NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.04
Volume:	201.042
LogP:	1.534
LogD:	1.351
LogS:	-2.88
# Rotatable Bonds:	1
TPSA:	67.51
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.567
Synthetic Accessibility Score:	2.376
Fsp3:	0.091
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:	-4.72
MDCK Permeability:	1.6677638996043243e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.232
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	89.0715560913086%
Volume Distribution (VD):	0.808
Pgp-substrate:	13.431747436523438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.674
CYP2C19-inhibitor:	0.255
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.219
CYP2C9-substrate:	0.797
CYP2D6-inhibitor:	0.718
CYP2D6-substrate:	0.498
CYP3A4-inhibitor:	0.657
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	11.07
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.549
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.567
Rat Oral Acute Toxicity:	0.272
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.554
Carcinogencity:	0.904
Eye Corrosion:	0.155
Eye Irritation:	0.884
Respiratory Toxicity:	0.749

Download Data

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

Natural Product: NPC332594

Natural Product ID:	NPC332594
*Common Name:**	7-Hydroxy-8-Acetylcoumarin
IUPAC Name:	8-acetyl-7-hydroxychromen-2-one
Synonyms:
Standard InCHIKey:	XWYMACPLPPQCHC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H8O4/c1-6(12)10-8(13)4-2-7-3-5-9(14)15-11(7)10/h2-5,13H,1H3
SMILES:	CC(=O)c1c(ccc2ccc(=O)oc12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446518
PubChem CID:	5411574
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0002908] Hydroxycoumarins [CHEMONTID:0002909] 7-hydroxycoumarins

*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
NPO33433	adina cordifolia	Species	Rubiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[18675491]

☑ 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
IC50	1
Ki	4

Activity Type	# Activity
Individual Protein	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4621	Individual Protein	Zn finger protein	Nicotiana tabacum	Ki	=	61.9	nM	PMID[532702]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	>	100000.0	nM	PMID[532702]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	6510000.0	nM	PMID[532701]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	73.0	nM	PMID[532702]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	>	100000.0	nM	PMID[532702]

☑ 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 NPC332594 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	395
0.1-0.2	1951
0.2-0.3	5251
0.3-0.4	11574
0.4-0.5	5982
0.5-0.6	4671
0.6-0.7	5694
0.7-0.8	4372
0.8-0.85	1636
0.85-0.9	901
0.9-0.95	263
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9403	High Similarity	NPC151113
0.9398	High Similarity	NPC108113
0.9398	High Similarity	NPC93756
0.9348	High Similarity	NPC36181
0.9333	High Similarity	NPC472516
0.9328	High Similarity	NPC125920
0.9286	High Similarity	NPC154217
0.9281	High Similarity	NPC94794
0.9281	High Similarity	NPC196459
0.9281	High Similarity	NPC470296
0.9281	High Similarity	NPC112791
0.9281	High Similarity	NPC188632
0.9281	High Similarity	NPC87609
0.9265	High Similarity	NPC221046
0.9265	High Similarity	NPC474624
0.9265	High Similarity	NPC138047
0.9265	High Similarity	NPC253616
0.9265	High Similarity	NPC131782
0.9259	High Similarity	NPC60667
0.922	High Similarity	NPC180477
0.9214	High Similarity	NPC178627
0.9214	High Similarity	NPC196137
0.9214	High Similarity	NPC1886
0.9214	High Similarity	NPC469935
0.9214	High Similarity	NPC469953
0.9203	High Similarity	NPC261227
0.9203	High Similarity	NPC172986
0.9203	High Similarity	NPC221173
0.9203	High Similarity	NPC270883
0.9197	High Similarity	NPC219584
0.9197	High Similarity	NPC183639
0.9197	High Similarity	NPC470668
0.9197	High Similarity	NPC201395
0.9197	High Similarity	NPC36414
0.9197	High Similarity	NPC199458
0.9197	High Similarity	NPC470669
0.9197	High Similarity	NPC470083
0.9191	High Similarity	NPC268081
0.9191	High Similarity	NPC174999
0.9173	High Similarity	NPC270369
0.9173	High Similarity	NPC5515
0.9149	High Similarity	NPC181388
0.9149	High Similarity	NPC57470
0.9149	High Similarity	NPC470322
0.9137	High Similarity	NPC156590
0.9137	High Similarity	NPC147688
0.9137	High Similarity	NPC64908
0.9137	High Similarity	NPC118840
0.9137	High Similarity	NPC205006
0.9137	High Similarity	NPC470555
0.9137	High Similarity	NPC110969
0.913	High Similarity	NPC303633
0.913	High Similarity	NPC473076
0.913	High Similarity	NPC78913
0.913	High Similarity	NPC96565
0.913	High Similarity	NPC241975
0.913	High Similarity	NPC301217
0.913	High Similarity	NPC220062
0.913	High Similarity	NPC23257
0.913	High Similarity	NPC55018
0.913	High Similarity	NPC19476
0.913	High Similarity	NPC216978
0.913	High Similarity	NPC18260
0.9104	High Similarity	NPC113006
0.9104	High Similarity	NPC31872
0.9104	High Similarity	NPC473584
0.9104	High Similarity	NPC475589
0.9085	High Similarity	NPC297886
0.9085	High Similarity	NPC140120
0.9085	High Similarity	NPC249942
0.9071	High Similarity	NPC11561
0.9071	High Similarity	NPC226636
0.9065	High Similarity	NPC159275
0.9065	High Similarity	NPC471587
0.9065	High Similarity	NPC235239
0.9065	High Similarity	NPC241100
0.9065	High Similarity	NPC305355
0.9065	High Similarity	NPC475680
0.9065	High Similarity	NPC307990
0.9065	High Similarity	NPC16455
0.9065	High Similarity	NPC69769
0.9058	High Similarity	NPC131130
0.9044	High Similarity	NPC172262
0.9037	High Similarity	NPC25937
0.9037	High Similarity	NPC10971
0.9028	High Similarity	NPC151973
0.9023	High Similarity	NPC187907
0.9021	High Similarity	NPC161864
0.9021	High Similarity	NPC469933
0.9021	High Similarity	NPC208303
0.9021	High Similarity	NPC211811
0.9008	High Similarity	NPC93219
0.9008	High Similarity	NPC244495
0.9007	High Similarity	NPC38219
0.9	High Similarity	NPC282300
0.9	High Similarity	NPC3188
0.9	High Similarity	NPC103362
0.8993	High Similarity	NPC471697
0.8993	High Similarity	NPC53181
0.8993	High Similarity	NPC472343
0.8993	High Similarity	NPC139554
0.8993	High Similarity	NPC183642
0.8993	High Similarity	NPC217186
0.8993	High Similarity	NPC310370
0.8993	High Similarity	NPC472515
0.8986	High Similarity	NPC266597
0.8986	High Similarity	NPC103001
0.8986	High Similarity	NPC250266
0.8986	High Similarity	NPC228661
0.8978	High Similarity	NPC101752
0.8978	High Similarity	NPC239495
0.8978	High Similarity	NPC9985
0.8971	High Similarity	NPC50898
0.8971	High Similarity	NPC78540
0.8971	High Similarity	NPC57601
0.8971	High Similarity	NPC223457
0.8971	High Similarity	NPC274121
0.8971	High Similarity	NPC213216
0.8958	High Similarity	NPC469932
0.8958	High Similarity	NPC19238
0.8955	High Similarity	NPC42292
0.8955	High Similarity	NPC307732
0.8944	High Similarity	NPC311741
0.8944	High Similarity	NPC234629
0.8944	High Similarity	NPC206212
0.8944	High Similarity	NPC71184
0.8936	High Similarity	NPC162476
0.8936	High Similarity	NPC293852
0.8936	High Similarity	NPC78803
0.8936	High Similarity	NPC217083
0.8936	High Similarity	NPC299080
0.8936	High Similarity	NPC62840
0.8936	High Similarity	NPC473042
0.8936	High Similarity	NPC214236
0.8936	High Similarity	NPC144499
0.8936	High Similarity	NPC112829
0.8936	High Similarity	NPC470556
0.8936	High Similarity	NPC294432
0.8936	High Similarity	NPC59739
0.8936	High Similarity	NPC200694
0.8929	High Similarity	NPC150522
0.8921	High Similarity	NPC470672
0.8921	High Similarity	NPC470671
0.8921	High Similarity	NPC474487
0.8921	High Similarity	NPC124269
0.8921	High Similarity	NPC474504
0.8913	High Similarity	NPC1486
0.8913	High Similarity	NPC473887
0.8913	High Similarity	NPC12165
0.8913	High Similarity	NPC66349
0.8913	High Similarity	NPC127447
0.8913	High Similarity	NPC47815
0.8913	High Similarity	NPC98115
0.8913	High Similarity	NPC477243
0.8913	High Similarity	NPC156910
0.8913	High Similarity	NPC186838
0.8913	High Similarity	NPC29353
0.8913	High Similarity	NPC124784
0.8913	High Similarity	NPC231772
0.8913	High Similarity	NPC150399
0.8913	High Similarity	NPC274109
0.8913	High Similarity	NPC13408
0.8913	High Similarity	NPC234133
0.8913	High Similarity	NPC194281
0.8913	High Similarity	NPC41461
0.8913	High Similarity	NPC477242
0.8913	High Similarity	NPC477244
0.8913	High Similarity	NPC249606
0.8913	High Similarity	NPC25287
0.8913	High Similarity	NPC168105
0.8905	High Similarity	NPC164136
0.8905	High Similarity	NPC248872
0.8905	High Similarity	NPC66705
0.8897	High Similarity	NPC158866
0.8897	High Similarity	NPC229646
0.8897	High Similarity	NPC55147
0.8897	High Similarity	NPC180351
0.8897	High Similarity	NPC474735
0.8889	High Similarity	NPC137264
0.8889	High Similarity	NPC250057
0.8889	High Similarity	NPC37139
0.8881	High Similarity	NPC153758
0.8881	High Similarity	NPC473019
0.8881	High Similarity	NPC197425
0.8881	High Similarity	NPC230818
0.8881	High Similarity	NPC474289
0.8873	High Similarity	NPC242100
0.8873	High Similarity	NPC169591
0.8873	High Similarity	NPC293053
0.8873	High Similarity	NPC150408
0.8873	High Similarity	NPC310130
0.8873	High Similarity	NPC9117
0.8873	High Similarity	NPC106985
0.8873	High Similarity	NPC257097
0.8873	High Similarity	NPC184738
0.8873	High Similarity	NPC190637
0.8873	High Similarity	NPC33653
0.8873	High Similarity	NPC307895
0.8873	High Similarity	NPC149026
0.8873	High Similarity	NPC474939

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 NPC332594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	1009
0.2-0.3	1710
0.3-0.4	2693
0.4-0.5	1850
0.5-0.6	1026
0.6-0.7	309
0.7-0.8	103
0.8-0.85	37
0.85-0.9	21
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8857	High Similarity	NPD1243	Approved
0.8824	High Similarity	NPD1240	Approved
0.8811	High Similarity	NPD4378	Clinical (unspecified phase)
0.8811	High Similarity	NPD7410	Clinical (unspecified phase)
0.8794	High Similarity	NPD3750	Approved
0.8786	High Similarity	NPD1549	Phase 2
0.8779	High Similarity	NPD9717	Approved
0.8722	High Similarity	NPD1203	Approved
0.8714	High Similarity	NPD1552	Clinical (unspecified phase)
0.8714	High Similarity	NPD1550	Clinical (unspecified phase)
0.8707	High Similarity	NPD7411	Suspended
0.8705	High Similarity	NPD1510	Phase 2
0.8702	High Similarity	NPD422	Phase 1
0.8696	High Similarity	NPD1607	Approved
0.8652	High Similarity	NPD970	Clinical (unspecified phase)
0.8643	High Similarity	NPD1551	Phase 2
0.8562	High Similarity	NPD920	Approved
0.8543	High Similarity	NPD7075	Discontinued
0.8542	High Similarity	NPD643	Clinical (unspecified phase)
0.8531	High Similarity	NPD1878	Clinical (unspecified phase)
0.8523	High Similarity	NPD6801	Discontinued
0.8483	Intermediate Similarity	NPD6799	Approved
0.8477	Intermediate Similarity	NPD7768	Phase 2
0.8467	Intermediate Similarity	NPD7819	Suspended
0.8467	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD3748	Approved
0.844	Intermediate Similarity	NPD2799	Discontinued
0.8425	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD2313	Discontinued
0.838	Intermediate Similarity	NPD2796	Approved
0.838	Intermediate Similarity	NPD2935	Discontinued
0.8356	Intermediate Similarity	NPD1511	Approved
0.8333	Intermediate Similarity	NPD2800	Approved
0.8333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD3749	Approved
0.8273	Intermediate Similarity	NPD1296	Phase 2
0.8267	Intermediate Similarity	NPD6599	Discontinued
0.8267	Intermediate Similarity	NPD4380	Phase 2
0.8243	Intermediate Similarity	NPD1512	Approved
0.8224	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD5403	Approved
0.8176	Intermediate Similarity	NPD5401	Approved
0.817	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD411	Approved
0.8129	Intermediate Similarity	NPD919	Approved
0.8129	Intermediate Similarity	NPD6832	Phase 2
0.8106	Intermediate Similarity	NPD9493	Approved
0.8099	Intermediate Similarity	NPD447	Suspended
0.8079	Intermediate Similarity	NPD3226	Approved
0.8065	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4308	Phase 3
0.8054	Intermediate Similarity	NPD2532	Approved
0.8054	Intermediate Similarity	NPD2534	Approved
0.8054	Intermediate Similarity	NPD2533	Approved
0.8043	Intermediate Similarity	NPD2797	Approved
0.8042	Intermediate Similarity	NPD6651	Approved
0.8039	Intermediate Similarity	NPD1934	Approved
0.8027	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD3268	Approved
0.7987	Intermediate Similarity	NPD2801	Approved
0.7986	Intermediate Similarity	NPD1019	Discontinued
0.7972	Intermediate Similarity	NPD5124	Phase 1
0.7972	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5953	Discontinued
0.795	Intermediate Similarity	NPD7286	Phase 2
0.7945	Intermediate Similarity	NPD2346	Discontinued
0.7935	Intermediate Similarity	NPD3817	Phase 2
0.7885	Intermediate Similarity	NPD3882	Suspended
0.7872	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD9545	Approved
0.7842	Intermediate Similarity	NPD3225	Approved
0.784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2344	Approved
0.7821	Intermediate Similarity	NPD5402	Approved
0.7805	Intermediate Similarity	NPD6559	Discontinued
0.7786	Intermediate Similarity	NPD1164	Approved
0.7786	Intermediate Similarity	NPD3266	Approved
0.7786	Intermediate Similarity	NPD3267	Approved
0.7778	Intermediate Similarity	NPD4307	Phase 2
0.7754	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6232	Discontinued
0.773	Intermediate Similarity	NPD2798	Approved
0.7724	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1548	Phase 1
0.7716	Intermediate Similarity	NPD7473	Discontinued
0.7707	Intermediate Similarity	NPD4288	Approved
0.7688	Intermediate Similarity	NPD6959	Discontinued
0.7687	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3818	Discontinued
0.7667	Intermediate Similarity	NPD4628	Phase 3
0.7658	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD943	Approved
0.7643	Intermediate Similarity	NPD1465	Phase 2
0.7634	Intermediate Similarity	NPD74	Approved
0.7634	Intermediate Similarity	NPD9266	Approved
0.7622	Intermediate Similarity	NPD5844	Phase 1
0.7616	Intermediate Similarity	NPD2309	Approved
0.7612	Intermediate Similarity	NPD1241	Discontinued
0.7603	Intermediate Similarity	NPD230	Phase 1
0.7603	Intermediate Similarity	NPD1933	Approved
0.7578	Intermediate Similarity	NPD1247	Approved
0.7571	Intermediate Similarity	NPD1608	Approved
0.7571	Intermediate Similarity	NPD1481	Phase 2
0.7568	Intermediate Similarity	NPD7033	Discontinued
0.7557	Intermediate Similarity	NPD9263	Approved
0.7557	Intermediate Similarity	NPD9264	Approved
0.7557	Intermediate Similarity	NPD9267	Approved
0.7546	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6166	Phase 2
0.7545	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3764	Approved
0.7516	Intermediate Similarity	NPD5494	Approved
0.7516	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD1535	Discovery
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7483	Intermediate Similarity	NPD1652	Phase 2
0.747	Intermediate Similarity	NPD7074	Phase 3
0.747	Intermediate Similarity	NPD7472	Approved
0.7467	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6797	Phase 2
0.7423	Intermediate Similarity	NPD5711	Approved
0.7423	Intermediate Similarity	NPD5710	Approved
0.7419	Intermediate Similarity	NPD5049	Phase 3
0.7405	Intermediate Similarity	NPD9697	Approved
0.74	Intermediate Similarity	NPD5404	Approved
0.74	Intermediate Similarity	NPD6100	Approved
0.74	Intermediate Similarity	NPD5408	Approved
0.74	Intermediate Similarity	NPD5406	Approved
0.74	Intermediate Similarity	NPD6099	Approved
0.74	Intermediate Similarity	NPD5405	Approved
0.7381	Intermediate Similarity	NPD7251	Discontinued
0.7379	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD2654	Approved
0.7365	Intermediate Similarity	NPD1729	Discontinued
0.7357	Intermediate Similarity	NPD17	Approved
0.7342	Intermediate Similarity	NPD6585	Discontinued
0.7337	Intermediate Similarity	NPD7808	Phase 3
0.732	Intermediate Similarity	NPD7003	Approved
0.7299	Intermediate Similarity	NPD9281	Approved
0.7296	Intermediate Similarity	NPD5889	Approved
0.7296	Intermediate Similarity	NPD5890	Approved
0.7293	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1470	Approved
0.7283	Intermediate Similarity	NPD4287	Approved
0.7279	Intermediate Similarity	NPD6798	Discontinued
0.7278	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2354	Approved
0.7261	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1201	Approved
0.7252	Intermediate Similarity	NPD9261	Approved
0.7237	Intermediate Similarity	NPD6002	Phase 3
0.7237	Intermediate Similarity	NPD6005	Phase 3
0.7237	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6004	Phase 3
0.7237	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1283	Approved
0.7219	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1653	Approved
0.7214	Intermediate Similarity	NPD1894	Discontinued
0.7211	Intermediate Similarity	NPD4625	Phase 3
0.7192	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7390	Discontinued
0.7171	Intermediate Similarity	NPD4476	Approved
0.7171	Intermediate Similarity	NPD4477	Approved
0.717	Intermediate Similarity	NPD7458	Discontinued
0.7169	Intermediate Similarity	NPD3926	Phase 2
0.7162	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5535	Approved
0.7153	Intermediate Similarity	NPD4749	Approved
0.7133	Intermediate Similarity	NPD6355	Discontinued
0.7124	Intermediate Similarity	NPD2353	Approved
0.7124	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1471	Phase 3
0.7119	Intermediate Similarity	NPD4360	Phase 2
0.7119	Intermediate Similarity	NPD4363	Phase 3
0.7114	Intermediate Similarity	NPD520	Approved
0.7113	Intermediate Similarity	NPD1778	Approved
0.7113	Intermediate Similarity	NPD4626	Approved
0.7093	Intermediate Similarity	NPD8312	Approved
0.7093	Intermediate Similarity	NPD8313	Approved
0.7089	Intermediate Similarity	NPD6273	Approved
0.7083	Intermediate Similarity	NPD9269	Phase 2
0.7083	Intermediate Similarity	NPD3972	Approved
0.7081	Intermediate Similarity	NPD2366	Approved
0.7079	Intermediate Similarity	NPD4361	Phase 2
0.7079	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6104	Discontinued
0.7073	Intermediate Similarity	NPD6971	Discontinued
0.7071	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1612	Clinical (unspecified phase)

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