NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.04
Volume:	262.933
LogP:	1.029
LogD:	0.529
LogS:	-3.161
# Rotatable Bonds:	3
TPSA:	82.73
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.868
Synthetic Accessibility Score:	3.886
Fsp3:	0.154
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:	-4.65
MDCK Permeability:	1.4052396181796212e-05
Pgp-inhibitor:	0.073
Pgp-substrate:	0.756
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	79.4013900756836%
Volume Distribution (VD):	0.947
Pgp-substrate:	20.418949127197266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.569
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.743
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	5.369
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.917
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.75
Rat Oral Acute Toxicity:	0.386
Maximum Recommended Daily Dose:	0.417
Skin Sensitization:	0.428
Carcinogencity:	0.941
Eye Corrosion:	0.004
Eye Irritation:	0.319
Respiratory Toxicity:	0.731

Download Data

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

Natural Product: NPC472887

Natural Product ID:	NPC472887
*Common Name:**	FBGCOWPQAOHZEQ-AATRIKPKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FBGCOWPQAOHZEQ-AATRIKPKSA-N
Standard InCHI:	InChI=1S/C13H12O5S/c1-17-11-4-3-9-10(14)7-8(5-6-19(2)16)18-13(9)12(11)15/h3-7,15H,1-2H3/b6-5+
SMILES:	COC1=C(C2=C(C=C1)C(=O)C=C(O2)C=CS(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593562
PubChem CID:	n.a.
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
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579873]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26225905]
NPO23424	Dirca palustris	Species	Thymelaeaceae	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	3
Others	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[528349]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[528349]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[528349]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC90	=	14.0	ug.mL-1	PMID[528349]

☑ 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 NPC472887 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	414
0.1-0.2	2107
0.2-0.3	6156
0.3-0.4	11892
0.4-0.5	4727
0.5-0.6	4712
0.6-0.7	5502
0.7-0.8	5058
0.8-0.85	1438
0.85-0.9	647
0.9-0.95	42
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC472886
0.9524	High Similarity	NPC472885
0.9333	High Similarity	NPC472884
0.9133	High Similarity	NPC168803
0.9133	High Similarity	NPC61871
0.9133	High Similarity	NPC55557
0.9133	High Similarity	NPC30647
0.9085	High Similarity	NPC60972
0.9085	High Similarity	NPC39732
0.9079	High Similarity	NPC29231
0.9048	High Similarity	NPC50823
0.902	High Similarity	NPC31363
0.9013	High Similarity	NPC223579
0.9013	High Similarity	NPC137062
0.9013	High Similarity	NPC287101
0.9013	High Similarity	NPC183950
0.9013	High Similarity	NPC52005
0.8968	High Similarity	NPC256612
0.8968	High Similarity	NPC20830
0.8961	High Similarity	NPC239128
0.8961	High Similarity	NPC301323
0.8961	High Similarity	NPC162313
0.8961	High Similarity	NPC188203
0.8961	High Similarity	NPC71334
0.8961	High Similarity	NPC257648
0.8961	High Similarity	NPC187498
0.8961	High Similarity	NPC156222
0.8961	High Similarity	NPC83508
0.8961	High Similarity	NPC275836
0.8961	High Similarity	NPC100887
0.8961	High Similarity	NPC198826
0.8961	High Similarity	NPC241498
0.8961	High Similarity	NPC212678
0.8961	High Similarity	NPC57030
0.8961	High Similarity	NPC275722
0.8961	High Similarity	NPC55205
0.8961	High Similarity	NPC25270
0.8961	High Similarity	NPC477231
0.8961	High Similarity	NPC120163
0.8961	High Similarity	NPC293183
0.8961	High Similarity	NPC256283
0.8961	High Similarity	NPC222830
0.8961	High Similarity	NPC131624
0.8954	High Similarity	NPC45873
0.8947	High Similarity	NPC196277
0.8947	High Similarity	NPC272721
0.8947	High Similarity	NPC120464
0.8947	High Similarity	NPC43669
0.894	High Similarity	NPC143903
0.894	High Similarity	NPC226987
0.8933	High Similarity	NPC142165
0.891	High Similarity	NPC265511
0.891	High Similarity	NPC472455
0.8903	High Similarity	NPC231018
0.8903	High Similarity	NPC69394
0.8903	High Similarity	NPC183878
0.8903	High Similarity	NPC167091
0.8903	High Similarity	NPC206238
0.8903	High Similarity	NPC292214
0.8903	High Similarity	NPC22519
0.8903	High Similarity	NPC255350
0.8903	High Similarity	NPC274327
0.8903	High Similarity	NPC145379
0.8903	High Similarity	NPC176775
0.8903	High Similarity	NPC160951
0.8903	High Similarity	NPC47781
0.8903	High Similarity	NPC271779
0.8903	High Similarity	NPC88645
0.8896	High Similarity	NPC200740
0.8896	High Similarity	NPC125062
0.8896	High Similarity	NPC252933
0.8896	High Similarity	NPC54394
0.8889	High Similarity	NPC216318
0.8889	High Similarity	NPC40290
0.8889	High Similarity	NPC17286
0.8889	High Similarity	NPC259713
0.8889	High Similarity	NPC264289
0.8889	High Similarity	NPC69430
0.8889	High Similarity	NPC200060
0.8889	High Similarity	NPC264550
0.8889	High Similarity	NPC296197
0.8889	High Similarity	NPC177298
0.8889	High Similarity	NPC142876
0.8889	High Similarity	NPC139293
0.8889	High Similarity	NPC48479
0.8889	High Similarity	NPC333691
0.8889	High Similarity	NPC195763
0.8882	High Similarity	NPC125449
0.8882	High Similarity	NPC77378
0.8882	High Similarity	NPC12200
0.8882	High Similarity	NPC108406
0.8882	High Similarity	NPC188074
0.8874	High Similarity	NPC70136
0.8867	High Similarity	NPC254659
0.8867	High Similarity	NPC287722
0.8846	High Similarity	NPC227325
0.8846	High Similarity	NPC44079
0.8846	High Similarity	NPC168247
0.8846	High Similarity	NPC196439
0.8846	High Similarity	NPC57674
0.8846	High Similarity	NPC472280
0.8846	High Similarity	NPC4455
0.8846	High Similarity	NPC183597
0.8846	High Similarity	NPC213622
0.8846	High Similarity	NPC234255
0.8846	High Similarity	NPC167815
0.8846	High Similarity	NPC208197
0.8846	High Similarity	NPC138360
0.8846	High Similarity	NPC280339
0.8846	High Similarity	NPC152951
0.8846	High Similarity	NPC163780
0.8846	High Similarity	NPC117992
0.8846	High Similarity	NPC201136
0.8846	High Similarity	NPC2476
0.8846	High Similarity	NPC26227
0.8846	High Similarity	NPC230149
0.8846	High Similarity	NPC50715
0.8846	High Similarity	NPC128863
0.8846	High Similarity	NPC2928
0.8846	High Similarity	NPC201451
0.8846	High Similarity	NPC146165
0.8846	High Similarity	NPC92659
0.8844	High Similarity	NPC472883
0.8839	High Similarity	NPC39007
0.8839	High Similarity	NPC142540
0.8839	High Similarity	NPC304954
0.8839	High Similarity	NPC82325
0.8839	High Similarity	NPC180234
0.8839	High Similarity	NPC199100
0.8839	High Similarity	NPC120537
0.8839	High Similarity	NPC279989
0.8839	High Similarity	NPC161277
0.8839	High Similarity	NPC101996
0.8831	High Similarity	NPC184136
0.8831	High Similarity	NPC260582
0.8831	High Similarity	NPC306821
0.8824	High Similarity	NPC183655
0.8824	High Similarity	NPC195202
0.8824	High Similarity	NPC80710
0.8824	High Similarity	NPC203747
0.8824	High Similarity	NPC118726
0.8824	High Similarity	NPC139364
0.8824	High Similarity	NPC254702
0.8824	High Similarity	NPC12367
0.8824	High Similarity	NPC287395
0.8824	High Similarity	NPC194653
0.8816	High Similarity	NPC209278
0.8808	High Similarity	NPC279121
0.88	High Similarity	NPC301178
0.88	High Similarity	NPC299154
0.88	High Similarity	NPC284556
0.88	High Similarity	NPC312256
0.8797	High Similarity	NPC204879
0.879	High Similarity	NPC43243
0.879	High Similarity	NPC245546
0.879	High Similarity	NPC247017
0.879	High Similarity	NPC472916
0.879	High Similarity	NPC98661
0.879	High Similarity	NPC6633
0.879	High Similarity	NPC5322
0.879	High Similarity	NPC133970
0.879	High Similarity	NPC266960
0.879	High Similarity	NPC49824
0.879	High Similarity	NPC317383
0.8782	High Similarity	NPC70433
0.8782	High Similarity	NPC276409
0.8782	High Similarity	NPC78326
0.8782	High Similarity	NPC236223
0.8782	High Similarity	NPC49402
0.8782	High Similarity	NPC179126
0.8782	High Similarity	NPC273462
0.8782	High Similarity	NPC469550
0.8782	High Similarity	NPC270620
0.8782	High Similarity	NPC75279
0.8782	High Similarity	NPC33051
0.8782	High Similarity	NPC227337
0.8782	High Similarity	NPC250822
0.8774	High Similarity	NPC149614
0.8774	High Similarity	NPC260895
0.8774	High Similarity	NPC28274
0.8774	High Similarity	NPC308451
0.8774	High Similarity	NPC50403
0.8774	High Similarity	NPC171010
0.8774	High Similarity	NPC251110
0.8774	High Similarity	NPC225731
0.8774	High Similarity	NPC208043
0.8774	High Similarity	NPC133953
0.8774	High Similarity	NPC226973
0.8766	High Similarity	NPC270465
0.8766	High Similarity	NPC92722
0.8766	High Similarity	NPC102003
0.8766	High Similarity	NPC87125
0.8766	High Similarity	NPC159103
0.8758	High Similarity	NPC239312
0.8758	High Similarity	NPC51443
0.8758	High Similarity	NPC74881
0.8758	High Similarity	NPC33265
0.8758	High Similarity	NPC62536
0.8758	High Similarity	NPC130230
0.8758	High Similarity	NPC95864

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 NPC472887 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	1009
0.2-0.3	1987
0.3-0.4	2790
0.4-0.5	1618
0.5-0.6	979
0.6-0.7	267
0.7-0.8	98
0.8-0.85	13
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8903	High Similarity	NPD2801	Approved
0.8808	High Similarity	NPD1511	Approved
0.879	High Similarity	NPD3882	Suspended
0.8718	High Similarity	NPD1934	Approved
0.8693	High Similarity	NPD1512	Approved
0.8428	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8261	Intermediate Similarity	NPD3817	Phase 2
0.8193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6166	Phase 2
0.8158	Intermediate Similarity	NPD1510	Phase 2
0.8155	Intermediate Similarity	NPD7054	Approved
0.8133	Intermediate Similarity	NPD943	Approved
0.8133	Intermediate Similarity	NPD1240	Approved
0.8117	Intermediate Similarity	NPD1549	Phase 2
0.8117	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7472	Approved
0.8052	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD7074	Phase 3
0.7988	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6799	Approved
0.7965	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD230	Phase 1
0.7961	Intermediate Similarity	NPD447	Suspended
0.7953	Intermediate Similarity	NPD6797	Phase 2
0.7953	Intermediate Similarity	NPD5953	Discontinued
0.7907	Intermediate Similarity	NPD7251	Discontinued
0.7904	Intermediate Similarity	NPD1247	Approved
0.7901	Intermediate Similarity	NPD4380	Phase 2
0.7892	Intermediate Similarity	NPD919	Approved
0.7871	Intermediate Similarity	NPD2796	Approved
0.7866	Intermediate Similarity	NPD1465	Phase 2
0.7861	Intermediate Similarity	NPD7808	Phase 3
0.7844	Intermediate Similarity	NPD5494	Approved
0.7831	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7075	Discontinued
0.7812	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD9494	Approved
0.7758	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6232	Discontinued
0.7719	Intermediate Similarity	NPD7473	Discontinued
0.7706	Intermediate Similarity	NPD3926	Phase 2
0.7697	Intermediate Similarity	NPD6801	Discontinued
0.7683	Intermediate Similarity	NPD6599	Discontinued
0.7673	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7819	Suspended
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.763	Intermediate Similarity	NPD7286	Phase 2
0.761	Intermediate Similarity	NPD2800	Approved
0.7605	Intermediate Similarity	NPD5402	Approved
0.7562	Intermediate Similarity	NPD3750	Approved
0.7543	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7411	Suspended
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD5401	Approved
0.7451	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1613	Approved
0.7436	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5844	Phase 1
0.7412	Intermediate Similarity	NPD3749	Approved
0.7403	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1652	Phase 2
0.7378	Intermediate Similarity	NPD2534	Approved
0.7378	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2532	Approved
0.7378	Intermediate Similarity	NPD2533	Approved
0.7375	Intermediate Similarity	NPD2344	Approved
0.7362	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD9717	Approved
0.7351	Intermediate Similarity	NPD9269	Phase 2
0.7349	Intermediate Similarity	NPD1653	Approved
0.732	Intermediate Similarity	NPD1203	Approved
0.7312	Intermediate Similarity	NPD2935	Discontinued
0.7308	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6559	Discontinued
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7283	Intermediate Similarity	NPD6959	Discontinued
0.7278	Intermediate Similarity	NPD1933	Approved
0.7257	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7768	Phase 2
0.725	Intermediate Similarity	NPD3748	Approved
0.725	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3027	Phase 3
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7239	Intermediate Similarity	NPD4628	Phase 3
0.7233	Intermediate Similarity	NPD6651	Approved
0.7197	Intermediate Similarity	NPD411	Approved
0.7195	Intermediate Similarity	NPD2309	Approved
0.7178	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3540	Phase 1
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.711	Intermediate Similarity	NPD6971	Discontinued
0.7108	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3226	Approved
0.7099	Intermediate Similarity	NPD6100	Approved
0.7099	Intermediate Similarity	NPD3539	Phase 1
0.7099	Intermediate Similarity	NPD6099	Approved
0.7089	Intermediate Similarity	NPD2313	Discontinued
0.7086	Intermediate Similarity	NPD9268	Approved
0.7086	Intermediate Similarity	NPD7199	Phase 2
0.7079	Intermediate Similarity	NPD3751	Discontinued
0.703	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1548	Phase 1
0.702	Intermediate Similarity	NPD9545	Approved
0.7007	Intermediate Similarity	NPD228	Approved
0.7006	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9493	Approved
0.6994	Remote Similarity	NPD5353	Approved
0.6988	Remote Similarity	NPD6190	Approved
0.6981	Remote Similarity	NPD1296	Phase 2
0.6978	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6234	Discontinued
0.697	Remote Similarity	NPD2654	Approved
0.6962	Remote Similarity	NPD6832	Phase 2
0.6957	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2346	Discontinued
0.6948	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5049	Phase 3
0.6923	Remote Similarity	NPD7685	Pre-registration
0.6913	Remote Similarity	NPD1241	Discontinued
0.691	Remote Similarity	NPD5242	Approved
0.6905	Remote Similarity	NPD4357	Discontinued
0.6903	Remote Similarity	NPD1608	Approved
0.6872	Remote Similarity	NPD2403	Approved
0.6865	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5711	Approved
0.6854	Remote Similarity	NPD5710	Approved
0.6854	Remote Similarity	NPD3787	Discontinued
0.6852	Remote Similarity	NPD4340	Discontinued
0.6842	Remote Similarity	NPD5536	Phase 2
0.6839	Remote Similarity	NPD1610	Phase 2
0.6835	Remote Similarity	NPD2798	Approved
0.6835	Remote Similarity	NPD1019	Discontinued
0.6832	Remote Similarity	NPD4062	Phase 3
0.6829	Remote Similarity	NPD4308	Phase 3
0.6821	Remote Similarity	NPD6386	Approved
0.6821	Remote Similarity	NPD6385	Approved
0.6802	Remote Similarity	NPD824	Approved
0.6792	Remote Similarity	NPD3018	Phase 2
0.6782	Remote Similarity	NPD37	Approved
0.6776	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1470	Approved
0.677	Remote Similarity	NPD3268	Approved
0.6761	Remote Similarity	NPD4966	Approved
0.6761	Remote Similarity	NPD4965	Approved
0.6761	Remote Similarity	NPD4967	Phase 2
0.675	Remote Similarity	NPD4908	Phase 1
0.6747	Remote Similarity	NPD1471	Phase 3
0.6746	Remote Similarity	NPD7440	Discontinued
0.6727	Remote Similarity	NPD7033	Discontinued
0.6721	Remote Similarity	NPD1729	Discontinued
0.671	Remote Similarity	NPD17	Approved
0.6709	Remote Similarity	NPD3225	Approved
0.6706	Remote Similarity	NPD7390	Discontinued
0.6705	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4288	Approved
0.6705	Remote Similarity	NPD2296	Approved
0.6703	Remote Similarity	NPD7228	Approved
0.6703	Remote Similarity	NPD2163	Approved
0.6687	Remote Similarity	NPD1558	Phase 1
0.6686	Remote Similarity	NPD2354	Approved
0.6686	Remote Similarity	NPD6844	Discontinued
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8312	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD8313	Approved
0.6649	Remote Similarity	NPD6104	Discontinued
0.6649	Remote Similarity	NPD8434	Phase 2
0.6646	Remote Similarity	NPD2983	Phase 2
0.6646	Remote Similarity	NPD4749	Approved
0.6646	Remote Similarity	NPD2982	Phase 2
0.6627	Remote Similarity	NPD3892	Phase 2
0.6624	Remote Similarity	NPD1201	Approved
0.6615	Remote Similarity	NPD4360	Phase 2
0.6615	Remote Similarity	NPD4363	Phase 3
0.6614	Remote Similarity	NPD6842	Approved
0.6614	Remote Similarity	NPD6841	Approved
0.6614	Remote Similarity	NPD6843	Phase 3
0.6609	Remote Similarity	NPD3111	Phase 1
0.6609	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2424	Discontinued
0.6603	Remote Similarity	NPD1778	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