NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	356.09
Volume:	343.394
LogP:	3.102
LogD:	2.953
LogS:	-4.61
# Rotatable Bonds:	4
TPSA:	76.36
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.71
Synthetic Accessibility Score:	2.56
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.61
MDCK Permeability:	4.537029963103123e-05
Pgp-inhibitor:	0.878
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	84.88607025146484%
Volume Distribution (VD):	0.555
Pgp-substrate:	13.603873252868652%

ADMET: Metabolism

CYP1A2-inhibitor:	0.821
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.393
CYP2C9-inhibitor:	0.806
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.888
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	5.651
Half-life (T1/2):	0.221

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.728
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.381
Skin Sensitization:	0.688
Carcinogencity:	0.632
Eye Corrosion:	0.004
Eye Irritation:	0.222
Respiratory Toxicity:	0.35

Download Data

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

Natural Product: NPC478213

Natural Product ID:	NPC478213
*Common Name:**	7,2',5'-trimethoxy-3',4'-methylenedioxy isoflavone
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DWSIYHMUFRFFCM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O7/c1-21-10-4-5-11-14(6-10)24-8-13(16(11)20)12-7-15(22-2)18-19(17(12)23-3)26-9-25-18/h4-8H,9H2,1-3H3
SMILES:	COC1=CC=C2C(=O)C(C3=CC(OC)=C4OCOC4=C3OC)=COC2=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002602] 7-O-methylated isoflavonoids [CHEMONTID:0002689] 7-O-methylisoflavones

*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
NPO33696	Millettia oblata ssp. teitensis	Species	Fabaceae	Eukaryota	leaves	Ngangao Forest, Taita Hill, Taita County, Kenya	2014-JUL	PMID[28665590]

☑ 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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC478213 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	504
0.1-0.2	1983
0.2-0.3	4840
0.3-0.4	11047
0.4-0.5	6835
0.5-0.6	3865
0.6-0.7	5772
0.7-0.8	5101
0.8-0.85	1867
0.85-0.9	770
0.9-0.95	97
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC148497
0.9932	High Similarity	NPC153008
0.9864	High Similarity	NPC57211
0.9863	High Similarity	NPC279061
0.9797	High Similarity	NPC478238
0.9796	High Similarity	NPC52623
0.9603	High Similarity	NPC215375
0.9603	High Similarity	NPC62518
0.9536	High Similarity	NPC167595
0.9536	High Similarity	NPC258644
0.953	High Similarity	NPC292460
0.953	High Similarity	NPC68882
0.9521	High Similarity	NPC216314
0.9521	High Similarity	NPC120924
0.9521	High Similarity	NPC195919
0.9477	High Similarity	NPC295009
0.9477	High Similarity	NPC260640
0.9467	High Similarity	NPC244371
0.9452	High Similarity	NPC224687
0.9452	High Similarity	NPC296575
0.9416	High Similarity	NPC18284
0.9416	High Similarity	NPC273021
0.9412	High Similarity	NPC225624
0.9412	High Similarity	NPC285973
0.9384	High Similarity	NPC182842
0.9346	High Similarity	NPC257914
0.9346	High Similarity	NPC238405
0.9346	High Similarity	NPC104459
0.929	High Similarity	NPC478199
0.9281	High Similarity	NPC310206
0.9276	High Similarity	NPC284353
0.9272	High Similarity	NPC104728
0.9272	High Similarity	NPC35544
0.9247	High Similarity	NPC185607
0.9226	High Similarity	NPC34376
0.9221	High Similarity	NPC113055
0.9216	High Similarity	NPC155063
0.9211	High Similarity	NPC186507
0.9211	High Similarity	NPC279930
0.9205	High Similarity	NPC262623
0.9195	High Similarity	NPC205522
0.9178	High Similarity	NPC58229
0.9161	High Similarity	NPC131557
0.9156	High Similarity	NPC19097
0.9139	High Similarity	NPC234152
0.9139	High Similarity	NPC239363
0.9139	High Similarity	NPC156953
0.9133	High Similarity	NPC10304
0.9133	High Similarity	NPC63256
0.9128	High Similarity	NPC40818
0.9128	High Similarity	NPC110639
0.9128	High Similarity	NPC106461
0.9128	High Similarity	NPC215932
0.9128	High Similarity	NPC14958
0.9114	High Similarity	NPC113093
0.9091	High Similarity	NPC301897
0.9085	High Similarity	NPC124714
0.9073	High Similarity	NPC238366
0.9067	High Similarity	NPC85233
0.906	High Similarity	NPC471590
0.906	High Similarity	NPC136278
0.9057	High Similarity	NPC135345
0.9054	High Similarity	NPC476054
0.9045	High Similarity	NPC469575
0.9045	High Similarity	NPC302741
0.9032	High Similarity	NPC474990
0.902	High Similarity	NPC100971
0.902	High Similarity	NPC291802
0.902	High Similarity	NPC209487
0.902	High Similarity	NPC269451
0.902	High Similarity	NPC181209
0.902	High Similarity	NPC35763
0.902	High Similarity	NPC121522
0.902	High Similarity	NPC131266
0.902	High Similarity	NPC245382
0.902	High Similarity	NPC216769
0.902	High Similarity	NPC100263
0.9006	High Similarity	NPC223375
0.9006	High Similarity	NPC475825
0.9	High Similarity	NPC283002
0.9	High Similarity	NPC302408
0.9	High Similarity	NPC231013
0.8993	High Similarity	NPC113089
0.8993	High Similarity	NPC23955
0.8987	High Similarity	NPC470178
0.8981	High Similarity	NPC162668
0.8981	High Similarity	NPC94155
0.8973	High Similarity	NPC44573
0.8961	High Similarity	NPC280937
0.8961	High Similarity	NPC250557
0.8961	High Similarity	NPC128961
0.8961	High Similarity	NPC472408
0.8954	High Similarity	NPC220577
0.8954	High Similarity	NPC288316
0.8954	High Similarity	NPC19980
0.8954	High Similarity	NPC45291
0.8951	High Similarity	NPC72455
0.8947	High Similarity	NPC69752
0.8944	High Similarity	NPC105511
0.894	High Similarity	NPC119660
0.894	High Similarity	NPC474999
0.894	High Similarity	NPC93034
0.8938	High Similarity	NPC76482
0.8933	High Similarity	NPC165512
0.8931	High Similarity	NPC187923
0.8926	High Similarity	NPC70853
0.8926	High Similarity	NPC9966
0.8924	High Similarity	NPC125991
0.8917	High Similarity	NPC269906
0.8917	High Similarity	NPC298093
0.8903	High Similarity	NPC130589
0.8903	High Similarity	NPC39184
0.8903	High Similarity	NPC134287
0.8896	High Similarity	NPC166201
0.8889	High Similarity	NPC475155
0.8889	High Similarity	NPC307518
0.8889	High Similarity	NPC205076
0.8889	High Similarity	NPC48773
0.8889	High Similarity	NPC259058
0.8889	High Similarity	NPC201547
0.8889	High Similarity	NPC10467
0.8882	High Similarity	NPC41853
0.8882	High Similarity	NPC471287
0.8882	High Similarity	NPC476058
0.8874	High Similarity	NPC153620
0.8874	High Similarity	NPC24257
0.8874	High Similarity	NPC88345
0.8874	High Similarity	NPC12377
0.8868	High Similarity	NPC65846
0.8867	High Similarity	NPC293201
0.8859	High Similarity	NPC29536
0.8859	High Similarity	NPC214919
0.8859	High Similarity	NPC124467
0.8846	High Similarity	NPC180340
0.8841	High Similarity	NPC156635
0.8839	High Similarity	NPC471981
0.8839	High Similarity	NPC472915
0.8831	High Similarity	NPC308451
0.8831	High Similarity	NPC226973
0.8831	High Similarity	NPC474663
0.8831	High Similarity	NPC208043
0.8831	High Similarity	NPC198615
0.8827	High Similarity	NPC44558
0.8827	High Similarity	NPC212748
0.8827	High Similarity	NPC224462
0.8824	High Similarity	NPC40290
0.8824	High Similarity	NPC92722
0.8824	High Similarity	NPC69430
0.8824	High Similarity	NPC200060
0.8824	High Similarity	NPC195763
0.8824	High Similarity	NPC181250
0.8824	High Similarity	NPC264550
0.8824	High Similarity	NPC264289
0.8824	High Similarity	NPC333691
0.8824	High Similarity	NPC102003
0.8824	High Similarity	NPC139293
0.8824	High Similarity	NPC142876
0.882	High Similarity	NPC42892
0.882	High Similarity	NPC167479
0.8816	High Similarity	NPC117463
0.8816	High Similarity	NPC470511
0.8816	High Similarity	NPC299923
0.8805	High Similarity	NPC81679
0.879	High Similarity	NPC476981
0.879	High Similarity	NPC78103
0.879	High Similarity	NPC181960
0.8788	High Similarity	NPC67302
0.8782	High Similarity	NPC34725
0.8782	High Similarity	NPC20830
0.8782	High Similarity	NPC472909
0.8782	High Similarity	NPC18954
0.8782	High Similarity	NPC37392
0.8782	High Similarity	NPC276059
0.8782	High Similarity	NPC213622
0.8782	High Similarity	NPC241774
0.8782	High Similarity	NPC122623
0.8782	High Similarity	NPC256612
0.878	High Similarity	NPC66804
0.878	High Similarity	NPC472607
0.8774	High Similarity	NPC134677
0.8774	High Similarity	NPC40033
0.8774	High Similarity	NPC38469
0.8773	High Similarity	NPC235575
0.8773	High Similarity	NPC475964
0.8767	High Similarity	NPC143649
0.8766	High Similarity	NPC306821
0.8766	High Similarity	NPC5840
0.8766	High Similarity	NPC189270
0.8766	High Similarity	NPC29056
0.8765	High Similarity	NPC472383
0.8765	High Similarity	NPC105025
0.8765	High Similarity	NPC475942
0.8765	High Similarity	NPC472381
0.8765	High Similarity	NPC201292
0.8765	High Similarity	NPC45638
0.8765	High Similarity	NPC226294
0.8765	High Similarity	NPC58053
0.8765	High Similarity	NPC469931
0.8765	High Similarity	NPC211309
0.8765	High Similarity	NPC93337

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 NPC478213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	434
0.1-0.2	997
0.2-0.3	1863
0.3-0.4	2747
0.4-0.5	1777
0.5-0.6	860
0.6-0.7	323
0.7-0.8	112
0.8-0.85	29
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.894	High Similarity	NPD6980	Clinical (unspecified phase)
0.8938	High Similarity	NPD3818	Discontinued
0.8917	High Similarity	NPD5494	Approved
0.8718	High Similarity	NPD2801	Approved
0.8544	High Similarity	NPD3817	Phase 2
0.8509	High Similarity	NPD1247	Approved
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8443	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7054	Approved
0.8418	Intermediate Similarity	NPD1934	Approved
0.84	Intermediate Similarity	NPD2796	Approved
0.8373	Intermediate Similarity	NPD7472	Approved
0.8373	Intermediate Similarity	NPD7074	Phase 3
0.8323	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD919	Approved
0.825	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7808	Phase 3
0.8214	Intermediate Similarity	NPD6797	Phase 2
0.8212	Intermediate Similarity	NPD1510	Phase 2
0.8182	Intermediate Similarity	NPD3926	Phase 2
0.8166	Intermediate Similarity	NPD7251	Discontinued
0.8141	Intermediate Similarity	NPD1511	Approved
0.8121	Intermediate Similarity	NPD6232	Discontinued
0.8084	Intermediate Similarity	NPD7473	Discontinued
0.8063	Intermediate Similarity	NPD4380	Phase 2
0.8038	Intermediate Similarity	NPD1512	Approved
0.8025	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6799	Approved
0.8024	Intermediate Similarity	NPD6166	Phase 2
0.8024	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD920	Approved
0.7975	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5402	Approved
0.7963	Intermediate Similarity	NPD37	Approved
0.7953	Intermediate Similarity	NPD6559	Discontinued
0.7947	Intermediate Similarity	NPD1240	Approved
0.7927	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7819	Suspended
0.7895	Intermediate Similarity	NPD1933	Approved
0.7882	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD5844	Phase 1
0.7862	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6801	Discontinued
0.7844	Intermediate Similarity	NPD7199	Phase 2
0.7843	Intermediate Similarity	NPD1607	Approved
0.784	Intermediate Similarity	NPD6599	Discontinued
0.7834	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1549	Phase 2
0.7818	Intermediate Similarity	NPD4966	Approved
0.7818	Intermediate Similarity	NPD4965	Approved
0.7818	Intermediate Similarity	NPD4967	Phase 2
0.7806	Intermediate Similarity	NPD2935	Discontinued
0.7771	Intermediate Similarity	NPD1243	Approved
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7756	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6234	Discontinued
0.7712	Intermediate Similarity	NPD943	Approved
0.7683	Intermediate Similarity	NPD7411	Suspended
0.7667	Intermediate Similarity	NPD2798	Approved
0.7647	Intermediate Similarity	NPD5242	Approved
0.764	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2533	Approved
0.764	Intermediate Similarity	NPD2532	Approved
0.764	Intermediate Similarity	NPD2534	Approved
0.764	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3748	Approved
0.7595	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5403	Approved
0.7531	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD1653	Approved
0.7486	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7473	Intermediate Similarity	NPD5006	Approved
0.7473	Intermediate Similarity	NPD5005	Approved
0.747	Intermediate Similarity	NPD6386	Approved
0.747	Intermediate Similarity	NPD6385	Approved
0.7456	Intermediate Similarity	NPD3749	Approved
0.7443	Intermediate Similarity	NPD7685	Pre-registration
0.744	Intermediate Similarity	NPD5353	Approved
0.744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2654	Approved
0.7436	Intermediate Similarity	NPD230	Phase 1
0.7436	Intermediate Similarity	NPD447	Suspended
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7414	Intermediate Similarity	NPD7228	Approved
0.7391	Intermediate Similarity	NPD3750	Approved
0.7384	Intermediate Similarity	NPD3787	Discontinued
0.7355	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4420	Approved
0.7349	Intermediate Similarity	NPD7458	Discontinued
0.7347	Intermediate Similarity	NPD5536	Phase 2
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD3705	Approved
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2800	Approved
0.7326	Intermediate Similarity	NPD6959	Discontinued
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7768	Phase 2
0.729	Intermediate Similarity	NPD3027	Phase 3
0.7273	Intermediate Similarity	NPD6778	Approved
0.7273	Intermediate Similarity	NPD6779	Approved
0.7273	Intermediate Similarity	NPD6776	Approved
0.7273	Intermediate Similarity	NPD6780	Approved
0.7273	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD6781	Approved
0.7273	Intermediate Similarity	NPD6777	Approved
0.725	Intermediate Similarity	NPD1551	Phase 2
0.7247	Intermediate Similarity	NPD7240	Approved
0.7244	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2344	Approved
0.72	Intermediate Similarity	NPD2403	Approved
0.7188	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2799	Discontinued
0.7178	Intermediate Similarity	NPD4628	Phase 3
0.7171	Intermediate Similarity	NPD3972	Approved
0.7161	Intermediate Similarity	NPD3018	Phase 2
0.7161	Intermediate Similarity	NPD9494	Approved
0.7158	Intermediate Similarity	NPD7696	Phase 3
0.7158	Intermediate Similarity	NPD7697	Approved
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7158	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD3226	Approved
0.7134	Intermediate Similarity	NPD6190	Approved
0.712	Intermediate Similarity	NPD7870	Phase 2
0.712	Intermediate Similarity	NPD7871	Phase 2
0.7111	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7028	Phase 2
0.7099	Intermediate Similarity	NPD2346	Discontinued
0.7095	Intermediate Similarity	NPD5953	Discontinued
0.7093	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5710	Approved
0.7086	Intermediate Similarity	NPD5711	Approved
0.7079	Intermediate Similarity	NPD7286	Phase 2
0.7072	Intermediate Similarity	NPD8312	Approved
0.7072	Intermediate Similarity	NPD8313	Approved
0.7063	Intermediate Similarity	NPD6651	Approved
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7049	Intermediate Similarity	NPD8434	Phase 2
0.7048	Intermediate Similarity	NPD4357	Discontinued
0.7044	Intermediate Similarity	NPD1613	Approved
0.7044	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5978	Approved
0.7035	Intermediate Similarity	NPD5977	Approved
0.703	Intermediate Similarity	NPD2309	Approved
0.7018	Intermediate Similarity	NPD6844	Discontinued
0.7016	Intermediate Similarity	NPD6823	Phase 2
0.7013	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2983	Phase 2
0.7013	Intermediate Similarity	NPD2982	Phase 2
0.701	Intermediate Similarity	NPD7701	Phase 2
0.7006	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6535	Approved
0.7005	Intermediate Similarity	NPD6534	Approved
0.6994	Remote Similarity	NPD1471	Phase 3
0.6989	Remote Similarity	NPD7229	Phase 3
0.6975	Remote Similarity	NPD7033	Discontinued
0.6968	Remote Similarity	NPD1876	Approved
0.6959	Remote Similarity	NPD5283	Phase 1
0.6959	Remote Similarity	NPD7584	Approved
0.6946	Remote Similarity	NPD7390	Discontinued
0.6943	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7874	Approved
0.6939	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4307	Phase 2
0.6927	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3266	Approved
0.6923	Remote Similarity	NPD3267	Approved
0.6919	Remote Similarity	NPD6279	Approved
0.6919	Remote Similarity	NPD6280	Approved
0.6908	Remote Similarity	NPD9268	Approved
0.6904	Remote Similarity	NPD7801	Approved
0.6895	Remote Similarity	NPD7699	Phase 2
0.6895	Remote Similarity	NPD7700	Phase 2
0.6893	Remote Similarity	NPD6808	Phase 2
0.689	Remote Similarity	NPD7266	Discontinued
0.6879	Remote Similarity	NPD1019	Discontinued
0.6864	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD17	Approved
0.6839	Remote Similarity	NPD9269	Phase 2
0.6831	Remote Similarity	NPD7549	Discontinued
0.6829	Remote Similarity	NPD6100	Approved
0.6829	Remote Similarity	NPD6099	Approved
0.6826	Remote Similarity	NPD3887	Approved
0.6818	Remote Similarity	NPD7783	Phase 2
0.6818	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1203	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