NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	346.14
Volume:	354.353
LogP:	2.963
LogD:	3.283
LogS:	-4.656
# Rotatable Bonds:	8
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	2.107
Fsp3:	0.316
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:	-4.808
MDCK Permeability:	3.6878391256323084e-05
Pgp-inhibitor:	0.252
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	82.54944610595703%
Volume Distribution (VD):	0.537
Pgp-substrate:	8.948461532592773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.889
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.765
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.569
CYP2C9-substrate:	0.911
CYP2D6-inhibitor:	0.538
CYP2D6-substrate:	0.939
CYP3A4-inhibitor:	0.893
CYP3A4-substrate:	0.546

ADMET: Excretion

Clearance (CL):	10.683
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.151
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.654
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.15
Skin Sensitization:	0.373
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.132
Respiratory Toxicity:	0.738

Download Data

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

Natural Product: NPC207729

Natural Product ID:	NPC207729
*Common Name:**	2,3,6,7-Tethrahydroxyxanthone
IUPAC Name:	2,3,6,7-tetrahydroxyxanthen-9-one
Synonyms:	2,3,6,7-Tethrahydroxyxanthone
Standard InCHIKey:	FBMMWMPAZUAGMX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O6/c14-7-1-5-11(3-9(7)16)19-12-4-10(17)8(15)2-6(12)13(5)18/h1-4,14-17H
SMILES:	Oc1cc2c(cc1O)oc1c(c2=O)cc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL12700
PubChem CID:	10355231
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	1
Others	3

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	IC50	=	769000.0	nM	PMID[493456]
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	Inhibition	=	11.68	%	PMID[493456]
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	Inhibition	=	17.23	%	PMID[493456]
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	Inhibition	=	26.76	%	PMID[493456]

☑ 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 NPC207729 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	2376
0.2-0.3	6212
0.3-0.4	11912
0.4-0.5	4301
0.5-0.6	4493
0.6-0.7	5096
0.7-0.8	4583
0.8-0.85	1814
0.85-0.9	860
0.9-0.95	421
0.95-1	68

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC194856
0.979	High Similarity	NPC248102
0.9789	High Similarity	NPC276930
0.9722	High Similarity	NPC251110
0.9722	High Similarity	NPC171010
0.9655	High Similarity	NPC39007
0.9655	High Similarity	NPC101996
0.9655	High Similarity	NPC161277
0.9653	High Similarity	NPC61620
0.9653	High Similarity	NPC62042
0.965	High Similarity	NPC12367
0.965	High Similarity	NPC118726
0.9589	High Similarity	NPC271779
0.9589	High Similarity	NPC167091
0.9589	High Similarity	NPC292214
0.9589	High Similarity	NPC88645
0.9589	High Similarity	NPC206238
0.9586	High Similarity	NPC202157
0.9586	High Similarity	NPC204515
0.958	High Similarity	NPC77378
0.958	High Similarity	NPC275772
0.958	High Similarity	NPC130230
0.958	High Similarity	NPC239312
0.9524	High Similarity	NPC113906
0.9521	High Similarity	NPC120537
0.9521	High Similarity	NPC199100
0.9521	High Similarity	NPC180234
0.9517	High Similarity	NPC45873
0.9517	High Similarity	NPC179183
0.9514	High Similarity	NPC196277
0.9514	High Similarity	NPC272721
0.9514	High Similarity	NPC43669
0.9459	High Similarity	NPC138243
0.9456	High Similarity	NPC89474
0.9452	High Similarity	NPC149614
0.9448	High Similarity	NPC216318
0.9448	High Similarity	NPC259713
0.9448	High Similarity	NPC183959
0.9448	High Similarity	NPC195351
0.9448	High Similarity	NPC17286
0.9448	High Similarity	NPC296197
0.9448	High Similarity	NPC1612
0.9441	High Similarity	NPC70136
0.9437	High Similarity	NPC159855
0.9437	High Similarity	NPC175013
0.9437	High Similarity	NPC169479
0.9396	High Similarity	NPC36852
0.9396	High Similarity	NPC79053
0.9396	High Similarity	NPC262286
0.9396	High Similarity	NPC210084
0.9396	High Similarity	NPC99597
0.9392	High Similarity	NPC2928
0.9388	High Similarity	NPC125300
0.9384	High Similarity	NPC29231
0.9384	High Similarity	NPC77858
0.9384	High Similarity	NPC184136
0.9379	High Similarity	NPC321011
0.9379	High Similarity	NPC188679
0.9379	High Similarity	NPC218490
0.9379	High Similarity	NPC294852
0.9371	High Similarity	NPC279121
0.9333	High Similarity	NPC172770
0.9333	High Similarity	NPC185258
0.9329	High Similarity	NPC235165
0.9329	High Similarity	NPC274730
0.9329	High Similarity	NPC201837
0.9329	High Similarity	NPC142339
0.9329	High Similarity	NPC472916
0.9329	High Similarity	NPC191146
0.9329	High Similarity	NPC68093
0.9329	High Similarity	NPC255106
0.932	High Similarity	NPC225731
0.932	High Similarity	NPC117579
0.9315	High Similarity	NPC294502
0.9315	High Similarity	NPC200221
0.9315	High Similarity	NPC105512
0.931	High Similarity	NPC168803
0.931	High Similarity	NPC51443
0.931	High Similarity	NPC74881
0.931	High Similarity	NPC95864
0.9267	High Similarity	NPC162869
0.9267	High Similarity	NPC236796
0.9267	High Similarity	NPC472911
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	NPC78225
0.9267	High Similarity	NPC222814
0.9267	High Similarity	NPC300727
0.9267	High Similarity	NPC475267
0.9267	High Similarity	NPC474836
0.9267	High Similarity	NPC48208
0.9267	High Similarity	NPC472910
0.9267	High Similarity	NPC245758
0.9267	High Similarity	NPC241904
0.9267	High Similarity	NPC469584
0.9262	High Similarity	NPC208197
0.9262	High Similarity	NPC256612
0.9262	High Similarity	NPC20830
0.9257	High Similarity	NPC131624
0.9257	High Similarity	NPC83508
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	NPC71334
0.9257	High Similarity	NPC249570
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	NPC198826
0.9257	High Similarity	NPC188203
0.9257	High Similarity	NPC275722
0.9257	High Similarity	NPC222830
0.9257	High Similarity	NPC120163
0.9257	High Similarity	NPC241498
0.9257	High Similarity	NPC142540
0.9252	High Similarity	NPC151473
0.9252	High Similarity	NPC10467
0.9247	High Similarity	NPC3036
0.9247	High Similarity	NPC287395
0.9247	High Similarity	NPC183655
0.9241	High Similarity	NPC20791
0.9241	High Similarity	NPC179271
0.9241	High Similarity	NPC169749
0.9236	High Similarity	NPC59551
0.9211	High Similarity	NPC472275
0.9211	High Similarity	NPC167678
0.9211	High Similarity	NPC29876
0.9211	High Similarity	NPC308992
0.9211	High Similarity	NPC162668
0.9211	High Similarity	NPC228383
0.9205	High Similarity	NPC329091
0.9205	High Similarity	NPC476242
0.9205	High Similarity	NPC100123
0.92	High Similarity	NPC474638
0.9195	High Similarity	NPC246328
0.9195	High Similarity	NPC476631
0.9195	High Similarity	NPC325028
0.9195	High Similarity	NPC22519
0.9195	High Similarity	NPC33051
0.9195	High Similarity	NPC176775
0.9195	High Similarity	NPC273462
0.9195	High Similarity	NPC274327
0.9195	High Similarity	NPC183878
0.9195	High Similarity	NPC145379
0.9195	High Similarity	NPC27532
0.9195	High Similarity	NPC227337
0.9195	High Similarity	NPC141212
0.9195	High Similarity	NPC69394
0.9195	High Similarity	NPC70433
0.9195	High Similarity	NPC75279
0.9195	High Similarity	NPC160951
0.9195	High Similarity	NPC280937
0.9195	High Similarity	NPC276409
0.9195	High Similarity	NPC472915
0.9195	High Similarity	NPC231018
0.9195	High Similarity	NPC47781
0.9195	High Similarity	NPC256346
0.9195	High Similarity	NPC255350
0.9195	High Similarity	NPC250822
0.9195	High Similarity	NPC49402
0.9189	High Similarity	NPC31363
0.9189	High Similarity	NPC45291
0.9189	High Similarity	NPC19980
0.9178	High Similarity	NPC30647
0.9178	High Similarity	NPC61871
0.9178	High Similarity	NPC46941
0.9178	High Similarity	NPC55557
0.9178	High Similarity	NPC108406
0.9172	High Similarity	NPC472917
0.9167	High Similarity	NPC287722
0.9155	High Similarity	NPC18457
0.915	High Similarity	NPC472448
0.915	High Similarity	NPC470694
0.915	High Similarity	NPC329760
0.915	High Similarity	NPC83922
0.915	High Similarity	NPC220912
0.9145	High Similarity	NPC235018
0.9145	High Similarity	NPC228785
0.9145	High Similarity	NPC476980
0.9145	High Similarity	NPC56085
0.9145	High Similarity	NPC80375
0.9145	High Similarity	NPC263449
0.9145	High Similarity	NPC320359
0.9145	High Similarity	NPC139036
0.9145	High Similarity	NPC45146
0.9145	High Similarity	NPC119224
0.9145	High Similarity	NPC200746
0.9145	High Similarity	NPC204290
0.9145	High Similarity	NPC14353
0.9139	High Similarity	NPC129684

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 NPC207729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	498
0.1-0.2	1082
0.2-0.3	2093
0.3-0.4	2677
0.4-0.5	1534
0.5-0.6	879
0.6-0.7	254
0.7-0.8	94
0.8-0.85	28
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9371	High Similarity	NPD1511	Approved
0.9241	High Similarity	NPD1512	Approved
0.9195	High Similarity	NPD2801	Approved
0.9128	High Similarity	NPD1934	Approved
0.9067	High Similarity	NPD2393	Clinical (unspecified phase)
0.8759	High Similarity	NPD1549	Phase 2
0.8701	High Similarity	NPD4868	Clinical (unspecified phase)
0.8701	High Similarity	NPD3882	Suspended
0.8693	High Similarity	NPD1465	Phase 2
0.869	High Similarity	NPD1552	Clinical (unspecified phase)
0.869	High Similarity	NPD1550	Clinical (unspecified phase)
0.8662	High Similarity	NPD943	Approved
0.8562	High Similarity	NPD3818	Discontinued
0.8553	High Similarity	NPD6168	Clinical (unspecified phase)
0.8553	High Similarity	NPD6167	Clinical (unspecified phase)
0.8553	High Similarity	NPD6166	Phase 2
0.8552	High Similarity	NPD1510	Phase 2
0.8418	Intermediate Similarity	NPD5494	Approved
0.8415	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD1240	Approved
0.8377	Intermediate Similarity	NPD4380	Phase 2
0.8344	Intermediate Similarity	NPD7074	Phase 3
0.831	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1607	Approved
0.8282	Intermediate Similarity	NPD7054	Approved
0.828	Intermediate Similarity	NPD3817	Phase 2
0.8252	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7472	Approved
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.8182	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7075	Discontinued
0.817	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7251	Discontinued
0.8121	Intermediate Similarity	NPD2796	Approved
0.8101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD230	Phase 1
0.8079	Intermediate Similarity	NPD2800	Approved
0.8063	Intermediate Similarity	NPD3749	Approved
0.8054	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD5402	Approved
0.8027	Intermediate Similarity	NPD1613	Approved
0.8027	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3750	Approved
0.8025	Intermediate Similarity	NPD1247	Approved
0.8025	Intermediate Similarity	NPD6959	Discontinued
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6799	Approved
0.7976	Intermediate Similarity	NPD7808	Phase 3
0.7975	Intermediate Similarity	NPD6232	Discontinued
0.7975	Intermediate Similarity	NPD7411	Suspended
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.7939	Intermediate Similarity	NPD7473	Discontinued
0.7937	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6801	Discontinued
0.7881	Intermediate Similarity	NPD2935	Discontinued
0.7881	Intermediate Similarity	NPD1551	Phase 2
0.7852	Intermediate Similarity	NPD447	Suspended
0.7815	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6599	Discontinued
0.7738	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1243	Approved
0.7722	Intermediate Similarity	NPD920	Approved
0.7712	Intermediate Similarity	NPD2344	Approved
0.7711	Intermediate Similarity	NPD3926	Phase 2
0.7708	Intermediate Similarity	NPD9269	Phase 2
0.7706	Intermediate Similarity	NPD6559	Discontinued
0.7697	Intermediate Similarity	NPD3748	Approved
0.7683	Intermediate Similarity	NPD919	Approved
0.7671	Intermediate Similarity	NPD1203	Approved
0.7665	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2313	Discontinued
0.7647	Intermediate Similarity	NPD6099	Approved
0.7647	Intermediate Similarity	NPD6100	Approved
0.7625	Intermediate Similarity	NPD3226	Approved
0.761	Intermediate Similarity	NPD5403	Approved
0.7597	Intermediate Similarity	NPD2346	Discontinued
0.7595	Intermediate Similarity	NPD2534	Approved
0.7595	Intermediate Similarity	NPD5401	Approved
0.7595	Intermediate Similarity	NPD2533	Approved
0.7595	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2532	Approved
0.7574	Intermediate Similarity	NPD3751	Discontinued
0.7562	Intermediate Similarity	NPD1653	Approved
0.7561	Intermediate Similarity	NPD7768	Phase 2
0.7517	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7468	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6651	Approved
0.745	Intermediate Similarity	NPD9494	Approved
0.7431	Intermediate Similarity	NPD9268	Approved
0.7427	Intermediate Similarity	NPD7286	Phase 2
0.7417	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6190	Approved
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1610	Phase 2
0.7386	Intermediate Similarity	NPD1933	Approved
0.7351	Intermediate Similarity	NPD3027	Phase 3
0.7347	Intermediate Similarity	NPD9717	Approved
0.7342	Intermediate Similarity	NPD4628	Phase 3
0.7341	Intermediate Similarity	NPD5953	Discontinued
0.7337	Intermediate Similarity	NPD3787	Discontinued
0.7322	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1470	Approved
0.7312	Intermediate Similarity	NPD7390	Discontinued
0.7262	Intermediate Similarity	NPD6234	Discontinued
0.7241	Intermediate Similarity	NPD1548	Phase 1
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1608	Approved
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD411	Approved
0.7181	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.7171	Intermediate Similarity	NPD4908	Phase 1
0.7169	Intermediate Similarity	NPD6844	Discontinued
0.7162	Intermediate Similarity	NPD422	Phase 1
0.7162	Intermediate Similarity	NPD1201	Approved
0.7161	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2798	Approved
0.7135	Intermediate Similarity	NPD5711	Approved
0.7135	Intermediate Similarity	NPD5710	Approved
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7119	Intermediate Similarity	NPD8313	Approved
0.7119	Intermediate Similarity	NPD8312	Approved
0.7114	Intermediate Similarity	NPD1481	Phase 2
0.7111	Intermediate Similarity	NPD4287	Approved
0.7105	Intermediate Similarity	NPD2861	Phase 2
0.7093	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4288	Approved
0.7078	Intermediate Similarity	NPD3268	Approved
0.7078	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3764	Approved
0.7069	Intermediate Similarity	NPD7228	Approved
0.7067	Intermediate Similarity	NPD4749	Approved
0.7066	Intermediate Similarity	NPD37	Approved
0.7059	Intermediate Similarity	NPD6832	Phase 2
0.7055	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2403	Approved
0.7047	Intermediate Similarity	NPD1535	Discovery
0.7044	Intermediate Similarity	NPD1471	Phase 3
0.7043	Intermediate Similarity	NPD6777	Approved
0.7043	Intermediate Similarity	NPD6776	Approved
0.7043	Intermediate Similarity	NPD6779	Approved
0.7043	Intermediate Similarity	NPD6780	Approved
0.7043	Intermediate Similarity	NPD6778	Approved
0.7043	Intermediate Similarity	NPD6781	Approved
0.7043	Intermediate Similarity	NPD6782	Approved
0.7041	Intermediate Similarity	NPD4967	Phase 2
0.7041	Intermediate Similarity	NPD4965	Approved
0.7041	Intermediate Similarity	NPD4966	Approved
0.7027	Intermediate Similarity	NPD17	Approved
0.702	Intermediate Similarity	NPD3225	Approved
0.7013	Intermediate Similarity	NPD4625	Phase 3
0.7006	Intermediate Similarity	NPD7685	Pre-registration
0.7	Intermediate Similarity	NPD8434	Phase 2
0.6994	Remote Similarity	NPD5242	Approved
0.6982	Remote Similarity	NPD2296	Approved
0.6982	Remote Similarity	NPD5353	Approved
0.6974	Remote Similarity	NPD2797	Approved
0.6968	Remote Similarity	NPD1296	Phase 2
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
0.6931	Remote Similarity	NPD7435	Discontinued
0.6927	Remote Similarity	NPD8151	Discontinued
0.6918	Remote Similarity	NPD7033	Discontinued
0.6906	Remote Similarity	NPD8150	Discontinued
0.6905	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD1729	Discontinued
0.6892	Remote Similarity	NPD9545	Approved
0.6886	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4307	Phase 2
0.6875	Remote Similarity	NPD5404	Approved
0.6875	Remote Similarity	NPD5406	Approved
0.6875	Remote Similarity	NPD5408	Approved
0.6875	Remote Similarity	NPD5405	Approved
0.6871	Remote Similarity	NPD9493	Approved
0.6871	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2354	Approved
0.6863	Remote Similarity	NPD3266	Approved
0.6863	Remote Similarity	NPD3267	Approved
0.6863	Remote Similarity	NPD1164	Approved
0.6842	Remote Similarity	NPD7697	Approved
0.6842	Remote Similarity	NPD7696	Phase 3
0.6842	Remote Similarity	NPD7698	Approved
0.6839	Remote Similarity	NPD7229	Phase 3
0.6823	Remote Similarity	NPD7584	Approved
0.6818	Remote Similarity	NPD1019	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