NPASS Compound

Structure

NPC304954 OpenBabel07101718322D 21 23 0 0 0 0 0 0 0 0999 V2000 -4.4347 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9781 -1.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 5 2 0 0 0 0 2 9 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.07
Volume:	282.482
LogP:	2.608
LogD:	2.608
LogS:	-3.551
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.829
Synthetic Accessibility Score:	2.25
Fsp3:	0.062
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:	-4.987
MDCK Permeability:	1.8934822946903296e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	99.57794952392578%
Volume Distribution (VD):	0.49
Pgp-substrate:	1.1812100410461426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.63
CYP2C19-inhibitor:	0.722
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.693
CYP2C9-substrate:	0.806
CYP2D6-inhibitor:	0.531
CYP2D6-substrate:	0.678
CYP3A4-inhibitor:	0.834
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	9.713
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.509
AMES Toxicity:	0.691
Rat Oral Acute Toxicity:	0.829
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.763
Carcinogencity:	0.872
Eye Corrosion:	0.004
Eye Irritation:	0.932
Respiratory Toxicity:	0.564

Download Data

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

Natural Product: NPC304954

Natural Product ID:	NPC304954
*Common Name:**	Sid26657808
IUPAC Name:	(2Z)-6-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-1-benzofuran-3-one
Synonyms:
Standard InCHIKey:	HPSPCMSCDNHZJM-CHHVJCJISA-N
Standard InCHI:	InChI=1S/C16H12O5/c1-20-14-6-9(2-5-12(14)18)7-15-16(19)11-4-3-10(17)8-13(11)21-15/h2-8,17-18H,1H3/b15-7-
SMILES:	COc1cc(ccc1O)/C=C/1Oc2c(C1=O)ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446827
PubChem CID:	16376440
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001631] Aurone flavonoids

*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
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[12762787]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762809]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5140	Dipteryx odorata	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
AC50	1
IC50	3
Others	3
Potency	46

Activity Type	# Activity
Cell Line	1
Individual Protein	36
NON-MOLECULAR	1
Organism	2
Others	9
PROTEIN COMPLEX	3
Protein-Protein Interaction	1
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	6.4	uM	PMID[475739]
NPT45	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	11220.2	nM	PMID[475740]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	28183.8	nM	PMID[475740]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	25118.9	nM	PMID[475740]
NPT1038	Individual Protein	Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	70794.6	nM	PMID[475740]
NPT537	Individual Protein	Ras-related protein Rab-9A	Homo sapiens	Potency	=	3981.1	nM	PMID[475740]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	2511.9	nM	PMID[475740]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	31622.8	nM	PMID[475740]
NPT538	Individual Protein	Niemann-Pick C1 protein	Homo sapiens	Potency	=	3162.3	nM	PMID[475740]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	50118.7	nM	PMID[475740]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	79432.8	nM	PMID[475740]
NPT1005	Individual Protein	Tumor susceptibility gene 101 protein	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[475740]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[475740]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[475740]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	23099.9	nM	PMID[475740]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	16353.5	nM	PMID[475740]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[475740]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[475740]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	794.3	nM	PMID[475740]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	8492.1	nM	PMID[475740]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[475740]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[475740]
NPT1852	Individual Protein	Rac GTPase-activating protein 1	Homo sapiens	IC50	n.a.	26050.0	nM	PMID[475740]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	18887.6	nM	PMID[475740]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	2818.4	nM	PMID[475740]
NPT157	Individual Protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[475740]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[475740]
NPT1417	Individual Protein	Transcriptional regulator ERG	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[475740]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[475740]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[475740]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[475740]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[475740]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34600.0	nM	PMID[475739]
NPT2	Others	Unspecified		Ratio	=	5.4	n.a.	PMID[475739]
NPT2	Others	Unspecified		Inhibition	=	48.2	%	PMID[475739]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	19952.6	nM	PMID[475740]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	5211.9	nM	PMID[475740]
NPT2	Others	Unspecified		Potency	=	16360.1	nM	PMID[475740]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18.5	nM	PMID[475740]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	366.3	nM	PMID[475740]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	1995.3	nM	PMID[475740]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[475740]
NPT84	Individual Protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Rattus norvegicus	AC50	=	641.0	nM	PMID[475740]
NPT2	Others	Unspecified		Potency	n.a.	6309.6	nM	PMID[475740]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	5221.3	nM	PMID[475740]
NPT2	Others	Unspecified		Potency	n.a.	3548.1	nM	PMID[475740]
NPT2	Others	Unspecified		IC50	n.a.	33860.0	nM	PMID[475740]
NPT821	Individual Protein	Werner syndrome ATP-dependent helicase	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[475740]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[475740]
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PMID[475740]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[475740]
NPT2	Others	Unspecified		Potency	n.a.	5623.4	nM	PMID[475740]

☑ 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 NPC304954 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	408
0.1-0.2	1802
0.2-0.3	4962
0.3-0.4	11310
0.4-0.5	6053
0.5-0.6	3601
0.6-0.7	5082
0.7-0.8	5573
0.8-0.85	2358
0.85-0.9	1148
0.9-0.95	386
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC260582
0.9667	High Similarity	NPC195832
0.9655	High Similarity	NPC140840
0.9655	High Similarity	NPC86847
0.9595	High Similarity	NPC55205
0.9595	High Similarity	NPC279989
0.9595	High Similarity	NPC82325
0.9589	High Similarity	NPC19545
0.9533	High Similarity	NPC265511
0.953	High Similarity	NPC189130
0.953	High Similarity	NPC236223
0.953	High Similarity	NPC78326
0.953	High Similarity	NPC179126
0.953	High Similarity	NPC270620
0.9527	High Similarity	NPC125062
0.9527	High Similarity	NPC252933
0.9527	High Similarity	NPC54394
0.9527	High Similarity	NPC260895
0.9527	High Similarity	NPC200740
0.9477	High Similarity	NPC272722
0.9463	High Similarity	NPC123886
0.9459	High Similarity	NPC188871
0.9459	High Similarity	NPC149127
0.9459	High Similarity	NPC286342
0.9404	High Similarity	NPC266960
0.9404	High Similarity	NPC245546
0.9404	High Similarity	NPC43243
0.94	High Similarity	NPC162351
0.94	High Similarity	NPC58382
0.9396	High Similarity	NPC133953
0.9396	High Similarity	NPC31363
0.9396	High Similarity	NPC236769
0.9396	High Similarity	NPC28274
0.9396	High Similarity	NPC50403
0.9392	High Similarity	NPC87125
0.9392	High Similarity	NPC270465
0.9392	High Similarity	NPC159103
0.9392	High Similarity	NPC137062
0.9392	High Similarity	NPC183950
0.9392	High Similarity	NPC223579
0.9392	High Similarity	NPC52005
0.9392	High Similarity	NPC287101
0.9388	High Similarity	NPC117463
0.9379	High Similarity	NPC254659
0.9355	High Similarity	NPC36320
0.9346	High Similarity	NPC269906
0.9342	High Similarity	NPC176665
0.9342	High Similarity	NPC305663
0.9342	High Similarity	NPC67876
0.9342	High Similarity	NPC101830
0.9342	High Similarity	NPC163524
0.9342	High Similarity	NPC471479
0.9342	High Similarity	NPC110070
0.9342	High Similarity	NPC287979
0.9342	High Similarity	NPC203891
0.9342	High Similarity	NPC52530
0.9342	High Similarity	NPC471515
0.9338	High Similarity	NPC44079
0.9338	High Similarity	NPC26227
0.9338	High Similarity	NPC201451
0.9333	High Similarity	NPC60972
0.9333	High Similarity	NPC477231
0.9333	High Similarity	NPC39732
0.9333	High Similarity	NPC257648
0.9329	High Similarity	NPC50728
0.9329	High Similarity	NPC29231
0.9329	High Similarity	NPC166753
0.9324	High Similarity	NPC120464
0.9315	High Similarity	NPC142165
0.931	High Similarity	NPC284556
0.931	High Similarity	NPC301178
0.929	High Similarity	NPC59295
0.929	High Similarity	NPC39305
0.929	High Similarity	NPC1706
0.929	High Similarity	NPC1755
0.929	High Similarity	NPC472582
0.929	High Similarity	NPC263092
0.9281	High Similarity	NPC288669
0.9281	High Similarity	NPC18772
0.9281	High Similarity	NPC7846
0.9281	High Similarity	NPC105242
0.9281	High Similarity	NPC9609
0.9281	High Similarity	NPC204854
0.9281	High Similarity	NPC115798
0.9281	High Similarity	NPC191459
0.9281	High Similarity	NPC176300
0.9281	High Similarity	NPC193842
0.9281	High Similarity	NPC253634
0.9281	High Similarity	NPC130894
0.9281	High Similarity	NPC152166
0.9281	High Similarity	NPC25495
0.9281	High Similarity	NPC300943
0.9281	High Similarity	NPC143828
0.9281	High Similarity	NPC261004
0.9281	High Similarity	NPC55738
0.9281	High Similarity	NPC4481
0.9281	High Similarity	NPC19687
0.9281	High Similarity	NPC18607
0.9281	High Similarity	NPC22472
0.9276	High Similarity	NPC474638
0.9276	High Similarity	NPC55619
0.9276	High Similarity	NPC292107
0.9276	High Similarity	NPC247017
0.9276	High Similarity	NPC200388
0.9276	High Similarity	NPC472461
0.9276	High Similarity	NPC320825
0.9276	High Similarity	NPC326037
0.9276	High Similarity	NPC100916
0.9276	High Similarity	NPC49824
0.9276	High Similarity	NPC471500
0.9276	High Similarity	NPC13858
0.9276	High Similarity	NPC98661
0.9272	High Similarity	NPC141212
0.9272	High Similarity	NPC469550
0.9267	High Similarity	NPC76376
0.9262	High Similarity	NPC177298
0.9262	High Similarity	NPC48479
0.9257	High Similarity	NPC12200
0.9257	High Similarity	NPC108406
0.9257	High Similarity	NPC168803
0.9257	High Similarity	NPC51443
0.9257	High Similarity	NPC74881
0.9257	High Similarity	NPC95864
0.9247	High Similarity	NPC119663
0.9247	High Similarity	NPC471417
0.9241	High Similarity	NPC110419
0.9231	High Similarity	NPC45449
0.9226	High Similarity	NPC238995
0.9216	High Similarity	NPC472438
0.9216	High Similarity	NPC7973
0.9216	High Similarity	NPC227192
0.9216	High Similarity	NPC75215
0.9216	High Similarity	NPC189179
0.9216	High Similarity	NPC29841
0.9216	High Similarity	NPC174908
0.9216	High Similarity	NPC235215
0.9216	High Similarity	NPC78302
0.9216	High Similarity	NPC93376
0.9216	High Similarity	NPC224137
0.9211	High Similarity	NPC32557
0.9211	High Similarity	NPC168247
0.9211	High Similarity	NPC80534
0.9211	High Similarity	NPC56786
0.9211	High Similarity	NPC20830
0.9211	High Similarity	NPC133392
0.9211	High Similarity	NPC189960
0.9211	High Similarity	NPC234255
0.9211	High Similarity	NPC214138
0.9211	High Similarity	NPC256612
0.9211	High Similarity	NPC117992
0.9211	High Similarity	NPC57674
0.9211	High Similarity	NPC152951
0.9211	High Similarity	NPC230149
0.9211	High Similarity	NPC2928
0.9205	High Similarity	NPC188203
0.9205	High Similarity	NPC472912
0.9205	High Similarity	NPC275722
0.9205	High Similarity	NPC57030
0.9205	High Similarity	NPC222830
0.9205	High Similarity	NPC120163
0.9205	High Similarity	NPC260979
0.9205	High Similarity	NPC198826
0.9205	High Similarity	NPC212678
0.9205	High Similarity	NPC100887
0.9205	High Similarity	NPC301323
0.9205	High Similarity	NPC83508
0.9205	High Similarity	NPC25270
0.9205	High Similarity	NPC71334
0.9205	High Similarity	NPC236637
0.9205	High Similarity	NPC156222
0.9205	High Similarity	NPC301123
0.9205	High Similarity	NPC275836
0.9205	High Similarity	NPC239128
0.9205	High Similarity	NPC131624
0.9205	High Similarity	NPC219582
0.9205	High Similarity	NPC256283
0.9205	High Similarity	NPC162313
0.9205	High Similarity	NPC302950
0.9205	High Similarity	NPC293183
0.9205	High Similarity	NPC241498
0.9205	High Similarity	NPC187498
0.92	High Similarity	NPC219330
0.9195	High Similarity	NPC80710
0.9195	High Similarity	NPC195202
0.9195	High Similarity	NPC139364
0.9195	High Similarity	NPC203747
0.9195	High Similarity	NPC196277
0.9195	High Similarity	NPC254702
0.9195	High Similarity	NPC194653
0.9195	High Similarity	NPC261548
0.9195	High Similarity	NPC43669
0.9195	High Similarity	NPC272721
0.9189	High Similarity	NPC179271
0.9189	High Similarity	NPC20791
0.9178	High Similarity	NPC312256
0.9161	High Similarity	NPC308992
0.9161	High Similarity	NPC188486
0.9156	High Similarity	NPC16935
0.9156	High Similarity	NPC196879
0.915	High Similarity	NPC472455

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 NPC304954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	979
0.2-0.3	1806
0.3-0.4	2665
0.4-0.5	1709
0.5-0.6	1001
0.6-0.7	436
0.7-0.8	132
0.8-0.85	30
0.85-0.9	11
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9797	High Similarity	NPD3882	Suspended
0.9205	High Similarity	NPD1934	Approved
0.9189	High Similarity	NPD1512	Approved
0.9145	High Similarity	NPD2801	Approved
0.9054	High Similarity	NPD1511	Approved
0.8961	High Similarity	NPD3817	Phase 2
0.8896	High Similarity	NPD2393	Clinical (unspecified phase)
0.8868	High Similarity	NPD6168	Clinical (unspecified phase)
0.8868	High Similarity	NPD6166	Phase 2
0.8868	High Similarity	NPD6167	Clinical (unspecified phase)
0.88	High Similarity	NPD6799	Approved
0.8758	High Similarity	NPD3818	Discontinued
0.8618	High Similarity	NPD4378	Clinical (unspecified phase)
0.8608	High Similarity	NPD7075	Discontinued
0.8598	High Similarity	NPD6797	Phase 2
0.8553	High Similarity	NPD919	Approved
0.8545	High Similarity	NPD7251	Discontinued
0.8535	High Similarity	NPD7096	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD7808	Phase 3
0.8493	Intermediate Similarity	NPD1240	Approved
0.8476	Intermediate Similarity	NPD7054	Approved
0.8467	Intermediate Similarity	NPD1549	Phase 2
0.8462	Intermediate Similarity	NPD6599	Discontinued
0.8457	Intermediate Similarity	NPD3926	Phase 2
0.8447	Intermediate Similarity	NPD1247	Approved
0.8424	Intermediate Similarity	NPD7472	Approved
0.8424	Intermediate Similarity	NPD7074	Phase 3
0.84	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1510	Phase 2
0.8385	Intermediate Similarity	NPD5494	Approved
0.8378	Intermediate Similarity	NPD1607	Approved
0.8367	Intermediate Similarity	NPD943	Approved
0.8354	Intermediate Similarity	NPD6801	Discontinued
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD4380	Phase 2
0.8212	Intermediate Similarity	NPD2796	Approved
0.8153	Intermediate Similarity	NPD5403	Approved
0.8148	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD5401	Approved
0.8141	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5402	Approved
0.8105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1465	Phase 2
0.8075	Intermediate Similarity	NPD7819	Suspended
0.8061	Intermediate Similarity	NPD6232	Discontinued
0.8047	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7473	Discontinued
0.7974	Intermediate Similarity	NPD1551	Phase 2
0.795	Intermediate Similarity	NPD7411	Suspended
0.7947	Intermediate Similarity	NPD230	Phase 1
0.7947	Intermediate Similarity	NPD447	Suspended
0.7935	Intermediate Similarity	NPD2800	Approved
0.7927	Intermediate Similarity	NPD3749	Approved
0.7922	Intermediate Similarity	NPD2344	Approved
0.7914	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6559	Discontinued
0.7885	Intermediate Similarity	NPD3750	Approved
0.7852	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD5844	Phase 1
0.7821	Intermediate Similarity	NPD1243	Approved
0.7785	Intermediate Similarity	NPD9494	Approved
0.7785	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1613	Approved
0.7763	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2935	Discontinued
0.7736	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2309	Approved
0.7712	Intermediate Similarity	NPD1933	Approved
0.7702	Intermediate Similarity	NPD920	Approved
0.7688	Intermediate Similarity	NPD2534	Approved
0.7688	Intermediate Similarity	NPD2532	Approved
0.7688	Intermediate Similarity	NPD2533	Approved
0.7682	Intermediate Similarity	NPD3027	Phase 3
0.7679	Intermediate Similarity	NPD7199	Phase 2
0.7679	Intermediate Similarity	NPD6959	Discontinued
0.7673	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3751	Discontinued
0.7658	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7651	Intermediate Similarity	NPD1203	Approved
0.7651	Intermediate Similarity	NPD7768	Phase 2
0.7647	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6190	Approved
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3748	Approved
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1471	Phase 3
0.7457	Intermediate Similarity	NPD2163	Approved
0.7456	Intermediate Similarity	NPD6234	Discontinued
0.7452	Intermediate Similarity	NPD2799	Discontinued
0.7452	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD9717	Approved
0.7443	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD2403	Approved
0.7436	Intermediate Similarity	NPD6651	Approved
0.7429	Intermediate Similarity	NPD5953	Discontinued
0.7427	Intermediate Similarity	NPD3787	Discontinued
0.7405	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6099	Approved
0.7405	Intermediate Similarity	NPD6100	Approved
0.7394	Intermediate Similarity	NPD3226	Approved
0.7391	Intermediate Similarity	NPD2354	Approved
0.7386	Intermediate Similarity	NPD6832	Phase 2
0.7375	Intermediate Similarity	NPD2654	Approved
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6355	Discontinued
0.7337	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9269	Phase 2
0.7333	Intermediate Similarity	NPD1653	Approved
0.7314	Intermediate Similarity	NPD7286	Phase 2
0.7308	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4357	Discontinued
0.7293	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6798	Discontinued
0.729	Intermediate Similarity	NPD411	Approved
0.729	Intermediate Similarity	NPD2313	Discontinued
0.7279	Intermediate Similarity	NPD5536	Phase 2
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7267	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7262	Intermediate Similarity	NPD37	Approved
0.725	Intermediate Similarity	NPD2346	Discontinued
0.7235	Intermediate Similarity	NPD4965	Approved
0.7235	Intermediate Similarity	NPD4967	Phase 2
0.7235	Intermediate Similarity	NPD4966	Approved
0.723	Intermediate Similarity	NPD1548	Phase 1
0.7222	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1608	Approved
0.7208	Intermediate Similarity	NPD3018	Phase 2
0.7197	Intermediate Similarity	NPD4060	Phase 1
0.7191	Intermediate Similarity	NPD7685	Pre-registration
0.7184	Intermediate Similarity	NPD5242	Approved
0.7176	Intermediate Similarity	NPD2296	Approved
0.7161	Intermediate Similarity	NPD4908	Phase 1
0.7159	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD1610	Phase 2
0.7143	Intermediate Similarity	NPD2353	Approved
0.7143	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7126	Intermediate Similarity	NPD5710	Approved
0.7126	Intermediate Similarity	NPD5711	Approved
0.7125	Intermediate Similarity	NPD7033	Discontinued
0.7125	Intermediate Similarity	NPD4308	Phase 3
0.7114	Intermediate Similarity	NPD9545	Approved
0.7108	Intermediate Similarity	NPD5049	Phase 3
0.7103	Intermediate Similarity	NPD228	Approved
0.7101	Intermediate Similarity	NPD6386	Approved
0.7101	Intermediate Similarity	NPD6385	Approved
0.7095	Intermediate Similarity	NPD9493	Approved
0.7091	Intermediate Similarity	NPD7390	Discontinued
0.7079	Intermediate Similarity	NPD1729	Discontinued
0.7076	Intermediate Similarity	NPD5353	Approved
0.7073	Intermediate Similarity	NPD3887	Approved
0.707	Intermediate Similarity	NPD3268	Approved
0.707	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3764	Approved
0.7067	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD2982	Phase 2
0.7059	Intermediate Similarity	NPD2983	Phase 2
0.7048	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3146	Approved
0.7048	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4062	Phase 3
0.702	Intermediate Similarity	NPD17	Approved
0.7013	Intermediate Similarity	NPD3225	Approved
0.7011	Intermediate Similarity	NPD4287	Approved
0.7007	Intermediate Similarity	NPD1241	Discontinued
0.7006	Intermediate Similarity	NPD7095	Approved
0.7005	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4361	Phase 2
0.6994	Remote Similarity	NPD6971	Discontinued
0.6993	Remote Similarity	NPD3972	Approved
0.6993	Remote Similarity	NPD2981	Phase 2
0.6981	Remote Similarity	NPD1558	Phase 1
0.6977	Remote Similarity	NPD4288	Approved
0.6968	Remote Similarity	NPD2797	Approved
0.6968	Remote Similarity	NPD1470	Approved
0.6947	Remote Similarity	NPD6782	Approved
0.6947	Remote Similarity	NPD6778	Approved
0.6947	Remote Similarity	NPD6777	Approved
0.6947	Remote Similarity	NPD6780	Approved
0.6947	Remote Similarity	NPD6776	Approved
0.6947	Remote Similarity	NPD6779	Approved
0.6947	Remote Similarity	NPD6781	Approved
0.6946	Remote Similarity	NPD4661	Approved
0.6946	Remote Similarity	NPD4662	Approved
0.6933	Remote Similarity	NPD2343	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data