NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.04
Volume:	233.231
LogP:	2.109
LogD:	1.84
LogS:	-3.533
# Rotatable Bonds:	0
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	2.395
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:	-5.028
MDCK Permeability:	1.3430459148366936e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.675

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	94.57177734375%
Volume Distribution (VD):	0.619
Pgp-substrate:	9.914817810058594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.51
CYP2C9-substrate:	0.619
CYP2D6-inhibitor:	0.375
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	7.571
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.777
Rat Oral Acute Toxicity:	0.565
Maximum Recommended Daily Dose:	0.166
Skin Sensitization:	0.919
Carcinogencity:	0.8
Eye Corrosion:	0.027
Eye Irritation:	0.918
Respiratory Toxicity:	0.208

Download Data

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

Natural Product: NPC43669

Natural Product ID:	NPC43669
*Common Name:**	3,4,5-Trihydroxyxanthen-9-One
IUPAC Name:	3,4,5-trihydroxyxanthen-9-one
Synonyms:
Standard InCHIKey:	GYXLJFKBGTVCHD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O5/c14-8-5-4-7-10(16)6-2-1-3-9(15)12(6)18-13(7)11(8)17/h1-5,14-15,17H
SMILES:	Oc1c(O)ccc2c1oc1c(O)cccc1c2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3704818
PubChem CID:	46209537
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
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473425]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975482]
NPO22748	Neophaeosphaeria quadriseptata	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499313]
NPO24232	Boehmeria pannosa	Species	Urticaceae	Eukaryota	roots	n.a.	n.a.	PMID[16872154]
NPO26529	Hypericum oblongifolium	Species	Hypericaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16880649]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7494150]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673926]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673935]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673936]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[8946744]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8991944]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[9584396]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25812	Dipentodon sinicus	Species	Dipentodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24232	Boehmeria pannosa	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3170	Piper lanceifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22748	Neophaeosphaeria quadriseptata	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26315	Trikentrion flabelliforme	Species	Raspailiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4308	Pericome caudata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25943	Cirsium carolinianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26529	Hypericum oblongifolium	Species	Hypericaceae	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

Activity Type	# Activity
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	10000.0	nM	PMID[559330]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	10000	nM	Patent: US9114126 B2

☑ 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 NPC43669 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	563
0.1-0.2	2306
0.2-0.3	5972
0.3-0.4	11551
0.4-0.5	4677
0.5-0.6	4352
0.6-0.7	5054
0.7-0.8	4670
0.8-0.85	1916
0.85-0.9	1022
0.9-0.95	430
0.95-1	184

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC196277
1.0	High Similarity	NPC272721
0.9929	High Similarity	NPC77378
0.986	High Similarity	NPC29231
0.9792	High Similarity	NPC251110
0.9789	High Similarity	NPC168803
0.9722	High Similarity	NPC61620
0.9722	High Similarity	NPC248102
0.9716	High Similarity	NPC59551
0.9658	High Similarity	NPC70433
0.9658	High Similarity	NPC88645
0.9658	High Similarity	NPC33051
0.9658	High Similarity	NPC167091
0.9658	High Similarity	NPC206238
0.9658	High Similarity	NPC49402
0.9658	High Similarity	NPC292214
0.9658	High Similarity	NPC227337
0.9658	High Similarity	NPC273462
0.9658	High Similarity	NPC271779
0.9655	High Similarity	NPC31363
0.9592	High Similarity	NPC230149
0.9592	High Similarity	NPC168247
0.9592	High Similarity	NPC117992
0.9592	High Similarity	NPC152951
0.9592	High Similarity	NPC57674
0.9589	High Similarity	NPC161277
0.9589	High Similarity	NPC39007
0.9589	High Similarity	NPC257648
0.9589	High Similarity	NPC101996
0.9589	High Similarity	NPC199100
0.9589	High Similarity	NPC477231
0.9589	High Similarity	NPC120537
0.9589	High Similarity	NPC180234
0.9586	High Similarity	NPC151473
0.9586	High Similarity	NPC45873
0.9583	High Similarity	NPC194856
0.9583	High Similarity	NPC276930
0.958	High Similarity	NPC209278
0.9527	High Similarity	NPC5322
0.9527	High Similarity	NPC474638
0.9527	High Similarity	NPC6633
0.9527	High Similarity	NPC133970
0.9524	High Similarity	NPC469550
0.9521	High Similarity	NPC171010
0.9521	High Similarity	NPC149614
0.9517	High Similarity	NPC1612
0.9517	High Similarity	NPC183959
0.9517	High Similarity	NPC296197
0.9517	High Similarity	NPC259713
0.9517	High Similarity	NPC17286
0.9517	High Similarity	NPC216318
0.9517	High Similarity	NPC105512
0.9514	High Similarity	NPC125449
0.9514	High Similarity	NPC95864
0.9514	High Similarity	NPC188074
0.9514	High Similarity	NPC207729
0.951	High Similarity	NPC70136
0.9463	High Similarity	NPC474681
0.9463	High Similarity	NPC99597
0.9463	High Similarity	NPC187745
0.9463	High Similarity	NPC218313
0.9463	High Similarity	NPC210084
0.9463	High Similarity	NPC129684
0.9463	High Similarity	NPC161960
0.9463	High Similarity	NPC304008
0.9463	High Similarity	NPC299520
0.9459	High Similarity	NPC2928
0.9459	High Similarity	NPC472280
0.9459	High Similarity	NPC200246
0.9459	High Similarity	NPC256925
0.9456	High Similarity	NPC260979
0.9456	High Similarity	NPC39732
0.9456	High Similarity	NPC219582
0.9456	High Similarity	NPC60972
0.9456	High Similarity	NPC302950
0.9456	High Similarity	NPC236637
0.9456	High Similarity	NPC472912
0.9452	High Similarity	NPC179183
0.9452	High Similarity	NPC260582
0.9452	High Similarity	NPC62042
0.9448	High Similarity	NPC294852
0.9448	High Similarity	NPC118726
0.9448	High Similarity	NPC321011
0.9448	High Similarity	NPC3036
0.9448	High Similarity	NPC12367
0.9448	High Similarity	NPC188679
0.9441	High Similarity	NPC279121
0.94	High Similarity	NPC55738
0.94	High Similarity	NPC204879
0.9396	High Similarity	NPC255106
0.9396	High Similarity	NPC115853
0.9396	High Similarity	NPC235165
0.9396	High Similarity	NPC472907
0.9396	High Similarity	NPC191146
0.9396	High Similarity	NPC138243
0.9396	High Similarity	NPC68093
0.9396	High Similarity	NPC470600
0.9396	High Similarity	NPC472916
0.9396	High Similarity	NPC472455
0.9392	High Similarity	NPC18727
0.9392	High Similarity	NPC472905
0.9392	High Similarity	NPC27532
0.9392	High Similarity	NPC141212
0.9392	High Similarity	NPC246328
0.9392	High Similarity	NPC325028
0.9392	High Similarity	NPC256346
0.9388	High Similarity	NPC117579
0.9388	High Similarity	NPC204515
0.9388	High Similarity	NPC225731
0.9384	High Similarity	NPC264550
0.9384	High Similarity	NPC69430
0.9384	High Similarity	NPC200060
0.9384	High Similarity	NPC139293
0.9384	High Similarity	NPC40290
0.9384	High Similarity	NPC287101
0.9384	High Similarity	NPC52005
0.9384	High Similarity	NPC142876
0.9384	High Similarity	NPC294502
0.9384	High Similarity	NPC223579
0.9384	High Similarity	NPC195763
0.9384	High Similarity	NPC264289
0.9384	High Similarity	NPC137062
0.9384	High Similarity	NPC183950
0.9384	High Similarity	NPC200221
0.9384	High Similarity	NPC333691
0.9379	High Similarity	NPC51443
0.9379	High Similarity	NPC239312
0.9379	High Similarity	NPC74881
0.9379	High Similarity	NPC130230
0.9379	High Similarity	NPC275772
0.9371	High Similarity	NPC175013
0.9371	High Similarity	NPC287722
0.9333	High Similarity	NPC136674
0.9333	High Similarity	NPC78225
0.9333	High Similarity	NPC472910
0.9333	High Similarity	NPC180011
0.9333	High Similarity	NPC67876
0.9333	High Similarity	NPC222814
0.9333	High Similarity	NPC474208
0.9333	High Similarity	NPC291508
0.9333	High Similarity	NPC52530
0.9333	High Similarity	NPC474836
0.9333	High Similarity	NPC36852
0.9333	High Similarity	NPC262286
0.9333	High Similarity	NPC96167
0.9333	High Similarity	NPC245758
0.9333	High Similarity	NPC472914
0.9333	High Similarity	NPC156057
0.9333	High Similarity	NPC162869
0.9333	High Similarity	NPC48208
0.9333	High Similarity	NPC472911
0.9333	High Similarity	NPC219867
0.9333	High Similarity	NPC472963
0.9333	High Similarity	NPC472913
0.9333	High Similarity	NPC475267
0.9329	High Similarity	NPC20830
0.9329	High Similarity	NPC234255
0.9329	High Similarity	NPC256612
0.9329	High Similarity	NPC255807
0.9329	High Similarity	NPC31018
0.9324	High Similarity	NPC241498
0.9324	High Similarity	NPC162313
0.9324	High Similarity	NPC120163
0.9324	High Similarity	NPC293183
0.9324	High Similarity	NPC188203
0.9324	High Similarity	NPC57030
0.9324	High Similarity	NPC275836
0.9324	High Similarity	NPC239128
0.9324	High Similarity	NPC260491
0.9324	High Similarity	NPC222830
0.9324	High Similarity	NPC198826
0.9324	High Similarity	NPC240476
0.9324	High Similarity	NPC55205
0.9324	High Similarity	NPC237994
0.9324	High Similarity	NPC100887
0.9324	High Similarity	NPC301323
0.9324	High Similarity	NPC212678
0.9324	High Similarity	NPC61506
0.9324	High Similarity	NPC83508
0.9324	High Similarity	NPC187498
0.9324	High Similarity	NPC246162
0.9324	High Similarity	NPC25270
0.9324	High Similarity	NPC27208
0.9324	High Similarity	NPC131624
0.9324	High Similarity	NPC9743
0.9324	High Similarity	NPC71334
0.9324	High Similarity	NPC156222
0.9324	High Similarity	NPC36835
0.9324	High Similarity	NPC275722
0.9324	High Similarity	NPC256283
0.9315	High Similarity	NPC80710
0.9315	High Similarity	NPC120464
0.9315	High Similarity	NPC203747
0.9315	High Similarity	NPC194653
0.9315	High Similarity	NPC287395
0.9315	High Similarity	NPC183655
0.9315	High Similarity	NPC139364
0.9315	High Similarity	NPC254702
0.931	High Similarity	NPC20791
0.931	High Similarity	NPC179271

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 NPC43669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	501
0.1-0.2	1056
0.2-0.3	1910
0.3-0.4	2680
0.4-0.5	1613
0.5-0.6	946
0.6-0.7	301
0.7-0.8	87
0.8-0.85	39
0.85-0.9	9
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9456	High Similarity	NPD1934	Approved
0.9441	High Similarity	NPD1511	Approved
0.931	High Similarity	NPD1512	Approved
0.9262	High Similarity	NPD2801	Approved
0.9139	High Similarity	NPD3882	Suspended
0.9133	High Similarity	NPD2393	Clinical (unspecified phase)
0.8958	High Similarity	NPD1549	Phase 2
0.8889	High Similarity	NPD1552	Clinical (unspecified phase)
0.8889	High Similarity	NPD1550	Clinical (unspecified phase)
0.8865	High Similarity	NPD943	Approved
0.8861	High Similarity	NPD3818	Discontinued
0.8854	High Similarity	NPD6167	Clinical (unspecified phase)
0.8854	High Similarity	NPD6166	Phase 2
0.8854	High Similarity	NPD6168	Clinical (unspecified phase)
0.8766	High Similarity	NPD4868	Clinical (unspecified phase)
0.8758	High Similarity	NPD1465	Phase 2
0.875	High Similarity	NPD1510	Phase 2
0.8634	High Similarity	NPD7074	Phase 3
0.8601	High Similarity	NPD1240	Approved
0.8581	High Similarity	NPD3817	Phase 2
0.8571	High Similarity	NPD7054	Approved
0.8562	High Similarity	NPD4380	Phase 2
0.8519	High Similarity	NPD7472	Approved
0.8483	Intermediate Similarity	NPD1607	Approved
0.8481	Intermediate Similarity	NPD5494	Approved
0.8477	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7075	Discontinued
0.8471	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6797	Phase 2
0.8311	Intermediate Similarity	NPD2796	Approved
0.8303	Intermediate Similarity	NPD7251	Discontinued
0.8289	Intermediate Similarity	NPD6799	Approved
0.828	Intermediate Similarity	NPD7819	Suspended
0.8261	Intermediate Similarity	NPD6232	Discontinued
0.8253	Intermediate Similarity	NPD7808	Phase 3
0.8242	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD3749	Approved
0.8221	Intermediate Similarity	NPD7473	Discontinued
0.8219	Intermediate Similarity	NPD1613	Approved
0.8219	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD3750	Approved
0.8163	Intermediate Similarity	NPD447	Suspended
0.8153	Intermediate Similarity	NPD7411	Suspended
0.8121	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6801	Discontinued
0.8098	Intermediate Similarity	NPD3926	Phase 2
0.8089	Intermediate Similarity	NPD6599	Discontinued
0.8086	Intermediate Similarity	NPD1247	Approved
0.8079	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD919	Approved
0.8067	Intermediate Similarity	NPD1551	Phase 2
0.8041	Intermediate Similarity	NPD230	Phase 1
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD5402	Approved
0.7908	Intermediate Similarity	NPD2800	Approved
0.7904	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD5403	Approved
0.7898	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2344	Approved
0.7885	Intermediate Similarity	NPD5401	Approved
0.7881	Intermediate Similarity	NPD3748	Approved
0.7881	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD9494	Approved
0.787	Intermediate Similarity	NPD6559	Discontinued
0.7866	Intermediate Similarity	NPD6959	Discontinued
0.7862	Intermediate Similarity	NPD1203	Approved
0.7831	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1933	Approved
0.7792	Intermediate Similarity	NPD1243	Approved
0.773	Intermediate Similarity	NPD7768	Phase 2
0.7718	Intermediate Similarity	NPD2313	Discontinued
0.7712	Intermediate Similarity	NPD6099	Approved
0.7712	Intermediate Similarity	NPD2935	Discontinued
0.7712	Intermediate Similarity	NPD6100	Approved
0.7708	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2309	Approved
0.7688	Intermediate Similarity	NPD3226	Approved
0.7677	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD920	Approved
0.7667	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7658	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD9269	Phase 2
0.7651	Intermediate Similarity	NPD3027	Phase 3
0.7647	Intermediate Similarity	NPD2799	Discontinued
0.7643	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3751	Discontinued
0.7628	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4628	Phase 3
0.7625	Intermediate Similarity	NPD1653	Approved
0.7603	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1610	Phase 2
0.7547	Intermediate Similarity	NPD2532	Approved
0.7547	Intermediate Similarity	NPD2533	Approved
0.7547	Intermediate Similarity	NPD2534	Approved
0.7545	Intermediate Similarity	NPD7199	Phase 2
0.7534	Intermediate Similarity	NPD9717	Approved
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7468	Intermediate Similarity	NPD6190	Approved
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7425	Intermediate Similarity	NPD6234	Discontinued
0.7415	Intermediate Similarity	NPD1608	Approved
0.7403	Intermediate Similarity	NPD6651	Approved
0.7396	Intermediate Similarity	NPD3787	Discontinued
0.7386	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7286	Phase 2
0.7379	Intermediate Similarity	NPD9268	Approved
0.7368	Intermediate Similarity	NPD411	Approved
0.7351	Intermediate Similarity	NPD4908	Phase 1
0.7347	Intermediate Similarity	NPD422	Phase 1
0.7347	Intermediate Similarity	NPD1201	Approved
0.7333	Intermediate Similarity	NPD2798	Approved
0.7314	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4308	Phase 3
0.7278	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8313	Approved
0.7273	Intermediate Similarity	NPD8312	Approved
0.7267	Intermediate Similarity	NPD7390	Discontinued
0.7263	Intermediate Similarity	NPD4287	Approved
0.7257	Intermediate Similarity	NPD7685	Pre-registration
0.7255	Intermediate Similarity	NPD3764	Approved
0.7255	Intermediate Similarity	NPD3268	Approved
0.7255	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5242	Approved
0.7246	Intermediate Similarity	NPD4288	Approved
0.7237	Intermediate Similarity	NPD6832	Phase 2
0.7229	Intermediate Similarity	NPD37	Approved
0.7226	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7228	Approved
0.7222	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1471	Phase 3
0.7211	Intermediate Similarity	NPD17	Approved
0.7202	Intermediate Similarity	NPD4967	Phase 2
0.7202	Intermediate Similarity	NPD4965	Approved
0.7202	Intermediate Similarity	NPD4966	Approved
0.72	Intermediate Similarity	NPD3225	Approved
0.719	Intermediate Similarity	NPD4625	Phase 3
0.716	Intermediate Similarity	NPD4357	Discontinued
0.7152	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD2354	Approved
0.7143	Intermediate Similarity	NPD2296	Approved
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7133	Intermediate Similarity	NPD4749	Approved
0.7123	Intermediate Similarity	NPD5536	Phase 2
0.712	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5711	Approved
0.7093	Intermediate Similarity	NPD5710	Approved
0.7089	Intermediate Similarity	NPD7033	Discontinued
0.7075	Intermediate Similarity	NPD9545	Approved
0.7066	Intermediate Similarity	NPD6386	Approved
0.7066	Intermediate Similarity	NPD6385	Approved
0.7063	Intermediate Similarity	NPD228	Approved
0.7059	Intermediate Similarity	NPD3018	Phase 2
0.7056	Intermediate Similarity	NPD8434	Phase 2
0.7055	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD9493	Approved
0.7051	Intermediate Similarity	NPD1558	Phase 1
0.7051	Intermediate Similarity	NPD4307	Phase 2
0.7048	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5404	Approved
0.7044	Intermediate Similarity	NPD5405	Approved
0.7044	Intermediate Similarity	NPD5406	Approved
0.7044	Intermediate Similarity	NPD5408	Approved
0.7039	Intermediate Similarity	NPD3266	Approved
0.7039	Intermediate Similarity	NPD3267	Approved
0.7039	Intermediate Similarity	NPD1164	Approved
0.7032	Intermediate Similarity	NPD6798	Discontinued
0.7024	Intermediate Similarity	NPD6844	Discontinued
0.7019	Intermediate Similarity	NPD2654	Approved
0.7012	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2403	Approved
0.7011	Intermediate Similarity	NPD4363	Phase 3
0.7011	Intermediate Similarity	NPD4360	Phase 2
0.7005	Intermediate Similarity	NPD6777	Approved
0.7005	Intermediate Similarity	NPD6779	Approved
0.7005	Intermediate Similarity	NPD6776	Approved
0.7005	Intermediate Similarity	NPD6781	Approved
0.7005	Intermediate Similarity	NPD6782	Approved
0.7005	Intermediate Similarity	NPD6780	Approved
0.7005	Intermediate Similarity	NPD6778	Approved
0.6979	Remote Similarity	NPD8151	Discontinued
0.6966	Remote Similarity	NPD1241	Discontinued
0.6964	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7584	Approved
0.6961	Remote Similarity	NPD8150	Discontinued
0.6954	Remote Similarity	NPD1481	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