarity	NPD6832	Phase 2
0.7874	Intermediate Similarity	NPD9545	Approved
0.7868	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD9281	Approved
0.7826	Intermediate Similarity	NPD2799	Discontinued
0.7826	Intermediate Similarity	NPD4308	Phase 3
0.7794	Intermediate Similarity	NPD1240	Approved
0.7778	Intermediate Similarity	NPD3268	Approved
0.7778	Intermediate Similarity	NPD3764	Approved
0.777	Intermediate Similarity	NPD5404	Approved
0.777	Intermediate Similarity	NPD5406	Approved
0.777	Intermediate Similarity	NPD5405	Approved
0.777	Intermediate Similarity	NPD5408	Approved
0.7744	Intermediate Similarity	NPD1019	Discontinued
0.774	Intermediate Similarity	NPD3226	Approved
0.7727	Intermediate Similarity	NPD1283	Approved
0.771	Intermediate Similarity	NPD1608	Approved
0.7708	Intermediate Similarity	NPD2533	Approved
0.7708	Intermediate Similarity	NPD2534	Approved
0.7708	Intermediate Similarity	NPD2532	Approved
0.7698	Intermediate Similarity	NPD1510	Phase 2
0.7681	Intermediate Similarity	NPD1607	Approved
0.7651	Intermediate Similarity	NPD7819	Suspended
0.7639	Intermediate Similarity	NPD1511	Approved
0.7634	Intermediate Similarity	NPD422	Phase 1
0.7615	Intermediate Similarity	NPD4626	Approved
0.7591	Intermediate Similarity	NPD520	Approved
0.7589	Intermediate Similarity	NPD2344	Approved
0.7571	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3748	Approved
0.7537	Intermediate Similarity	NPD3266	Approved
0.7537	Intermediate Similarity	NPD3267	Approved
0.7536	Intermediate Similarity	NPD4307	Phase 2
0.7534	Intermediate Similarity	NPD1512	Approved
0.75	Intermediate Similarity	NPD1281	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD230	Phase 1
0.7482	Intermediate Similarity	NPD1933	Approved
0.7481	Intermediate Similarity	NPD17	Approved
0.7466	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3225	Approved
0.7447	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7003	Approved
0.7419	Intermediate Similarity	NPD6232	Discontinued
0.7419	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1549	Phase 2
0.741	Intermediate Similarity	NPD943	Approved
0.7405	Intermediate Similarity	NPD5691	Approved
0.7386	Intermediate Similarity	NPD3749	Approved
0.7379	Intermediate Similarity	NPD2309	Approved
0.7361	Intermediate Similarity	NPD1243	Approved
0.7348	Intermediate Similarity	NPD1778	Approved
0.7323	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7768	Phase 2
0.7317	Intermediate Similarity	NPD164	Approved
0.7313	Intermediate Similarity	NPD1481	Phase 2
0.7303	Intermediate Similarity	NPD2801	Approved
0.7293	Intermediate Similarity	NPD3496	Discontinued
0.7279	Intermediate Similarity	NPD6799	Approved
0.7278	Intermediate Similarity	NPD7473	Discontinued
0.7273	Intermediate Similarity	NPD2796	Approved
0.7258	Intermediate Similarity	NPD9697	Approved
0.7255	Intermediate Similarity	NPD3817	Phase 2
0.7255	Intermediate Similarity	NPD5402	Approved
0.7248	Intermediate Similarity	NPD5403	Approved
0.7244	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1535	Discovery
0.7237	Intermediate Similarity	NPD1934	Approved
0.723	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5401	Approved
0.7222	Intermediate Similarity	NPD2182	Approved
0.7222	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1241	Discontinued
0.7206	Intermediate Similarity	NPD1876	Approved
0.719	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6273	Approved
0.7177	Intermediate Similarity	NPD5909	Discontinued
0.7174	Intermediate Similarity	NPD9494	Approved
0.7171	Intermediate Similarity	NPD7411	Suspended
0.7163	Intermediate Similarity	NPD4060	Phase 1
0.7162	Intermediate Similarity	NPD7390	Discontinued
0.7161	Intermediate Similarity	NPD7075	Discontinued
0.7154	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4476	Approved
0.7153	Intermediate Similarity	NPD6100	Approved
0.7153	Intermediate Similarity	NPD6099	Approved
0.7153	Intermediate Similarity	NPD4477	Approved
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1651	Approved
0.7131	Intermediate Similarity	NPD1238	Approved
0.7123	Intermediate Similarity	NPD2800	Approved
0.7123	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1611	Approved
0.7107	Intermediate Similarity	NPD288	Approved
0.7105	Intermediate Similarity	NPD4380	Phase 2
0.7105	Intermediate Similarity	NPD6599	Discontinued
0.7103	Intermediate Similarity	NPD1471	Phase 3
0.7099	Intermediate Similarity	NPD709	Approved
0.7099	Intermediate Similarity	NPD6671	Approved
0.7097	Intermediate Similarity	NPD3882	Suspended
0.7095	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6663	Approved
0.709	Intermediate Similarity	NPD3019	Approved
0.709	Intermediate Similarity	NPD2932	Approved
0.7089	Intermediate Similarity	NPD5711	Approved
0.7089	Intermediate Similarity	NPD5710	Approved
0.7083	Intermediate Similarity	NPD7033	Discontinued
0.7078	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1465	Phase 2
0.7075	Intermediate Similarity	NPD4628	Phase 3
0.7073	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1759	Phase 1
0.7068	Intermediate Similarity	NPD1894	Discontinued
0.7059	Intermediate Similarity	NPD9269	Phase 2
0.705	Intermediate Similarity	NPD5736	Approved
0.7042	Intermediate Similarity	NPD2979	Phase 3
0.7034	Intermediate Similarity	NPD9258	Approved
0.7034	Intermediate Similarity	NPD9256	Approved
0.7032	Intermediate Similarity	NPD4288	Approved
0.7032	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD844	Approved
0.7025	Intermediate Similarity	NPD6959	Discontinued
0.7023	Intermediate Similarity	NPD5951	Approved
0.7021	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1296	Phase 2
0.702	Intermediate Similarity	NPD920	Approved
0.7015	Intermediate Similarity	NPD9268	Approved
0.7015	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5585	Approved
0.7013	Intermediate Similarity	NPD6801	Discontinued
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1578	Phase 2
0.7	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6355	Discontinued
0.6992	Remote Similarity	NPD1758	Phase 1
0.698	Remote Similarity	NPD3300	Phase 2
0.6972	Remote Similarity	NPD8032	Phase 2
0.6959	Remote Similarity	NPD8166	Discontinued
0.6953	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4625	Phase 3
0.695	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3972	Approved
0.6918	Remote Similarity	NPD2438	Suspended
0.6903	Remote Similarity	NPD6844	Discontinued
0.6901	Remote Similarity	NPD6798	Discontinued
0.6899	Remote Similarity	NPD919	Approved
0.6899	Remote Similarity	NPD4750	Phase 3
0.6884	Remote Similarity	NPD4749	Approved
0.6884	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7054	Approved
0.6871	Remote Similarity	NPD5844	Phase 1
0.6867	Remote Similarity	NPD8313	Approved
0.6867	Remote Similarity	NPD8312	Approved
0.6863	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5647	Approved
0.6849	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1196	Approved
0.6845	Remote Similarity	NPD8150	Discontinued
0.6842	Remote Similarity	NPD255	Approved
0.6842	Remote Similarity	NPD256	Approved
0.6839	Remote Similarity	NPD2366	Approved
0.6835	Remote Similarity	NPD955	Approved
0.6831	Remote Similarity	NPD7008	Discontinued
0.6831	Remote Similarity	NPD7095	Approved
0.6829	Remote Similarity	NPD7472	Approved
0.6828	Remote Similarity	NPD6653	Approved
0.6828	Remote Similarity	NPD6651	Approved
0.6825	Remote Similarity	NPD1929	Approved
0.6825	Remote Similarity	NPD1930	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