NPASS Compound

Structure

NPC295009 OpenBabel07101719512D 23 26 0 0 0 0 0 0 0 0999 V2000 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 0.1910 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 4.4152 -1.3090 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 0.1910 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 6.1472 -0.3090 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 3.5491 0.1910 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 0.9511 -0.3090 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 6.1472 -1.3090 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 -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 1 20 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 9 2 0 0 0 0 5 11 2 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 16 2 0 0 0 0 15 18 2 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.06
Volume:	300.012
LogP:	3.167
LogD:	2.806
LogS:	-4.006
# Rotatable Bonds:	2
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.784
Synthetic Accessibility Score:	2.528
Fsp3:	0.118
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:	-4.759
MDCK Permeability:	3.2779375032987446e-05
Pgp-inhibitor:	0.192
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	96.29209899902344%
Volume Distribution (VD):	0.494
Pgp-substrate:	5.055631160736084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.37
CYP2C19-inhibitor:	0.956
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.861
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.877
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.136

ADMET: Excretion

Clearance (CL):	7.886
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.629
AMES Toxicity:	0.185
Rat Oral Acute Toxicity:	0.37
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.49
Carcinogencity:	0.86
Eye Corrosion:	0.011
Eye Irritation:	0.757
Respiratory Toxicity:	0.232

Download Data

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

Natural Product: NPC295009

Natural Product ID:	NPC295009
*Common Name:**	Irisone A
IUPAC Name:	9-hydroxy-7-(2-methoxyphenyl)-[1,3]dioxolo[4,5-g]chromen-8-one
Synonyms:
Standard InCHIKey:	DWGZUNVIWVMPBQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H12O6/c1-20-11-5-3-2-4-9(11)10-7-21-12-6-13-17(23-8-22-13)16(19)14(12)15(10)18/h2-7,19H,8H2,1H3
SMILES:	COc1ccccc1c1coc2c(c1=O)c(O)c1c(c2)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509631
PubChem CID:	5491929
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones

*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
NPO14556	Iris missouriensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3655793]
NPO14556	Iris missouriensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3734815]
NPO14556	Iris missouriensis	Species	Iridaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	50.0	ug ml-1	PMID[489924]

☑ 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 NPC295009 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	445
0.1-0.2	1983
0.2-0.3	4600
0.3-0.4	10727
0.4-0.5	7138
0.5-0.6	3835
0.6-0.7	5076
0.7-0.8	5317
0.8-0.85	1897
0.85-0.9	1257
0.9-0.95	395
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC260640
0.9934	High Similarity	NPC285973
0.9934	High Similarity	NPC225624
0.9868	High Similarity	NPC215375
0.9868	High Similarity	NPC62518
0.9803	High Similarity	NPC167595
0.9539	High Similarity	NPC291802
0.9539	High Similarity	NPC148497
0.9539	High Similarity	NPC181209
0.9539	High Similarity	NPC216769
0.9539	High Similarity	NPC35763
0.9539	High Similarity	NPC153008
0.9539	High Similarity	NPC35544
0.9539	High Similarity	NPC131266
0.9539	High Similarity	NPC121522
0.9539	High Similarity	NPC209487
0.9539	High Similarity	NPC100971
0.9539	High Similarity	NPC100263
0.9539	High Similarity	NPC245382
0.9539	High Similarity	NPC104728
0.9539	High Similarity	NPC269451
0.949	High Similarity	NPC470178
0.9487	High Similarity	NPC162668
0.9477	High Similarity	NPC124714
0.9477	High Similarity	NPC478213
0.9474	High Similarity	NPC45291
0.9474	High Similarity	NPC19980
0.9474	High Similarity	NPC288316
0.9416	High Similarity	NPC39184
0.9408	High Similarity	NPC156953
0.9408	High Similarity	NPC10467
0.9351	High Similarity	NPC250557
0.9351	High Similarity	NPC57211
0.9346	High Similarity	NPC279061
0.9346	High Similarity	NPC262623
0.9342	High Similarity	NPC333691
0.9342	High Similarity	NPC142876
0.9342	High Similarity	NPC40290
0.9342	High Similarity	NPC139293
0.9342	High Similarity	NPC195763
0.9342	High Similarity	NPC200060
0.9342	High Similarity	NPC264550
0.9342	High Similarity	NPC264289
0.9342	High Similarity	NPC69430
0.9313	High Similarity	NPC42892
0.9313	High Similarity	NPC76482
0.9304	High Similarity	NPC469575
0.929	High Similarity	NPC18954
0.929	High Similarity	NPC478238
0.929	High Similarity	NPC130589
0.929	High Similarity	NPC134287
0.9286	High Similarity	NPC52623
0.9281	High Similarity	NPC234152
0.9281	High Similarity	NPC239363
0.9276	High Similarity	NPC194653
0.9276	High Similarity	NPC183655
0.9276	High Similarity	NPC287395
0.9276	High Similarity	NPC139364
0.9276	High Similarity	NPC80710
0.9276	High Similarity	NPC218490
0.9276	High Similarity	NPC254702
0.9276	High Similarity	NPC203747
0.9259	High Similarity	NPC205076
0.9259	High Similarity	NPC307518
0.9259	High Similarity	NPC48773
0.9255	High Similarity	NPC471287
0.9241	High Similarity	NPC470756
0.9226	High Similarity	NPC471981
0.9216	High Similarity	NPC102003
0.9216	High Similarity	NPC92722
0.9211	High Similarity	NPC188074
0.9211	High Similarity	NPC125449
0.9198	High Similarity	NPC105511
0.9198	High Similarity	NPC224462
0.9198	High Similarity	NPC212748
0.9193	High Similarity	NPC471288
0.9182	High Similarity	NPC81679
0.9177	High Similarity	NPC269906
0.9172	High Similarity	NPC99597
0.9172	High Similarity	NPC474990
0.9172	High Similarity	NPC78103
0.9172	High Similarity	NPC210084
0.9167	High Similarity	NPC20830
0.9167	High Similarity	NPC2928
0.9167	High Similarity	NPC256612
0.9167	High Similarity	NPC213622
0.9161	High Similarity	NPC57030
0.9161	High Similarity	NPC275722
0.9161	High Similarity	NPC131624
0.9161	High Similarity	NPC25270
0.9161	High Similarity	NPC292460
0.9161	High Similarity	NPC100887
0.9161	High Similarity	NPC71334
0.9161	High Similarity	NPC212678
0.9161	High Similarity	NPC239128
0.9161	High Similarity	NPC293183
0.9161	High Similarity	NPC187498
0.9161	High Similarity	NPC162313
0.9161	High Similarity	NPC188203
0.9161	High Similarity	NPC256283
0.9161	High Similarity	NPC156222
0.9161	High Similarity	NPC241498
0.9161	High Similarity	NPC83508
0.9161	High Similarity	NPC120163
0.9161	High Similarity	NPC275836
0.9161	High Similarity	NPC198826
0.9161	High Similarity	NPC301323
0.9161	High Similarity	NPC222830
0.915	High Similarity	NPC15329
0.915	High Similarity	NPC131451
0.9146	High Similarity	NPC472607
0.9145	High Similarity	NPC143903
0.9145	High Similarity	NPC12377
0.9145	High Similarity	NPC226987
0.9141	High Similarity	NPC475825
0.9141	High Similarity	NPC223375
0.9141	High Similarity	NPC235575
0.9136	High Similarity	NPC45638
0.9136	High Similarity	NPC105025
0.9136	High Similarity	NPC186807
0.9136	High Similarity	NPC475942
0.9136	High Similarity	NPC201292
0.9136	High Similarity	NPC93337
0.9136	High Similarity	NPC469931
0.9136	High Similarity	NPC58053
0.9136	High Similarity	NPC226294
0.913	High Similarity	NPC113093
0.9119	High Similarity	NPC471290
0.9119	High Similarity	NPC94155
0.9108	High Similarity	NPC472916
0.9108	High Similarity	NPC255106
0.9108	High Similarity	NPC235165
0.9103	High Similarity	NPC274327
0.9103	High Similarity	NPC271779
0.9103	High Similarity	NPC244371
0.9103	High Similarity	NPC167091
0.9103	High Similarity	NPC47781
0.9103	High Similarity	NPC69394
0.9103	High Similarity	NPC255350
0.9103	High Similarity	NPC280937
0.9103	High Similarity	NPC292214
0.9103	High Similarity	NPC206238
0.9103	High Similarity	NPC88645
0.9103	High Similarity	NPC176775
0.9103	High Similarity	NPC231018
0.9103	High Similarity	NPC22519
0.9103	High Similarity	NPC183878
0.9103	High Similarity	NPC160951
0.9103	High Similarity	NPC145379
0.9097	High Similarity	NPC256406
0.9091	High Similarity	NPC257714
0.9085	High Similarity	NPC93034
0.9085	High Similarity	NPC119660
0.908	High Similarity	NPC22195
0.908	High Similarity	NPC44558
0.908	High Similarity	NPC21190
0.908	High Similarity	NPC471416
0.908	High Similarity	NPC34287
0.908	High Similarity	NPC183357
0.908	High Similarity	NPC474434
0.9079	High Similarity	NPC224687
0.9074	High Similarity	NPC229729
0.9074	High Similarity	NPC146792
0.9074	High Similarity	NPC135345
0.9074	High Similarity	NPC58716
0.9074	High Similarity	NPC45618
0.9068	High Similarity	NPC470773
0.9068	High Similarity	NPC165720
0.9057	High Similarity	NPC476980
0.9051	High Similarity	NPC472911
0.9051	High Similarity	NPC474208
0.9051	High Similarity	NPC48208
0.9051	High Similarity	NPC472914
0.9051	High Similarity	NPC258644
0.9051	High Similarity	NPC222814
0.9051	High Similarity	NPC245758
0.9051	High Similarity	NPC96167
0.9051	High Similarity	NPC475267
0.9051	High Similarity	NPC162869
0.9051	High Similarity	NPC472913
0.9051	High Similarity	NPC472910
0.9051	High Similarity	NPC474836
0.9051	High Similarity	NPC156057
0.9051	High Similarity	NPC470402
0.9045	High Similarity	NPC138360
0.9045	High Similarity	NPC280339
0.9045	High Similarity	NPC183597
0.9045	High Similarity	NPC196439
0.9045	High Similarity	NPC50715
0.9045	High Similarity	NPC208197
0.9045	High Similarity	NPC163780
0.9045	High Similarity	NPC167815
0.9045	High Similarity	NPC227325
0.9045	High Similarity	NPC92659
0.9045	High Similarity	NPC4455
0.9045	High Similarity	NPC201136
0.9045	High Similarity	NPC146165
0.9045	High Similarity	NPC44079
0.9045	High Similarity	NPC26227
0.9045	High Similarity	NPC2476

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 NPC295009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	964
0.2-0.3	1964
0.3-0.4	2699
0.4-0.5	1731
0.5-0.6	900
0.6-0.7	308
0.7-0.8	117
0.8-0.85	23
0.85-0.9	17
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9313	High Similarity	NPD3818	Discontinued
0.9103	High Similarity	NPD2801	Approved
0.8917	High Similarity	NPD1934	Approved
0.8868	High Similarity	NPD3882	Suspended
0.8802	High Similarity	NPD4338	Clinical (unspecified phase)
0.8788	High Similarity	NPD7054	Approved
0.8735	High Similarity	NPD7074	Phase 3
0.8735	High Similarity	NPD7472	Approved
0.8645	High Similarity	NPD1511	Approved
0.8625	High Similarity	NPD2393	Clinical (unspecified phase)
0.858	High Similarity	NPD4381	Clinical (unspecified phase)
0.8571	High Similarity	NPD6797	Phase 2
0.8535	High Similarity	NPD1512	Approved
0.8521	High Similarity	NPD7251	Discontinued
0.8487	Intermediate Similarity	NPD1510	Phase 2
0.8481	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD5494	Approved
0.8471	Intermediate Similarity	NPD7808	Phase 3
0.8457	Intermediate Similarity	NPD3817	Phase 2
0.8383	Intermediate Similarity	NPD6166	Phase 2
0.8383	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4380	Phase 2
0.8293	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD6232	Discontinued
0.8225	Intermediate Similarity	NPD7473	Discontinued
0.8224	Intermediate Similarity	NPD1240	Approved
0.8224	Intermediate Similarity	NPD943	Approved
0.8204	Intermediate Similarity	NPD1247	Approved
0.8198	Intermediate Similarity	NPD6559	Discontinued
0.8129	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD1607	Approved
0.8101	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1549	Phase 2
0.8084	Intermediate Similarity	NPD6234	Discontinued
0.8063	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7075	Discontinued
0.8012	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD37	Approved
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD919	Approved
0.7962	Intermediate Similarity	NPD2796	Approved
0.7962	Intermediate Similarity	NPD2935	Discontinued
0.7952	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD1465	Phase 2
0.795	Intermediate Similarity	NPD6799	Approved
0.7935	Intermediate Similarity	NPD230	Phase 1
0.7919	Intermediate Similarity	NPD5844	Phase 1
0.791	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6801	Discontinued
0.7882	Intermediate Similarity	NPD7199	Phase 2
0.7866	Intermediate Similarity	NPD1653	Approved
0.7862	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4967	Phase 2
0.7857	Intermediate Similarity	NPD4966	Approved
0.7857	Intermediate Similarity	NPD4965	Approved
0.7844	Intermediate Similarity	NPD7819	Suspended
0.7829	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7791	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.7791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7685	Pre-registration
0.7771	Intermediate Similarity	NPD6599	Discontinued
0.7759	Intermediate Similarity	NPD7228	Approved
0.7725	Intermediate Similarity	NPD7411	Suspended
0.7706	Intermediate Similarity	NPD3749	Approved
0.7697	Intermediate Similarity	NPD920	Approved
0.7677	Intermediate Similarity	NPD3027	Phase 3
0.7673	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD9494	Approved
0.7657	Intermediate Similarity	NPD3751	Discontinued
0.7654	Intermediate Similarity	NPD3750	Approved
0.7595	Intermediate Similarity	NPD1933	Approved
0.7595	Intermediate Similarity	NPD447	Suspended
0.7593	Intermediate Similarity	NPD2800	Approved
0.759	Intermediate Similarity	NPD5403	Approved
0.7588	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5401	Approved
0.7532	Intermediate Similarity	NPD1613	Approved
0.7532	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.7485	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD2798	Approved
0.7471	Intermediate Similarity	NPD6959	Discontinued
0.7469	Intermediate Similarity	NPD2344	Approved
0.7455	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7768	Phase 2
0.7436	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3787	Discontinued
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7458	Discontinued
0.7382	Intermediate Similarity	NPD7435	Discontinued
0.7378	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3748	Approved
0.7338	Intermediate Similarity	NPD9269	Phase 2
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7308	Intermediate Similarity	NPD8313	Approved
0.7308	Intermediate Similarity	NPD8312	Approved
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.7296	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3226	Approved
0.7293	Intermediate Similarity	NPD7240	Approved
0.7292	Intermediate Similarity	NPD7698	Approved
0.7292	Intermediate Similarity	NPD7697	Approved
0.7292	Intermediate Similarity	NPD7696	Phase 3
0.7289	Intermediate Similarity	NPD2309	Approved
0.7288	Intermediate Similarity	NPD5242	Approved
0.7282	Intermediate Similarity	NPD8151	Discontinued
0.7268	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7266	Discontinued
0.7254	Intermediate Similarity	NPD7870	Phase 2
0.7254	Intermediate Similarity	NPD7871	Phase 2
0.7253	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7238	Intermediate Similarity	NPD5953	Discontinued
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7232	Intermediate Similarity	NPD5710	Approved
0.7232	Intermediate Similarity	NPD5711	Approved
0.7231	Intermediate Similarity	NPD7701	Phase 2
0.7225	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6651	Approved
0.7222	Intermediate Similarity	NPD7286	Phase 2
0.7189	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD7584	Approved
0.7157	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7874	Approved
0.7152	Intermediate Similarity	NPD2346	Discontinued
0.715	Intermediate Similarity	NPD5006	Approved
0.715	Intermediate Similarity	NPD5005	Approved
0.7134	Intermediate Similarity	NPD2799	Discontinued
0.7121	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.711	Intermediate Similarity	NPD6386	Approved
0.711	Intermediate Similarity	NPD6385	Approved
0.7101	Intermediate Similarity	NPD4357	Discontinued
0.7101	Intermediate Similarity	NPD7390	Discontinued
0.7089	Intermediate Similarity	NPD1203	Approved
0.7086	Intermediate Similarity	NPD5353	Approved
0.7081	Intermediate Similarity	NPD3764	Approved
0.7078	Intermediate Similarity	NPD9268	Approved
0.7066	Intermediate Similarity	NPD2654	Approved
0.7059	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7028	Phase 2
0.7035	Intermediate Similarity	NPD7783	Phase 2
0.7035	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4420	Approved
0.703	Intermediate Similarity	NPD7033	Discontinued
0.7005	Intermediate Similarity	NPD8150	Discontinued
0.7	Intermediate Similarity	NPD6213	Phase 3
0.7	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6212	Phase 3
0.6995	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6099	Approved
0.6988	Remote Similarity	NPD6100	Approved
0.6981	Remote Similarity	NPD1470	Approved
0.6979	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6844	Discontinued
0.6961	Remote Similarity	NPD2899	Discontinued
0.6957	Remote Similarity	NPD6832	Phase 2
0.6948	Remote Similarity	NPD5536	Phase 2
0.6944	Remote Similarity	NPD7229	Phase 3
0.6943	Remote Similarity	NPD3705	Approved
0.6943	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7680	Approved
0.6928	Remote Similarity	NPD4308	Phase 3
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1548	Phase 1
0.6903	Remote Similarity	NPD9545	Approved
0.6899	Remote Similarity	NPD9717	Approved
0.6894	Remote Similarity	NPD3018	Phase 2
0.6883	Remote Similarity	NPD9493	Approved
0.6882	Remote Similarity	NPD7549	Discontinued
0.6871	Remote Similarity	NPD3268	Approved
0.6868	Remote Similarity	NPD2403	Approved
0.686	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4908	Phase 1
0.6845	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4287	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data