NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	225.06
Volume:	211.561
LogP:	2.167
LogD:	1.7
LogS:	-3.021
# Rotatable Bonds:	4
TPSA:	79.87
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	2.218
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.214
MDCK Permeability:	2.281974047946278e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.552
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.183
30% Bioavailability (F30%):	0.881

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.549
Plasma Protein Binding (PPB):	96.69476318359375%
Volume Distribution (VD):	1.801
Pgp-substrate:	4.170656681060791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.873
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.199
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.793
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.826
CYP3A4-inhibitor:	0.179
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	8.698
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.16
Rat Oral Acute Toxicity:	0.56
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.267
Carcinogencity:	0.437
Eye Corrosion:	0.023
Eye Irritation:	0.88
Respiratory Toxicity:	0.381

Download Data

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

Natural Product: NPC174754

Natural Product ID:	NPC174754
*Common Name:**	3-Hydroxy-4-Methoxybenzaldehyde Thiosemicarbazone
IUPAC Name:	[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea
Synonyms:
Standard InCHIKey:	ARINKVDYBABITQ-VZUCSPMQSA-N
Standard InCHI:	InChI=1S/C9H11N3O2S/c1-14-8-3-2-6(4-7(8)13)5-11-12-9(10)15/h2-5,13H,1H3,(H3,10,12,15)/b11-5+
SMILES:	COc1ccc(cc1O)/C=N/NC(=N)S
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL242103
PubChem CID:	6870649
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	Flowers	Muyang, China	n.a.	PMID[24621197]
NPO18343	Lavandula pedunculata	Species	Lamiaceae	Eukaryota	Flowers	Yili, China	n.a.	PMID[24621197]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18343	Lavandula pedunculata	Species	Lamiaceae	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
NPO18093	NPC174754	n.a.	Flowers	1085.6 ± 13.4	n.a.	n.a.	µg/g of DW	PMID[24621197]
NPO18343	NPC174754	n.a.	Flowers	1827.6 ± 46.8	n.a.	n.a.	µg/g of DW	PMID[24621197]

☑ 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	5
Others	6

Activity Type	# Activity
Cell Line	4
CELL-LINE	1
Individual Protein	3
Others	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	4880.0	nM	PMID[507593]
NPT146	Cell Line	SK-OV-3	Homo sapiens	Inhibition	<	0.0	%	PMID[507594]
NPT181	Cell Line	Bel-7402	Homo sapiens	Inhibition	=	10.5	%	PMID[507594]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	47.6	%	PMID[507594]
NPT492	Cell Line	Caco-2	Homo sapiens	Inhibition	=	11.9	%	PMID[507594]
NPT2562	Individual Protein	Poly [ADP-ribose] polymerase-1	Homo sapiens	Inhibition	=	28.1	%	PMID[507594]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	IC50	>	10000.0	nM	PMID[507590]
NPT2	Others	Unspecified		IC50	=	260.0	nM	PMID[507591]
NPT2	Others	Unspecified		IC50	=	3890451449942804.5	nM	PMID[507591]
NPT26648	SINGLE PROTEIN	Snake venom metalloproteinase neuwiedase	Bothrops pauloensis	IC50	=	3410000.0	nM	PMID[507592]
NPT21742	CELL-LINE	L02	Homo sapiens	Inhibition	=	5.54	%	PMID[507594]

☑ 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 NPC174754 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	254
0.1-0.2	3540
0.2-0.3	13463
0.3-0.4	5586
0.4-0.5	9213
0.5-0.6	8533
0.6-0.7	1941
0.7-0.8	165
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.812	Intermediate Similarity	NPC183262
0.7971	Intermediate Similarity	NPC186898
0.7941	Intermediate Similarity	NPC13020
0.7941	Intermediate Similarity	NPC140359
0.7891	Intermediate Similarity	NPC246358
0.7891	Intermediate Similarity	NPC233731
0.7891	Intermediate Similarity	NPC36108
0.7891	Intermediate Similarity	NPC7097
0.7842	Intermediate Similarity	NPC153990
0.7786	Intermediate Similarity	NPC155838
0.7769	Intermediate Similarity	NPC257124
0.7769	Intermediate Similarity	NPC8547
0.7769	Intermediate Similarity	NPC78918
0.7769	Intermediate Similarity	NPC173746
0.7769	Intermediate Similarity	NPC156840
0.7769	Intermediate Similarity	NPC139617
0.773	Intermediate Similarity	NPC35961
0.773	Intermediate Similarity	NPC195749
0.773	Intermediate Similarity	NPC52029
0.7676	Intermediate Similarity	NPC308885
0.7676	Intermediate Similarity	NPC114102
0.7676	Intermediate Similarity	NPC255550
0.7622	Intermediate Similarity	NPC214869
0.7622	Intermediate Similarity	NPC93882
0.7622	Intermediate Similarity	NPC130595
0.7589	Intermediate Similarity	NPC251571
0.7569	Intermediate Similarity	NPC6854
0.7569	Intermediate Similarity	NPC285078
0.7569	Intermediate Similarity	NPC313737
0.7552	Intermediate Similarity	NPC329595
0.7552	Intermediate Similarity	NPC326599
0.7538	Intermediate Similarity	NPC309982
0.7517	Intermediate Similarity	NPC218530
0.75	Intermediate Similarity	NPC300955
0.75	Intermediate Similarity	NPC195873
0.7481	Intermediate Similarity	NPC221049
0.7462	Intermediate Similarity	NPC227894
0.7447	Intermediate Similarity	NPC71105
0.7447	Intermediate Similarity	NPC207541
0.7447	Intermediate Similarity	NPC170583
0.7447	Intermediate Similarity	NPC152186
0.7447	Intermediate Similarity	NPC246133
0.7447	Intermediate Similarity	NPC182147
0.7426	Intermediate Similarity	NPC39793
0.7426	Intermediate Similarity	NPC259638
0.7426	Intermediate Similarity	NPC120075
0.7426	Intermediate Similarity	NPC164386
0.7426	Intermediate Similarity	NPC293619
0.74	Intermediate Similarity	NPC222039
0.74	Intermediate Similarity	NPC100478
0.7394	Intermediate Similarity	NPC301713
0.7394	Intermediate Similarity	NPC251466
0.7394	Intermediate Similarity	NPC156944
0.7383	Intermediate Similarity	NPC477838
0.7383	Intermediate Similarity	NPC477837
0.7372	Intermediate Similarity	NPC70744
0.7372	Intermediate Similarity	NPC255675
0.7372	Intermediate Similarity	NPC107588
0.7372	Intermediate Similarity	NPC164706
0.7372	Intermediate Similarity	NPC272471
0.7372	Intermediate Similarity	NPC137537
0.7372	Intermediate Similarity	NPC470626
0.7365	Intermediate Similarity	NPC14600
0.7365	Intermediate Similarity	NPC312770
0.7365	Intermediate Similarity	NPC160607
0.7365	Intermediate Similarity	NPC204848
0.7365	Intermediate Similarity	NPC41473
0.7353	Intermediate Similarity	NPC193067
0.7348	Intermediate Similarity	NPC71266
0.7344	Intermediate Similarity	NPC12714
0.7344	Intermediate Similarity	NPC310905
0.7343	Intermediate Similarity	NPC291449
0.7343	Intermediate Similarity	NPC99798
0.7343	Intermediate Similarity	NPC41331
0.7343	Intermediate Similarity	NPC157740
0.7343	Intermediate Similarity	NPC191302
0.7319	Intermediate Similarity	NPC20674
0.7319	Intermediate Similarity	NPC24474
0.7319	Intermediate Similarity	NPC310338
0.7319	Intermediate Similarity	NPC311595
0.7319	Intermediate Similarity	NPC281298
0.7319	Intermediate Similarity	NPC299406
0.7319	Intermediate Similarity	NPC320987
0.7319	Intermediate Similarity	NPC181969
0.7315	Intermediate Similarity	NPC299583
0.7315	Intermediate Similarity	NPC296898
0.7293	Intermediate Similarity	NPC137685
0.7292	Intermediate Similarity	NPC147247
0.7292	Intermediate Similarity	NPC246974
0.7266	Intermediate Similarity	NPC202474
0.7266	Intermediate Similarity	NPC117780
0.7266	Intermediate Similarity	NPC148615
0.7266	Intermediate Similarity	NPC229401
0.7266	Intermediate Similarity	NPC95614
0.7266	Intermediate Similarity	NPC61516
0.7266	Intermediate Similarity	NPC2058
0.7266	Intermediate Similarity	NPC35071
0.7266	Intermediate Similarity	NPC10932
0.7266	Intermediate Similarity	NPC247364
0.7266	Intermediate Similarity	NPC232084
0.7266	Intermediate Similarity	NPC165133
0.7266	Intermediate Similarity	NPC227217
0.7266	Intermediate Similarity	NPC177475
0.7266	Intermediate Similarity	NPC242885
0.7266	Intermediate Similarity	NPC232316
0.7266	Intermediate Similarity	NPC56214
0.7255	Intermediate Similarity	NPC5462
0.7239	Intermediate Similarity	NPC55300
0.7231	Intermediate Similarity	NPC292792
0.7214	Intermediate Similarity	NPC158949
0.7214	Intermediate Similarity	NPC14007
0.7214	Intermediate Similarity	NPC207613
0.7214	Intermediate Similarity	NPC189844
0.7214	Intermediate Similarity	NPC109083
0.7214	Intermediate Similarity	NPC204466
0.7214	Intermediate Similarity	NPC224814
0.7214	Intermediate Similarity	NPC269843
0.7214	Intermediate Similarity	NPC83279
0.7214	Intermediate Similarity	NPC60962
0.7192	Intermediate Similarity	NPC476570
0.7185	Intermediate Similarity	NPC165646
0.7174	Intermediate Similarity	NPC86947
0.7172	Intermediate Similarity	NPC469977
0.7163	Intermediate Similarity	NPC262156
0.7163	Intermediate Similarity	NPC343720
0.7163	Intermediate Similarity	NPC201777
0.7163	Intermediate Similarity	NPC470212
0.7163	Intermediate Similarity	NPC177291
0.7163	Intermediate Similarity	NPC473853
0.7163	Intermediate Similarity	NPC160380
0.7163	Intermediate Similarity	NPC194416
0.7163	Intermediate Similarity	NPC184651
0.7163	Intermediate Similarity	NPC312675
0.7163	Intermediate Similarity	NPC70752
0.7163	Intermediate Similarity	NPC38996
0.7163	Intermediate Similarity	NPC324571
0.7163	Intermediate Similarity	NPC470804
0.7163	Intermediate Similarity	NPC113865
0.7163	Intermediate Similarity	NPC54872
0.7163	Intermediate Similarity	NPC476343
0.7133	Intermediate Similarity	NPC254610
0.7123	Intermediate Similarity	NPC470706
0.7122	Intermediate Similarity	NPC212743
0.7113	Intermediate Similarity	NPC41562
0.7113	Intermediate Similarity	NPC286573
0.7113	Intermediate Similarity	NPC71579
0.7113	Intermediate Similarity	NPC473411
0.7113	Intermediate Similarity	NPC298486
0.7113	Intermediate Similarity	NPC262253
0.7113	Intermediate Similarity	NPC114298
0.7113	Intermediate Similarity	NPC209567
0.7113	Intermediate Similarity	NPC85488
0.7111	Intermediate Similarity	NPC166837
0.7105	Intermediate Similarity	NPC66518
0.7099	Intermediate Similarity	NPC12987
0.7099	Intermediate Similarity	NPC474603
0.708	Intermediate Similarity	NPC142599
0.708	Intermediate Similarity	NPC294941
0.7071	Intermediate Similarity	NPC226629
0.7071	Intermediate Similarity	NPC135961
0.7071	Intermediate Similarity	NPC43275
0.7068	Intermediate Similarity	NPC258171
0.7063	Intermediate Similarity	NPC257976
0.7063	Intermediate Similarity	NPC160900
0.7063	Intermediate Similarity	NPC228922
0.7063	Intermediate Similarity	NPC471693
0.7063	Intermediate Similarity	NPC242372
0.7063	Intermediate Similarity	NPC4181
0.7063	Intermediate Similarity	NPC238810
0.7063	Intermediate Similarity	NPC106659
0.7063	Intermediate Similarity	NPC163083
0.7063	Intermediate Similarity	NPC280704
0.7063	Intermediate Similarity	NPC18984
0.7063	Intermediate Similarity	NPC164778
0.7063	Intermediate Similarity	NPC229084
0.7063	Intermediate Similarity	NPC31344
0.7063	Intermediate Similarity	NPC317769
0.7063	Intermediate Similarity	NPC197757
0.7059	Intermediate Similarity	NPC146422
0.7047	Intermediate Similarity	NPC284855
0.7047	Intermediate Similarity	NPC473463
0.7047	Intermediate Similarity	NPC282477
0.7042	Intermediate Similarity	NPC290451
0.7042	Intermediate Similarity	NPC127389
0.7042	Intermediate Similarity	NPC49341
0.7021	Intermediate Similarity	NPC474565
0.7015	Intermediate Similarity	NPC146530
0.7014	Intermediate Similarity	NPC20443
0.7014	Intermediate Similarity	NPC246704
0.7014	Intermediate Similarity	NPC183446
0.7014	Intermediate Similarity	NPC273686
0.7014	Intermediate Similarity	NPC312404
0.7014	Intermediate Similarity	NPC60517
0.7014	Intermediate Similarity	NPC5796
0.7014	Intermediate Similarity	NPC206487
0.7014	Intermediate Similarity	NPC74478
0.7014	Intermediate Similarity	NPC146886
0.6981	Remote Similarity	NPC127402
0.6974	Remote Similarity	NPC231572
0.6972	Remote Similarity	NPC284078

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 NPC174754 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	970
0.2-0.3	1363
0.3-0.4	3033
0.4-0.5	2338
0.5-0.6	1043
0.6-0.7	235
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7826	Intermediate Similarity	NPD1232	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD228	Approved
0.7692	Intermediate Similarity	NPD1558	Phase 1
0.7676	Intermediate Similarity	NPD3145	Approved
0.7676	Intermediate Similarity	NPD3144	Approved
0.7622	Intermediate Similarity	NPD2674	Phase 3
0.75	Intermediate Similarity	NPD2922	Phase 1
0.7379	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7153	Discontinued
0.7095	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5111	Phase 2
0.7075	Intermediate Similarity	NPD5110	Phase 2
0.7075	Intermediate Similarity	NPD5109	Approved
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9377	Approved
0.7059	Intermediate Similarity	NPD9379	Approved
0.7037	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1223	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2219	Phase 1
0.695	Remote Similarity	NPD1357	Approved
0.6943	Remote Similarity	NPD4123	Phase 3
0.6903	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5604	Discontinued
0.6875	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9296	Approved
0.6871	Remote Similarity	NPD9494	Approved
0.6863	Remote Similarity	NPD2161	Phase 2
0.6846	Remote Similarity	NPD1039	Discontinued
0.6839	Remote Similarity	NPD3060	Approved
0.6835	Remote Similarity	NPD4739	Approved
0.6812	Remote Similarity	NPD821	Approved
0.68	Remote Similarity	NPD1423	Approved
0.6792	Remote Similarity	NPD1350	Approved
0.6792	Remote Similarity	NPD7526	Approved
0.6792	Remote Similarity	NPD1349	Approved
0.6792	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD52	Approved
0.6792	Remote Similarity	NPD1351	Approved
0.6783	Remote Similarity	NPD9381	Approved
0.6783	Remote Similarity	NPD9384	Approved
0.6779	Remote Similarity	NPD3027	Phase 3
0.677	Remote Similarity	NPD3111	Phase 1
0.6763	Remote Similarity	NPD5283	Phase 1
0.6752	Remote Similarity	NPD302	Approved
0.675	Remote Similarity	NPD2122	Discontinued
0.673	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4678	Approved
0.6728	Remote Similarity	NPD4675	Approved
0.6712	Remote Similarity	NPD9622	Approved
0.6712	Remote Similarity	NPD4129	Approved
0.6712	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD487	Discontinued
0.6689	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6331	Phase 2
0.6667	Remote Similarity	NPD4097	Suspended
0.6667	Remote Similarity	NPD2808	Discontinued
0.6644	Remote Similarity	NPD455	Discontinued
0.6644	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD1642	Discontinued
0.6624	Remote Similarity	NPD4162	Approved
0.6623	Remote Similarity	NPD5718	Phase 2
0.6622	Remote Similarity	NPD3568	Approved
0.6622	Remote Similarity	NPD3567	Approved
0.66	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1669	Approved
0.6582	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD840	Approved
0.6579	Remote Similarity	NPD839	Approved
0.6577	Remote Similarity	NPD9620	Approved
0.6577	Remote Similarity	NPD6584	Phase 3
0.6577	Remote Similarity	NPD9621	Approved
0.6577	Remote Similarity	NPD9619	Approved
0.6573	Remote Similarity	NPD5536	Phase 2
0.6564	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4357	Discontinued
0.6554	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5310	Approved
0.6554	Remote Similarity	NPD5311	Approved
0.6545	Remote Similarity	NPD5720	Discontinued
0.6536	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD3620	Phase 2
0.6531	Remote Similarity	NPD2231	Phase 2
0.6531	Remote Similarity	NPD2235	Phase 2
0.6522	Remote Similarity	NPD2684	Approved
0.6513	Remote Similarity	NPD1048	Approved
0.651	Remote Similarity	NPD3055	Approved
0.651	Remote Similarity	NPD1817	Approved
0.651	Remote Similarity	NPD1820	Approved
0.651	Remote Similarity	NPD1819	Approved
0.651	Remote Similarity	NPD1818	Approved
0.651	Remote Similarity	NPD3053	Approved
0.6509	Remote Similarity	NPD2644	Approved
0.6506	Remote Similarity	NPD2977	Approved
0.6506	Remote Similarity	NPD2978	Approved
0.6503	Remote Similarity	NPD2883	Discontinued
0.6497	Remote Similarity	NPD1375	Discontinued
0.6491	Remote Similarity	NPD4083	Discontinued
0.649	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD3021	Approved
0.6475	Remote Similarity	NPD3022	Approved
0.6475	Remote Similarity	NPD556	Approved
0.6471	Remote Similarity	NPD259	Phase 1
0.6466	Remote Similarity	NPD9273	Approved
0.6463	Remote Similarity	NPD776	Approved
0.6463	Remote Similarity	NPD824	Approved
0.6463	Remote Similarity	NPD4005	Discontinued
0.6453	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2653	Approved
0.6449	Remote Similarity	NPD290	Approved
0.6447	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5241	Discontinued
0.6438	Remote Similarity	NPD2667	Approved
0.6438	Remote Similarity	NPD2668	Approved
0.6433	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1613	Approved
0.6424	Remote Similarity	NPD1712	Approved
0.6424	Remote Similarity	NPD4993	Discontinued
0.6424	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD2233	Approved
0.6419	Remote Similarity	NPD2232	Approved
0.6419	Remote Similarity	NPD2230	Approved
0.6415	Remote Similarity	NPD4237	Approved
0.6415	Remote Similarity	NPD4236	Phase 3
0.641	Remote Similarity	NPD6895	Approved
0.641	Remote Similarity	NPD6896	Approved
0.6407	Remote Similarity	NPD5772	Approved
0.6407	Remote Similarity	NPD5773	Approved
0.6407	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD601	Approved
0.6405	Remote Similarity	NPD597	Approved
0.6405	Remote Similarity	NPD598	Approved
0.6402	Remote Similarity	NPD3687	Approved
0.6402	Remote Similarity	NPD3686	Approved
0.6395	Remote Similarity	NPD1983	Approved
0.6395	Remote Similarity	NPD1980	Approved
0.6395	Remote Similarity	NPD1981	Approved
0.6392	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD555	Phase 2
0.6387	Remote Similarity	NPD275	Approved
0.6387	Remote Similarity	NPD274	Approved
0.6382	Remote Similarity	NPD596	Approved
0.6382	Remote Similarity	NPD600	Approved
0.638	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD6582	Phase 2
0.6376	Remote Similarity	NPD2983	Phase 2
0.6376	Remote Similarity	NPD2982	Phase 2
0.6376	Remote Similarity	NPD6583	Phase 3
0.6369	Remote Similarity	NPD6380	Phase 1
0.6364	Remote Similarity	NPD1136	Approved
0.6364	Remote Similarity	NPD1132	Approved
0.6364	Remote Similarity	NPD1130	Approved
0.6358	Remote Similarity	NPD1774	Approved
0.6357	Remote Similarity	NPD9713	Approved
0.6352	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.635	Remote Similarity	NPD9610	Approved
0.635	Remote Similarity	NPD9608	Approved
0.6347	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD5722	Discontinued
0.6346	Remote Similarity	NPD2157	Approved
0.634	Remote Similarity	NPD3166	Approved
0.634	Remote Similarity	NPD3164	Approved
0.634	Remote Similarity	NPD3179	Approved
0.634	Remote Similarity	NPD3165	Approved
0.634	Remote Similarity	NPD3180	Approved
0.634	Remote Similarity	NPD3167	Approved
0.6338	Remote Similarity	NPD7843	Approved
0.6324	Remote Similarity	NPD291	Approved
0.6319	Remote Similarity	NPD3985	Discontinued
0.6319	Remote Similarity	NPD7157	Approved
0.6319	Remote Similarity	NPD709	Approved
0.6316	Remote Similarity	NPD2250	Discontinued
0.6316	Remote Similarity	NPD9569	Approved
0.6312	Remote Similarity	NPD5177	Phase 3
0.631	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD3070	Discontinued
0.6309	Remote Similarity	NPD2981	Phase 2
0.6306	Remote Similarity	NPD6111	Discontinued
0.6303	Remote Similarity	NPD5267	Discontinued
0.6303	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1794	Approved
0.6289	Remote Similarity	NPD1803	Phase 3
0.6284	Remote Similarity	NPD3421	Phase 3
0.6275	Remote Similarity	NPD682	Discontinued
0.6272	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD3685	Discontinued
0.6266	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD1798	Approved
0.6259	Remote Similarity	NPD1797	Approved
0.6259	Remote Similarity	NPD968	Approved
0.625	Remote Similarity	NPD9614	Approved
0.625	Remote Similarity	NPD258	Approved
0.625	Remote Similarity	NPD9299	Approved
0.625	Remote Similarity	NPD257	Approved

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