NPASS Compound

Structure

NPC167595 OpenBabel07101718232D 24 27 0 0 0 0 0 0 0 0999 V2000 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 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 -3.5491 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 8 2 0 0 0 0 2 11 1 0 0 0 0 3 8 1 0 0 0 0 3 15 2 0 0 0 0 4 9 2 0 0 0 0 4 13 1 0 0 0 0 5 12 2 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 7 24 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 12 1 0 0 0 0 10 17 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.06
Volume:	308.802
LogP:	2.958
LogD:	2.823
LogS:	-4.019
# Rotatable Bonds:	2
TPSA:	98.36
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.746
Synthetic Accessibility Score:	2.573
Fsp3:	0.118
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:	-4.819
MDCK Permeability:	1.9879202227457426e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	95.74758911132812%
Volume Distribution (VD):	0.625
Pgp-substrate:	4.589910507202148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.478
CYP2C19-inhibitor:	0.927
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.748
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.858
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	12.493
Half-life (T1/2):	0.631

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.572
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.22
Maximum Recommended Daily Dose:	0.535
Skin Sensitization:	0.613
Carcinogencity:	0.555
Eye Corrosion:	0.007
Eye Irritation:	0.745
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC167595

Natural Product ID:	NPC167595
*Common Name:**	Khrinone D
IUPAC Name:	5,7-dihydroxy-3-(6-methoxy-1,3-benzodioxol-5-yl)chromen-4-one
Synonyms:	Khrinone D
Standard InCHIKey:	YCXPVHYOMBNKEI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H12O7/c1-21-12-5-14-13(23-7-24-14)4-9(12)10-6-22-15-3-8(18)2-11(19)16(15)17(10)20/h2-6,18-19H,7H2,1H3
SMILES:	COc1cc2c(cc1c1coc3cc(cc(c3c1=O)O)O)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079792
PubChem CID:	44613794
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
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO14114	Dalbergia parviflora	Species	Fabaceae	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
Others	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[565823]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	5.3	uM	PMID[565823]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.6	uM	PMID[565823]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.01	uM	PMID[565823]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	0.01	uM	PMID[565823]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	4.2	uM	PMID[565823]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	1.8	uM	PMID[565823]

☑ 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 NPC167595 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	448
0.1-0.2	1980
0.2-0.3	4587
0.3-0.4	10663
0.4-0.5	7348
0.5-0.6	3829
0.6-0.7	5352
0.7-0.8	4977
0.8-0.85	2118
0.85-0.9	1187
0.9-0.95	187
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC62518
0.9933	High Similarity	NPC215375
0.9803	High Similarity	NPC295009
0.9803	High Similarity	NPC260640
0.9737	High Similarity	NPC285973
0.9737	High Similarity	NPC225624
0.96	High Similarity	NPC35544
0.96	High Similarity	NPC153008
0.96	High Similarity	NPC104728
0.96	High Similarity	NPC148497
0.9536	High Similarity	NPC57211
0.9536	High Similarity	NPC478213
0.9533	High Similarity	NPC279061
0.9484	High Similarity	NPC469575
0.9474	High Similarity	NPC478238
0.947	High Similarity	NPC52623
0.9467	High Similarity	NPC239363
0.9467	High Similarity	NPC156953
0.9404	High Similarity	NPC19980
0.9404	High Similarity	NPC262623
0.9404	High Similarity	NPC45291
0.9342	High Similarity	NPC181209
0.9342	High Similarity	NPC291802
0.9342	High Similarity	NPC269451
0.9342	High Similarity	NPC216769
0.9342	High Similarity	NPC209487
0.9342	High Similarity	NPC121522
0.9342	High Similarity	NPC100263
0.9342	High Similarity	NPC131266
0.9342	High Similarity	NPC35763
0.9342	High Similarity	NPC245382
0.9342	High Similarity	NPC100971
0.9338	High Similarity	NPC234152
0.9299	High Similarity	NPC470178
0.9295	High Similarity	NPC162668
0.9281	High Similarity	NPC280937
0.9281	High Similarity	NPC124714
0.9281	High Similarity	NPC250557
0.9276	High Similarity	NPC288316
0.9231	High Similarity	NPC269906
0.9226	High Similarity	NPC474990
0.9221	High Similarity	NPC39184
0.9221	High Similarity	NPC130589
0.9221	High Similarity	NPC134287
0.9221	High Similarity	NPC18954
0.9216	High Similarity	NPC292460
0.9211	High Similarity	NPC10467
0.92	High Similarity	NPC12377
0.9193	High Similarity	NPC475825
0.9193	High Similarity	NPC223375
0.9172	High Similarity	NPC94155
0.9156	High Similarity	NPC244371
0.9145	High Similarity	NPC200060
0.9145	High Similarity	NPC139293
0.9145	High Similarity	NPC142876
0.9145	High Similarity	NPC333691
0.9145	High Similarity	NPC264550
0.9145	High Similarity	NPC69430
0.9145	High Similarity	NPC40290
0.9145	High Similarity	NPC264289
0.9145	High Similarity	NPC195763
0.9139	High Similarity	NPC93034
0.9139	High Similarity	NPC119660
0.9133	High Similarity	NPC224687
0.913	High Similarity	NPC105511
0.913	High Similarity	NPC224462
0.9125	High Similarity	NPC76482
0.9125	High Similarity	NPC42892
0.9114	High Similarity	NPC81679
0.9103	High Similarity	NPC258644
0.9103	High Similarity	NPC78103
0.9091	High Similarity	NPC68882
0.9085	High Similarity	NPC306821
0.9085	High Similarity	NPC179183
0.9079	High Similarity	NPC139364
0.9079	High Similarity	NPC254702
0.9079	High Similarity	NPC287395
0.9079	High Similarity	NPC203747
0.9079	High Similarity	NPC183655
0.9079	High Similarity	NPC218490
0.9079	High Similarity	NPC194653
0.9079	High Similarity	NPC80710
0.9074	High Similarity	NPC205076
0.9074	High Similarity	NPC307518
0.9074	High Similarity	NPC48773
0.9073	High Similarity	NPC120924
0.9073	High Similarity	NPC195919
0.9073	High Similarity	NPC216314
0.9073	High Similarity	NPC88345
0.9068	High Similarity	NPC471287
0.9068	High Similarity	NPC211309
0.9067	High Similarity	NPC182842
0.9062	High Similarity	NPC113093
0.9057	High Similarity	NPC110257
0.9051	High Similarity	NPC470756
0.9038	High Similarity	NPC45131
0.9032	High Similarity	NPC471981
0.9032	High Similarity	NPC472915
0.9026	High Similarity	NPC117579
0.9026	High Similarity	NPC226973
0.9026	High Similarity	NPC149614
0.9026	High Similarity	NPC308451
0.9026	High Similarity	NPC208043
0.9024	High Similarity	NPC257714
0.902	High Similarity	NPC102003
0.902	High Similarity	NPC328119
0.902	High Similarity	NPC92722
0.9013	High Similarity	NPC188074
0.9013	High Similarity	NPC125449
0.9012	High Similarity	NPC212748
0.9012	High Similarity	NPC44558
0.9007	High Similarity	NPC296575
0.9006	High Similarity	NPC471288
0.9006	High Similarity	NPC135345
0.8994	High Similarity	NPC273021
0.8994	High Similarity	NPC18284
0.8994	High Similarity	NPC478199
0.8994	High Similarity	NPC125991
0.8981	High Similarity	NPC181960
0.8981	High Similarity	NPC99597
0.8981	High Similarity	NPC210084
0.8981	High Similarity	NPC476981
0.8974	High Similarity	NPC208197
0.8974	High Similarity	NPC256612
0.8974	High Similarity	NPC2928
0.8974	High Similarity	NPC472909
0.8974	High Similarity	NPC213622
0.8974	High Similarity	NPC20830
0.8974	High Similarity	NPC37392
0.8968	High Similarity	NPC188203
0.8968	High Similarity	NPC239128
0.8968	High Similarity	NPC187498
0.8968	High Similarity	NPC241498
0.8968	High Similarity	NPC71334
0.8968	High Similarity	NPC301123
0.8968	High Similarity	NPC156222
0.8968	High Similarity	NPC101996
0.8968	High Similarity	NPC83508
0.8968	High Similarity	NPC275836
0.8968	High Similarity	NPC100887
0.8968	High Similarity	NPC222830
0.8968	High Similarity	NPC301323
0.8968	High Similarity	NPC212678
0.8968	High Similarity	NPC275722
0.8968	High Similarity	NPC120163
0.8968	High Similarity	NPC162313
0.8968	High Similarity	NPC57030
0.8968	High Similarity	NPC25270
0.8968	High Similarity	NPC293183
0.8968	High Similarity	NPC256283
0.8968	High Similarity	NPC131624
0.8968	High Similarity	NPC198826
0.8963	High Similarity	NPC472607
0.8963	High Similarity	NPC290304
0.8963	High Similarity	NPC236327
0.8957	High Similarity	NPC235575
0.8954	High Similarity	NPC131451
0.8954	High Similarity	NPC15329
0.8951	High Similarity	NPC475942
0.8951	High Similarity	NPC472383
0.8951	High Similarity	NPC183036
0.8951	High Similarity	NPC472381
0.8951	High Similarity	NPC469931
0.8951	High Similarity	NPC45638
0.8951	High Similarity	NPC58053
0.8951	High Similarity	NPC226294
0.8951	High Similarity	NPC105025
0.8951	High Similarity	NPC186807
0.8951	High Similarity	NPC93337
0.8951	High Similarity	NPC201292
0.8947	High Similarity	NPC143903
0.8947	High Similarity	NPC226987
0.8938	High Similarity	NPC94777
0.8931	High Similarity	NPC471290
0.8924	High Similarity	NPC238405
0.8924	High Similarity	NPC196879
0.8924	High Similarity	NPC257914
0.8924	High Similarity	NPC104459
0.8917	High Similarity	NPC235165
0.8917	High Similarity	NPC472916
0.8917	High Similarity	NPC255106
0.891	High Similarity	NPC75279
0.891	High Similarity	NPC167091
0.891	High Similarity	NPC292214
0.891	High Similarity	NPC176775
0.891	High Similarity	NPC279930
0.891	High Similarity	NPC160951
0.891	High Similarity	NPC145379
0.891	High Similarity	NPC255350
0.891	High Similarity	NPC271779
0.891	High Similarity	NPC69394
0.891	High Similarity	NPC22519
0.891	High Similarity	NPC274327
0.891	High Similarity	NPC183878
0.891	High Similarity	NPC86485
0.891	High Similarity	NPC47781
0.891	High Similarity	NPC276409
0.891	High Similarity	NPC231018
0.891	High Similarity	NPC250822
0.891	High Similarity	NPC206238

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 NPC167595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	414
0.1-0.2	977
0.2-0.3	1998
0.3-0.4	2679
0.4-0.5	1759
0.5-0.6	863
0.6-0.7	305
0.7-0.8	111
0.8-0.85	30
0.85-0.9	12
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9125	High Similarity	NPD3818	Discontinued
0.891	High Similarity	NPD2801	Approved
0.8726	High Similarity	NPD1934	Approved
0.8679	High Similarity	NPD3882	Suspended
0.8623	High Similarity	NPD4338	Clinical (unspecified phase)
0.8606	High Similarity	NPD7054	Approved
0.8554	High Similarity	NPD7074	Phase 3
0.8554	High Similarity	NPD7472	Approved
0.8533	High Similarity	NPD1510	Phase 2
0.8526	High Similarity	NPD6980	Clinical (unspecified phase)
0.8519	High Similarity	NPD5494	Approved
0.8509	High Similarity	NPD4381	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD1511	Approved
0.8438	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD7808	Phase 3
0.8393	Intermediate Similarity	NPD6797	Phase 2
0.8385	Intermediate Similarity	NPD3817	Phase 2
0.8344	Intermediate Similarity	NPD1512	Approved
0.8343	Intermediate Similarity	NPD7251	Discontinued
0.8303	Intermediate Similarity	NPD6232	Discontinued
0.8267	Intermediate Similarity	NPD1240	Approved
0.8263	Intermediate Similarity	NPD7473	Discontinued
0.825	Intermediate Similarity	NPD4380	Phase 2
0.8242	Intermediate Similarity	NPD1247	Approved
0.8221	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6166	Phase 2
0.8204	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1607	Approved
0.8148	Intermediate Similarity	NPD37	Approved
0.8141	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6559	Discontinued
0.8129	Intermediate Similarity	NPD1549	Phase 2
0.8101	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD943	Approved
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD4967	Phase 2
0.8	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD4966	Approved
0.8	Intermediate Similarity	NPD4965	Approved
0.7953	Intermediate Similarity	NPD5844	Phase 1
0.7952	Intermediate Similarity	NPD7075	Discontinued
0.7939	Intermediate Similarity	NPD5402	Approved
0.7937	Intermediate Similarity	NPD2532	Approved
0.7937	Intermediate Similarity	NPD2533	Approved
0.7937	Intermediate Similarity	NPD2534	Approved
0.7879	Intermediate Similarity	NPD7819	Suspended
0.7879	Intermediate Similarity	NPD1465	Phase 2
0.7879	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6799	Approved
0.7857	Intermediate Similarity	NPD230	Phase 1
0.7826	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3926	Phase 2
0.7818	Intermediate Similarity	NPD6801	Discontinued
0.7811	Intermediate Similarity	NPD7199	Phase 2
0.7809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7411	Suspended
0.774	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3749	Approved
0.7736	Intermediate Similarity	NPD2800	Approved
0.773	Intermediate Similarity	NPD920	Approved
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6599	Discontinued
0.7688	Intermediate Similarity	NPD3750	Approved
0.7688	Intermediate Similarity	NPD7228	Approved
0.7683	Intermediate Similarity	NPD1653	Approved
0.7628	Intermediate Similarity	NPD1933	Approved
0.7628	Intermediate Similarity	NPD447	Suspended
0.7625	Intermediate Similarity	NPD1243	Approved
0.7619	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7685	Pre-registration
0.7607	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6959	Discontinued
0.7595	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3751	Discontinued
0.7547	Intermediate Similarity	NPD1551	Phase 2
0.7516	Intermediate Similarity	NPD2798	Approved
0.7515	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD5401	Approved
0.7485	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3027	Phase 3
0.7471	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7768	Phase 2
0.7468	Intermediate Similarity	NPD9494	Approved
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.7425	Intermediate Similarity	NPD7458	Discontinued
0.7407	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3748	Approved
0.7358	Intermediate Similarity	NPD6651	Approved
0.7356	Intermediate Similarity	NPD5711	Approved
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7356	Intermediate Similarity	NPD5710	Approved
0.7355	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1613	Approved
0.7342	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7325	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3226	Approved
0.7318	Intermediate Similarity	NPD7240	Approved
0.7317	Intermediate Similarity	NPD2309	Approved
0.7317	Intermediate Similarity	NPD6190	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7316	Intermediate Similarity	NPD7696	Phase 3
0.7316	Intermediate Similarity	NPD7697	Approved
0.7316	Intermediate Similarity	NPD7698	Approved
0.7314	Intermediate Similarity	NPD5242	Approved
0.7308	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD8151	Discontinued
0.7278	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7871	Phase 2
0.7277	Intermediate Similarity	NPD7870	Phase 2
0.7263	Intermediate Similarity	NPD5953	Discontinued
0.7256	Intermediate Similarity	NPD4628	Phase 3
0.7255	Intermediate Similarity	NPD9269	Phase 2
0.7249	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7286	Phase 2
0.7238	Intermediate Similarity	NPD8313	Approved
0.7238	Intermediate Similarity	NPD8312	Approved
0.7229	Intermediate Similarity	NPD7390	Discontinued
0.7219	Intermediate Similarity	NPD9268	Approved
0.7209	Intermediate Similarity	NPD5353	Approved
0.7208	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2654	Approved
0.7178	Intermediate Similarity	NPD2346	Discontinued
0.7173	Intermediate Similarity	NPD5006	Approved
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.7173	Intermediate Similarity	NPD5005	Approved
0.7166	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD6535	Approved
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.716	Intermediate Similarity	NPD2799	Discontinued
0.7135	Intermediate Similarity	NPD6386	Approved
0.7135	Intermediate Similarity	NPD6385	Approved
0.7126	Intermediate Similarity	NPD4357	Discontinued
0.712	Intermediate Similarity	NPD8434	Phase 2
0.7117	Intermediate Similarity	NPD6100	Approved
0.7117	Intermediate Similarity	NPD6099	Approved
0.7115	Intermediate Similarity	NPD1203	Approved
0.7113	Intermediate Similarity	NPD7584	Approved
0.7107	Intermediate Similarity	NPD3764	Approved
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3705	Approved
0.7076	Intermediate Similarity	NPD7028	Phase 2
0.7073	Intermediate Similarity	NPD7266	Discontinued
0.7056	Intermediate Similarity	NPD7801	Approved
0.7055	Intermediate Similarity	NPD7033	Discontinued
0.7053	Intermediate Similarity	NPD4420	Approved
0.7053	Intermediate Similarity	NPD7700	Phase 2
0.7053	Intermediate Similarity	NPD7699	Phase 2
0.7048	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1470	Approved
0.6994	Remote Similarity	NPD6844	Discontinued
0.6983	Remote Similarity	NPD2403	Approved
0.6982	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6832	Phase 2
0.6974	Remote Similarity	NPD5536	Phase 2
0.697	Remote Similarity	NPD7783	Phase 2
0.697	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7229	Phase 3
0.6951	Remote Similarity	NPD4308	Phase 3
0.6935	Remote Similarity	NPD8150	Discontinued
0.6931	Remote Similarity	NPD6212	Phase 3
0.6931	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6213	Phase 3
0.6928	Remote Similarity	NPD9545	Approved
0.6928	Remote Similarity	NPD1548	Phase 1
0.6927	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9717	Approved
0.6918	Remote Similarity	NPD3018	Phase 2
0.6911	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD9493	Approved
0.6902	Remote Similarity	NPD7549	Discontinued
0.6894	Remote Similarity	NPD3268	Approved
0.6882	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4908	Phase 1
0.6867	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD4287	Approved
0.6859	Remote Similarity	NPD4361	Phase 2
0.6859	Remote Similarity	NPD4362	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