NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	214.06
Volume:	224.207
LogP:	2.55
LogD:	2.829
LogS:	-2.978
# Rotatable Bonds:	1
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	2.906
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:	-4.681
MDCK Permeability:	1.9857039660564624e-05
Pgp-inhibitor:	0.533
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.301
30% Bioavailability (F30%):	0.482

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	80.32263946533203%
Volume Distribution (VD):	1.014
Pgp-substrate:	5.070084571838379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.556
CYP2C19-inhibitor:	0.959
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.909
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.766
CYP2D6-substrate:	0.847
CYP3A4-inhibitor:	0.352
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	4.4
Half-life (T1/2):	0.657

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.575
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.131
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.565
Skin Sensitization:	0.809
Carcinogencity:	0.813
Eye Corrosion:	0.319
Eye Irritation:	0.97
Respiratory Toxicity:	0.374

Download Data

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

Natural Product: NPC181715

Natural Product ID:	NPC181715
*Common Name:**	8-Hydroxycapillarin
IUPAC Name:	3-but-2-ynyl-8-hydroxyisochromen-1-one
Synonyms:	8-Hydroxycapillarin
Standard InCHIKey:	GWACCTLVSACUOC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10O3/c1-2-3-6-10-8-9-5-4-7-11(14)12(9)13(15)16-10/h4-5,7-8,14H,6H2,1H3
SMILES:	CC#CCc1cc2cccc(c2c(=O)o1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451484
PubChem CID:	44575587
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	1
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	100.0	ug.mL-1	PMID[518734]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	102.0	ug ml-1	PMID[518734]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	2.0	ug.mL-1	PMID[518734]

☑ 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 NPC181715 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	376
0.1-0.2	1758
0.2-0.3	4561
0.3-0.4	11061
0.4-0.5	7128
0.5-0.6	4506
0.6-0.7	6249
0.7-0.8	5847
0.8-0.85	1010
0.85-0.9	179
0.9-0.95	19
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC91475
0.975	High Similarity	NPC265910
0.9106	High Similarity	NPC46634
0.9083	High Similarity	NPC125252
0.8915	High Similarity	NPC470831
0.8915	High Similarity	NPC214702
0.8855	High Similarity	NPC175943
0.879	High Similarity	NPC159760
0.879	High Similarity	NPC179092
0.879	High Similarity	NPC35856
0.879	High Similarity	NPC178395
0.879	High Similarity	NPC301987
0.879	High Similarity	NPC222876
0.879	High Similarity	NPC244994
0.879	High Similarity	NPC272454
0.879	High Similarity	NPC115188
0.879	High Similarity	NPC26433
0.879	High Similarity	NPC292665
0.878	High Similarity	NPC233165
0.878	High Similarity	NPC184579
0.8769	High Similarity	NPC7012
0.872	High Similarity	NPC198336
0.8699	High Similarity	NPC94637
0.8689	High Similarity	NPC128825
0.8651	High Similarity	NPC283514
0.8651	High Similarity	NPC244351
0.8647	High Similarity	NPC27407
0.8647	High Similarity	NPC142027
0.8636	High Similarity	NPC43627
0.8629	High Similarity	NPC328459
0.8629	High Similarity	NPC90522
0.8582	High Similarity	NPC50455
0.8582	High Similarity	NPC291454
0.8571	High Similarity	NPC474097
0.8561	High Similarity	NPC470160
0.856	High Similarity	NPC233282
0.856	High Similarity	NPC72977
0.854	High Similarity	NPC158634
0.8529	High Similarity	NPC32360
0.8529	High Similarity	NPC268052
0.8529	High Similarity	NPC134969
0.8519	High Similarity	NPC62907
0.8516	High Similarity	NPC470162
0.8516	High Similarity	NPC470163
0.8504	High Similarity	NPC217756
0.8496	Intermediate Similarity	NPC153783
0.8485	Intermediate Similarity	NPC219892
0.8485	Intermediate Similarity	NPC189823
0.8462	Intermediate Similarity	NPC71525
0.8456	Intermediate Similarity	NPC126739
0.8456	Intermediate Similarity	NPC197666
0.845	Intermediate Similarity	NPC167055
0.845	Intermediate Similarity	NPC4164
0.845	Intermediate Similarity	NPC240744
0.8444	Intermediate Similarity	NPC235115
0.8409	Intermediate Similarity	NPC473271
0.8406	Intermediate Similarity	NPC149533
0.8394	Intermediate Similarity	NPC247409
0.8394	Intermediate Similarity	NPC92655
0.8387	Intermediate Similarity	NPC477453
0.8382	Intermediate Similarity	NPC261292
0.8382	Intermediate Similarity	NPC301915
0.8382	Intermediate Similarity	NPC135837
0.8372	Intermediate Similarity	NPC236189
0.837	Intermediate Similarity	NPC180905
0.837	Intermediate Similarity	NPC182496
0.837	Intermediate Similarity	NPC298900
0.8359	Intermediate Similarity	NPC311219
0.8321	Intermediate Similarity	NPC61590
0.8321	Intermediate Similarity	NPC33144
0.8321	Intermediate Similarity	NPC221104
0.8321	Intermediate Similarity	NPC478200
0.8321	Intermediate Similarity	NPC470841
0.8309	Intermediate Similarity	NPC242712
0.8308	Intermediate Similarity	NPC262671
0.8308	Intermediate Similarity	NPC201728
0.8286	Intermediate Similarity	NPC478202
0.8284	Intermediate Similarity	NPC477406
0.8273	Intermediate Similarity	NPC470842
0.8273	Intermediate Similarity	NPC220106
0.8273	Intermediate Similarity	NPC130485
0.8268	Intermediate Similarity	NPC285829
0.8268	Intermediate Similarity	NPC206778
0.8261	Intermediate Similarity	NPC295339
0.8261	Intermediate Similarity	NPC52358
0.8258	Intermediate Similarity	NPC95537
0.8248	Intermediate Similarity	NPC70380
0.8248	Intermediate Similarity	NPC71256
0.824	Intermediate Similarity	NPC108288
0.8231	Intermediate Similarity	NPC193805
0.8227	Intermediate Similarity	NPC257025
0.8226	Intermediate Similarity	NPC81808
0.8222	Intermediate Similarity	NPC289572
0.8222	Intermediate Similarity	NPC200422
0.8222	Intermediate Similarity	NPC157478
0.8222	Intermediate Similarity	NPC295406
0.8214	Intermediate Similarity	NPC82913
0.8214	Intermediate Similarity	NPC250755
0.8214	Intermediate Similarity	NPC474385
0.8214	Intermediate Similarity	NPC314271
0.8214	Intermediate Similarity	NPC105648
0.8201	Intermediate Similarity	NPC158472
0.8201	Intermediate Similarity	NPC155205
0.8189	Intermediate Similarity	NPC472593
0.8188	Intermediate Similarity	NPC94248
0.8188	Intermediate Similarity	NPC472602
0.8188	Intermediate Similarity	NPC191835
0.8188	Intermediate Similarity	NPC212693
0.8182	Intermediate Similarity	NPC269023
0.8182	Intermediate Similarity	NPC99846
0.8182	Intermediate Similarity	NPC100551
0.8175	Intermediate Similarity	NPC158481
0.8175	Intermediate Similarity	NPC217423
0.8169	Intermediate Similarity	NPC312789
0.816	Intermediate Similarity	NPC188907
0.8156	Intermediate Similarity	NPC469542
0.8145	Intermediate Similarity	NPC211421
0.8143	Intermediate Similarity	NPC478201
0.8143	Intermediate Similarity	NPC90411
0.8143	Intermediate Similarity	NPC53649
0.8143	Intermediate Similarity	NPC313123
0.8143	Intermediate Similarity	NPC478217
0.8143	Intermediate Similarity	NPC1704
0.8143	Intermediate Similarity	NPC67650
0.8143	Intermediate Similarity	NPC475730
0.8143	Intermediate Similarity	NPC472035
0.8134	Intermediate Similarity	NPC31539
0.8134	Intermediate Similarity	NPC247477
0.8134	Intermediate Similarity	NPC17840
0.8134	Intermediate Similarity	NPC12694
0.8129	Intermediate Similarity	NPC139634
0.8129	Intermediate Similarity	NPC57380
0.8129	Intermediate Similarity	NPC105456
0.8129	Intermediate Similarity	NPC88269
0.8125	Intermediate Similarity	NPC216297
0.8125	Intermediate Similarity	NPC37139
0.8125	Intermediate Similarity	NPC7151
0.8125	Intermediate Similarity	NPC473662
0.8125	Intermediate Similarity	NPC474874
0.812	Intermediate Similarity	NPC41263
0.8116	Intermediate Similarity	NPC194579
0.8112	Intermediate Similarity	NPC60389
0.8106	Intermediate Similarity	NPC51037
0.8106	Intermediate Similarity	NPC160499
0.8102	Intermediate Similarity	NPC267539
0.8102	Intermediate Similarity	NPC229638
0.8102	Intermediate Similarity	NPC470844
0.8102	Intermediate Similarity	NPC71108
0.8102	Intermediate Similarity	NPC176102
0.8102	Intermediate Similarity	NPC29317
0.8102	Intermediate Similarity	NPC204257
0.8102	Intermediate Similarity	NPC254832
0.8099	Intermediate Similarity	NPC42540
0.8099	Intermediate Similarity	NPC66404
0.8099	Intermediate Similarity	NPC280404
0.8099	Intermediate Similarity	NPC95123
0.8099	Intermediate Similarity	NPC86373
0.8099	Intermediate Similarity	NPC277426
0.8099	Intermediate Similarity	NPC210425
0.8099	Intermediate Similarity	NPC151607
0.8095	Intermediate Similarity	NPC312800
0.8092	Intermediate Similarity	NPC6888
0.8088	Intermediate Similarity	NPC472591
0.8085	Intermediate Similarity	NPC322112
0.808	Intermediate Similarity	NPC474685
0.8077	Intermediate Similarity	NPC307174
0.8071	Intermediate Similarity	NPC168471
0.8071	Intermediate Similarity	NPC165172
0.8071	Intermediate Similarity	NPC472600
0.8071	Intermediate Similarity	NPC472601
0.8069	Intermediate Similarity	NPC84142
0.8062	Intermediate Similarity	NPC165197
0.806	Intermediate Similarity	NPC187907
0.8042	Intermediate Similarity	NPC134621
0.8042	Intermediate Similarity	NPC472034
0.8042	Intermediate Similarity	NPC32470
0.8042	Intermediate Similarity	NPC29577
0.8033	Intermediate Similarity	NPC224584
0.8031	Intermediate Similarity	NPC240664
0.803	Intermediate Similarity	NPC287473
0.8028	Intermediate Similarity	NPC471731
0.8028	Intermediate Similarity	NPC472006
0.8028	Intermediate Similarity	NPC21873
0.8028	Intermediate Similarity	NPC258307
0.8028	Intermediate Similarity	NPC159721
0.8028	Intermediate Similarity	NPC51106
0.8028	Intermediate Similarity	NPC66593
0.8016	Intermediate Similarity	NPC161304
0.8016	Intermediate Similarity	NPC240163
0.8015	Intermediate Similarity	NPC248786
0.8015	Intermediate Similarity	NPC182646
0.8014	Intermediate Similarity	NPC472891
0.8014	Intermediate Similarity	NPC257003
0.8014	Intermediate Similarity	NPC164762
0.8014	Intermediate Similarity	NPC472604
0.8014	Intermediate Similarity	NPC472603
0.8014	Intermediate Similarity	NPC472605
0.8014	Intermediate Similarity	NPC158866
0.8014	Intermediate Similarity	NPC295036
0.8014	Intermediate Similarity	NPC37530

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 NPC181715 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	998
0.2-0.3	1620
0.3-0.4	2709
0.4-0.5	1860
0.5-0.6	1108
0.6-0.7	352
0.7-0.8	127
0.8-0.85	16
0.85-0.9	7
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8689	High Similarity	NPD9493	Approved
0.8529	High Similarity	NPD970	Clinical (unspecified phase)
0.8359	Intermediate Similarity	NPD9717	Approved
0.8308	Intermediate Similarity	NPD1203	Approved
0.824	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD74	Approved
0.8182	Intermediate Similarity	NPD9266	Approved
0.8134	Intermediate Similarity	NPD411	Approved
0.8116	Intermediate Similarity	NPD2935	Discontinued
0.8099	Intermediate Similarity	NPD9264	Approved
0.8099	Intermediate Similarity	NPD9267	Approved
0.8099	Intermediate Similarity	NPD9263	Approved
0.8088	Intermediate Similarity	NPD447	Suspended
0.8	Intermediate Similarity	NPD1201	Approved
0.7929	Intermediate Similarity	NPD2346	Discontinued
0.7895	Intermediate Similarity	NPD2797	Approved
0.7895	Intermediate Similarity	NPD1164	Approved
0.7836	Intermediate Similarity	NPD2798	Approved
0.7769	Intermediate Similarity	NPD9261	Approved
0.7762	Intermediate Similarity	NPD3750	Approved
0.7762	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD1470	Approved
0.7737	Intermediate Similarity	NPD2313	Discontinued
0.773	Intermediate Similarity	NPD1551	Phase 2
0.7721	Intermediate Similarity	NPD6832	Phase 2
0.7698	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9545	Approved
0.766	Intermediate Similarity	NPD4308	Phase 3
0.766	Intermediate Similarity	NPD2799	Discontinued
0.7656	Intermediate Similarity	NPD9281	Approved
0.7626	Intermediate Similarity	NPD1240	Approved
0.7609	Intermediate Similarity	NPD3268	Approved
0.7609	Intermediate Similarity	NPD3764	Approved
0.7606	Intermediate Similarity	NPD5405	Approved
0.7606	Intermediate Similarity	NPD5406	Approved
0.7606	Intermediate Similarity	NPD5404	Approved
0.7606	Intermediate Similarity	NPD5408	Approved
0.7584	Intermediate Similarity	NPD3226	Approved
0.7574	Intermediate Similarity	NPD1019	Discontinued
0.7556	Intermediate Similarity	NPD1283	Approved
0.7551	Intermediate Similarity	NPD2532	Approved
0.7551	Intermediate Similarity	NPD2533	Approved
0.7551	Intermediate Similarity	NPD2534	Approved
0.7537	Intermediate Similarity	NPD1608	Approved
0.7535	Intermediate Similarity	NPD1510	Phase 2
0.7518	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD7819	Suspended
0.7483	Intermediate Similarity	NPD1511	Approved
0.7463	Intermediate Similarity	NPD422	Phase 1
0.7444	Intermediate Similarity	NPD4626	Approved
0.7431	Intermediate Similarity	NPD2344	Approved
0.7429	Intermediate Similarity	NPD520	Approved
0.7413	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3748	Approved
0.7383	Intermediate Similarity	NPD1512	Approved
0.7376	Intermediate Similarity	NPD4307	Phase 2
0.7372	Intermediate Similarity	NPD3267	Approved
0.7372	Intermediate Similarity	NPD3266	Approved
0.7351	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1281	Approved
0.7333	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1933	Approved
0.7324	Intermediate Similarity	NPD230	Phase 1
0.7315	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD17	Approved
0.731	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3225	Approved
0.7292	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7003	Approved
0.7278	Intermediate Similarity	NPD6232	Discontinued
0.726	Intermediate Similarity	NPD1549	Phase 2
0.7254	Intermediate Similarity	NPD943	Approved
0.7244	Intermediate Similarity	NPD3749	Approved
0.7244	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5691	Approved
0.723	Intermediate Similarity	NPD2309	Approved
0.7211	Intermediate Similarity	NPD1243	Approved
0.7185	Intermediate Similarity	NPD1778	Approved
0.7179	Intermediate Similarity	NPD7768	Phase 2
0.7161	Intermediate Similarity	NPD2801	Approved
0.7154	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD164	Approved
0.7133	Intermediate Similarity	NPD6799	Approved
0.7132	Intermediate Similarity	NPD3496	Discontinued
0.7123	Intermediate Similarity	NPD2796	Approved
0.7115	Intermediate Similarity	NPD5402	Approved
0.7115	Intermediate Similarity	NPD3817	Phase 2
0.7105	Intermediate Similarity	NPD5403	Approved
0.7097	Intermediate Similarity	NPD1934	Approved
0.7087	Intermediate Similarity	NPD9697	Approved
0.7086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5401	Approved
0.708	Intermediate Similarity	NPD1535	Discovery
0.7077	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2182	Approved
0.7051	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1876	Approved
0.7045	Intermediate Similarity	NPD1241	Discontinued
0.7039	Intermediate Similarity	NPD6273	Approved
0.7032	Intermediate Similarity	NPD7411	Suspended
0.7025	Intermediate Similarity	NPD7075	Discontinued
0.7021	Intermediate Similarity	NPD9494	Approved
0.702	Intermediate Similarity	NPD7390	Discontinued
0.7014	Intermediate Similarity	NPD4060	Phase 1
0.7008	Intermediate Similarity	NPD5909	Discontinued
0.7007	Intermediate Similarity	NPD4477	Approved
0.7007	Intermediate Similarity	NPD4476	Approved
0.7007	Intermediate Similarity	NPD6100	Approved
0.7007	Intermediate Similarity	NPD6099	Approved
0.6993	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1651	Approved
0.698	Remote Similarity	NPD2800	Approved
0.698	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6599	Discontinued
0.6968	Remote Similarity	NPD4380	Phase 2
0.6962	Remote Similarity	NPD3882	Suspended
0.696	Remote Similarity	NPD1238	Approved
0.6959	Remote Similarity	NPD6005	Phase 3
0.6959	Remote Similarity	NPD6004	Phase 3
0.6959	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6002	Phase 3
0.6959	Remote Similarity	NPD1471	Phase 3
0.6957	Remote Similarity	NPD1611	Approved
0.6957	Remote Similarity	NPD5711	Approved
0.6957	Remote Similarity	NPD5710	Approved
0.6954	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6663	Approved
0.6943	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1465	Phase 2
0.694	Remote Similarity	NPD709	Approved
0.694	Remote Similarity	NPD6671	Approved
0.6939	Remote Similarity	NPD7033	Discontinued
0.6935	Remote Similarity	NPD288	Approved
0.6934	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2932	Approved
0.6934	Remote Similarity	NPD3019	Approved
0.6933	Remote Similarity	NPD4628	Phase 3
0.6912	Remote Similarity	NPD1759	Phase 1
0.6912	Remote Similarity	NPD1894	Discontinued
0.6906	Remote Similarity	NPD9269	Phase 2
0.6905	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5736	Approved
0.6899	Remote Similarity	NPD4288	Approved
0.6899	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2979	Phase 3
0.6894	Remote Similarity	NPD6959	Discontinued
0.6883	Remote Similarity	NPD920	Approved
0.6879	Remote Similarity	NPD6801	Discontinued
0.6875	Remote Similarity	NPD1296	Phase 2
0.6875	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5951	Approved
0.6863	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1578	Phase 2
0.6861	Remote Similarity	NPD5585	Approved
0.6861	Remote Similarity	NPD9268	Approved
0.686	Remote Similarity	NPD9258	Approved
0.686	Remote Similarity	NPD9256	Approved
0.6855	Remote Similarity	NPD844	Approved
0.6849	Remote Similarity	NPD6355	Discontinued
0.6842	Remote Similarity	NPD3300	Phase 2
0.6838	Remote Similarity	NPD1758	Phase 1
0.6828	Remote Similarity	NPD8032	Phase 2
0.6821	Remote Similarity	NPD8166	Discontinued
0.6813	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4625	Phase 3
0.6794	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3972	Approved
0.6779	Remote Similarity	NPD2438	Suspended
0.6772	Remote Similarity	NPD6844	Discontinued
0.677	Remote Similarity	NPD919	Approved
0.6759	Remote Similarity	NPD6798	Discontinued
0.675	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7054	Approved
0.6747	Remote Similarity	NPD5844	Phase 1
0.6746	Remote Similarity	NPD8312	Approved
0.6746	Remote Similarity	NPD8313	Approved
0.6742	Remote Similarity	NPD4750	Phase 3
0.6738	Remote Similarity	NPD4749	Approved
0.6738	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD8150	Discontinued
0.6713	Remote Similarity	NPD5647	Approved
0.6711	Remote Similarity	NPD1196	Approved
0.6711	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2366	Approved
0.6708	Remote Similarity	NPD955	Approved
0.6707	Remote Similarity	NPD7472	Approved
0.6691	Remote Similarity	NPD255	Approved
0.6691	Remote Similarity	NPD256	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