NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	148.05
Volume:	160.062
LogP:	1.76
LogD:	1.477
LogS:	-1.623
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.511
Synthetic Accessibility Score:	2.167
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:	-4.555
MDCK Permeability:	1.5083763173606712e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.597
Plasma Protein Binding (PPB):	80.24401092529297%
Volume Distribution (VD):	1.048
Pgp-substrate:	17.810148239135742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.867
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	10.138
Half-life (T1/2):	0.897

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.135
AMES Toxicity:	0.832
Rat Oral Acute Toxicity:	0.945
Maximum Recommended Daily Dose:	0.356
Skin Sensitization:	0.954
Carcinogencity:	0.682
Eye Corrosion:	0.351
Eye Irritation:	0.99
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC286006

Natural Product ID:	NPC286006
*Common Name:**	P-Hydroxycinnamaldehyde
IUPAC Name:	(E)-3-(4-hydroxyphenyl)prop-2-enal
Synonyms:
Standard InCHIKey:	CJXMVKYNVIGQBS-OWOJBTEDSA-N
Standard InCHI:	InChI=1S/C9H8O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-7,11H/b2-1+
SMILES:	C(=Cc1ccc(cc1)O)/C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL431836
PubChem CID:	641301
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000029] Cinnamaldehydes

*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
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO2166	Ajania fruticulosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425142]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930771]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO7252	Sonchus oleraceus	Species	Asteraceae	Eukaryota	n.a.	Molise Region, Italy	Autumn 2018	PMID[32803719]
NPO7252	Sonchus oleraceus	Species	Asteraceae	Eukaryota	n.a.	Molise Region, Italy	Spring 2019	PMID[32803719]
NPO7252	Sonchus oleraceus	Species	Asteraceae	Eukaryota	n.a.	Molise Region, Italy		PMID[32803719]
NPO7252	Sonchus oleraceus	Species	Asteraceae	Eukaryota	n.a	The rural area of Viçosa, State of Minas Gerais (MG), Brazil	Adult stage	PMID[35282307]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO27645	Fructus galangae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27645	Fructus galangae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17491	Torreya nuncifera	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17850	Torreya grandis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2901	Ilex taubertiana	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17850	Torreya grandis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1715	Eucalyptus radiata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7252	Sonchus oleraceus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO247	Urceolaria bryophila	Species	Trichodinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2166	Ajania fruticulosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8566	Astragalus curvicarpus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
Others	15
Potency	6

Activity Type	# Activity
Cell Line	3
Individual Protein	8
NON-MOLECULAR	5
Organism	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	IC50	>	100000.0	nM	PMID[490321]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	22.0	%	PMID[490321]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[490323]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	7079.5	nM	PMID[490323]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[490323]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[490323]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	26400.0	nM	PMID[490326]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	20000.0	nM	PMID[490322]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	3548.1	nM	PMID[490323]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	70.79	%	PMID[490324]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	139.56	%	PMID[490324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	8.9	%	PMID[490325]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	12.8	%	PMID[490325]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18300.0	nM	PMID[490325]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	67.4	%	PMID[490325]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	104.5	%	PMID[490325]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	102.7	%	PMID[490325]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	108.3	%	PMID[490325]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	94.3	%	PMID[490325]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	66.8	%	PMID[490325]
NPT2	Others	Unspecified		Inhibition	=	3.3	%	PMID[490325]
NPT2	Others	Unspecified		Inhibition	=	31.1	%	PMID[490325]
NPT2	Others	Unspecified		Inhibition	=	3.5	%	PMID[490325]
NPT2	Others	Unspecified		Inhibition	=	4.4	%	PMID[490325]

☑ 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 NPC286006 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	239
0.1-0.2	2584
0.2-0.3	6379
0.3-0.4	12515
0.4-0.5	6145
0.5-0.6	9951
0.6-0.7	4007
0.7-0.8	743
0.8-0.85	100
0.85-0.9	26
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC283711
0.9341	High Similarity	NPC181709
0.9239	High Similarity	NPC32977
0.9239	High Similarity	NPC81010
0.9111	High Similarity	NPC104216
0.9082	High Similarity	NPC19149
0.8969	High Similarity	NPC304638
0.8958	High Similarity	NPC253746
0.8947	High Similarity	NPC201967
0.8913	High Similarity	NPC300017
0.8876	High Similarity	NPC265146
0.8854	High Similarity	NPC130193
0.8788	High Similarity	NPC219913
0.8778	High Similarity	NPC175313
0.8778	High Similarity	NPC248817
0.8737	High Similarity	NPC257182
0.8737	High Similarity	NPC246679
0.8723	High Similarity	NPC138117
0.8723	High Similarity	NPC325292
0.871	High Similarity	NPC300478
0.8681	High Similarity	NPC197783
0.8667	High Similarity	NPC124436
0.866	High Similarity	NPC171843
0.8614	High Similarity	NPC260952
0.8587	High Similarity	NPC23167
0.8587	High Similarity	NPC184169
0.8586	High Similarity	NPC68269
0.8586	High Similarity	NPC135784
0.8586	High Similarity	NPC470202
0.8571	High Similarity	NPC13755
0.8558	High Similarity	NPC228988
0.8557	High Similarity	NPC140619
0.8542	High Similarity	NPC313650
0.8529	High Similarity	NPC206341
0.85	High Similarity	NPC79672
0.8495	Intermediate Similarity	NPC113460
0.8495	Intermediate Similarity	NPC25493
0.8485	Intermediate Similarity	NPC94343
0.8485	Intermediate Similarity	NPC472585
0.8447	Intermediate Similarity	NPC98392
0.8421	Intermediate Similarity	NPC45040
0.8421	Intermediate Similarity	NPC270547
0.8416	Intermediate Similarity	NPC127676
0.8416	Intermediate Similarity	NPC163734
0.8416	Intermediate Similarity	NPC303141
0.8404	Intermediate Similarity	NPC177420
0.8404	Intermediate Similarity	NPC318325
0.8404	Intermediate Similarity	NPC242240
0.8404	Intermediate Similarity	NPC258219
0.8404	Intermediate Similarity	NPC123273
0.8404	Intermediate Similarity	NPC98772
0.8404	Intermediate Similarity	NPC280347
0.8367	Intermediate Similarity	NPC260000
0.8365	Intermediate Similarity	NPC471535
0.8365	Intermediate Similarity	NPC183700
0.8333	Intermediate Similarity	NPC1786
0.8333	Intermediate Similarity	NPC29989
0.8333	Intermediate Similarity	NPC294902
0.8333	Intermediate Similarity	NPC69332
0.8333	Intermediate Similarity	NPC1075
0.8333	Intermediate Similarity	NPC6984
0.8333	Intermediate Similarity	NPC95178
0.8317	Intermediate Similarity	NPC2518
0.8317	Intermediate Similarity	NPC52087
0.8316	Intermediate Similarity	NPC47950
0.8316	Intermediate Similarity	NPC55561
0.8316	Intermediate Similarity	NPC312304
0.8286	Intermediate Similarity	NPC212718
0.8286	Intermediate Similarity	NPC114682
0.8286	Intermediate Similarity	NPC139946
0.8283	Intermediate Similarity	NPC280869
0.8283	Intermediate Similarity	NPC216468
0.8283	Intermediate Similarity	NPC51333
0.8283	Intermediate Similarity	NPC245561
0.8283	Intermediate Similarity	NPC128723
0.8283	Intermediate Similarity	NPC132078
0.8283	Intermediate Similarity	NPC131587
0.8283	Intermediate Similarity	NPC78119
0.828	Intermediate Similarity	NPC155393
0.8269	Intermediate Similarity	NPC471954
0.8269	Intermediate Similarity	NPC75272
0.8252	Intermediate Similarity	NPC226699
0.8252	Intermediate Similarity	NPC303264
0.8247	Intermediate Similarity	NPC151715
0.8247	Intermediate Similarity	NPC128062
0.8235	Intermediate Similarity	NPC243677
0.8229	Intermediate Similarity	NPC204210
0.8229	Intermediate Similarity	NPC155908
0.8229	Intermediate Similarity	NPC304541
0.82	Intermediate Similarity	NPC52472
0.82	Intermediate Similarity	NPC213730
0.8191	Intermediate Similarity	NPC307235
0.8191	Intermediate Similarity	NPC407
0.8182	Intermediate Similarity	NPC175298
0.8173	Intermediate Similarity	NPC17525
0.8172	Intermediate Similarity	NPC150837
0.8172	Intermediate Similarity	NPC286904
0.8165	Intermediate Similarity	NPC39793
0.8163	Intermediate Similarity	NPC26244
0.8163	Intermediate Similarity	NPC274678
0.8155	Intermediate Similarity	NPC70843
0.8137	Intermediate Similarity	NPC93831
0.8131	Intermediate Similarity	NPC11824
0.8131	Intermediate Similarity	NPC95381
0.8119	Intermediate Similarity	NPC110764
0.8119	Intermediate Similarity	NPC91461
0.8119	Intermediate Similarity	NPC471578
0.8119	Intermediate Similarity	NPC7686
0.8119	Intermediate Similarity	NPC101025
0.8119	Intermediate Similarity	NPC84325
0.8119	Intermediate Similarity	NPC40258
0.8113	Intermediate Similarity	NPC226250
0.8113	Intermediate Similarity	NPC470355
0.8105	Intermediate Similarity	NPC27974
0.8095	Intermediate Similarity	NPC95172
0.8095	Intermediate Similarity	NPC88141
0.8091	Intermediate Similarity	NPC184527
0.8081	Intermediate Similarity	NPC82664
0.8081	Intermediate Similarity	NPC216520
0.8081	Intermediate Similarity	NPC292730
0.8081	Intermediate Similarity	NPC473388
0.8081	Intermediate Similarity	NPC132271
0.8061	Intermediate Similarity	NPC316301
0.8061	Intermediate Similarity	NPC27323
0.8056	Intermediate Similarity	NPC217472
0.8056	Intermediate Similarity	NPC33749
0.8056	Intermediate Similarity	NPC328593
0.8056	Intermediate Similarity	NPC285350
0.8056	Intermediate Similarity	NPC261453
0.8039	Intermediate Similarity	NPC62351
0.8039	Intermediate Similarity	NPC179686
0.8021	Intermediate Similarity	NPC70436
0.8019	Intermediate Similarity	NPC116842
0.8019	Intermediate Similarity	NPC222905
0.8	Intermediate Similarity	NPC317305
0.8	Intermediate Similarity	NPC107619
0.8	Intermediate Similarity	NPC109955
0.8	Intermediate Similarity	NPC470039
0.8	Intermediate Similarity	NPC31274
0.8	Intermediate Similarity	NPC474073
0.7982	Intermediate Similarity	NPC23402
0.7982	Intermediate Similarity	NPC474967
0.7982	Intermediate Similarity	NPC233669
0.7982	Intermediate Similarity	NPC278102
0.798	Intermediate Similarity	NPC8392
0.798	Intermediate Similarity	NPC107522
0.7961	Intermediate Similarity	NPC261573
0.7961	Intermediate Similarity	NPC8931
0.7961	Intermediate Similarity	NPC12278
0.7961	Intermediate Similarity	NPC120693
0.7944	Intermediate Similarity	NPC268388
0.7944	Intermediate Similarity	NPC297657
0.7938	Intermediate Similarity	NPC151764
0.7938	Intermediate Similarity	NPC192
0.7925	Intermediate Similarity	NPC326187
0.7925	Intermediate Similarity	NPC79543
0.7921	Intermediate Similarity	NPC80027
0.7921	Intermediate Similarity	NPC92730
0.7921	Intermediate Similarity	NPC100870
0.7921	Intermediate Similarity	NPC275104
0.7917	Intermediate Similarity	NPC19680
0.7909	Intermediate Similarity	NPC281277
0.7905	Intermediate Similarity	NPC141523
0.7905	Intermediate Similarity	NPC34715
0.7905	Intermediate Similarity	NPC29883
0.79	Intermediate Similarity	NPC202986
0.7885	Intermediate Similarity	NPC227255
0.7885	Intermediate Similarity	NPC233396
0.7885	Intermediate Similarity	NPC13495
0.7885	Intermediate Similarity	NPC154899
0.7885	Intermediate Similarity	NPC128730
0.7885	Intermediate Similarity	NPC288760
0.7876	Intermediate Similarity	NPC131868
0.7876	Intermediate Similarity	NPC216216
0.787	Intermediate Similarity	NPC51698
0.787	Intermediate Similarity	NPC231717
0.7864	Intermediate Similarity	NPC305205
0.7864	Intermediate Similarity	NPC477802
0.7864	Intermediate Similarity	NPC477801
0.7857	Intermediate Similarity	NPC231150
0.7857	Intermediate Similarity	NPC306074
0.785	Intermediate Similarity	NPC21162
0.785	Intermediate Similarity	NPC63345
0.785	Intermediate Similarity	NPC252544
0.785	Intermediate Similarity	NPC179309
0.785	Intermediate Similarity	NPC321252
0.7843	Intermediate Similarity	NPC294741
0.7843	Intermediate Similarity	NPC223393
0.7843	Intermediate Similarity	NPC161571
0.7843	Intermediate Similarity	NPC248573
0.7843	Intermediate Similarity	NPC275053
0.7843	Intermediate Similarity	NPC130103
0.7843	Intermediate Similarity	NPC174911
0.7838	Intermediate Similarity	NPC122117
0.7838	Intermediate Similarity	NPC174087
0.7838	Intermediate Similarity	NPC65791
0.783	Intermediate Similarity	NPC224584
0.7822	Intermediate Similarity	NPC225464
0.7822	Intermediate Similarity	NPC88420
0.7822	Intermediate Similarity	NPC77492

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 NPC286006 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	1152
0.2-0.3	1423
0.3-0.4	3041
0.4-0.5	1939
0.5-0.6	1019
0.6-0.7	300
0.7-0.8	46
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD111	Approved
0.8247	Intermediate Similarity	NPD2933	Approved
0.8247	Intermediate Similarity	NPD2934	Approved
0.8163	Intermediate Similarity	NPD2859	Approved
0.8163	Intermediate Similarity	NPD2860	Approved
0.8061	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD3020	Approved
0.7905	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1242	Phase 1
0.781	Intermediate Similarity	NPD3134	Approved
0.7768	Intermediate Similarity	NPD9545	Approved
0.7767	Intermediate Similarity	NPD846	Approved
0.7767	Intermediate Similarity	NPD940	Approved
0.7736	Intermediate Similarity	NPD1358	Approved
0.764	Intermediate Similarity	NPD9087	Approved
0.7624	Intermediate Similarity	NPD1809	Phase 2
0.7624	Intermediate Similarity	NPD844	Approved
0.76	Intermediate Similarity	NPD845	Approved
0.7593	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD9294	Approved
0.7549	Intermediate Similarity	NPD288	Approved
0.75	Intermediate Similarity	NPD9088	Approved
0.75	Intermediate Similarity	NPD74	Approved
0.75	Intermediate Similarity	NPD9266	Approved
0.75	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD968	Approved
0.7453	Intermediate Similarity	NPD9610	Approved
0.7453	Intermediate Similarity	NPD9608	Approved
0.7434	Intermediate Similarity	NPD9493	Approved
0.7417	Intermediate Similarity	NPD9494	Approved
0.7407	Intermediate Similarity	NPD9267	Approved
0.7407	Intermediate Similarity	NPD9264	Approved
0.7407	Intermediate Similarity	NPD9263	Approved
0.7321	Intermediate Similarity	NPD1241	Discontinued
0.7308	Intermediate Similarity	NPD9273	Approved
0.7297	Intermediate Similarity	NPD228	Approved
0.7273	Intermediate Similarity	NPD3021	Approved
0.7273	Intermediate Similarity	NPD3022	Approved
0.7227	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD256	Approved
0.7193	Intermediate Similarity	NPD255	Approved
0.7188	Intermediate Similarity	NPD9089	Approved
0.7182	Intermediate Similarity	NPD2684	Approved
0.7174	Intermediate Similarity	NPD9716	Approved
0.717	Intermediate Similarity	NPD3028	Approved
0.7143	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1237	Approved
0.713	Intermediate Similarity	NPD9568	Approved
0.7129	Intermediate Similarity	NPD9256	Approved
0.7129	Intermediate Similarity	NPD9258	Approved
0.7094	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD290	Approved
0.7083	Intermediate Similarity	NPD9093	Approved
0.708	Intermediate Similarity	NPD821	Approved
0.708	Intermediate Similarity	NPD9379	Approved
0.708	Intermediate Similarity	NPD9377	Approved
0.7069	Intermediate Similarity	NPD317	Approved
0.7069	Intermediate Similarity	NPD318	Approved
0.7069	Intermediate Similarity	NPD856	Approved
0.7069	Intermediate Similarity	NPD16	Approved
0.7064	Intermediate Similarity	NPD9697	Approved
0.7059	Intermediate Similarity	NPD422	Phase 1
0.7037	Intermediate Similarity	NPD9500	Approved
0.7037	Intermediate Similarity	NPD9261	Approved
0.7034	Intermediate Similarity	NPD4626	Approved
0.703	Intermediate Similarity	NPD9295	Approved
0.7018	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2234	Approved
0.7018	Intermediate Similarity	NPD2228	Approved
0.7018	Intermediate Similarity	NPD2229	Approved
0.7009	Intermediate Similarity	NPD3091	Approved
0.7009	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD1445	Approved
0.7	Intermediate Similarity	NPD1444	Approved
0.6981	Remote Similarity	NPD9495	Approved
0.6967	Remote Similarity	NPD1164	Approved
0.6957	Remote Similarity	NPD9614	Approved
0.6957	Remote Similarity	NPD9281	Approved
0.6957	Remote Similarity	NPD9618	Approved
0.693	Remote Similarity	NPD7843	Approved
0.6923	Remote Similarity	NPD5536	Phase 2
0.6903	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD3019	Approved
0.6891	Remote Similarity	NPD9384	Approved
0.6891	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2932	Approved
0.6891	Remote Similarity	NPD9381	Approved
0.6864	Remote Similarity	NPD1894	Discontinued
0.6855	Remote Similarity	NPD4208	Discontinued
0.6833	Remote Similarity	NPD3496	Discontinued
0.6833	Remote Similarity	NPD3421	Phase 3
0.6814	Remote Similarity	NPD4750	Phase 3
0.6814	Remote Similarity	NPD1792	Phase 2
0.6807	Remote Similarity	NPD1357	Approved
0.6807	Remote Similarity	NPD5691	Approved
0.68	Remote Similarity	NPD9073	Approved
0.6786	Remote Similarity	NPD2342	Discontinued
0.678	Remote Similarity	NPD9616	Approved
0.678	Remote Similarity	NPD9613	Approved
0.678	Remote Similarity	NPD9615	Approved
0.6777	Remote Similarity	NPD1535	Discovery
0.6777	Remote Similarity	NPD3092	Approved
0.6777	Remote Similarity	NPD1201	Approved
0.6777	Remote Similarity	NPD1610	Phase 2
0.6772	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD9094	Approved
0.6752	Remote Similarity	NPD7157	Approved
0.6735	Remote Similarity	NPD9250	Approved
0.6733	Remote Similarity	NPD9257	Approved
0.6733	Remote Similarity	NPD9259	Approved
0.6731	Remote Similarity	NPD9365	Approved
0.6723	Remote Similarity	NPD1759	Phase 1
0.6723	Remote Similarity	NPD316	Approved
0.6721	Remote Similarity	NPD9717	Approved
0.6721	Remote Similarity	NPD2561	Approved
0.6721	Remote Similarity	NPD9269	Phase 2
0.6721	Remote Similarity	NPD2562	Approved
0.6721	Remote Similarity	NPD1481	Phase 2
0.672	Remote Similarity	NPD5736	Approved
0.6719	Remote Similarity	NPD1240	Approved
0.6699	Remote Similarity	NPD689	Discontinued
0.6698	Remote Similarity	NPD9296	Approved
0.6694	Remote Similarity	NPD3847	Discontinued
0.6694	Remote Similarity	NPD1470	Approved
0.6694	Remote Similarity	NPD1203	Approved
0.6693	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9268	Approved
0.6667	Remote Similarity	NPD475	Phase 2
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD4659	Approved
0.6667	Remote Similarity	NPD1282	Approved
0.6667	Remote Similarity	NPD6583	Phase 3
0.6667	Remote Similarity	NPD5451	Approved
0.6667	Remote Similarity	NPD4207	Discontinued
0.6667	Remote Similarity	NPD6582	Phase 2
0.6667	Remote Similarity	NPD9622	Approved
0.6641	Remote Similarity	NPD1510	Phase 2
0.6641	Remote Similarity	NPD520	Approved
0.6639	Remote Similarity	NPD1758	Phase 1
0.6638	Remote Similarity	NPD5535	Approved
0.6638	Remote Similarity	NPD7635	Approved
0.6615	Remote Similarity	NPD1607	Approved
0.6614	Remote Similarity	NPD3136	Phase 2
0.6612	Remote Similarity	NPD4059	Approved
0.6612	Remote Similarity	NPD1778	Approved
0.6612	Remote Similarity	NPD2286	Discontinued
0.6612	Remote Similarity	NPD3095	Discontinued
0.661	Remote Similarity	NPD6671	Approved
0.6606	Remote Similarity	NPD1238	Approved
0.6604	Remote Similarity	NPD1202	Approved
0.66	Remote Similarity	NPD9491	Approved
0.6591	Remote Similarity	NPD1551	Phase 2
0.6589	Remote Similarity	NPD943	Approved
0.6587	Remote Similarity	NPD4212	Discontinued
0.6585	Remote Similarity	NPD3972	Approved
0.6583	Remote Similarity	NPD5304	Approved
0.6583	Remote Similarity	NPD5303	Approved
0.6577	Remote Similarity	NPD6647	Phase 2
0.656	Remote Similarity	NPD3094	Phase 2
0.656	Remote Similarity	NPD1131	Approved
0.656	Remote Similarity	NPD1135	Approved
0.656	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4103	Phase 2
0.656	Remote Similarity	NPD1133	Approved
0.656	Remote Similarity	NPD1134	Approved
0.656	Remote Similarity	NPD1129	Approved
0.6552	Remote Similarity	NPD969	Suspended
0.6541	Remote Similarity	NPD7266	Discontinued
0.6532	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4093	Discontinued
0.6525	Remote Similarity	NPD1791	Approved
0.6525	Remote Similarity	NPD1793	Approved
0.6514	Remote Similarity	NPD9612	Approved
0.6514	Remote Similarity	NPD9611	Approved
0.6514	Remote Similarity	NPD9609	Approved
0.6512	Remote Similarity	NPD6663	Approved
0.6509	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6584	Phase 3
0.6508	Remote Similarity	NPD257	Approved
0.6508	Remote Similarity	NPD258	Approved
0.6508	Remote Similarity	NPD9621	Approved
0.6508	Remote Similarity	NPD9620	Approved
0.6508	Remote Similarity	NPD9619	Approved
0.6504	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD1549	Phase 2
0.648	Remote Similarity	NPD1876	Approved
0.648	Remote Similarity	NPD1283	Approved
0.648	Remote Similarity	NPD196	Phase 1
0.648	Remote Similarity	NPD3225	Approved
0.6475	Remote Similarity	NPD2667	Approved
0.6475	Remote Similarity	NPD1751	Approved
0.6475	Remote Similarity	NPD4589	Approved
0.6475	Remote Similarity	NPD5846	Approved
0.6475	Remote Similarity	NPD2668	Approved
0.6475	Remote Similarity	NPD6516	Phase 2
0.6466	Remote Similarity	NPD2935	Discontinued

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