NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	154.03
Volume:	145.687
LogP:	1.203
LogD:	1.005
LogS:	-1.801
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	2.641
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.891
MDCK Permeability:	4.789179911313113e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	73.89139556884766%
Volume Distribution (VD):	0.803
Pgp-substrate:	21.804584503173828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.754
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.829
CYP2D6-inhibitor:	0.143
CYP2D6-substrate:	0.3
CYP3A4-inhibitor:	0.378
CYP3A4-substrate:	0.08

ADMET: Excretion

Clearance (CL):	13.979
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.554
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.558
Skin Sensitization:	0.924
Carcinogencity:	0.048
Eye Corrosion:	0.978
Eye Irritation:	0.95
Respiratory Toxicity:	0.904

Download Data

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

Natural Product: NPC230349

Natural Product ID:	NPC230349
*Common Name:**	Phloroglucinaldehyde
IUPAC Name:	2,4,6-trihydroxybenzaldehyde
Synonyms:
Standard InCHIKey:	BTQAJGSMXCDDAJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H6O4/c8-3-5-6(10)1-4(9)2-7(5)11/h1-3,9-11H
SMILES:	c1c(cc(c(C=O)c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2403487
PubChem CID:	68099
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001310] Benzenetriols and derivatives [CHEMONTID:0000382] Phloroglucinols and derivatives [CHEMONTID:0002519] Acylphloroglucinols 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
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16748484]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20597533]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23656415]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25650289]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Bulb	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23230	Allium cepa	Species	Amaryllidaceae	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	2
Others	6

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	367.9	mg/dl	PMID[469454]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	96.5	mg/dl	PMID[469454]
NPT1	Others	Radical scavenging activity		IC50	=	71400.0	nM	PMID[469454]
NPT2	Others	Unspecified		IC50	=	4600.0	nM	PMID[469454]
NPT1	Others	Radical scavenging activity		Activity	=	91.2	%	PMID[469456]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	42.0	%	PMID[469456]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	36.0	%	PMID[469456]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	TIME	=	3.0	hr	PMID[469457]

☑ 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 NPC230349 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	393
0.1-0.2	2138
0.2-0.3	5793
0.3-0.4	13201
0.4-0.5	4801
0.5-0.6	6394
0.6-0.7	6837
0.7-0.8	2794
0.8-0.85	253
0.85-0.9	85
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.973	High Similarity	NPC283844
0.9211	High Similarity	NPC40649
0.9211	High Similarity	NPC209486
0.9211	High Similarity	NPC241089
0.9052	High Similarity	NPC294037
0.8974	High Similarity	NPC146642
0.8974	High Similarity	NPC149246
0.8966	High Similarity	NPC161617
0.8938	High Similarity	NPC223004
0.8898	High Similarity	NPC242895
0.8898	High Similarity	NPC45438
0.8898	High Similarity	NPC143427
0.8898	High Similarity	NPC115159
0.8898	High Similarity	NPC267552
0.8898	High Similarity	NPC19174
0.8898	High Similarity	NPC224273
0.8898	High Similarity	NPC73532
0.8898	High Similarity	NPC215392
0.8889	High Similarity	NPC294964
0.8824	High Similarity	NPC32032
0.8824	High Similarity	NPC133909
0.8824	High Similarity	NPC91105
0.8814	High Similarity	NPC297186
0.878	High Similarity	NPC78662
0.878	High Similarity	NPC8005
0.878	High Similarity	NPC476119
0.875	High Similarity	NPC65761
0.875	High Similarity	NPC472029
0.8739	High Similarity	NPC156139
0.8739	High Similarity	NPC303264
0.8739	High Similarity	NPC226275
0.871	High Similarity	NPC62219
0.8696	High Similarity	NPC118288
0.8696	High Similarity	NPC276111
0.8689	High Similarity	NPC95309
0.8678	High Similarity	NPC13238
0.8667	High Similarity	NPC309765
0.8644	High Similarity	NPC158222
0.864	High Similarity	NPC275504
0.8629	High Similarity	NPC120488
0.8629	High Similarity	NPC102829
0.8618	High Similarity	NPC305518
0.8618	High Similarity	NPC128428
0.8607	High Similarity	NPC262671
0.8607	High Similarity	NPC10926
0.8607	High Similarity	NPC475733
0.8607	High Similarity	NPC201728
0.8583	High Similarity	NPC474519
0.8583	High Similarity	NPC196976
0.8583	High Similarity	NPC303737
0.8571	High Similarity	NPC159525
0.856	High Similarity	NPC147757
0.856	High Similarity	NPC185497
0.8559	High Similarity	NPC219913
0.8548	High Similarity	NPC293453
0.8537	High Similarity	NPC8745
0.8537	High Similarity	NPC267846
0.8516	High Similarity	NPC278375
0.8512	High Similarity	NPC218333
0.8492	Intermediate Similarity	NPC198249
0.8492	Intermediate Similarity	NPC475042
0.848	Intermediate Similarity	NPC60558
0.848	Intermediate Similarity	NPC69235
0.848	Intermediate Similarity	NPC212379
0.8475	Intermediate Similarity	NPC121259
0.8468	Intermediate Similarity	NPC103356
0.8468	Intermediate Similarity	NPC30501
0.8468	Intermediate Similarity	NPC266689
0.8468	Intermediate Similarity	NPC98254
0.8468	Intermediate Similarity	NPC100067
0.8468	Intermediate Similarity	NPC169250
0.8468	Intermediate Similarity	NPC162612
0.8468	Intermediate Similarity	NPC190043
0.8468	Intermediate Similarity	NPC72158
0.8468	Intermediate Similarity	NPC23126
0.8468	Intermediate Similarity	NPC116513
0.8468	Intermediate Similarity	NPC105157
0.8455	Intermediate Similarity	NPC477454
0.8443	Intermediate Similarity	NPC306288
0.8425	Intermediate Similarity	NPC65060
0.8425	Intermediate Similarity	NPC478190
0.8413	Intermediate Similarity	NPC42292
0.8413	Intermediate Similarity	NPC307732
0.84	Intermediate Similarity	NPC41263
0.84	Intermediate Similarity	NPC473017
0.84	Intermediate Similarity	NPC21305
0.84	Intermediate Similarity	NPC186098
0.84	Intermediate Similarity	NPC179898
0.84	Intermediate Similarity	NPC221777
0.84	Intermediate Similarity	NPC80694
0.8387	Intermediate Similarity	NPC62952
0.8387	Intermediate Similarity	NPC473691
0.8385	Intermediate Similarity	NPC222633
0.8374	Intermediate Similarity	NPC255073
0.8359	Intermediate Similarity	NPC139074
0.8359	Intermediate Similarity	NPC153783
0.8359	Intermediate Similarity	NPC203817
0.8359	Intermediate Similarity	NPC213485
0.8359	Intermediate Similarity	NPC40524
0.8346	Intermediate Similarity	NPC219892
0.8346	Intermediate Similarity	NPC189823
0.8333	Intermediate Similarity	NPC474998
0.8333	Intermediate Similarity	NPC188814
0.8333	Intermediate Similarity	NPC195262
0.8333	Intermediate Similarity	NPC100551
0.8333	Intermediate Similarity	NPC230818
0.832	Intermediate Similarity	NPC214620
0.8295	Intermediate Similarity	NPC223457
0.8281	Intermediate Similarity	NPC262359
0.8281	Intermediate Similarity	NPC475589
0.8281	Intermediate Similarity	NPC31872
0.8281	Intermediate Similarity	NPC473584
0.8276	Intermediate Similarity	NPC114682
0.8268	Intermediate Similarity	NPC84772
0.8268	Intermediate Similarity	NPC233056
0.8268	Intermediate Similarity	NPC26697
0.8268	Intermediate Similarity	NPC17840
0.8268	Intermediate Similarity	NPC247477
0.8258	Intermediate Similarity	NPC162939
0.825	Intermediate Similarity	NPC184527
0.8246	Intermediate Similarity	NPC29883
0.8231	Intermediate Similarity	NPC130899
0.8231	Intermediate Similarity	NPC236974
0.8231	Intermediate Similarity	NPC283590
0.8231	Intermediate Similarity	NPC164136
0.8231	Intermediate Similarity	NPC470210
0.8231	Intermediate Similarity	NPC144027
0.8231	Intermediate Similarity	NPC70859
0.8231	Intermediate Similarity	NPC61153
0.822	Intermediate Similarity	NPC163154
0.8217	Intermediate Similarity	NPC205468
0.8217	Intermediate Similarity	NPC87231
0.8217	Intermediate Similarity	NPC212631
0.8217	Intermediate Similarity	NPC103105
0.8217	Intermediate Similarity	NPC129132
0.8217	Intermediate Similarity	NPC257756
0.8217	Intermediate Similarity	NPC25937
0.8203	Intermediate Similarity	NPC324482
0.8203	Intermediate Similarity	NPC5515
0.8203	Intermediate Similarity	NPC469526
0.8203	Intermediate Similarity	NPC270369
0.8203	Intermediate Similarity	NPC34070
0.8197	Intermediate Similarity	NPC248363
0.8195	Intermediate Similarity	NPC99441
0.8189	Intermediate Similarity	NPC92624
0.8168	Intermediate Similarity	NPC234560
0.8168	Intermediate Similarity	NPC39426
0.8168	Intermediate Similarity	NPC84699
0.8168	Intermediate Similarity	NPC235115
0.8168	Intermediate Similarity	NPC60667
0.8158	Intermediate Similarity	NPC184658
0.8154	Intermediate Similarity	NPC192304
0.8154	Intermediate Similarity	NPC188646
0.8154	Intermediate Similarity	NPC139813
0.8154	Intermediate Similarity	NPC312318
0.8154	Intermediate Similarity	NPC28753
0.8154	Intermediate Similarity	NPC144051
0.8154	Intermediate Similarity	NPC175098
0.8154	Intermediate Similarity	NPC472365
0.8154	Intermediate Similarity	NPC337373
0.8154	Intermediate Similarity	NPC82225
0.8154	Intermediate Similarity	NPC242294
0.8154	Intermediate Similarity	NPC263670
0.8154	Intermediate Similarity	NPC56031
0.8154	Intermediate Similarity	NPC204960
0.8154	Intermediate Similarity	NPC18877
0.8154	Intermediate Similarity	NPC20560
0.8154	Intermediate Similarity	NPC294593
0.8154	Intermediate Similarity	NPC159623
0.814	Intermediate Similarity	NPC308037
0.814	Intermediate Similarity	NPC135801
0.814	Intermediate Similarity	NPC27490
0.814	Intermediate Similarity	NPC313618
0.814	Intermediate Similarity	NPC64359
0.814	Intermediate Similarity	NPC175738
0.8136	Intermediate Similarity	NPC98543
0.8134	Intermediate Similarity	NPC37530
0.8125	Intermediate Similarity	NPC259942
0.812	Intermediate Similarity	NPC471620
0.811	Intermediate Similarity	NPC470981
0.8106	Intermediate Similarity	NPC187826
0.8106	Intermediate Similarity	NPC240147
0.8106	Intermediate Similarity	NPC193792
0.8106	Intermediate Similarity	NPC121243
0.8106	Intermediate Similarity	NPC470397
0.8106	Intermediate Similarity	NPC70380
0.8106	Intermediate Similarity	NPC470398
0.8106	Intermediate Similarity	NPC87545
0.8106	Intermediate Similarity	NPC156910
0.8106	Intermediate Similarity	NPC178467
0.8106	Intermediate Similarity	NPC235428
0.8106	Intermediate Similarity	NPC71256
0.8106	Intermediate Similarity	NPC149372
0.8106	Intermediate Similarity	NPC65837
0.8106	Intermediate Similarity	NPC474771
0.8106	Intermediate Similarity	NPC474849
0.8106	Intermediate Similarity	NPC135837
0.8106	Intermediate Similarity	NPC170742
0.8095	Intermediate Similarity	NPC328983
0.8092	Intermediate Similarity	NPC474076

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 NPC230349 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	1005
0.2-0.3	1940
0.3-0.4	3015
0.4-0.5	1712
0.5-0.6	831
0.6-0.7	186
0.7-0.8	55
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD9266	Approved
0.8333	Intermediate Similarity	NPD74	Approved
0.8246	Intermediate Similarity	NPD9267	Approved
0.8246	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD9263	Approved
0.8246	Intermediate Similarity	NPD9264	Approved
0.8168	Intermediate Similarity	NPD1510	Phase 2
0.814	Intermediate Similarity	NPD1240	Approved
0.814	Intermediate Similarity	NPD943	Approved
0.8065	Intermediate Similarity	NPD9269	Phase 2
0.8045	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD9268	Approved
0.8015	Intermediate Similarity	NPD1607	Approved
0.7985	Intermediate Similarity	NPD1549	Phase 2
0.7934	Intermediate Similarity	NPD9493	Approved
0.7917	Intermediate Similarity	NPD9281	Approved
0.7895	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD9261	Approved
0.7895	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1551	Phase 2
0.7805	Intermediate Similarity	NPD9545	Approved
0.7669	Intermediate Similarity	NPD230	Phase 1
0.7518	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD940	Approved
0.75	Intermediate Similarity	NPD846	Approved
0.7462	Intermediate Similarity	NPD1164	Approved
0.7447	Intermediate Similarity	NPD7390	Discontinued
0.7447	Intermediate Similarity	NPD1511	Approved
0.7422	Intermediate Similarity	NPD1201	Approved
0.7379	Intermediate Similarity	NPD4380	Phase 2
0.7364	Intermediate Similarity	NPD9717	Approved
0.7357	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6651	Approved
0.7343	Intermediate Similarity	NPD1512	Approved
0.7328	Intermediate Similarity	NPD1203	Approved
0.7328	Intermediate Similarity	NPD1470	Approved
0.7324	Intermediate Similarity	NPD6799	Approved
0.7323	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD2796	Approved
0.7279	Intermediate Similarity	NPD1934	Approved
0.7273	Intermediate Similarity	NPD2534	Approved
0.7273	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2533	Approved
0.7273	Intermediate Similarity	NPD2532	Approved
0.7259	Intermediate Similarity	NPD520	Approved
0.7254	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7411	Suspended
0.7185	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2800	Approved
0.7163	Intermediate Similarity	NPD2654	Approved
0.7153	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3882	Suspended
0.7119	Intermediate Similarity	NPD1242	Phase 1
0.7114	Intermediate Similarity	NPD2801	Approved
0.709	Intermediate Similarity	NPD9494	Approved
0.7086	Intermediate Similarity	NPD7075	Discontinued
0.7086	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5408	Approved
0.7071	Intermediate Similarity	NPD5405	Approved
0.7071	Intermediate Similarity	NPD5406	Approved
0.7071	Intermediate Similarity	NPD5404	Approved
0.7071	Intermediate Similarity	NPD2935	Discontinued
0.7055	Intermediate Similarity	NPD920	Approved
0.7027	Intermediate Similarity	NPD6599	Discontinued
0.7	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7819	Suspended
0.6993	Remote Similarity	NPD3750	Approved
0.6934	Remote Similarity	NPD411	Approved
0.6933	Remote Similarity	NPD6801	Discontinued
0.693	Remote Similarity	NPD9258	Approved
0.693	Remote Similarity	NPD9256	Approved
0.6923	Remote Similarity	NPD1243	Approved
0.6918	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7768	Phase 2
0.6894	Remote Similarity	NPD422	Phase 1
0.6889	Remote Similarity	NPD1019	Discontinued
0.6881	Remote Similarity	NPD9093	Approved
0.6863	Remote Similarity	NPD3749	Approved
0.6846	Remote Similarity	NPD1548	Phase 1
0.6842	Remote Similarity	NPD3817	Phase 2
0.6839	Remote Similarity	NPD6959	Discontinued
0.6824	Remote Similarity	NPD5403	Approved
0.6818	Remote Similarity	NPD9089	Approved
0.6815	Remote Similarity	NPD6166	Phase 2
0.6815	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5401	Approved
0.68	Remote Similarity	NPD4750	Phase 3
0.6797	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6232	Discontinued
0.6788	Remote Similarity	NPD6832	Phase 2
0.6786	Remote Similarity	NPD447	Suspended
0.6786	Remote Similarity	NPD111	Approved
0.6783	Remote Similarity	NPD2344	Approved
0.6767	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3818	Discontinued
0.6718	Remote Similarity	NPD1759	Phase 1
0.671	Remote Similarity	NPD919	Approved
0.6691	Remote Similarity	NPD3764	Approved
0.669	Remote Similarity	NPD9279	Approved
0.6687	Remote Similarity	NPD7054	Approved
0.6687	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9273	Approved
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD1237	Approved
0.6646	Remote Similarity	NPD7074	Phase 3
0.6646	Remote Similarity	NPD7472	Approved
0.6643	Remote Similarity	NPD3748	Approved
0.6642	Remote Similarity	NPD1610	Phase 2
0.6641	Remote Similarity	NPD1758	Phase 1
0.6624	Remote Similarity	NPD1247	Approved
0.6605	Remote Similarity	NPD6797	Phase 2
0.6605	Remote Similarity	NPD5953	Discontinued
0.6599	Remote Similarity	NPD2309	Approved
0.6589	Remote Similarity	NPD1241	Discontinued
0.6584	Remote Similarity	NPD7286	Phase 2
0.6582	Remote Similarity	NPD5711	Approved
0.6582	Remote Similarity	NPD5710	Approved
0.6579	Remote Similarity	NPD9259	Approved
0.6579	Remote Similarity	NPD9257	Approved
0.6571	Remote Similarity	NPD1296	Phase 2
0.6564	Remote Similarity	NPD6559	Discontinued
0.6564	Remote Similarity	NPD7251	Discontinued
0.6558	Remote Similarity	NPD1465	Phase 2
0.6555	Remote Similarity	NPD2934	Approved
0.6555	Remote Similarity	NPD2933	Approved
0.6549	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4628	Phase 3
0.6531	Remote Similarity	NPD1196	Approved
0.6528	Remote Similarity	NPD2799	Discontinued
0.6524	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7808	Phase 3
0.6524	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2798	Approved
0.6516	Remote Similarity	NPD5402	Approved
0.6507	Remote Similarity	NPD9277	Approved
0.6507	Remote Similarity	NPD75	Approved
0.65	Remote Similarity	NPD1809	Phase 2
0.65	Remote Similarity	NPD2859	Approved
0.65	Remote Similarity	NPD2860	Approved
0.6496	Remote Similarity	NPD3225	Approved
0.6489	Remote Similarity	NPD256	Approved
0.6489	Remote Similarity	NPD255	Approved
0.6486	Remote Similarity	NPD6190	Approved
0.6483	Remote Similarity	NPD6100	Approved
0.6483	Remote Similarity	NPD6099	Approved
0.6471	Remote Similarity	NPD3972	Approved
0.6466	Remote Similarity	NPD9094	Approved
0.6463	Remote Similarity	NPD1195	Approved
0.6456	Remote Similarity	NPD5494	Approved
0.6454	Remote Similarity	NPD2313	Discontinued
0.6443	Remote Similarity	NPD3300	Phase 2
0.6442	Remote Similarity	NPD1729	Discontinued
0.6439	Remote Similarity	NPD9568	Approved
0.6438	Remote Similarity	NPD9275	Approved
0.6438	Remote Similarity	NPD9278	Suspended
0.6438	Remote Similarity	NPD9274	Approved
0.6438	Remote Similarity	NPD9276	Approved
0.6434	Remote Similarity	NPD1933	Approved
0.6429	Remote Similarity	NPD4908	Phase 1
0.6419	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD3400	Discontinued
0.6417	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7033	Discontinued
0.6406	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1543	Discontinued
0.6393	Remote Similarity	NPD9495	Approved
0.638	Remote Similarity	NPD6020	Phase 2
0.637	Remote Similarity	NPD9570	Approved
0.6364	Remote Similarity	NPD844	Approved
0.6364	Remote Similarity	NPD468	Phase 1
0.635	Remote Similarity	NPD1481	Phase 2
0.6341	Remote Similarity	NPD3020	Approved
0.6338	Remote Similarity	NPD3268	Approved
0.6338	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1202	Approved
0.6333	Remote Similarity	NPD845	Approved
0.6331	Remote Similarity	NPD2797	Approved
0.6311	Remote Similarity	NPD288	Approved
0.6308	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD4308	Phase 3
0.629	Remote Similarity	NPD289	Clinical (unspecified phase)
0.628	Remote Similarity	NPD5844	Phase 1
0.6277	Remote Similarity	NPD1535	Discovery
0.6275	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD6104	Discontinued
0.625	Remote Similarity	NPD1613	Approved
0.625	Remote Similarity	NPD2932	Approved
0.625	Remote Similarity	NPD1778	Approved
0.625	Remote Similarity	NPD3019	Approved
0.625	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD1530	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