NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.07
Volume:	259.083
LogP:	2.274
LogD:	2.206
LogS:	-1.798
# Rotatable Bonds:	2
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	2.498
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.772
MDCK Permeability:	1.12803454612731e-05
Pgp-inhibitor:	0.063
Pgp-substrate:	0.056
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	96.99071502685547%
Volume Distribution (VD):	0.504
Pgp-substrate:	2.6257872581481934%

ADMET: Metabolism

CYP1A2-inhibitor:	0.794
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.365
CYP2C9-substrate:	0.672
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.727
CYP3A4-inhibitor:	0.537
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	16.85
Half-life (T1/2):	0.932

ADMET: Toxicity

hERG Blockers:	0.143
Human Hepatotoxicity (H-HT):	0.611
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.195
Rat Oral Acute Toxicity:	0.206
Maximum Recommended Daily Dose:	0.827
Skin Sensitization:	0.974
Carcinogencity:	0.096
Eye Corrosion:	0.025
Eye Irritation:	0.928
Respiratory Toxicity:	0.238

Download Data

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

Natural Product: NPC114392

Natural Product ID:	NPC114392
*Common Name:**	(E)-5-(3,5-Dihydroxystyryl)Benzene-1,2,3-Triol
IUPAC Name:	5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2,3-triol
Synonyms:
Standard InCHIKey:	PBRNOKNVNSKDQZ-OWOJBTEDSA-N
Standard InCHI:	InChI=1S/C14H12O5/c15-10-3-8(4-11(16)7-10)1-2-9-5-12(17)14(19)13(18)6-9/h1-7,15-19H/b2-1+
SMILES:	Oc1cc(/C=C/c2cc(O)c(c(c2)O)O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2260735
PubChem CID:	9859982
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO11809	Eleutherococcus sessiliflorus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18961	Azotobacter agilis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6294	Trinia scabra	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11809	Eleutherococcus sessiliflorus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5100	Fritillaria persica	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7749	Coprosma lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9149	Phalaenopsis cornu-cervi	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4110	Lentzea albida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23933	Gymnosporia diversifolia	Species	Celastraceae	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	1
Others	6

Activity Type	# Activity
Individual Protein	3
NON-MOLECULAR	1
Others	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	FC	=	0.4	n.a.	PMID[486407]
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	FC	=	0.3	n.a.	PMID[486407]
NPT496	Individual Protein	Alpha-L-fucosidase 1	Bos taurus	Inhibition	<	50.0	%	PMID[486408]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TIME	=	48.1	hr	PMID[486406]
NPT1	Others	Radical scavenging activity		Inhibition	=	92.9	%	PMID[486406]
NPT2	Others	Unspecified		IC50	=	31050.0	nM	PMID[486408]
NPT24816	SINGLE PROTEIN	Alpha-mannosidase	Canavalia ensiformis	Inhibition	<	50.0	%	PMID[486408]

☑ 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 NPC114392 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	430
0.1-0.2	2173
0.2-0.3	8679
0.3-0.4	11420
0.4-0.5	4585
0.5-0.6	7180
0.6-0.7	6116
0.7-0.8	1815
0.8-0.85	221
0.85-0.9	62
0.9-0.95	10
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC58427
1.0	High Similarity	NPC105727
1.0	High Similarity	NPC34864
0.99	High Similarity	NPC176527
0.9709	High Similarity	NPC268032
0.93	High Similarity	NPC248573
0.93	High Similarity	NPC275053
0.93	High Similarity	NPC161571
0.93	High Similarity	NPC223393
0.9167	High Similarity	NPC472893
0.9126	High Similarity	NPC292452
0.91	High Similarity	NPC291789
0.9091	High Similarity	NPC144343
0.9029	High Similarity	NPC30506
0.9029	High Similarity	NPC471511
0.9009	High Similarity	NPC217174
0.9009	High Similarity	NPC226629
0.9	High Similarity	NPC277588
0.8929	High Similarity	NPC247364
0.8929	High Similarity	NPC61516
0.8929	High Similarity	NPC472071
0.8929	High Similarity	NPC10932
0.8929	High Similarity	NPC232084
0.885	High Similarity	NPC24125
0.8839	High Similarity	NPC191866
0.8835	High Similarity	NPC143659
0.8835	High Similarity	NPC100340
0.8772	High Similarity	NPC237667
0.8762	High Similarity	NPC239291
0.8725	High Similarity	NPC109955
0.8713	High Similarity	NPC107522
0.8696	High Similarity	NPC262253
0.8696	High Similarity	NPC71579
0.8696	High Similarity	NPC473411
0.8679	High Similarity	NPC118286
0.8679	High Similarity	NPC109691
0.8679	High Similarity	NPC302681
0.8679	High Similarity	NPC470700
0.8679	High Similarity	NPC39664
0.8679	High Similarity	NPC39097
0.8667	High Similarity	NPC241891
0.8667	High Similarity	NPC12278
0.8667	High Similarity	NPC102216
0.8641	High Similarity	NPC131587
0.8636	High Similarity	NPC471485
0.8624	High Similarity	NPC179002
0.8624	High Similarity	NPC187583
0.8624	High Similarity	NPC257430
0.8621	High Similarity	NPC197757
0.8621	High Similarity	NPC228922
0.8621	High Similarity	NPC84086
0.8621	High Similarity	NPC53567
0.8621	High Similarity	NPC136319
0.8611	High Similarity	NPC202647
0.8611	High Similarity	NPC228343
0.8611	High Similarity	NPC254833
0.8609	High Similarity	NPC145780
0.8609	High Similarity	NPC39029
0.8598	High Similarity	NPC54844
0.8596	High Similarity	NPC474565
0.8585	High Similarity	NPC246056
0.8585	High Similarity	NPC134829
0.8559	High Similarity	NPC120280
0.8545	High Similarity	NPC43525
0.8534	High Similarity	NPC41562
0.8532	High Similarity	NPC174096
0.8532	High Similarity	NPC79793
0.8532	High Similarity	NPC147634
0.8532	High Similarity	NPC226401
0.8532	High Similarity	NPC120982
0.8522	High Similarity	NPC166759
0.8519	High Similarity	NPC233835
0.8515	High Similarity	NPC295295
0.8505	High Similarity	NPC248904
0.8496	Intermediate Similarity	NPC259638
0.8491	Intermediate Similarity	NPC119860
0.8491	Intermediate Similarity	NPC52087
0.8476	Intermediate Similarity	NPC110764
0.8475	Intermediate Similarity	NPC233410
0.8475	Intermediate Similarity	NPC82483
0.8475	Intermediate Similarity	NPC117214
0.8475	Intermediate Similarity	NPC251855
0.8475	Intermediate Similarity	NPC116907
0.8475	Intermediate Similarity	NPC203133
0.8475	Intermediate Similarity	NPC298757
0.8475	Intermediate Similarity	NPC265483
0.8475	Intermediate Similarity	NPC193544
0.8475	Intermediate Similarity	NPC221077
0.8475	Intermediate Similarity	NPC17943
0.8475	Intermediate Similarity	NPC299584
0.8475	Intermediate Similarity	NPC208950
0.8475	Intermediate Similarity	NPC57490
0.8475	Intermediate Similarity	NPC475169
0.8475	Intermediate Similarity	NPC472093
0.8455	Intermediate Similarity	NPC476632
0.8455	Intermediate Similarity	NPC225679
0.8455	Intermediate Similarity	NPC296920
0.8455	Intermediate Similarity	NPC90520
0.8455	Intermediate Similarity	NPC165770
0.8455	Intermediate Similarity	NPC4493
0.8455	Intermediate Similarity	NPC297657
0.844	Intermediate Similarity	NPC62258
0.844	Intermediate Similarity	NPC55617
0.8435	Intermediate Similarity	NPC229401
0.8411	Intermediate Similarity	NPC474839
0.8407	Intermediate Similarity	NPC193067
0.8403	Intermediate Similarity	NPC44748
0.8403	Intermediate Similarity	NPC18924
0.8403	Intermediate Similarity	NPC28730
0.8403	Intermediate Similarity	NPC78974
0.8403	Intermediate Similarity	NPC214406
0.8403	Intermediate Similarity	NPC223136
0.8403	Intermediate Similarity	NPC103823
0.8396	Intermediate Similarity	NPC477801
0.8396	Intermediate Similarity	NPC477802
0.8396	Intermediate Similarity	NPC196479
0.839	Intermediate Similarity	NPC228972
0.839	Intermediate Similarity	NPC5796
0.839	Intermediate Similarity	NPC206487
0.839	Intermediate Similarity	NPC224342
0.839	Intermediate Similarity	NPC122792
0.8381	Intermediate Similarity	NPC10588
0.8381	Intermediate Similarity	NPC166761
0.8378	Intermediate Similarity	NPC280606
0.8378	Intermediate Similarity	NPC51698
0.8378	Intermediate Similarity	NPC166995
0.835	Intermediate Similarity	NPC274678
0.8349	Intermediate Similarity	NPC174981
0.8348	Intermediate Similarity	NPC20674
0.8333	Intermediate Similarity	NPC74817
0.8333	Intermediate Similarity	NPC1786
0.8333	Intermediate Similarity	NPC246620
0.8333	Intermediate Similarity	NPC82679
0.8333	Intermediate Similarity	NPC470699
0.8333	Intermediate Similarity	NPC156539
0.8333	Intermediate Similarity	NPC124452
0.8333	Intermediate Similarity	NPC169474
0.8333	Intermediate Similarity	NPC159968
0.8333	Intermediate Similarity	NPC210355
0.8333	Intermediate Similarity	NPC294902
0.8333	Intermediate Similarity	NPC236791
0.8333	Intermediate Similarity	NPC127587
0.8333	Intermediate Similarity	NPC324112
0.8333	Intermediate Similarity	NPC282000
0.8333	Intermediate Similarity	NPC107672
0.8333	Intermediate Similarity	NPC266555
0.8333	Intermediate Similarity	NPC1075
0.8333	Intermediate Similarity	NPC293054
0.8319	Intermediate Similarity	NPC234400
0.8319	Intermediate Similarity	NPC60885
0.8318	Intermediate Similarity	NPC79672
0.8318	Intermediate Similarity	NPC120719
0.8305	Intermediate Similarity	NPC282496
0.8305	Intermediate Similarity	NPC233526
0.8305	Intermediate Similarity	NPC121115
0.8305	Intermediate Similarity	NPC95168
0.8304	Intermediate Similarity	NPC117846
0.8302	Intermediate Similarity	NPC72947
0.8302	Intermediate Similarity	NPC284011
0.8286	Intermediate Similarity	NPC80027
0.8276	Intermediate Similarity	NPC223451
0.8273	Intermediate Similarity	NPC33728
0.8273	Intermediate Similarity	NPC19808
0.8264	Intermediate Similarity	NPC46274
0.8264	Intermediate Similarity	NPC98631
0.8264	Intermediate Similarity	NPC206615
0.8264	Intermediate Similarity	NPC186843
0.8264	Intermediate Similarity	NPC154866
0.8264	Intermediate Similarity	NPC470213
0.8264	Intermediate Similarity	NPC226331
0.825	Intermediate Similarity	NPC76451
0.825	Intermediate Similarity	NPC181361
0.8246	Intermediate Similarity	NPC203113
0.823	Intermediate Similarity	NPC107240
0.823	Intermediate Similarity	NPC228287
0.823	Intermediate Similarity	NPC180508
0.8224	Intermediate Similarity	NPC71002
0.8224	Intermediate Similarity	NPC242342
0.8224	Intermediate Similarity	NPC313030
0.8224	Intermediate Similarity	NPC94351
0.8224	Intermediate Similarity	NPC249828
0.8224	Intermediate Similarity	NPC146798
0.8224	Intermediate Similarity	NPC222522
0.8224	Intermediate Similarity	NPC53051
0.8224	Intermediate Similarity	NPC85479
0.8224	Intermediate Similarity	NPC24404
0.8224	Intermediate Similarity	NPC106396
0.8224	Intermediate Similarity	NPC168303
0.8224	Intermediate Similarity	NPC302219
0.82	Intermediate Similarity	NPC280254
0.8198	Intermediate Similarity	NPC475018
0.8198	Intermediate Similarity	NPC94045
0.8197	Intermediate Similarity	NPC228769
0.8197	Intermediate Similarity	NPC170844
0.8197	Intermediate Similarity	NPC58164
0.8197	Intermediate Similarity	NPC476968
0.8197	Intermediate Similarity	NPC470633
0.8197	Intermediate Similarity	NPC212015
0.8197	Intermediate Similarity	NPC10225
0.8182	Intermediate Similarity	NPC5447

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 NPC114392 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	1027
0.2-0.3	1863
0.3-0.4	3018
0.4-0.5	1616
0.5-0.6	900
0.6-0.7	283
0.7-0.8	48
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.93	High Similarity	NPD1242	Phase 1
0.8611	High Similarity	NPD3021	Approved
0.8611	High Similarity	NPD3022	Approved
0.8264	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD9094	Approved
0.8197	Intermediate Similarity	NPD3027	Phase 3
0.8182	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8131	Intermediate Similarity	NPD846	Approved
0.8131	Intermediate Similarity	NPD940	Approved
0.8036	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1613	Approved
0.7905	Intermediate Similarity	NPD2933	Approved
0.7905	Intermediate Similarity	NPD2934	Approved
0.783	Intermediate Similarity	NPD2859	Approved
0.783	Intermediate Similarity	NPD2860	Approved
0.7807	Intermediate Similarity	NPD228	Approved
0.7788	Intermediate Similarity	NPD4750	Phase 3
0.7778	Intermediate Similarity	NPD3020	Approved
0.7769	Intermediate Similarity	NPD9269	Phase 2
0.7739	Intermediate Similarity	NPD9379	Approved
0.7739	Intermediate Similarity	NPD9377	Approved
0.7723	Intermediate Similarity	NPD111	Approved
0.7705	Intermediate Similarity	NPD2983	Phase 2
0.7705	Intermediate Similarity	NPD2982	Phase 2
0.7623	Intermediate Similarity	NPD2981	Phase 2
0.76	Intermediate Similarity	NPD9089	Approved
0.7561	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD9381	Approved
0.7521	Intermediate Similarity	NPD9384	Approved
0.75	Intermediate Similarity	NPD9093	Approved
0.75	Intermediate Similarity	NPD1548	Phase 1
0.748	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD3018	Phase 2
0.7438	Intermediate Similarity	NPD9268	Approved
0.7407	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD1610	Phase 2
0.7385	Intermediate Similarity	NPD230	Phase 1
0.736	Intermediate Similarity	NPD5311	Approved
0.736	Intermediate Similarity	NPD5310	Approved
0.7348	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD844	Approved
0.7308	Intermediate Similarity	NPD3059	Approved
0.7308	Intermediate Similarity	NPD3062	Approved
0.7308	Intermediate Similarity	NPD3061	Approved
0.7302	Intermediate Similarity	NPD3053	Approved
0.7302	Intermediate Similarity	NPD3055	Approved
0.7299	Intermediate Similarity	NPD1511	Approved
0.728	Intermediate Similarity	NPD9622	Approved
0.7273	Intermediate Similarity	NPD288	Approved
0.7232	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5283	Phase 1
0.7197	Intermediate Similarity	NPD5314	Approved
0.7194	Intermediate Similarity	NPD1512	Approved
0.7176	Intermediate Similarity	NPD1558	Phase 1
0.7132	Intermediate Similarity	NPD4908	Phase 1
0.7111	Intermediate Similarity	NPD7266	Discontinued
0.7109	Intermediate Similarity	NPD9620	Approved
0.7109	Intermediate Similarity	NPD9621	Approved
0.7109	Intermediate Similarity	NPD9619	Approved
0.7087	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3028	Approved
0.7068	Intermediate Similarity	NPD2568	Approved
0.7031	Intermediate Similarity	NPD3094	Phase 2
0.7029	Intermediate Similarity	NPD302	Approved
0.7029	Intermediate Similarity	NPD6190	Approved
0.7023	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD2342	Discontinued
0.6992	Remote Similarity	NPD5536	Phase 2
0.6984	Remote Similarity	NPD3092	Approved
0.6984	Remote Similarity	NPD422	Phase 1
0.6977	Remote Similarity	NPD257	Approved
0.6977	Remote Similarity	NPD258	Approved
0.6947	Remote Similarity	NPD4625	Phase 3
0.6929	Remote Similarity	NPD4357	Discontinued
0.6923	Remote Similarity	NPD968	Approved
0.6923	Remote Similarity	NPD9569	Approved
0.6903	Remote Similarity	NPD9273	Approved
0.6899	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1934	Approved
0.6894	Remote Similarity	NPD597	Approved
0.6894	Remote Similarity	NPD598	Approved
0.6894	Remote Similarity	NPD601	Approved
0.6891	Remote Similarity	NPD1792	Phase 2
0.6891	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1357	Approved
0.6875	Remote Similarity	NPD1809	Phase 2
0.6875	Remote Similarity	NPD4749	Approved
0.6861	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3540	Phase 1
0.686	Remote Similarity	NPD7635	Approved
0.6853	Remote Similarity	NPD1653	Approved
0.6849	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2801	Approved
0.6847	Remote Similarity	NPD845	Approved
0.6842	Remote Similarity	NPD1136	Approved
0.6842	Remote Similarity	NPD1132	Approved
0.6842	Remote Similarity	NPD1130	Approved
0.6838	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2286	Discontinued
0.6815	Remote Similarity	NPD823	Approved
0.6815	Remote Similarity	NPD817	Approved
0.681	Remote Similarity	NPD9500	Approved
0.6803	Remote Similarity	NPD2229	Approved
0.6803	Remote Similarity	NPD2228	Approved
0.6803	Remote Similarity	NPD2234	Approved
0.68	Remote Similarity	NPD9087	Approved
0.68	Remote Similarity	NPD3091	Approved
0.6794	Remote Similarity	NPD9494	Approved
0.6791	Remote Similarity	NPD1555	Discontinued
0.6788	Remote Similarity	NPD3539	Phase 1
0.6788	Remote Similarity	NPD9570	Approved
0.6788	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD9296	Approved
0.678	Remote Similarity	NPD1445	Approved
0.678	Remote Similarity	NPD1444	Approved
0.6757	Remote Similarity	NPD3882	Suspended
0.6752	Remote Similarity	NPD9610	Approved
0.6752	Remote Similarity	NPD9608	Approved
0.6748	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4093	Discontinued
0.6744	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1201	Approved
0.6716	Remote Similarity	NPD259	Phase 1
0.6715	Remote Similarity	NPD1510	Phase 2
0.6699	Remote Similarity	NPD9088	Approved
0.6693	Remote Similarity	NPD2932	Approved
0.6693	Remote Similarity	NPD4059	Approved
0.6693	Remote Similarity	NPD3019	Approved
0.6693	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD9537	Phase 1
0.6692	Remote Similarity	NPD9536	Phase 1
0.6667	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD2861	Phase 2
0.6667	Remote Similarity	NPD1240	Approved
0.6644	Remote Similarity	NPD4678	Approved
0.6644	Remote Similarity	NPD4675	Approved
0.6644	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3060	Approved
0.6642	Remote Similarity	NPD3145	Approved
0.6642	Remote Similarity	NPD3144	Approved
0.6642	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD1470	Approved
0.6618	Remote Similarity	NPD275	Approved
0.6618	Remote Similarity	NPD555	Phase 2
0.6618	Remote Similarity	NPD274	Approved
0.6593	Remote Similarity	NPD2674	Phase 3
0.6593	Remote Similarity	NPD6405	Approved
0.6593	Remote Similarity	NPD6407	Approved
0.6591	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD858	Approved
0.6591	Remote Similarity	NPD602	Approved
0.6591	Remote Similarity	NPD599	Approved
0.6591	Remote Similarity	NPD859	Approved
0.6589	Remote Similarity	NPD1091	Approved
0.6583	Remote Similarity	NPD290	Approved
0.6569	Remote Similarity	NPD1607	Approved
0.6562	Remote Similarity	NPD1751	Approved
0.6562	Remote Similarity	NPD3095	Discontinued
0.656	Remote Similarity	NPD6671	Approved
0.6556	Remote Similarity	NPD6234	Discontinued
0.6549	Remote Similarity	NPD2219	Phase 1
0.6549	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD4060	Phase 1
0.6538	Remote Similarity	NPD2562	Approved
0.6538	Remote Similarity	NPD2561	Approved
0.6529	Remote Similarity	NPD2684	Approved
0.6519	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD1164	Approved
0.651	Remote Similarity	NPD1465	Phase 2
0.6503	Remote Similarity	NPD7124	Phase 2
0.65	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4659	Approved
0.648	Remote Similarity	NPD9614	Approved
0.648	Remote Similarity	NPD9618	Approved
0.648	Remote Similarity	NPD497	Approved
0.6479	Remote Similarity	NPD8166	Discontinued
0.6479	Remote Similarity	NPD3750	Approved
0.6466	Remote Similarity	NPD6584	Phase 3
0.6463	Remote Similarity	NPD4005	Discontinued
0.6462	Remote Similarity	NPD3705	Approved
0.6462	Remote Similarity	NPD1535	Discovery
0.6458	Remote Similarity	NPD7390	Discontinued
0.6457	Remote Similarity	NPD16	Approved
0.6457	Remote Similarity	NPD317	Approved
0.6457	Remote Similarity	NPD856	Approved
0.6457	Remote Similarity	NPD318	Approved
0.6454	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD1549	Phase 2
0.6452	Remote Similarity	NPD7843	Approved
0.6452	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6166	Phase 2
0.6452	Remote Similarity	NPD6168	Clinical (unspecified phase)

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