NPASS Compound

Structure

CID190043 OpenBabel06191715572D 29 30 0 0 0 0 0 0 0 0999 V2000 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 8 1 0 0 0 0 5 16 2 0 0 0 0 6 9 1 0 0 0 0 6 17 2 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 2 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 20 2 0 0 0 0 15 21 2 0 0 0 0 15 24 1 0 0 0 0 19 25 2 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 24 2 0 0 0 0 23 27 2 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.2
Volume:	432.639
LogP:	6.216
LogD:	4.185
LogS:	-4.077
# Rotatable Bonds:	7
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	2.864
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.942
MDCK Permeability:	2.1089934307383373e-05
Pgp-inhibitor:	0.79
Pgp-substrate:	0.08
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.822
30% Bioavailability (F30%):	0.812

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	99.97544860839844%
Volume Distribution (VD):	1.821
Pgp-substrate:	1.909542441368103%

ADMET: Metabolism

CYP1A2-inhibitor:	0.927
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.884
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.932
CYP2D6-substrate:	0.736
CYP3A4-inhibitor:	0.677
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	16.423
Half-life (T1/2):	0.738

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.809
Drug-inuced Liver Injury (DILI):	0.343
AMES Toxicity:	0.43
Rat Oral Acute Toxicity:	0.292
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.952
Carcinogencity:	0.276
Eye Corrosion:	0.003
Eye Irritation:	0.899
Respiratory Toxicity:	0.774

Download Data

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

Natural Product: NPC190043

Natural Product ID:	NPC190043
*Common Name:**	Abyssinone Vi
IUPAC Name:	(E)-1-(2,4-dihydroxyphenyl)-3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]prop-2-en-1-one
Synonyms:	Abyssinone Vi
Standard InCHIKey:	PEKZTKWPHQWTIM-KPKJPENVSA-N
Standard InCHI:	InChI=1S/C25H28O4/c1-16(2)5-8-19-13-18(14-20(25(19)29)9-6-17(3)4)7-12-23(27)22-11-10-21(26)15-24(22)28/h5-7,10-15,26,28-29H,8-9H2,1-4H3/b12-7+
SMILES:	CC(=CCc1cc(/C=C/C(=O)c2ccc(cc2O)O)cc(c1O)CC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508727
PubChem CID:	5281219
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[12828487]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17517504]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	Barks	n.a.	n.a.	PMID[18302333]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20934335]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22281186]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23022281]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588326]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27387	Erythrina addisoniae	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	3
Ki	1
MIC	8

Activity Type	# Activity
Individual Protein	4
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	20600.0	nM	PMID[536313]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	26.44	ug.mL-1	PMID[536315]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	Ki	=	27.49	ug ml-1	PMID[536315]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	24.56	ug.mL-1	PMID[536315]
NPT771	Organism	Penicillium crustosum	Penicillium crustosum	MIC	>	100.0	ug.mL-1	PMID[536314]
NPT769	Organism	Mucor mucedo	Mucor mucedo	MIC	>	100.0	ug.mL-1	PMID[536314]
NPT767	Organism	Pichia jadinii	Cyberlindnera jadinii	MIC	>	100.0	ug.mL-1	PMID[536314]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	100.0	ug.mL-1	PMID[536314]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[536314]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[536314]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[536314]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[536314]

☑ 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 NPC190043 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	319
0.1-0.2	1493
0.2-0.3	3884
0.3-0.4	11337
0.4-0.5	7739
0.5-0.6	5067
0.6-0.7	6655
0.7-0.8	4659
0.8-0.85	994
0.85-0.9	406
0.9-0.95	109
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC30501
1.0	High Similarity	NPC100067
1.0	High Similarity	NPC162612
1.0	High Similarity	NPC266689
1.0	High Similarity	NPC98254
1.0	High Similarity	NPC23126
1.0	High Similarity	NPC105157
1.0	High Similarity	NPC72158
1.0	High Similarity	NPC169250
1.0	High Similarity	NPC103356
0.9917	High Similarity	NPC62952
0.9917	High Similarity	NPC21305
0.9917	High Similarity	NPC267846
0.9917	High Similarity	NPC221777
0.9917	High Similarity	NPC473017
0.9836	High Similarity	NPC474998
0.9835	High Similarity	NPC116513
0.9677	High Similarity	NPC475042
0.9583	High Similarity	NPC133909
0.9583	High Similarity	NPC91105
0.9583	High Similarity	NPC309765
0.9583	High Similarity	NPC32032
0.9524	High Similarity	NPC213485
0.9524	High Similarity	NPC40524
0.9524	High Similarity	NPC139074
0.9516	High Similarity	NPC476119
0.9504	High Similarity	NPC65761
0.9504	High Similarity	NPC472029
0.95	High Similarity	NPC224273
0.95	High Similarity	NPC143427
0.95	High Similarity	NPC196976
0.95	High Similarity	NPC45438
0.95	High Similarity	NPC156139
0.95	High Similarity	NPC303737
0.95	High Similarity	NPC215392
0.95	High Similarity	NPC242895
0.95	High Similarity	NPC115159
0.95	High Similarity	NPC19174
0.95	High Similarity	NPC267552
0.95	High Similarity	NPC73532
0.9449	High Similarity	NPC282780
0.9449	High Similarity	NPC166480
0.9417	High Similarity	NPC149246
0.9417	High Similarity	NPC297186
0.9375	High Similarity	NPC70859
0.9375	High Similarity	NPC61153
0.9375	High Similarity	NPC470210
0.9375	High Similarity	NPC283590
0.9375	High Similarity	NPC130899
0.9365	High Similarity	NPC275504
0.935	High Similarity	NPC475733
0.9333	High Similarity	NPC159525
0.9302	High Similarity	NPC131039
0.9302	High Similarity	NPC194764
0.9302	High Similarity	NPC65005
0.9302	High Similarity	NPC264112
0.9291	High Similarity	NPC175738
0.9274	High Similarity	NPC8745
0.9268	High Similarity	NPC13238
0.9256	High Similarity	NPC229649
0.925	High Similarity	NPC158222
0.925	High Similarity	NPC195262
0.925	High Similarity	NPC161617
0.925	High Similarity	NPC188814
0.9231	High Similarity	NPC150399
0.9231	High Similarity	NPC1486
0.9231	High Similarity	NPC274109
0.9231	High Similarity	NPC186838
0.9231	High Similarity	NPC168105
0.9231	High Similarity	NPC12165
0.9231	High Similarity	NPC477242
0.9231	High Similarity	NPC66349
0.9231	High Similarity	NPC98115
0.9231	High Similarity	NPC41461
0.9231	High Similarity	NPC477244
0.9231	High Similarity	NPC25287
0.9231	High Similarity	NPC477243
0.9231	High Similarity	NPC249606
0.9206	High Similarity	NPC109123
0.9206	High Similarity	NPC92624
0.9194	High Similarity	NPC10926
0.918	High Similarity	NPC226275
0.9174	High Similarity	NPC294037
0.9167	High Similarity	NPC40649
0.9167	High Similarity	NPC209486
0.916	High Similarity	NPC472419
0.916	High Similarity	NPC317119
0.916	High Similarity	NPC153979
0.9154	High Similarity	NPC13575
0.9154	High Similarity	NPC156092
0.9147	High Similarity	NPC475088
0.9134	High Similarity	NPC259942
0.9106	High Similarity	NPC232708
0.9098	High Similarity	NPC146642
0.9091	High Similarity	NPC19622
0.9091	High Similarity	NPC112789
0.9091	High Similarity	NPC21350
0.9091	High Similarity	NPC138099
0.9091	High Similarity	NPC242994
0.9084	High Similarity	NPC474110
0.9084	High Similarity	NPC44960
0.9083	High Similarity	NPC121259
0.9077	High Similarity	NPC286336
0.9077	High Similarity	NPC103842
0.9055	High Similarity	NPC102829
0.9055	High Similarity	NPC120488
0.9023	High Similarity	NPC275903
0.9023	High Similarity	NPC169452
0.9023	High Similarity	NPC470211
0.9023	High Similarity	NPC472366
0.9023	High Similarity	NPC181560
0.9023	High Similarity	NPC477956
0.9008	High Similarity	NPC118919
0.9008	High Similarity	NPC191976
0.9	High Similarity	NPC312318
0.9	High Similarity	NPC294593
0.9	High Similarity	NPC139813
0.9	High Similarity	NPC263670
0.9	High Similarity	NPC159623
0.9	High Similarity	NPC175098
0.9	High Similarity	NPC28753
0.9	High Similarity	NPC337373
0.9	High Similarity	NPC20560
0.9	High Similarity	NPC242294
0.9	High Similarity	NPC204960
0.9	High Similarity	NPC192304
0.9	High Similarity	NPC82225
0.9	High Similarity	NPC472365
0.9	High Similarity	NPC144051
0.9	High Similarity	NPC56031
0.9	High Similarity	NPC27643
0.9	High Similarity	NPC188646
0.9	High Similarity	NPC18877
0.8992	High Similarity	NPC262359
0.8968	High Similarity	NPC328983
0.8955	High Similarity	NPC261227
0.8955	High Similarity	NPC204985
0.8955	High Similarity	NPC172250
0.8955	High Similarity	NPC215311
0.8955	High Similarity	NPC172986
0.8955	High Similarity	NPC213659
0.8955	High Similarity	NPC48624
0.8955	High Similarity	NPC235239
0.8955	High Similarity	NPC259166
0.8955	High Similarity	NPC144118
0.8955	High Similarity	NPC270883
0.8955	High Similarity	NPC80962
0.8955	High Similarity	NPC326109
0.8955	High Similarity	NPC69769
0.8955	High Similarity	NPC219917
0.8955	High Similarity	NPC11056
0.8947	High Similarity	NPC243528
0.8947	High Similarity	NPC471620
0.8947	High Similarity	NPC251681
0.8943	High Similarity	NPC248363
0.8939	High Similarity	NPC290030
0.8939	High Similarity	NPC53206
0.8939	High Similarity	NPC53414
0.8939	High Similarity	NPC213603
0.8939	High Similarity	NPC471905
0.8923	High Similarity	NPC87231
0.8923	High Similarity	NPC129132
0.8923	High Similarity	NPC205468
0.8923	High Similarity	NPC267205
0.8923	High Similarity	NPC257756
0.8923	High Similarity	NPC212631
0.8898	High Similarity	NPC329205
0.8898	High Similarity	NPC316625
0.8889	High Similarity	NPC118840
0.8889	High Similarity	NPC26051
0.8889	High Similarity	NPC193555
0.8889	High Similarity	NPC470087
0.8889	High Similarity	NPC205006
0.8889	High Similarity	NPC147688
0.8889	High Similarity	NPC52789
0.8889	High Similarity	NPC469404
0.8889	High Similarity	NPC64908
0.8889	High Similarity	NPC321980
0.8889	High Similarity	NPC268204
0.8889	High Similarity	NPC470089
0.8889	High Similarity	NPC477454
0.8889	High Similarity	NPC55832
0.8889	High Similarity	NPC156590
0.8889	High Similarity	NPC110969
0.8881	High Similarity	NPC220062
0.8881	High Similarity	NPC301217
0.8881	High Similarity	NPC283429
0.8881	High Similarity	NPC55018
0.8881	High Similarity	NPC295384
0.8881	High Similarity	NPC96565
0.8881	High Similarity	NPC303633
0.8881	High Similarity	NPC216978
0.8872	High Similarity	NPC473622
0.8864	High Similarity	NPC254847
0.8855	High Similarity	NPC44437
0.8846	High Similarity	NPC112192
0.8846	High Similarity	NPC308037
0.8846	High Similarity	NPC135801
0.8846	High Similarity	NPC66384
0.8846	High Similarity	NPC64359

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 NPC190043 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	956
0.2-0.3	1348
0.3-0.4	2754
0.4-0.5	2143
0.5-0.6	1151
0.6-0.7	364
0.7-0.8	109
0.8-0.85	14
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8864	High Similarity	NPD1509	Clinical (unspecified phase)
0.8846	High Similarity	NPD943	Approved
0.8846	High Similarity	NPD1240	Approved
0.8712	High Similarity	NPD1607	Approved
0.8582	High Similarity	NPD1510	Phase 2
0.8561	High Similarity	NPD7410	Clinical (unspecified phase)
0.8561	High Similarity	NPD4378	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD7390	Discontinued
0.8394	Intermediate Similarity	NPD1549	Phase 2
0.8321	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD1164	Approved
0.8264	Intermediate Similarity	NPD4380	Phase 2
0.8207	Intermediate Similarity	NPD7411	Suspended
0.8189	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD1470	Approved
0.814	Intermediate Similarity	NPD1201	Approved
0.8116	Intermediate Similarity	NPD5406	Approved
0.8116	Intermediate Similarity	NPD5405	Approved
0.8116	Intermediate Similarity	NPD5404	Approved
0.8116	Intermediate Similarity	NPD2796	Approved
0.8116	Intermediate Similarity	NPD2935	Discontinued
0.8116	Intermediate Similarity	NPD5408	Approved
0.8095	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD7075	Discontinued
0.8043	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD6651	Approved
0.7973	Intermediate Similarity	NPD7819	Suspended
0.7973	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD6799	Approved
0.7905	Intermediate Similarity	NPD6801	Discontinued
0.7886	Intermediate Similarity	NPD74	Approved
0.7886	Intermediate Similarity	NPD9266	Approved
0.7847	Intermediate Similarity	NPD1511	Approved
0.7833	Intermediate Similarity	NPD846	Approved
0.7833	Intermediate Similarity	NPD940	Approved
0.7817	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD2800	Approved
0.7812	Intermediate Similarity	NPD9493	Approved
0.7805	Intermediate Similarity	NPD9264	Approved
0.7805	Intermediate Similarity	NPD9267	Approved
0.7805	Intermediate Similarity	NPD9263	Approved
0.7805	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD2799	Discontinued
0.7785	Intermediate Similarity	NPD1934	Approved
0.777	Intermediate Similarity	NPD6599	Discontinued
0.7762	Intermediate Similarity	NPD3750	Approved
0.7748	Intermediate Similarity	NPD7768	Phase 2
0.7748	Intermediate Similarity	NPD3882	Suspended
0.7746	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1512	Approved
0.7733	Intermediate Similarity	NPD2801	Approved
0.7697	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1243	Approved
0.7676	Intermediate Similarity	NPD2344	Approved
0.7674	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1203	Approved
0.7613	Intermediate Similarity	NPD6232	Discontinued
0.7609	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1551	Phase 2
0.7582	Intermediate Similarity	NPD3749	Approved
0.758	Intermediate Similarity	NPD7473	Discontinued
0.7574	Intermediate Similarity	NPD2798	Approved
0.7557	Intermediate Similarity	NPD9545	Approved
0.7551	Intermediate Similarity	NPD2532	Approved
0.7551	Intermediate Similarity	NPD2533	Approved
0.7551	Intermediate Similarity	NPD2534	Approved
0.7548	Intermediate Similarity	NPD6959	Discontinued
0.7537	Intermediate Similarity	NPD9269	Phase 2
0.7519	Intermediate Similarity	NPD9281	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD9268	Approved
0.7484	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7286	Phase 2
0.7482	Intermediate Similarity	NPD2313	Discontinued
0.748	Intermediate Similarity	NPD9261	Approved
0.7466	Intermediate Similarity	NPD2309	Approved
0.745	Intermediate Similarity	NPD920	Approved
0.7417	Intermediate Similarity	NPD2860	Approved
0.7417	Intermediate Similarity	NPD2859	Approved
0.7415	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3748	Approved
0.7407	Intermediate Similarity	NPD9717	Approved
0.7407	Intermediate Similarity	NPD3972	Approved
0.7405	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6166	Phase 2
0.7405	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6020	Phase 2
0.7372	Intermediate Similarity	NPD5494	Approved
0.7357	Intermediate Similarity	NPD3764	Approved
0.7338	Intermediate Similarity	NPD3817	Phase 2
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD2933	Approved
0.7333	Intermediate Similarity	NPD2934	Approved
0.7333	Intermediate Similarity	NPD5403	Approved
0.7329	Intermediate Similarity	NPD2654	Approved
0.7324	Intermediate Similarity	NPD230	Phase 1
0.7317	Intermediate Similarity	NPD1242	Phase 1
0.7315	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3818	Discontinued
0.7301	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4750	Phase 3
0.7239	Intermediate Similarity	NPD6559	Discontinued
0.7237	Intermediate Similarity	NPD3226	Approved
0.7236	Intermediate Similarity	NPD3020	Approved
0.7234	Intermediate Similarity	NPD3268	Approved
0.7222	Intermediate Similarity	NPD7074	Phase 3
0.7206	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5401	Approved
0.7192	Intermediate Similarity	NPD2346	Discontinued
0.7188	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3019	Approved
0.7185	Intermediate Similarity	NPD2932	Approved
0.7181	Intermediate Similarity	NPD3300	Phase 2
0.7179	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4628	Phase 3
0.716	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD1237	Approved
0.7124	Intermediate Similarity	NPD7458	Discontinued
0.7123	Intermediate Similarity	NPD6099	Approved
0.7123	Intermediate Similarity	NPD6100	Approved
0.7122	Intermediate Similarity	NPD2797	Approved
0.7117	Intermediate Similarity	NPD7472	Approved
0.7113	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD919	Approved
0.708	Intermediate Similarity	NPD422	Phase 1
0.7073	Intermediate Similarity	NPD6797	Phase 2
0.7063	Intermediate Similarity	NPD520	Approved
0.7063	Intermediate Similarity	NPD1929	Approved
0.7063	Intermediate Similarity	NPD1930	Approved
0.7063	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5844	Phase 1
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7047	Intermediate Similarity	NPD7003	Approved
0.7047	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3400	Discontinued
0.703	Intermediate Similarity	NPD7251	Discontinued
0.7019	Intermediate Similarity	NPD3926	Phase 2
0.7012	Intermediate Similarity	NPD1729	Discontinued
0.7006	Intermediate Similarity	NPD5402	Approved
0.7006	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1247	Approved
0.6992	Remote Similarity	NPD5951	Approved
0.6992	Remote Similarity	NPD1809	Phase 2
0.6988	Remote Similarity	NPD7808	Phase 3
0.6972	Remote Similarity	NPD4908	Phase 1
0.6967	Remote Similarity	NPD845	Approved
0.6957	Remote Similarity	NPD5710	Approved
0.6957	Remote Similarity	NPD5711	Approved
0.6939	Remote Similarity	NPD7033	Discontinued
0.6939	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1876	Approved
0.6912	Remote Similarity	NPD1548	Phase 1
0.6899	Remote Similarity	NPD2296	Approved
0.6897	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3266	Approved
0.6879	Remote Similarity	NPD4360	Phase 2
0.6879	Remote Similarity	NPD3267	Approved
0.6879	Remote Similarity	NPD4363	Phase 3
0.6875	Remote Similarity	NPD411	Approved
0.687	Remote Similarity	NPD3022	Approved
0.687	Remote Similarity	NPD3021	Approved
0.6849	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD447	Suspended
0.6849	Remote Similarity	NPD1933	Approved
0.6846	Remote Similarity	NPD1471	Phase 3
0.6839	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4361	Phase 2
0.6835	Remote Similarity	NPD1465	Phase 2
0.6835	Remote Similarity	NPD1610	Phase 2
0.6831	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5048	Discontinued
0.6821	Remote Similarity	NPD1196	Approved
0.6818	Remote Similarity	NPD5049	Phase 3
0.6815	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3225	Approved
0.6806	Remote Similarity	NPD4625	Phase 3
0.6797	Remote Similarity	NPD1543	Discontinued
0.6792	Remote Similarity	NPD4288	Approved
0.6791	Remote Similarity	NPD1241	Discontinued
0.6788	Remote Similarity	NPD1759	Phase 1
0.6786	Remote Similarity	NPD1608	Approved
0.6781	Remote Similarity	NPD4307	Phase 2
0.678	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2354	Approved
0.6776	Remote Similarity	NPD6190	Approved
0.6774	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3023	Approved
0.6763	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3026	Approved
0.6759	Remote Similarity	NPD1296	Phase 2
0.6755	Remote Similarity	NPD1195	Approved
0.6752	Remote Similarity	NPD6585	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