NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	214.1
Volume:	235.349
LogP:	3.852
LogD:	3.695
LogS:	-4.87
# Rotatable Bonds:	3
TPSA:	18.46
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.779
Synthetic Accessibility Score:	1.438
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.564
MDCK Permeability:	2.4061244403128512e-05
Pgp-inhibitor:	0.087
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.701
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.291
Plasma Protein Binding (PPB):	98.54889678955078%
Volume Distribution (VD):	1.403
Pgp-substrate:	2.3890793323516846%

ADMET: Metabolism

CYP1A2-inhibitor:	0.989
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.941
CYP2C19-substrate:	0.383
CYP2C9-inhibitor:	0.603
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.474
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.776
CYP3A4-substrate:	0.329

ADMET: Excretion

Clearance (CL):	9.675
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.157
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.436
AMES Toxicity:	0.388
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.395
Skin Sensitization:	0.924
Carcinogencity:	0.183
Eye Corrosion:	0.598
Eye Irritation:	0.98
Respiratory Toxicity:	0.055

Download Data

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

Natural Product: NPC303521

Natural Product ID:	NPC303521
*Common Name:**	3,5-Dimethoxybiphenyl
IUPAC Name:	1,3-dimethoxy-5-phenylbenzene
Synonyms:	3,5-Dimethoxybiphenyl
Standard InCHIKey:	CQWCDYBZNSNECQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14O2/c1-15-13-8-12(9-14(10-13)16-2)11-6-4-3-5-7-11/h3-10H,1-2H3
SMILES:	COc1cc(OC)cc(c1)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496247
PubChem CID:	11469945
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls 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
NPO20815	Lindera fruticosa	Species	Lauraceae	Eukaryota	roots	n.a.	n.a.	PMID[16724860]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19813743]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	trunk	Jeju island, Korea	2005-Dec	PMID[21420296]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21420296]
NPO20815	Lindera fruticosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4001	Berberis koreana	Species	Berberidaceae	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
IC50	5
Others	1

Activity Type	# Activity
Cell Line	4
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1214	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	43.0	%	PMID[474620]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[474621]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[474621]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[474621]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	10000.0	nM	PMID[474621]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	48100.0	nM	PMID[474620]

☑ 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 NPC303521 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	528
0.1-0.2	1995
0.2-0.3	5874
0.3-0.4	13346
0.4-0.5	3604
0.5-0.6	6778
0.6-0.7	8029
0.7-0.8	2176
0.8-0.85	280
0.85-0.9	57
0.9-0.95	28
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC2682
0.9533	High Similarity	NPC167934
0.9358	High Similarity	NPC244816
0.9358	High Similarity	NPC50521
0.9358	High Similarity	NPC195466
0.9358	High Similarity	NPC221549
0.9327	High Similarity	NPC35543
0.9259	High Similarity	NPC276737
0.9259	High Similarity	NPC22610
0.9238	High Similarity	NPC245115
0.9189	High Similarity	NPC15805
0.9174	High Similarity	NPC53906
0.9151	High Similarity	NPC82016
0.9091	High Similarity	NPC150624
0.9091	High Similarity	NPC141090
0.9065	High Similarity	NPC94045
0.9009	High Similarity	NPC219070
0.9009	High Similarity	NPC127894
0.9009	High Similarity	NPC69261
0.9009	High Similarity	NPC470759
0.9009	High Similarity	NPC474933
0.9009	High Similarity	NPC33270
0.9009	High Similarity	NPC15860
0.9	High Similarity	NPC808
0.8919	High Similarity	NPC114064
0.8899	High Similarity	NPC280606
0.8889	High Similarity	NPC168657
0.885	High Similarity	NPC254625
0.885	High Similarity	NPC475961
0.885	High Similarity	NPC184302
0.8846	High Similarity	NPC300166
0.8807	High Similarity	NPC90520
0.8807	High Similarity	NPC296920
0.8793	High Similarity	NPC84086
0.8783	High Similarity	NPC477886
0.8761	High Similarity	NPC190514
0.875	High Similarity	NPC203113
0.8739	High Similarity	NPC228287
0.8739	High Similarity	NPC180508
0.8718	High Similarity	NPC5796
0.8718	High Similarity	NPC228503
0.8718	High Similarity	NPC206487
0.8718	High Similarity	NPC138248
0.8696	High Similarity	NPC102639
0.8692	High Similarity	NPC164576
0.8679	High Similarity	NPC241224
0.8649	High Similarity	NPC204120
0.8644	High Similarity	NPC278955
0.8644	High Similarity	NPC105718
0.8636	High Similarity	NPC255068
0.8621	High Similarity	NPC476633
0.8584	High Similarity	NPC123948
0.8584	High Similarity	NPC85292
0.8584	High Similarity	NPC229147
0.8584	High Similarity	NPC54507
0.8571	High Similarity	NPC170485
0.8571	High Similarity	NPC223953
0.8547	High Similarity	NPC77789
0.8547	High Similarity	NPC18128
0.8534	High Similarity	NPC472596
0.85	High Similarity	NPC53781
0.85	High Similarity	NPC266555
0.85	High Similarity	NPC473221
0.8496	Intermediate Similarity	NPC185541
0.8496	Intermediate Similarity	NPC464
0.8487	Intermediate Similarity	NPC113495
0.8487	Intermediate Similarity	NPC105031
0.8475	Intermediate Similarity	NPC136319
0.8475	Intermediate Similarity	NPC282496
0.8475	Intermediate Similarity	NPC233526
0.8468	Intermediate Similarity	NPC203924
0.8455	Intermediate Similarity	NPC165386
0.8435	Intermediate Similarity	NPC63010
0.8435	Intermediate Similarity	NPC131118
0.843	Intermediate Similarity	NPC154866
0.843	Intermediate Similarity	NPC215300
0.843	Intermediate Similarity	NPC38017
0.8417	Intermediate Similarity	NPC285725
0.8417	Intermediate Similarity	NPC50683
0.8417	Intermediate Similarity	NPC82299
0.8417	Intermediate Similarity	NPC112571
0.839	Intermediate Similarity	NPC261661
0.839	Intermediate Similarity	NPC41562
0.8381	Intermediate Similarity	NPC470161
0.8378	Intermediate Similarity	NPC106141
0.8364	Intermediate Similarity	NPC75440
0.8362	Intermediate Similarity	NPC172253
0.8362	Intermediate Similarity	NPC226629
0.8362	Intermediate Similarity	NPC59561
0.8348	Intermediate Similarity	NPC471503
0.8348	Intermediate Similarity	NPC471498
0.8347	Intermediate Similarity	NPC471986
0.8347	Intermediate Similarity	NPC127587
0.8347	Intermediate Similarity	NPC46978
0.8333	Intermediate Similarity	NPC203133
0.8333	Intermediate Similarity	NPC221077
0.8333	Intermediate Similarity	NPC233410
0.8333	Intermediate Similarity	NPC57490
0.8333	Intermediate Similarity	NPC475169
0.8333	Intermediate Similarity	NPC116907
0.8333	Intermediate Similarity	NPC298757
0.8333	Intermediate Similarity	NPC105925
0.8333	Intermediate Similarity	NPC251855
0.8333	Intermediate Similarity	NPC117214
0.8333	Intermediate Similarity	NPC472093
0.8333	Intermediate Similarity	NPC193544
0.8333	Intermediate Similarity	NPC208950
0.8333	Intermediate Similarity	NPC17943
0.8319	Intermediate Similarity	NPC121115
0.8319	Intermediate Similarity	NPC197757
0.8319	Intermediate Similarity	NPC228922
0.8318	Intermediate Similarity	NPC100340
0.8318	Intermediate Similarity	NPC143659
0.8305	Intermediate Similarity	NPC193364
0.8305	Intermediate Similarity	NPC75713
0.8291	Intermediate Similarity	NPC471504
0.8291	Intermediate Similarity	NPC473290
0.8279	Intermediate Similarity	NPC207702
0.8279	Intermediate Similarity	NPC82862
0.8279	Intermediate Similarity	NPC283114
0.8279	Intermediate Similarity	NPC149008
0.8279	Intermediate Similarity	NPC222127
0.8276	Intermediate Similarity	NPC474612
0.8264	Intermediate Similarity	NPC186845
0.8264	Intermediate Similarity	NPC9891
0.8264	Intermediate Similarity	NPC88297
0.8264	Intermediate Similarity	NPC76451
0.825	Intermediate Similarity	NPC256015
0.825	Intermediate Similarity	NPC294156
0.825	Intermediate Similarity	NPC140521
0.8241	Intermediate Similarity	NPC12870
0.8241	Intermediate Similarity	NPC24327
0.8235	Intermediate Similarity	NPC302546
0.8226	Intermediate Similarity	NPC282508
0.8226	Intermediate Similarity	NPC471983
0.8226	Intermediate Similarity	NPC149337
0.822	Intermediate Similarity	NPC166759
0.822	Intermediate Similarity	NPC100108
0.822	Intermediate Similarity	NPC277798
0.822	Intermediate Similarity	NPC218753
0.8214	Intermediate Similarity	NPC475852
0.8211	Intermediate Similarity	NPC471519
0.8211	Intermediate Similarity	NPC471518
0.8211	Intermediate Similarity	NPC16577
0.8211	Intermediate Similarity	NPC190144
0.8205	Intermediate Similarity	NPC20674
0.8205	Intermediate Similarity	NPC308217
0.8205	Intermediate Similarity	NPC119949
0.8197	Intermediate Similarity	NPC293054
0.8197	Intermediate Similarity	NPC473093
0.8197	Intermediate Similarity	NPC74817
0.8197	Intermediate Similarity	NPC8050
0.8197	Intermediate Similarity	NPC82679
0.8197	Intermediate Similarity	NPC189248
0.8197	Intermediate Similarity	NPC282000
0.8197	Intermediate Similarity	NPC169474
0.8197	Intermediate Similarity	NPC242032
0.8197	Intermediate Similarity	NPC324112
0.8197	Intermediate Similarity	NPC473092
0.8197	Intermediate Similarity	NPC246620
0.8197	Intermediate Similarity	NPC236760
0.8197	Intermediate Similarity	NPC124452
0.8197	Intermediate Similarity	NPC159968
0.8197	Intermediate Similarity	NPC202904
0.8197	Intermediate Similarity	NPC236791
0.819	Intermediate Similarity	NPC304208
0.819	Intermediate Similarity	NPC52464
0.8182	Intermediate Similarity	NPC234400
0.8182	Intermediate Similarity	NPC60885
0.8182	Intermediate Similarity	NPC249836
0.8174	Intermediate Similarity	NPC283169
0.8167	Intermediate Similarity	NPC474160
0.8167	Intermediate Similarity	NPC95168
0.8165	Intermediate Similarity	NPC474603
0.8165	Intermediate Similarity	NPC30506
0.8165	Intermediate Similarity	NPC102216
0.8165	Intermediate Similarity	NPC12987
0.8165	Intermediate Similarity	NPC241891
0.816	Intermediate Similarity	NPC218884
0.8158	Intermediate Similarity	NPC165106
0.8145	Intermediate Similarity	NPC192687
0.8145	Intermediate Similarity	NPC126836
0.8145	Intermediate Similarity	NPC254000
0.8145	Intermediate Similarity	NPC224157
0.8137	Intermediate Similarity	NPC47422
0.8136	Intermediate Similarity	NPC93398
0.8136	Intermediate Similarity	NPC8283
0.8136	Intermediate Similarity	NPC258979
0.8136	Intermediate Similarity	NPC10932
0.8136	Intermediate Similarity	NPC61516
0.8136	Intermediate Similarity	NPC232084
0.8136	Intermediate Similarity	NPC474565
0.8136	Intermediate Similarity	NPC247364
0.813	Intermediate Similarity	NPC470213
0.813	Intermediate Similarity	NPC266691
0.813	Intermediate Similarity	NPC98631
0.813	Intermediate Similarity	NPC63179
0.813	Intermediate Similarity	NPC31707
0.813	Intermediate Similarity	NPC54321
0.813	Intermediate Similarity	NPC281864

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 NPC303521 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	478
0.1-0.2	1017
0.2-0.3	1450
0.3-0.4	2760
0.4-0.5	1764
0.5-0.6	1050
0.6-0.7	522
0.7-0.8	100
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8305	Intermediate Similarity	NPD1610	Phase 2
0.8211	Intermediate Similarity	NPD4625	Phase 3
0.8158	Intermediate Similarity	NPD5283	Phase 1
0.812	Intermediate Similarity	NPD1548	Phase 1
0.8083	Intermediate Similarity	NPD2981	Phase 2
0.8065	Intermediate Similarity	NPD3027	Phase 3
0.8017	Intermediate Similarity	NPD2982	Phase 2
0.8017	Intermediate Similarity	NPD2983	Phase 2
0.8017	Intermediate Similarity	NPD4749	Approved
0.7984	Intermediate Similarity	NPD4908	Phase 1
0.7983	Intermediate Similarity	NPD17	Approved
0.7967	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD3018	Phase 2
0.7899	Intermediate Similarity	NPD1651	Approved
0.789	Intermediate Similarity	NPD1242	Phase 1
0.7863	Intermediate Similarity	NPD709	Approved
0.7857	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD5451	Approved
0.7787	Intermediate Similarity	NPD1608	Approved
0.776	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD1613	Approved
0.7717	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD1281	Approved
0.7652	Intermediate Similarity	NPD4750	Phase 3
0.7581	Intermediate Similarity	NPD1669	Approved
0.7561	Intermediate Similarity	NPD422	Phase 1
0.7561	Intermediate Similarity	NPD1611	Approved
0.7544	Intermediate Similarity	NPD968	Approved
0.7521	Intermediate Similarity	NPD228	Approved
0.752	Intermediate Similarity	NPD1283	Approved
0.75	Intermediate Similarity	NPD940	Approved
0.75	Intermediate Similarity	NPD846	Approved
0.748	Intermediate Similarity	NPD2861	Phase 2
0.7462	Intermediate Similarity	NPD1240	Approved
0.7459	Intermediate Similarity	NPD5585	Approved
0.7458	Intermediate Similarity	NPD5535	Approved
0.7442	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6671	Approved
0.7414	Intermediate Similarity	NPD2684	Approved
0.7372	Intermediate Similarity	NPD7124	Phase 2
0.736	Intermediate Similarity	NPD2233	Approved
0.736	Intermediate Similarity	NPD2230	Approved
0.736	Intermediate Similarity	NPD2232	Approved
0.7353	Intermediate Similarity	NPD3892	Phase 2
0.7348	Intermediate Similarity	NPD1607	Approved
0.7328	Intermediate Similarity	NPD2238	Phase 2
0.7328	Intermediate Similarity	NPD290	Approved
0.7321	Intermediate Similarity	NPD3020	Approved
0.7317	Intermediate Similarity	NPD3445	Approved
0.7317	Intermediate Similarity	NPD3444	Approved
0.7317	Intermediate Similarity	NPD3443	Approved
0.7317	Intermediate Similarity	NPD5691	Approved
0.7313	Intermediate Similarity	NPD3539	Phase 1
0.7313	Intermediate Similarity	NPD6100	Approved
0.7313	Intermediate Similarity	NPD6099	Approved
0.7313	Intermediate Similarity	NPD2796	Approved
0.7302	Intermediate Similarity	NPD5327	Phase 3
0.7295	Intermediate Similarity	NPD5536	Phase 2
0.7293	Intermediate Similarity	NPD6111	Discontinued
0.728	Intermediate Similarity	NPD3705	Approved
0.7273	Intermediate Similarity	NPD7157	Approved
0.7273	Intermediate Similarity	NPD6387	Discontinued
0.7273	Intermediate Similarity	NPD2557	Approved
0.7266	Intermediate Similarity	NPD7905	Discontinued
0.7259	Intermediate Similarity	NPD3540	Phase 1
0.7258	Intermediate Similarity	NPD2667	Approved
0.7258	Intermediate Similarity	NPD2668	Approved
0.7258	Intermediate Similarity	NPD4626	Approved
0.7239	Intermediate Similarity	NPD1510	Phase 2
0.7239	Intermediate Similarity	NPD3748	Approved
0.7236	Intermediate Similarity	NPD1182	Approved
0.7227	Intermediate Similarity	NPD1137	Approved
0.7227	Intermediate Similarity	NPD1139	Approved
0.7226	Intermediate Similarity	NPD7466	Approved
0.7222	Intermediate Similarity	NPD1840	Phase 2
0.7213	Intermediate Similarity	NPD3596	Phase 2
0.7207	Intermediate Similarity	NPD2859	Approved
0.7207	Intermediate Similarity	NPD2860	Approved
0.7167	Intermediate Similarity	NPD1138	Approved
0.7167	Intermediate Similarity	NPD7843	Approved
0.7165	Intermediate Similarity	NPD4359	Approved
0.7164	Intermediate Similarity	NPD2200	Suspended
0.7154	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD288	Approved
0.7132	Intermediate Similarity	NPD6584	Phase 3
0.7132	Intermediate Similarity	NPD4624	Approved
0.712	Intermediate Similarity	NPD1778	Approved
0.712	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2933	Approved
0.7117	Intermediate Similarity	NPD2934	Approved
0.7109	Intermediate Similarity	NPD1876	Approved
0.7107	Intermediate Similarity	NPD1241	Discontinued
0.7105	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6581	Approved
0.7097	Intermediate Similarity	NPD6580	Approved
0.7094	Intermediate Similarity	NPD3134	Approved
0.7092	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3972	Approved
0.7087	Intermediate Similarity	NPD1244	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2979	Phase 3
0.7063	Intermediate Similarity	NPD3847	Discontinued
0.7059	Intermediate Similarity	NPD3021	Approved
0.7059	Intermediate Similarity	NPD3022	Approved
0.7054	Intermediate Similarity	NPD3266	Approved
0.7054	Intermediate Similarity	NPD2797	Approved
0.7054	Intermediate Similarity	NPD844	Approved
0.7054	Intermediate Similarity	NPD3267	Approved
0.7045	Intermediate Similarity	NPD1296	Phase 2
0.7045	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5109	Approved
0.7045	Intermediate Similarity	NPD5111	Phase 2
0.7045	Intermediate Similarity	NPD5110	Phase 2
0.7042	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD3049	Approved
0.7034	Intermediate Similarity	NPD1358	Approved
0.7029	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD821	Approved
0.7009	Intermediate Similarity	NPD9697	Approved
0.7008	Intermediate Similarity	NPD1091	Approved
0.7007	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4108	Discontinued
0.6984	Remote Similarity	NPD5846	Approved
0.6984	Remote Similarity	NPD6516	Phase 2
0.6984	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD6696	Suspended
0.6977	Remote Similarity	NPD8651	Approved
0.6977	Remote Similarity	NPD2922	Phase 1
0.697	Remote Similarity	NPD7095	Approved
0.6967	Remote Similarity	NPD498	Approved
0.6967	Remote Similarity	NPD496	Approved
0.6967	Remote Similarity	NPD495	Approved
0.6964	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4097	Suspended
0.6957	Remote Similarity	NPD1549	Phase 2
0.6953	Remote Similarity	NPD2235	Phase 2
0.6953	Remote Similarity	NPD2231	Phase 2
0.6944	Remote Similarity	NPD4005	Discontinued
0.6944	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4060	Phase 1
0.694	Remote Similarity	NPD1558	Phase 1
0.6934	Remote Similarity	NPD1551	Phase 2
0.6934	Remote Similarity	NPD2438	Suspended
0.6929	Remote Similarity	NPD3496	Discontinued
0.6923	Remote Similarity	NPD4098	Discontinued
0.6911	Remote Similarity	NPD497	Approved
0.6906	Remote Similarity	NPD1243	Approved
0.6901	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7447	Phase 1
0.6899	Remote Similarity	NPD6583	Phase 3
0.6899	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6582	Phase 2
0.6894	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2342	Discontinued
0.6889	Remote Similarity	NPD5735	Approved
0.6885	Remote Similarity	NPD7635	Approved
0.6875	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7819	Suspended
0.687	Remote Similarity	NPD2798	Approved
0.6866	Remote Similarity	NPD4870	Approved
0.6866	Remote Similarity	NPD4474	Approved
0.6866	Remote Similarity	NPD4475	Approved
0.685	Remote Similarity	NPD2556	Approved
0.685	Remote Similarity	NPD2554	Approved
0.6846	Remote Similarity	NPD3225	Approved
0.6846	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4055	Discovery
0.6842	Remote Similarity	NPD1024	Discontinued
0.6838	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7212	Phase 2
0.6831	Remote Similarity	NPD7213	Phase 3
0.6831	Remote Similarity	NPD4357	Discontinued
0.6831	Remote Similarity	NPD1511	Approved
0.6828	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2486	Discontinued
0.6825	Remote Similarity	NPD1894	Discontinued
0.6818	Remote Similarity	NPD1712	Approved
0.6818	Remote Similarity	NPD9295	Approved
0.6815	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4140	Approved
0.6812	Remote Similarity	NPD2531	Phase 2
0.6812	Remote Similarity	NPD2935	Discontinued
0.681	Remote Similarity	NPD3028	Approved
0.6803	Remote Similarity	NPD37	Approved
0.6803	Remote Similarity	NPD1934	Approved
0.6791	Remote Similarity	NPD5718	Phase 2
0.6791	Remote Similarity	NPD3268	Approved
0.6791	Remote Similarity	NPD1039	Discontinued
0.6788	Remote Similarity	NPD6895	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