NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	196.07
Volume:	197.575
LogP:	2.637
LogD:	2.699
LogS:	-2.568
# Rotatable Bonds:	3
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	1.899
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.573
MDCK Permeability:	1.6673940990585834e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.274

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.785
Plasma Protein Binding (PPB):	90.21588897705078%
Volume Distribution (VD):	0.774
Pgp-substrate:	9.43570327758789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.611
CYP2C19-substrate:	0.682
CYP2C9-inhibitor:	0.246
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.508
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.634
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	11.735
Half-life (T1/2):	0.784

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.495
AMES Toxicity:	0.174
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.138
Skin Sensitization:	0.26
Carcinogencity:	0.032
Eye Corrosion:	0.228
Eye Irritation:	0.986
Respiratory Toxicity:	0.479

Download Data

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

Natural Product: NPC180905

Natural Product ID:	NPC180905
*Common Name:**	Methyl 2-Hydroxy-4-Methoxy-6-Methylbenzoate
IUPAC Name:	methyl 2-hydroxy-4-methoxy-6-methylbenzoate
Synonyms:
Standard InCHIKey:	PFVPJOAAHSOENR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O4/c1-6-4-7(13-2)5-8(11)9(6)10(12)14-3/h4-5,11H,1-3H3
SMILES:	Cc1cc(cc(c1C(=O)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1595401
PubChem CID:	596344
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
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	Wrocław, Poland	2004–2005	DOI[10.1016/J.FOODCHEM.2006.08.014]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jf950732o]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jf980687v]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10775096]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	flowers	n.a.	n.a.	PMID[15974620]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[1622242]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16659156]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16668466]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20963508]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	Tekirdag, Turkey		PMID[24499198]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25053043]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25070365]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25369450]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[25369450]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[26599832]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29272126]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Hypocotyl	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4934	Phaseolus vulgaris	Species	Fabaceae	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
Potency	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	35481.3	nM	PMID[547802]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	39810.7	nM	PMID[547802]
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency	n.a.	5011.9	nM	PMID[547802]

☑ 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 NPC180905 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	332
0.1-0.2	1642
0.2-0.3	4325
0.3-0.4	9923
0.4-0.5	8161
0.5-0.6	3582
0.6-0.7	6130
0.7-0.8	6562
0.8-0.85	1498
0.85-0.9	442
0.9-0.95	85
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC182496
0.9846	High Similarity	NPC135837
0.9688	High Similarity	NPC219892
0.9688	High Similarity	NPC189823
0.9624	High Similarity	NPC165172
0.9552	High Similarity	NPC67650
0.9552	High Similarity	NPC90411
0.9552	High Similarity	NPC1704
0.9552	High Similarity	NPC475730
0.9538	High Similarity	NPC153783
0.9481	High Similarity	NPC250755
0.9481	High Similarity	NPC474385
0.9466	High Similarity	NPC175943
0.9453	High Similarity	NPC293453
0.9412	High Similarity	NPC469542
0.9412	High Similarity	NPC51106
0.9412	High Similarity	NPC472006
0.9407	High Similarity	NPC220106
0.9343	High Similarity	NPC277426
0.9343	High Similarity	NPC95123
0.9343	High Similarity	NPC210425
0.9343	High Similarity	NPC66404
0.9343	High Similarity	NPC280404
0.9343	High Similarity	NPC86373
0.9338	High Similarity	NPC105648
0.9323	High Similarity	NPC235115
0.9323	High Similarity	NPC158481
0.9308	High Similarity	NPC307732
0.9308	High Similarity	NPC42292
0.9275	High Similarity	NPC312789
0.9275	High Similarity	NPC134621
0.9275	High Similarity	NPC472034
0.9259	High Similarity	NPC32360
0.9259	High Similarity	NPC268052
0.9259	High Similarity	NPC92655
0.9254	High Similarity	NPC70380
0.9254	High Similarity	NPC194579
0.9225	High Similarity	NPC128428
0.9225	High Similarity	NPC305518
0.9219	High Similarity	NPC262671
0.9219	High Similarity	NPC201728
0.9209	High Similarity	NPC267509
0.9209	High Similarity	NPC163846
0.9209	High Similarity	NPC472033
0.9209	High Similarity	NPC225173
0.9209	High Similarity	NPC138978
0.9209	High Similarity	NPC237208
0.9209	High Similarity	NPC107625
0.9197	High Similarity	NPC469579
0.9185	High Similarity	NPC212693
0.9185	High Similarity	NPC478200
0.9185	High Similarity	NPC33144
0.9185	High Similarity	NPC191835
0.9185	High Similarity	NPC94248
0.9179	High Similarity	NPC242712
0.9179	High Similarity	NPC50455
0.9143	High Similarity	NPC210320
0.9143	High Similarity	NPC125801
0.9143	High Similarity	NPC14098
0.9143	High Similarity	NPC472036
0.9137	High Similarity	NPC29577
0.9137	High Similarity	NPC32470
0.9137	High Similarity	NPC473692
0.9124	High Similarity	NPC158634
0.9118	High Similarity	NPC57380
0.9118	High Similarity	NPC247409
0.9118	High Similarity	NPC105456
0.9118	High Similarity	NPC52358
0.9118	High Similarity	NPC471819
0.9118	High Similarity	NPC139634
0.9084	High Similarity	NPC69235
0.9084	High Similarity	NPC212379
0.9078	High Similarity	NPC215711
0.9078	High Similarity	NPC471642
0.9078	High Similarity	NPC240253
0.9078	High Similarity	NPC471641
0.9078	High Similarity	NPC153417
0.9078	High Similarity	NPC172329
0.9078	High Similarity	NPC2569
0.9078	High Similarity	NPC73411
0.9078	High Similarity	NPC240622
0.9071	High Similarity	NPC260946
0.9058	High Similarity	NPC49108
0.9058	High Similarity	NPC94076
0.9058	High Similarity	NPC182255
0.9051	High Similarity	NPC158472
0.9051	High Similarity	NPC99441
0.9044	High Similarity	NPC472602
0.9014	High Similarity	NPC476684
0.9014	High Similarity	NPC77325
0.9014	High Similarity	NPC233267
0.9014	High Similarity	NPC4423
0.9014	High Similarity	NPC270160
0.9014	High Similarity	NPC237440
0.9014	High Similarity	NPC291049
0.9008	High Similarity	NPC186098
0.9008	High Similarity	NPC80694
0.9008	High Similarity	NPC41263
0.9007	High Similarity	NPC12305
0.9	High Similarity	NPC95309
0.8993	High Similarity	NPC310340
0.8993	High Similarity	NPC84266
0.8992	High Similarity	NPC6888
0.8986	High Similarity	NPC478201
0.8986	High Similarity	NPC472035
0.8986	High Similarity	NPC478217
0.8986	High Similarity	NPC37530
0.8986	High Similarity	NPC244923
0.8986	High Similarity	NPC313123
0.8986	High Similarity	NPC53649
0.8986	High Similarity	NPC275734
0.8978	High Similarity	NPC275356
0.8978	High Similarity	NPC88269
0.8971	High Similarity	NPC476333
0.8971	High Similarity	NPC472367
0.8971	High Similarity	NPC472364
0.8971	High Similarity	NPC473391
0.8971	High Similarity	NPC71256
0.8951	High Similarity	NPC119929
0.8951	High Similarity	NPC96501
0.8951	High Similarity	NPC295036
0.8951	High Similarity	NPC470107
0.8951	High Similarity	NPC469670
0.8951	High Similarity	NPC60413
0.8951	High Similarity	NPC469619
0.8944	High Similarity	NPC105415
0.8944	High Similarity	NPC37139
0.8939	High Similarity	NPC230818
0.8929	High Similarity	NPC19896
0.8929	High Similarity	NPC475201
0.8921	High Similarity	NPC96692
0.8921	High Similarity	NPC82913
0.8913	High Similarity	NPC155205
0.8913	High Similarity	NPC472600
0.8913	High Similarity	NPC472601
0.8889	High Similarity	NPC227166
0.8889	High Similarity	NPC70016
0.8889	High Similarity	NPC133856
0.8889	High Similarity	NPC204350
0.8889	High Similarity	NPC200773
0.8889	High Similarity	NPC240768
0.8889	High Similarity	NPC215921
0.8881	High Similarity	NPC6923
0.8881	High Similarity	NPC475589
0.8881	High Similarity	NPC198927
0.8881	High Similarity	NPC27490
0.8881	High Similarity	NPC31872
0.8881	High Similarity	NPC473584
0.8872	High Similarity	NPC17840
0.8872	High Similarity	NPC247477
0.8872	High Similarity	NPC84772
0.8872	High Similarity	NPC296158
0.8865	High Similarity	NPC75694
0.8857	High Similarity	NPC159721
0.8857	High Similarity	NPC478202
0.8849	High Similarity	NPC472604
0.8849	High Similarity	NPC472603
0.8849	High Similarity	NPC472605
0.8841	High Similarity	NPC472368
0.8832	High Similarity	NPC474849
0.8832	High Similarity	NPC178467
0.8832	High Similarity	NPC149372
0.8832	High Similarity	NPC65837
0.8832	High Similarity	NPC193792
0.8832	High Similarity	NPC474771
0.8828	High Similarity	NPC271681
0.8828	High Similarity	NPC175978
0.8828	High Similarity	NPC273483
0.8828	High Similarity	NPC167903
0.8819	High Similarity	NPC158866
0.8819	High Similarity	NPC194379
0.8819	High Similarity	NPC307780
0.8819	High Similarity	NPC179178
0.8819	High Similarity	NPC150928
0.8819	High Similarity	NPC309979
0.8815	High Similarity	NPC212631
0.8815	High Similarity	NPC129132
0.8815	High Similarity	NPC87231
0.8815	High Similarity	NPC25937
0.8815	High Similarity	NPC203817
0.8815	High Similarity	NPC257756
0.8815	High Similarity	NPC205468
0.8806	High Similarity	NPC470831
0.8806	High Similarity	NPC5515
0.8806	High Similarity	NPC214702
0.8806	High Similarity	NPC324482
0.8806	High Similarity	NPC270369
0.8797	High Similarity	NPC78662
0.8797	High Similarity	NPC8005
0.8794	High Similarity	NPC42540
0.8794	High Similarity	NPC478203
0.8794	High Similarity	NPC151607
0.8794	High Similarity	NPC210966
0.8794	High Similarity	NPC126882
0.8786	High Similarity	NPC471644
0.8786	High Similarity	NPC322112
0.8786	High Similarity	NPC471640
0.8777	High Similarity	NPC472366
0.8768	High Similarity	NPC9121
0.8768	High Similarity	NPC212767

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 NPC180905 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	1023
0.2-0.3	1787
0.3-0.4	2607
0.4-0.5	1735
0.5-0.6	1102
0.6-0.7	433
0.7-0.8	141
0.8-0.85	23
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9697	High Similarity	NPD970	Clinical (unspecified phase)
0.8865	High Similarity	NPD2533	Approved
0.8865	High Similarity	NPD2532	Approved
0.8865	High Similarity	NPD2534	Approved
0.8741	High Similarity	NPD1240	Approved
0.8623	High Similarity	NPD1510	Phase 2
0.8613	High Similarity	NPD1607	Approved
0.8514	High Similarity	NPD7819	Suspended
0.8369	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD6232	Discontinued
0.8322	Intermediate Similarity	NPD3750	Approved
0.8322	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD1549	Phase 2
0.8298	Intermediate Similarity	NPD1551	Phase 2
0.8298	Intermediate Similarity	NPD2935	Discontinued
0.8276	Intermediate Similarity	NPD1511	Approved
0.8273	Intermediate Similarity	NPD230	Phase 1
0.8219	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD7473	Discontinued
0.8163	Intermediate Similarity	NPD1512	Approved
0.8154	Intermediate Similarity	NPD9493	Approved
0.8151	Intermediate Similarity	NPD6799	Approved
0.8134	Intermediate Similarity	NPD9717	Approved
0.8105	Intermediate Similarity	NPD3749	Approved
0.8099	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1934	Approved
0.8058	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD9545	Approved
0.8026	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2801	Approved
0.8013	Intermediate Similarity	NPD7411	Suspended
0.8013	Intermediate Similarity	NPD5710	Approved
0.8013	Intermediate Similarity	NPD5711	Approved
0.8	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD2800	Approved
0.7987	Intermediate Similarity	NPD7075	Discontinued
0.7974	Intermediate Similarity	NPD3817	Phase 2
0.7972	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD3748	Approved
0.7958	Intermediate Similarity	NPD6651	Approved
0.7956	Intermediate Similarity	NPD1203	Approved
0.7949	Intermediate Similarity	NPD6959	Discontinued
0.7947	Intermediate Similarity	NPD6599	Discontinued
0.7929	Intermediate Similarity	NPD411	Approved
0.7926	Intermediate Similarity	NPD422	Phase 1
0.7922	Intermediate Similarity	NPD3882	Suspended
0.7922	Intermediate Similarity	NPD7768	Phase 2
0.7917	Intermediate Similarity	NPD2796	Approved
0.7908	Intermediate Similarity	NPD1465	Phase 2
0.7908	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD447	Suspended
0.7857	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4380	Phase 2
0.7823	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD943	Approved
0.7806	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3226	Approved
0.7755	Intermediate Similarity	NPD2654	Approved
0.7748	Intermediate Similarity	NPD920	Approved
0.7737	Intermediate Similarity	NPD9269	Phase 2
0.7737	Intermediate Similarity	NPD1608	Approved
0.7727	Intermediate Similarity	NPD6801	Discontinued
0.7718	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD9268	Approved
0.7671	Intermediate Similarity	NPD6099	Approved
0.7671	Intermediate Similarity	NPD6100	Approved
0.7667	Intermediate Similarity	NPD7390	Discontinued
0.7654	Intermediate Similarity	NPD5844	Phase 1
0.7647	Intermediate Similarity	NPD4626	Approved
0.7643	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD1283	Approved
0.7619	Intermediate Similarity	NPD2346	Discontinued
0.7616	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2799	Discontinued
0.7595	Intermediate Similarity	NPD919	Approved
0.7584	Intermediate Similarity	NPD4628	Phase 3
0.7578	Intermediate Similarity	NPD6166	Phase 2
0.7578	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3764	Approved
0.7551	Intermediate Similarity	NPD5406	Approved
0.7551	Intermediate Similarity	NPD5404	Approved
0.7551	Intermediate Similarity	NPD5405	Approved
0.7551	Intermediate Similarity	NPD5408	Approved
0.7546	Intermediate Similarity	NPD7054	Approved
0.7538	Intermediate Similarity	NPD74	Approved
0.7538	Intermediate Similarity	NPD9266	Approved
0.7536	Intermediate Similarity	NPD1201	Approved
0.7535	Intermediate Similarity	NPD6832	Phase 2
0.7518	Intermediate Similarity	NPD1019	Discontinued
0.7518	Intermediate Similarity	NPD17	Approved
0.7517	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5402	Approved
0.7516	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD7472	Approved
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7481	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD9494	Approved
0.7462	Intermediate Similarity	NPD9264	Approved
0.7462	Intermediate Similarity	NPD9263	Approved
0.7462	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD9267	Approved
0.7455	Intermediate Similarity	NPD6797	Phase 2
0.7455	Intermediate Similarity	NPD5953	Discontinued
0.7447	Intermediate Similarity	NPD1164	Approved
0.7447	Intermediate Similarity	NPD1470	Approved
0.7431	Intermediate Similarity	NPD1296	Phase 2
0.741	Intermediate Similarity	NPD1281	Approved
0.741	Intermediate Similarity	NPD7251	Discontinued
0.7405	Intermediate Similarity	NPD4288	Approved
0.7394	Intermediate Similarity	NPD2798	Approved
0.7391	Intermediate Similarity	NPD1778	Approved
0.7389	Intermediate Similarity	NPD37	Approved
0.7365	Intermediate Similarity	NPD7808	Phase 3
0.7351	Intermediate Similarity	NPD7003	Approved
0.7333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7286	Phase 2
0.7329	Intermediate Similarity	NPD5494	Approved
0.7324	Intermediate Similarity	NPD2797	Approved
0.732	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5691	Approved
0.731	Intermediate Similarity	NPD3268	Approved
0.731	Intermediate Similarity	NPD2313	Discontinued
0.731	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6559	Discontinued
0.7303	Intermediate Similarity	NPD2309	Approved
0.7286	Intermediate Similarity	NPD1610	Phase 2
0.7284	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6234	Discontinued
0.7254	Intermediate Similarity	NPD3225	Approved
0.725	Intermediate Similarity	NPD4966	Approved
0.725	Intermediate Similarity	NPD4967	Phase 2
0.725	Intermediate Similarity	NPD4965	Approved
0.7248	Intermediate Similarity	NPD7033	Discontinued
0.7248	Intermediate Similarity	NPD4308	Phase 3
0.7246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1548	Phase 1
0.7239	Intermediate Similarity	NPD7229	Phase 3
0.7225	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD9281	Approved
0.7197	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3926	Phase 2
0.7195	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4749	Approved
0.7178	Intermediate Similarity	NPD1247	Approved
0.7172	Intermediate Similarity	NPD4908	Phase 1
0.7172	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1933	Approved
0.716	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD9261	Approved
0.7153	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1876	Approved
0.7123	Intermediate Similarity	NPD4625	Phase 3
0.7113	Intermediate Similarity	NPD3972	Approved
0.7113	Intermediate Similarity	NPD1481	Phase 2
0.711	Intermediate Similarity	NPD4287	Approved
0.7103	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4060	Phase 1
0.7092	Intermediate Similarity	NPD3496	Discontinued
0.7089	Intermediate Similarity	NPD7458	Discontinued
0.7083	Intermediate Similarity	NPD3266	Approved
0.7083	Intermediate Similarity	NPD3267	Approved
0.7081	Intermediate Similarity	NPD5353	Approved
0.7075	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1651	Approved
0.7066	Intermediate Similarity	NPD3751	Discontinued
0.7055	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5124	Phase 1
0.7042	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1535	Discovery
0.7039	Intermediate Similarity	NPD1471	Phase 3
0.7011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3027	Phase 3
0.7007	Intermediate Similarity	NPD1241	Discontinued
0.7006	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6971	Discontinued
0.6988	Remote Similarity	NPD5242	Approved
0.698	Remote Similarity	NPD2979	Phase 3
0.698	Remote Similarity	NPD4307	Phase 2
0.698	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1613	Approved
0.6974	Remote Similarity	NPD4477	Approved
0.6974	Remote Similarity	NPD4476	Approved
0.6964	Remote Similarity	NPD7177	Discontinued
0.6964	Remote Similarity	NPD7228	Approved
0.6959	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1652	Phase 2

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