NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	255.09
Volume:	261.239
LogP:	3.646
LogD:	3.702
LogS:	-5.11
# Rotatable Bonds:	3
TPSA:	51.32
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.716
Synthetic Accessibility Score:	1.861
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.907
MDCK Permeability:	2.0339266484370455e-05
Pgp-inhibitor:	0.587
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.546

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.679
Plasma Protein Binding (PPB):	94.04602813720703%
Volume Distribution (VD):	0.666
Pgp-substrate:	5.268960952758789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.715
CYP2C19-substrate:	0.201
CYP2C9-inhibitor:	0.414
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.734
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.728
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	7.498
Half-life (T1/2):	0.554

ADMET: Toxicity

hERG Blockers:	0.125
Human Hepatotoxicity (H-HT):	0.519
Drug-inuced Liver Injury (DILI):	0.901
AMES Toxicity:	0.603
Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.709
Carcinogencity:	0.512
Eye Corrosion:	0.005
Eye Irritation:	0.909
Respiratory Toxicity:	0.769

Download Data

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

Natural Product: NPC46869

Natural Product ID:	NPC46869
*Common Name:**	O-Methylalloptaeroxylin
IUPAC Name:	5-methoxy-2,8,8-trimethylpyrano[2,3-h]chromen-4-one
Synonyms:	O-Methylalloptaeroxylin
Standard InCHIKey:	KADZFFQFRJPWDH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-9-7-11(17)14-13(18-4)8-12-10(15(14)19-9)5-6-16(2,3)20-12/h5-8H,1-4H3
SMILES:	Cc1cc(=O)c2c(cc3c(C=CC(C)(C)O3)c2o1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2164965
PubChem CID:	441968
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003543] Pyranochromenes

*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
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757709]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[16394547]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17685627]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23078294]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23513740]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23688954]
NPO9601	Ptaeroxylon obliquum	Species	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[32790311]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13538	Harrisonia abyssinica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9601	Ptaeroxylon obliquum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13538	Harrisonia abyssinica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9601	Ptaeroxylon obliquum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21362	Harrisonia perforata	Species	Rutaceae	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
EC50	1
IC50	1
Others	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	37.26	ug.mL-1	PMID[463765]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	8.3	n.a.	PMID[463765]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	4.49	ug.mL-1	PMID[463765]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	9.2	%	PMID[463765]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	66410.0	nM	PMID[463766]

☑ 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 NPC46869 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	465
0.1-0.2	1904
0.2-0.3	5309
0.3-0.4	12635
0.4-0.5	4825
0.5-0.6	5121
0.6-0.7	5856
0.7-0.8	4212
0.8-0.85	1464
0.85-0.9	793
0.9-0.95	110
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC17848
0.9771	High Similarity	NPC161196
0.9615	High Similarity	NPC229646
0.9549	High Similarity	NPC157855
0.9481	High Similarity	NPC150522
0.9466	High Similarity	NPC473655
0.9466	High Similarity	NPC101294
0.9416	High Similarity	NPC59522
0.9412	High Similarity	NPC52576
0.9412	High Similarity	NPC103362
0.9407	High Similarity	NPC23257
0.9407	High Similarity	NPC11566
0.9403	High Similarity	NPC259685
0.9403	High Similarity	NPC253616
0.9403	High Similarity	NPC38153
0.9389	High Similarity	NPC278556
0.938	High Similarity	NPC473907
0.9348	High Similarity	NPC179970
0.9343	High Similarity	NPC78803
0.9343	High Similarity	NPC226636
0.9343	High Similarity	NPC214236
0.9343	High Similarity	NPC217083
0.9343	High Similarity	NPC293852
0.9343	High Similarity	NPC299080
0.9343	High Similarity	NPC62840
0.9343	High Similarity	NPC11561
0.9343	High Similarity	NPC59739
0.9338	High Similarity	NPC159275
0.9338	High Similarity	NPC241100
0.9338	High Similarity	NPC472409
0.9338	High Similarity	NPC471587
0.9333	High Similarity	NPC470669
0.9333	High Similarity	NPC131130
0.9333	High Similarity	NPC470668
0.9328	High Similarity	NPC268081
0.9328	High Similarity	NPC254741
0.9328	High Similarity	NPC174999
0.9308	High Similarity	NPC473894
0.9302	High Similarity	NPC475496
0.9302	High Similarity	NPC49852
0.927	High Similarity	NPC205006
0.927	High Similarity	NPC110969
0.927	High Similarity	NPC282300
0.927	High Similarity	NPC147688
0.927	High Similarity	NPC156590
0.927	High Similarity	NPC64908
0.927	High Similarity	NPC118840
0.9265	High Similarity	NPC55018
0.9265	High Similarity	NPC220062
0.9265	High Similarity	NPC18260
0.9265	High Similarity	NPC303633
0.9265	High Similarity	NPC53181
0.9265	High Similarity	NPC473076
0.9265	High Similarity	NPC217186
0.9265	High Similarity	NPC96565
0.9265	High Similarity	NPC216978
0.9265	High Similarity	NPC301217
0.9265	High Similarity	NPC78913
0.9254	High Similarity	NPC101752
0.9254	High Similarity	NPC99854
0.9248	High Similarity	NPC292998
0.9242	High Similarity	NPC284424
0.9214	High Similarity	NPC104406
0.9214	High Similarity	NPC97716
0.9214	High Similarity	NPC79469
0.9214	High Similarity	NPC237635
0.9214	High Similarity	NPC24673
0.9214	High Similarity	NPC201731
0.9209	High Similarity	NPC234629
0.9209	High Similarity	NPC319752
0.9209	High Similarity	NPC311741
0.9203	High Similarity	NPC147145
0.9197	High Similarity	NPC172986
0.9197	High Similarity	NPC261227
0.9197	High Similarity	NPC475680
0.9197	High Similarity	NPC270883
0.9197	High Similarity	NPC235239
0.9197	High Similarity	NPC305355
0.9191	High Similarity	NPC201395
0.9191	High Similarity	NPC36414
0.9185	High Similarity	NPC72452
0.9185	High Similarity	NPC61546
0.9179	High Similarity	NPC125269
0.9179	High Similarity	NPC125920
0.9149	High Similarity	NPC244407
0.9149	High Similarity	NPC266572
0.9149	High Similarity	NPC189087
0.9149	High Similarity	NPC321623
0.9149	High Similarity	NPC6511
0.9149	High Similarity	NPC161191
0.9143	High Similarity	NPC246948
0.9143	High Similarity	NPC301276
0.9143	High Similarity	NPC111786
0.9143	High Similarity	NPC214774
0.9143	High Similarity	NPC475052
0.9143	High Similarity	NPC312973
0.9143	High Similarity	NPC54577
0.9143	High Similarity	NPC476088
0.9143	High Similarity	NPC83357
0.9143	High Similarity	NPC267375
0.9143	High Similarity	NPC142405
0.9143	High Similarity	NPC67805
0.9143	High Similarity	NPC176229
0.9143	High Similarity	NPC474161
0.9143	High Similarity	NPC195621
0.9143	High Similarity	NPC470647
0.9143	High Similarity	NPC20488
0.9143	High Similarity	NPC88964
0.9143	High Similarity	NPC124729
0.9143	High Similarity	NPC329678
0.9137	High Similarity	NPC17262
0.9137	High Similarity	NPC219915
0.9137	High Similarity	NPC316816
0.9137	High Similarity	NPC214166
0.9137	High Similarity	NPC255133
0.9137	High Similarity	NPC166138
0.9137	High Similarity	NPC106985
0.9137	High Similarity	NPC242100
0.9137	High Similarity	NPC38219
0.9137	High Similarity	NPC18585
0.9137	High Similarity	NPC478086
0.913	High Similarity	NPC201820
0.913	High Similarity	NPC22467
0.9124	High Similarity	NPC472515
0.9124	High Similarity	NPC139554
0.9124	High Similarity	NPC473209
0.9111	High Similarity	NPC60667
0.9111	High Similarity	NPC151113
0.9104	High Similarity	NPC108113
0.9104	High Similarity	NPC223354
0.9104	High Similarity	NPC93756
0.9085	High Similarity	NPC5173
0.9078	High Similarity	NPC218300
0.9078	High Similarity	NPC283234
0.9078	High Similarity	NPC23728
0.9078	High Similarity	NPC14001
0.9078	High Similarity	NPC296998
0.9078	High Similarity	NPC166757
0.9078	High Similarity	NPC110303
0.9078	High Similarity	NPC282335
0.9078	High Similarity	NPC473077
0.9071	High Similarity	NPC209040
0.9071	High Similarity	NPC469953
0.9071	High Similarity	NPC273538
0.9071	High Similarity	NPC294365
0.9071	High Similarity	NPC131579
0.9071	High Similarity	NPC171656
0.9071	High Similarity	NPC216538
0.9071	High Similarity	NPC131568
0.9065	High Similarity	NPC227579
0.9065	High Similarity	NPC296917
0.9065	High Similarity	NPC324436
0.9065	High Similarity	NPC194432
0.9065	High Similarity	NPC223500
0.9065	High Similarity	NPC144499
0.9065	High Similarity	NPC66515
0.9065	High Similarity	NPC328164
0.9065	High Similarity	NPC182852
0.9065	High Similarity	NPC306829
0.9065	High Similarity	NPC228504
0.9065	High Similarity	NPC200694
0.9065	High Similarity	NPC125855
0.9065	High Similarity	NPC76338
0.9065	High Similarity	NPC64915
0.9065	High Similarity	NPC324134
0.9065	High Similarity	NPC40833
0.9065	High Similarity	NPC177354
0.9065	High Similarity	NPC161506
0.9065	High Similarity	NPC148757
0.9065	High Similarity	NPC166934
0.9065	High Similarity	NPC37496
0.9065	High Similarity	NPC167624
0.9065	High Similarity	NPC107572
0.9065	High Similarity	NPC1089
0.9065	High Similarity	NPC78
0.9065	High Similarity	NPC166482
0.9065	High Similarity	NPC220998
0.9065	High Similarity	NPC76372
0.9065	High Similarity	NPC10937
0.9065	High Similarity	NPC32739
0.9065	High Similarity	NPC265040
0.9058	High Similarity	NPC221173
0.9058	High Similarity	NPC69769
0.9058	High Similarity	NPC171094
0.9051	High Similarity	NPC248995
0.9051	High Similarity	NPC254168
0.9051	High Similarity	NPC470671
0.9051	High Similarity	NPC276905
0.9051	High Similarity	NPC272844
0.9051	High Similarity	NPC474487
0.9051	High Similarity	NPC474504
0.9051	High Similarity	NPC470672
0.9044	High Similarity	NPC234133
0.9044	High Similarity	NPC13408
0.9044	High Similarity	NPC156910
0.9044	High Similarity	NPC231772
0.9044	High Similarity	NPC473887
0.9044	High Similarity	NPC127447
0.9044	High Similarity	NPC194281
0.9044	High Similarity	NPC47815

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 NPC46869 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	1039
0.2-0.3	1534
0.3-0.4	2818
0.4-0.5	1824
0.5-0.6	1062
0.6-0.7	320
0.7-0.8	105
0.8-0.85	31
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9185	High Similarity	NPD2796	Approved
0.9071	High Similarity	NPD4378	Clinical (unspecified phase)
0.8936	High Similarity	NPD7410	Clinical (unspecified phase)
0.8705	High Similarity	NPD1550	Clinical (unspecified phase)
0.8705	High Similarity	NPD1552	Clinical (unspecified phase)
0.8643	High Similarity	NPD1549	Phase 2
0.8582	High Similarity	NPD1243	Approved
0.8571	High Similarity	NPD7411	Suspended
0.8561	High Similarity	NPD1510	Phase 2
0.854	High Similarity	NPD1240	Approved
0.8514	High Similarity	NPD6801	Discontinued
0.8472	Intermediate Similarity	NPD6799	Approved
0.8456	Intermediate Similarity	NPD7819	Suspended
0.8456	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD920	Approved
0.8417	Intermediate Similarity	NPD1607	Approved
0.8403	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD4380	Phase 2
0.8298	Intermediate Similarity	NPD3748	Approved
0.8289	Intermediate Similarity	NPD7075	Discontinued
0.8288	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD6599	Discontinued
0.8219	Intermediate Similarity	NPD1511	Approved
0.8212	Intermediate Similarity	NPD2801	Approved
0.8194	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2800	Approved
0.8182	Intermediate Similarity	NPD5494	Approved
0.8158	Intermediate Similarity	NPD3817	Phase 2
0.8156	Intermediate Similarity	NPD6651	Approved
0.8146	Intermediate Similarity	NPD1934	Approved
0.8129	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1512	Approved
0.8069	Intermediate Similarity	NPD2654	Approved
0.8054	Intermediate Similarity	NPD5403	Approved
0.8052	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD5401	Approved
0.8014	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD919	Approved
0.7987	Intermediate Similarity	NPD7768	Phase 2
0.7986	Intermediate Similarity	NPD6832	Phase 2
0.7975	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD2799	Discontinued
0.7898	Intermediate Similarity	NPD6959	Discontinued
0.7898	Intermediate Similarity	NPD1247	Approved
0.7872	Intermediate Similarity	NPD1296	Phase 2
0.7872	Intermediate Similarity	NPD2313	Discontinued
0.7871	Intermediate Similarity	NPD3882	Suspended
0.7832	Intermediate Similarity	NPD5124	Phase 1
0.7832	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3749	Approved
0.78	Intermediate Similarity	NPD2532	Approved
0.78	Intermediate Similarity	NPD2534	Approved
0.78	Intermediate Similarity	NPD2533	Approved
0.777	Intermediate Similarity	NPD3266	Approved
0.777	Intermediate Similarity	NPD3267	Approved
0.777	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6166	Phase 2
0.775	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD2935	Discontinued
0.774	Intermediate Similarity	NPD1551	Phase 2
0.7727	Intermediate Similarity	NPD1241	Discontinued
0.7714	Intermediate Similarity	NPD2798	Approved
0.7692	Intermediate Similarity	NPD5402	Approved
0.7688	Intermediate Similarity	NPD3926	Phase 2
0.7681	Intermediate Similarity	NPD3972	Approved
0.7681	Intermediate Similarity	NPD9717	Approved
0.7671	Intermediate Similarity	NPD7033	Discontinued
0.7654	Intermediate Similarity	NPD3818	Discontinued
0.7639	Intermediate Similarity	NPD4307	Phase 2
0.7625	Intermediate Similarity	NPD6232	Discontinued
0.7622	Intermediate Similarity	NPD3268	Approved
0.7622	Intermediate Similarity	NPD5953	Discontinued
0.7619	Intermediate Similarity	NPD6100	Approved
0.7619	Intermediate Similarity	NPD6099	Approved
0.7609	Intermediate Similarity	NPD422	Phase 1
0.7607	Intermediate Similarity	NPD7286	Phase 2
0.7607	Intermediate Similarity	NPD7054	Approved
0.7593	Intermediate Similarity	NPD7473	Discontinued
0.7589	Intermediate Similarity	NPD1019	Discontinued
0.7586	Intermediate Similarity	NPD1933	Approved
0.7582	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2344	Approved
0.7561	Intermediate Similarity	NPD7472	Approved
0.7561	Intermediate Similarity	NPD7074	Phase 3
0.7548	Intermediate Similarity	NPD6585	Discontinued
0.7533	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2403	Approved
0.7518	Intermediate Similarity	NPD2797	Approved
0.7518	Intermediate Similarity	NPD1203	Approved
0.7515	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD5890	Approved
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5889	Approved
0.7484	Intermediate Similarity	NPD3226	Approved
0.7483	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7251	Discontinued
0.747	Intermediate Similarity	NPD6559	Discontinued
0.7466	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2346	Discontinued
0.7447	Intermediate Similarity	NPD3225	Approved
0.7445	Intermediate Similarity	NPD1548	Phase 1
0.7432	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4308	Phase 3
0.7425	Intermediate Similarity	NPD7808	Phase 3
0.7423	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4628	Phase 3
0.7397	Intermediate Similarity	NPD3142	Approved
0.7397	Intermediate Similarity	NPD3140	Approved
0.7394	Intermediate Similarity	NPD5844	Phase 1
0.7368	Intermediate Similarity	NPD2309	Approved
0.7361	Intermediate Similarity	NPD4908	Phase 1
0.7338	Intermediate Similarity	NPD17	Approved
0.7333	Intermediate Similarity	NPD1471	Phase 3
0.7321	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4360	Phase 2
0.7299	Intermediate Similarity	NPD4363	Phase 3
0.7279	Intermediate Similarity	NPD943	Approved
0.7278	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7262	Intermediate Similarity	NPD6104	Discontinued
0.7257	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4361	Phase 2
0.7255	Intermediate Similarity	NPD3887	Approved
0.725	Intermediate Similarity	NPD4288	Approved
0.7246	Intermediate Similarity	NPD1729	Discontinued
0.7234	Intermediate Similarity	NPD1610	Phase 2
0.7229	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2353	Approved
0.7216	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1876	Approved
0.7195	Intermediate Similarity	NPD5710	Approved
0.7195	Intermediate Similarity	NPD5711	Approved
0.7194	Intermediate Similarity	NPD9545	Approved
0.7192	Intermediate Similarity	NPD4625	Phase 3
0.7183	Intermediate Similarity	NPD1608	Approved
0.7174	Intermediate Similarity	NPD9493	Approved
0.7171	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD411	Approved
0.7143	Intermediate Similarity	NPD1651	Approved
0.7133	Intermediate Similarity	NPD4749	Approved
0.7132	Intermediate Similarity	NPD5535	Approved
0.7125	Intermediate Similarity	NPD6280	Approved
0.7125	Intermediate Similarity	NPD6279	Approved
0.7124	Intermediate Similarity	NPD1652	Phase 2
0.7114	Intermediate Similarity	NPD447	Suspended
0.7091	Intermediate Similarity	NPD7229	Phase 3
0.707	Intermediate Similarity	NPD5049	Phase 3
0.7059	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7458	Discontinued
0.7032	Intermediate Similarity	NPD2354	Approved
0.7027	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5691	Approved
0.7006	Intermediate Similarity	NPD4661	Approved
0.7006	Intermediate Similarity	NPD4662	Approved
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD230	Phase 1
0.6993	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6808	Phase 2
0.6975	Remote Similarity	NPD1465	Phase 2
0.6968	Remote Similarity	NPD7003	Approved
0.6966	Remote Similarity	NPD8651	Approved
0.6957	Remote Similarity	NPD7584	Approved
0.6943	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7199	Phase 2
0.6928	Remote Similarity	NPD4476	Approved
0.6928	Remote Similarity	NPD4477	Approved
0.6914	Remote Similarity	NPD6844	Discontinued
0.6913	Remote Similarity	NPD3764	Approved
0.6906	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6355	Discontinued
0.6886	Remote Similarity	NPD3787	Discontinued
0.6883	Remote Similarity	NPD6005	Phase 3
0.6883	Remote Similarity	NPD6002	Phase 3
0.6883	Remote Similarity	NPD6004	Phase 3
0.6883	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1201	Approved
0.6875	Remote Similarity	NPD4287	Approved
0.6875	Remote Similarity	NPD1281	Approved
0.6871	Remote Similarity	NPD5761	Phase 2
0.6871	Remote Similarity	NPD5760	Phase 2
0.6867	Remote Similarity	NPD6233	Phase 2

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