NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.03
Volume:	242.021
LogP:	1.51
LogD:	1.026
LogS:	-3.587
# Rotatable Bonds:	0
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	2.527
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.27
MDCK Permeability:	9.495588528807275e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.123
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	93.89917755126953%
Volume Distribution (VD):	0.634
Pgp-substrate:	12.716581344604492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.151
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.435
CYP2C9-substrate:	0.367
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	8.863
Half-life (T1/2):	0.923

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.352
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.806
Rat Oral Acute Toxicity:	0.268
Maximum Recommended Daily Dose:	0.317
Skin Sensitization:	0.942
Carcinogencity:	0.711
Eye Corrosion:	0.009
Eye Irritation:	0.912
Respiratory Toxicity:	0.109

Download Data

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

Natural Product: NPC77378

Natural Product ID:	NPC77378
*Common Name:**
IUPAC Name:	3,4,5,6-tetrahydroxyxanthen-9-one
Synonyms:	3,4,5,6-Tetrahydroxyxanthone
Standard InCHIKey:	MUWSBAZQOGXKJK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O6/c14-7-3-1-5-9(16)6-2-4-8(15)11(18)13(6)19-12(5)10(7)17/h1-4,14-15,17-18H
SMILES:	Oc1ccc2c(c1O)oc1c(c2=O)ccc(c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477921
PubChem CID:	10015450
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
NPO25854	Tripterospermum lanceolatum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517742]
NPO25854	Tripterospermum lanceolatum	Species	Gentianaceae	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	5
Ki	1
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	5
Protein Complex	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	IC50	=	238500.0	nM	PMID[458528]
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	Inhibition	=	34.28	%	PMID[458528]
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	Inhibition	=	46.17	%	PMID[458528]
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	Inhibition	=	55.47	%	PMID[458528]
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	Ki	=	126000.0	nM	PMID[458528]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	18500.0	nM	PMID[458530]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	5000.0	nM	PMID[458529]
NPT21990	SINGLE PROTEIN	7,8-dihydro-8-oxoguanine triphosphatase	Homo sapiens	IC50	=	57000.0	nM	PMID[458531]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	5000	nM	PMID[23252603]

☑ 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 NPC77378 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	561
0.1-0.2	2369
0.2-0.3	6282
0.3-0.4	11587
0.4-0.5	4391
0.5-0.6	4464
0.6-0.7	5122
0.7-0.8	4622
0.8-0.85	1821
0.85-0.9	946
0.9-0.95	411
0.95-1	121

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC272721
0.9929	High Similarity	NPC43669
0.9929	High Similarity	NPC196277
0.979	High Similarity	NPC29231
0.979	High Similarity	NPC248102
0.9722	High Similarity	NPC251110
0.9718	High Similarity	NPC168803
0.9655	High Similarity	NPC39007
0.9655	High Similarity	NPC161277
0.9653	High Similarity	NPC61620
0.9645	High Similarity	NPC59551
0.9589	High Similarity	NPC70433
0.9589	High Similarity	NPC167091
0.9589	High Similarity	NPC273462
0.9589	High Similarity	NPC33051
0.9589	High Similarity	NPC227337
0.9589	High Similarity	NPC292214
0.9589	High Similarity	NPC88645
0.9589	High Similarity	NPC49402
0.9589	High Similarity	NPC271779
0.9589	High Similarity	NPC206238
0.9586	High Similarity	NPC171010
0.9586	High Similarity	NPC31363
0.958	High Similarity	NPC207729
0.9524	High Similarity	NPC57674
0.9524	High Similarity	NPC200246
0.9524	High Similarity	NPC230149
0.9524	High Similarity	NPC168247
0.9524	High Similarity	NPC152951
0.9524	High Similarity	NPC117992
0.9524	High Similarity	NPC256925
0.9521	High Similarity	NPC257648
0.9521	High Similarity	NPC180234
0.9521	High Similarity	NPC101996
0.9521	High Similarity	NPC199100
0.9521	High Similarity	NPC477231
0.9521	High Similarity	NPC120537
0.9517	High Similarity	NPC45873
0.9517	High Similarity	NPC151473
0.9514	High Similarity	NPC276930
0.9514	High Similarity	NPC194856
0.951	High Similarity	NPC209278
0.9459	High Similarity	NPC133970
0.9459	High Similarity	NPC6633
0.9459	High Similarity	NPC470600
0.9459	High Similarity	NPC5322
0.9459	High Similarity	NPC474638
0.9459	High Similarity	NPC115853
0.9456	High Similarity	NPC469550
0.9452	High Similarity	NPC149614
0.9448	High Similarity	NPC105512
0.9448	High Similarity	NPC216318
0.9448	High Similarity	NPC259713
0.9448	High Similarity	NPC183959
0.9448	High Similarity	NPC17286
0.9448	High Similarity	NPC1612
0.9448	High Similarity	NPC296197
0.9444	High Similarity	NPC188074
0.9444	High Similarity	NPC125449
0.9444	High Similarity	NPC95864
0.9441	High Similarity	NPC70136
0.9396	High Similarity	NPC299520
0.9396	High Similarity	NPC304008
0.9396	High Similarity	NPC218313
0.9396	High Similarity	NPC474681
0.9396	High Similarity	NPC180011
0.9396	High Similarity	NPC219867
0.9396	High Similarity	NPC129684
0.9396	High Similarity	NPC99597
0.9396	High Similarity	NPC210084
0.9396	High Similarity	NPC187745
0.9396	High Similarity	NPC161960
0.9392	High Similarity	NPC472280
0.9392	High Similarity	NPC2928
0.9388	High Similarity	NPC39732
0.9388	High Similarity	NPC302950
0.9388	High Similarity	NPC236637
0.9388	High Similarity	NPC219582
0.9388	High Similarity	NPC260979
0.9388	High Similarity	NPC472912
0.9388	High Similarity	NPC60972
0.9384	High Similarity	NPC179183
0.9384	High Similarity	NPC62042
0.9384	High Similarity	NPC260582
0.9379	High Similarity	NPC321011
0.9379	High Similarity	NPC3036
0.9379	High Similarity	NPC12367
0.9379	High Similarity	NPC118726
0.9379	High Similarity	NPC188679
0.9379	High Similarity	NPC294852
0.9371	High Similarity	NPC279121
0.9333	High Similarity	NPC204879
0.9333	High Similarity	NPC55738
0.9329	High Similarity	NPC138243
0.9329	High Similarity	NPC68093
0.9329	High Similarity	NPC472455
0.9329	High Similarity	NPC472916
0.9329	High Similarity	NPC472907
0.9329	High Similarity	NPC191146
0.9329	High Similarity	NPC255106
0.9329	High Similarity	NPC235165
0.9324	High Similarity	NPC472905
0.9324	High Similarity	NPC256346
0.9324	High Similarity	NPC18727
0.9324	High Similarity	NPC27532
0.9324	High Similarity	NPC141212
0.9324	High Similarity	NPC246328
0.9324	High Similarity	NPC325028
0.932	High Similarity	NPC204515
0.932	High Similarity	NPC225731
0.932	High Similarity	NPC117579
0.9315	High Similarity	NPC137062
0.9315	High Similarity	NPC139293
0.9315	High Similarity	NPC183950
0.9315	High Similarity	NPC195763
0.9315	High Similarity	NPC264550
0.9315	High Similarity	NPC69430
0.9315	High Similarity	NPC264289
0.9315	High Similarity	NPC287101
0.9315	High Similarity	NPC294502
0.9315	High Similarity	NPC200221
0.9315	High Similarity	NPC52005
0.9315	High Similarity	NPC333691
0.9315	High Similarity	NPC142876
0.9315	High Similarity	NPC200060
0.9315	High Similarity	NPC223579
0.9315	High Similarity	NPC40290
0.931	High Similarity	NPC74881
0.931	High Similarity	NPC275772
0.931	High Similarity	NPC130230
0.931	High Similarity	NPC51443
0.931	High Similarity	NPC239312
0.9301	High Similarity	NPC287722
0.9301	High Similarity	NPC175013
0.9272	High Similarity	NPC188433
0.9267	High Similarity	NPC162869
0.9267	High Similarity	NPC67876
0.9267	High Similarity	NPC156057
0.9267	High Similarity	NPC474208
0.9267	High Similarity	NPC96167
0.9267	High Similarity	NPC472914
0.9267	High Similarity	NPC472913
0.9267	High Similarity	NPC136674
0.9267	High Similarity	NPC78225
0.9267	High Similarity	NPC472911
0.9267	High Similarity	NPC472963
0.9267	High Similarity	NPC222814
0.9267	High Similarity	NPC262286
0.9267	High Similarity	NPC475267
0.9267	High Similarity	NPC36852
0.9267	High Similarity	NPC474836
0.9267	High Similarity	NPC472910
0.9267	High Similarity	NPC48208
0.9267	High Similarity	NPC52530
0.9267	High Similarity	NPC245758
0.9267	High Similarity	NPC291508
0.9262	High Similarity	NPC255807
0.9262	High Similarity	NPC256612
0.9262	High Similarity	NPC20830
0.9262	High Similarity	NPC31018
0.9262	High Similarity	NPC234255
0.9257	High Similarity	NPC83508
0.9257	High Similarity	NPC61506
0.9257	High Similarity	NPC71334
0.9257	High Similarity	NPC212678
0.9257	High Similarity	NPC100887
0.9257	High Similarity	NPC275836
0.9257	High Similarity	NPC301323
0.9257	High Similarity	NPC239128
0.9257	High Similarity	NPC25270
0.9257	High Similarity	NPC156222
0.9257	High Similarity	NPC240476
0.9257	High Similarity	NPC237994
0.9257	High Similarity	NPC55205
0.9257	High Similarity	NPC293183
0.9257	High Similarity	NPC57030
0.9257	High Similarity	NPC256283
0.9257	High Similarity	NPC187498
0.9257	High Similarity	NPC162313
0.9257	High Similarity	NPC27208
0.9257	High Similarity	NPC188203
0.9257	High Similarity	NPC36835
0.9257	High Similarity	NPC246162
0.9257	High Similarity	NPC131624
0.9257	High Similarity	NPC9743
0.9257	High Similarity	NPC275722
0.9257	High Similarity	NPC222830
0.9257	High Similarity	NPC120163
0.9257	High Similarity	NPC260491
0.9257	High Similarity	NPC241498
0.9257	High Similarity	NPC198826
0.9257	High Similarity	NPC142540
0.9247	High Similarity	NPC203747
0.9247	High Similarity	NPC80710
0.9247	High Similarity	NPC254702
0.9247	High Similarity	NPC194653
0.9247	High Similarity	NPC287395
0.9247	High Similarity	NPC183655
0.9247	High Similarity	NPC139364
0.9247	High Similarity	NPC120464

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 NPC77378 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	497
0.1-0.2	1081
0.2-0.3	2023
0.3-0.4	2659
0.4-0.5	1554
0.5-0.6	916
0.6-0.7	283
0.7-0.8	84
0.8-0.85	36
0.85-0.9	10
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9388	High Similarity	NPD1934	Approved
0.9371	High Similarity	NPD1511	Approved
0.9241	High Similarity	NPD1512	Approved
0.9195	High Similarity	NPD2801	Approved
0.9073	High Similarity	NPD3882	Suspended
0.9067	High Similarity	NPD2393	Clinical (unspecified phase)
0.8889	High Similarity	NPD1549	Phase 2
0.8819	High Similarity	NPD1552	Clinical (unspecified phase)
0.8819	High Similarity	NPD1550	Clinical (unspecified phase)
0.8816	High Similarity	NPD1465	Phase 2
0.8797	High Similarity	NPD3818	Discontinued
0.8794	High Similarity	NPD943	Approved
0.879	High Similarity	NPD6167	Clinical (unspecified phase)
0.879	High Similarity	NPD6168	Clinical (unspecified phase)
0.879	High Similarity	NPD6166	Phase 2
0.8701	High Similarity	NPD4868	Clinical (unspecified phase)
0.8681	High Similarity	NPD1510	Phase 2
0.8571	High Similarity	NPD7074	Phase 3
0.8531	High Similarity	NPD1240	Approved
0.8516	High Similarity	NPD3817	Phase 2
0.8509	High Similarity	NPD7054	Approved
0.8497	Intermediate Similarity	NPD4380	Phase 2
0.8457	Intermediate Similarity	NPD7472	Approved
0.8418	Intermediate Similarity	NPD5494	Approved
0.8415	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1607	Approved
0.8411	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD7075	Discontinued
0.838	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6797	Phase 2
0.8289	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD2796	Approved
0.8242	Intermediate Similarity	NPD7251	Discontinued
0.8224	Intermediate Similarity	NPD6799	Approved
0.8217	Intermediate Similarity	NPD7819	Suspended
0.8199	Intermediate Similarity	NPD6232	Discontinued
0.8193	Intermediate Similarity	NPD7808	Phase 3
0.8182	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD3749	Approved
0.816	Intermediate Similarity	NPD7473	Discontinued
0.8153	Intermediate Similarity	NPD6801	Discontinued
0.8151	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1613	Approved
0.8146	Intermediate Similarity	NPD3750	Approved
0.8095	Intermediate Similarity	NPD447	Suspended
0.8089	Intermediate Similarity	NPD7411	Suspended
0.8054	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD3926	Phase 2
0.8025	Intermediate Similarity	NPD1247	Approved
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7973	Intermediate Similarity	NPD230	Phase 1
0.7961	Intermediate Similarity	NPD2800	Approved
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.7937	Intermediate Similarity	NPD5402	Approved
0.7914	Intermediate Similarity	NPD6959	Discontinued
0.7844	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD5403	Approved
0.7829	Intermediate Similarity	NPD2344	Approved
0.7821	Intermediate Similarity	NPD5401	Approved
0.7815	Intermediate Similarity	NPD3748	Approved
0.7815	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6559	Discontinued
0.7808	Intermediate Similarity	NPD9494	Approved
0.7793	Intermediate Similarity	NPD1203	Approved
0.7771	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1933	Approved
0.7727	Intermediate Similarity	NPD1243	Approved
0.7722	Intermediate Similarity	NPD920	Approved
0.7669	Intermediate Similarity	NPD7768	Phase 2
0.7651	Intermediate Similarity	NPD2313	Discontinued
0.7647	Intermediate Similarity	NPD6099	Approved
0.7647	Intermediate Similarity	NPD6100	Approved
0.7647	Intermediate Similarity	NPD2935	Discontinued
0.7639	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2309	Approved
0.7625	Intermediate Similarity	NPD3226	Approved
0.7613	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2346	Discontinued
0.7595	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD9269	Phase 2
0.7584	Intermediate Similarity	NPD3027	Phase 3
0.7582	Intermediate Similarity	NPD2799	Discontinued
0.758	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3751	Discontinued
0.7564	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4628	Phase 3
0.7562	Intermediate Similarity	NPD1653	Approved
0.7534	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7484	Intermediate Similarity	NPD2532	Approved
0.7484	Intermediate Similarity	NPD2533	Approved
0.7484	Intermediate Similarity	NPD2534	Approved
0.7466	Intermediate Similarity	NPD9717	Approved
0.7452	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6651	Approved
0.7442	Intermediate Similarity	NPD5953	Discontinued
0.7432	Intermediate Similarity	NPD1470	Approved
0.7427	Intermediate Similarity	NPD7286	Phase 2
0.7405	Intermediate Similarity	NPD6190	Approved
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6234	Discontinued
0.7361	Intermediate Similarity	NPD1548	Phase 1
0.7347	Intermediate Similarity	NPD1608	Approved
0.7337	Intermediate Similarity	NPD3787	Discontinued
0.733	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD9268	Approved
0.7303	Intermediate Similarity	NPD411	Approved
0.7285	Intermediate Similarity	NPD4908	Phase 1
0.7279	Intermediate Similarity	NPD1201	Approved
0.7279	Intermediate Similarity	NPD422	Phase 1
0.7267	Intermediate Similarity	NPD2798	Approved
0.7257	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4308	Phase 3
0.7222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8312	Approved
0.7216	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD4287	Approved
0.7205	Intermediate Similarity	NPD7390	Discontinued
0.72	Intermediate Similarity	NPD7685	Pre-registration
0.7193	Intermediate Similarity	NPD5242	Approved
0.719	Intermediate Similarity	NPD3764	Approved
0.719	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3268	Approved
0.7186	Intermediate Similarity	NPD4288	Approved
0.7171	Intermediate Similarity	NPD6832	Phase 2
0.7169	Intermediate Similarity	NPD37	Approved
0.7168	Intermediate Similarity	NPD7228	Approved
0.7161	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7143	Intermediate Similarity	NPD4965	Approved
0.7133	Intermediate Similarity	NPD3225	Approved
0.7124	Intermediate Similarity	NPD4625	Phase 3
0.7099	Intermediate Similarity	NPD4357	Discontinued
0.7086	Intermediate Similarity	NPD2797	Approved
0.7083	Intermediate Similarity	NPD2296	Approved
0.7083	Intermediate Similarity	NPD5353	Approved
0.7081	Intermediate Similarity	NPD2354	Approved
0.7078	Intermediate Similarity	NPD1296	Phase 2
0.7067	Intermediate Similarity	NPD4749	Approved
0.7065	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5536	Phase 2
0.7052	Intermediate Similarity	NPD2403	Approved
0.7041	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5711	Approved
0.7035	Intermediate Similarity	NPD5710	Approved
0.7025	Intermediate Similarity	NPD7033	Discontinued
0.7007	Intermediate Similarity	NPD9545	Approved
0.7006	Intermediate Similarity	NPD6386	Approved
0.7006	Intermediate Similarity	NPD6385	Approved
0.7	Intermediate Similarity	NPD8434	Phase 2
0.6993	Remote Similarity	NPD3018	Phase 2
0.6993	Remote Similarity	NPD228	Approved
0.6989	Remote Similarity	NPD1729	Discontinued
0.6988	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1558	Phase 1
0.6987	Remote Similarity	NPD4307	Phase 2
0.6986	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD9493	Approved
0.6981	Remote Similarity	NPD5404	Approved
0.6981	Remote Similarity	NPD5405	Approved
0.6981	Remote Similarity	NPD5406	Approved
0.6981	Remote Similarity	NPD5408	Approved
0.6974	Remote Similarity	NPD1164	Approved
0.6974	Remote Similarity	NPD3267	Approved
0.6974	Remote Similarity	NPD3266	Approved
0.6968	Remote Similarity	NPD6798	Discontinued
0.6964	Remote Similarity	NPD6844	Discontinued
0.6957	Remote Similarity	NPD2654	Approved
0.6957	Remote Similarity	NPD4363	Phase 3
0.6957	Remote Similarity	NPD4360	Phase 2
0.6954	Remote Similarity	NPD2899	Discontinued
0.6952	Remote Similarity	NPD6782	Approved
0.6952	Remote Similarity	NPD6776	Approved
0.6952	Remote Similarity	NPD6780	Approved
0.6952	Remote Similarity	NPD6777	Approved
0.6952	Remote Similarity	NPD6781	Approved
0.6952	Remote Similarity	NPD6778	Approved
0.6952	Remote Similarity	NPD6779	Approved
0.6951	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8151	Discontinued
0.6911	Remote Similarity	NPD7584	Approved
0.691	Remote Similarity	NPD6104	Discontinued
0.6906	Remote Similarity	NPD8150	Discontinued

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