NPASS Compound

Structure

CID292460 OpenBabel06191716102D 22 25 0 0 0 0 0 0 0 0999 V2000 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 10 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 11 15 1 0 0 0 0 11 18 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.07
Volume:	291.222
LogP:	3.669
LogD:	3.055
LogS:	-4.927
# Rotatable Bonds:	2
TPSA:	57.9
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.727
Synthetic Accessibility Score:	2.351
Fsp3:	0.118
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:	-4.638
MDCK Permeability:	2.1092273527756333e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	92.62110900878906%
Volume Distribution (VD):	0.624
Pgp-substrate:	5.024368762969971%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.569
CYP2C19-inhibitor:	0.961
CYP2C19-substrate:	0.129
CYP2C9-inhibitor:	0.853
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.843
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.903
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	6.992
Half-life (T1/2):	0.201

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.793
AMES Toxicity:	0.67
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.236
Skin Sensitization:	0.55
Carcinogencity:	0.897
Eye Corrosion:	0.004
Eye Irritation:	0.659
Respiratory Toxicity:	0.426

Download Data

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

Natural Product: NPC292460

Natural Product ID:	NPC292460
*Common Name:**	9-Methoxy-6-Phenyl-[1,3]Dioxolo[4,5-G]Chromen-8-One
IUPAC Name:	9-methoxy-6-phenyl-[1,3]dioxolo[4,5-g]chromen-8-one
Synonyms:
Standard InCHIKey:	NGLORVNWTNPBMU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H12O5/c1-19-17-15-11(18)7-12(10-5-3-2-4-6-10)22-13(15)8-14-16(17)21-9-20-14/h2-8H,9H2,1H3
SMILES:	COc1c2c(=O)cc(c3ccccc3)oc2cc2c1OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL186478
PubChem CID:	189609
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002590] 5-O-methylated flavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO7193	Persicaria lapathifolia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678656]
NPO1351	Artemisia vulgaris	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO1351	Artemisia vulgaris	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1351	Artemisia vulgaris	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO1351	Artemisia vulgaris	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO30740	Polygonum lapathifolium	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1351	Artemisia vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7193	Persicaria lapathifolia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1351	Artemisia vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30740	Polygonum lapathifolium	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1351	Artemisia vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7193	Persicaria lapathifolia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1351	Artemisia vulgaris	Species	Asteraceae	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	2
Others	2

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	EC50	=	4400.0	nM	PMID[507223]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Amax	=	1.5	pmoles	PMID[507223]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100000.0	nM	PMID[507223]
NPT1178	Cell Line	KB 3-1	Homo sapiens	IC50	>	100000.0	nM	PMID[507223]
NPT35	Others	n.a.		CLogD	=	3.1	n.a.	PMID[507223]

☑ 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 NPC292460 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	552
0.1-0.2	2165
0.2-0.3	5297
0.3-0.4	11441
0.4-0.5	5835
0.5-0.6	4031
0.6-0.7	5817
0.7-0.8	4789
0.8-0.85	1787
0.85-0.9	822
0.9-0.95	141
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC257914
0.9667	High Similarity	NPC104459
0.9667	High Similarity	NPC238405
0.9662	High Similarity	NPC244371
0.9603	High Similarity	NPC131557
0.96	High Similarity	NPC258644
0.9595	High Similarity	NPC148497
0.9595	High Similarity	NPC153008
0.953	High Similarity	NPC279930
0.953	High Similarity	NPC478213
0.9467	High Similarity	NPC284353
0.9463	High Similarity	NPC68882
0.9452	High Similarity	NPC110639
0.9452	High Similarity	NPC40818
0.9452	High Similarity	NPC14958
0.9452	High Similarity	NPC106461
0.9452	High Similarity	NPC215932
0.94	High Similarity	NPC57211
0.9396	High Similarity	NPC279061
0.9388	High Similarity	NPC205522
0.9388	High Similarity	NPC85233
0.9351	High Similarity	NPC18284
0.9351	High Similarity	NPC273021
0.9351	High Similarity	NPC478199
0.9342	High Similarity	NPC310206
0.9338	High Similarity	NPC478238
0.9333	High Similarity	NPC52623
0.932	High Similarity	NPC302408
0.932	High Similarity	NPC283002
0.9315	High Similarity	NPC23955
0.9281	High Similarity	NPC215375
0.9281	High Similarity	NPC62518
0.9276	High Similarity	NPC155063
0.9262	High Similarity	NPC69752
0.9252	High Similarity	NPC136278
0.9252	High Similarity	NPC165512
0.9252	High Similarity	NPC296575
0.9252	High Similarity	NPC224687
0.9247	High Similarity	NPC70853
0.9247	High Similarity	NPC9966
0.9236	High Similarity	NPC76482
0.9226	High Similarity	NPC469575
0.9221	High Similarity	NPC269906
0.9216	High Similarity	NPC167595
0.9211	High Similarity	NPC18954
0.92	High Similarity	NPC259058
0.92	High Similarity	NPC201547
0.92	High Similarity	NPC306821
0.9195	High Similarity	NPC63256
0.9195	High Similarity	NPC10304
0.9189	High Similarity	NPC231013
0.9184	High Similarity	NPC113089
0.9178	High Similarity	NPC214919
0.9178	High Similarity	NPC124467
0.9178	High Similarity	NPC29536
0.9172	High Similarity	NPC113093
0.9167	High Similarity	NPC470178
0.9161	High Similarity	NPC34376
0.9161	High Similarity	NPC162668
0.9161	High Similarity	NPC295009
0.9161	High Similarity	NPC260640
0.9156	High Similarity	NPC113055
0.9145	High Similarity	NPC186507
0.9139	High Similarity	NPC208043
0.9139	High Similarity	NPC226973
0.9133	High Similarity	NPC238366
0.9133	High Similarity	NPC181250
0.9108	High Similarity	NPC187923
0.9103	High Similarity	NPC302741
0.9097	High Similarity	NPC285973
0.9097	High Similarity	NPC225624
0.9091	High Similarity	NPC19097
0.9085	High Similarity	NPC34725
0.9085	High Similarity	NPC241774
0.9085	High Similarity	NPC122623
0.9085	High Similarity	NPC276059
0.9079	High Similarity	NPC188203
0.9079	High Similarity	NPC256283
0.9079	High Similarity	NPC131624
0.9079	High Similarity	NPC239128
0.9079	High Similarity	NPC156222
0.9079	High Similarity	NPC187498
0.9079	High Similarity	NPC83508
0.9079	High Similarity	NPC100887
0.9079	High Similarity	NPC198826
0.9079	High Similarity	NPC301323
0.9079	High Similarity	NPC212678
0.9079	High Similarity	NPC241498
0.9079	High Similarity	NPC275836
0.9079	High Similarity	NPC25270
0.9079	High Similarity	NPC134677
0.9079	High Similarity	NPC222830
0.9079	High Similarity	NPC162313
0.9079	High Similarity	NPC57030
0.9079	High Similarity	NPC275722
0.9079	High Similarity	NPC71334
0.9079	High Similarity	NPC301123
0.9079	High Similarity	NPC120163
0.9079	High Similarity	NPC293183
0.9062	High Similarity	NPC223375
0.9062	High Similarity	NPC475825
0.906	High Similarity	NPC216314
0.906	High Similarity	NPC120924
0.906	High Similarity	NPC310259
0.906	High Similarity	NPC195919
0.9038	High Similarity	NPC94155
0.9026	High Similarity	NPC257277
0.9026	High Similarity	NPC301897
0.902	High Similarity	NPC231018
0.902	High Similarity	NPC183878
0.902	High Similarity	NPC86485
0.902	High Similarity	NPC47781
0.902	High Similarity	NPC160951
0.902	High Similarity	NPC22519
0.902	High Similarity	NPC69394
0.902	High Similarity	NPC476289
0.902	High Similarity	NPC255350
0.902	High Similarity	NPC472408
0.902	High Similarity	NPC145379
0.902	High Similarity	NPC274327
0.902	High Similarity	NPC176775
0.9013	High Similarity	NPC117579
0.9013	High Similarity	NPC308451
0.9007	High Similarity	NPC328119
0.9006	High Similarity	NPC72455
0.9	High Similarity	NPC12200
0.9	High Similarity	NPC299923
0.9	High Similarity	NPC117463
0.8994	High Similarity	NPC42892
0.8994	High Similarity	NPC135345
0.8993	High Similarity	NPC471590
0.8981	High Similarity	NPC125991
0.898	High Similarity	NPC58229
0.8961	High Similarity	NPC201451
0.8961	High Similarity	NPC189960
0.8961	High Similarity	NPC213622
0.8961	High Similarity	NPC146165
0.8961	High Similarity	NPC4455
0.8961	High Similarity	NPC227325
0.8961	High Similarity	NPC20830
0.8961	High Similarity	NPC2476
0.8961	High Similarity	NPC138360
0.8961	High Similarity	NPC280339
0.8961	High Similarity	NPC32557
0.8961	High Similarity	NPC183597
0.8961	High Similarity	NPC50715
0.8961	High Similarity	NPC128863
0.8961	High Similarity	NPC44079
0.8961	High Similarity	NPC256612
0.8961	High Similarity	NPC163780
0.8961	High Similarity	NPC201136
0.8961	High Similarity	NPC26227
0.8961	High Similarity	NPC196439
0.8961	High Similarity	NPC167815
0.8961	High Similarity	NPC92659
0.8954	High Similarity	NPC35544
0.8954	High Similarity	NPC166201
0.8954	High Similarity	NPC142540
0.8954	High Similarity	NPC104728
0.8947	High Similarity	NPC234152
0.8947	High Similarity	NPC184136
0.894	High Similarity	NPC261548
0.894	High Similarity	NPC195202
0.8938	High Similarity	NPC475942
0.8938	High Similarity	NPC469931
0.8938	High Similarity	NPC471287
0.8938	High Similarity	NPC45638
0.8938	High Similarity	NPC226294
0.8938	High Similarity	NPC58053
0.8938	High Similarity	NPC186807
0.8938	High Similarity	NPC201292
0.8938	High Similarity	NPC41853
0.8938	High Similarity	NPC93337
0.8938	High Similarity	NPC105025
0.8926	High Similarity	NPC182842
0.8926	High Similarity	NPC293201
0.8924	High Similarity	NPC110257
0.8917	High Similarity	NPC470756
0.8917	High Similarity	NPC182045
0.8903	High Similarity	NPC49824
0.8903	High Similarity	NPC247017
0.8903	High Similarity	NPC43243
0.8903	High Similarity	NPC245546
0.8903	High Similarity	NPC178854
0.8903	High Similarity	NPC266960
0.8903	High Similarity	NPC98661
0.8896	High Similarity	NPC276409
0.8896	High Similarity	NPC472915
0.8896	High Similarity	NPC280937
0.8896	High Similarity	NPC250822
0.8896	High Similarity	NPC75279
0.8896	High Similarity	NPC128961
0.8889	High Similarity	NPC474663
0.8889	High Similarity	NPC474170
0.8889	High Similarity	NPC149614
0.8889	High Similarity	NPC198615
0.8889	High Similarity	NPC472535
0.8889	High Similarity	NPC474388
0.8882	High Similarity	NPC137062
0.8882	High Similarity	NPC216318

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 NPC292460 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	461
0.1-0.2	1016
0.2-0.3	1908
0.3-0.4	2740
0.4-0.5	1723
0.5-0.6	856
0.6-0.7	303
0.7-0.8	108
0.8-0.85	23
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.902	High Similarity	NPD2801	Approved
0.8875	High Similarity	NPD3818	Discontinued
0.8854	High Similarity	NPD5494	Approved
0.8718	High Similarity	NPD3817	Phase 2
0.8627	High Similarity	NPD6980	Clinical (unspecified phase)
0.8606	High Similarity	NPD4338	Clinical (unspecified phase)
0.859	High Similarity	NPD1934	Approved
0.8589	High Similarity	NPD7054	Approved
0.8562	High Similarity	NPD1247	Approved
0.8553	High Similarity	NPD1511	Approved
0.8544	High Similarity	NPD3882	Suspended
0.8537	High Similarity	NPD7472	Approved
0.8442	Intermediate Similarity	NPD1512	Approved
0.8424	Intermediate Similarity	NPD7074	Phase 3
0.8383	Intermediate Similarity	NPD7808	Phase 3
0.8373	Intermediate Similarity	NPD6797	Phase 2
0.8333	Intermediate Similarity	NPD2796	Approved
0.8323	Intermediate Similarity	NPD919	Approved
0.8323	Intermediate Similarity	NPD7251	Discontinued
0.8302	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD3926	Phase 2
0.8188	Intermediate Similarity	NPD1933	Approved
0.8141	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6799	Approved
0.8072	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6166	Phase 2
0.8038	Intermediate Similarity	NPD920	Approved
0.8025	Intermediate Similarity	NPD5402	Approved
0.7962	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6232	Discontinued
0.7935	Intermediate Similarity	NPD1243	Approved
0.7929	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7473	Discontinued
0.7911	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1510	Phase 2
0.7895	Intermediate Similarity	NPD6559	Discontinued
0.7892	Intermediate Similarity	NPD7199	Phase 2
0.7871	Intermediate Similarity	NPD1549	Phase 2
0.7866	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7819	Suspended
0.7824	Intermediate Similarity	NPD5844	Phase 1
0.7798	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3748	Approved
0.7791	Intermediate Similarity	NPD6801	Discontinued
0.7785	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD4380	Phase 2
0.7763	Intermediate Similarity	NPD1240	Approved
0.7756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD447	Suspended
0.7711	Intermediate Similarity	NPD7075	Discontinued
0.7688	Intermediate Similarity	NPD5401	Approved
0.7688	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD37	Approved
0.7662	Intermediate Similarity	NPD1607	Approved
0.7658	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4965	Approved
0.7651	Intermediate Similarity	NPD4967	Phase 2
0.7651	Intermediate Similarity	NPD4966	Approved
0.7636	Intermediate Similarity	NPD1465	Phase 2
0.7622	Intermediate Similarity	NPD7411	Suspended
0.7605	Intermediate Similarity	NPD3749	Approved
0.7595	Intermediate Similarity	NPD2800	Approved
0.7593	Intermediate Similarity	NPD5403	Approved
0.756	Intermediate Similarity	NPD6234	Discontinued
0.7558	Intermediate Similarity	NPD3751	Discontinued
0.7547	Intermediate Similarity	NPD3750	Approved
0.7546	Intermediate Similarity	NPD1653	Approved
0.7532	Intermediate Similarity	NPD943	Approved
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.7485	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2532	Approved
0.7469	Intermediate Similarity	NPD2534	Approved
0.7469	Intermediate Similarity	NPD2533	Approved
0.7429	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1551	Phase 2
0.7403	Intermediate Similarity	NPD2313	Discontinued
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6832	Phase 2
0.7384	Intermediate Similarity	NPD5242	Approved
0.7375	Intermediate Similarity	NPD2654	Approved
0.7372	Intermediate Similarity	NPD230	Phase 1
0.7368	Intermediate Similarity	NPD2798	Approved
0.7368	Intermediate Similarity	NPD6959	Discontinued
0.7358	Intermediate Similarity	NPD2344	Approved
0.7341	Intermediate Similarity	NPD2403	Approved
0.7326	Intermediate Similarity	NPD5005	Approved
0.7326	Intermediate Similarity	NPD5006	Approved
0.7318	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6386	Approved
0.7305	Intermediate Similarity	NPD6385	Approved
0.7289	Intermediate Similarity	NPD3226	Approved
0.7288	Intermediate Similarity	NPD7685	Pre-registration
0.7278	Intermediate Similarity	NPD5353	Approved
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3705	Approved
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7228	Approved
0.725	Intermediate Similarity	NPD2346	Discontinued
0.7241	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7768	Phase 2
0.7233	Intermediate Similarity	NPD2799	Discontinued
0.7212	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4420	Approved
0.7197	Intermediate Similarity	NPD1613	Approved
0.7197	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3267	Approved
0.719	Intermediate Similarity	NPD3266	Approved
0.7178	Intermediate Similarity	NPD2309	Approved
0.7162	Intermediate Similarity	NPD5536	Phase 2
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7133	Intermediate Similarity	NPD17	Approved
0.7125	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4628	Phase 3
0.7097	Intermediate Similarity	NPD3018	Phase 2
0.7095	Intermediate Similarity	NPD7240	Approved
0.7089	Intermediate Similarity	NPD4307	Phase 2
0.7078	Intermediate Similarity	NPD1203	Approved
0.707	Intermediate Similarity	NPD1296	Phase 2
0.7059	Intermediate Similarity	NPD6844	Discontinued
0.7045	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5953	Discontinued
0.7037	Intermediate Similarity	NPD6780	Approved
0.7037	Intermediate Similarity	NPD6781	Approved
0.7037	Intermediate Similarity	NPD6777	Approved
0.7037	Intermediate Similarity	NPD6776	Approved
0.7037	Intermediate Similarity	NPD6778	Approved
0.7037	Intermediate Similarity	NPD6779	Approved
0.7037	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6782	Approved
0.7035	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1019	Discontinued
0.7029	Intermediate Similarity	NPD7229	Phase 3
0.7022	Intermediate Similarity	NPD7286	Phase 2
0.7019	Intermediate Similarity	NPD7033	Discontinued
0.7019	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8313	Approved
0.7017	Intermediate Similarity	NPD8312	Approved
0.7006	Intermediate Similarity	NPD3027	Phase 3
0.6995	Remote Similarity	NPD8434	Phase 2
0.6993	Remote Similarity	NPD1608	Approved
0.6993	Remote Similarity	NPD2981	Phase 2
0.6993	Remote Similarity	NPD9717	Approved
0.6987	Remote Similarity	NPD9494	Approved
0.6982	Remote Similarity	NPD7458	Discontinued
0.6975	Remote Similarity	NPD6100	Approved
0.6975	Remote Similarity	NPD6099	Approved
0.697	Remote Similarity	NPD6190	Approved
0.6962	Remote Similarity	NPD3268	Approved
0.6948	Remote Similarity	NPD2982	Phase 2
0.6948	Remote Similarity	NPD2983	Phase 2
0.6941	Remote Similarity	NPD7028	Phase 2
0.6932	Remote Similarity	NPD5710	Approved
0.6932	Remote Similarity	NPD5711	Approved
0.6928	Remote Similarity	NPD422	Phase 1
0.6927	Remote Similarity	NPD7435	Discontinued
0.6927	Remote Similarity	NPD7698	Approved
0.6927	Remote Similarity	NPD7696	Phase 3
0.6927	Remote Similarity	NPD7697	Approved
0.6918	Remote Similarity	NPD6233	Phase 2
0.6914	Remote Similarity	NPD4308	Phase 3
0.6907	Remote Similarity	NPD7584	Approved
0.6903	Remote Similarity	NPD3225	Approved
0.6894	Remote Similarity	NPD6651	Approved
0.6892	Remote Similarity	NPD1241	Discontinued
0.6891	Remote Similarity	NPD7870	Phase 2
0.6891	Remote Similarity	NPD7871	Phase 2
0.6887	Remote Similarity	NPD1548	Phase 1
0.6886	Remote Similarity	NPD4357	Discontinued
0.6883	Remote Similarity	NPD3972	Approved
0.6879	Remote Similarity	NPD4288	Approved
0.6872	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6280	Approved
0.686	Remote Similarity	NPD6279	Approved
0.6859	Remote Similarity	NPD2797	Approved
0.6855	Remote Similarity	NPD411	Approved
0.6853	Remote Similarity	NPD7783	Phase 2
0.6853	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3146	Approved
0.6845	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9268	Approved
0.6839	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8151	Discontinued
0.6836	Remote Similarity	NPD6808	Phase 2
0.6835	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2353	Approved
0.6829	Remote Similarity	NPD2355	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data