NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.05
Volume:	259.317
LogP:	2.234
LogD:	2.397
LogS:	-3.449
# Rotatable Bonds:	1
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.587
Synthetic Accessibility Score:	2.368
Fsp3:	0.071
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:	-4.968
MDCK Permeability:	7.831803486624267e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.925
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	91.81873321533203%
Volume Distribution (VD):	0.783
Pgp-substrate:	12.271886825561523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.514
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.613
CYP2D6-substrate:	0.654
CYP3A4-inhibitor:	0.397
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	7.873
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.537
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.929
Carcinogencity:	0.028
Eye Corrosion:	0.09
Eye Irritation:	0.95
Respiratory Toxicity:	0.256

Download Data

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

Natural Product: NPC101996

Natural Product ID:	NPC101996
*Common Name:**	Alloathyriol
IUPAC Name:	1,3,6-trihydroxy-7-methoxyxanthen-9-one
Synonyms:	Alloathyriol
Standard InCHIKey:	CLZONBOPXUGYNY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O6/c1-19-11-4-7-10(5-8(11)16)20-12-3-6(15)2-9(17)13(12)14(7)18/h2-5,15-17H,1H3
SMILES:	COc1cc2c(cc1O)oc1c(c2=O)c(O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482243
PubChem CID:	44575387
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14600386]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[15787435]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	roots	n.a.	n.a.	PMID[16989524]
NPO32808	cratoxylum formosum ssp. pruniflorum	Species	Hypericaceae	Eukaryota	stems	n.a.	n.a.	PMID[20608716]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22863942]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[24042007]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	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
IC50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	117000.0	nM	PMID[469007]
NPT34	Cell Line	BV-2	Mus musculus	IC50	>	100000.0	nM	PMID[469009]
NPT34	Cell Line	BV-2	Mus musculus	Inhibition	>	80.0	%	PMID[469009]

☑ 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 NPC101996 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	519
0.1-0.2	2140
0.2-0.3	5376
0.3-0.4	11806
0.4-0.5	5153
0.5-0.6	4075
0.6-0.7	5035
0.7-0.8	4767
0.8-0.85	1969
0.85-0.9	1034
0.9-0.95	560
0.95-1	263

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC206238
0.9932	High Similarity	NPC292214
0.9932	High Similarity	NPC88645
0.9932	High Similarity	NPC167091
0.9932	High Similarity	NPC271779
0.9931	High Similarity	NPC171010
0.9863	High Similarity	NPC199100
0.9863	High Similarity	NPC161277
0.9863	High Similarity	NPC39007
0.9863	High Similarity	NPC120537
0.9863	High Similarity	NPC180234
0.9862	High Similarity	NPC179183
0.9795	High Similarity	NPC149614
0.9795	High Similarity	NPC251110
0.9732	High Similarity	NPC262286
0.9732	High Similarity	NPC99597
0.9732	High Similarity	NPC210084
0.9732	High Similarity	NPC36852
0.973	High Similarity	NPC2928
0.9726	High Similarity	NPC29231
0.9726	High Similarity	NPC62042
0.9726	High Similarity	NPC248102
0.9726	High Similarity	NPC61620
0.9724	High Similarity	NPC194856
0.9664	High Similarity	NPC472916
0.9664	High Similarity	NPC255106
0.9664	High Similarity	NPC138243
0.9664	High Similarity	NPC235165
0.966	High Similarity	NPC117579
0.9658	High Similarity	NPC200221
0.9658	High Similarity	NPC294502
0.9655	High Similarity	NPC207729
0.96	High Similarity	NPC472911
0.96	High Similarity	NPC48208
0.96	High Similarity	NPC245758
0.96	High Similarity	NPC156057
0.96	High Similarity	NPC469584
0.96	High Similarity	NPC300727
0.96	High Similarity	NPC78225
0.96	High Similarity	NPC472914
0.96	High Similarity	NPC475267
0.96	High Similarity	NPC472910
0.96	High Similarity	NPC162869
0.96	High Similarity	NPC472913
0.96	High Similarity	NPC474208
0.96	High Similarity	NPC474836
0.96	High Similarity	NPC222814
0.96	High Similarity	NPC241904
0.96	High Similarity	NPC96167
0.9597	High Similarity	NPC256612
0.9597	High Similarity	NPC20830
0.9597	High Similarity	NPC113906
0.9597	High Similarity	NPC208197
0.9595	High Similarity	NPC162313
0.9595	High Similarity	NPC241498
0.9595	High Similarity	NPC198826
0.9595	High Similarity	NPC275722
0.9595	High Similarity	NPC301323
0.9595	High Similarity	NPC100887
0.9595	High Similarity	NPC57030
0.9595	High Similarity	NPC212678
0.9595	High Similarity	NPC222830
0.9595	High Similarity	NPC239128
0.9595	High Similarity	NPC131624
0.9595	High Similarity	NPC293183
0.9595	High Similarity	NPC25270
0.9595	High Similarity	NPC187498
0.9595	High Similarity	NPC83508
0.9595	High Similarity	NPC156222
0.9595	High Similarity	NPC275836
0.9595	High Similarity	NPC188203
0.9595	High Similarity	NPC71334
0.9595	High Similarity	NPC120163
0.9595	High Similarity	NPC256283
0.9592	High Similarity	NPC45873
0.9589	High Similarity	NPC43669
0.9589	High Similarity	NPC287395
0.9589	High Similarity	NPC183655
0.9589	High Similarity	NPC276930
0.9589	High Similarity	NPC196277
0.9589	High Similarity	NPC272721
0.9539	High Similarity	NPC308992
0.9536	High Similarity	NPC476242
0.9533	High Similarity	NPC274730
0.9533	High Similarity	NPC191146
0.9533	High Similarity	NPC68093
0.953	High Similarity	NPC176775
0.953	High Similarity	NPC274327
0.953	High Similarity	NPC276409
0.953	High Similarity	NPC145379
0.953	High Similarity	NPC69394
0.953	High Similarity	NPC231018
0.953	High Similarity	NPC255350
0.953	High Similarity	NPC75279
0.953	High Similarity	NPC183878
0.953	High Similarity	NPC47781
0.953	High Similarity	NPC280937
0.953	High Similarity	NPC22519
0.953	High Similarity	NPC160951
0.953	High Similarity	NPC472915
0.953	High Similarity	NPC250822
0.9527	High Similarity	NPC202157
0.9527	High Similarity	NPC31363
0.9527	High Similarity	NPC45291
0.9527	High Similarity	NPC19980
0.9527	High Similarity	NPC204515
0.9524	High Similarity	NPC296197
0.9524	High Similarity	NPC259713
0.9524	High Similarity	NPC17286
0.9524	High Similarity	NPC216318
0.9521	High Similarity	NPC77378
0.9521	High Similarity	NPC30647
0.9521	High Similarity	NPC61871
0.9521	High Similarity	NPC46941
0.9521	High Similarity	NPC55557
0.9477	High Similarity	NPC83922
0.9477	High Similarity	NPC472448
0.9474	High Similarity	NPC263449
0.9474	High Similarity	NPC228785
0.9474	High Similarity	NPC14353
0.9474	High Similarity	NPC56085
0.9474	High Similarity	NPC476980
0.947	High Similarity	NPC223787
0.947	High Similarity	NPC299520
0.947	High Similarity	NPC129684
0.947	High Similarity	NPC181960
0.9467	High Similarity	NPC2476
0.9467	High Similarity	NPC201451
0.9467	High Similarity	NPC213622
0.9467	High Similarity	NPC37392
0.9467	High Similarity	NPC4455
0.9467	High Similarity	NPC146165
0.9467	High Similarity	NPC138360
0.9467	High Similarity	NPC280339
0.9467	High Similarity	NPC92659
0.9467	High Similarity	NPC152951
0.9467	High Similarity	NPC168247
0.9467	High Similarity	NPC183597
0.9467	High Similarity	NPC57674
0.9467	High Similarity	NPC128863
0.9467	High Similarity	NPC44079
0.9467	High Similarity	NPC167815
0.9467	High Similarity	NPC26227
0.9467	High Similarity	NPC163780
0.9467	High Similarity	NPC117992
0.9467	High Similarity	NPC50715
0.9467	High Similarity	NPC230149
0.9467	High Similarity	NPC196439
0.9467	High Similarity	NPC227325
0.9467	High Similarity	NPC472909
0.9467	High Similarity	NPC201136
0.9463	High Similarity	NPC245382
0.9463	High Similarity	NPC100971
0.9463	High Similarity	NPC100263
0.9463	High Similarity	NPC142540
0.9463	High Similarity	NPC219582
0.9463	High Similarity	NPC209487
0.9463	High Similarity	NPC291802
0.9463	High Similarity	NPC39732
0.9463	High Similarity	NPC121522
0.9463	High Similarity	NPC216769
0.9463	High Similarity	NPC236637
0.9463	High Similarity	NPC60972
0.9463	High Similarity	NPC477231
0.9463	High Similarity	NPC269451
0.9463	High Similarity	NPC257648
0.9463	High Similarity	NPC35763
0.9463	High Similarity	NPC302950
0.9463	High Similarity	NPC131266
0.9463	High Similarity	NPC181209
0.9459	High Similarity	NPC151473
0.9459	High Similarity	NPC184136
0.9459	High Similarity	NPC306821
0.9456	High Similarity	NPC120464
0.9456	High Similarity	NPC12367
0.9456	High Similarity	NPC118726
0.9452	High Similarity	NPC231013
0.9452	High Similarity	NPC209278
0.9412	High Similarity	NPC258331
0.9412	High Similarity	NPC278052
0.9412	High Similarity	NPC266314
0.9412	High Similarity	NPC162668
0.9412	High Similarity	NPC40491
0.9412	High Similarity	NPC61010
0.9412	High Similarity	NPC167678
0.9412	High Similarity	NPC29876
0.9408	High Similarity	NPC152904
0.9408	High Similarity	NPC196879
0.9408	High Similarity	NPC250214
0.9408	High Similarity	NPC95936
0.9408	High Similarity	NPC16935
0.9408	High Similarity	NPC100123
0.9408	High Similarity	NPC55738
0.9404	High Similarity	NPC474638
0.9404	High Similarity	NPC49824
0.9404	High Similarity	NPC266960
0.9404	High Similarity	NPC247017
0.9404	High Similarity	NPC474520
0.9404	High Similarity	NPC245546
0.9404	High Similarity	NPC201837

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 NPC101996 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	476
0.1-0.2	1028
0.2-0.3	1987
0.3-0.4	2675
0.4-0.5	1611
0.5-0.6	914
0.6-0.7	317
0.7-0.8	93
0.8-0.85	32
0.85-0.9	10
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.953	High Similarity	NPD2801	Approved
0.9463	High Similarity	NPD1934	Approved
0.9184	High Similarity	NPD1511	Approved
0.9145	High Similarity	NPD2393	Clinical (unspecified phase)
0.906	High Similarity	NPD1512	Approved
0.9026	High Similarity	NPD3882	Suspended
0.8868	High Similarity	NPD6168	Clinical (unspecified phase)
0.8868	High Similarity	NPD6167	Clinical (unspecified phase)
0.8868	High Similarity	NPD6166	Phase 2
0.8782	High Similarity	NPD4868	Clinical (unspecified phase)
0.8758	High Similarity	NPD3818	Discontinued
0.8734	High Similarity	NPD5494	Approved
0.8716	High Similarity	NPD1549	Phase 2
0.8654	High Similarity	NPD1465	Phase 2
0.865	High Similarity	NPD7074	Phase 3
0.8649	High Similarity	NPD1550	Clinical (unspecified phase)
0.8649	High Similarity	NPD1552	Clinical (unspecified phase)
0.8606	High Similarity	NPD4338	Clinical (unspecified phase)
0.8599	High Similarity	NPD3817	Phase 2
0.8589	High Similarity	NPD7054	Approved
0.8537	High Similarity	NPD7472	Approved
0.8514	High Similarity	NPD1510	Phase 2
0.8497	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD943	Approved
0.8493	Intermediate Similarity	NPD1240	Approved
0.8462	Intermediate Similarity	NPD4380	Phase 2
0.8378	Intermediate Similarity	NPD1607	Approved
0.8375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD7075	Discontinued
0.8373	Intermediate Similarity	NPD6797	Phase 2
0.8333	Intermediate Similarity	NPD1247	Approved
0.8323	Intermediate Similarity	NPD7251	Discontinued
0.8302	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6232	Discontinued
0.8276	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7808	Phase 3
0.8263	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8242	Intermediate Similarity	NPD7473	Discontinued
0.8219	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2796	Approved
0.8194	Intermediate Similarity	NPD6799	Approved
0.8188	Intermediate Similarity	NPD230	Phase 1
0.8187	Intermediate Similarity	NPD7819	Suspended
0.8141	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5402	Approved
0.8121	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1613	Approved
0.8105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD447	Suspended
0.8063	Intermediate Similarity	NPD7411	Suspended
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7988	Intermediate Similarity	NPD919	Approved
0.7974	Intermediate Similarity	NPD2935	Discontinued
0.7935	Intermediate Similarity	NPD2800	Approved
0.7929	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3749	Approved
0.7908	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6559	Discontinued
0.7885	Intermediate Similarity	NPD3750	Approved
0.7857	Intermediate Similarity	NPD1551	Phase 2
0.7812	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD9494	Approved
0.7764	Intermediate Similarity	NPD1653	Approved
0.7751	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1933	Approved
0.7707	Intermediate Similarity	NPD1243	Approved
0.7702	Intermediate Similarity	NPD920	Approved
0.7702	Intermediate Similarity	NPD5403	Approved
0.7692	Intermediate Similarity	NPD2344	Approved
0.7688	Intermediate Similarity	NPD2534	Approved
0.7688	Intermediate Similarity	NPD5401	Approved
0.7688	Intermediate Similarity	NPD2532	Approved
0.7688	Intermediate Similarity	NPD2533	Approved
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3027	Phase 3
0.7661	Intermediate Similarity	NPD3751	Discontinued
0.7651	Intermediate Similarity	NPD7768	Phase 2
0.7628	Intermediate Similarity	NPD6099	Approved
0.7628	Intermediate Similarity	NPD6100	Approved
0.7607	Intermediate Similarity	NPD3226	Approved
0.7596	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD9269	Phase 2
0.7564	Intermediate Similarity	NPD3748	Approved
0.756	Intermediate Similarity	NPD6234	Discontinued
0.7547	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7533	Intermediate Similarity	NPD1203	Approved
0.7517	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7453	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2799	Discontinued
0.7438	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6651	Approved
0.7429	Intermediate Similarity	NPD5953	Discontinued
0.7427	Intermediate Similarity	NPD3787	Discontinued
0.7414	Intermediate Similarity	NPD7286	Phase 2
0.7384	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1610	Phase 2
0.7365	Intermediate Similarity	NPD37	Approved
0.7356	Intermediate Similarity	NPD7228	Approved
0.7337	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4967	Phase 2
0.7337	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD9717	Approved
0.7301	Intermediate Similarity	NPD7390	Discontinued
0.7297	Intermediate Similarity	NPD9268	Approved
0.7288	Intermediate Similarity	NPD7685	Pre-registration
0.7283	Intermediate Similarity	NPD5242	Approved
0.7278	Intermediate Similarity	NPD5353	Approved
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7262	Intermediate Similarity	NPD6844	Discontinued
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1548	Phase 1
0.7225	Intermediate Similarity	NPD5710	Approved
0.7225	Intermediate Similarity	NPD5711	Approved
0.7219	Intermediate Similarity	NPD1608	Approved
0.7219	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6776	Approved
0.7219	Intermediate Similarity	NPD6778	Approved
0.7219	Intermediate Similarity	NPD6779	Approved
0.7219	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD6782	Approved
0.7207	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD8312	Approved
0.719	Intermediate Similarity	NPD1470	Approved
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD411	Approved
0.7161	Intermediate Similarity	NPD6832	Phase 2
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD2798	Approved
0.7125	Intermediate Similarity	NPD4308	Phase 3
0.7121	Intermediate Similarity	NPD2899	Discontinued
0.7105	Intermediate Similarity	NPD7435	Discontinued
0.7101	Intermediate Similarity	NPD6386	Approved
0.7101	Intermediate Similarity	NPD6385	Approved
0.7098	Intermediate Similarity	NPD8151	Discontinued
0.7097	Intermediate Similarity	NPD2861	Phase 2
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7088	Intermediate Similarity	NPD8150	Discontinued
0.707	Intermediate Similarity	NPD3268	Approved
0.7059	Intermediate Similarity	NPD4749	Approved
0.7059	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7549	Discontinued
0.7055	Intermediate Similarity	NPD2654	Approved
0.7048	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5536	Phase 2
0.7043	Intermediate Similarity	NPD4360	Phase 2
0.7043	Intermediate Similarity	NPD4363	Phase 3
0.7039	Intermediate Similarity	NPD1201	Approved
0.7037	Intermediate Similarity	NPD1471	Phase 3
0.7025	Intermediate Similarity	NPD6233	Phase 2
0.702	Intermediate Similarity	NPD17	Approved
0.7019	Intermediate Similarity	NPD7033	Discontinued
0.7016	Intermediate Similarity	NPD7696	Phase 3
0.7016	Intermediate Similarity	NPD7697	Approved
0.7016	Intermediate Similarity	NPD7698	Approved
0.7011	Intermediate Similarity	NPD4287	Approved
0.7006	Intermediate Similarity	NPD4625	Phase 3
0.7	Intermediate Similarity	NPD9545	Approved
0.7	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7584	Approved
0.6993	Remote Similarity	NPD1481	Phase 2
0.6987	Remote Similarity	NPD3018	Phase 2
0.6986	Remote Similarity	NPD228	Approved
0.698	Remote Similarity	NPD9493	Approved
0.6979	Remote Similarity	NPD7871	Phase 2
0.6979	Remote Similarity	NPD7870	Phase 2
0.6977	Remote Similarity	NPD4288	Approved
0.6977	Remote Similarity	NPD2296	Approved
0.697	Remote Similarity	NPD2354	Approved
0.6968	Remote Similarity	NPD2797	Approved
0.6963	Remote Similarity	NPD6823	Phase 2
0.6962	Remote Similarity	NPD3764	Approved
0.6962	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD7701	Phase 2
0.6952	Remote Similarity	NPD6534	Approved
0.6952	Remote Similarity	NPD6535	Approved
0.6951	Remote Similarity	NPD1652	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