NPASS Compound

Structure

CID63187 OpenBabel06191715402D 27 29 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 1.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -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 -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 -1.7321 -2.0000 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 -1.5000 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 -0.5000 0.0000 C 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 -3.4641 -0.0000 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 -1.7321 -3.0000 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 9 1 0 0 0 0 2 9 1 0 0 0 0 3 5 1 0 0 0 0 3 9 2 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 20 2 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 25 2 0 0 0 0 18 19 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.11
Volume:	366.61
LogP:	4.179
LogD:	2.274
LogS:	-3.338
# Rotatable Bonds:	3
TPSA:	131.36
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	2.917
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.107
MDCK Permeability:	1.0724861567723565e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.858
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	94.40367889404297%
Volume Distribution (VD):	0.648
Pgp-substrate:	7.258338451385498%

ADMET: Metabolism

CYP1A2-inhibitor:	0.902
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.184
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.703
CYP2C9-substrate:	0.432
CYP2D6-inhibitor:	0.404
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.142
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	9.141
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.542
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.773
Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.89
Carcinogencity:	0.077
Eye Corrosion:	0.003
Eye Irritation:	0.906
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC63187

Natural Product ID:	NPC63187
*Common Name:**	8-Prenylquercetin
IUPAC Name:	2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-(3-methylbut-2-enyl)chromen-4-one
Synonyms:	8-Prenylquercetin
Standard InCHIKey:	ZHTTWVRMGWQEOH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O7/c1-9(2)3-5-11-13(22)8-15(24)16-17(25)18(26)19(27-20(11)16)10-4-6-12(21)14(23)7-10/h3-4,6-8,21-24,26H,5H2,1-2H3
SMILES:	CC(=CCc1c(O)cc(c2c1oc(c1ccc(c(c1)O)O)c(c2=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL193059
PubChem CID:	9799499
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-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
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26359402]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	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	2
Others	3

Activity Type	# Activity
Cell Line	3
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	68.0	n.a.	PMID[522490]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	67.0	n.a.	PMID[522490]
NPT139	Cell Line	HT-29	Homo sapiens	Caspase induction	=	1.9	n.a.	PMID[522490]
NPT273	Individual Protein	Phosphodiesterase 5A	Homo sapiens	IC50	=	700.0	nM	PMID[522491]
NPT2	Others	Unspecified		IC50	=	4380.0	nM	PMID[522492]

☑ 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 NPC63187 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	445
0.1-0.2	1966
0.2-0.3	4948
0.3-0.4	11310
0.4-0.5	6064
0.5-0.6	3839
0.6-0.7	4943
0.7-0.8	4723
0.8-0.85	2216
0.85-0.9	1362
0.9-0.95	632
0.95-1	249

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC157784
1.0	High Similarity	NPC37684
0.9931	High Similarity	NPC205046
0.9931	High Similarity	NPC304295
0.9931	High Similarity	NPC59162
0.9864	High Similarity	NPC133392
0.9862	High Similarity	NPC88804
0.9862	High Similarity	NPC3825
0.9797	High Similarity	NPC3980
0.9732	High Similarity	NPC237418
0.9732	High Similarity	NPC273843
0.9664	High Similarity	NPC475799
0.9664	High Similarity	NPC13779
0.9662	High Similarity	NPC170492
0.966	High Similarity	NPC154345
0.9658	High Similarity	NPC87125
0.9658	High Similarity	NPC270465
0.9595	High Similarity	NPC249570
0.9595	High Similarity	NPC471982
0.9592	High Similarity	NPC188871
0.9592	High Similarity	NPC286342
0.9592	High Similarity	NPC149127
0.9586	High Similarity	NPC20791
0.9586	High Similarity	NPC179271
0.9536	High Similarity	NPC22192
0.9533	High Similarity	NPC471985
0.9533	High Similarity	NPC276444
0.953	High Similarity	NPC236223
0.953	High Similarity	NPC179126
0.953	High Similarity	NPC476631
0.953	High Similarity	NPC192083
0.953	High Similarity	NPC189130
0.953	High Similarity	NPC213896
0.953	High Similarity	NPC78326
0.953	High Similarity	NPC270620
0.9527	High Similarity	NPC125062
0.9527	High Similarity	NPC252933
0.9527	High Similarity	NPC54394
0.9527	High Similarity	NPC200740
0.9527	High Similarity	NPC260895
0.9521	High Similarity	NPC108406
0.9521	High Similarity	NPC74881
0.9521	High Similarity	NPC51443
0.9477	High Similarity	NPC78332
0.9474	High Similarity	NPC282009
0.9474	High Similarity	NPC287328
0.9474	High Similarity	NPC246478
0.947	High Similarity	NPC476630
0.947	High Similarity	NPC218871
0.9467	High Similarity	NPC472280
0.9467	High Similarity	NPC80534
0.9467	High Similarity	NPC234255
0.9467	High Similarity	NPC321779
0.9467	High Similarity	NPC56786
0.9463	High Similarity	NPC82325
0.9463	High Similarity	NPC279989
0.9463	High Similarity	NPC106976
0.9463	High Similarity	NPC55205
0.9463	High Similarity	NPC237994
0.9459	High Similarity	NPC50728
0.9459	High Similarity	NPC166753
0.9452	High Similarity	NPC169749
0.9448	High Similarity	NPC279121
0.9448	High Similarity	NPC24821
0.9448	High Similarity	NPC293053
0.9448	High Similarity	NPC212932
0.9448	High Similarity	NPC9117
0.9448	High Similarity	NPC190637
0.9416	High Similarity	NPC472625
0.9412	High Similarity	NPC187354
0.9412	High Similarity	NPC471499
0.9412	High Similarity	NPC289771
0.9408	High Similarity	NPC46736
0.9408	High Similarity	NPC197856
0.9404	High Similarity	NPC170026
0.9404	High Similarity	NPC265511
0.9404	High Similarity	NPC68093
0.9404	High Similarity	NPC291878
0.9404	High Similarity	NPC49824
0.9404	High Similarity	NPC472455
0.9404	High Similarity	NPC191146
0.9404	High Similarity	NPC278778
0.9404	High Similarity	NPC35038
0.9404	High Similarity	NPC282307
0.9404	High Similarity	NPC471500
0.9404	High Similarity	NPC195796
0.94	High Similarity	NPC33051
0.94	High Similarity	NPC227337
0.94	High Similarity	NPC273462
0.94	High Similarity	NPC298692
0.94	High Similarity	NPC162351
0.94	High Similarity	NPC74924
0.94	High Similarity	NPC49402
0.94	High Similarity	NPC58382
0.94	High Similarity	NPC70433
0.9396	High Similarity	NPC236769
0.9396	High Similarity	NPC133953
0.9396	High Similarity	NPC28274
0.9396	High Similarity	NPC50403
0.9392	High Similarity	NPC48479
0.9392	High Similarity	NPC195351
0.9392	High Similarity	NPC159103
0.9392	High Similarity	NPC137062
0.9392	High Similarity	NPC183950
0.9392	High Similarity	NPC177298
0.9392	High Similarity	NPC223579
0.9392	High Similarity	NPC52005
0.9392	High Similarity	NPC287101
0.9392	High Similarity	NPC38545
0.9392	High Similarity	NPC171916
0.9392	High Similarity	NPC269420
0.9384	High Similarity	NPC326500
0.9384	High Similarity	NPC216538
0.9384	High Similarity	NPC273538
0.9384	High Similarity	NPC70136
0.9379	High Similarity	NPC473042
0.9379	High Similarity	NPC175013
0.9379	High Similarity	NPC200694
0.9346	High Similarity	NPC476283
0.9346	High Similarity	NPC118256
0.9346	High Similarity	NPC470326
0.9346	High Similarity	NPC192686
0.9346	High Similarity	NPC328102
0.9346	High Similarity	NPC204290
0.9346	High Similarity	NPC476980
0.9346	High Similarity	NPC297212
0.9346	High Similarity	NPC476280
0.9346	High Similarity	NPC119209
0.9342	High Similarity	NPC75215
0.9342	High Similarity	NPC224137
0.9342	High Similarity	NPC27337
0.9342	High Similarity	NPC67876
0.9342	High Similarity	NPC472598
0.9342	High Similarity	NPC78225
0.9342	High Similarity	NPC189179
0.9342	High Similarity	NPC471479
0.9342	High Similarity	NPC93376
0.9342	High Similarity	NPC110070
0.9342	High Similarity	NPC227192
0.9342	High Similarity	NPC474681
0.9342	High Similarity	NPC203891
0.9342	High Similarity	NPC218313
0.9342	High Similarity	NPC101830
0.9342	High Similarity	NPC471515
0.9342	High Similarity	NPC474055
0.9342	High Similarity	NPC291508
0.9342	High Similarity	NPC471209
0.9338	High Similarity	NPC477503
0.9338	High Similarity	NPC44079
0.9338	High Similarity	NPC26227
0.9338	High Similarity	NPC470327
0.9338	High Similarity	NPC168247
0.9338	High Similarity	NPC214138
0.9338	High Similarity	NPC45849
0.9338	High Similarity	NPC200761
0.9338	High Similarity	NPC117992
0.9338	High Similarity	NPC230149
0.9338	High Similarity	NPC152951
0.9338	High Similarity	NPC57674
0.9338	High Similarity	NPC201451
0.9338	High Similarity	NPC113906
0.9333	High Similarity	NPC123886
0.9333	High Similarity	NPC324233
0.9333	High Similarity	NPC60972
0.9333	High Similarity	NPC39732
0.9333	High Similarity	NPC323626
0.9329	High Similarity	NPC219330
0.9329	High Similarity	NPC184136
0.9329	High Similarity	NPC77858
0.9324	High Similarity	NPC120464
0.9324	High Similarity	NPC238279
0.9324	High Similarity	NPC261548
0.9324	High Similarity	NPC166036
0.9324	High Similarity	NPC119059
0.9324	High Similarity	NPC203077
0.9324	High Similarity	NPC195202
0.932	High Similarity	NPC5820
0.932	High Similarity	NPC124729
0.932	High Similarity	NPC178343
0.932	High Similarity	NPC306488
0.929	High Similarity	NPC470459
0.9286	High Similarity	NPC474038
0.9286	High Similarity	NPC167678
0.9286	High Similarity	NPC26326
0.9286	High Similarity	NPC198829
0.9286	High Similarity	NPC29876
0.9286	High Similarity	NPC259456
0.9286	High Similarity	NPC258331
0.9281	High Similarity	NPC74178
0.9281	High Similarity	NPC204879
0.9281	High Similarity	NPC18772
0.9281	High Similarity	NPC105242
0.9281	High Similarity	NPC9609
0.9281	High Similarity	NPC210459
0.9281	High Similarity	NPC204854
0.9281	High Similarity	NPC115798
0.9281	High Similarity	NPC191459
0.9281	High Similarity	NPC176300
0.9281	High Similarity	NPC7846
0.9281	High Similarity	NPC185258

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 NPC63187 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	421
0.1-0.2	994
0.2-0.3	1790
0.3-0.4	2696
0.4-0.5	1738
0.5-0.6	990
0.6-0.7	350
0.7-0.8	111
0.8-0.85	40
0.85-0.9	10
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9586	High Similarity	NPD1512	Approved
0.953	High Similarity	NPD2393	Clinical (unspecified phase)
0.9448	High Similarity	NPD1511	Approved
0.9384	High Similarity	NPD4378	Clinical (unspecified phase)
0.9272	High Similarity	NPD2801	Approved
0.9205	High Similarity	NPD1934	Approved
0.9026	High Similarity	NPD3882	Suspended
0.8987	High Similarity	NPD6166	Phase 2
0.8987	High Similarity	NPD6168	Clinical (unspecified phase)
0.8987	High Similarity	NPD6167	Clinical (unspecified phase)
0.8961	High Similarity	NPD3817	Phase 2
0.8742	High Similarity	NPD7410	Clinical (unspecified phase)
0.8726	High Similarity	NPD7075	Discontinued
0.8712	High Similarity	NPD6797	Phase 2
0.8701	High Similarity	NPD4380	Phase 2
0.8659	High Similarity	NPD7251	Discontinued
0.8654	High Similarity	NPD7096	Clinical (unspecified phase)
0.8642	High Similarity	NPD3818	Discontinued
0.859	High Similarity	NPD6801	Discontinued
0.8589	High Similarity	NPD7054	Approved
0.8537	High Similarity	NPD7074	Phase 3
0.8537	High Similarity	NPD7472	Approved
0.8523	High Similarity	NPD1550	Clinical (unspecified phase)
0.8523	High Similarity	NPD1552	Clinical (unspecified phase)
0.8514	High Similarity	NPD1510	Phase 2
0.8494	Intermediate Similarity	NPD7808	Phase 3
0.8494	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1549	Phase 2
0.8456	Intermediate Similarity	NPD2796	Approved
0.8431	Intermediate Similarity	NPD6799	Approved
0.8428	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD7819	Suspended
0.8395	Intermediate Similarity	NPD6232	Discontinued
0.8385	Intermediate Similarity	NPD5494	Approved
0.8375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD943	Approved
0.8367	Intermediate Similarity	NPD1240	Approved
0.8365	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7473	Discontinued
0.8291	Intermediate Similarity	NPD7411	Suspended
0.8255	Intermediate Similarity	NPD1607	Approved
0.8228	Intermediate Similarity	NPD6599	Discontinued
0.8221	Intermediate Similarity	NPD6959	Discontinued
0.8221	Intermediate Similarity	NPD1247	Approved
0.821	Intermediate Similarity	NPD919	Approved
0.817	Intermediate Similarity	NPD2800	Approved
0.8155	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5402	Approved
0.8117	Intermediate Similarity	NPD3750	Approved
0.8105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2935	Discontinued
0.8075	Intermediate Similarity	NPD1465	Phase 2
0.8038	Intermediate Similarity	NPD5403	Approved
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8027	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD6559	Discontinued
0.7975	Intermediate Similarity	NPD7768	Phase 2
0.7964	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1243	Approved
0.7911	Intermediate Similarity	NPD2532	Approved
0.7911	Intermediate Similarity	NPD2534	Approved
0.7911	Intermediate Similarity	NPD5401	Approved
0.7911	Intermediate Similarity	NPD2533	Approved
0.7881	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1613	Approved
0.7867	Intermediate Similarity	NPD2313	Discontinued
0.7829	Intermediate Similarity	NPD230	Phase 1
0.7826	Intermediate Similarity	NPD3226	Approved
0.7818	Intermediate Similarity	NPD3749	Approved
0.7812	Intermediate Similarity	NPD920	Approved
0.7792	Intermediate Similarity	NPD2799	Discontinued
0.7792	Intermediate Similarity	NPD3748	Approved
0.7792	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6651	Approved
0.7748	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1551	Phase 2
0.7742	Intermediate Similarity	NPD6100	Approved
0.7742	Intermediate Similarity	NPD6099	Approved
0.7736	Intermediate Similarity	NPD7390	Discontinued
0.7712	Intermediate Similarity	NPD447	Suspended
0.7702	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2344	Approved
0.7692	Intermediate Similarity	NPD2346	Discontinued
0.7688	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3027	Phase 3
0.7673	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5953	Discontinued
0.7616	Intermediate Similarity	NPD7286	Phase 2
0.7588	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7547	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1203	Approved
0.7527	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3268	Approved
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2798	Approved
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7457	Intermediate Similarity	NPD3751	Discontinued
0.7456	Intermediate Similarity	NPD6234	Discontinued
0.7451	Intermediate Similarity	NPD4625	Phase 3
0.7427	Intermediate Similarity	NPD3787	Discontinued
0.7418	Intermediate Similarity	NPD4360	Phase 2
0.7418	Intermediate Similarity	NPD4363	Phase 3
0.7417	Intermediate Similarity	NPD2797	Approved
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4908	Phase 1
0.7383	Intermediate Similarity	NPD422	Phase 1
0.7372	Intermediate Similarity	NPD1933	Approved
0.7362	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1548	Phase 1
0.7342	Intermediate Similarity	NPD7033	Discontinued
0.7342	Intermediate Similarity	NPD4308	Phase 3
0.7333	Intermediate Similarity	NPD9269	Phase 2
0.7333	Intermediate Similarity	NPD1653	Approved
0.7333	Intermediate Similarity	NPD9717	Approved
0.7333	Intermediate Similarity	NPD1608	Approved
0.7326	Intermediate Similarity	NPD5711	Approved
0.7326	Intermediate Similarity	NPD5710	Approved
0.732	Intermediate Similarity	NPD9494	Approved
0.7308	Intermediate Similarity	NPD4060	Phase 1
0.729	Intermediate Similarity	NPD6798	Discontinued
0.7283	Intermediate Similarity	NPD4361	Phase 2
0.7283	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7267	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD1201	Approved
0.7267	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD37	Approved
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1471	Phase 3
0.7241	Intermediate Similarity	NPD2403	Approved
0.7237	Intermediate Similarity	NPD3225	Approved
0.7235	Intermediate Similarity	NPD4967	Phase 2
0.7235	Intermediate Similarity	NPD4965	Approved
0.7235	Intermediate Similarity	NPD4966	Approved
0.7225	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6779	Approved
0.7219	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD6778	Approved
0.7219	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD6782	Approved
0.7219	Intermediate Similarity	NPD6776	Approved
0.7212	Intermediate Similarity	NPD5049	Phase 3
0.7207	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD8312	Approved
0.7202	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1470	Approved
0.719	Intermediate Similarity	NPD3267	Approved
0.719	Intermediate Similarity	NPD3266	Approved
0.7188	Intermediate Similarity	NPD5408	Approved
0.7188	Intermediate Similarity	NPD5404	Approved
0.7188	Intermediate Similarity	NPD5406	Approved
0.7188	Intermediate Similarity	NPD5405	Approved
0.7182	Intermediate Similarity	NPD8150	Discontinued
0.7179	Intermediate Similarity	NPD411	Approved
0.7178	Intermediate Similarity	NPD2354	Approved
0.7176	Intermediate Similarity	NPD4288	Approved
0.7173	Intermediate Similarity	NPD7584	Approved
0.7171	Intermediate Similarity	NPD4749	Approved
0.716	Intermediate Similarity	NPD2654	Approved
0.7159	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3300	Phase 2
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7133	Intermediate Similarity	NPD17	Approved
0.7115	Intermediate Similarity	NPD7095	Approved
0.7105	Intermediate Similarity	NPD7435	Discontinued
0.7095	Intermediate Similarity	NPD7685	Pre-registration
0.7089	Intermediate Similarity	NPD4307	Phase 2
0.7086	Intermediate Similarity	NPD5242	Approved
0.7083	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7458	Discontinued
0.7079	Intermediate Similarity	NPD1729	Discontinued
0.707	Intermediate Similarity	NPD1296	Phase 2
0.7067	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD6844	Discontinued
0.7045	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7697	Approved
0.7016	Intermediate Similarity	NPD7696	Phase 3
0.7016	Intermediate Similarity	NPD7698	Approved
0.701	Intermediate Similarity	NPD8151	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