NPASS Compound

Structure

CID117463 OpenBabel06191715472D 25 27 0 0 0 0 0 0 0 0999 V2000 3.1691 3.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 2.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1691 -0.1229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 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 0.2079 -0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 3.3412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 1.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 2.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 -0.1229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 17 2 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 18 2 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.11
Volume:	343.16
LogP:	2.975
LogD:	2.91
LogS:	-4.862
# Rotatable Bonds:	5
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.777
Synthetic Accessibility Score:	2.24
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.916
MDCK Permeability:	5.451697143143974e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	93.53044128417969%
Volume Distribution (VD):	0.633
Pgp-substrate:	11.403444290161133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.926
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.773
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.603
CYP2C9-substrate:	0.848
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.798
CYP3A4-substrate:	0.563

ADMET: Excretion

Clearance (CL):	9.205
Half-life (T1/2):	0.394

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.958
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.399
Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.259
Skin Sensitization:	0.605
Carcinogencity:	0.721
Eye Corrosion:	0.003
Eye Irritation:	0.159
Respiratory Toxicity:	0.819

Download Data

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

Natural Product: NPC117463

Natural Product ID:	NPC117463
*Common Name:**	4,6,3',4'-Tetramethoxyaurone
IUPAC Name:	(2Z)-2-[(3,4-dimethoxyphenyl)methylidene]-4,6-dimethoxy-1-benzofuran-3-one
Synonyms:	4,6,3',4'-Tetramethoxyaurone
Standard InCHIKey:	CVKDSGICIOMAGA-IUXPMGMMSA-N
Standard InCHI:	InChI=1S/C19H18O6/c1-21-12-9-15(24-4)18-16(10-12)25-17(19(18)20)8-11-5-6-13(22-2)14(7-11)23-3/h5-10H,1-4H3/b17-8-
SMILES:	COc1cc(c2c(c1)O/C(=Cc1ccc(c(c1)OC)OC)/C2=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801772
PubChem CID:	11186921
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
NPO17398	Cyperus teneriffae	Species	Cyperaceae	Eukaryota	n.a.	root	n.a.	PMID[21504148]
NPO17398	Cyperus teneriffae	Species	Cyperaceae	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
EC50	1
ED50	1
Others	15

Activity Type	# Activity
Individual Protein	1
Organism	15
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	EC50	=	910.0	nM	PMID[528256]
NPT35	Others	n.a.		log K	=	0.277	n.a.	PMID[528254]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	pED50	=	6.92	n.a.	PMID[528254]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	ED50	=	0.12	umol/cm2	PMID[528254]
NPT4349	Organism	Paraixeris denticulata	Paraixeris denticulata	Activity	=	100.0	%	PMID[528255]
NPT130	Organism	Digitaria sanguinalis	Digitaria sanguinalis	Activity	=	100.0	%	PMID[528255]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Activity	=	100.0	%	PMID[528255]
NPT4348	Organism	Brassica rapa subsp. campestris	Brassica rapa subsp. campestris	GI	=	77.9	%	PMID[528255]
NPT4349	Organism	Paraixeris denticulata	Paraixeris denticulata	Activity	=	69.6	%	PMID[528255]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	GI	=	61.3	%	PMID[528255]
NPT130	Organism	Digitaria sanguinalis	Digitaria sanguinalis	Activity	=	41.4	%	PMID[528255]
NPT4349	Organism	Paraixeris denticulata	Paraixeris denticulata	Activity	=	20.0	%	PMID[528255]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Activity	=	13.0	%	PMID[528255]
NPT4348	Organism	Brassica rapa subsp. campestris	Brassica rapa subsp. campestris	GI	=	5.3	%	PMID[528255]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	GI	=	0.9	%	PMID[528255]
NPT130	Organism	Digitaria sanguinalis	Digitaria sanguinalis	Activity	=	0.0	%	PMID[528255]

☑ 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 NPC117463 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	479
0.1-0.2	1952
0.2-0.3	5381
0.3-0.4	11562
0.4-0.5	5434
0.5-0.6	3891
0.6-0.7	5498
0.7-0.8	5817
0.8-0.85	1922
0.85-0.9	699
0.9-0.95	61
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9718	High Similarity	NPC299923
0.9648	High Similarity	NPC310259
0.9524	High Similarity	NPC284353
0.9507	High Similarity	NPC113089
0.9456	High Similarity	NPC279930
0.9448	High Similarity	NPC69752
0.9441	High Similarity	NPC136278
0.9437	High Similarity	NPC9966
0.9437	High Similarity	NPC70853
0.9388	High Similarity	NPC304954
0.9384	High Similarity	NPC259058
0.9384	High Similarity	NPC201547
0.9379	High Similarity	NPC261548
0.9371	High Similarity	NPC293201
0.9366	High Similarity	NPC29536
0.9357	High Similarity	NPC44573
0.9333	High Similarity	NPC195832
0.932	High Similarity	NPC236769
0.932	High Similarity	NPC474170
0.932	High Similarity	NPC474388
0.932	High Similarity	NPC472535
0.9315	High Similarity	NPC181250
0.931	High Similarity	NPC205522
0.9306	High Similarity	NPC471590
0.9252	High Similarity	NPC177839
0.9252	High Similarity	NPC50728
0.9252	High Similarity	NPC166753
0.9247	High Similarity	NPC10304
0.9247	High Similarity	NPC63256
0.9241	High Similarity	NPC215932
0.9241	High Similarity	NPC110639
0.9241	High Similarity	NPC106461
0.9241	High Similarity	NPC40818
0.9241	High Similarity	NPC14958
0.9231	High Similarity	NPC28326
0.9205	High Similarity	NPC104459
0.9205	High Similarity	NPC238405
0.9205	High Similarity	NPC257914
0.92	High Similarity	NPC265511
0.9195	High Similarity	NPC179126
0.9195	High Similarity	NPC78326
0.9195	High Similarity	NPC236223
0.9195	High Similarity	NPC270620
0.9189	High Similarity	NPC76376
0.9184	High Similarity	NPC159103
0.9178	High Similarity	NPC85233
0.9178	High Similarity	NPC470511
0.9172	High Similarity	NPC296575
0.9161	High Similarity	NPC58229
0.915	High Similarity	NPC272722
0.915	High Similarity	NPC302741
0.9145	High Similarity	NPC269906
0.9133	High Similarity	NPC471746
0.9133	High Similarity	NPC122623
0.9133	High Similarity	NPC32557
0.9133	High Similarity	NPC241774
0.9133	High Similarity	NPC34725
0.9133	High Similarity	NPC276059
0.9133	High Similarity	NPC189960
0.9128	High Similarity	NPC68882
0.9128	High Similarity	NPC279989
0.9128	High Similarity	NPC55205
0.9128	High Similarity	NPC134677
0.9128	High Similarity	NPC82325
0.9122	High Similarity	NPC219330
0.9122	High Similarity	NPC260582
0.9116	High Similarity	NPC195202
0.9116	High Similarity	NPC19545
0.9116	High Similarity	NPC476342
0.911	High Similarity	NPC283002
0.911	High Similarity	NPC302408
0.911	High Similarity	NPC231013
0.9103	High Similarity	NPC23955
0.9097	High Similarity	NPC185607
0.9073	High Similarity	NPC257277
0.9073	High Similarity	NPC178854
0.9067	High Similarity	NPC246204
0.9067	High Similarity	NPC58382
0.9067	High Similarity	NPC189130
0.9067	High Similarity	NPC473664
0.9067	High Similarity	NPC86485
0.9067	High Similarity	NPC162351
0.906	High Similarity	NPC54394
0.906	High Similarity	NPC252933
0.906	High Similarity	NPC260895
0.906	High Similarity	NPC125062
0.906	High Similarity	NPC200740
0.906	High Similarity	NPC308451
0.9054	High Similarity	NPC238366
0.9048	High Similarity	NPC140840
0.9048	High Similarity	NPC62536
0.9048	High Similarity	NPC86847
0.9048	High Similarity	NPC12200
0.9048	High Similarity	NPC33265
0.9041	High Similarity	NPC165512
0.9034	High Similarity	NPC119663
0.9032	High Similarity	NPC36320
0.902	High Similarity	NPC131557
0.9014	High Similarity	NPC61546
0.9014	High Similarity	NPC72452
0.9013	High Similarity	NPC203891
0.9013	High Similarity	NPC471479
0.9013	High Similarity	NPC101830
0.9013	High Similarity	NPC67876
0.9013	High Similarity	NPC110070
0.9013	High Similarity	NPC471515
0.9013	High Similarity	NPC19097
0.9	High Similarity	NPC292460
0.9	High Similarity	NPC60972
0.9	High Similarity	NPC301123
0.9	High Similarity	NPC39732
0.9	High Similarity	NPC123886
0.9	High Similarity	NPC40033
0.8993	High Similarity	NPC188871
0.8993	High Similarity	NPC286342
0.8993	High Similarity	NPC189270
0.8993	High Similarity	NPC149127
0.8993	High Similarity	NPC5840
0.898	High Similarity	NPC195919
0.898	High Similarity	NPC216314
0.898	High Similarity	NPC120924
0.8968	High Similarity	NPC472582
0.8966	High Similarity	NPC124467
0.8966	High Similarity	NPC214919
0.8961	High Similarity	NPC216092
0.8954	High Similarity	NPC152166
0.8954	High Similarity	NPC115798
0.8954	High Similarity	NPC19687
0.8954	High Similarity	NPC204854
0.8954	High Similarity	NPC4481
0.8954	High Similarity	NPC18607
0.8954	High Similarity	NPC143828
0.8954	High Similarity	NPC7846
0.8954	High Similarity	NPC25495
0.8954	High Similarity	NPC105242
0.8954	High Similarity	NPC130894
0.8954	High Similarity	NPC300943
0.8954	High Similarity	NPC176300
0.8954	High Similarity	NPC191459
0.8954	High Similarity	NPC253634
0.8954	High Similarity	NPC261004
0.8954	High Similarity	NPC193842
0.8954	High Similarity	NPC22472
0.8954	High Similarity	NPC288669
0.8954	High Similarity	NPC18772
0.8954	High Similarity	NPC9609
0.8947	High Similarity	NPC49824
0.8947	High Similarity	NPC200388
0.8947	High Similarity	NPC266960
0.8947	High Similarity	NPC245546
0.8947	High Similarity	NPC303255
0.8947	High Similarity	NPC43243
0.8947	High Similarity	NPC55619
0.8947	High Similarity	NPC471500
0.8947	High Similarity	NPC100916
0.8947	High Similarity	NPC155063
0.8947	High Similarity	NPC292107
0.8944	High Similarity	NPC77955
0.894	High Similarity	NPC186507
0.894	High Similarity	NPC244371
0.894	High Similarity	NPC472408
0.894	High Similarity	NPC476289
0.894	High Similarity	NPC472915
0.8933	High Similarity	NPC50403
0.8933	High Similarity	NPC133953
0.8933	High Similarity	NPC208043
0.8933	High Similarity	NPC28274
0.8933	High Similarity	NPC226973
0.8926	High Similarity	NPC223579
0.8926	High Similarity	NPC287101
0.8926	High Similarity	NPC474648
0.8926	High Similarity	NPC328119
0.8926	High Similarity	NPC177298
0.8926	High Similarity	NPC270465
0.8926	High Similarity	NPC52005
0.8926	High Similarity	NPC137062
0.8926	High Similarity	NPC183950
0.8926	High Similarity	NPC48479
0.8926	High Similarity	NPC87125
0.8919	High Similarity	NPC119660
0.8919	High Similarity	NPC294972
0.8919	High Similarity	NPC93034
0.8912	High Similarity	NPC224687
0.891	High Similarity	NPC45449
0.891	High Similarity	NPC187923
0.8904	High Similarity	NPC476054
0.8903	High Similarity	NPC475144
0.8896	High Similarity	NPC243509
0.8896	High Similarity	NPC298093
0.8889	High Similarity	NPC176665
0.8889	High Similarity	NPC287979
0.8889	High Similarity	NPC305663
0.8889	High Similarity	NPC472438
0.8889	High Similarity	NPC163524
0.8889	High Similarity	NPC7973
0.8889	High Similarity	NPC78302
0.8889	High Similarity	NPC52530
0.8889	High Similarity	NPC235215
0.8889	High Similarity	NPC224137
0.8889	High Similarity	NPC75215

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 NPC117463 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	423
0.1-0.2	1003
0.2-0.3	1807
0.3-0.4	2701
0.4-0.5	1663
0.5-0.6	973
0.6-0.7	415
0.7-0.8	133
0.8-0.85	17
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9329	High Similarity	NPD3882	Suspended
0.9133	High Similarity	NPD3817	Phase 2
0.8896	High Similarity	NPD5494	Approved
0.8846	High Similarity	NPD3926	Phase 2
0.8844	High Similarity	NPD6799	Approved
0.8839	High Similarity	NPD1247	Approved
0.8831	High Similarity	NPD919	Approved
0.8816	High Similarity	NPD2801	Approved
0.875	High Similarity	NPD1934	Approved
0.8725	High Similarity	NPD1512	Approved
0.8621	High Similarity	NPD2796	Approved
0.8591	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD2393	Clinical (unspecified phase)
0.8553	High Similarity	NPD6168	Clinical (unspecified phase)
0.8553	High Similarity	NPD6167	Clinical (unspecified phase)
0.8553	High Similarity	NPD6166	Phase 2
0.8533	High Similarity	NPD4378	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD6599	Discontinued
0.8452	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD3818	Discontinued
0.8421	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7808	Phase 3
0.8293	Intermediate Similarity	NPD6797	Phase 2
0.8291	Intermediate Similarity	NPD7075	Discontinued
0.8269	Intermediate Similarity	NPD6801	Discontinued
0.8242	Intermediate Similarity	NPD7251	Discontinued
0.8193	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7054	Approved
0.8165	Intermediate Similarity	NPD5402	Approved
0.8151	Intermediate Similarity	NPD1240	Approved
0.8133	Intermediate Similarity	NPD1549	Phase 2
0.8121	Intermediate Similarity	NPD7472	Approved
0.8121	Intermediate Similarity	NPD7074	Phase 3
0.8101	Intermediate Similarity	NPD7819	Suspended
0.8079	Intermediate Similarity	NPD1243	Approved
0.8067	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD920	Approved
0.8065	Intermediate Similarity	NPD5403	Approved
0.8054	Intermediate Similarity	NPD1510	Phase 2
0.8052	Intermediate Similarity	NPD5401	Approved
0.8041	Intermediate Similarity	NPD1607	Approved
0.8025	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6232	Discontinued
0.7973	Intermediate Similarity	NPD1933	Approved
0.795	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7473	Discontinued
0.7935	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD2403	Approved
0.7862	Intermediate Similarity	NPD7411	Suspended
0.7852	Intermediate Similarity	NPD447	Suspended
0.7844	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5844	Phase 1
0.7818	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD3748	Approved
0.7785	Intermediate Similarity	NPD943	Approved
0.7778	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6832	Phase 2
0.7751	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2654	Approved
0.7727	Intermediate Similarity	NPD2800	Approved
0.7716	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1471	Phase 3
0.7706	Intermediate Similarity	NPD6559	Discontinued
0.766	Intermediate Similarity	NPD5536	Phase 2
0.7654	Intermediate Similarity	NPD1465	Phase 2
0.7647	Intermediate Similarity	NPD2935	Discontinued
0.7647	Intermediate Similarity	NPD1551	Phase 2
0.7643	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3749	Approved
0.7605	Intermediate Similarity	NPD5242	Approved
0.7597	Intermediate Similarity	NPD2344	Approved
0.7595	Intermediate Similarity	NPD2534	Approved
0.7595	Intermediate Similarity	NPD2533	Approved
0.7595	Intermediate Similarity	NPD2532	Approved
0.759	Intermediate Similarity	NPD7199	Phase 2
0.759	Intermediate Similarity	NPD6959	Discontinued
0.7582	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3750	Approved
0.7531	Intermediate Similarity	NPD6385	Approved
0.7531	Intermediate Similarity	NPD6386	Approved
0.7517	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5353	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7471	Intermediate Similarity	NPD2163	Approved
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7456	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7768	Phase 2
0.7452	Intermediate Similarity	NPD4628	Phase 3
0.745	Intermediate Similarity	NPD3018	Phase 2
0.744	Intermediate Similarity	NPD3787	Discontinued
0.7405	Intermediate Similarity	NPD3887	Approved
0.7405	Intermediate Similarity	NPD2309	Approved
0.74	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3146	Approved
0.7372	Intermediate Similarity	NPD2353	Approved
0.7372	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3027	Phase 3
0.7349	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3972	Approved
0.7347	Intermediate Similarity	NPD2981	Phase 2
0.7342	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1613	Approved
0.7315	Intermediate Similarity	NPD1203	Approved
0.7303	Intermediate Similarity	NPD2313	Discontinued
0.7301	Intermediate Similarity	NPD3226	Approved
0.7297	Intermediate Similarity	NPD2983	Phase 2
0.7297	Intermediate Similarity	NPD2982	Phase 2
0.7297	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD2798	Approved
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7261	Intermediate Similarity	NPD2346	Discontinued
0.726	Intermediate Similarity	NPD17	Approved
0.7257	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1241	Discontinued
0.7246	Intermediate Similarity	NPD4966	Approved
0.7246	Intermediate Similarity	NPD4967	Phase 2
0.7246	Intermediate Similarity	NPD4965	Approved
0.7241	Intermediate Similarity	NPD5953	Discontinued
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD9717	Approved
0.7228	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6651	Approved
0.7225	Intermediate Similarity	NPD7286	Phase 2
0.7219	Intermediate Similarity	NPD9494	Approved
0.7205	Intermediate Similarity	NPD4357	Discontinued
0.7197	Intermediate Similarity	NPD6100	Approved
0.7197	Intermediate Similarity	NPD6099	Approved
0.7191	Intermediate Similarity	NPD8434	Phase 2
0.719	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD2354	Approved
0.7169	Intermediate Similarity	NPD6280	Approved
0.7169	Intermediate Similarity	NPD6279	Approved
0.716	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7134	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1876	Approved
0.7133	Intermediate Similarity	NPD5283	Phase 1
0.7127	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1608	Approved
0.7097	Intermediate Similarity	NPD4307	Phase 2
0.7086	Intermediate Similarity	NPD3266	Approved
0.7086	Intermediate Similarity	NPD3267	Approved
0.7078	Intermediate Similarity	NPD411	Approved
0.7078	Intermediate Similarity	NPD1296	Phase 2
0.7069	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3705	Approved
0.7035	Intermediate Similarity	NPD6808	Phase 2
0.7035	Intermediate Similarity	NPD5711	Approved
0.7035	Intermediate Similarity	NPD7229	Phase 3
0.7035	Intermediate Similarity	NPD5710	Approved
0.703	Intermediate Similarity	NPD1653	Approved
0.7025	Intermediate Similarity	NPD7033	Discontinued
0.7019	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5049	Phase 3
0.7006	Intermediate Similarity	NPD5089	Approved
0.7006	Intermediate Similarity	NPD5090	Approved
0.7	Intermediate Similarity	NPD6971	Discontinued
0.6994	Remote Similarity	NPD7390	Discontinued
0.6987	Remote Similarity	NPD3140	Approved
0.6987	Remote Similarity	NPD3142	Approved
0.6982	Remote Similarity	NPD5977	Approved
0.6982	Remote Similarity	NPD5978	Approved
0.6981	Remote Similarity	NPD3539	Phase 1
0.6968	Remote Similarity	NPD3268	Approved
0.6968	Remote Similarity	NPD5005	Approved
0.6968	Remote Similarity	NPD5006	Approved
0.6964	Remote Similarity	NPD6844	Discontinued
0.6959	Remote Similarity	NPD9268	Approved
0.6951	Remote Similarity	NPD4662	Approved
0.6951	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4661	Approved
0.6948	Remote Similarity	NPD4908	Phase 1
0.6937	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3540	Phase 1
0.6933	Remote Similarity	NPD422	Phase 1
0.6923	Remote Similarity	NPD4585	Approved
0.6923	Remote Similarity	NPD4062	Phase 3
0.6918	Remote Similarity	NPD4308	Phase 3
0.6914	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4110	Phase 3
0.691	Remote Similarity	NPD7685	Pre-registration

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