NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.07
Volume:	244.424
LogP:	1.032
LogD:	1.188
LogS:	-2.38
# Rotatable Bonds:	4
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.606
Synthetic Accessibility Score:	2.525
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.676
MDCK Permeability:	2.4349596060346812e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.488
Plasma Protein Binding (PPB):	62.5576171875%
Volume Distribution (VD):	1.159
Pgp-substrate:	34.09990310668945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.084
CYP2C19-substrate:	0.383
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.81
CYP2D6-inhibitor:	0.187
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	10.557
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.873
Drug-inuced Liver Injury (DILI):	0.847
AMES Toxicity:	0.444
Rat Oral Acute Toxicity:	0.533
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.846
Carcinogencity:	0.501
Eye Corrosion:	0.023
Eye Irritation:	0.138
Respiratory Toxicity:	0.814

Download Data

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

Natural Product: NPC472517

Natural Product ID:	NPC472517
*Common Name:**	QRXWQDFUTLGHRQ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QRXWQDFUTLGHRQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H12O5/c1-16-10-7-11(17-2)9(5-6-14)13-8(10)3-4-12(15)18-13/h3-4,6-7H,5H2,1-2H3
SMILES:	O=CCc1c(OC)cc(c2c1oc(=O)cc2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426670
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins 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
NPO33003	murraya alata	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25621853]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	13800.0	nM	PMID[550137]

☑ 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 NPC472517 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	407
0.1-0.2	1953
0.2-0.3	5524
0.3-0.4	11244
0.4-0.5	6467
0.5-0.6	4944
0.6-0.7	5505
0.7-0.8	4895
0.8-0.85	1209
0.85-0.9	435
0.9-0.95	106
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.992	High Similarity	NPC175159
0.9385	High Similarity	NPC229128
0.938	High Similarity	NPC55147
0.938	High Similarity	NPC54503
0.9291	High Similarity	NPC472519
0.9098	High Similarity	NPC472516
0.9048	High Similarity	NPC472518
0.904	High Similarity	NPC144418
0.9023	High Similarity	NPC104796
0.8986	High Similarity	NPC208584
0.8976	High Similarity	NPC73413
0.8976	High Similarity	NPC201667
0.8968	High Similarity	NPC248429
0.8968	High Similarity	NPC96286
0.8947	High Similarity	NPC61499
0.8906	High Similarity	NPC471827
0.8906	High Similarity	NPC471828
0.8905	High Similarity	NPC229916
0.8898	High Similarity	NPC109675
0.8898	High Similarity	NPC154176
0.8898	High Similarity	NPC273772
0.8898	High Similarity	NPC290605
0.8898	High Similarity	NPC173350
0.8897	High Similarity	NPC310370
0.8897	High Similarity	NPC472515
0.8897	High Similarity	NPC183642
0.8889	High Similarity	NPC253616
0.8889	High Similarity	NPC221046
0.8857	High Similarity	NPC74539
0.8857	High Similarity	NPC304443
0.8846	High Similarity	NPC199204
0.8837	High Similarity	NPC471826
0.8837	High Similarity	NPC234109
0.8837	High Similarity	NPC188327
0.8828	High Similarity	NPC27671
0.8824	High Similarity	NPC36414
0.8815	High Similarity	NPC268081
0.881	High Similarity	NPC163200
0.88	High Similarity	NPC281356
0.88	High Similarity	NPC298796
0.8779	High Similarity	NPC168710
0.875	High Similarity	NPC332594
0.875	High Similarity	NPC307883
0.8732	High Similarity	NPC88445
0.872	High Similarity	NPC152306
0.872	High Similarity	NPC96705
0.872	High Similarity	NPC265547
0.8712	High Similarity	NPC80170
0.8702	High Similarity	NPC185066
0.8686	High Similarity	NPC71903
0.8682	High Similarity	NPC111347
0.8676	High Similarity	NPC471068
0.8676	High Similarity	NPC471069
0.8672	High Similarity	NPC257188
0.8672	High Similarity	NPC13007
0.8671	High Similarity	NPC191104
0.8667	High Similarity	NPC66705
0.8661	High Similarity	NPC180006
0.8661	High Similarity	NPC235190
0.8657	High Similarity	NPC222036
0.8657	High Similarity	NPC7526
0.8643	High Similarity	NPC295696
0.8643	High Similarity	NPC71739
0.8643	High Similarity	NPC76657
0.8623	High Similarity	NPC136095
0.8623	High Similarity	NPC170812
0.8623	High Similarity	NPC155552
0.8615	High Similarity	NPC93219
0.8615	High Similarity	NPC165556
0.8615	High Similarity	NPC244495
0.8613	High Similarity	NPC471072
0.8613	High Similarity	NPC471070
0.8613	High Similarity	NPC471071
0.8605	High Similarity	NPC315807
0.8603	High Similarity	NPC55615
0.8603	High Similarity	NPC149320
0.8603	High Similarity	NPC283331
0.8603	High Similarity	NPC177281
0.8603	High Similarity	NPC223616
0.8603	High Similarity	NPC128529
0.8603	High Similarity	NPC471630
0.8603	High Similarity	NPC476455
0.8603	High Similarity	NPC283019
0.8603	High Similarity	NPC160727
0.8593	High Similarity	NPC18804
0.8593	High Similarity	NPC319859
0.8593	High Similarity	NPC84894
0.8593	High Similarity	NPC287182
0.8593	High Similarity	NPC55149
0.8593	High Similarity	NPC100986
0.8593	High Similarity	NPC267412
0.8593	High Similarity	NPC166672
0.8593	High Similarity	NPC260265
0.8593	High Similarity	NPC307412
0.8593	High Similarity	NPC127888
0.8593	High Similarity	NPC198381
0.8593	High Similarity	NPC47163
0.8593	High Similarity	NPC164269
0.8593	High Similarity	NPC74655
0.8593	High Similarity	NPC195343
0.8582	High Similarity	NPC246903
0.8582	High Similarity	NPC194277
0.8582	High Similarity	NPC307289
0.8582	High Similarity	NPC14248
0.8571	High Similarity	NPC51146
0.8571	High Similarity	NPC166858
0.8561	High Similarity	NPC470856
0.8561	High Similarity	NPC157212
0.856	High Similarity	NPC128633
0.8538	High Similarity	NPC291899
0.8531	High Similarity	NPC266743
0.8529	High Similarity	NPC281241
0.8529	High Similarity	NPC86892
0.8529	High Similarity	NPC471909
0.8529	High Similarity	NPC472424
0.8529	High Similarity	NPC471625
0.8527	High Similarity	NPC150214
0.8519	High Similarity	NPC229646
0.8519	High Similarity	NPC296624
0.8519	High Similarity	NPC471910
0.8519	High Similarity	NPC207002
0.8519	High Similarity	NPC31849
0.8519	High Similarity	NPC167111
0.8519	High Similarity	NPC133956
0.8519	High Similarity	NPC318400
0.8519	High Similarity	NPC163557
0.8485	Intermediate Similarity	NPC37512
0.8485	Intermediate Similarity	NPC243688
0.8478	Intermediate Similarity	NPC38153
0.8478	Intermediate Similarity	NPC103001
0.8472	Intermediate Similarity	NPC103116
0.8462	Intermediate Similarity	NPC50720
0.8456	Intermediate Similarity	NPC253574
0.8456	Intermediate Similarity	NPC62366
0.8456	Intermediate Similarity	NPC224475
0.8456	Intermediate Similarity	NPC213173
0.8456	Intermediate Similarity	NPC98179
0.8456	Intermediate Similarity	NPC50896
0.8456	Intermediate Similarity	NPC204353
0.8456	Intermediate Similarity	NPC326600
0.8456	Intermediate Similarity	NPC180716
0.8444	Intermediate Similarity	NPC119985
0.8444	Intermediate Similarity	NPC19157
0.8444	Intermediate Similarity	NPC280476
0.844	Intermediate Similarity	NPC313036
0.844	Intermediate Similarity	NPC251372
0.8435	Intermediate Similarity	NPC295608
0.8435	Intermediate Similarity	NPC250769
0.8435	Intermediate Similarity	NPC278010
0.8433	Intermediate Similarity	NPC469929
0.8414	Intermediate Similarity	NPC155882
0.8406	Intermediate Similarity	NPC155963
0.8394	Intermediate Similarity	NPC33986
0.8394	Intermediate Similarity	NPC472525
0.8394	Intermediate Similarity	NPC469675
0.8392	Intermediate Similarity	NPC190572
0.8369	Intermediate Similarity	NPC254010
0.8367	Intermediate Similarity	NPC131725
0.8358	Intermediate Similarity	NPC474289
0.8357	Intermediate Similarity	NPC473209
0.8357	Intermediate Similarity	NPC262635
0.8357	Intermediate Similarity	NPC472523
0.8357	Intermediate Similarity	NPC473076
0.8346	Intermediate Similarity	NPC121740
0.8346	Intermediate Similarity	NPC224774
0.8346	Intermediate Similarity	NPC49852
0.8346	Intermediate Similarity	NPC258567
0.8346	Intermediate Similarity	NPC475496
0.8346	Intermediate Similarity	NPC289316
0.8345	Intermediate Similarity	NPC151946
0.8345	Intermediate Similarity	NPC73078
0.8345	Intermediate Similarity	NPC211110
0.8345	Intermediate Similarity	NPC319870
0.8345	Intermediate Similarity	NPC327612
0.8345	Intermediate Similarity	NPC148738
0.8333	Intermediate Similarity	NPC202594
0.8333	Intermediate Similarity	NPC38099
0.8333	Intermediate Similarity	NPC78746
0.8333	Intermediate Similarity	NPC60667
0.8333	Intermediate Similarity	NPC46869
0.8333	Intermediate Similarity	NPC188380
0.8333	Intermediate Similarity	NPC26954
0.8333	Intermediate Similarity	NPC224543
0.8333	Intermediate Similarity	NPC232692
0.8322	Intermediate Similarity	NPC171656
0.8322	Intermediate Similarity	NPC269495
0.8322	Intermediate Similarity	NPC270044
0.8321	Intermediate Similarity	NPC143725
0.8309	Intermediate Similarity	NPC469956
0.8308	Intermediate Similarity	NPC52247
0.8308	Intermediate Similarity	NPC187868
0.8296	Intermediate Similarity	NPC113098
0.8296	Intermediate Similarity	NPC32463
0.8286	Intermediate Similarity	NPC312881
0.8284	Intermediate Similarity	NPC139595
0.8284	Intermediate Similarity	NPC293642
0.8284	Intermediate Similarity	NPC473907
0.8284	Intermediate Similarity	NPC2401
0.8284	Intermediate Similarity	NPC60704
0.8284	Intermediate Similarity	NPC469453

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 NPC472517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	1021
0.2-0.3	1872
0.3-0.4	2702
0.4-0.5	1812
0.5-0.6	929
0.6-0.7	299
0.7-0.8	95
0.8-0.85	31
0.85-0.9	9
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8857	High Similarity	NPD920	Approved
0.8582	High Similarity	NPD642	Clinical (unspecified phase)
0.8571	High Similarity	NPD1296	Phase 2
0.8571	High Similarity	NPD643	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD1243	Approved
0.8333	Intermediate Similarity	NPD3748	Approved
0.8308	Intermediate Similarity	NPD422	Phase 1
0.8296	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD919	Approved
0.8143	Intermediate Similarity	NPD1551	Phase 2
0.8143	Intermediate Similarity	NPD2796	Approved
0.8054	Intermediate Similarity	NPD6801	Discontinued
0.8042	Intermediate Similarity	NPD3750	Approved
0.8031	Intermediate Similarity	NPD1241	Discontinued
0.8015	Intermediate Similarity	NPD6832	Phase 2
0.8	Intermediate Similarity	NPD6799	Approved
0.7987	Intermediate Similarity	NPD7411	Suspended
0.7986	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD5124	Phase 1
0.7972	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD3266	Approved
0.7926	Intermediate Similarity	NPD3267	Approved
0.7902	Intermediate Similarity	NPD1549	Phase 2
0.7881	Intermediate Similarity	NPD7819	Suspended
0.7881	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1019	Discontinued
0.7836	Intermediate Similarity	NPD9717	Approved
0.7832	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD1510	Phase 2
0.78	Intermediate Similarity	NPD6599	Discontinued
0.7794	Intermediate Similarity	NPD2797	Approved
0.7793	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD4307	Phase 2
0.7786	Intermediate Similarity	NPD1240	Approved
0.7778	Intermediate Similarity	NPD7768	Phase 2
0.7778	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7075	Discontinued
0.7703	Intermediate Similarity	NPD5401	Approved
0.7703	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1247	Approved
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.768	Intermediate Similarity	NPD9697	Approved
0.7676	Intermediate Similarity	NPD1607	Approved
0.7671	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1203	Approved
0.7643	Intermediate Similarity	NPD2313	Discontinued
0.7643	Intermediate Similarity	NPD3268	Approved
0.7632	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD17	Approved
0.7606	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1652	Phase 2
0.76	Intermediate Similarity	NPD5403	Approved
0.7594	Intermediate Similarity	NPD1548	Phase 1
0.7591	Intermediate Similarity	NPD3225	Approved
0.7586	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4308	Phase 3
0.7517	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3817	Phase 2
0.7483	Intermediate Similarity	NPD2800	Approved
0.7467	Intermediate Similarity	NPD2532	Approved
0.7467	Intermediate Similarity	NPD2534	Approved
0.7467	Intermediate Similarity	NPD2533	Approved
0.7463	Intermediate Similarity	NPD9545	Approved
0.7451	Intermediate Similarity	NPD4380	Phase 2
0.7445	Intermediate Similarity	NPD1608	Approved
0.7438	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4628	Phase 3
0.7422	Intermediate Similarity	NPD1358	Approved
0.7419	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5844	Phase 1
0.7407	Intermediate Similarity	NPD7286	Phase 2
0.7407	Intermediate Similarity	NPD5691	Approved
0.7405	Intermediate Similarity	NPD5535	Approved
0.7405	Intermediate Similarity	NPD5494	Approved
0.7394	Intermediate Similarity	NPD6798	Discontinued
0.7394	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3749	Approved
0.7372	Intermediate Similarity	NPD4288	Approved
0.7372	Intermediate Similarity	NPD5402	Approved
0.7372	Intermediate Similarity	NPD1281	Approved
0.7372	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1610	Phase 2
0.7361	Intermediate Similarity	NPD447	Suspended
0.7361	Intermediate Similarity	NPD230	Phase 1
0.7361	Intermediate Similarity	NPD1933	Approved
0.7344	Intermediate Similarity	NPD3134	Approved
0.7333	Intermediate Similarity	NPD1894	Discontinued
0.7329	Intermediate Similarity	NPD7033	Discontinued
0.7317	Intermediate Similarity	NPD5953	Discontinued
0.7308	Intermediate Similarity	NPD1465	Phase 2
0.7285	Intermediate Similarity	NPD1511	Approved
0.7279	Intermediate Similarity	NPD4477	Approved
0.7279	Intermediate Similarity	NPD4476	Approved
0.7278	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3226	Approved
0.7273	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD6559	Discontinued
0.7255	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4908	Phase 1
0.7244	Intermediate Similarity	NPD1934	Approved
0.7241	Intermediate Similarity	NPD6355	Discontinued
0.723	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6004	Phase 3
0.723	Intermediate Similarity	NPD6005	Phase 3
0.723	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6002	Phase 3
0.723	Intermediate Similarity	NPD2346	Discontinued
0.7226	Intermediate Similarity	NPD1778	Approved
0.7215	Intermediate Similarity	NPD3882	Suspended
0.7214	Intermediate Similarity	NPD1283	Approved
0.7205	Intermediate Similarity	NPD7229	Phase 3
0.7197	Intermediate Similarity	NPD2801	Approved
0.7194	Intermediate Similarity	NPD1481	Phase 2
0.7192	Intermediate Similarity	NPD6651	Approved
0.719	Intermediate Similarity	NPD1512	Approved
0.7185	Intermediate Similarity	NPD9493	Approved
0.7172	Intermediate Similarity	NPD2979	Phase 3
0.7161	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4622	Approved
0.7123	Intermediate Similarity	NPD4618	Approved
0.7122	Intermediate Similarity	NPD1535	Discovery
0.7122	Intermediate Similarity	NPD1611	Approved
0.7103	Intermediate Similarity	NPD6233	Phase 2
0.7101	Intermediate Similarity	NPD4626	Approved
0.7099	Intermediate Similarity	NPD6232	Discontinued
0.7097	Intermediate Similarity	NPD1653	Approved
0.7091	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3972	Approved
0.707	Intermediate Similarity	NPD5889	Approved
0.707	Intermediate Similarity	NPD5890	Approved
0.7067	Intermediate Similarity	NPD2424	Discontinued
0.7063	Intermediate Similarity	NPD6971	Discontinued
0.7051	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3496	Discontinued
0.7047	Intermediate Similarity	NPD2438	Suspended
0.7039	Intermediate Similarity	NPD3887	Approved
0.7037	Intermediate Similarity	NPD6959	Discontinued
0.7034	Intermediate Similarity	NPD3764	Approved
0.703	Intermediate Similarity	NPD3818	Discontinued
0.7029	Intermediate Similarity	NPD1651	Approved
0.7027	Intermediate Similarity	NPD5689	Approved
0.7027	Intermediate Similarity	NPD5688	Approved
0.702	Intermediate Similarity	NPD2654	Approved
0.7013	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2353	Approved
0.6993	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2798	Approved
0.6986	Remote Similarity	NPD8032	Phase 2
0.6986	Remote Similarity	NPD4062	Phase 3
0.6981	Remote Similarity	NPD8455	Phase 2
0.6974	Remote Similarity	NPD7003	Approved
0.6972	Remote Similarity	NPD1876	Approved
0.697	Remote Similarity	NPD7473	Discontinued
0.6968	Remote Similarity	NPD5049	Phase 3
0.6968	Remote Similarity	NPD2186	Approved
0.6968	Remote Similarity	NPD6273	Approved
0.6951	Remote Similarity	NPD3926	Phase 2
0.6951	Remote Similarity	NPD5242	Approved
0.6948	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD454	Approved
0.6939	Remote Similarity	NPD3142	Approved
0.6939	Remote Similarity	NPD1613	Approved
0.6939	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3140	Approved
0.6939	Remote Similarity	NPD4060	Phase 1
0.6937	Remote Similarity	NPD5353	Approved
0.6933	Remote Similarity	NPD2531	Phase 2
0.6933	Remote Similarity	NPD6099	Approved
0.6933	Remote Similarity	NPD7199	Phase 2
0.6933	Remote Similarity	NPD6100	Approved
0.6929	Remote Similarity	NPD3847	Discontinued
0.6928	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD37	Approved
0.6913	Remote Similarity	NPD7097	Phase 1
0.6906	Remote Similarity	NPD5585	Approved
0.6905	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6585	Discontinued
0.6897	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2614	Approved
0.6894	Remote Similarity	NPD4965	Approved
0.6894	Remote Similarity	NPD4967	Phase 2
0.6894	Remote Similarity	NPD4966	Approved
0.6892	Remote Similarity	NPD4340	Discontinued
0.689	Remote Similarity	NPD5711	Approved
0.689	Remote Similarity	NPD5710	Approved
0.6887	Remote Similarity	NPD2344	Approved
0.6883	Remote Similarity	NPD6667	Approved
0.6883	Remote Similarity	NPD6666	Approved
0.6859	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD8651	Approved
0.6849	Remote Similarity	NPD4625	Phase 3
0.6848	Remote Similarity	NPD7184	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