NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.03
Volume:	154.426
LogP:	1.788
LogD:	1.438
LogS:	-2.528
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.679
Synthetic Accessibility Score:	1.694
Fsp3:	0.125
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:	-4.96
MDCK Permeability:	1.622326635697391e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.628

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.362
Plasma Protein Binding (PPB):	76.8894271850586%
Volume Distribution (VD):	0.278
Pgp-substrate:	25.941865921020508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.369
CYP1A2-substrate:	0.218
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.118
CYP2D6-inhibitor:	0.169
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	9.023
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.431
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.237
Carcinogencity:	0.842
Eye Corrosion:	0.057
Eye Irritation:	0.974
Respiratory Toxicity:	0.115

Download Data

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

Natural Product: NPC45404

Natural Product ID:	NPC45404
*Common Name:**	Piperonylic Acid
IUPAC Name:	1,3-benzodioxole-5-carboxylic acid
Synonyms:	Piperonylic Acid
Standard InCHIKey:	VDVJGIYXDVPQLP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H6O4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H,9,10)
SMILES:	OC(=O)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL573781
PubChem CID:	7196
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO9553	Phyllodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921433]
NPO3037	Derris indica	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[19515570]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO5131	Scorzonera hispanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5131	Scorzonera hispanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9989	Cotylelobium scabriusculum	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12591	Archaster typicus	Species	Archasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4746	Centaurea arenaria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6386	Gutenbergia cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9553	Phyllodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8601	Petrosia volcano	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9361	Aplophyllum villosum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28392	Macrosiphum liriodendri	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1326	Cratystylis conocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13042	Diospyros abyssinica	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22899	Phaeotremella fagi	Species	Phaeotremellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28510	Aspergillus pseudodeflectus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28218	Asplenium adiantum-nigrum	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12233	Diospyros peregrina	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11333	Trapa japonica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5131	Scorzonera hispanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12367	Diospyros elliptifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13555	Beaucarnea recurvata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7870	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12819	Clitocybe subilludens	Species	Tricholomataceae	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	4
Others	3
Potency	2

Activity Type	# Activity
Individual Protein	4
ORGANISM	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	39810.7	nM	PMID[509342]
NPT2957	Individual Protein	Trans-cinnamate 4-monooxygenase	Populus kitakamiensis	Inhibition	=	58.0	%	PMID[509345]
NPT2957	Individual Protein	Trans-cinnamate 4-monooxygenase	Populus kitakamiensis	IC50	>	100000.0	nM	PMID[509345]
NPT2	Others	Unspecified		IC50	=	18.4	%	PMID[509341]
NPT1	Others	Radical scavenging activity		SC50	=	2.4	%	PMID[509341]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	19952.6	nM	PMID[509342]
NPT21912	ORGANISM	Hylobius abietis	Hylobius abietis	AFI	=	14.0	%	PMID[509344]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[509346]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[509346]

☑ 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 NPC45404 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	371
0.1-0.2	1824
0.2-0.3	5027
0.3-0.4	10405
0.4-0.5	7010
0.5-0.6	4112
0.6-0.7	9108
0.7-0.8	4617
0.8-0.85	185
0.85-0.9	31
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.938	High Similarity	NPC285776
0.9167	High Similarity	NPC283823
0.9167	High Similarity	NPC159418
0.9091	High Similarity	NPC111888
0.907	High Similarity	NPC154275
0.8955	High Similarity	NPC155098
0.8855	High Similarity	NPC286683
0.8846	High Similarity	NPC120066
0.8759	High Similarity	NPC25305
0.8759	High Similarity	NPC112068
0.8759	High Similarity	NPC95679
0.8759	High Similarity	NPC110899
0.8759	High Similarity	NPC125417
0.8712	High Similarity	NPC158654
0.8705	High Similarity	NPC326065
0.8657	High Similarity	NPC299010
0.8613	High Similarity	NPC38101
0.8601	High Similarity	NPC153620
0.8601	High Similarity	NPC24257
0.8594	High Similarity	NPC57501
0.8582	High Similarity	NPC226855
0.8581	High Similarity	NPC109765
0.8571	High Similarity	NPC281020
0.8571	High Similarity	NPC28398
0.8562	High Similarity	NPC36130
0.8562	High Similarity	NPC134905
0.8561	High Similarity	NPC207516
0.8531	High Similarity	NPC473867
0.8523	High Similarity	NPC202495
0.8523	High Similarity	NPC226759
0.8521	High Similarity	NPC473090
0.8521	High Similarity	NPC469615
0.8521	High Similarity	NPC46880
0.8478	Intermediate Similarity	NPC139519
0.8467	Intermediate Similarity	NPC288743
0.8462	Intermediate Similarity	NPC213900
0.8462	Intermediate Similarity	NPC469683
0.8462	Intermediate Similarity	NPC113397
0.845	Intermediate Similarity	NPC61779
0.8446	Intermediate Similarity	NPC191046
0.8446	Intermediate Similarity	NPC194095
0.8446	Intermediate Similarity	NPC327032
0.8444	Intermediate Similarity	NPC94810
0.8435	Intermediate Similarity	NPC289438
0.8435	Intermediate Similarity	NPC288316
0.8433	Intermediate Similarity	NPC32163
0.8433	Intermediate Similarity	NPC16651
0.8425	Intermediate Similarity	NPC227980
0.8425	Intermediate Similarity	NPC205054
0.8411	Intermediate Similarity	NPC218471
0.8411	Intermediate Similarity	NPC239818
0.8389	Intermediate Similarity	NPC10205
0.8382	Intermediate Similarity	NPC477694
0.8382	Intermediate Similarity	NPC477705
0.8378	Intermediate Similarity	NPC105827
0.8378	Intermediate Similarity	NPC310661
0.8378	Intermediate Similarity	NPC137813
0.8358	Intermediate Similarity	NPC475236
0.8356	Intermediate Similarity	NPC111785
0.8345	Intermediate Similarity	NPC208760
0.8344	Intermediate Similarity	NPC68619
0.8333	Intermediate Similarity	NPC471405
0.8333	Intermediate Similarity	NPC307006
0.8333	Intermediate Similarity	NPC327052
0.8333	Intermediate Similarity	NPC129889
0.8321	Intermediate Similarity	NPC477706
0.8321	Intermediate Similarity	NPC264145
0.8321	Intermediate Similarity	NPC225245
0.8311	Intermediate Similarity	NPC118332
0.8308	Intermediate Similarity	NPC156654
0.8298	Intermediate Similarity	NPC325625
0.8296	Intermediate Similarity	NPC117237
0.8296	Intermediate Similarity	NPC203719
0.8295	Intermediate Similarity	NPC240664
0.8295	Intermediate Similarity	NPC212643
0.8295	Intermediate Similarity	NPC199209
0.8289	Intermediate Similarity	NPC474770
0.8288	Intermediate Similarity	NPC472969
0.8278	Intermediate Similarity	NPC133984
0.8278	Intermediate Similarity	NPC474990
0.8278	Intermediate Similarity	NPC472860
0.8276	Intermediate Similarity	NPC224687
0.8264	Intermediate Similarity	NPC134975
0.8264	Intermediate Similarity	NPC258307
0.8261	Intermediate Similarity	NPC50763
0.8255	Intermediate Similarity	NPC35544
0.8255	Intermediate Similarity	NPC308555
0.8255	Intermediate Similarity	NPC104728
0.8255	Intermediate Similarity	NPC44730
0.8247	Intermediate Similarity	NPC100420
0.8243	Intermediate Similarity	NPC234152
0.8243	Intermediate Similarity	NPC243891
0.8231	Intermediate Similarity	NPC476394
0.8231	Intermediate Similarity	NPC205502
0.8231	Intermediate Similarity	NPC98809
0.8224	Intermediate Similarity	NPC289811
0.8224	Intermediate Similarity	NPC215375
0.8224	Intermediate Similarity	NPC160780
0.8224	Intermediate Similarity	NPC62518
0.8219	Intermediate Similarity	NPC178097
0.8219	Intermediate Similarity	NPC32058
0.8219	Intermediate Similarity	NPC85734
0.8214	Intermediate Similarity	NPC274613
0.8212	Intermediate Similarity	NPC261090
0.8209	Intermediate Similarity	NPC145134
0.8207	Intermediate Similarity	NPC108455
0.8201	Intermediate Similarity	NPC304929
0.8201	Intermediate Similarity	NPC1321
0.8201	Intermediate Similarity	NPC239855
0.8201	Intermediate Similarity	NPC156124
0.8195	Intermediate Similarity	NPC291189
0.8195	Intermediate Similarity	NPC69403
0.8194	Intermediate Similarity	NPC242756
0.8188	Intermediate Similarity	NPC267091
0.8182	Intermediate Similarity	NPC476011
0.8182	Intermediate Similarity	NPC327187
0.8182	Intermediate Similarity	NPC295317
0.8176	Intermediate Similarity	NPC473091
0.8176	Intermediate Similarity	NPC37220
0.817	Intermediate Similarity	NPC239966
0.817	Intermediate Similarity	NPC203020
0.817	Intermediate Similarity	NPC474936
0.817	Intermediate Similarity	NPC285973
0.817	Intermediate Similarity	NPC225624
0.8169	Intermediate Similarity	NPC233780
0.8168	Intermediate Similarity	NPC69670
0.8158	Intermediate Similarity	NPC1913
0.8158	Intermediate Similarity	NPC167595
0.8156	Intermediate Similarity	NPC160425
0.8151	Intermediate Similarity	NPC30890
0.8151	Intermediate Similarity	NPC3982
0.8151	Intermediate Similarity	NPC296575
0.8146	Intermediate Similarity	NPC18954
0.8146	Intermediate Similarity	NPC254163
0.8143	Intermediate Similarity	NPC237330
0.814	Intermediate Similarity	NPC220540
0.8138	Intermediate Similarity	NPC229036
0.8134	Intermediate Similarity	NPC474691
0.8133	Intermediate Similarity	NPC157898
0.8121	Intermediate Similarity	NPC96501
0.812	Intermediate Similarity	NPC177291
0.812	Intermediate Similarity	NPC194416
0.8117	Intermediate Similarity	NPC260640
0.8117	Intermediate Similarity	NPC472859
0.8117	Intermediate Similarity	NPC25389
0.8117	Intermediate Similarity	NPC162668
0.8117	Intermediate Similarity	NPC295009
0.8117	Intermediate Similarity	NPC311803
0.8116	Intermediate Similarity	NPC298268
0.8116	Intermediate Similarity	NPC66905
0.8112	Intermediate Similarity	NPC470855
0.8112	Intermediate Similarity	NPC4796
0.8108	Intermediate Similarity	NPC75945
0.8105	Intermediate Similarity	NPC76211
0.8105	Intermediate Similarity	NPC287872
0.8105	Intermediate Similarity	NPC74319
0.8102	Intermediate Similarity	NPC304747
0.8099	Intermediate Similarity	NPC14022
0.8095	Intermediate Similarity	NPC88345
0.8092	Intermediate Similarity	NPC261484
0.8085	Intermediate Similarity	NPC18646
0.8082	Intermediate Similarity	NPC474158
0.8077	Intermediate Similarity	NPC131192
0.8077	Intermediate Similarity	NPC180586
0.8074	Intermediate Similarity	NPC221798
0.8071	Intermediate Similarity	NPC114116
0.8069	Intermediate Similarity	NPC299154
0.8069	Intermediate Similarity	NPC125134
0.8069	Intermediate Similarity	NPC312256
0.8069	Intermediate Similarity	NPC137920
0.8069	Intermediate Similarity	NPC86455
0.8067	Intermediate Similarity	NPC75695
0.8067	Intermediate Similarity	NPC104353
0.8065	Intermediate Similarity	NPC33298
0.8065	Intermediate Similarity	NPC206815
0.8065	Intermediate Similarity	NPC285108
0.8065	Intermediate Similarity	NPC76687
0.8062	Intermediate Similarity	NPC294941
0.8058	Intermediate Similarity	NPC104854
0.8058	Intermediate Similarity	NPC318799
0.8056	Intermediate Similarity	NPC80098
0.8056	Intermediate Similarity	NPC50823
0.8054	Intermediate Similarity	NPC12854
0.8052	Intermediate Similarity	NPC269906
0.8052	Intermediate Similarity	NPC119125
0.8052	Intermediate Similarity	NPC289346
0.8052	Intermediate Similarity	NPC166277
0.8042	Intermediate Similarity	NPC226005
0.8042	Intermediate Similarity	NPC239943
0.8039	Intermediate Similarity	NPC82733
0.8039	Intermediate Similarity	NPC76458
0.8028	Intermediate Similarity	NPC156892
0.8028	Intermediate Similarity	NPC156307
0.8028	Intermediate Similarity	NPC326847
0.8028	Intermediate Similarity	NPC102260
0.8028	Intermediate Similarity	NPC230968
0.8028	Intermediate Similarity	NPC475111
0.8028	Intermediate Similarity	NPC90431
0.8027	Intermediate Similarity	NPC287495
0.8027	Intermediate Similarity	NPC98356

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 NPC45404 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	933
0.2-0.3	1923
0.3-0.4	2690
0.4-0.5	1718
0.5-0.6	1040
0.6-0.7	413
0.7-0.8	84
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8592	High Similarity	NPD6143	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD9494	Approved
0.8288	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD230	Phase 1
0.8071	Intermediate Similarity	NPD447	Suspended
0.803	Intermediate Similarity	NPD9268	Approved
0.7955	Intermediate Similarity	NPD9545	Approved
0.7926	Intermediate Similarity	NPD9269	Phase 2
0.7862	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD7685	Pre-registration
0.7662	Intermediate Similarity	NPD37	Approved
0.7656	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4628	Phase 3
0.763	Intermediate Similarity	NPD1357	Approved
0.7628	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3882	Suspended
0.7613	Intermediate Similarity	NPD1465	Phase 2
0.7597	Intermediate Similarity	NPD6386	Approved
0.7597	Intermediate Similarity	NPD6385	Approved
0.7591	Intermediate Similarity	NPD3705	Approved
0.7516	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD4966	Approved
0.7516	Intermediate Similarity	NPD4965	Approved
0.7515	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2801	Approved
0.7483	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD3764	Approved
0.7482	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6190	Approved
0.7452	Intermediate Similarity	NPD3817	Phase 2
0.7448	Intermediate Similarity	NPD1933	Approved
0.7436	Intermediate Similarity	NPD1934	Approved
0.7421	Intermediate Similarity	NPD6234	Discontinued
0.741	Intermediate Similarity	NPD1608	Approved
0.7403	Intermediate Similarity	NPD1653	Approved
0.74	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1512	Approved
0.7381	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7054	Approved
0.7365	Intermediate Similarity	NPD2935	Discontinued
0.7362	Intermediate Similarity	NPD7473	Discontinued
0.7355	Intermediate Similarity	NPD7458	Discontinued
0.7353	Intermediate Similarity	NPD5536	Phase 2
0.7342	Intermediate Similarity	NPD5353	Approved
0.7333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD7472	Approved
0.7329	Intermediate Similarity	NPD7199	Phase 2
0.732	Intermediate Similarity	NPD2533	Approved
0.732	Intermediate Similarity	NPD2534	Approved
0.732	Intermediate Similarity	NPD2532	Approved
0.7312	Intermediate Similarity	NPD919	Approved
0.7297	Intermediate Similarity	NPD1510	Phase 2
0.7293	Intermediate Similarity	NPD228	Approved
0.7286	Intermediate Similarity	NPD9717	Approved
0.7278	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5844	Phase 1
0.726	Intermediate Similarity	NPD1240	Approved
0.725	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD411	Approved
0.7239	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7808	Phase 3
0.72	Intermediate Similarity	NPD7266	Discontinued
0.7197	Intermediate Similarity	NPD7028	Phase 2
0.7194	Intermediate Similarity	NPD17	Approved
0.7186	Intermediate Similarity	NPD6797	Phase 2
0.717	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1607	Approved
0.716	Intermediate Similarity	NPD5494	Approved
0.7153	Intermediate Similarity	NPD9493	Approved
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD7251	Discontinued
0.7134	Intermediate Similarity	NPD5242	Approved
0.7134	Intermediate Similarity	NPD824	Approved
0.7133	Intermediate Similarity	NPD1203	Approved
0.7133	Intermediate Similarity	NPD1551	Phase 2
0.7121	Intermediate Similarity	NPD1358	Approved
0.7117	Intermediate Similarity	NPD1247	Approved
0.7108	Intermediate Similarity	NPD7228	Approved
0.7097	Intermediate Similarity	NPD3146	Approved
0.7097	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1778	Approved
0.7067	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1283	Approved
0.7059	Intermediate Similarity	NPD4110	Phase 3
0.7059	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3750	Approved
0.7042	Intermediate Similarity	NPD1481	Phase 2
0.7041	Intermediate Similarity	NPD6559	Discontinued
0.7039	Intermediate Similarity	NPD1549	Phase 2
0.7032	Intermediate Similarity	NPD4357	Discontinued
0.7025	Intermediate Similarity	NPD3226	Approved
0.7007	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2313	Discontinued
0.7006	Intermediate Similarity	NPD920	Approved
0.6988	Remote Similarity	NPD6166	Phase 2
0.6988	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4380	Phase 2
0.6974	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2344	Approved
0.6974	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1535	Discovery
0.6968	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7819	Suspended
0.6954	Remote Similarity	NPD2799	Discontinued
0.6941	Remote Similarity	NPD7039	Approved
0.6941	Remote Similarity	NPD7038	Approved
0.6939	Remote Similarity	NPD3027	Phase 3
0.6934	Remote Similarity	NPD1241	Discontinued
0.6933	Remote Similarity	NPD3749	Approved
0.6933	Remote Similarity	NPD7075	Discontinued
0.6933	Remote Similarity	NPD2492	Phase 1
0.6928	Remote Similarity	NPD3926	Phase 2
0.6923	Remote Similarity	NPD3972	Approved
0.6914	Remote Similarity	NPD5402	Approved
0.6909	Remote Similarity	NPD2821	Approved
0.6909	Remote Similarity	NPD8127	Discontinued
0.6903	Remote Similarity	NPD2354	Approved
0.6883	Remote Similarity	NPD1243	Approved
0.6879	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6599	Discontinued
0.6867	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD9263	Approved
0.6866	Remote Similarity	NPD9267	Approved
0.6866	Remote Similarity	NPD9264	Approved
0.6863	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2346	Discontinued
0.6853	Remote Similarity	NPD1091	Approved
0.6853	Remote Similarity	NPD1281	Approved
0.6849	Remote Similarity	NPD2798	Approved
0.6849	Remote Similarity	NPD1019	Discontinued
0.6842	Remote Similarity	NPD7240	Approved
0.6842	Remote Similarity	NPD3748	Approved
0.6832	Remote Similarity	NPD6873	Phase 2
0.6832	Remote Similarity	NPD7411	Suspended
0.6831	Remote Similarity	NPD4626	Approved
0.6828	Remote Similarity	NPD3225	Approved
0.6828	Remote Similarity	NPD1876	Approved
0.6815	Remote Similarity	NPD9266	Approved
0.6815	Remote Similarity	NPD74	Approved
0.6813	Remote Similarity	NPD3455	Phase 2
0.6812	Remote Similarity	NPD5283	Phase 1
0.6809	Remote Similarity	NPD1894	Discontinued
0.6805	Remote Similarity	NPD3751	Discontinued
0.6795	Remote Similarity	NPD2309	Approved
0.6792	Remote Similarity	NPD1670	Discontinued
0.6791	Remote Similarity	NPD3134	Approved
0.679	Remote Similarity	NPD6801	Discontinued
0.6783	Remote Similarity	NPD3496	Discontinued
0.678	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2800	Approved
0.6772	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD8313	Approved
0.6763	Remote Similarity	NPD8312	Approved
0.6757	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6355	Discontinued
0.6753	Remote Similarity	NPD1375	Discontinued
0.6753	Remote Similarity	NPD2353	Approved
0.6753	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7440	Discontinued
0.675	Remote Similarity	NPD3687	Approved
0.675	Remote Similarity	NPD3686	Approved
0.6748	Remote Similarity	NPD8455	Phase 2
0.6736	Remote Similarity	NPD422	Phase 1
0.6733	Remote Similarity	NPD6233	Phase 2
0.6732	Remote Similarity	NPD4308	Phase 3
0.6731	Remote Similarity	NPD7003	Approved
0.673	Remote Similarity	NPD6273	Approved
0.6724	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6653	Approved
0.6707	Remote Similarity	NPD5977	Approved
0.6707	Remote Similarity	NPD5978	Approved
0.6706	Remote Similarity	NPD2163	Approved
0.6689	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1613	Approved
0.6688	Remote Similarity	NPD2796	Approved
0.6688	Remote Similarity	NPD3887	Approved
0.6687	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5710	Approved
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD5711	Approved
0.6667	Remote Similarity	NPD969	Suspended
0.6648	Remote Similarity	NPD8434	Phase 2
0.6646	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6002	Phase 3

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