NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	140.05
Volume:	139.533
LogP:	0.673
LogD:	1.134
LogS:	0.031
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.574
Synthetic Accessibility Score:	1.706
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.532
MDCK Permeability:	1.4111380551184993e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.294
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.186
30% Bioavailability (F30%):	0.225

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	60.982845306396484%
Volume Distribution (VD):	0.948
Pgp-substrate:	27.47712516784668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.448
CYP1A2-substrate:	0.9
CYP2C19-inhibitor:	0.138
CYP2C19-substrate:	0.209
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.218
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	15.423
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.07
AMES Toxicity:	0.138
Rat Oral Acute Toxicity:	0.545
Maximum Recommended Daily Dose:	0.124
Skin Sensitization:	0.894
Carcinogencity:	0.481
Eye Corrosion:	0.957
Eye Irritation:	0.985
Respiratory Toxicity:	0.252

Download Data

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

Natural Product: NPC124712

Natural Product ID:	NPC124712
*Common Name:**	2-Methoxyhydroquinone
IUPAC Name:	2-methoxybenzene-1,4-diol
Synonyms:
Standard InCHIKey:	LAQYHRQFABOIFD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H8O3/c1-10-7-4-5(8)2-3-6(7)9/h2-4,8-9H,1H3
SMILES:	COc1cc(O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551075
PubChem CID:	69988
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO29385	Nidus vespae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO29385	Nidus vespae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	6
IC50	1

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	8900.0	nM	PMID[555505]
NPT1083	Cell Line	A-375	Homo sapiens	EC50	>	100000.0	nM	PMID[555506]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	EC50	>	100000.0	nM	PMID[555506]
NPT81	Cell Line	A549	Homo sapiens	EC50	>	100000.0	nM	PMID[555506]
NPT27	Others	Unspecified		EC50	>	100000.0	nM	PMID[555506]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	100000.0	nM	PMID[555506]

☑ 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 NPC124712 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	547
0.1-0.2	4301
0.2-0.3	13348
0.3-0.4	6174
0.4-0.5	5176
0.5-0.6	8405
0.6-0.7	3893
0.7-0.8	790
0.8-0.85	52
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC307875
0.9505	High Similarity	NPC232654
0.8962	High Similarity	NPC247871
0.8889	High Similarity	NPC16649
0.8889	High Similarity	NPC114325
0.8586	High Similarity	NPC288923
0.8571	High Similarity	NPC151617
0.8571	High Similarity	NPC259638
0.8571	High Similarity	NPC76915
0.8482	Intermediate Similarity	NPC193067
0.8462	Intermediate Similarity	NPC221090
0.8462	Intermediate Similarity	NPC183446
0.8421	Intermediate Similarity	NPC20674
0.8421	Intermediate Similarity	NPC214289
0.8384	Intermediate Similarity	NPC157213
0.8376	Intermediate Similarity	NPC192810
0.8365	Intermediate Similarity	NPC314803
0.8362	Intermediate Similarity	NPC285289
0.8348	Intermediate Similarity	NPC229401
0.8319	Intermediate Similarity	NPC112596
0.83	Intermediate Similarity	NPC302546
0.8291	Intermediate Similarity	NPC135414
0.8291	Intermediate Similarity	NPC474864
0.8291	Intermediate Similarity	NPC152722
0.8291	Intermediate Similarity	NPC246967
0.8283	Intermediate Similarity	NPC280254
0.8276	Intermediate Similarity	NPC205850
0.825	Intermediate Similarity	NPC37074
0.82	Intermediate Similarity	NPC47422
0.819	Intermediate Similarity	NPC247364
0.819	Intermediate Similarity	NPC61516
0.819	Intermediate Similarity	NPC10932
0.819	Intermediate Similarity	NPC232084
0.8182	Intermediate Similarity	NPC266691
0.8182	Intermediate Similarity	NPC19694
0.8167	Intermediate Similarity	NPC245060
0.8167	Intermediate Similarity	NPC298845
0.8167	Intermediate Similarity	NPC189589
0.8167	Intermediate Similarity	NPC469622
0.8136	Intermediate Similarity	NPC473411
0.8136	Intermediate Similarity	NPC126216
0.8136	Intermediate Similarity	NPC228875
0.8136	Intermediate Similarity	NPC262253
0.8136	Intermediate Similarity	NPC105147
0.8136	Intermediate Similarity	NPC71579
0.812	Intermediate Similarity	NPC276195
0.8115	Intermediate Similarity	NPC58164
0.8115	Intermediate Similarity	NPC10225
0.8103	Intermediate Similarity	NPC226629
0.81	Intermediate Similarity	NPC206876
0.8099	Intermediate Similarity	NPC216836
0.8073	Intermediate Similarity	NPC473653
0.8067	Intermediate Similarity	NPC95168
0.8067	Intermediate Similarity	NPC165375
0.8067	Intermediate Similarity	NPC220598
0.8067	Intermediate Similarity	NPC238810
0.8051	Intermediate Similarity	NPC49341
0.8049	Intermediate Similarity	NPC220935
0.8049	Intermediate Similarity	NPC51840
0.8049	Intermediate Similarity	NPC311680
0.8049	Intermediate Similarity	NPC299221
0.8049	Intermediate Similarity	NPC234488
0.8	Intermediate Similarity	NPC25817
0.8	Intermediate Similarity	NPC5796
0.8	Intermediate Similarity	NPC206487
0.7984	Intermediate Similarity	NPC287780
0.7984	Intermediate Similarity	NPC82503
0.7984	Intermediate Similarity	NPC45715
0.7984	Intermediate Similarity	NPC12275
0.7984	Intermediate Similarity	NPC474356
0.7983	Intermediate Similarity	NPC270326
0.7983	Intermediate Similarity	NPC41562
0.7967	Intermediate Similarity	NPC45824
0.7967	Intermediate Similarity	NPC158477
0.7966	Intermediate Similarity	NPC166759
0.7951	Intermediate Similarity	NPC469621
0.7934	Intermediate Similarity	NPC271985
0.7934	Intermediate Similarity	NPC60885
0.7934	Intermediate Similarity	NPC193544
0.7934	Intermediate Similarity	NPC221077
0.7934	Intermediate Similarity	NPC233410
0.7934	Intermediate Similarity	NPC203133
0.7934	Intermediate Similarity	NPC265483
0.7934	Intermediate Similarity	NPC234400
0.7934	Intermediate Similarity	NPC116907
0.7934	Intermediate Similarity	NPC57490
0.7934	Intermediate Similarity	NPC82483
0.7934	Intermediate Similarity	NPC475169
0.7934	Intermediate Similarity	NPC17943
0.7934	Intermediate Similarity	NPC299584
0.7934	Intermediate Similarity	NPC300326
0.7934	Intermediate Similarity	NPC117214
0.7934	Intermediate Similarity	NPC298757
0.7934	Intermediate Similarity	NPC208950
0.7934	Intermediate Similarity	NPC472093
0.7934	Intermediate Similarity	NPC58279
0.7934	Intermediate Similarity	NPC251855
0.7931	Intermediate Similarity	NPC304208
0.7931	Intermediate Similarity	NPC9248
0.7931	Intermediate Similarity	NPC52464
0.792	Intermediate Similarity	NPC161203
0.792	Intermediate Similarity	NPC6451
0.7917	Intermediate Similarity	NPC217854
0.7917	Intermediate Similarity	NPC228922
0.7917	Intermediate Similarity	NPC121115
0.7917	Intermediate Similarity	NPC197757
0.7909	Intermediate Similarity	NPC164576
0.7903	Intermediate Similarity	NPC60756
0.7903	Intermediate Similarity	NPC214860
0.7903	Intermediate Similarity	NPC208769
0.7899	Intermediate Similarity	NPC75713
0.7899	Intermediate Similarity	NPC145780
0.7886	Intermediate Similarity	NPC63179
0.7881	Intermediate Similarity	NPC35071
0.7881	Intermediate Similarity	NPC474565
0.7881	Intermediate Similarity	NPC148615
0.7881	Intermediate Similarity	NPC177475
0.7876	Intermediate Similarity	NPC203924
0.7869	Intermediate Similarity	NPC28730
0.7869	Intermediate Similarity	NPC103823
0.7869	Intermediate Similarity	NPC223136
0.7869	Intermediate Similarity	NPC110677
0.7869	Intermediate Similarity	NPC476006
0.7869	Intermediate Similarity	NPC18924
0.7869	Intermediate Similarity	NPC214406
0.7869	Intermediate Similarity	NPC44748
0.7869	Intermediate Similarity	NPC78974
0.7863	Intermediate Similarity	NPC474612
0.7857	Intermediate Similarity	NPC60982
0.7857	Intermediate Similarity	NPC246358
0.7857	Intermediate Similarity	NPC37196
0.7857	Intermediate Similarity	NPC233731
0.7857	Intermediate Similarity	NPC165386
0.7857	Intermediate Similarity	NPC7097
0.7857	Intermediate Similarity	NPC36108
0.7857	Intermediate Similarity	NPC94236
0.7845	Intermediate Similarity	NPC221049
0.784	Intermediate Similarity	NPC232275
0.7823	Intermediate Similarity	NPC190144
0.7823	Intermediate Similarity	NPC170844
0.7823	Intermediate Similarity	NPC476968
0.7805	Intermediate Similarity	NPC124452
0.7805	Intermediate Similarity	NPC236791
0.7805	Intermediate Similarity	NPC210355
0.7805	Intermediate Similarity	NPC293054
0.7805	Intermediate Similarity	NPC82679
0.7805	Intermediate Similarity	NPC74817
0.7805	Intermediate Similarity	NPC236760
0.7805	Intermediate Similarity	NPC169474
0.7805	Intermediate Similarity	NPC50368
0.7805	Intermediate Similarity	NPC266555
0.7805	Intermediate Similarity	NPC127587
0.7805	Intermediate Similarity	NPC324112
0.7805	Intermediate Similarity	NPC159968
0.7805	Intermediate Similarity	NPC246620
0.7805	Intermediate Similarity	NPC282000
0.78	Intermediate Similarity	NPC23837
0.7797	Intermediate Similarity	NPC320987
0.7797	Intermediate Similarity	NPC308217
0.7797	Intermediate Similarity	NPC181969
0.7795	Intermediate Similarity	NPC106215
0.7795	Intermediate Similarity	NPC103967
0.7795	Intermediate Similarity	NPC310854
0.7788	Intermediate Similarity	NPC94045
0.7769	Intermediate Similarity	NPC84086
0.7769	Intermediate Similarity	NPC282496
0.7769	Intermediate Similarity	NPC233526
0.7769	Intermediate Similarity	NPC136319
0.776	Intermediate Similarity	NPC229231
0.776	Intermediate Similarity	NPC192687
0.776	Intermediate Similarity	NPC224157
0.775	Intermediate Similarity	NPC470804
0.7742	Intermediate Similarity	NPC206615
0.7742	Intermediate Similarity	NPC470213
0.7742	Intermediate Similarity	NPC154866
0.7742	Intermediate Similarity	NPC247146
0.7742	Intermediate Similarity	NPC98631
0.7742	Intermediate Similarity	NPC109275
0.7742	Intermediate Similarity	NPC186843
0.7739	Intermediate Similarity	NPC204120
0.7734	Intermediate Similarity	NPC255147
0.7734	Intermediate Similarity	NPC134968
0.7734	Intermediate Similarity	NPC283009
0.7734	Intermediate Similarity	NPC261873
0.7734	Intermediate Similarity	NPC201357
0.7734	Intermediate Similarity	NPC281521
0.7734	Intermediate Similarity	NPC472337
0.7724	Intermediate Similarity	NPC76451
0.7724	Intermediate Similarity	NPC171533
0.7719	Intermediate Similarity	NPC78918
0.7719	Intermediate Similarity	NPC257124
0.7719	Intermediate Similarity	NPC195873
0.7719	Intermediate Similarity	NPC156840
0.7719	Intermediate Similarity	NPC8547
0.7719	Intermediate Similarity	NPC139617
0.7719	Intermediate Similarity	NPC173746
0.7717	Intermediate Similarity	NPC474810
0.7712	Intermediate Similarity	NPC63083
0.7712	Intermediate Similarity	NPC255675
0.7705	Intermediate Similarity	NPC122792

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 NPC124712 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	463
0.1-0.2	1302
0.2-0.3	3010
0.3-0.4	2396
0.4-0.5	1153
0.5-0.6	706
0.6-0.7	100
0.7-0.8	17
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD9296	Approved
0.8384	Intermediate Similarity	NPD9295	Approved
0.8283	Intermediate Similarity	NPD9094	Approved
0.8037	Intermediate Similarity	NPD291	Approved
0.7823	Intermediate Similarity	NPD3027	Phase 3
0.7719	Intermediate Similarity	NPD228	Approved
0.7677	Intermediate Similarity	NPD9089	Approved
0.7576	Intermediate Similarity	NPD9093	Approved
0.7524	Intermediate Similarity	NPD9365	Approved
0.7521	Intermediate Similarity	NPD9299	Approved
0.7479	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7534	Approved
0.7417	Intermediate Similarity	NPD7533	Approved
0.7391	Intermediate Similarity	NPD556	Approved
0.7381	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1613	Approved
0.7273	Intermediate Similarity	NPD9088	Approved
0.72	Intermediate Similarity	NPD2983	Phase 2
0.72	Intermediate Similarity	NPD2982	Phase 2
0.7131	Intermediate Similarity	NPD1548	Phase 1
0.713	Intermediate Similarity	NPD968	Approved
0.712	Intermediate Similarity	NPD2981	Phase 2
0.7069	Intermediate Similarity	NPD290	Approved
0.6977	Remote Similarity	NPD3018	Phase 2
0.6929	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9552	Approved
0.6905	Remote Similarity	NPD422	Phase 1
0.6905	Remote Similarity	NPD1091	Approved
0.6905	Remote Similarity	NPD1610	Phase 2
0.6901	Remote Similarity	NPD1653	Approved
0.6869	Remote Similarity	NPD9087	Approved
0.681	Remote Similarity	NPD9501	Approved
0.68	Remote Similarity	NPD1357	Approved
0.6794	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD940	Approved
0.6783	Remote Similarity	NPD846	Approved
0.6781	Remote Similarity	NPD2801	Approved
0.6723	Remote Similarity	NPD2684	Approved
0.6718	Remote Similarity	NPD9494	Approved
0.6716	Remote Similarity	NPD1558	Phase 1
0.6696	Remote Similarity	NPD1242	Phase 1
0.6693	Remote Similarity	NPD915	Approved
0.6667	Remote Similarity	NPD1798	Approved
0.6667	Remote Similarity	NPD4749	Approved
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD1797	Approved
0.6667	Remote Similarity	NPD230	Phase 1
0.6613	Remote Similarity	NPD6671	Approved
0.6599	Remote Similarity	NPD1934	Approved
0.6596	Remote Similarity	NPD2219	Phase 1
0.6594	Remote Similarity	NPD3454	Phase 3
0.6585	Remote Similarity	NPD5283	Phase 1
0.6567	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3145	Approved
0.6567	Remote Similarity	NPD3144	Approved
0.6519	Remote Similarity	NPD2674	Phase 3
0.6515	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3705	Approved
0.6504	Remote Similarity	NPD7843	Approved
0.6503	Remote Similarity	NPD4357	Discontinued
0.6503	Remote Similarity	NPD1511	Approved
0.6493	Remote Similarity	NPD4625	Phase 3
0.6481	Remote Similarity	NPD111	Approved
0.6471	Remote Similarity	NPD1240	Approved
0.6444	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3540	Phase 1
0.6414	Remote Similarity	NPD1512	Approved
0.6378	Remote Similarity	NPD1102	Approved
0.6378	Remote Similarity	NPD5536	Phase 2
0.6378	Remote Similarity	NPD1103	Approved
0.6377	Remote Similarity	NPD1607	Approved
0.6364	Remote Similarity	NPD1358	Approved
0.6358	Remote Similarity	NPD3882	Suspended
0.6357	Remote Similarity	NPD3539	Phase 1
0.6351	Remote Similarity	NPD4678	Approved
0.6351	Remote Similarity	NPD4675	Approved
0.635	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.635	Remote Similarity	NPD3620	Phase 2
0.6349	Remote Similarity	NPD7157	Approved
0.6349	Remote Similarity	NPD191	Approved
0.6343	Remote Similarity	NPD2861	Phase 2
0.6341	Remote Similarity	NPD2671	Approved
0.6341	Remote Similarity	NPD2673	Approved
0.6341	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD1652	Phase 2
0.6333	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD6111	Discontinued
0.6324	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD447	Suspended
0.6275	Remote Similarity	NPD6234	Discontinued
0.6271	Remote Similarity	NPD289	Clinical (unspecified phase)
0.626	Remote Similarity	NPD3022	Approved
0.626	Remote Similarity	NPD4750	Phase 3
0.626	Remote Similarity	NPD3021	Approved
0.625	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD6696	Suspended
0.624	Remote Similarity	NPD821	Approved
0.6222	Remote Similarity	NPD2250	Discontinued
0.6212	Remote Similarity	NPD9269	Phase 2
0.619	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD3496	Discontinued
0.6182	Remote Similarity	NPD9073	Approved
0.6178	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD6166	Phase 2
0.6176	Remote Similarity	NPD600	Approved
0.6176	Remote Similarity	NPD596	Approved
0.617	Remote Similarity	NPD1510	Phase 2
0.6159	Remote Similarity	NPD6233	Phase 2
0.6159	Remote Similarity	NPD37	Approved
0.6148	Remote Similarity	NPD3134	Approved
0.6144	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD1535	Discovery
0.6127	Remote Similarity	NPD1551	Phase 2
0.6121	Remote Similarity	NPD2934	Approved
0.6121	Remote Similarity	NPD2933	Approved
0.6111	Remote Similarity	NPD5177	Phase 3
0.6111	Remote Similarity	NPD3060	Approved
0.6111	Remote Similarity	NPD769	Approved
0.6107	Remote Similarity	NPD1778	Approved
0.6107	Remote Similarity	NPD9384	Approved
0.6107	Remote Similarity	NPD9381	Approved
0.6103	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD9095	Approved
0.6102	Remote Similarity	NPD68	Approved
0.6102	Remote Similarity	NPD9097	Approved
0.6102	Remote Similarity	NPD9096	Approved
0.6096	Remote Similarity	NPD7124	Phase 2
0.609	Remote Similarity	NPD1481	Phase 2
0.6084	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD1375	Discontinued
0.6084	Remote Similarity	NPD7266	Discontinued
0.6078	Remote Similarity	NPD3817	Phase 2
0.6077	Remote Similarity	NPD9545	Approved
0.6069	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD2859	Approved
0.6068	Remote Similarity	NPD2860	Approved
0.6067	Remote Similarity	NPD4005	Discontinued
0.6062	Remote Similarity	NPD7054	Approved
0.6061	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD5297	Approved
0.6051	Remote Similarity	NPD6232	Discontinued
0.6047	Remote Similarity	NPD9493	Approved
0.6045	Remote Similarity	NPD9622	Approved
0.6043	Remote Similarity	NPD839	Approved
0.6043	Remote Similarity	NPD840	Approved
0.6042	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD1549	Phase 2
0.6039	Remote Similarity	NPD4967	Phase 2
0.6039	Remote Similarity	NPD4966	Approved
0.6039	Remote Similarity	NPD4965	Approved
0.6029	Remote Similarity	NPD5647	Approved
0.6029	Remote Similarity	NPD1469	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD2224	Approved
0.6028	Remote Similarity	NPD2223	Approved
0.6027	Remote Similarity	NPD6190	Approved
0.6026	Remote Similarity	NPD4380	Phase 2
0.6025	Remote Similarity	NPD7472	Approved
0.6025	Remote Similarity	NPD7074	Phase 3
0.6014	Remote Similarity	NPD3180	Approved
0.6014	Remote Similarity	NPD4123	Phase 3
0.6014	Remote Similarity	NPD6099	Approved
0.6014	Remote Similarity	NPD6100	Approved
0.6014	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD1424	Approved
0.6014	Remote Similarity	NPD3179	Approved
0.6013	Remote Similarity	NPD1465	Phase 2
0.6012	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2238	Phase 2
0.6	Remote Similarity	NPD2922	Phase 1
0.6	Remote Similarity	NPD3818	Discontinued
0.6	Remote Similarity	NPD3225	Approved
0.6	Remote Similarity	NPD7228	Approved
0.6	Remote Similarity	NPD4236	Phase 3
0.6	Remote Similarity	NPD9092	Discovery
0.6	Remote Similarity	NPD4237	Approved
0.6	Remote Similarity	NPD8651	Approved
0.6	Remote Similarity	NPD5451	Approved
0.6	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD4538	Approved
0.5986	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD4536	Approved
0.5985	Remote Similarity	NPD6516	Phase 2
0.5985	Remote Similarity	NPD5846	Approved
0.5984	Remote Similarity	NPD9379	Approved
0.5984	Remote Similarity	NPD9377	Approved
0.5983	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD1048	Approved
0.597	Remote Similarity	NPD2233	Approved
0.597	Remote Similarity	NPD1608	Approved
0.597	Remote Similarity	NPD2230	Approved
0.597	Remote Similarity	NPD9717	Approved
0.597	Remote Similarity	NPD2232	Approved
0.5968	Remote Similarity	NPD9624	Approved
0.5968	Remote Similarity	NPD5373	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