NPASS Compound

Structure

NPC25427 OpenBabel07101718202D 23 25 0 0 0 0 0 0 0 0999 V2000 -4.3301 2.5000 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 1.7321 -2.0000 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 -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 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 -0.8660 -0.5000 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 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 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 0.0000 -0.0000 0.0000 C 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 -2.5981 -1.5000 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 7 2 0 0 0 0 2 12 1 0 0 0 0 3 7 1 0 0 0 0 3 14 2 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 10 1 0 0 0 0 5 13 2 0 0 0 0 6 9 2 0 0 0 0 6 23 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 11 13 1 0 0 0 0 11 19 2 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 16 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.04
Volume:	297.426
LogP:	1.681
LogD:	1.715
LogS:	-3.777
# Rotatable Bonds:	2
TPSA:	114.04
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.802
Synthetic Accessibility Score:	2.948
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.1
MDCK Permeability:	1.676832471275702e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.095
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.146

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	90.84166717529297%
Volume Distribution (VD):	0.41
Pgp-substrate:	6.811251640319824%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.673
CYP2C19-inhibitor:	0.709
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.872
CYP2D6-inhibitor:	0.905
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.74
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	3.613
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.837
Drug-inuced Liver Injury (DILI):	0.518
AMES Toxicity:	0.36
Rat Oral Acute Toxicity:	0.888
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.821
Carcinogencity:	0.843
Eye Corrosion:	0.02
Eye Irritation:	0.707
Respiratory Toxicity:	0.517

Download Data

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

Natural Product: NPC25427

Natural Product ID:	NPC25427
*Common Name:**	5-Hydroxybowdichione
IUPAC Name:	2-(5,7-dihydroxy-4-oxochromen-3-yl)-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:	5-Hydroxybowdichione
Standard InCHIKey:	XTAGXYXCZYACHC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H10O7/c1-22-13-5-10(18)8(4-11(13)19)9-6-23-14-3-7(17)2-12(20)15(14)16(9)21/h2-6,17,20H,1H3
SMILES:	COC1=CC(=O)C(=CC1=O)c1coc2cc(cc(c2c1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478972
PubChem CID:	5491730
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19653666]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	Thai	n.a.	PMID[3430167]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	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
MIC	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[521915]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	100.0	ug.mL-1	PMID[521915]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	50.0	ug.mL-1	PMID[521915]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[521915]
NPT3086	Organism	Penicillium expansum	Penicillium expansum	MIC	>	100.0	ug.mL-1	PMID[521915]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	100.0	ug.mL-1	PMID[521915]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	100.0	ug.mL-1	PMID[521915]

☑ 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 NPC25427 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	383
0.1-0.2	1769
0.2-0.3	4853
0.3-0.4	10993
0.4-0.5	7154
0.5-0.6	4586
0.6-0.7	5555
0.7-0.8	4270
0.8-0.85	2159
0.85-0.9	886
0.9-0.95	87
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC49242
0.9338	High Similarity	NPC294409
0.9338	High Similarity	NPC162680
0.9338	High Similarity	NPC7013
0.9338	High Similarity	NPC181124
0.9338	High Similarity	NPC116632
0.9338	High Similarity	NPC303644
0.9338	High Similarity	NPC209560
0.9323	High Similarity	NPC65060
0.927	High Similarity	NPC12175
0.927	High Similarity	NPC279668
0.927	High Similarity	NPC309154
0.927	High Similarity	NPC278323
0.927	High Similarity	NPC90665
0.927	High Similarity	NPC55162
0.9214	High Similarity	NPC473813
0.9214	High Similarity	NPC473812
0.9209	High Similarity	NPC136840
0.9203	High Similarity	NPC295384
0.9191	High Similarity	NPC234560
0.9191	High Similarity	NPC39426
0.9173	High Similarity	NPC185497
0.9149	High Similarity	NPC472446
0.9149	High Similarity	NPC472447
0.9137	High Similarity	NPC59951
0.9137	High Similarity	NPC48624
0.9137	High Similarity	NPC219917
0.9137	High Similarity	NPC204985
0.9137	High Similarity	NPC269652
0.9137	High Similarity	NPC213659
0.9137	High Similarity	NPC259166
0.9137	High Similarity	NPC184536
0.9137	High Similarity	NPC103904
0.9137	High Similarity	NPC172250
0.9137	High Similarity	NPC253822
0.9137	High Similarity	NPC146679
0.9137	High Similarity	NPC103342
0.9137	High Similarity	NPC281207
0.9137	High Similarity	NPC230285
0.9137	High Similarity	NPC101366
0.9137	High Similarity	NPC215311
0.9137	High Similarity	NPC144118
0.9137	High Similarity	NPC80962
0.9137	High Similarity	NPC326109
0.9124	High Similarity	NPC87545
0.9124	High Similarity	NPC235428
0.9124	High Similarity	NPC193792
0.9118	High Similarity	NPC286336
0.9111	High Similarity	NPC257756
0.9111	High Similarity	NPC205468
0.9111	High Similarity	NPC129132
0.9111	High Similarity	NPC87231
0.9111	High Similarity	NPC212631
0.9098	High Similarity	NPC212379
0.9098	High Similarity	NPC60558
0.9098	High Similarity	NPC69235
0.9091	High Similarity	NPC128428
0.9091	High Similarity	NPC305518
0.9085	High Similarity	NPC470458
0.9078	High Similarity	NPC158874
0.9071	High Similarity	NPC52789
0.9071	High Similarity	NPC90582
0.9071	High Similarity	NPC26051
0.9071	High Similarity	NPC469404
0.9071	High Similarity	NPC262094
0.9071	High Similarity	NPC55832
0.9071	High Similarity	NPC268204
0.9065	High Similarity	NPC469523
0.9065	High Similarity	NPC283429
0.9065	High Similarity	NPC241838
0.9065	High Similarity	NPC143799
0.9065	High Similarity	NPC152042
0.9058	High Similarity	NPC250266
0.9058	High Similarity	NPC212767
0.9058	High Similarity	NPC266597
0.9051	High Similarity	NPC60667
0.9044	High Similarity	NPC82225
0.9044	High Similarity	NPC242294
0.9044	High Similarity	NPC56031
0.9044	High Similarity	NPC337373
0.9044	High Similarity	NPC18877
0.9044	High Similarity	NPC204960
0.9044	High Similarity	NPC28753
0.9044	High Similarity	NPC20560
0.9044	High Similarity	NPC263670
0.9044	High Similarity	NPC192304
0.9044	High Similarity	NPC294593
0.9044	High Similarity	NPC159623
0.9044	High Similarity	NPC144051
0.9044	High Similarity	NPC472365
0.9044	High Similarity	NPC188646
0.9044	High Similarity	NPC223457
0.9044	High Similarity	NPC312318
0.9044	High Similarity	NPC139813
0.9044	High Similarity	NPC175098
0.9037	High Similarity	NPC31872
0.9037	High Similarity	NPC473584
0.9037	High Similarity	NPC64359
0.9037	High Similarity	NPC308037
0.9037	High Similarity	NPC262359
0.9037	High Similarity	NPC475589
0.9037	High Similarity	NPC313618
0.9023	High Similarity	NPC186098
0.9023	High Similarity	NPC80694
0.9007	High Similarity	NPC204469
0.8993	High Similarity	NPC188947
0.8993	High Similarity	NPC99333
0.8993	High Similarity	NPC124269
0.8993	High Similarity	NPC280284
0.8986	High Similarity	NPC150399
0.8986	High Similarity	NPC274109
0.8986	High Similarity	NPC240147
0.8986	High Similarity	NPC477243
0.8986	High Similarity	NPC124784
0.8986	High Similarity	NPC121243
0.8986	High Similarity	NPC25287
0.8986	High Similarity	NPC249606
0.8986	High Similarity	NPC473887
0.8986	High Similarity	NPC1486
0.8986	High Similarity	NPC12165
0.8986	High Similarity	NPC98115
0.8986	High Similarity	NPC174999
0.8986	High Similarity	NPC29353
0.8986	High Similarity	NPC66349
0.8986	High Similarity	NPC234133
0.8986	High Similarity	NPC47815
0.8986	High Similarity	NPC168105
0.8986	High Similarity	NPC127447
0.8986	High Similarity	NPC186838
0.8986	High Similarity	NPC194281
0.8986	High Similarity	NPC41461
0.8986	High Similarity	NPC477242
0.8986	High Similarity	NPC477244
0.8986	High Similarity	NPC231772
0.8978	High Similarity	NPC125920
0.8978	High Similarity	NPC164136
0.8978	High Similarity	NPC144027
0.8978	High Similarity	NPC236974
0.8971	High Similarity	NPC182428
0.8971	High Similarity	NPC25937
0.8971	High Similarity	NPC10971
0.8971	High Similarity	NPC203817
0.8963	High Similarity	NPC5515
0.8963	High Similarity	NPC270369
0.8963	High Similarity	NPC250057
0.8958	High Similarity	NPC470460
0.8955	High Similarity	NPC230818
0.8951	High Similarity	NPC306488
0.8951	High Similarity	NPC5820
0.8951	High Similarity	NPC178343
0.8951	High Similarity	NPC329678
0.8944	High Similarity	NPC475705
0.8944	High Similarity	NPC470216
0.8944	High Similarity	NPC245482
0.8944	High Similarity	NPC51887
0.8944	High Similarity	NPC301751
0.8944	High Similarity	NPC117836
0.8944	High Similarity	NPC475201
0.8944	High Similarity	NPC476178
0.8936	High Similarity	NPC110969
0.8936	High Similarity	NPC3188
0.8929	High Similarity	NPC140890
0.8929	High Similarity	NPC222342
0.8929	High Similarity	NPC329203
0.8929	High Similarity	NPC265871
0.8929	High Similarity	NPC150648
0.8929	High Similarity	NPC230902
0.8929	High Similarity	NPC78913
0.8929	High Similarity	NPC274784
0.8929	High Similarity	NPC225153
0.8929	High Similarity	NPC18260
0.8929	High Similarity	NPC23257
0.8929	High Similarity	NPC310135
0.8929	High Similarity	NPC470211
0.8929	High Similarity	NPC139554
0.8929	High Similarity	NPC201541
0.8929	High Similarity	NPC20709
0.8929	High Similarity	NPC473076
0.8929	High Similarity	NPC261234
0.8921	High Similarity	NPC317119
0.8921	High Similarity	NPC290291
0.8921	High Similarity	NPC299379
0.8921	High Similarity	NPC188879
0.8921	High Similarity	NPC472419
0.8921	High Similarity	NPC275055
0.8921	High Similarity	NPC228661
0.8921	High Similarity	NPC153979
0.8913	High Similarity	NPC156092
0.8913	High Similarity	NPC131039
0.8913	High Similarity	NPC13575
0.8905	High Similarity	NPC108113
0.8905	High Similarity	NPC223354
0.8905	High Similarity	NPC93756
0.8897	High Similarity	NPC189106
0.8897	High Similarity	NPC186097
0.8897	High Similarity	NPC475009
0.8897	High Similarity	NPC112192
0.8897	High Similarity	NPC475008
0.8897	High Similarity	NPC164236
0.8897	High Similarity	NPC66384

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 NPC25427 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	1020
0.2-0.3	1741
0.3-0.4	2699
0.4-0.5	1878
0.5-0.6	1005
0.6-0.7	297
0.7-0.8	105
0.8-0.85	38
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9191	High Similarity	NPD1510	Phase 2
0.9037	High Similarity	NPD1240	Approved
0.8905	High Similarity	NPD1607	Approved
0.8881	High Similarity	NPD4378	Clinical (unspecified phase)
0.8857	High Similarity	NPD1549	Phase 2
0.8786	High Similarity	NPD1550	Clinical (unspecified phase)
0.8786	High Similarity	NPD1552	Clinical (unspecified phase)
0.8582	High Similarity	NPD2796	Approved
0.8552	High Similarity	NPD6799	Approved
0.8493	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD7075	Discontinued
0.8472	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD6801	Discontinued
0.8462	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD4380	Phase 2
0.8411	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD6651	Approved
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.8311	Intermediate Similarity	NPD1512	Approved
0.8301	Intermediate Similarity	NPD3882	Suspended
0.8278	Intermediate Similarity	NPD7411	Suspended
0.8224	Intermediate Similarity	NPD1934	Approved
0.8219	Intermediate Similarity	NPD3750	Approved
0.8176	Intermediate Similarity	NPD1511	Approved
0.817	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD2800	Approved
0.8133	Intermediate Similarity	NPD5403	Approved
0.8129	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD5401	Approved
0.8117	Intermediate Similarity	NPD3817	Phase 2
0.8117	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2801	Approved
0.8052	Intermediate Similarity	NPD7819	Suspended
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD1551	Phase 2
0.7937	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6166	Phase 2
0.7937	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1243	Approved
0.7905	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2532	Approved
0.7881	Intermediate Similarity	NPD2534	Approved
0.7881	Intermediate Similarity	NPD2533	Approved
0.7877	Intermediate Similarity	NPD3748	Approved
0.7877	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7768	Phase 2
0.7832	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2935	Discontinued
0.7805	Intermediate Similarity	NPD6797	Phase 2
0.7785	Intermediate Similarity	NPD2654	Approved
0.7785	Intermediate Similarity	NPD3749	Approved
0.7778	Intermediate Similarity	NPD920	Approved
0.7771	Intermediate Similarity	NPD5402	Approved
0.777	Intermediate Similarity	NPD2344	Approved
0.7758	Intermediate Similarity	NPD7251	Discontinued
0.775	Intermediate Similarity	NPD6959	Discontinued
0.7748	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD919	Approved
0.773	Intermediate Similarity	NPD3818	Discontinued
0.7724	Intermediate Similarity	NPD943	Approved
0.7711	Intermediate Similarity	NPD7808	Phase 3
0.7702	Intermediate Similarity	NPD6232	Discontinued
0.7676	Intermediate Similarity	NPD2798	Approved
0.7669	Intermediate Similarity	NPD7473	Discontinued
0.7664	Intermediate Similarity	NPD9545	Approved
0.7647	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD9493	Approved
0.7643	Intermediate Similarity	NPD9717	Approved
0.764	Intermediate Similarity	NPD1247	Approved
0.761	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1203	Approved
0.7605	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5953	Discontinued
0.7576	Intermediate Similarity	NPD7054	Approved
0.7571	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD422	Phase 1
0.7566	Intermediate Similarity	NPD2309	Approved
0.7551	Intermediate Similarity	NPD230	Phase 1
0.7536	Intermediate Similarity	NPD1548	Phase 1
0.753	Intermediate Similarity	NPD7472	Approved
0.753	Intermediate Similarity	NPD7074	Phase 3
0.7517	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7286	Phase 2
0.7469	Intermediate Similarity	NPD5494	Approved
0.7467	Intermediate Similarity	NPD6099	Approved
0.7467	Intermediate Similarity	NPD6100	Approved
0.7466	Intermediate Similarity	NPD2313	Discontinued
0.7448	Intermediate Similarity	NPD6832	Phase 2
0.7439	Intermediate Similarity	NPD3926	Phase 2
0.7426	Intermediate Similarity	NPD1241	Discontinued
0.74	Intermediate Similarity	NPD2799	Discontinued
0.74	Intermediate Similarity	NPD7033	Discontinued
0.7394	Intermediate Similarity	NPD3972	Approved
0.7386	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4628	Phase 3
0.7381	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7390	Discontinued
0.7347	Intermediate Similarity	NPD3268	Approved
0.7342	Intermediate Similarity	NPD3226	Approved
0.7337	Intermediate Similarity	NPD6559	Discontinued
0.7329	Intermediate Similarity	NPD4908	Phase 1
0.7325	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1610	Phase 2
0.7305	Intermediate Similarity	NPD3751	Discontinued
0.7289	Intermediate Similarity	NPD2403	Approved
0.7285	Intermediate Similarity	NPD4308	Phase 3
0.7273	Intermediate Similarity	NPD5710	Approved
0.7273	Intermediate Similarity	NPD5711	Approved
0.7257	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1470	Approved
0.7241	Intermediate Similarity	NPD2797	Approved
0.723	Intermediate Similarity	NPD6798	Discontinued
0.723	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1296	Phase 2
0.7222	Intermediate Similarity	NPD4288	Approved
0.72	Intermediate Similarity	NPD5124	Phase 1
0.72	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1019	Discontinued
0.719	Intermediate Similarity	NPD1471	Phase 3
0.7186	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3225	Approved
0.7172	Intermediate Similarity	NPD1876	Approved
0.716	Intermediate Similarity	NPD1465	Phase 2
0.716	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9494	Approved
0.7135	Intermediate Similarity	NPD6104	Discontinued
0.7125	Intermediate Similarity	NPD7458	Discontinued
0.7123	Intermediate Similarity	NPD3267	Approved
0.7123	Intermediate Similarity	NPD3266	Approved
0.7118	Intermediate Similarity	NPD1729	Discontinued
0.7115	Intermediate Similarity	NPD2354	Approved
0.7114	Intermediate Similarity	NPD411	Approved
0.7114	Intermediate Similarity	NPD3764	Approved
0.7113	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4749	Approved
0.7086	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1933	Approved
0.7086	Intermediate Similarity	NPD447	Suspended
0.7083	Intermediate Similarity	NPD1201	Approved
0.7079	Intermediate Similarity	NPD4360	Phase 2
0.7079	Intermediate Similarity	NPD4363	Phase 3
0.7078	Intermediate Similarity	NPD2346	Discontinued
0.7059	Intermediate Similarity	NPD9266	Approved
0.7059	Intermediate Similarity	NPD74	Approved
0.7039	Intermediate Similarity	NPD4361	Phase 2
0.7039	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4307	Phase 2
0.7012	Intermediate Similarity	NPD2296	Approved
0.7007	Intermediate Similarity	NPD1164	Approved
0.7006	Intermediate Similarity	NPD3887	Approved
0.7	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9267	Approved
0.6985	Remote Similarity	NPD9264	Approved
0.6985	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9263	Approved
0.6974	Remote Similarity	NPD6355	Discontinued
0.6968	Remote Similarity	NPD2353	Approved
0.6968	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6233	Phase 2
0.6943	Remote Similarity	NPD7003	Approved
0.6933	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3027	Phase 3
0.6932	Remote Similarity	NPD8434	Phase 2
0.6923	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD9269	Phase 2
0.6913	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3140	Approved
0.6908	Remote Similarity	NPD3142	Approved
0.6908	Remote Similarity	NPD1613	Approved
0.6903	Remote Similarity	NPD5404	Approved
0.6903	Remote Similarity	NPD5405	Approved
0.6903	Remote Similarity	NPD5406	Approved
0.6903	Remote Similarity	NPD5408	Approved
0.6899	Remote Similarity	NPD6190	Approved
0.6885	Remote Similarity	NPD6776	Approved
0.6885	Remote Similarity	NPD6778	Approved
0.6885	Remote Similarity	NPD6780	Approved
0.6885	Remote Similarity	NPD6777	Approved
0.6885	Remote Similarity	NPD6781	Approved
0.6885	Remote Similarity	NPD6779	Approved
0.6885	Remote Similarity	NPD6782	Approved
0.6879	Remote Similarity	NPD1652	Phase 2
0.6875	Remote Similarity	NPD9268	Approved
0.6875	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD940	Approved
0.6866	Remote Similarity	NPD846	Approved
0.6865	Remote Similarity	NPD7435	Discontinued
0.6864	Remote Similarity	NPD3787	Discontinued
0.6859	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4287	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