NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.1
Volume:	284.885
LogP:	2.85
LogD:	3.219
LogS:	-4.991
# Rotatable Bonds:	4
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	2.712
Fsp3:	0.188
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:	-4.694
MDCK Permeability:	1.3465393749356735e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.649
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.202

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	84.5069351196289%
Volume Distribution (VD):	1.054
Pgp-substrate:	12.11799430847168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.402
CYP2C19-substrate:	0.611
CYP2C9-inhibitor:	0.254
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.707
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.677
CYP3A4-substrate:	0.554

ADMET: Excretion

Clearance (CL):	11.081
Half-life (T1/2):	0.642

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.825
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.476
Rat Oral Acute Toxicity:	0.391
Maximum Recommended Daily Dose:	0.5
Skin Sensitization:	0.461
Carcinogencity:	0.921
Eye Corrosion:	0.05
Eye Irritation:	0.801
Respiratory Toxicity:	0.641

Download Data

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

Natural Product: NPC273772

Natural Product ID:	NPC273772
*Common Name:**	XUEBXQXWALAJLA-AATRIKPKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XUEBXQXWALAJLA-AATRIKPKSA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-10(2)5-6-11-13(18-3)9-14(19-4)12-7-8-15(17)20-16(11)12/h5-9H,1H2,2-4H3/b6-5+
SMILES:	C=C(C)/C=C/c1c(cc(c2ccc(=O)oc12)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426663
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	=	12400.0	nM	PMID[570766]

☑ 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 NPC273772 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	428
0.1-0.2	1923
0.2-0.3	5223
0.3-0.4	11561
0.4-0.5	6039
0.5-0.6	4846
0.6-0.7	5963
0.7-0.8	4589
0.8-0.85	1319
0.85-0.9	593
0.9-0.95	165
0.95-1	48

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC109675
0.9915	High Similarity	NPC73413
0.9915	High Similarity	NPC201667
0.9915	High Similarity	NPC27671
0.9829	High Similarity	NPC472518
0.9744	High Similarity	NPC96286
0.9744	High Similarity	NPC248429
0.9664	High Similarity	NPC471828
0.9664	High Similarity	NPC471827
0.9658	High Similarity	NPC144418
0.9587	High Similarity	NPC472519
0.9573	High Similarity	NPC180006
0.9573	High Similarity	NPC235190
0.9573	High Similarity	NPC163200
0.9569	High Similarity	NPC298796
0.9496	High Similarity	NPC173350
0.9496	High Similarity	NPC290605
0.9496	High Similarity	NPC154176
0.9496	High Similarity	NPC50720
0.9483	High Similarity	NPC152306
0.9483	High Similarity	NPC265547
0.9426	High Similarity	NPC185066
0.9421	High Similarity	NPC471826
0.9417	High Similarity	NPC291899
0.9412	High Similarity	NPC257188
0.9412	High Similarity	NPC150214
0.9412	High Similarity	NPC13007
0.9402	High Similarity	NPC281356
0.935	High Similarity	NPC168710
0.9344	High Similarity	NPC243688
0.9333	High Similarity	NPC315807
0.9316	High Similarity	NPC96705
0.931	High Similarity	NPC128633
0.928	High Similarity	NPC14248
0.9274	High Similarity	NPC80170
0.9268	High Similarity	NPC199204
0.9268	High Similarity	NPC157212
0.9262	High Similarity	NPC234109
0.9262	High Similarity	NPC188327
0.9256	High Similarity	NPC111347
0.9206	High Similarity	NPC31849
0.9206	High Similarity	NPC296624
0.9206	High Similarity	NPC207002
0.9206	High Similarity	NPC318400
0.9206	High Similarity	NPC167111
0.9206	High Similarity	NPC133956
0.9206	High Similarity	NPC7526
0.9206	High Similarity	NPC222036
0.9206	High Similarity	NPC471910
0.9187	High Similarity	NPC258567
0.9187	High Similarity	NPC121740
0.9187	High Similarity	NPC224774
0.918	High Similarity	NPC93219
0.918	High Similarity	NPC232692
0.918	High Similarity	NPC202594
0.918	High Similarity	NPC244495
0.9174	High Similarity	NPC143725
0.9134	High Similarity	NPC74655
0.9134	High Similarity	NPC319859
0.9134	High Similarity	NPC195343
0.9134	High Similarity	NPC18804
0.9134	High Similarity	NPC267412
0.9134	High Similarity	NPC166672
0.9134	High Similarity	NPC84894
0.9134	High Similarity	NPC307412
0.9134	High Similarity	NPC100986
0.9134	High Similarity	NPC198381
0.9134	High Similarity	NPC260265
0.9134	High Similarity	NPC47163
0.9134	High Similarity	NPC287182
0.9134	High Similarity	NPC55149
0.9134	High Similarity	NPC164269
0.9134	High Similarity	NPC127888
0.9127	High Similarity	NPC19157
0.912	High Similarity	NPC32463
0.912	High Similarity	NPC113098
0.9113	High Similarity	NPC469453
0.9062	High Similarity	NPC471625
0.9062	High Similarity	NPC471909
0.9062	High Similarity	NPC469675
0.9062	High Similarity	NPC281241
0.9062	High Similarity	NPC472424
0.9062	High Similarity	NPC86892
0.9055	High Similarity	NPC54503
0.9055	High Similarity	NPC55147
0.9048	High Similarity	NPC29734
0.9048	High Similarity	NPC272650
0.9048	High Similarity	NPC267336
0.9032	High Similarity	NPC289316
0.8992	High Similarity	NPC283019
0.8992	High Similarity	NPC160727
0.8992	High Similarity	NPC55615
0.8992	High Similarity	NPC149320
0.8992	High Similarity	NPC26954
0.8992	High Similarity	NPC177281
0.8992	High Similarity	NPC476455
0.8992	High Similarity	NPC38099
0.8992	High Similarity	NPC283331
0.8992	High Similarity	NPC128529
0.8992	High Similarity	NPC471630
0.8984	High Similarity	NPC204353
0.8984	High Similarity	NPC180716
0.8984	High Similarity	NPC326600
0.8984	High Similarity	NPC213173
0.8984	High Similarity	NPC62366
0.8984	High Similarity	NPC50896
0.8984	High Similarity	NPC224475
0.8976	High Similarity	NPC194277
0.8976	High Similarity	NPC469956
0.8976	High Similarity	NPC175159
0.8968	High Similarity	NPC19242
0.896	High Similarity	NPC139595
0.896	High Similarity	NPC60704
0.896	High Similarity	NPC293642
0.8952	High Similarity	NPC101894
0.8952	High Similarity	NPC163248
0.8926	High Similarity	NPC302107
0.8926	High Similarity	NPC319378
0.8923	High Similarity	NPC155963
0.8915	High Similarity	NPC472525
0.8915	High Similarity	NPC61499
0.8915	High Similarity	NPC229128
0.8906	High Similarity	NPC469952
0.8906	High Similarity	NPC469449
0.8906	High Similarity	NPC469955
0.8906	High Similarity	NPC2363
0.8906	High Similarity	NPC163557
0.8898	High Similarity	NPC472517
0.8889	High Similarity	NPC474289
0.8855	High Similarity	NPC151946
0.8855	High Similarity	NPC279573
0.8855	High Similarity	NPC211110
0.8855	High Similarity	NPC253616
0.8852	High Similarity	NPC52247
0.8852	High Similarity	NPC187868
0.8843	High Similarity	NPC247553
0.8837	High Similarity	NPC253574
0.8837	High Similarity	NPC98179
0.8837	High Similarity	NPC131950
0.8828	High Similarity	NPC123954
0.8788	High Similarity	NPC312881
0.8779	High Similarity	NPC153818
0.8779	High Similarity	NPC268081
0.8779	High Similarity	NPC14697
0.8779	High Similarity	NPC232246
0.8779	High Similarity	NPC306365
0.8769	High Similarity	NPC33986
0.876	High Similarity	NPC241341
0.876	High Similarity	NPC472522
0.876	High Similarity	NPC233018
0.876	High Similarity	NPC36437
0.876	High Similarity	NPC472524
0.8722	High Similarity	NPC472523
0.8722	High Similarity	NPC152771
0.8722	High Similarity	NPC183642
0.8722	High Similarity	NPC287286
0.8722	High Similarity	NPC310370
0.8722	High Similarity	NPC195357
0.872	High Similarity	NPC168259
0.8712	High Similarity	NPC270256
0.8712	High Similarity	NPC307883
0.8702	High Similarity	NPC188380
0.8702	High Similarity	NPC167517
0.8702	High Similarity	NPC224543
0.8702	High Similarity	NPC78746
0.8682	High Similarity	NPC137669
0.8672	High Similarity	NPC244799
0.8672	High Similarity	NPC240722
0.8647	High Similarity	NPC71903
0.8647	High Similarity	NPC36414
0.8636	High Similarity	NPC131198
0.8636	High Similarity	NPC471069
0.8636	High Similarity	NPC472516
0.8636	High Similarity	NPC471068
0.8636	High Similarity	NPC184861
0.8636	High Similarity	NPC294456
0.8636	High Similarity	NPC212124
0.8636	High Similarity	NPC225106
0.8636	High Similarity	NPC281014
0.8632	High Similarity	NPC106141
0.8632	High Similarity	NPC473809
0.8615	High Similarity	NPC141822
0.8615	High Similarity	NPC205797
0.8615	High Similarity	NPC142563
0.8615	High Similarity	NPC241165
0.8615	High Similarity	NPC1220
0.8615	High Similarity	NPC291551
0.8605	High Similarity	NPC66430
0.8605	High Similarity	NPC37009
0.8595	High Similarity	NPC471498
0.8595	High Similarity	NPC263754
0.8595	High Similarity	NPC471503
0.8595	High Similarity	NPC183154
0.8594	High Similarity	NPC123127
0.8594	High Similarity	NPC27239
0.8593	High Similarity	NPC183646
0.8593	High Similarity	NPC119640
0.8583	High Similarity	NPC194841
0.8582	High Similarity	NPC138149
0.8582	High Similarity	NPC155552

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 NPC273772 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	987
0.2-0.3	1703
0.3-0.4	2741
0.4-0.5	1789
0.5-0.6	1045
0.6-0.7	338
0.7-0.8	105
0.8-0.85	33
0.85-0.9	13
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8852	High Similarity	NPD422	Phase 1
0.8615	High Similarity	NPD5123	Clinical (unspecified phase)
0.8615	High Similarity	NPD5124	Phase 1
0.8516	High Similarity	NPD1008	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD1296	Phase 2
0.8362	Intermediate Similarity	NPD9697	Approved
0.8244	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5535	Approved
0.8148	Intermediate Similarity	NPD3748	Approved
0.8136	Intermediate Similarity	NPD3134	Approved
0.8067	Intermediate Similarity	NPD1358	Approved
0.8043	Intermediate Similarity	NPD1243	Approved
0.8043	Intermediate Similarity	NPD1652	Phase 2
0.8016	Intermediate Similarity	NPD5691	Approved
0.797	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD2796	Approved
0.7937	Intermediate Similarity	NPD1548	Phase 1
0.7923	Intermediate Similarity	NPD3225	Approved
0.7902	Intermediate Similarity	NPD920	Approved
0.7872	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD2797	Approved
0.7863	Intermediate Similarity	NPD3266	Approved
0.7863	Intermediate Similarity	NPD3267	Approved
0.7857	Intermediate Similarity	NPD3750	Approved
0.782	Intermediate Similarity	NPD4908	Phase 1
0.782	Intermediate Similarity	NPD6832	Phase 2
0.7817	Intermediate Similarity	NPD6799	Approved
0.7812	Intermediate Similarity	NPD4626	Approved
0.7808	Intermediate Similarity	NPD7411	Suspended
0.7786	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6801	Discontinued
0.773	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD3268	Approved
0.7703	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD7819	Suspended
0.7692	Intermediate Similarity	NPD1610	Phase 2
0.7639	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD9717	Approved
0.7619	Intermediate Similarity	NPD6599	Discontinued
0.7615	Intermediate Similarity	NPD3496	Discontinued
0.7603	Intermediate Similarity	NPD1653	Approved
0.76	Intermediate Similarity	NPD7768	Phase 2
0.7591	Intermediate Similarity	NPD4307	Phase 2
0.7571	Intermediate Similarity	NPD1551	Phase 2
0.7557	Intermediate Similarity	NPD1611	Approved
0.7551	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7075	Discontinued
0.754	Intermediate Similarity	NPD1241	Discontinued
0.7537	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.7465	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1549	Phase 2
0.7464	Intermediate Similarity	NPD4060	Phase 1
0.7464	Intermediate Similarity	NPD1240	Approved
0.7463	Intermediate Similarity	NPD1203	Approved
0.745	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2935	Discontinued
0.7444	Intermediate Similarity	NPD4749	Approved
0.7419	Intermediate Similarity	NPD2684	Approved
0.7415	Intermediate Similarity	NPD5403	Approved
0.741	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4340	Discontinued
0.7405	Intermediate Similarity	NPD1778	Approved
0.7397	Intermediate Similarity	NPD5401	Approved
0.7394	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD8651	Approved
0.7376	Intermediate Similarity	NPD4308	Phase 3
0.7376	Intermediate Similarity	NPD1510	Phase 2
0.7376	Intermediate Similarity	NPD7033	Discontinued
0.7361	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1607	Approved
0.7353	Intermediate Similarity	NPD3018	Phase 2
0.7347	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7843	Approved
0.7319	Intermediate Similarity	NPD6798	Discontinued
0.7319	Intermediate Similarity	NPD2313	Discontinued
0.7319	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3817	Phase 2
0.7299	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1091	Approved
0.7286	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD17	Approved
0.7267	Intermediate Similarity	NPD4380	Phase 2
0.7261	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6666	Approved
0.726	Intermediate Similarity	NPD6667	Approved
0.7241	Intermediate Similarity	NPD4628	Phase 3
0.7239	Intermediate Similarity	NPD2981	Phase 2
0.7237	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5844	Phase 1
0.723	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2424	Discontinued
0.7218	Intermediate Similarity	NPD3847	Discontinued
0.7214	Intermediate Similarity	NPD1613	Approved
0.7214	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD846	Approved
0.7213	Intermediate Similarity	NPD940	Approved
0.7211	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD290	Approved
0.7197	Intermediate Similarity	NPD5585	Approved
0.719	Intermediate Similarity	NPD4288	Approved
0.719	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2982	Phase 2
0.7185	Intermediate Similarity	NPD2983	Phase 2
0.7181	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5536	Phase 2
0.7163	Intermediate Similarity	NPD6355	Discontinued
0.7162	Intermediate Similarity	NPD2532	Approved
0.7162	Intermediate Similarity	NPD2534	Approved
0.7162	Intermediate Similarity	NPD2533	Approved
0.7154	Intermediate Similarity	NPD7157	Approved
0.7153	Intermediate Similarity	NPD6005	Phase 3
0.7153	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6002	Phase 3
0.7153	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3027	Phase 3
0.7121	Intermediate Similarity	NPD1894	Discontinued
0.7121	Intermediate Similarity	NPD9545	Approved
0.7115	Intermediate Similarity	NPD5494	Approved
0.7111	Intermediate Similarity	NPD1608	Approved
0.7109	Intermediate Similarity	NPD1139	Approved
0.7109	Intermediate Similarity	NPD1137	Approved
0.7097	Intermediate Similarity	NPD3749	Approved
0.7097	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7212	Phase 2
0.7095	Intermediate Similarity	NPD7213	Phase 3
0.7092	Intermediate Similarity	NPD4140	Approved
0.7087	Intermediate Similarity	NPD5451	Approved
0.7083	Intermediate Similarity	NPD4477	Approved
0.7083	Intermediate Similarity	NPD4476	Approved
0.7078	Intermediate Similarity	NPD5402	Approved
0.7071	Intermediate Similarity	NPD411	Approved
0.7063	Intermediate Similarity	NPD7097	Phase 1
0.7063	Intermediate Similarity	NPD2200	Suspended
0.7055	Intermediate Similarity	NPD2800	Approved
0.7054	Intermediate Similarity	NPD1138	Approved
0.7047	Intermediate Similarity	NPD7447	Phase 1
0.7045	Intermediate Similarity	NPD7644	Approved
0.7042	Intermediate Similarity	NPD447	Suspended
0.7037	Intermediate Similarity	NPD5953	Discontinued
0.7037	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1281	Approved
0.7034	Intermediate Similarity	NPD5763	Approved
0.7034	Intermediate Similarity	NPD5762	Approved
0.7029	Intermediate Similarity	NPD3691	Phase 2
0.7029	Intermediate Similarity	NPD3690	Phase 2
0.7025	Intermediate Similarity	NPD7229	Phase 3
0.7023	Intermediate Similarity	NPD2557	Approved
0.7023	Intermediate Similarity	NPD6671	Approved
0.7023	Intermediate Similarity	NPD6387	Discontinued
0.7021	Intermediate Similarity	NPD8032	Phase 2
0.7021	Intermediate Similarity	NPD6233	Phase 2
0.7019	Intermediate Similarity	NPD7286	Phase 2
0.7013	Intermediate Similarity	NPD2801	Approved
0.7007	Intermediate Similarity	NPD7466	Approved
0.7	Intermediate Similarity	NPD7095	Approved
0.7	Intermediate Similarity	NPD594	Approved
0.7	Intermediate Similarity	NPD592	Approved
0.7	Intermediate Similarity	NPD5283	Phase 1
0.6993	Remote Similarity	NPD6651	Approved
0.6987	Remote Similarity	NPD6971	Discontinued
0.6985	Remote Similarity	NPD3972	Approved
0.698	Remote Similarity	NPD1511	Approved
0.6978	Remote Similarity	NPD2237	Approved
0.6978	Remote Similarity	NPD2861	Phase 2
0.6974	Remote Similarity	NPD3226	Approved
0.6972	Remote Similarity	NPD2979	Phase 3
0.697	Remote Similarity	NPD3596	Phase 2
0.697	Remote Similarity	NPD9493	Approved
0.6966	Remote Similarity	NPD6099	Approved
0.6966	Remote Similarity	NPD6100	Approved
0.6966	Remote Similarity	NPD2862	Discontinued
0.6962	Remote Similarity	NPD1247	Approved
0.6951	Remote Similarity	NPD7549	Discontinued
0.695	Remote Similarity	NPD1048	Approved
0.6948	Remote Similarity	NPD1934	Approved
0.694	Remote Similarity	NPD1651	Approved
0.6939	Remote Similarity	NPD2654	Approved
0.6939	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4359	Approved
0.6934	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2614	Approved
0.6923	Remote Similarity	NPD230	Phase 1
0.6923	Remote Similarity	NPD3882	Suspended
0.6923	Remote Similarity	NPD821	Approved
0.6918	Remote Similarity	NPD6232	Discontinued
0.6918	Remote Similarity	NPD2346	Discontinued
0.6918	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1535	Discovery

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