NPASS Compound

Structure

NPC167091 OpenBabel07101718202D 21 23 0 0 0 0 0 0 0 0999 V2000 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 18 2 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.06
Volume:	276.613
LogP:	2.533
LogD:	2.46
LogS:	-3.247
# Rotatable Bonds:	2
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	2.432
Fsp3:	0.133
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:	-4.833
MDCK Permeability:	1.7244721675524488e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.134
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	89.5666275024414%
Volume Distribution (VD):	0.807
Pgp-substrate:	16.682477951049805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.249
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.526
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.691
CYP2D6-substrate:	0.695
CYP3A4-inhibitor:	0.52
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	4.786
Half-life (T1/2):	0.802

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.614
Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.582
Skin Sensitization:	0.863
Carcinogencity:	0.041
Eye Corrosion:	0.049
Eye Irritation:	0.96
Respiratory Toxicity:	0.18

Download Data

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

Natural Product: NPC167091

Natural Product ID:	NPC167091
*Common Name:**	3,6-Dihydroxy-1,2-Dimethoxyxanthone
IUPAC Name:	3,6-dihydroxy-1,2-dimethoxyxanthen-9-one
Synonyms:
Standard InCHIKey:	KREQTBSQJOEUKA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O6/c1-19-14-9(17)6-11-12(15(14)20-2)13(18)8-4-3-7(16)5-10(8)21-11/h3-6,16-17H,1-2H3
SMILES:	COc1c(cc2c(c(=O)c3ccc(cc3o2)O)c1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2029864
PubChem CID:	16105269
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
NPO32798	polygala karensium	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22552195]

☑ 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
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	>	100.0	ug.mL-1	PMID[536587]
NPT2	Others	Unspecified		Ratio IC50	=	243.0	n.a.	PMID[536587]

☑ 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 NPC167091 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	462
0.1-0.2	1978
0.2-0.3	5108
0.3-0.4	11555
0.4-0.5	5658
0.5-0.6	3782
0.6-0.7	5099
0.7-0.8	4798
0.8-0.85	2113
0.85-0.9	1191
0.9-0.95	667
0.95-1	286

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC292214
1.0	High Similarity	NPC88645
1.0	High Similarity	NPC271779
1.0	High Similarity	NPC206238
0.9932	High Similarity	NPC120537
0.9932	High Similarity	NPC180234
0.9932	High Similarity	NPC101996
0.9932	High Similarity	NPC199100
0.9932	High Similarity	NPC39007
0.9932	High Similarity	NPC161277
0.9863	High Similarity	NPC171010
0.9863	High Similarity	NPC149614
0.9863	High Similarity	NPC251110
0.9799	High Similarity	NPC99597
0.9799	High Similarity	NPC210084
0.9797	High Similarity	NPC2928
0.9795	High Similarity	NPC179183
0.9795	High Similarity	NPC61620
0.9795	High Similarity	NPC62042
0.9795	High Similarity	NPC248102
0.9795	High Similarity	NPC29231
0.9732	High Similarity	NPC255106
0.9732	High Similarity	NPC472916
0.9732	High Similarity	NPC235165
0.9728	High Similarity	NPC117579
0.9726	High Similarity	NPC294502
0.9726	High Similarity	NPC200221
0.9667	High Similarity	NPC472914
0.9667	High Similarity	NPC262286
0.9667	High Similarity	NPC48208
0.9667	High Similarity	NPC96167
0.9667	High Similarity	NPC472913
0.9667	High Similarity	NPC474836
0.9667	High Similarity	NPC472911
0.9667	High Similarity	NPC472910
0.9667	High Similarity	NPC245758
0.9667	High Similarity	NPC36852
0.9667	High Similarity	NPC474208
0.9667	High Similarity	NPC222814
0.9667	High Similarity	NPC162869
0.9667	High Similarity	NPC475267
0.9667	High Similarity	NPC78225
0.9667	High Similarity	NPC156057
0.9664	High Similarity	NPC256612
0.9664	High Similarity	NPC20830
0.9662	High Similarity	NPC83508
0.9662	High Similarity	NPC275722
0.9662	High Similarity	NPC275836
0.9662	High Similarity	NPC120163
0.9662	High Similarity	NPC301323
0.9662	High Similarity	NPC25270
0.9662	High Similarity	NPC57030
0.9662	High Similarity	NPC156222
0.9662	High Similarity	NPC188203
0.9662	High Similarity	NPC100887
0.9662	High Similarity	NPC256283
0.9662	High Similarity	NPC293183
0.9662	High Similarity	NPC222830
0.9662	High Similarity	NPC239128
0.9662	High Similarity	NPC131624
0.9662	High Similarity	NPC241498
0.9662	High Similarity	NPC162313
0.9662	High Similarity	NPC198826
0.9662	High Similarity	NPC187498
0.9662	High Similarity	NPC212678
0.9662	High Similarity	NPC71334
0.966	High Similarity	NPC45873
0.9658	High Similarity	NPC272721
0.9658	High Similarity	NPC276930
0.9658	High Similarity	NPC196277
0.9658	High Similarity	NPC194856
0.9658	High Similarity	NPC43669
0.9658	High Similarity	NPC287395
0.9658	High Similarity	NPC183655
0.9605	High Similarity	NPC308992
0.96	High Similarity	NPC68093
0.96	High Similarity	NPC191146
0.96	High Similarity	NPC138243
0.9597	High Similarity	NPC183878
0.9597	High Similarity	NPC145379
0.9597	High Similarity	NPC160951
0.9597	High Similarity	NPC274327
0.9597	High Similarity	NPC255350
0.9597	High Similarity	NPC176775
0.9597	High Similarity	NPC472915
0.9597	High Similarity	NPC22519
0.9597	High Similarity	NPC231018
0.9597	High Similarity	NPC47781
0.9597	High Similarity	NPC69394
0.9595	High Similarity	NPC204515
0.9595	High Similarity	NPC31363
0.9592	High Similarity	NPC296197
0.9592	High Similarity	NPC17286
0.9592	High Similarity	NPC259713
0.9592	High Similarity	NPC216318
0.9589	High Similarity	NPC207729
0.9589	High Similarity	NPC46941
0.9589	High Similarity	NPC77378
0.9542	High Similarity	NPC472448
0.9542	High Similarity	NPC83922
0.9539	High Similarity	NPC476980
0.9539	High Similarity	NPC263449
0.9536	High Similarity	NPC299520
0.9536	High Similarity	NPC241904
0.9536	High Similarity	NPC181960
0.9536	High Similarity	NPC469584
0.9536	High Similarity	NPC129684
0.9536	High Similarity	NPC300727
0.9533	High Similarity	NPC113906
0.9533	High Similarity	NPC128863
0.9533	High Similarity	NPC44079
0.9533	High Similarity	NPC168247
0.9533	High Similarity	NPC117992
0.9533	High Similarity	NPC201136
0.9533	High Similarity	NPC146165
0.9533	High Similarity	NPC213622
0.9533	High Similarity	NPC196439
0.9533	High Similarity	NPC167815
0.9533	High Similarity	NPC92659
0.9533	High Similarity	NPC208197
0.9533	High Similarity	NPC57674
0.9533	High Similarity	NPC152951
0.9533	High Similarity	NPC2476
0.9533	High Similarity	NPC227325
0.9533	High Similarity	NPC138360
0.9533	High Similarity	NPC280339
0.9533	High Similarity	NPC4455
0.9533	High Similarity	NPC472909
0.9533	High Similarity	NPC201451
0.9533	High Similarity	NPC26227
0.9533	High Similarity	NPC37392
0.9533	High Similarity	NPC183597
0.9533	High Similarity	NPC163780
0.9533	High Similarity	NPC50715
0.9533	High Similarity	NPC230149
0.953	High Similarity	NPC39732
0.953	High Similarity	NPC181209
0.953	High Similarity	NPC35763
0.953	High Similarity	NPC131266
0.953	High Similarity	NPC257648
0.953	High Similarity	NPC245382
0.953	High Similarity	NPC142540
0.953	High Similarity	NPC216769
0.953	High Similarity	NPC219582
0.953	High Similarity	NPC100971
0.953	High Similarity	NPC302950
0.953	High Similarity	NPC121522
0.953	High Similarity	NPC236637
0.953	High Similarity	NPC209487
0.953	High Similarity	NPC291802
0.953	High Similarity	NPC100263
0.953	High Similarity	NPC477231
0.953	High Similarity	NPC269451
0.953	High Similarity	NPC60972
0.9527	High Similarity	NPC184136
0.9527	High Similarity	NPC306821
0.9524	High Similarity	NPC12367
0.9524	High Similarity	NPC118726
0.9521	High Similarity	NPC209278
0.9521	High Similarity	NPC231013
0.9477	High Similarity	NPC258331
0.9477	High Similarity	NPC162668
0.9477	High Similarity	NPC167678
0.9477	High Similarity	NPC29876
0.9477	High Similarity	NPC266314
0.9474	High Similarity	NPC95936
0.9474	High Similarity	NPC16935
0.9474	High Similarity	NPC476242
0.9474	High Similarity	NPC152904
0.9474	High Similarity	NPC250214
0.9474	High Similarity	NPC55738
0.947	High Similarity	NPC49824
0.947	High Similarity	NPC98661
0.947	High Similarity	NPC474638
0.947	High Similarity	NPC201837
0.947	High Similarity	NPC266960
0.947	High Similarity	NPC245546
0.947	High Similarity	NPC274730
0.947	High Similarity	NPC43243
0.947	High Similarity	NPC247017
0.9467	High Similarity	NPC250822
0.9467	High Similarity	NPC49402
0.9467	High Similarity	NPC18727
0.9467	High Similarity	NPC33051
0.9467	High Similarity	NPC75279
0.9467	High Similarity	NPC227337
0.9467	High Similarity	NPC469550
0.9467	High Similarity	NPC70433
0.9467	High Similarity	NPC273462
0.9467	High Similarity	NPC280937
0.9467	High Similarity	NPC276409
0.9467	High Similarity	NPC124714
0.9463	High Similarity	NPC45291
0.9463	High Similarity	NPC202157
0.9463	High Similarity	NPC19980
0.9463	High Similarity	NPC226973
0.9463	High Similarity	NPC308451
0.9463	High Similarity	NPC225731
0.9463	High Similarity	NPC208043
0.9459	High Similarity	NPC183950

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 NPC167091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	443
0.1-0.2	983
0.2-0.3	1848
0.3-0.4	2670
0.4-0.5	1719
0.5-0.6	963
0.6-0.7	360
0.7-0.8	110
0.8-0.85	29
0.85-0.9	17
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9597	High Similarity	NPD2801	Approved
0.953	High Similarity	NPD1934	Approved
0.9252	High Similarity	NPD1511	Approved
0.9211	High Similarity	NPD2393	Clinical (unspecified phase)
0.9128	High Similarity	NPD1512	Approved
0.9091	High Similarity	NPD3882	Suspended
0.8931	High Similarity	NPD6166	Phase 2
0.8931	High Similarity	NPD6167	Clinical (unspecified phase)
0.8931	High Similarity	NPD6168	Clinical (unspecified phase)
0.882	High Similarity	NPD3818	Discontinued
0.8797	High Similarity	NPD5494	Approved
0.8784	High Similarity	NPD1549	Phase 2
0.8726	High Similarity	NPD4868	Clinical (unspecified phase)
0.8716	High Similarity	NPD1552	Clinical (unspecified phase)
0.8716	High Similarity	NPD1550	Clinical (unspecified phase)
0.8712	High Similarity	NPD7074	Phase 3
0.8667	High Similarity	NPD4338	Clinical (unspecified phase)
0.8662	High Similarity	NPD3817	Phase 2
0.865	High Similarity	NPD7054	Approved
0.8599	High Similarity	NPD1465	Phase 2
0.8598	High Similarity	NPD7472	Approved
0.8581	High Similarity	NPD1510	Phase 2
0.8562	High Similarity	NPD943	Approved
0.8562	High Similarity	NPD1240	Approved
0.8562	High Similarity	NPD4378	Clinical (unspecified phase)
0.8526	High Similarity	NPD4380	Phase 2
0.8446	Intermediate Similarity	NPD1607	Approved
0.8438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7075	Discontinued
0.8434	Intermediate Similarity	NPD6797	Phase 2
0.8395	Intermediate Similarity	NPD1247	Approved
0.8383	Intermediate Similarity	NPD7251	Discontinued
0.8365	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD7808	Phase 3
0.8313	Intermediate Similarity	NPD5844	Phase 1
0.8303	Intermediate Similarity	NPD7473	Discontinued
0.8288	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD2796	Approved
0.8258	Intermediate Similarity	NPD6799	Approved
0.825	Intermediate Similarity	NPD7819	Suspended
0.8219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD5402	Approved
0.8188	Intermediate Similarity	NPD1613	Approved
0.8188	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD230	Phase 1
0.8133	Intermediate Similarity	NPD447	Suspended
0.8125	Intermediate Similarity	NPD7411	Suspended
0.8086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6801	Discontinued
0.8072	Intermediate Similarity	NPD3926	Phase 2
0.8063	Intermediate Similarity	NPD6599	Discontinued
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD919	Approved
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.7988	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3749	Approved
0.7974	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD6559	Discontinued
0.7952	Intermediate Similarity	NPD6959	Discontinued
0.7949	Intermediate Similarity	NPD3750	Approved
0.7922	Intermediate Similarity	NPD1551	Phase 2
0.7885	Intermediate Similarity	NPD2800	Approved
0.7875	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD9494	Approved
0.7826	Intermediate Similarity	NPD1653	Approved
0.7811	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1933	Approved
0.7764	Intermediate Similarity	NPD5403	Approved
0.7764	Intermediate Similarity	NPD920	Approved
0.7756	Intermediate Similarity	NPD2344	Approved
0.775	Intermediate Similarity	NPD5401	Approved
0.7748	Intermediate Similarity	NPD3027	Phase 3
0.7742	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3751	Discontinued
0.7711	Intermediate Similarity	NPD7768	Phase 2
0.7669	Intermediate Similarity	NPD3226	Approved
0.7658	Intermediate Similarity	NPD1243	Approved
0.7658	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2346	Discontinued
0.764	Intermediate Similarity	NPD2533	Approved
0.764	Intermediate Similarity	NPD2532	Approved
0.764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2534	Approved
0.7628	Intermediate Similarity	NPD3748	Approved
0.761	Intermediate Similarity	NPD4628	Phase 3
0.761	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1203	Approved
0.7584	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2313	Discontinued
0.758	Intermediate Similarity	NPD6099	Approved
0.758	Intermediate Similarity	NPD6100	Approved
0.7578	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2309	Approved
0.7562	Intermediate Similarity	NPD6190	Approved
0.7556	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7517	Intermediate Similarity	NPD9269	Phase 2
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7471	Intermediate Similarity	NPD7286	Phase 2
0.745	Intermediate Similarity	NPD1610	Phase 2
0.7442	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD9717	Approved
0.7391	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6651	Approved
0.7345	Intermediate Similarity	NPD7685	Pre-registration
0.7341	Intermediate Similarity	NPD5242	Approved
0.7338	Intermediate Similarity	NPD4908	Phase 1
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6844	Discontinued
0.7321	Intermediate Similarity	NPD37	Approved
0.7314	Intermediate Similarity	NPD7228	Approved
0.7303	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1548	Phase 1
0.7294	Intermediate Similarity	NPD4967	Phase 2
0.7294	Intermediate Similarity	NPD4966	Approved
0.7294	Intermediate Similarity	NPD4965	Approved
0.7285	Intermediate Similarity	NPD1608	Approved
0.7273	Intermediate Similarity	NPD6778	Approved
0.7273	Intermediate Similarity	NPD6779	Approved
0.7273	Intermediate Similarity	NPD6780	Approved
0.7273	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD6781	Approved
0.7273	Intermediate Similarity	NPD6777	Approved
0.7273	Intermediate Similarity	NPD6776	Approved
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7256	Intermediate Similarity	NPD7390	Discontinued
0.7255	Intermediate Similarity	NPD1470	Approved
0.7248	Intermediate Similarity	NPD9268	Approved
0.7244	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD411	Approved
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7235	Intermediate Similarity	NPD5353	Approved
0.7226	Intermediate Similarity	NPD6832	Phase 2
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7208	Intermediate Similarity	NPD2798	Approved
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7184	Intermediate Similarity	NPD5711	Approved
0.7184	Intermediate Similarity	NPD5710	Approved
0.7172	Intermediate Similarity	NPD2899	Discontinued
0.7161	Intermediate Similarity	NPD2861	Phase 2
0.716	Intermediate Similarity	NPD6386	Approved
0.716	Intermediate Similarity	NPD6385	Approved
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7152	Intermediate Similarity	NPD4357	Discontinued
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7134	Intermediate Similarity	NPD3268	Approved
0.7114	Intermediate Similarity	NPD5536	Phase 2
0.7112	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7549	Discontinued
0.7108	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1201	Approved
0.7102	Intermediate Similarity	NPD2403	Approved
0.7099	Intermediate Similarity	NPD1471	Phase 3
0.7097	Intermediate Similarity	NPD4360	Phase 2
0.7097	Intermediate Similarity	NPD4363	Phase 3
0.7089	Intermediate Similarity	NPD6233	Phase 2
0.7086	Intermediate Similarity	NPD17	Approved
0.7081	Intermediate Similarity	NPD7033	Discontinued
0.707	Intermediate Similarity	NPD4625	Phase 3
0.7068	Intermediate Similarity	NPD7697	Approved
0.7068	Intermediate Similarity	NPD7698	Approved
0.7068	Intermediate Similarity	NPD7696	Phase 3
0.7067	Intermediate Similarity	NPD9545	Approved
0.7065	Intermediate Similarity	NPD4287	Approved
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD1481	Phase 2
0.7059	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD228	Approved
0.7051	Intermediate Similarity	NPD3018	Phase 2
0.7047	Intermediate Similarity	NPD9493	Approved
0.7047	Intermediate Similarity	NPD7584	Approved
0.7035	Intermediate Similarity	NPD2296	Approved
0.7035	Intermediate Similarity	NPD4288	Approved
0.7032	Intermediate Similarity	NPD2797	Approved
0.7031	Intermediate Similarity	NPD7871	Phase 2
0.7031	Intermediate Similarity	NPD7870	Phase 2
0.703	Intermediate Similarity	NPD2354	Approved
0.7025	Intermediate Similarity	NPD3764	Approved
0.7025	Intermediate Similarity	NPD6798	Discontinued
0.7016	Intermediate Similarity	NPD6823	Phase 2
0.7013	Intermediate Similarity	NPD4749	Approved
0.7012	Intermediate Similarity	NPD2654	Approved
0.7012	Intermediate Similarity	NPD1652	Phase 2
0.701	Intermediate Similarity	NPD7701	Phase 2
0.7005	Intermediate Similarity	NPD6535	Approved
0.7005	Intermediate Similarity	NPD6534	Approved

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