NPASS Compound

Structure

NPC472438 OpenBabel07101719512D 29 31 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 4.3301 1.5000 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 5.1962 -1.0000 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 1.7321 -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 -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 -2.5981 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 -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 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 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 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 10 21 1 0 0 0 0 11 14 2 0 0 0 0 11 29 1 0 0 0 0 12 19 2 0 0 0 0 12 24 1 0 0 0 0 13 19 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 23 2 0 0 0 0 17 20 2 0 0 0 0 17 29 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.11
Volume:	386.827
LogP:	2.764
LogD:	2.484
LogS:	-4.119
# Rotatable Bonds:	6
TPSA:	116.82
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.639
Synthetic Accessibility Score:	2.57
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.866
MDCK Permeability:	2.6686022465582937e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	77.7383804321289%
Volume Distribution (VD):	0.908
Pgp-substrate:	34.41294479370117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.32
CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.645
CYP2C9-inhibitor:	0.533
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.739
CYP3A4-inhibitor:	0.459
CYP3A4-substrate:	0.489

ADMET: Excretion

Clearance (CL):	4.689
Half-life (T1/2):	0.812

ADMET: Toxicity

hERG Blockers:	0.245
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.186
Rat Oral Acute Toxicity:	0.283
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.471
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.531
Respiratory Toxicity:	0.253

Download Data

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

Natural Product: NPC472438

Natural Product ID:	NPC472438
*Common Name:**	GGNGEESEARSAMF-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GGNGEESEARSAMF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O9/c1-24-12-6-9(7-13(25-2)19(12)27-4)17-20(28-5)16(23)14-11(29-17)8-10(21)18(26-3)15(14)22/h6-8,21-22H,1-5H3
SMILES:	COc1c(OC)cc(cc1OC)c1oc2cc(O)c(c(c2c(=O)c1OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3407503
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002591] 6-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
NPO32817	gardenia oudiepe	Species	Rubiaceae	Eukaryota	flowering buds and leaf bases	Foret Plate, New Caledonia	n.a.	PMID[25659770]
NPO32456	gardenia urvillei	Species	Rubiaceae	Eukaryota	flowering buds and leaf bases	Noumea, New Caledonia	n.a.	PMID[25659770]
NPO32817	gardenia oudiepe	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29207340]

☑ 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	7

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	1
Organism	4
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	78.2	%	PMID[455574]
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	96.1	%	PMID[455574]
NPT319	Cell Line	B16	Mus musculus	IC50	=	91200.0	nM	PMID[455574]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	IC50	=	4540.0	nM	PMID[455575]
NPT518	Protein Complex	Tubulin	Homo sapiens	IC50	=	21400.0	nM	PMID[455574]
NPT518	Protein Complex	Tubulin	Homo sapiens	Inhibition	=	69.9	%	PMID[455574]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	12.5	uM	PMID[455574]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	9650.0	nM	PMID[455574]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	GI	=	13.2	%	PMID[455574]
NPT2229	Organism	Trypanosoma brucei gambiense	Trypanosoma brucei gambiense	GI	=	38.1	%	PMID[455574]
NPT2229	Organism	Trypanosoma brucei gambiense	Trypanosoma brucei gambiense	GI	=	42.9	%	PMID[455574]

☑ 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 NPC472438 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	446
0.1-0.2	1989
0.2-0.3	5134
0.3-0.4	11242
0.4-0.5	6100
0.5-0.6	3997
0.6-0.7	5099
0.7-0.8	4807
0.8-0.85	1914
0.85-0.9	1098
0.9-0.95	653
0.95-1	218

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC29841
1.0	High Similarity	NPC235215
1.0	High Similarity	NPC7973
1.0	High Similarity	NPC78302
0.9933	High Similarity	NPC268161
0.9933	High Similarity	NPC7846
0.9933	High Similarity	NPC25495
0.9933	High Similarity	NPC204854
0.9933	High Similarity	NPC100916
0.9933	High Similarity	NPC200388
0.9933	High Similarity	NPC22472
0.9933	High Similarity	NPC9609
0.9933	High Similarity	NPC288669
0.9933	High Similarity	NPC152166
0.9933	High Similarity	NPC191459
0.9933	High Similarity	NPC143828
0.9933	High Similarity	NPC105242
0.9933	High Similarity	NPC474520
0.9933	High Similarity	NPC115798
0.9933	High Similarity	NPC18607
0.9933	High Similarity	NPC18772
0.9933	High Similarity	NPC130894
0.9933	High Similarity	NPC4481
0.9933	High Similarity	NPC19687
0.9933	High Similarity	NPC55619
0.9933	High Similarity	NPC300943
0.9933	High Similarity	NPC261004
0.9933	High Similarity	NPC176300
0.9933	High Similarity	NPC253634
0.9867	High Similarity	NPC110070
0.9867	High Similarity	NPC227192
0.9867	High Similarity	NPC287979
0.9867	High Similarity	NPC101830
0.9867	High Similarity	NPC203891
0.9867	High Similarity	NPC75215
0.9867	High Similarity	NPC224137
0.9867	High Similarity	NPC305663
0.9867	High Similarity	NPC176665
0.9867	High Similarity	NPC189179
0.9867	High Similarity	NPC93376
0.9867	High Similarity	NPC163524
0.9801	High Similarity	NPC193842
0.98	High Similarity	NPC247017
0.98	High Similarity	NPC245546
0.98	High Similarity	NPC266960
0.98	High Similarity	NPC292107
0.98	High Similarity	NPC49824
0.98	High Similarity	NPC178854
0.98	High Similarity	NPC98661
0.98	High Similarity	NPC43243
0.9799	High Similarity	NPC276409
0.9799	High Similarity	NPC162351
0.9799	High Similarity	NPC58382
0.9799	High Similarity	NPC75279
0.9799	High Similarity	NPC246204
0.9799	High Similarity	NPC250822
0.9737	High Similarity	NPC246478
0.9733	High Similarity	NPC167815
0.9733	High Similarity	NPC201136
0.9733	High Similarity	NPC50715
0.9733	High Similarity	NPC146165
0.9733	High Similarity	NPC2476
0.9733	High Similarity	NPC208197
0.9733	High Similarity	NPC138360
0.9733	High Similarity	NPC280339
0.9733	High Similarity	NPC214138
0.9733	High Similarity	NPC189960
0.9733	High Similarity	NPC163780
0.9733	High Similarity	NPC128863
0.9733	High Similarity	NPC227325
0.9733	High Similarity	NPC26227
0.9733	High Similarity	NPC32557
0.9733	High Similarity	NPC92659
0.9733	High Similarity	NPC183597
0.9733	High Similarity	NPC4455
0.9733	High Similarity	NPC201451
0.9733	High Similarity	NPC196439
0.9733	High Similarity	NPC44079
0.9732	High Similarity	NPC123886
0.9675	High Similarity	NPC470459
0.9669	High Similarity	NPC265511
0.9667	High Similarity	NPC270620
0.9667	High Similarity	NPC69394
0.9667	High Similarity	NPC183878
0.9667	High Similarity	NPC236223
0.9667	High Similarity	NPC255350
0.9667	High Similarity	NPC179126
0.9667	High Similarity	NPC145379
0.9667	High Similarity	NPC78326
0.9667	High Similarity	NPC22519
0.9667	High Similarity	NPC176775
0.9667	High Similarity	NPC231018
0.9667	High Similarity	NPC47781
0.9667	High Similarity	NPC160951
0.9667	High Similarity	NPC274327
0.9667	High Similarity	NPC86485
0.9664	High Similarity	NPC28274
0.9664	High Similarity	NPC133953
0.9664	High Similarity	NPC50403
0.9664	High Similarity	NPC76376
0.9613	High Similarity	NPC470457
0.9603	High Similarity	NPC256612
0.9603	High Similarity	NPC20830
0.9603	High Similarity	NPC213622
0.96	High Similarity	NPC82325
0.96	High Similarity	NPC301323
0.96	High Similarity	NPC156222
0.96	High Similarity	NPC275836
0.96	High Similarity	NPC241498
0.96	High Similarity	NPC162313
0.96	High Similarity	NPC100887
0.96	High Similarity	NPC120163
0.96	High Similarity	NPC239128
0.96	High Similarity	NPC301123
0.96	High Similarity	NPC187498
0.96	High Similarity	NPC293183
0.96	High Similarity	NPC71334
0.96	High Similarity	NPC198826
0.96	High Similarity	NPC131624
0.96	High Similarity	NPC83508
0.96	High Similarity	NPC212678
0.96	High Similarity	NPC222830
0.96	High Similarity	NPC25270
0.96	High Similarity	NPC188203
0.96	High Similarity	NPC57030
0.96	High Similarity	NPC142540
0.96	High Similarity	NPC134677
0.96	High Similarity	NPC279989
0.96	High Similarity	NPC275722
0.96	High Similarity	NPC27208
0.96	High Similarity	NPC256283
0.9597	High Similarity	NPC219330
0.9551	High Similarity	NPC470462
0.9542	High Similarity	NPC195832
0.9533	High Similarity	NPC236769
0.9533	High Similarity	NPC226973
0.9533	High Similarity	NPC225731
0.9533	High Similarity	NPC200740
0.9533	High Similarity	NPC208043
0.9533	High Similarity	NPC125062
0.9533	High Similarity	NPC54394
0.9533	High Similarity	NPC252933
0.953	High Similarity	NPC181250
0.953	High Similarity	NPC177298
0.953	High Similarity	NPC328119
0.953	High Similarity	NPC48479
0.949	High Similarity	NPC76482
0.949	High Similarity	NPC158761
0.949	High Similarity	NPC470456
0.9477	High Similarity	NPC470402
0.947	High Similarity	NPC39732
0.947	High Similarity	NPC60972
0.947	High Similarity	NPC55205
0.9467	High Similarity	NPC149127
0.9467	High Similarity	NPC188871
0.9467	High Similarity	NPC306821
0.9467	High Similarity	NPC201547
0.9467	High Similarity	NPC184136
0.9467	High Similarity	NPC259058
0.9467	High Similarity	NPC286342
0.9467	High Similarity	NPC50728
0.9467	High Similarity	NPC166753
0.9467	High Similarity	NPC77858
0.9463	High Similarity	NPC120464
0.943	High Similarity	NPC280493
0.9423	High Similarity	NPC41301
0.9416	High Similarity	NPC152904
0.9412	High Similarity	NPC472916
0.9408	High Similarity	NPC280937
0.9408	High Similarity	NPC250557
0.9404	High Similarity	NPC308451
0.9404	High Similarity	NPC260895
0.94	High Similarity	NPC296197
0.94	High Similarity	NPC216318
0.94	High Similarity	NPC17286
0.94	High Similarity	NPC137062
0.94	High Similarity	NPC195351
0.94	High Similarity	NPC270465
0.94	High Similarity	NPC159103
0.94	High Similarity	NPC183950
0.94	High Similarity	NPC69752
0.94	High Similarity	NPC259713
0.94	High Similarity	NPC52005
0.94	High Similarity	NPC223579
0.94	High Similarity	NPC87125
0.94	High Similarity	NPC287101
0.9396	High Similarity	NPC55557
0.9396	High Similarity	NPC30647
0.9396	High Similarity	NPC62536
0.9396	High Similarity	NPC61871
0.9396	High Similarity	NPC33265
0.9367	High Similarity	NPC295082
0.9355	High Similarity	NPC476980
0.9355	High Similarity	NPC263449
0.9351	High Similarity	NPC475267
0.9351	High Similarity	NPC471479
0.9351	High Similarity	NPC472910
0.9351	High Similarity	NPC48208
0.9351	High Similarity	NPC300727
0.9351	High Similarity	NPC474208

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 NPC472438 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	1001
0.2-0.3	1970
0.3-0.4	2676
0.4-0.5	1676
0.5-0.6	947
0.6-0.7	309
0.7-0.8	107
0.8-0.85	26
0.85-0.9	15
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9667	High Similarity	NPD2801	Approved
0.9286	High Similarity	NPD3882	Suspended
0.9221	High Similarity	NPD3817	Phase 2
0.92	High Similarity	NPD1512	Approved
0.9091	High Similarity	NPD1934	Approved
0.908	High Similarity	NPD4338	Clinical (unspecified phase)
0.9067	High Similarity	NPD1511	Approved
0.9	High Similarity	NPD6166	Phase 2
0.9	High Similarity	NPD6168	Clinical (unspecified phase)
0.9	High Similarity	NPD6167	Clinical (unspecified phase)
0.891	High Similarity	NPD2393	Clinical (unspecified phase)
0.8841	High Similarity	NPD6797	Phase 2
0.8788	High Similarity	NPD7251	Discontinued
0.8773	High Similarity	NPD3818	Discontinued
0.8758	High Similarity	NPD4378	Clinical (unspecified phase)
0.8735	High Similarity	NPD7808	Phase 3
0.872	High Similarity	NPD7054	Approved
0.8667	High Similarity	NPD7472	Approved
0.8616	High Similarity	NPD5402	Approved
0.8562	High Similarity	NPD4868	Clinical (unspecified phase)
0.8554	High Similarity	NPD7074	Phase 3
0.8509	High Similarity	NPD7075	Discontinued
0.8452	Intermediate Similarity	NPD6799	Approved
0.8405	Intermediate Similarity	NPD5494	Approved
0.8375	Intermediate Similarity	NPD6801	Discontinued
0.8365	Intermediate Similarity	NPD4380	Phase 2
0.8354	Intermediate Similarity	NPD1247	Approved
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6232	Discontinued
0.8284	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7473	Discontinued
0.821	Intermediate Similarity	NPD1465	Phase 2
0.8182	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5403	Approved
0.817	Intermediate Similarity	NPD1510	Phase 2
0.8165	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD3926	Phase 2
0.8137	Intermediate Similarity	NPD6599	Discontinued
0.8129	Intermediate Similarity	NPD1549	Phase 2
0.8117	Intermediate Similarity	NPD2796	Approved
0.805	Intermediate Similarity	NPD5401	Approved
0.8026	Intermediate Similarity	NPD943	Approved
0.8026	Intermediate Similarity	NPD1240	Approved
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD919	Approved
0.7988	Intermediate Similarity	NPD7819	Suspended
0.7953	Intermediate Similarity	NPD5844	Phase 1
0.7939	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1607	Approved
0.7917	Intermediate Similarity	NPD6959	Discontinued
0.7866	Intermediate Similarity	NPD7411	Suspended
0.7862	Intermediate Similarity	NPD6190	Approved
0.7857	Intermediate Similarity	NPD230	Phase 1
0.7821	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7763	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD447	Suspended
0.7736	Intermediate Similarity	NPD2800	Approved
0.773	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6559	Discontinued
0.7688	Intermediate Similarity	NPD3750	Approved
0.7688	Intermediate Similarity	NPD3751	Discontinued
0.7683	Intermediate Similarity	NPD1653	Approved
0.7677	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1613	Approved
0.7661	Intermediate Similarity	NPD3787	Discontinued
0.7624	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2532	Approved
0.7607	Intermediate Similarity	NPD2534	Approved
0.7607	Intermediate Similarity	NPD2533	Approved
0.7597	Intermediate Similarity	NPD3027	Phase 3
0.7588	Intermediate Similarity	NPD6234	Discontinued
0.7572	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1551	Phase 2
0.7542	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7471	Intermediate Similarity	NPD7768	Phase 2
0.7469	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD9494	Approved
0.7468	Intermediate Similarity	NPD6651	Approved
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6100	Approved
0.7438	Intermediate Similarity	NPD6099	Approved
0.7434	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3226	Approved
0.741	Intermediate Similarity	NPD920	Approved
0.7407	Intermediate Similarity	NPD1243	Approved
0.7407	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1933	Approved
0.7396	Intermediate Similarity	NPD37	Approved
0.7391	Intermediate Similarity	NPD2344	Approved
0.7389	Intermediate Similarity	NPD6233	Phase 2
0.7375	Intermediate Similarity	NPD3748	Approved
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2403	Approved
0.7368	Intermediate Similarity	NPD4966	Approved
0.7368	Intermediate Similarity	NPD4965	Approved
0.7368	Intermediate Similarity	NPD4967	Phase 2
0.7366	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4628	Phase 3
0.736	Intermediate Similarity	NPD5953	Discontinued
0.7333	Intermediate Similarity	NPD7390	Discontinued
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7318	Intermediate Similarity	NPD7685	Pre-registration
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7289	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2799	Discontinued
0.7255	Intermediate Similarity	NPD9269	Phase 2
0.7249	Intermediate Similarity	NPD6777	Approved
0.7249	Intermediate Similarity	NPD6776	Approved
0.7249	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD6778	Approved
0.7249	Intermediate Similarity	NPD6781	Approved
0.7249	Intermediate Similarity	NPD6779	Approved
0.7249	Intermediate Similarity	NPD6780	Approved
0.7247	Intermediate Similarity	NPD7286	Phase 2
0.7226	Intermediate Similarity	NPD1203	Approved
0.7225	Intermediate Similarity	NPD7435	Discontinued
0.7215	Intermediate Similarity	NPD6798	Discontinued
0.7212	Intermediate Similarity	NPD2309	Approved
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.7193	Intermediate Similarity	NPD6844	Discontinued
0.7186	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2346	Discontinued
0.7175	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1548	Phase 1
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.712	Intermediate Similarity	NPD8150	Discontinued
0.7119	Intermediate Similarity	NPD5242	Approved
0.711	Intermediate Similarity	NPD5353	Approved
0.7107	Intermediate Similarity	NPD3268	Approved
0.7091	Intermediate Similarity	NPD2654	Approved
0.7089	Intermediate Similarity	NPD4908	Phase 1
0.7081	Intermediate Similarity	NPD6355	Discontinued
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD422	Phase 1
0.707	Intermediate Similarity	NPD2798	Approved
0.7062	Intermediate Similarity	NPD5710	Approved
0.7062	Intermediate Similarity	NPD5711	Approved
0.7055	Intermediate Similarity	NPD7033	Discontinued
0.7049	Intermediate Similarity	NPD8312	Approved
0.7049	Intermediate Similarity	NPD8313	Approved
0.7047	Intermediate Similarity	NPD7696	Phase 3
0.7047	Intermediate Similarity	NPD7698	Approved
0.7047	Intermediate Similarity	NPD7697	Approved
0.7035	Intermediate Similarity	NPD6386	Approved
0.7035	Intermediate Similarity	NPD6385	Approved
0.7032	Intermediate Similarity	NPD9717	Approved
0.7024	Intermediate Similarity	NPD4357	Discontinued
0.7019	Intermediate Similarity	NPD4060	Phase 1
0.701	Intermediate Similarity	NPD7870	Phase 2
0.701	Intermediate Similarity	NPD7871	Phase 2
0.7006	Intermediate Similarity	NPD2797	Approved
0.7006	Intermediate Similarity	NPD2354	Approved
0.7005	Intermediate Similarity	NPD7874	Approved
0.7005	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2163	Approved
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD9268	Approved
0.699	Remote Similarity	NPD7701	Phase 2
0.6987	Remote Similarity	NPD2983	Phase 2
0.6987	Remote Similarity	NPD2982	Phase 2
0.6984	Remote Similarity	NPD4363	Phase 3
0.6984	Remote Similarity	NPD6534	Approved
0.6984	Remote Similarity	NPD4360	Phase 2
0.6984	Remote Similarity	NPD6535	Approved
0.6974	Remote Similarity	NPD5536	Phase 2
0.697	Remote Similarity	NPD1471	Phase 3
0.6968	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1610	Phase 2
0.6954	Remote Similarity	NPD8151	Discontinued
0.6951	Remote Similarity	NPD4308	Phase 3
0.6943	Remote Similarity	NPD3225	Approved
0.6939	Remote Similarity	NPD7584	Approved
0.6937	Remote Similarity	NPD7095	Approved
0.6923	Remote Similarity	NPD2981	Phase 2
0.6923	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD2861	Phase 2
0.6912	Remote Similarity	NPD7907	Approved
0.6902	Remote Similarity	NPD7549	Discontinued
0.6897	Remote Similarity	NPD2899	Discontinued
0.6894	Remote Similarity	NPD411	Approved
0.6886	Remote Similarity	NPD1652	Phase 2
0.6884	Remote Similarity	NPD7783	Phase 2
0.6884	Remote Similarity	NPD7801	Approved
0.6884	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7004	Clinical (unspecified phase)

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