NPASS Compound

Structure

CID174908 OpenBabel06191715552D 28 29 0 0 0 0 0 0 0 0999 V2000 5.6962 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -4.5000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 8.2942 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6962 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -1.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -4.0947 -2.0619 0.0000 K 0 3 0 0 0 15 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 2 0 0 0 0 2 7 1 0 0 0 0 3 9 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 15 16 2 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 21 27 1 0 0 0 0 22 27 2 0 0 0 0 23 27 2 0 0 0 0 26 27 1 0 0 0 0 M CHG 2 17 -1 28 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	395.01
Volume:	343.624
LogP:	1.413
LogD:	0.283
LogS:	-3.741
# Rotatable Bonds:	4
TPSA:	166.56
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	2.939
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:	-4.837
MDCK Permeability:	1.302925738855265e-05
Pgp-inhibitor:	0.945
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.071
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	97.66658782958984%
Volume Distribution (VD):	0.358
Pgp-substrate:	1.790903925895691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.896
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.084
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.519
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.575
CYP2D6-substrate:	0.255
CYP3A4-inhibitor:	0.289
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	1.19
Half-life (T1/2):	0.717

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.909
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.273
Rat Oral Acute Toxicity:	0.301
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.368
Carcinogencity:	0.712
Eye Corrosion:	0.005
Eye Irritation:	0.908
Respiratory Toxicity:	0.648

Download Data

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

Natural Product: NPC174908

Natural Product ID:	NPC174908
*Common Name:**	Persicarin
IUPAC Name:	potassium;[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl] sulfate
Synonyms:	Percicarin; Persicarin
Standard InCHIKey:	OBHPUIPWBGHSKF-UHFFFAOYSA-M
Standard InCHI:	InChI=1S/C16H12O10S.K/c1-24-11-4-7(2-3-9(11)18)15-16(26-27(21,22)23)14(20)13-10(19)5-8(17)6-12(13)25-15;/h2-6,17-19H,1H3,(H,21,22,23);/q;+1/p-1
SMILES:	COc1cc(ccc1O)c1oc2cc([O-])cc(c2c(=O)c1OS(=O)(=O)O)O.[K+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471479
PubChem CID:	23669384
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002595] 3'-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
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12628396]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	Hairy roots	n.a.	n.a.	PMID[19271765]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26285573]
NPO522	Oenanthe javanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31125231]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619887]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631435]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264679]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264682]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320741]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30896	Polygonum hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30342	Polygonum thunbergii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO522	Oenanthe javanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30896	Polygonum hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[Nippon Kogaku Zasshi, 91, (1970), 762]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO522	Oenanthe javanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO522	Oenanthe javanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30896	Polygonum hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO522	Oenanthe javanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5881	Catharanthus roseus	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
IC50	4
Others	1

Activity Type	# Activity
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	90.3	%	PMID[525638]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	IC50	=	34600.0	nM	PMID[525638]
NPT1578	Individual Protein	Aldose reductase	Sus scrofa	IC50	=	69000.0	nM	PMID[525639]
NPT2	Others	Unspecified		IC50	>	69000.0	nM	PMID[525639]

☑ 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 NPC174908 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	531
0.1-0.2	2232
0.2-0.3	5818
0.3-0.4	11636
0.4-0.5	5009
0.5-0.6	4466
0.6-0.7	5313
0.7-0.8	4783
0.8-0.85	1644
0.85-0.9	862
0.9-0.95	382
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9664	High Similarity	NPC54394
0.9664	High Similarity	NPC28274
0.9664	High Similarity	NPC125062
0.9664	High Similarity	NPC133953
0.9664	High Similarity	NPC200740
0.9664	High Similarity	NPC252933
0.9664	High Similarity	NPC50403
0.96	High Similarity	NPC82325
0.96	High Similarity	NPC55205
0.96	High Similarity	NPC123886
0.96	High Similarity	NPC279989
0.9539	High Similarity	NPC98661
0.9539	High Similarity	NPC247017
0.9536	High Similarity	NPC236223
0.9536	High Similarity	NPC58382
0.9536	High Similarity	NPC270620
0.9536	High Similarity	NPC78326
0.9536	High Similarity	NPC162351
0.9536	High Similarity	NPC179126
0.953	High Similarity	NPC287101
0.953	High Similarity	NPC137062
0.953	High Similarity	NPC87125
0.953	High Similarity	NPC270465
0.953	High Similarity	NPC223579
0.953	High Similarity	NPC159103
0.953	High Similarity	NPC183950
0.953	High Similarity	NPC52005
0.9477	High Similarity	NPC176665
0.9477	High Similarity	NPC75215
0.9477	High Similarity	NPC287979
0.9477	High Similarity	NPC305663
0.9477	High Similarity	NPC227192
0.9477	High Similarity	NPC224137
0.9477	High Similarity	NPC189179
0.9477	High Similarity	NPC93376
0.9477	High Similarity	NPC163524
0.9474	High Similarity	NPC44079
0.9474	High Similarity	NPC26227
0.9474	High Similarity	NPC201451
0.9467	High Similarity	NPC149127
0.9467	High Similarity	NPC188871
0.9467	High Similarity	NPC286342
0.9467	High Similarity	NPC50728
0.9467	High Similarity	NPC166753
0.9467	High Similarity	NPC219330
0.9463	High Similarity	NPC120464
0.9416	High Similarity	NPC152166
0.9416	High Similarity	NPC143828
0.9416	High Similarity	NPC22472
0.9416	High Similarity	NPC204854
0.9416	High Similarity	NPC115798
0.9416	High Similarity	NPC253634
0.9416	High Similarity	NPC18772
0.9416	High Similarity	NPC130894
0.9416	High Similarity	NPC18607
0.9416	High Similarity	NPC7846
0.9416	High Similarity	NPC300943
0.9416	High Similarity	NPC105242
0.9416	High Similarity	NPC4481
0.9416	High Similarity	NPC191459
0.9416	High Similarity	NPC288669
0.9416	High Similarity	NPC25495
0.9416	High Similarity	NPC176300
0.9416	High Similarity	NPC261004
0.9416	High Similarity	NPC19687
0.9416	High Similarity	NPC9609
0.9412	High Similarity	NPC474520
0.9412	High Similarity	NPC245546
0.9412	High Similarity	NPC100916
0.9412	High Similarity	NPC265511
0.9412	High Similarity	NPC200388
0.9412	High Similarity	NPC43243
0.9412	High Similarity	NPC55619
0.9412	High Similarity	NPC49824
0.9412	High Similarity	NPC266960
0.9408	High Similarity	NPC476289
0.9404	High Similarity	NPC236769
0.9404	High Similarity	NPC260895
0.9404	High Similarity	NPC76376
0.94	High Similarity	NPC48479
0.94	High Similarity	NPC177298
0.9396	High Similarity	NPC108406
0.9396	High Similarity	NPC12200
0.9351	High Similarity	NPC110070
0.9351	High Similarity	NPC203891
0.9351	High Similarity	NPC7973
0.9351	High Similarity	NPC101830
0.9351	High Similarity	NPC472438
0.9351	High Similarity	NPC78302
0.9351	High Similarity	NPC29841
0.9351	High Similarity	NPC235215
0.9346	High Similarity	NPC201136
0.9346	High Similarity	NPC167815
0.9346	High Similarity	NPC4455
0.9346	High Similarity	NPC196439
0.9346	High Similarity	NPC138360
0.9346	High Similarity	NPC280339
0.9346	High Similarity	NPC146165
0.9346	High Similarity	NPC92659
0.9346	High Similarity	NPC183597
0.9346	High Similarity	NPC214138
0.9346	High Similarity	NPC227325
0.9346	High Similarity	NPC163780
0.9346	High Similarity	NPC50715
0.9346	High Similarity	NPC2476
0.9346	High Similarity	NPC128863
0.9342	High Similarity	NPC293183
0.9342	High Similarity	NPC256283
0.9342	High Similarity	NPC162313
0.9342	High Similarity	NPC120163
0.9342	High Similarity	NPC188203
0.9342	High Similarity	NPC131624
0.9342	High Similarity	NPC241498
0.9342	High Similarity	NPC275722
0.9342	High Similarity	NPC275836
0.9342	High Similarity	NPC198826
0.9342	High Similarity	NPC239128
0.9342	High Similarity	NPC39732
0.9342	High Similarity	NPC212678
0.9342	High Similarity	NPC156222
0.9342	High Similarity	NPC142540
0.9342	High Similarity	NPC57030
0.9342	High Similarity	NPC60972
0.9342	High Similarity	NPC25270
0.9342	High Similarity	NPC100887
0.9342	High Similarity	NPC301323
0.9342	High Similarity	NPC83508
0.9342	High Similarity	NPC187498
0.9342	High Similarity	NPC222830
0.9342	High Similarity	NPC71334
0.9342	High Similarity	NPC301123
0.9342	High Similarity	NPC27208
0.9333	High Similarity	NPC195202
0.9333	High Similarity	NPC261548
0.9329	High Similarity	NPC20791
0.9329	High Similarity	NPC169749
0.9329	High Similarity	NPC179271
0.929	High Similarity	NPC193842
0.9286	High Similarity	NPC326037
0.9286	High Similarity	NPC13858
0.9286	High Similarity	NPC250922
0.9286	High Similarity	NPC292107
0.9286	High Similarity	NPC178854
0.9286	High Similarity	NPC320825
0.9286	High Similarity	NPC268161
0.9281	High Similarity	NPC255350
0.9281	High Similarity	NPC86485
0.9281	High Similarity	NPC176775
0.9281	High Similarity	NPC250822
0.9281	High Similarity	NPC75279
0.9281	High Similarity	NPC160951
0.9281	High Similarity	NPC246204
0.9281	High Similarity	NPC231018
0.9281	High Similarity	NPC47781
0.9281	High Similarity	NPC69394
0.9281	High Similarity	NPC145379
0.9281	High Similarity	NPC22519
0.9281	High Similarity	NPC276409
0.9281	High Similarity	NPC274327
0.9281	High Similarity	NPC183878
0.9276	High Similarity	NPC225731
0.9267	High Similarity	NPC62536
0.9267	High Similarity	NPC33265
0.9267	High Similarity	NPC51443
0.9267	High Similarity	NPC74881
0.9226	High Similarity	NPC471515
0.9226	High Similarity	NPC67876
0.9226	High Similarity	NPC471479
0.9226	High Similarity	NPC52530
0.9221	High Similarity	NPC208197
0.9221	High Similarity	NPC213622
0.9221	High Similarity	NPC256612
0.9221	High Similarity	NPC32557
0.9221	High Similarity	NPC56786
0.9221	High Similarity	NPC80534
0.9221	High Similarity	NPC20830
0.9221	High Similarity	NPC133392
0.9221	High Similarity	NPC189960
0.9216	High Similarity	NPC236637
0.9216	High Similarity	NPC37684
0.9216	High Similarity	NPC471982
0.9216	High Similarity	NPC63187
0.9216	High Similarity	NPC219582
0.9216	High Similarity	NPC157784
0.9216	High Similarity	NPC302950
0.9216	High Similarity	NPC134677
0.9216	High Similarity	NPC304954
0.9211	High Similarity	NPC77858
0.9211	High Similarity	NPC184136
0.9211	High Similarity	NPC306821
0.9205	High Similarity	NPC119059
0.9195	High Similarity	NPC279121
0.9172	High Similarity	NPC471499
0.9167	High Similarity	NPC280680
0.9167	High Similarity	NPC284127
0.9167	High Similarity	NPC476410
0.9167	High Similarity	NPC172202
0.9167	High Similarity	NPC55738
0.9161	High Similarity	NPC471500
0.9161	High Similarity	NPC474638

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 NPC174908 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	476
0.1-0.2	1040
0.2-0.3	1994
0.3-0.4	2745
0.4-0.5	1569
0.5-0.6	926
0.6-0.7	273
0.7-0.8	91
0.8-0.85	21
0.85-0.9	9
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9329	High Similarity	NPD1512	Approved
0.9281	High Similarity	NPD2801	Approved
0.9216	High Similarity	NPD1934	Approved
0.9195	High Similarity	NPD1511	Approved
0.9097	High Similarity	NPD3817	Phase 2
0.9038	High Similarity	NPD3882	Suspended
0.9	High Similarity	NPD6167	Clinical (unspecified phase)
0.9	High Similarity	NPD6166	Phase 2
0.9	High Similarity	NPD6168	Clinical (unspecified phase)
0.891	High Similarity	NPD2393	Clinical (unspecified phase)
0.8758	High Similarity	NPD4378	Clinical (unspecified phase)
0.8727	High Similarity	NPD6797	Phase 2
0.872	High Similarity	NPD7054	Approved
0.8675	High Similarity	NPD7251	Discontinued
0.8667	High Similarity	NPD7472	Approved
0.8659	High Similarity	NPD3818	Discontinued
0.8623	High Similarity	NPD7808	Phase 3
0.8623	High Similarity	NPD4338	Clinical (unspecified phase)
0.8554	High Similarity	NPD7074	Phase 3
0.8395	Intermediate Similarity	NPD7075	Discontinued
0.8365	Intermediate Similarity	NPD4380	Phase 2
0.8333	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.8282	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6801	Discontinued
0.8247	Intermediate Similarity	NPD1549	Phase 2
0.821	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6232	Discontinued
0.8166	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD5402	Approved
0.8155	Intermediate Similarity	NPD7473	Discontinued
0.8146	Intermediate Similarity	NPD1240	Approved
0.8117	Intermediate Similarity	NPD2796	Approved
0.8098	Intermediate Similarity	NPD1465	Phase 2
0.8072	Intermediate Similarity	NPD5494	Approved
0.807	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5403	Approved
0.805	Intermediate Similarity	NPD5401	Approved
0.8039	Intermediate Similarity	NPD1607	Approved
0.8036	Intermediate Similarity	NPD3926	Phase 2
0.8026	Intermediate Similarity	NPD943	Approved
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8024	Intermediate Similarity	NPD1247	Approved
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD919	Approved
0.7988	Intermediate Similarity	NPD7819	Suspended
0.7939	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7411	Suspended
0.7821	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6959	Discontinued
0.7799	Intermediate Similarity	NPD3750	Approved
0.7792	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1613	Approved
0.7746	Intermediate Similarity	NPD5844	Phase 1
0.7742	Intermediate Similarity	NPD230	Phase 1
0.7742	Intermediate Similarity	NPD447	Suspended
0.773	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6559	Discontinued
0.7658	Intermediate Similarity	NPD1551	Phase 2
0.7625	Intermediate Similarity	NPD2800	Approved
0.7616	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3027	Phase 3
0.7572	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2935	Discontinued
0.7531	Intermediate Similarity	NPD6190	Approved
0.7529	Intermediate Similarity	NPD3749	Approved
0.7516	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7486	Intermediate Similarity	NPD3751	Discontinued
0.7484	Intermediate Similarity	NPD3748	Approved
0.7471	Intermediate Similarity	NPD7768	Phase 2
0.747	Intermediate Similarity	NPD1653	Approved
0.7469	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD9494	Approved
0.7458	Intermediate Similarity	NPD5953	Discontinued
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3226	Approved
0.741	Intermediate Similarity	NPD920	Approved
0.7407	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1243	Approved
0.7394	Intermediate Similarity	NPD2533	Approved
0.7394	Intermediate Similarity	NPD2532	Approved
0.7394	Intermediate Similarity	NPD2534	Approved
0.7391	Intermediate Similarity	NPD2344	Approved
0.7384	Intermediate Similarity	NPD6234	Discontinued
0.7366	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4628	Phase 3
0.7358	Intermediate Similarity	NPD6651	Approved
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7348	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1203	Approved
0.7329	Intermediate Similarity	NPD6099	Approved
0.7329	Intermediate Similarity	NPD6100	Approved
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7322	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7267	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7286	Phase 2
0.7243	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7390	Discontinued
0.7222	Intermediate Similarity	NPD7685	Pre-registration
0.7212	Intermediate Similarity	NPD2309	Approved
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.7193	Intermediate Similarity	NPD37	Approved
0.719	Intermediate Similarity	NPD422	Phase 1
0.7188	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2346	Discontinued
0.7168	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD4967	Phase 2
0.7168	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.712	Intermediate Similarity	NPD8434	Phase 2
0.7107	Intermediate Similarity	NPD6798	Discontinued
0.7107	Intermediate Similarity	NPD3268	Approved
0.7107	Intermediate Similarity	NPD1296	Phase 2
0.7095	Intermediate Similarity	NPD7228	Approved
0.7089	Intermediate Similarity	NPD4908	Phase 1
0.7079	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2403	Approved
0.7078	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1610	Phase 2
0.707	Intermediate Similarity	NPD2798	Approved
0.7063	Intermediate Similarity	NPD6233	Phase 2
0.7063	Intermediate Similarity	NPD4062	Phase 3
0.7055	Intermediate Similarity	NPD7033	Discontinued
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7051	Intermediate Similarity	NPD3225	Approved
0.7048	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1608	Approved
0.7022	Intermediate Similarity	NPD5242	Approved
0.7006	Intermediate Similarity	NPD2797	Approved
0.7006	Intermediate Similarity	NPD2354	Approved
0.7	Intermediate Similarity	NPD411	Approved
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2654	Approved
0.6988	Remote Similarity	NPD1652	Phase 2
0.6987	Remote Similarity	NPD2982	Phase 2
0.6987	Remote Similarity	NPD2983	Phase 2
0.6984	Remote Similarity	NPD4363	Phase 3
0.6984	Remote Similarity	NPD4360	Phase 2
0.6982	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6778	Approved
0.6979	Remote Similarity	NPD6779	Approved
0.6979	Remote Similarity	NPD6776	Approved
0.6979	Remote Similarity	NPD6780	Approved
0.6979	Remote Similarity	NPD6782	Approved
0.6979	Remote Similarity	NPD6781	Approved
0.6979	Remote Similarity	NPD6777	Approved
0.6975	Remote Similarity	NPD6355	Discontinued
0.6974	Remote Similarity	NPD5536	Phase 2
0.6966	Remote Similarity	NPD7229	Phase 3
0.6957	Remote Similarity	NPD8312	Approved
0.6957	Remote Similarity	NPD8313	Approved
0.6939	Remote Similarity	NPD7584	Approved
0.6936	Remote Similarity	NPD6386	Approved
0.6936	Remote Similarity	NPD6385	Approved
0.6935	Remote Similarity	NPD8150	Discontinued
0.6923	Remote Similarity	NPD4357	Discontinued
0.6923	Remote Similarity	NPD2981	Phase 2
0.6914	Remote Similarity	NPD4288	Approved
0.6914	Remote Similarity	NPD5353	Approved
0.6914	Remote Similarity	NPD4060	Phase 1
0.6913	Remote Similarity	NPD228	Approved
0.6906	Remote Similarity	NPD2163	Approved
0.6899	Remote Similarity	NPD3267	Approved
0.6899	Remote Similarity	NPD3266	Approved
0.6897	Remote Similarity	NPD6844	Discontinued
0.6883	Remote Similarity	NPD9268	Approved
0.6882	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5710	Approved
0.6872	Remote Similarity	NPD5711	Approved
0.6872	Remote Similarity	NPD7435	Discontinued
0.6871	Remote Similarity	NPD4340	Discontinued
0.6867	Remote Similarity	NPD3540	Phase 1
0.6867	Remote Similarity	NPD7266	Discontinued
0.6867	Remote Similarity	NPD1471	Phase 3
0.6859	Remote Similarity	NPD4361	Phase 2
0.6859	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1201	Approved
0.6842	Remote Similarity	NPD5049	Phase 3
0.6839	Remote Similarity	NPD17	Approved
0.6836	Remote Similarity	NPD6971	Discontinued
0.6832	Remote Similarity	NPD4625	Phase 3
0.6832	Remote Similarity	NPD7095	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