NPASS Compound

Structure

CID77955 OpenBabel06191715412D 21 23 0 0 0 0 0 0 0 0999 V2000 -5.1962 -1.0000 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 2.5981 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 1.7321 2.0000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -0.8660 1.5000 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 0.8660 1.5000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 19 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 12 2 0 0 0 0 6 14 2 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 18 2 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	282.09
Volume:	290.988
LogP:	3.495
LogD:	2.978
LogS:	-5.167
# Rotatable Bonds:	3
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	1.828
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.636
MDCK Permeability:	2.8515374651760794e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	91.94031524658203%
Volume Distribution (VD):	0.62
Pgp-substrate:	6.102813243865967%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.914
CYP2C19-substrate:	0.364
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.302
CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	0.679
CYP3A4-substrate:	0.491

ADMET: Excretion

Clearance (CL):	5.389
Half-life (T1/2):	0.304

ADMET: Toxicity

hERG Blockers:	0.228
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.788
Rat Oral Acute Toxicity:	0.16
Maximum Recommended Daily Dose:	0.151
Skin Sensitization:	0.434
Carcinogencity:	0.73
Eye Corrosion:	0.004
Eye Irritation:	0.699
Respiratory Toxicity:	0.392

Download Data

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

Natural Product: NPC77955

Natural Product ID:	NPC77955
*Common Name:**	3',4'-Dimethoxyflavone
IUPAC Name:	2-(3,4-dimethoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	ZGHORMOOTZTQFL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O4/c1-19-15-8-7-11(9-17(15)20-2)16-10-13(18)12-5-3-4-6-14(12)21-16/h3-10H,1-2H3
SMILES:	COc1cc(ccc1OC)c1cc(=O)c2c(o1)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL91153
PubChem CID:	688674
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002596] 4'-O-methylated 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
NPO40877	Malagasy connaraceous	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[14510616]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29219	Primula veris	Species	Primulaceae	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	6
MIC	1
Others	7
Potency	23

Activity Type	# Activity
Cell Line	10
Individual Protein	23
Organism	1
Others	1
Protein-Protein Interaction	1
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	IC50	>	500000.0	nM	PMID[490489]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	15848.9	nM	PMID[490490]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	3548.1	nM	PMID[490490]
NPT1161	Cell Line	CHO	Cricetulus griseus	Potency	=	79432.8	nM	PMID[490490]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	=	4466.8	nM	PMID[490490]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	4466.8	nM	PMID[490490]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	35481.3	nM	PMID[490490]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	50118.7	nM	PMID[490490]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	12589.3	nM	PMID[490490]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	35481.3	nM	PMID[490490]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	7924.5	nM	PMID[490490]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	15848.9	nM	PMID[490490]
NPT501	Individual Protein	Alpha-galactosidase A	Homo sapiens	Potency	=	31622.8	nM	PMID[490490]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	7943.3	nM	PMID[490490]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[490490]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[490490]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI	<	50.0	%	PMID[490492]
NPT83	Cell Line	MCF7	Homo sapiens	GI	<	50.0	%	PMID[490492]
NPT65	Cell Line	HepG2	Homo sapiens	GI	<	50.0	%	PMID[490492]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[490490]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[490490]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	39680.0	nM	PMID[490494]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	34540.0	nM	PMID[490494]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6460.0	nM	PMID[490494]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	116.94	%	PMID[490494]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	33.31	%	PMID[490494]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.3	ug.mL-1	PMID[490488]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	10000.0	nM	PMID[490490]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	25118.9	nM	PMID[490490]
NPT714	Individual Protein	Fructose-bisphosphate aldolase A	Oryctolagus cuniculus	Potency	=	125892.5	nM	PMID[490490]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[490490]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	IC50	=	1200.0	nM	PMID[490491]
NPT587	Tissue	Liver microsome	Rattus norvegicus	IC50	=	40.0	ug.mL-1	PMID[490492]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	129.7	%	PMID[490493]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	187.63	%	PMID[490493]
NPT2	Others	Unspecified		Potency	n.a.	7079.5	nM	PMID[490490]

☑ 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 NPC77955 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	536
0.1-0.2	2034
0.2-0.3	5177
0.3-0.4	11951
0.4-0.5	5080
0.5-0.6	4229
0.6-0.7	6609
0.7-0.8	5074
0.8-0.85	1438
0.85-0.9	513
0.9-0.95	54
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9416	High Similarity	NPC113089
0.9348	High Similarity	NPC136278
0.9343	High Similarity	NPC9966
0.9343	High Similarity	NPC70853
0.9275	High Similarity	NPC23955
0.927	High Similarity	NPC29536
0.9214	High Similarity	NPC299923
0.9214	High Similarity	NPC205522
0.9209	High Similarity	NPC471590
0.9167	High Similarity	NPC301717
0.9147	High Similarity	NPC2771
0.9143	High Similarity	NPC40818
0.9143	High Similarity	NPC110639
0.9143	High Similarity	NPC106461
0.9143	High Similarity	NPC215932
0.9143	High Similarity	NPC310259
0.9143	High Similarity	NPC14958
0.9137	High Similarity	NPC293201
0.913	High Similarity	NPC124467
0.913	High Similarity	NPC214919
0.9078	High Similarity	NPC12200
0.9078	High Similarity	NPC85233
0.9014	High Similarity	NPC10304
0.9014	High Similarity	NPC63256
0.9014	High Similarity	NPC195202
0.9014	High Similarity	NPC261548
0.9007	High Similarity	NPC283002
0.9007	High Similarity	NPC302408
0.9007	High Similarity	NPC231013
0.8993	High Similarity	NPC185607
0.8978	High Similarity	NPC44573
0.8958	High Similarity	NPC308451
0.8951	High Similarity	NPC69752
0.8951	High Similarity	NPC137062
0.8951	High Similarity	NPC52005
0.8951	High Similarity	NPC159103
0.8951	High Similarity	NPC223579
0.8951	High Similarity	NPC287101
0.8951	High Similarity	NPC183950
0.8944	High Similarity	NPC62536
0.8944	High Similarity	NPC117463
0.8944	High Similarity	NPC470511
0.8944	High Similarity	NPC33265
0.8939	High Similarity	NPC125887
0.8936	High Similarity	NPC165512
0.8897	High Similarity	NPC55205
0.8897	High Similarity	NPC39732
0.8897	High Similarity	NPC40033
0.8897	High Similarity	NPC60972
0.8889	High Similarity	NPC189270
0.8889	High Similarity	NPC50728
0.8889	High Similarity	NPC306821
0.8889	High Similarity	NPC5840
0.8889	High Similarity	NPC201547
0.8889	High Similarity	NPC259058
0.8889	High Similarity	NPC166753
0.8881	High Similarity	NPC476342
0.8881	High Similarity	NPC120464
0.8873	High Similarity	NPC216314
0.8873	High Similarity	NPC120924
0.8873	High Similarity	NPC195919
0.8864	High Similarity	NPC298884
0.8836	High Similarity	NPC472408
0.8836	High Similarity	NPC279930
0.8836	High Similarity	NPC186507
0.8828	High Similarity	NPC125062
0.8828	High Similarity	NPC208043
0.8828	High Similarity	NPC472535
0.8828	High Similarity	NPC474170
0.8828	High Similarity	NPC474388
0.8828	High Similarity	NPC252933
0.8828	High Similarity	NPC226973
0.8828	High Similarity	NPC54394
0.8828	High Similarity	NPC200740
0.8828	High Similarity	NPC236769
0.8819	High Similarity	NPC181250
0.8819	High Similarity	NPC238366
0.8819	High Similarity	NPC177298
0.8819	High Similarity	NPC48479
0.8819	High Similarity	NPC328119
0.8811	High Similarity	NPC108406
0.8794	High Similarity	NPC476054
0.8786	High Similarity	NPC58229
0.8776	High Similarity	NPC20830
0.8776	High Similarity	NPC256612
0.8776	High Similarity	NPC284353
0.8767	High Similarity	NPC198826
0.8767	High Similarity	NPC212678
0.8767	High Similarity	NPC279989
0.8767	High Similarity	NPC134677
0.8767	High Similarity	NPC239128
0.8767	High Similarity	NPC83508
0.8767	High Similarity	NPC292460
0.8767	High Similarity	NPC100887
0.8767	High Similarity	NPC301323
0.8767	High Similarity	NPC25270
0.8767	High Similarity	NPC293183
0.8767	High Similarity	NPC156222
0.8767	High Similarity	NPC256283
0.8767	High Similarity	NPC188203
0.8767	High Similarity	NPC301123
0.8767	High Similarity	NPC82325
0.8767	High Similarity	NPC166201
0.8767	High Similarity	NPC222830
0.8767	High Similarity	NPC131624
0.8767	High Similarity	NPC71334
0.8767	High Similarity	NPC275722
0.8767	High Similarity	NPC241498
0.8767	High Similarity	NPC162313
0.8767	High Similarity	NPC68882
0.8767	High Similarity	NPC275836
0.8767	High Similarity	NPC57030
0.8767	High Similarity	NPC120163
0.8767	High Similarity	NPC187498
0.8759	High Similarity	NPC177839
0.8759	High Similarity	NPC219330
0.8741	High Similarity	NPC12377
0.8732	High Similarity	NPC182842
0.8716	High Similarity	NPC265511
0.8707	High Similarity	NPC69394
0.8707	High Similarity	NPC472915
0.8707	High Similarity	NPC183878
0.8707	High Similarity	NPC145379
0.8707	High Similarity	NPC86485
0.8707	High Similarity	NPC476289
0.8707	High Similarity	NPC176775
0.8707	High Similarity	NPC236223
0.8707	High Similarity	NPC128961
0.8707	High Similarity	NPC78326
0.8707	High Similarity	NPC47781
0.8707	High Similarity	NPC22519
0.8707	High Similarity	NPC280937
0.8707	High Similarity	NPC160951
0.8707	High Similarity	NPC255350
0.8707	High Similarity	NPC231018
0.8707	High Similarity	NPC179126
0.8707	High Similarity	NPC274327
0.8707	High Similarity	NPC270620
0.8699	High Similarity	NPC133953
0.8699	High Similarity	NPC31363
0.8699	High Similarity	NPC28274
0.8699	High Similarity	NPC149614
0.8699	High Similarity	NPC50403
0.8699	High Similarity	NPC76376
0.8699	High Similarity	NPC260895
0.8699	High Similarity	NPC117579
0.869	High Similarity	NPC270465
0.869	High Similarity	NPC87125
0.869	High Similarity	NPC474648
0.8686	High Similarity	NPC292998
0.8681	High Similarity	NPC46941
0.8681	High Similarity	NPC474999
0.8681	High Similarity	NPC168803
0.8676	High Similarity	NPC284424
0.8676	High Similarity	NPC278556
0.8671	High Similarity	NPC70136
0.8662	High Similarity	NPC119663
0.8658	High Similarity	NPC19097
0.8658	High Similarity	NPC476981
0.8649	High Similarity	NPC241774
0.8649	High Similarity	NPC26227
0.8649	High Similarity	NPC122623
0.8649	High Similarity	NPC189960
0.8649	High Similarity	NPC32557
0.8649	High Similarity	NPC163780
0.8649	High Similarity	NPC50715
0.8649	High Similarity	NPC183597
0.8649	High Similarity	NPC138360
0.8649	High Similarity	NPC234255
0.8649	High Similarity	NPC167815
0.8649	High Similarity	NPC201136
0.8649	High Similarity	NPC2928
0.8649	High Similarity	NPC2476
0.8649	High Similarity	NPC196439
0.8649	High Similarity	NPC255807
0.8649	High Similarity	NPC44079
0.8649	High Similarity	NPC92659
0.8649	High Similarity	NPC34725
0.8649	High Similarity	NPC227325
0.8649	High Similarity	NPC213622
0.8649	High Similarity	NPC208197
0.8649	High Similarity	NPC128863
0.8649	High Similarity	NPC146165
0.8649	High Similarity	NPC4455
0.8649	High Similarity	NPC276059
0.8649	High Similarity	NPC201451
0.8649	High Similarity	NPC31018
0.8649	High Similarity	NPC280339
0.8647	High Similarity	NPC474264
0.8643	High Similarity	NPC223336
0.8639	High Similarity	NPC123886
0.8639	High Similarity	NPC236637
0.8639	High Similarity	NPC302950
0.8639	High Similarity	NPC257648
0.8639	High Similarity	NPC142540
0.8639	High Similarity	NPC471982
0.8639	High Similarity	NPC219582
0.8639	High Similarity	NPC477231
0.8633	High Similarity	NPC254741
0.863	High Similarity	NPC184136

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 NPC77955 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	477
0.1-0.2	999
0.2-0.3	1652
0.3-0.4	2687
0.4-0.5	1748
0.5-0.6	1024
0.6-0.7	411
0.7-0.8	128
0.8-0.85	15
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8707	High Similarity	NPD2801	Approved
0.8649	High Similarity	NPD3817	Phase 2
0.8639	High Similarity	NPD1934	Approved
0.8601	High Similarity	NPD1511	Approved
0.85	High Similarity	NPD2796	Approved
0.8483	Intermediate Similarity	NPD1512	Approved
0.8478	Intermediate Similarity	NPD1933	Approved
0.8421	Intermediate Similarity	NPD5494	Approved
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD447	Suspended
0.8168	Intermediate Similarity	NPD5536	Phase 2
0.8163	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1247	Approved
0.8129	Intermediate Similarity	NPD2313	Discontinued
0.8117	Intermediate Similarity	NPD919	Approved
0.8101	Intermediate Similarity	NPD3818	Discontinued
0.8095	Intermediate Similarity	NPD6799	Approved
0.8089	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6166	Phase 2
0.8089	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD7054	Approved
0.8042	Intermediate Similarity	NPD3748	Approved
0.8042	Intermediate Similarity	NPD1510	Phase 2
0.8025	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD1549	Phase 2
0.8	Intermediate Similarity	NPD7472	Approved
0.7986	Intermediate Similarity	NPD6832	Phase 2
0.7971	Intermediate Similarity	NPD2798	Approved
0.7933	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD2346	Discontinued
0.7931	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD5402	Approved
0.7919	Intermediate Similarity	NPD5401	Approved
0.7917	Intermediate Similarity	NPD2799	Discontinued
0.7895	Intermediate Similarity	NPD4380	Phase 2
0.7888	Intermediate Similarity	NPD7074	Phase 3
0.7887	Intermediate Similarity	NPD1240	Approved
0.7863	Intermediate Similarity	NPD1241	Discontinued
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD7819	Suspended
0.7857	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7808	Phase 3
0.784	Intermediate Similarity	NPD6797	Phase 2
0.7829	Intermediate Similarity	NPD3226	Approved
0.7823	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD5403	Approved
0.78	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6801	Discontinued
0.7791	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD1607	Approved
0.777	Intermediate Similarity	NPD3750	Approved
0.7756	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6232	Discontinued
0.7733	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6385	Approved
0.7727	Intermediate Similarity	NPD6386	Approved
0.7707	Intermediate Similarity	NPD7075	Discontinued
0.7703	Intermediate Similarity	NPD1243	Approved
0.7702	Intermediate Similarity	NPD7473	Discontinued
0.7697	Intermediate Similarity	NPD920	Approved
0.7687	Intermediate Similarity	NPD2344	Approved
0.7651	Intermediate Similarity	NPD4628	Phase 3
0.7643	Intermediate Similarity	NPD1203	Approved
0.7639	Intermediate Similarity	NPD4307	Phase 2
0.7635	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1551	Phase 2
0.7613	Intermediate Similarity	NPD7411	Suspended
0.7607	Intermediate Similarity	NPD5844	Phase 1
0.7594	Intermediate Similarity	NPD5283	Phase 1
0.7591	Intermediate Similarity	NPD17	Approved
0.7589	Intermediate Similarity	NPD1019	Discontinued
0.7571	Intermediate Similarity	NPD1876	Approved
0.7566	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6844	Discontinued
0.7554	Intermediate Similarity	NPD3972	Approved
0.7554	Intermediate Similarity	NPD9717	Approved
0.755	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD9494	Approved
0.7518	Intermediate Similarity	NPD3266	Approved
0.7518	Intermediate Similarity	NPD3267	Approved
0.7517	Intermediate Similarity	NPD943	Approved
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.7483	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2309	Approved
0.747	Intermediate Similarity	NPD6559	Discontinued
0.7468	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1471	Phase 3
0.7432	Intermediate Similarity	NPD4308	Phase 3
0.7429	Intermediate Similarity	NPD1608	Approved
0.7421	Intermediate Similarity	NPD7768	Phase 2
0.7417	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1613	Approved
0.7394	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD411	Approved
0.7379	Intermediate Similarity	NPD6798	Discontinued
0.7368	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6959	Discontinued
0.7338	Intermediate Similarity	NPD4661	Approved
0.7338	Intermediate Similarity	NPD4662	Approved
0.7333	Intermediate Similarity	NPD2353	Approved
0.7333	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3018	Phase 2
0.7273	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD2797	Approved
0.7267	Intermediate Similarity	NPD3749	Approved
0.7266	Intermediate Similarity	NPD1651	Approved
0.7262	Intermediate Similarity	NPD7039	Approved
0.7262	Intermediate Similarity	NPD7038	Approved
0.726	Intermediate Similarity	NPD3268	Approved
0.7256	Intermediate Similarity	NPD5242	Approved
0.7255	Intermediate Similarity	NPD3887	Approved
0.7239	Intermediate Similarity	NPD8127	Discontinued
0.7237	Intermediate Similarity	NPD2800	Approved
0.7234	Intermediate Similarity	NPD1201	Approved
0.7234	Intermediate Similarity	NPD3705	Approved
0.723	Intermediate Similarity	NPD230	Phase 1
0.723	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3146	Approved
0.7219	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6233	Phase 2
0.7203	Intermediate Similarity	NPD3225	Approved
0.72	Intermediate Similarity	NPD7033	Discontinued
0.7192	Intermediate Similarity	NPD3027	Phase 3
0.719	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4110	Phase 3
0.7183	Intermediate Similarity	NPD2981	Phase 2
0.717	Intermediate Similarity	NPD6873	Phase 2
0.7162	Intermediate Similarity	NPD3140	Approved
0.7162	Intermediate Similarity	NPD3142	Approved
0.7143	Intermediate Similarity	NPD5977	Approved
0.7143	Intermediate Similarity	NPD2354	Approved
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD5585	Approved
0.7143	Intermediate Similarity	NPD5978	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD3764	Approved
0.7134	Intermediate Similarity	NPD7199	Phase 2
0.7133	Intermediate Similarity	NPD2982	Phase 2
0.7133	Intermediate Similarity	NPD2983	Phase 2
0.7132	Intermediate Similarity	NPD5535	Approved
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.7126	Intermediate Similarity	NPD2163	Approved
0.7125	Intermediate Similarity	NPD6279	Approved
0.7125	Intermediate Similarity	NPD6280	Approved
0.7124	Intermediate Similarity	NPD2654	Approved
0.7113	Intermediate Similarity	NPD1281	Approved
0.7099	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1653	Approved
0.7086	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD8312	Approved
0.7076	Intermediate Similarity	NPD8313	Approved
0.7075	Intermediate Similarity	NPD7095	Approved
0.7071	Intermediate Similarity	NPD1894	Discontinued
0.7071	Intermediate Similarity	NPD9545	Approved
0.7071	Intermediate Similarity	NPD1548	Phase 1
0.707	Intermediate Similarity	NPD5049	Phase 3
0.707	Intermediate Similarity	NPD6273	Approved
0.707	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5889	Approved
0.7063	Intermediate Similarity	NPD1481	Phase 2
0.7063	Intermediate Similarity	NPD5890	Approved
0.7059	Intermediate Similarity	NPD7685	Pre-registration
0.7059	Intermediate Similarity	NPD228	Approved
0.7055	Intermediate Similarity	NPD2861	Phase 2
0.705	Intermediate Similarity	NPD9493	Approved
0.7048	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2979	Phase 3
0.7044	Intermediate Similarity	NPD7458	Discontinued
0.7044	Intermediate Similarity	NPD2649	Approved
0.7044	Intermediate Similarity	NPD2651	Approved
0.7042	Intermediate Similarity	NPD3496	Discontinued
0.7037	Intermediate Similarity	NPD4288	Approved
0.7032	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6190	Approved
0.7024	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD37	Approved
0.7015	Intermediate Similarity	NPD1358	Approved
0.7007	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2532	Approved
0.7006	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD2534	Approved
0.7006	Intermediate Similarity	NPD2403	Approved
0.7006	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7	Intermediate 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