NPASS Compound

Structure

CID56786 OpenBabel06191715392D 28 30 0 0 0 0 0 0 0 0999 V2000 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -2.5981 -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 2.5981 -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 -0.0000 3.0000 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 1.0000 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 -3.4641 1.0000 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 0.8660 -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 -2.5981 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 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 -1.7321 -2.0000 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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 27 1 0 0 0 0 4 5 1 0 0 0 0 4 10 2 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 16 2 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 26 2 0 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.12
Volume:	383.906
LogP:	4.177
LogD:	2.894
LogS:	-3.911
# Rotatable Bonds:	4
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.503
Synthetic Accessibility Score:	3.017
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.005
MDCK Permeability:	1.311793766944902e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.068

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	99.34761047363281%
Volume Distribution (VD):	0.496
Pgp-substrate:	2.6126277446746826%

ADMET: Metabolism

CYP1A2-inhibitor:	0.912
CYP1A2-substrate:	0.781
CYP2C19-inhibitor:	0.177
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.831
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.672
CYP2D6-substrate:	0.307
CYP3A4-inhibitor:	0.345
CYP3A4-substrate:	0.109

ADMET: Excretion

Clearance (CL):	6.326
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.653
Rat Oral Acute Toxicity:	0.261
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.926
Carcinogencity:	0.249
Eye Corrosion:	0.004
Eye Irritation:	0.91
Respiratory Toxicity:	0.176

Download Data

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

Natural Product: NPC56786

Natural Product ID:	NPC56786
*Common Name:**	Podoverine A
IUPAC Name:	2-[3,4-dihydroxy-2-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-3-methoxychromen-4-one
Synonyms:
Standard InCHIKey:	MGFXFQXRHGAKQN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O7/c1-10(2)4-5-12-13(6-7-14(23)18(12)25)20-21(27-3)19(26)17-15(24)8-11(22)9-16(17)28-20/h4,6-9,22-25H,5H2,1-3H3
SMILES:	COc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(c(c1CC=C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3334619
PubChem CID:	13911680
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003587] 2'-prenylated flavones

*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
NPO1610	Eremophila mitchellii	Species	Scrophulariaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21877688]
NPO40683	Podophyllum versipelle Hance	Strain	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24530033]
NPO259	Podophyllum versipelle	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1610	Eremophila mitchellii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2019	Kopsia dasyrachis	Species	Apocynaceae	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
IC50	1
Others	24

Activity Type	# Activity
Cell Line	17
Others	8
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Flu intensity	=	5.6	n.a.	PMID[507523]
NPT165	Cell Line	HeLa	Homo sapiens	Flu intensity	=	40.4	n.a.	PMID[507523]
NPT165	Cell Line	HeLa	Homo sapiens	Flu intensity	=	40.2	n.a.	PMID[507523]
NPT165	Cell Line	HeLa	Homo sapiens	Flu intensity	=	13.8	n.a.	PMID[507523]
NPT165	Cell Line	HeLa	Homo sapiens	Flu intensity	=	9.84	n.a.	PMID[507523]
NPT165	Cell Line	HeLa	Homo sapiens	Flu intensity	=	9.6	n.a.	PMID[507523]
NPT165	Cell Line	HeLa	Homo sapiens	Flu intensity	=	58.2	n.a.	PMID[507523]
NPT165	Cell Line	HeLa	Homo sapiens	Flu intensity	=	21.8	n.a.	PMID[507523]
NPT83	Cell Line	MCF7	Homo sapiens	Flu intensity	=	1.07	n.a.	PMID[507523]
NPT83	Cell Line	MCF7	Homo sapiens	Flu intensity	=	32.0	n.a.	PMID[507523]
NPT83	Cell Line	MCF7	Homo sapiens	Flu intensity	=	36.3	n.a.	PMID[507523]
NPT83	Cell Line	MCF7	Homo sapiens	Flu intensity	=	29.6	n.a.	PMID[507523]
NPT83	Cell Line	MCF7	Homo sapiens	Flu intensity	=	2.0	n.a.	PMID[507523]
NPT83	Cell Line	MCF7	Homo sapiens	Flu intensity	=	9.57	n.a.	PMID[507523]
NPT83	Cell Line	MCF7	Homo sapiens	Flu intensity	=	61.5	n.a.	PMID[507523]
NPT83	Cell Line	MCF7	Homo sapiens	Flu intensity	=	27.0	n.a.	PMID[507523]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	790.0	nM	PMID[507523]
NPT518	Protein Complex	Tubulin	Homo sapiens	EC50	=	14700.0	nM	PMID[507523]
NPT610	Others	Molecular identity unknown		Flu intensity	=	2.23	n.a.	PMID[507523]
NPT610	Others	Molecular identity unknown		Flu intensity	=	27.6	n.a.	PMID[507523]
NPT610	Others	Molecular identity unknown		Flu intensity	=	42.0	n.a.	PMID[507523]
NPT610	Others	Molecular identity unknown		Flu intensity	=	26.5	n.a.	PMID[507523]
NPT610	Others	Molecular identity unknown		Flu intensity	=	12.6	n.a.	PMID[507523]
NPT610	Others	Molecular identity unknown		Flu intensity	=	9.24	n.a.	PMID[507523]
NPT610	Others	Molecular identity unknown		Flu intensity	=	47.5	n.a.	PMID[507523]
NPT610	Others	Molecular identity unknown		Flu intensity	=	30.8	n.a.	PMID[507523]

☑ 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 NPC56786 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	448
0.1-0.2	1904
0.2-0.3	4632
0.3-0.4	10932
0.4-0.5	6709
0.5-0.6	3643
0.6-0.7	5044
0.7-0.8	5048
0.8-0.85	2242
0.85-0.9	1306
0.9-0.95	631
0.95-1	158

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC80534
0.9728	High Similarity	NPC149127
0.9728	High Similarity	NPC188871
0.9728	High Similarity	NPC286342
0.9667	High Similarity	NPC153512
0.9664	High Similarity	NPC270620
0.9664	High Similarity	NPC236223
0.9664	High Similarity	NPC179126
0.9664	High Similarity	NPC78326
0.9662	High Similarity	NPC260895
0.966	High Similarity	NPC270465
0.966	High Similarity	NPC87125
0.9603	High Similarity	NPC273843
0.96	High Similarity	NPC133392
0.9597	High Similarity	NPC82325
0.9597	High Similarity	NPC279989
0.9539	High Similarity	NPC280680
0.9536	High Similarity	NPC13779
0.9536	High Similarity	NPC475799
0.9536	High Similarity	NPC265511
0.9533	High Similarity	NPC58382
0.9533	High Similarity	NPC162351
0.953	High Similarity	NPC252933
0.953	High Similarity	NPC125062
0.953	High Similarity	NPC200740
0.953	High Similarity	NPC54394
0.953	High Similarity	NPC236769
0.9524	High Similarity	NPC259632
0.9524	High Similarity	NPC108406
0.9474	High Similarity	NPC203891
0.9474	High Similarity	NPC101830
0.9474	High Similarity	NPC110070
0.947	High Similarity	NPC67396
0.947	High Similarity	NPC214138
0.9467	High Similarity	NPC123886
0.9467	High Similarity	NPC63187
0.9467	High Similarity	NPC55205
0.9467	High Similarity	NPC37684
0.9467	High Similarity	NPC157784
0.9463	High Similarity	NPC166753
0.9463	High Similarity	NPC50728
0.9456	High Similarity	NPC20791
0.9456	High Similarity	NPC179271
0.9412	High Similarity	NPC143828
0.9412	High Similarity	NPC152166
0.9412	High Similarity	NPC7846
0.9412	High Similarity	NPC22472
0.9412	High Similarity	NPC204854
0.9412	High Similarity	NPC191459
0.9412	High Similarity	NPC115798
0.9412	High Similarity	NPC18772
0.9412	High Similarity	NPC130894
0.9412	High Similarity	NPC18607
0.9412	High Similarity	NPC300943
0.9412	High Similarity	NPC253634
0.9412	High Similarity	NPC105242
0.9412	High Similarity	NPC19687
0.9412	High Similarity	NPC4481
0.9412	High Similarity	NPC288669
0.9412	High Similarity	NPC25495
0.9412	High Similarity	NPC176300
0.9412	High Similarity	NPC261004
0.9412	High Similarity	NPC9609
0.9408	High Similarity	NPC49824
0.9408	High Similarity	NPC24640
0.9408	High Similarity	NPC266960
0.9408	High Similarity	NPC292107
0.9408	High Similarity	NPC200388
0.9408	High Similarity	NPC471500
0.9408	High Similarity	NPC55619
0.9408	High Similarity	NPC245546
0.9408	High Similarity	NPC100916
0.9408	High Similarity	NPC43243
0.9408	High Similarity	NPC3980
0.94	High Similarity	NPC133953
0.94	High Similarity	NPC76376
0.94	High Similarity	NPC50403
0.94	High Similarity	NPC205046
0.94	High Similarity	NPC28274
0.94	High Similarity	NPC304295
0.94	High Similarity	NPC59162
0.9396	High Similarity	NPC48479
0.9396	High Similarity	NPC159103
0.9396	High Similarity	NPC137062
0.9396	High Similarity	NPC183950
0.9396	High Similarity	NPC52005
0.9396	High Similarity	NPC287101
0.9396	High Similarity	NPC177298
0.9396	High Similarity	NPC223579
0.9392	High Similarity	NPC51443
0.9392	High Similarity	NPC74881
0.9346	High Similarity	NPC176665
0.9346	High Similarity	NPC224137
0.9346	High Similarity	NPC29841
0.9346	High Similarity	NPC235215
0.9346	High Similarity	NPC93376
0.9346	High Similarity	NPC189179
0.9346	High Similarity	NPC163524
0.9346	High Similarity	NPC471479
0.9346	High Similarity	NPC227192
0.9346	High Similarity	NPC305663
0.9346	High Similarity	NPC7973
0.9346	High Similarity	NPC287979
0.9346	High Similarity	NPC471515
0.9346	High Similarity	NPC472438
0.9346	High Similarity	NPC75215
0.9346	High Similarity	NPC78302
0.9342	High Similarity	NPC32557
0.9342	High Similarity	NPC201451
0.9342	High Similarity	NPC189960
0.9342	High Similarity	NPC26227
0.9342	High Similarity	NPC44079
0.9338	High Similarity	NPC60972
0.9338	High Similarity	NPC39732
0.9333	High Similarity	NPC184136
0.9333	High Similarity	NPC219330
0.9333	High Similarity	NPC85131
0.9333	High Similarity	NPC3825
0.9333	High Similarity	NPC88804
0.9329	High Similarity	NPC261548
0.9329	High Similarity	NPC119059
0.9329	High Similarity	NPC195202
0.9329	High Similarity	NPC120464
0.9324	High Similarity	NPC169749
0.932	High Similarity	NPC279121
0.9299	High Similarity	NPC477517
0.9286	High Similarity	NPC210459
0.9286	High Similarity	NPC193842
0.9281	High Similarity	NPC474520
0.9281	High Similarity	NPC247017
0.9281	High Similarity	NPC98661
0.9281	High Similarity	NPC268161
0.9281	High Similarity	NPC178854
0.9276	High Similarity	NPC274327
0.9276	High Similarity	NPC231018
0.9276	High Similarity	NPC183878
0.9276	High Similarity	NPC86485
0.9276	High Similarity	NPC22519
0.9276	High Similarity	NPC255350
0.9276	High Similarity	NPC160951
0.9276	High Similarity	NPC176775
0.9276	High Similarity	NPC69394
0.9276	High Similarity	NPC145379
0.9276	High Similarity	NPC246204
0.9276	High Similarity	NPC47781
0.9276	High Similarity	NPC89474
0.9267	High Similarity	NPC195351
0.9262	High Similarity	NPC62536
0.9262	High Similarity	NPC33265
0.9262	High Similarity	NPC12200
0.9257	High Similarity	NPC70136
0.9252	High Similarity	NPC175013
0.9231	High Similarity	NPC211107
0.9226	High Similarity	NPC36217
0.9226	High Similarity	NPC246478
0.9226	High Similarity	NPC321399
0.9226	High Similarity	NPC297212
0.9226	High Similarity	NPC470183
0.9226	High Similarity	NPC474960
0.9221	High Similarity	NPC237418
0.9221	High Similarity	NPC241904
0.9221	High Similarity	NPC174908
0.9221	High Similarity	NPC300727
0.9221	High Similarity	NPC67876
0.9221	High Similarity	NPC472963
0.9216	High Similarity	NPC256612
0.9216	High Similarity	NPC146165
0.9216	High Similarity	NPC128863
0.9216	High Similarity	NPC213622
0.9216	High Similarity	NPC50715
0.9216	High Similarity	NPC92659
0.9216	High Similarity	NPC20830
0.9216	High Similarity	NPC227325
0.9216	High Similarity	NPC163780
0.9216	High Similarity	NPC2476
0.9216	High Similarity	NPC167815
0.9216	High Similarity	NPC196439
0.9216	High Similarity	NPC138360
0.9216	High Similarity	NPC280339
0.9216	High Similarity	NPC183597
0.9216	High Similarity	NPC201136
0.9216	High Similarity	NPC4455
0.9211	High Similarity	NPC301323
0.9211	High Similarity	NPC25270
0.9211	High Similarity	NPC71334
0.9211	High Similarity	NPC162313
0.9211	High Similarity	NPC156222
0.9211	High Similarity	NPC301123
0.9211	High Similarity	NPC275836
0.9211	High Similarity	NPC239128
0.9211	High Similarity	NPC256283
0.9211	High Similarity	NPC198826
0.9211	High Similarity	NPC471982
0.9211	High Similarity	NPC293183
0.9211	High Similarity	NPC187498
0.9211	High Similarity	NPC188203
0.9211	High Similarity	NPC131624
0.9211	High Similarity	NPC275722
0.9211	High Similarity	NPC222830
0.9211	High Similarity	NPC120163

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 NPC56786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	992
0.2-0.3	1757
0.3-0.4	2689
0.4-0.5	1751
0.5-0.6	973
0.6-0.7	397
0.7-0.8	120
0.8-0.85	32
0.85-0.9	15
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9456	High Similarity	NPD1512	Approved
0.932	High Similarity	NPD1511	Approved
0.9276	High Similarity	NPD2801	Approved
0.9156	High Similarity	NPD3882	Suspended
0.915	High Similarity	NPD2393	Clinical (unspecified phase)
0.9091	High Similarity	NPD3817	Phase 2
0.9085	High Similarity	NPD1934	Approved
0.9	High Similarity	NPD4378	Clinical (unspecified phase)
0.8875	High Similarity	NPD6168	Clinical (unspecified phase)
0.8875	High Similarity	NPD6166	Phase 2
0.8875	High Similarity	NPD6167	Clinical (unspecified phase)
0.8834	High Similarity	NPD6797	Phase 2
0.878	High Similarity	NPD7251	Discontinued
0.8614	High Similarity	NPD7808	Phase 3
0.8614	High Similarity	NPD4338	Clinical (unspecified phase)
0.8598	High Similarity	NPD7054	Approved
0.8562	High Similarity	NPD6799	Approved
0.8545	High Similarity	NPD7472	Approved
0.8537	High Similarity	NPD3818	Discontinued
0.85	High Similarity	NPD7075	Discontinued
0.8477	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD7074	Phase 3
0.8428	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7819	Suspended
0.8411	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD6232	Discontinued
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8365	Intermediate Similarity	NPD6801	Discontinued
0.8364	Intermediate Similarity	NPD7473	Discontinued
0.8355	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD6599	Discontinued
0.8354	Intermediate Similarity	NPD4380	Phase 2
0.8344	Intermediate Similarity	NPD2796	Approved
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD5402	Approved
0.8255	Intermediate Similarity	NPD1240	Approved
0.8247	Intermediate Similarity	NPD3750	Approved
0.8232	Intermediate Similarity	NPD6959	Discontinued
0.8199	Intermediate Similarity	NPD1465	Phase 2
0.8171	Intermediate Similarity	NPD5494	Approved
0.8165	Intermediate Similarity	NPD5403	Approved
0.8148	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1607	Approved
0.8133	Intermediate Similarity	NPD943	Approved
0.8059	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD5844	Phase 1
0.8038	Intermediate Similarity	NPD5401	Approved
0.8024	Intermediate Similarity	NPD3926	Phase 2
0.8012	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD919	Approved
0.7963	Intermediate Similarity	NPD7411	Suspended
0.7939	Intermediate Similarity	NPD3749	Approved
0.7925	Intermediate Similarity	NPD2533	Approved
0.7925	Intermediate Similarity	NPD2532	Approved
0.7925	Intermediate Similarity	NPD2534	Approved
0.7922	Intermediate Similarity	NPD3748	Approved
0.7917	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3751	Discontinued
0.7867	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3787	Discontinued
0.7843	Intermediate Similarity	NPD230	Phase 1
0.7834	Intermediate Similarity	NPD2800	Approved
0.78	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7765	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6099	Approved
0.7756	Intermediate Similarity	NPD2935	Discontinued
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.7756	Intermediate Similarity	NPD6100	Approved
0.773	Intermediate Similarity	NPD3226	Approved
0.7701	Intermediate Similarity	NPD6559	Discontinued
0.7692	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7390	Discontinued
0.7625	Intermediate Similarity	NPD6190	Approved
0.7613	Intermediate Similarity	NPD447	Suspended
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2346	Discontinued
0.7595	Intermediate Similarity	NPD2344	Approved
0.7582	Intermediate Similarity	NPD3027	Phase 3
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.7562	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4628	Phase 3
0.7557	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD1243	Approved
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7452	Intermediate Similarity	NPD6651	Approved
0.7436	Intermediate Similarity	NPD4060	Phase 1
0.7434	Intermediate Similarity	NPD1203	Approved
0.743	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2313	Discontinued
0.7419	Intermediate Similarity	NPD3268	Approved
0.7417	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2309	Approved
0.7403	Intermediate Similarity	NPD4908	Phase 1
0.7389	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD2798	Approved
0.7381	Intermediate Similarity	NPD37	Approved
0.7378	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1471	Phase 3
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.7362	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2403	Approved
0.7355	Intermediate Similarity	NPD4625	Phase 3
0.7353	Intermediate Similarity	NPD4966	Approved
0.7353	Intermediate Similarity	NPD4967	Phase 2
0.7353	Intermediate Similarity	NPD4965	Approved
0.7351	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1653	Approved
0.7346	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5953	Discontinued
0.7341	Intermediate Similarity	NPD5711	Approved
0.7341	Intermediate Similarity	NPD5710	Approved
0.7338	Intermediate Similarity	NPD9494	Approved
0.733	Intermediate Similarity	NPD7286	Phase 2
0.732	Intermediate Similarity	NPD2797	Approved
0.7308	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6798	Discontinued
0.7294	Intermediate Similarity	NPD4288	Approved
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.729	Intermediate Similarity	NPD6832	Phase 2
0.7285	Intermediate Similarity	NPD1201	Approved
0.7285	Intermediate Similarity	NPD1610	Phase 2
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7278	Intermediate Similarity	NPD6355	Discontinued
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7228	Approved
0.7261	Intermediate Similarity	NPD6233	Phase 2
0.725	Intermediate Similarity	NPD7033	Discontinued
0.7243	Intermediate Similarity	NPD4360	Phase 2
0.7243	Intermediate Similarity	NPD4363	Phase 3
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7237	Intermediate Similarity	NPD9717	Approved
0.7237	Intermediate Similarity	NPD9269	Phase 2
0.7237	Intermediate Similarity	NPD1608	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7222	Intermediate Similarity	NPD8312	Approved
0.7222	Intermediate Similarity	NPD8313	Approved
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7208	Intermediate Similarity	NPD1470	Approved
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7198	Intermediate Similarity	NPD8150	Discontinued
0.7178	Intermediate Similarity	NPD2654	Approved
0.7171	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3300	Phase 2
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD3225	Approved
0.7134	Intermediate Similarity	NPD7095	Approved
0.7112	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4361	Phase 2
0.7102	Intermediate Similarity	NPD5242	Approved
0.7101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5405	Approved
0.7099	Intermediate Similarity	NPD5404	Approved
0.7099	Intermediate Similarity	NPD5408	Approved
0.7099	Intermediate Similarity	NPD5406	Approved
0.7097	Intermediate Similarity	NPD3266	Approved
0.7097	Intermediate Similarity	NPD3267	Approved
0.7091	Intermediate Similarity	NPD2354	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7089	Intermediate Similarity	NPD3764	Approved
0.7078	Intermediate Similarity	NPD4749	Approved
0.7076	Intermediate Similarity	NPD6844	Discontinued
0.7039	Intermediate Similarity	NPD17	Approved
0.7031	Intermediate Similarity	NPD7696	Phase 3
0.7031	Intermediate Similarity	NPD7697	Approved
0.7031	Intermediate Similarity	NPD7698	Approved
0.7027	Intermediate Similarity	NPD4287	Approved
0.7026	Intermediate Similarity	NPD8151	Discontinued
0.7016	Intermediate Similarity	NPD2494	Approved
0.7016	Intermediate Similarity	NPD2493	Approved
0.7013	Intermediate Similarity	NPD3972	Approved
0.7006	Intermediate Similarity	NPD2861	Phase 2
0.7006	Intermediate Similarity	NPD3018	Phase 2
0.6995	Remote Similarity	NPD7870	Phase 2
0.6995	Remote Similarity	NPD7871	Phase 2
0.699	Remote Similarity	NPD7874	Approved

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