NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	168.04
Volume:	162.983
LogP:	2.278
LogD:	2.924
LogS:	-2.194
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	1.588
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.102
MDCK Permeability:	7.19729268894298e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.85

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.353
Plasma Protein Binding (PPB):	74.41810607910156%
Volume Distribution (VD):	0.333
Pgp-substrate:	21.402240753173828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.103
CYP1A2-substrate:	0.682
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.144
CYP2C9-substrate:	0.253
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.069

ADMET: Excretion

Clearance (CL):	7.511
Half-life (T1/2):	0.894

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.374
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.248
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.131
Carcinogencity:	0.056
Eye Corrosion:	0.023
Eye Irritation:	0.964
Respiratory Toxicity:	0.509

Download Data

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

Natural Product: NPC307732

Natural Product ID:	NPC307732
*Common Name:**	4-Methoxysalicylic Acid
IUPAC Name:	2-hydroxy-4-methoxybenzoic acid
Synonyms:	4-Methoxysalicylic Acid
Standard InCHIKey:	MRIXVKKOHPQOFK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8O4/c1-12-5-2-3-6(8(10)11)7(9)4-5/h2-4,9H,1H3,(H,10,11)
SMILES:	COc1ccc(c(c1)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507095
PubChem CID:	75231
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002344] Methoxybenzoic acids and derivatives [CHEMONTID:0002346] P-methoxybenzoic acids 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
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20000780]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31397570]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8251	Cortex lycii radicis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16308	Citrus wilsonii	Species	Rutaceae	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
LD50	4
Others	14
Potency	1

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	1
ORGANISM	1
Others	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	32642.7	nM	PMID[480088]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	99.4	%	PMID[480090]
NPT113	Cell Line	RAW264.7	Mus musculus	CC50	>	40000.0	nM	PMID[480090]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	79.6	%	PMID[480090]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	7.34	%	PMID[480087]
NPT21912	ORGANISM	Hylobius abietis	Hylobius abietis	AFI	=	24.0	%	PMID[480089]
NPT35	Others	n.a.		LogP	=	1.21	n.a.	PMID[480091]
NPT2	Others	Unspecified		FC	=	2.0	n.a.	PMID[480091]
NPT2	Others	Unspecified		MHC	=	10.0	ug	PMID[480091]
NPT2	Others	Unspecified		LD50	=	10.0	ug	PMID[480091]
NPT2	Others	Unspecified		FC	=	3.75	n.a.	PMID[480091]
NPT2	Others	Unspecified		LD50	=	150.0	ug	PMID[480091]
NPT2	Others	Unspecified		FC	=	4.0	n.a.	PMID[480091]
NPT2	Others	Unspecified		MHC	=	20.0	ug	PMID[480091]
NPT2	Others	Unspecified		FC	=	3.2	n.a.	PMID[480091]
NPT2	Others	Unspecified		LD50	=	9.0	ug	PMID[480091]
NPT2	Others	Unspecified		FC	=	9.8	n.a.	PMID[480091]
NPT2	Others	Unspecified		LD50	=	22.0	ug	PMID[480091]

☑ 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 NPC307732 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	355
0.1-0.2	1864
0.2-0.3	5321
0.3-0.4	10614
0.4-0.5	6525
0.5-0.6	4233
0.6-0.7	6582
0.7-0.8	5415
0.8-0.85	1313
0.85-0.9	409
0.9-0.95	60
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC42292
0.9837	High Similarity	NPC293453
0.9675	High Similarity	NPC95309
0.952	High Similarity	NPC80694
0.952	High Similarity	NPC186098
0.9512	High Similarity	NPC6888
0.9444	High Similarity	NPC8005
0.9444	High Similarity	NPC78662
0.944	High Similarity	NPC128428
0.944	High Similarity	NPC305518
0.9308	High Similarity	NPC182496
0.9308	High Similarity	NPC180905
0.9302	High Similarity	NPC212631
0.9302	High Similarity	NPC257756
0.9302	High Similarity	NPC205468
0.9302	High Similarity	NPC87231
0.9302	High Similarity	NPC129132
0.9291	High Similarity	NPC212379
0.9291	High Similarity	NPC69235
0.9231	High Similarity	NPC242294
0.9231	High Similarity	NPC56031
0.9231	High Similarity	NPC175098
0.9231	High Similarity	NPC192304
0.9231	High Similarity	NPC139813
0.9231	High Similarity	NPC337373
0.9231	High Similarity	NPC263670
0.9231	High Similarity	NPC188646
0.9231	High Similarity	NPC312318
0.9231	High Similarity	NPC472365
0.9225	High Similarity	NPC313618
0.9225	High Similarity	NPC262359
0.9225	High Similarity	NPC64359
0.9225	High Similarity	NPC308037
0.9219	High Similarity	NPC185497
0.9219	High Similarity	NPC12694
0.9167	High Similarity	NPC135837
0.916	High Similarity	NPC286336
0.916	High Similarity	NPC164136
0.9141	High Similarity	NPC230818
0.9141	High Similarity	NPC60558
0.9127	High Similarity	NPC65041
0.9084	High Similarity	NPC18877
0.9084	High Similarity	NPC204960
0.9084	High Similarity	NPC20560
0.9084	High Similarity	NPC159623
0.9084	High Similarity	NPC144051
0.9084	High Similarity	NPC294593
0.9084	High Similarity	NPC28753
0.9084	High Similarity	NPC82225
0.9077	High Similarity	NPC31872
0.9077	High Similarity	NPC473584
0.9077	High Similarity	NPC475589
0.907	High Similarity	NPC247779
0.907	High Similarity	NPC84772
0.9048	High Similarity	NPC255073
0.9037	High Similarity	NPC475730
0.9024	High Similarity	NPC61779
0.9023	High Similarity	NPC476333
0.9023	High Similarity	NPC66349
0.9023	High Similarity	NPC472364
0.9023	High Similarity	NPC473391
0.9023	High Similarity	NPC168105
0.9023	High Similarity	NPC1486
0.9023	High Similarity	NPC249606
0.9023	High Similarity	NPC472367
0.9023	High Similarity	NPC12165
0.9023	High Similarity	NPC274109
0.9023	High Similarity	NPC150399
0.9023	High Similarity	NPC98115
0.9023	High Similarity	NPC41461
0.9023	High Similarity	NPC477242
0.9023	High Similarity	NPC25287
0.9023	High Similarity	NPC477243
0.9023	High Similarity	NPC186838
0.9023	High Similarity	NPC477244
0.9023	High Similarity	NPC222633
0.9008	High Similarity	NPC203817
0.9008	High Similarity	NPC25937
0.9	High Similarity	NPC219892
0.9	High Similarity	NPC189823
0.9	High Similarity	NPC5515
0.9	High Similarity	NPC270369
0.9	High Similarity	NPC324482
0.8971	High Similarity	NPC250755
0.8971	High Similarity	NPC474385
0.8963	High Similarity	NPC230902
0.8963	High Similarity	NPC165172
0.8955	High Similarity	NPC162680
0.8955	High Similarity	NPC7013
0.8955	High Similarity	NPC250266
0.8955	High Similarity	NPC181124
0.8955	High Similarity	NPC153979
0.8955	High Similarity	NPC332594
0.8955	High Similarity	NPC209560
0.8955	High Similarity	NPC317119
0.8955	High Similarity	NPC472419
0.8955	High Similarity	NPC294409
0.8955	High Similarity	NPC116632
0.8955	High Similarity	NPC266597
0.8955	High Similarity	NPC303644
0.8955	High Similarity	NPC188879
0.8947	High Similarity	NPC131039
0.8947	High Similarity	NPC13575
0.8947	High Similarity	NPC39426
0.8947	High Similarity	NPC234560
0.8947	High Similarity	NPC156092
0.8943	High Similarity	NPC241089
0.8939	High Similarity	NPC223457
0.8931	High Similarity	NPC475008
0.8931	High Similarity	NPC112192
0.8931	High Similarity	NPC189106
0.8931	High Similarity	NPC186097
0.8931	High Similarity	NPC164236
0.8931	High Similarity	NPC475009
0.8931	High Similarity	NPC66384
0.8931	High Similarity	NPC65060
0.8931	High Similarity	NPC309717
0.8931	High Similarity	NPC27490
0.8931	High Similarity	NPC128348
0.8913	High Similarity	NPC472034
0.8897	High Similarity	NPC67650
0.8897	High Similarity	NPC90411
0.8897	High Similarity	NPC1704
0.8897	High Similarity	NPC307990
0.8897	High Similarity	NPC16455
0.8889	High Similarity	NPC55162
0.8889	High Similarity	NPC279668
0.8889	High Similarity	NPC12175
0.8889	High Similarity	NPC472368
0.8889	High Similarity	NPC278323
0.8889	High Similarity	NPC21350
0.8889	High Similarity	NPC90665
0.8889	High Similarity	NPC309154
0.8889	High Similarity	NPC124269
0.8889	High Similarity	NPC280284
0.8889	High Similarity	NPC188947
0.8889	High Similarity	NPC99333
0.8881	High Similarity	NPC213603
0.8881	High Similarity	NPC234133
0.8881	High Similarity	NPC124784
0.8881	High Similarity	NPC231772
0.8881	High Similarity	NPC473887
0.8881	High Similarity	NPC29353
0.8881	High Similarity	NPC47815
0.8881	High Similarity	NPC87545
0.8881	High Similarity	NPC127447
0.8881	High Similarity	NPC194281
0.8881	High Similarity	NPC235428
0.8881	High Similarity	NPC240593
0.8881	High Similarity	NPC187826
0.8872	High Similarity	NPC144027
0.8872	High Similarity	NPC125920
0.8872	High Similarity	NPC172262
0.8872	High Similarity	NPC103842
0.8872	High Similarity	NPC236974
0.8864	High Similarity	NPC10971
0.8864	High Similarity	NPC153783
0.8855	High Similarity	NPC250057
0.8849	High Similarity	NPC25844
0.8849	High Similarity	NPC472033
0.8846	High Similarity	NPC211120
0.8841	High Similarity	NPC470216
0.8841	High Similarity	NPC210425
0.8841	High Similarity	NPC86373
0.8841	High Similarity	NPC280404
0.8841	High Similarity	NPC277426
0.8828	High Similarity	NPC4164
0.8824	High Similarity	NPC477956
0.8824	High Similarity	NPC470211
0.8824	High Similarity	NPC295384
0.8824	High Similarity	NPC472366
0.8824	High Similarity	NPC49242
0.8815	High Similarity	NPC275055
0.8815	High Similarity	NPC212767
0.8815	High Similarity	NPC290291
0.8806	High Similarity	NPC9985
0.8806	High Similarity	NPC151113
0.8806	High Similarity	NPC239495
0.8806	High Similarity	NPC84699
0.8806	High Similarity	NPC60667
0.8797	High Similarity	NPC274121
0.8797	High Similarity	NPC108113
0.8797	High Similarity	NPC57601
0.8797	High Similarity	NPC175943
0.8797	High Similarity	NPC93756
0.8797	High Similarity	NPC27643
0.8797	High Similarity	NPC50898
0.8797	High Similarity	NPC213216
0.8797	High Similarity	NPC78540
0.8786	High Similarity	NPC472036
0.878	High Similarity	NPC131192
0.878	High Similarity	NPC128825
0.8777	High Similarity	NPC469953
0.8768	High Similarity	NPC472006
0.8768	High Similarity	NPC51106
0.8768	High Similarity	NPC469542
0.8759	High Similarity	NPC220106
0.8759	High Similarity	NPC259166
0.8759	High Similarity	NPC101366
0.8759	High Similarity	NPC11056

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 NPC307732 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	1002
0.2-0.3	1818
0.3-0.4	2610
0.4-0.5	1772
0.5-0.6	1091
0.6-0.7	375
0.7-0.8	118
0.8-0.85	30
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9225	High Similarity	NPD1240	Approved
0.9084	High Similarity	NPD1607	Approved
0.903	High Similarity	NPD970	Clinical (unspecified phase)
0.8947	High Similarity	NPD1510	Phase 2
0.878	High Similarity	NPD9493	Approved
0.875	High Similarity	NPD1549	Phase 2
0.8741	High Similarity	NPD1551	Phase 2
0.874	High Similarity	NPD9717	Approved
0.8676	High Similarity	NPD1550	Clinical (unspecified phase)
0.8676	High Similarity	NPD1552	Clinical (unspecified phase)
0.864	High Similarity	NPD9545	Approved
0.8623	High Similarity	NPD1878	Clinical (unspecified phase)
0.8571	High Similarity	NPD6799	Approved
0.8538	High Similarity	NPD1203	Approved
0.8414	Intermediate Similarity	NPD7411	Suspended
0.838	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2935	Discontinued
0.8309	Intermediate Similarity	NPD230	Phase 1
0.8255	Intermediate Similarity	NPD7075	Discontinued
0.8252	Intermediate Similarity	NPD2533	Approved
0.8252	Intermediate Similarity	NPD2534	Approved
0.8252	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD2532	Approved
0.8231	Intermediate Similarity	NPD422	Phase 1
0.8227	Intermediate Similarity	NPD3750	Approved
0.8219	Intermediate Similarity	NPD6599	Discontinued
0.8201	Intermediate Similarity	NPD2796	Approved
0.8182	Intermediate Similarity	NPD1511	Approved
0.8176	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD1243	Approved
0.813	Intermediate Similarity	NPD9266	Approved
0.813	Intermediate Similarity	NPD74	Approved
0.8116	Intermediate Similarity	NPD6651	Approved
0.8108	Intermediate Similarity	NPD6801	Discontinued
0.8095	Intermediate Similarity	NPD4380	Phase 2
0.8088	Intermediate Similarity	NPD411	Approved
0.8069	Intermediate Similarity	NPD1512	Approved
0.8067	Intermediate Similarity	NPD7768	Phase 2
0.806	Intermediate Similarity	NPD1019	Discontinued
0.8049	Intermediate Similarity	NPD9264	Approved
0.8049	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD9267	Approved
0.8049	Intermediate Similarity	NPD9263	Approved
0.8043	Intermediate Similarity	NPD447	Suspended
0.8028	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD920	Approved
0.8013	Intermediate Similarity	NPD3749	Approved
0.7987	Intermediate Similarity	NPD1934	Approved
0.7986	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3882	Suspended
0.7941	Intermediate Similarity	NPD6832	Phase 2
0.7935	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2801	Approved
0.7922	Intermediate Similarity	NPD6232	Discontinued
0.7902	Intermediate Similarity	NPD2800	Approved
0.7902	Intermediate Similarity	NPD2654	Approved
0.7895	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD5403	Approved
0.7881	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD3817	Phase 2
0.7877	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD5401	Approved
0.7872	Intermediate Similarity	NPD3748	Approved
0.7842	Intermediate Similarity	NPD943	Approved
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.7761	Intermediate Similarity	NPD9269	Phase 2
0.7752	Intermediate Similarity	NPD9281	Approved
0.7746	Intermediate Similarity	NPD2799	Discontinued
0.7727	Intermediate Similarity	NPD9268	Approved
0.7724	Intermediate Similarity	NPD4628	Phase 3
0.7724	Intermediate Similarity	NPD9261	Approved
0.7712	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1296	Phase 2
0.7688	Intermediate Similarity	NPD5953	Discontinued
0.7673	Intermediate Similarity	NPD7286	Phase 2
0.766	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1933	Approved
0.7647	Intermediate Similarity	NPD3225	Approved
0.7639	Intermediate Similarity	NPD2344	Approved
0.7622	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD919	Approved
0.7609	Intermediate Similarity	NPD9494	Approved
0.7603	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1164	Approved
0.7571	Intermediate Similarity	NPD2313	Discontinued
0.7536	Intermediate Similarity	NPD2798	Approved
0.7533	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5402	Approved
0.7519	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7484	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6166	Phase 2
0.7468	Intermediate Similarity	NPD5711	Approved
0.7468	Intermediate Similarity	NPD5710	Approved
0.7468	Intermediate Similarity	NPD1465	Phase 2
0.7464	Intermediate Similarity	NPD2797	Approved
0.7453	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7054	Approved
0.7447	Intermediate Similarity	NPD3764	Approved
0.7447	Intermediate Similarity	NPD3268	Approved
0.7434	Intermediate Similarity	NPD3226	Approved
0.7432	Intermediate Similarity	NPD2309	Approved
0.7429	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1778	Approved
0.7407	Intermediate Similarity	NPD7472	Approved
0.7407	Intermediate Similarity	NPD7074	Phase 3
0.7405	Intermediate Similarity	NPD1241	Discontinued
0.7405	Intermediate Similarity	NPD6959	Discontinued
0.7394	Intermediate Similarity	NPD520	Approved
0.7378	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3972	Approved
0.7372	Intermediate Similarity	NPD1481	Phase 2
0.7362	Intermediate Similarity	NPD6797	Phase 2
0.7346	Intermediate Similarity	NPD5844	Phase 1
0.7344	Intermediate Similarity	NPD1358	Approved
0.7317	Intermediate Similarity	NPD7251	Discontinued
0.7317	Intermediate Similarity	NPD6559	Discontinued
0.7308	Intermediate Similarity	NPD4288	Approved
0.7299	Intermediate Similarity	NPD1535	Discovery
0.7299	Intermediate Similarity	NPD1610	Phase 2
0.7292	Intermediate Similarity	NPD5124	Phase 1
0.7292	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2346	Discontinued
0.7279	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD7808	Phase 3
0.7266	Intermediate Similarity	NPD3134	Approved
0.7248	Intermediate Similarity	NPD7003	Approved
0.7233	Intermediate Similarity	NPD5494	Approved
0.7222	Intermediate Similarity	NPD846	Approved
0.7222	Intermediate Similarity	NPD940	Approved
0.7222	Intermediate Similarity	NPD4307	Phase 2
0.7219	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3266	Approved
0.7214	Intermediate Similarity	NPD3267	Approved
0.7211	Intermediate Similarity	NPD5408	Approved
0.7211	Intermediate Similarity	NPD5404	Approved
0.7211	Intermediate Similarity	NPD6099	Approved
0.7211	Intermediate Similarity	NPD5405	Approved
0.7211	Intermediate Similarity	NPD6100	Approved
0.7211	Intermediate Similarity	NPD5406	Approved
0.7208	Intermediate Similarity	NPD7458	Discontinued
0.7195	Intermediate Similarity	NPD1729	Discontinued
0.7188	Intermediate Similarity	NPD1247	Approved
0.7183	Intermediate Similarity	NPD4908	Phase 1
0.7181	Intermediate Similarity	NPD1652	Phase 2
0.7169	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4626	Approved
0.7152	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1283	Approved
0.7132	Intermediate Similarity	NPD1894	Discontinued
0.7115	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7390	Discontinued
0.7101	Intermediate Similarity	NPD3847	Discontinued
0.7099	Intermediate Similarity	NPD3926	Phase 2
0.7092	Intermediate Similarity	NPD1470	Approved
0.7089	Intermediate Similarity	NPD5353	Approved
0.7086	Intermediate Similarity	NPD2354	Approved
0.7083	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6798	Discontinued
0.708	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD9697	Approved
0.705	Intermediate Similarity	NPD1201	Approved
0.7032	Intermediate Similarity	NPD1653	Approved
0.7021	Intermediate Similarity	NPD1876	Approved
0.7018	Intermediate Similarity	NPD4287	Approved
0.7013	Intermediate Similarity	NPD2186	Approved
0.7013	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6104	Discontinued
0.7	Intermediate Similarity	NPD6971	Discontinued
0.6978	Remote Similarity	NPD3496	Discontinued
0.6974	Remote Similarity	NPD6190	Approved
0.6968	Remote Similarity	NPD1670	Discontinued
0.6959	Remote Similarity	NPD1898	Discontinued
0.6951	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6355	Discontinued
0.6936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6004	Phase 3
0.6933	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2353	Approved
0.6933	Remote Similarity	NPD6002	Phase 3
0.6933	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6005	Phase 3
0.6929	Remote Similarity	NPD1281	Approved
0.6928	Remote Similarity	NPD7440	Discontinued

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