NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.08
Volume:	223.661
LogP:	0.501
LogD:	0.884
LogS:	-1.954
# Rotatable Bonds:	5
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.732
Synthetic Accessibility Score:	2.048
Fsp3:	0.364
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:	-4.668
MDCK Permeability:	1.710810829536058e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.893
Plasma Protein Binding (PPB):	45.04535675048828%
Volume Distribution (VD):	0.93
Pgp-substrate:	48.69221496582031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.259
CYP1A2-substrate:	0.77
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.417
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.501
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.368
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	9.332
Half-life (T1/2):	0.937

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.447
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.428
Carcinogencity:	0.037
Eye Corrosion:	0.056
Eye Irritation:	0.784
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC4796

Natural Product ID:	NPC4796
*Common Name:**	3-Hydroxy-1-(4-Hydroxy-3,5-Dimethoxyphenyl)Propan-1-One
IUPAC Name:	3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	UHOAHNLBCNGCHE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O5/c1-15-9-5-7(8(13)3-4-12)6-10(16-2)11(9)14/h5-6,12,14H,3-4H2,1-2H3
SMILES:	OCCC(=O)c1cc(OC)c(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1760596
PubChem CID:	54353627
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO3973	Flammulina velutipes	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473426]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974602]
NPO9771	Aka coralliphagum	Species	Niphatidae	Eukaryota	n.a.	San Salvador in the Bahamas (12-26 m depth)	2001-MAR; 2003-JUL	PMID[17309298]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19813743]
NPO13341	Bryopsis pennata	Species	Bryopsidaceae	Eukaryota	n.a.	Hawaiian	n.a.	PMID[19916528]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21420296]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	trunk	Jeju island, Korea	2005-Dec	PMID[21420296]
NPO11402	Tithonia rotundifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO3973	Flammulina velutipes	Species	Physalacriaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17479	Aconitum tanguticum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4853	Carduus crispus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17479	Aconitum tanguticum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27048	Pyropia tenera	Species	Bangiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4853	Carduus crispus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14222	Schefflera divaricata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11402	Tithonia rotundifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2684	Cortinarius vinosipes	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12356	Aphelandra chamissoniana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3026	Strophanthus hispidus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11166	Sclerodoris tanya	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13834	Lecidea carpathica	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3973	Flammulina velutipes	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18809	Lyophyllum connatum	Species	Lyophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10468	Ficus beecheyana	Species	Ficidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18724	Polyalthia stenopetala	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19389	Roemeria refracta	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14310	Tecoma heptaphylla	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26105	Panax spinosus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11758	Parmelia pokornyi	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18478	Vernonia scorpioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27048	Pyropia tenera	Species	Bangiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27114	Aconitum habaense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13451	Pseudotsuga japonica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17479	Aconitum tanguticum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13119	Hymenoxys microcephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14637	Saussurea cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19586	Bougainvillea glabra	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9771	Aka coralliphagum	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18218	Acanthophyllum sordidum	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17344	Strychnos henningsii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13341	Bryopsis pennata	Species	Bryopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4385	Aconitum zuccarini	Species	Ranunculaceae	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

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[543625]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	30000.0	nM	PMID[543625]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	24300.0	nM	PMID[543625]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[543625]

☑ 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 NPC4796 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	366
0.1-0.2	1608
0.2-0.3	4766
0.3-0.4	10679
0.4-0.5	7071
0.5-0.6	3764
0.6-0.7	5520
0.7-0.8	6692
0.8-0.85	1838
0.85-0.9	342
0.9-0.95	49
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC208760
0.9485	High Similarity	NPC50823
0.9403	High Similarity	NPC274613
0.9362	High Similarity	NPC474903
0.9348	High Similarity	NPC299154
0.9338	High Similarity	NPC325625
0.9328	High Similarity	NPC237330
0.9323	High Similarity	NPC50763
0.9265	High Similarity	NPC95679
0.9265	High Similarity	NPC25305
0.9265	High Similarity	NPC125417
0.9265	High Similarity	NPC110899
0.9265	High Similarity	NPC112068
0.9259	High Similarity	NPC139519
0.922	High Similarity	NPC226987
0.922	High Similarity	NPC143903
0.9214	High Similarity	NPC142165
0.9209	High Similarity	NPC312256
0.9161	High Similarity	NPC264289
0.9161	High Similarity	NPC142876
0.9161	High Similarity	NPC333691
0.9161	High Similarity	NPC139293
0.9161	High Similarity	NPC200060
0.9161	High Similarity	NPC69430
0.9161	High Similarity	NPC40290
0.9161	High Similarity	NPC264550
0.9161	High Similarity	NPC195763
0.9155	High Similarity	NPC188074
0.9155	High Similarity	NPC125449
0.9143	High Similarity	NPC254659
0.9143	High Similarity	NPC287722
0.9137	High Similarity	NPC110419
0.9091	High Similarity	NPC80710
0.9091	High Similarity	NPC194653
0.9091	High Similarity	NPC287395
0.9091	High Similarity	NPC183655
0.9091	High Similarity	NPC254702
0.9091	High Similarity	NPC139364
0.9091	High Similarity	NPC203747
0.9078	High Similarity	NPC207732
0.9071	High Similarity	NPC284556
0.9071	High Similarity	NPC301178
0.9044	High Similarity	NPC155098
0.9041	High Similarity	NPC25127
0.9041	High Similarity	NPC287504
0.9034	High Similarity	NPC45291
0.9034	High Similarity	NPC19980
0.9034	High Similarity	NPC31363
0.9028	High Similarity	NPC92722
0.9028	High Similarity	NPC102003
0.9021	High Similarity	NPC30647
0.9021	High Similarity	NPC61871
0.9021	High Similarity	NPC55557
0.9007	High Similarity	NPC119663
0.9007	High Similarity	NPC46161
0.9007	High Similarity	NPC239608
0.9007	High Similarity	NPC471417
0.8993	High Similarity	NPC203351
0.8973	High Similarity	NPC209487
0.8973	High Similarity	NPC477231
0.8973	High Similarity	NPC131266
0.8973	High Similarity	NPC216769
0.8973	High Similarity	NPC100971
0.8973	High Similarity	NPC245382
0.8973	High Similarity	NPC257648
0.8973	High Similarity	NPC181209
0.8973	High Similarity	NPC35763
0.8973	High Similarity	NPC100263
0.8973	High Similarity	NPC121522
0.8973	High Similarity	NPC269451
0.8973	High Similarity	NPC291802
0.8966	High Similarity	NPC29231
0.8966	High Similarity	NPC472279
0.8958	High Similarity	NPC131451
0.8958	High Similarity	NPC15329
0.8951	High Similarity	NPC165389
0.8951	High Similarity	NPC12377
0.8947	High Similarity	NPC32163
0.8947	High Similarity	NPC16651
0.8944	High Similarity	NPC38065
0.8944	High Similarity	NPC242893
0.8912	High Similarity	NPC250557
0.8912	High Similarity	NPC124714
0.8904	High Similarity	NPC256406
0.8904	High Similarity	NPC151425
0.8889	High Similarity	NPC168803
0.8889	High Similarity	NPC119660
0.8889	High Similarity	NPC93034
0.8881	High Similarity	NPC304747
0.8881	High Similarity	NPC472917
0.8881	High Similarity	NPC157133
0.8859	High Similarity	NPC78103
0.8851	High Similarity	NPC134287
0.8851	High Similarity	NPC2928
0.8851	High Similarity	NPC130589
0.8851	High Similarity	NPC39184
0.8844	High Similarity	NPC39732
0.8844	High Similarity	NPC60972
0.8844	High Similarity	NPC101996
0.8841	High Similarity	NPC143649
0.8836	High Similarity	NPC156953
0.8836	High Similarity	NPC10467
0.8836	High Similarity	NPC239363
0.8836	High Similarity	NPC96501
0.8832	High Similarity	NPC159418
0.8832	High Similarity	NPC156124
0.8832	High Similarity	NPC1321
0.8832	High Similarity	NPC304929
0.8832	High Similarity	NPC283823
0.8828	High Similarity	NPC43669
0.8828	High Similarity	NPC238279
0.8828	High Similarity	NPC272721
0.8828	High Similarity	NPC120464
0.8828	High Similarity	NPC196277
0.8828	High Similarity	NPC203077
0.8828	High Similarity	NPC218490
0.8828	High Similarity	NPC166036
0.8824	High Similarity	NPC264145
0.8811	High Similarity	NPC105213
0.88	High Similarity	NPC477410
0.8794	High Similarity	NPC469523
0.8792	High Similarity	NPC472916
0.8784	High Similarity	NPC88645
0.8784	High Similarity	NPC206238
0.8784	High Similarity	NPC281477
0.8784	High Similarity	NPC271779
0.8784	High Similarity	NPC167091
0.8784	High Similarity	NPC292214
0.8784	High Similarity	NPC469550
0.8777	High Similarity	NPC156892
0.8776	High Similarity	NPC262623
0.8776	High Similarity	NPC171010
0.8776	High Similarity	NPC75695
0.8767	High Similarity	NPC177298
0.8767	High Similarity	NPC48479
0.8767	High Similarity	NPC137062
0.8767	High Similarity	NPC287101
0.8767	High Similarity	NPC183950
0.8767	High Similarity	NPC52005
0.8767	High Similarity	NPC38545
0.8767	High Similarity	NPC171916
0.8767	High Similarity	NPC134293
0.8767	High Similarity	NPC223579
0.8759	High Similarity	NPC95864
0.8759	High Similarity	NPC77378
0.8759	High Similarity	NPC111888
0.875	High Similarity	NPC299010
0.8733	High Similarity	NPC299520
0.8733	High Similarity	NPC99597
0.8733	High Similarity	NPC129684
0.8733	High Similarity	NPC210084
0.8733	High Similarity	NPC52530
0.8733	High Similarity	NPC470402
0.8725	High Similarity	NPC472887
0.8725	High Similarity	NPC82592
0.8725	High Similarity	NPC230149
0.8725	High Similarity	NPC152951
0.8725	High Similarity	NPC256612
0.8725	High Similarity	NPC117992
0.8725	High Similarity	NPC38898
0.8725	High Similarity	NPC168247
0.8725	High Similarity	NPC79998
0.8725	High Similarity	NPC213622
0.8725	High Similarity	NPC16082
0.8725	High Similarity	NPC208197
0.8725	High Similarity	NPC57674
0.8725	High Similarity	NPC20830
0.8716	High Similarity	NPC275722
0.8716	High Similarity	NPC188203
0.8716	High Similarity	NPC256283
0.8716	High Similarity	NPC162313
0.8716	High Similarity	NPC275836
0.8716	High Similarity	NPC149889
0.8716	High Similarity	NPC302950
0.8716	High Similarity	NPC180234
0.8716	High Similarity	NPC323626
0.8716	High Similarity	NPC57030
0.8716	High Similarity	NPC198826
0.8716	High Similarity	NPC120163
0.8716	High Similarity	NPC236637
0.8716	High Similarity	NPC324233
0.8716	High Similarity	NPC212678
0.8716	High Similarity	NPC120537
0.8716	High Similarity	NPC219582
0.8716	High Similarity	NPC25270
0.8716	High Similarity	NPC156222
0.8716	High Similarity	NPC312338
0.8716	High Similarity	NPC472912
0.8716	High Similarity	NPC39007
0.8716	High Similarity	NPC199100
0.8716	High Similarity	NPC293183
0.8716	High Similarity	NPC55205
0.8716	High Similarity	NPC83508
0.8716	High Similarity	NPC100887
0.8716	High Similarity	NPC239128
0.8716	High Similarity	NPC260979
0.8716	High Similarity	NPC241498
0.8716	High Similarity	NPC301323
0.8716	High Similarity	NPC222830
0.8716	High Similarity	NPC187498

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 NPC4796 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	986
0.2-0.3	1965
0.3-0.4	2680
0.4-0.5	1685
0.5-0.6	975
0.6-0.7	405
0.7-0.8	108
0.8-0.85	17
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8832	High Similarity	NPD230	Phase 1
0.8792	High Similarity	NPD3882	Suspended
0.8716	High Similarity	NPD1934	Approved
0.8667	High Similarity	NPD9494	Approved
0.8658	High Similarity	NPD2801	Approved
0.8552	High Similarity	NPD1511	Approved
0.8435	Intermediate Similarity	NPD1512	Approved
0.8411	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD1510	Phase 2
0.8357	Intermediate Similarity	NPD1240	Approved
0.8357	Intermediate Similarity	NPD943	Approved
0.8291	Intermediate Similarity	NPD3818	Discontinued
0.828	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6166	Phase 2
0.828	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1607	Approved
0.8207	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD9269	Phase 2
0.8125	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7054	Approved
0.8117	Intermediate Similarity	NPD3817	Phase 2
0.8092	Intermediate Similarity	NPD4380	Phase 2
0.8082	Intermediate Similarity	NPD1549	Phase 2
0.8075	Intermediate Similarity	NPD7074	Phase 3
0.8075	Intermediate Similarity	NPD7472	Approved
0.8014	Intermediate Similarity	NPD3027	Phase 3
0.8014	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1465	Phase 2
0.7933	Intermediate Similarity	NPD6799	Approved
0.7927	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6232	Discontinued
0.7917	Intermediate Similarity	NPD447	Suspended
0.7914	Intermediate Similarity	NPD6797	Phase 2
0.7895	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7473	Discontinued
0.7868	Intermediate Similarity	NPD9268	Approved
0.7866	Intermediate Similarity	NPD7251	Discontinued
0.7842	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7808	Phase 3
0.7805	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5494	Approved
0.7785	Intermediate Similarity	NPD7075	Discontinued
0.7785	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2534	Approved
0.7763	Intermediate Similarity	NPD2532	Approved
0.7763	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2533	Approved
0.775	Intermediate Similarity	NPD1247	Approved
0.7736	Intermediate Similarity	NPD919	Approved
0.7707	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2796	Approved
0.7669	Intermediate Similarity	NPD228	Approved
0.7664	Intermediate Similarity	NPD9545	Approved
0.7643	Intermediate Similarity	NPD6801	Discontinued
0.7628	Intermediate Similarity	NPD6599	Discontinued
0.7616	Intermediate Similarity	NPD4628	Phase 3
0.7603	Intermediate Similarity	NPD1613	Approved
0.7603	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7819	Suspended
0.7584	Intermediate Similarity	NPD1551	Phase 2
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7566	Intermediate Similarity	NPD6190	Approved
0.755	Intermediate Similarity	NPD2800	Approved
0.7547	Intermediate Similarity	NPD5402	Approved
0.7547	Intermediate Similarity	NPD5353	Approved
0.7546	Intermediate Similarity	NPD3926	Phase 2
0.7532	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6651	Approved
0.7468	Intermediate Similarity	NPD7411	Suspended
0.7468	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2935	Discontinued
0.7448	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5403	Approved
0.7421	Intermediate Similarity	NPD37	Approved
0.7419	Intermediate Similarity	NPD5401	Approved
0.7407	Intermediate Similarity	NPD6234	Discontinued
0.7389	Intermediate Similarity	NPD1653	Approved
0.7386	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4357	Discontinued
0.7347	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD824	Approved
0.7338	Intermediate Similarity	NPD5536	Phase 2
0.7337	Intermediate Similarity	NPD7685	Pre-registration
0.7337	Intermediate Similarity	NPD6559	Discontinued
0.7333	Intermediate Similarity	NPD5242	Approved
0.7325	Intermediate Similarity	NPD920	Approved
0.732	Intermediate Similarity	NPD1243	Approved
0.732	Intermediate Similarity	NPD2654	Approved
0.7317	Intermediate Similarity	NPD6959	Discontinued
0.7284	Intermediate Similarity	NPD4965	Approved
0.7284	Intermediate Similarity	NPD4967	Phase 2
0.7284	Intermediate Similarity	NPD4966	Approved
0.7273	Intermediate Similarity	NPD9717	Approved
0.7266	Intermediate Similarity	NPD9493	Approved
0.725	Intermediate Similarity	NPD6386	Approved
0.725	Intermediate Similarity	NPD6385	Approved
0.7239	Intermediate Similarity	NPD3749	Approved
0.7212	Intermediate Similarity	NPD7199	Phase 2
0.7208	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7228	Approved
0.7202	Intermediate Similarity	NPD3751	Discontinued
0.7197	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2344	Approved
0.7186	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7768	Phase 2
0.7174	Intermediate Similarity	NPD1241	Discontinued
0.7168	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6099	Approved
0.7124	Intermediate Similarity	NPD6100	Approved
0.7123	Intermediate Similarity	NPD1203	Approved
0.7114	Intermediate Similarity	NPD411	Approved
0.7103	Intermediate Similarity	NPD2983	Phase 2
0.7103	Intermediate Similarity	NPD2982	Phase 2
0.7086	Intermediate Similarity	NPD1933	Approved
0.7083	Intermediate Similarity	NPD422	Phase 1
0.7076	Intermediate Similarity	NPD5953	Discontinued
0.7072	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5710	Approved
0.7066	Intermediate Similarity	NPD5711	Approved
0.7059	Intermediate Similarity	NPD3748	Approved
0.7051	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3972	Approved
0.7034	Intermediate Similarity	NPD2981	Phase 2
0.7034	Intermediate Similarity	NPD1608	Approved
0.7027	Intermediate Similarity	NPD3018	Phase 2
0.7024	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2309	Approved
0.6985	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7266	Discontinued
0.6966	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3787	Discontinued
0.6959	Remote Similarity	NPD7286	Phase 2
0.6951	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD1548	Phase 1
0.6918	Remote Similarity	NPD7390	Discontinued
0.6914	Remote Similarity	NPD3226	Approved
0.6914	Remote Similarity	NPD3455	Phase 2
0.6901	Remote Similarity	NPD2163	Approved
0.6901	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2219	Phase 1
0.6897	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1470	Approved
0.6889	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3764	Approved
0.6875	Remote Similarity	NPD1357	Approved
0.6875	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3146	Approved
0.6867	Remote Similarity	NPD6832	Phase 2
0.6863	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1610	Phase 2
0.6849	Remote Similarity	NPD3705	Approved
0.6849	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5647	Approved
0.6846	Remote Similarity	NPD2798	Approved
0.6846	Remote Similarity	NPD1019	Discontinued
0.6836	Remote Similarity	NPD8434	Phase 2
0.6835	Remote Similarity	NPD8166	Discontinued
0.6829	Remote Similarity	NPD5090	Approved
0.6829	Remote Similarity	NPD5089	Approved
0.6828	Remote Similarity	NPD17	Approved
0.6824	Remote Similarity	NPD1876	Approved
0.6818	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7458	Discontinued
0.6809	Remote Similarity	NPD5283	Phase 1
0.6797	Remote Similarity	NPD3620	Phase 2
0.6797	Remote Similarity	NPD1558	Phase 1
0.6797	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD9570	Approved
0.6792	Remote Similarity	NPD2354	Approved
0.6784	Remote Similarity	NPD2403	Approved
0.6776	Remote Similarity	NPD2313	Discontinued
0.6772	Remote Similarity	NPD8151	Discontinued
0.6772	Remote Similarity	NPD1652	Phase 2
0.6755	Remote Similarity	NPD4908	Phase 1
0.6752	Remote Similarity	NPD2346	Discontinued
0.6743	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7038	Approved
0.6743	Remote Similarity	NPD7240	Approved
0.6743	Remote Similarity	NPD7039	Approved
0.6739	Remote Similarity	NPD1358	Approved
0.6735	Remote Similarity	NPD1201	Approved
0.6733	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7033	Discontinued
0.673	Remote Similarity	NPD4110	Phase 3
0.673	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1729	Discontinued
0.6721	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1778	Approved
0.6711	Remote Similarity	NPD1283	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