NPASS Compound

Structure

NPC179183 OpenBabel07101718302D 21 23 0 0 0 0 0 0 0 0999 V2000 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 1.7321 -2.0000 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 -1.7321 -2.0000 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 -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 -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 -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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 7 2 0 0 0 0 3 9 1 0 0 0 0 4 7 1 0 0 0 0 4 13 2 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 14 2 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 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 15 18 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.06
Volume:	276.613
LogP:	2.52
LogD:	2.589
LogS:	-3.4
# 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:	2.229
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.875
MDCK Permeability:	1.2982348380319308e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.948
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.268

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	87.47954559326172%
Volume Distribution (VD):	0.901
Pgp-substrate:	16.229707717895508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.949
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.17
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.439
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.575
CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.43
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	7.684
Half-life (T1/2):	0.828

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.543
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.859
Carcinogencity:	0.024
Eye Corrosion:	0.049
Eye Irritation:	0.939
Respiratory Toxicity:	0.426

Download Data

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

Natural Product: NPC179183

Natural Product ID:	NPC179183
*Common Name:**	Laxanthone-I
IUPAC Name:	1,3-dihydroxy-6,7-dimethoxyxanthen-9-one
Synonyms:
Standard InCHIKey:	LOZIYAQUVDQPDB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O6/c1-19-11-5-8-10(6-12(11)20-2)21-13-4-7(16)3-9(17)14(13)15(8)18/h3-6,16-17H,1-2H3
SMILES:	COc1cc2c(cc1OC)oc1cc(cc(c1c2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357571
PubChem CID:	69866203
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
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	200000.0	nM	PMID[573989]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	122800.0	nM	PMID[573989]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	200000.0	nM	PMID[573989]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30000.0	nM	PMID[573988]

☑ 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 NPC179183 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	453
0.1-0.2	2019
0.2-0.3	5062
0.3-0.4	11582
0.4-0.5	5695
0.5-0.6	3886
0.6-0.7	5071
0.7-0.8	4748
0.8-0.85	2154
0.85-0.9	1261
0.9-0.95	565
0.95-1	201

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC149614
0.9862	High Similarity	NPC101996
0.9795	High Similarity	NPC167091
0.9795	High Similarity	NPC271779
0.9795	High Similarity	NPC206238
0.9795	High Similarity	NPC88645
0.9795	High Similarity	NPC292214
0.9793	High Similarity	NPC117579
0.9793	High Similarity	NPC171010
0.9726	High Similarity	NPC180234
0.9726	High Similarity	NPC120537
0.9726	High Similarity	NPC199100
0.9726	High Similarity	NPC39007
0.9726	High Similarity	NPC161277
0.966	High Similarity	NPC280937
0.966	High Similarity	NPC472915
0.9658	High Similarity	NPC251110
0.9653	High Similarity	NPC46941
0.9597	High Similarity	NPC36852
0.9597	High Similarity	NPC181960
0.9597	High Similarity	NPC99597
0.9597	High Similarity	NPC210084
0.9597	High Similarity	NPC262286
0.9595	High Similarity	NPC37392
0.9595	High Similarity	NPC472909
0.9595	High Similarity	NPC2928
0.9589	High Similarity	NPC306821
0.9589	High Similarity	NPC29231
0.9589	High Similarity	NPC248102
0.9589	High Similarity	NPC62042
0.9589	High Similarity	NPC61620
0.9586	High Similarity	NPC194856
0.9583	High Similarity	NPC231013
0.953	High Similarity	NPC255106
0.953	High Similarity	NPC138243
0.953	High Similarity	NPC472916
0.953	High Similarity	NPC235165
0.9524	High Similarity	NPC308451
0.9524	High Similarity	NPC226973
0.9524	High Similarity	NPC208043
0.9521	High Similarity	NPC294502
0.9521	High Similarity	NPC328119
0.9521	High Similarity	NPC200221
0.9517	High Similarity	NPC207729
0.9514	High Similarity	NPC472917
0.9467	High Similarity	NPC222814
0.9467	High Similarity	NPC162869
0.9467	High Similarity	NPC156057
0.9467	High Similarity	NPC300727
0.9467	High Similarity	NPC245758
0.9467	High Similarity	NPC472911
0.9467	High Similarity	NPC474208
0.9467	High Similarity	NPC165977
0.9467	High Similarity	NPC474836
0.9467	High Similarity	NPC472910
0.9467	High Similarity	NPC78225
0.9467	High Similarity	NPC217677
0.9467	High Similarity	NPC475267
0.9467	High Similarity	NPC469584
0.9467	High Similarity	NPC472913
0.9467	High Similarity	NPC241904
0.9467	High Similarity	NPC48208
0.9467	High Similarity	NPC96167
0.9467	High Similarity	NPC472914
0.9467	High Similarity	NPC476981
0.9463	High Similarity	NPC255807
0.9463	High Similarity	NPC208197
0.9463	High Similarity	NPC20830
0.9463	High Similarity	NPC31018
0.9463	High Similarity	NPC113906
0.9463	High Similarity	NPC256612
0.9459	High Similarity	NPC241498
0.9459	High Similarity	NPC120163
0.9459	High Similarity	NPC83508
0.9459	High Similarity	NPC198826
0.9459	High Similarity	NPC275836
0.9459	High Similarity	NPC301323
0.9459	High Similarity	NPC212678
0.9459	High Similarity	NPC293183
0.9459	High Similarity	NPC162313
0.9459	High Similarity	NPC131624
0.9459	High Similarity	NPC57030
0.9459	High Similarity	NPC25270
0.9459	High Similarity	NPC222830
0.9459	High Similarity	NPC156222
0.9459	High Similarity	NPC239128
0.9459	High Similarity	NPC187498
0.9459	High Similarity	NPC71334
0.9459	High Similarity	NPC301123
0.9459	High Similarity	NPC256283
0.9459	High Similarity	NPC188203
0.9459	High Similarity	NPC100887
0.9459	High Similarity	NPC275722
0.9456	High Similarity	NPC45873
0.9456	High Similarity	NPC239363
0.9456	High Similarity	NPC156953
0.9456	High Similarity	NPC338131
0.9452	High Similarity	NPC10304
0.9452	High Similarity	NPC196277
0.9452	High Similarity	NPC276930
0.9452	High Similarity	NPC43669
0.9452	High Similarity	NPC272721
0.9452	High Similarity	NPC287395
0.9452	High Similarity	NPC183655
0.9452	High Similarity	NPC63256
0.9408	High Similarity	NPC308992
0.9404	High Similarity	NPC476242
0.9404	High Similarity	NPC152904
0.94	High Similarity	NPC68093
0.94	High Similarity	NPC274730
0.94	High Similarity	NPC45131
0.94	High Similarity	NPC191146
0.9396	High Similarity	NPC274327
0.9396	High Similarity	NPC183878
0.9396	High Similarity	NPC231018
0.9396	High Similarity	NPC86485
0.9396	High Similarity	NPC176775
0.9396	High Similarity	NPC250822
0.9396	High Similarity	NPC276409
0.9396	High Similarity	NPC47781
0.9396	High Similarity	NPC255350
0.9396	High Similarity	NPC69394
0.9396	High Similarity	NPC22519
0.9396	High Similarity	NPC75279
0.9396	High Similarity	NPC145379
0.9396	High Similarity	NPC160951
0.9392	High Similarity	NPC19980
0.9392	High Similarity	NPC202157
0.9392	High Similarity	NPC31363
0.9392	High Similarity	NPC262623
0.9392	High Similarity	NPC45291
0.9392	High Similarity	NPC204515
0.9388	High Similarity	NPC216318
0.9388	High Similarity	NPC296197
0.9388	High Similarity	NPC259713
0.9388	High Similarity	NPC17286
0.9384	High Similarity	NPC77378
0.9384	High Similarity	NPC61871
0.9384	High Similarity	NPC119660
0.9384	High Similarity	NPC33265
0.9384	High Similarity	NPC12200
0.9384	High Similarity	NPC55557
0.9384	High Similarity	NPC62536
0.9384	High Similarity	NPC30647
0.9384	High Similarity	NPC93034
0.9375	High Similarity	NPC169479
0.9375	High Similarity	NPC159855
0.9346	High Similarity	NPC472448
0.9346	High Similarity	NPC83922
0.9342	High Similarity	NPC475886
0.9342	High Similarity	NPC263449
0.9342	High Similarity	NPC228785
0.9342	High Similarity	NPC476980
0.9342	High Similarity	NPC474287
0.9342	High Similarity	NPC14353
0.9342	High Similarity	NPC56085
0.9338	High Similarity	NPC299520
0.9338	High Similarity	NPC223787
0.9338	High Similarity	NPC129684
0.9333	High Similarity	NPC92659
0.9333	High Similarity	NPC44079
0.9333	High Similarity	NPC227325
0.9333	High Similarity	NPC167815
0.9333	High Similarity	NPC26227
0.9333	High Similarity	NPC189960
0.9333	High Similarity	NPC32557
0.9333	High Similarity	NPC168247
0.9333	High Similarity	NPC163780
0.9333	High Similarity	NPC117992
0.9333	High Similarity	NPC50715
0.9333	High Similarity	NPC230149
0.9333	High Similarity	NPC2476
0.9333	High Similarity	NPC196439
0.9333	High Similarity	NPC201136
0.9333	High Similarity	NPC152951
0.9333	High Similarity	NPC4455
0.9333	High Similarity	NPC57674
0.9333	High Similarity	NPC138360
0.9333	High Similarity	NPC128863
0.9333	High Similarity	NPC183597
0.9333	High Similarity	NPC201451
0.9333	High Similarity	NPC213622
0.9333	High Similarity	NPC280339
0.9333	High Similarity	NPC146165
0.9329	High Similarity	NPC302950
0.9329	High Similarity	NPC100971
0.9329	High Similarity	NPC477231
0.9329	High Similarity	NPC291802
0.9329	High Similarity	NPC269451
0.9329	High Similarity	NPC219582
0.9329	High Similarity	NPC100263
0.9329	High Similarity	NPC121522
0.9329	High Similarity	NPC216769
0.9329	High Similarity	NPC236637
0.9329	High Similarity	NPC257648
0.9329	High Similarity	NPC131266
0.9329	High Similarity	NPC142540
0.9329	High Similarity	NPC60972
0.9329	High Similarity	NPC35763
0.9329	High Similarity	NPC39732

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 NPC179183 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	433
0.1-0.2	1010
0.2-0.3	1873
0.3-0.4	2655
0.4-0.5	1713
0.5-0.6	948
0.6-0.7	359
0.7-0.8	105
0.8-0.85	34
0.85-0.9	13
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9396	High Similarity	NPD2801	Approved
0.9329	High Similarity	NPD1934	Approved
0.9048	High Similarity	NPD1511	Approved
0.9013	High Similarity	NPD2393	Clinical (unspecified phase)
0.8926	High Similarity	NPD1512	Approved
0.8896	High Similarity	NPD3882	Suspended
0.8846	High Similarity	NPD5494	Approved
0.8836	High Similarity	NPD1549	Phase 2
0.8767	High Similarity	NPD1552	Clinical (unspecified phase)
0.8767	High Similarity	NPD1550	Clinical (unspecified phase)
0.8742	High Similarity	NPD6167	Clinical (unspecified phase)
0.8742	High Similarity	NPD6166	Phase 2
0.8742	High Similarity	NPD6168	Clinical (unspecified phase)
0.8654	High Similarity	NPD4868	Clinical (unspecified phase)
0.8634	High Similarity	NPD3818	Discontinued
0.863	High Similarity	NPD1510	Phase 2
0.8611	High Similarity	NPD1240	Approved
0.8609	High Similarity	NPD4378	Clinical (unspecified phase)
0.859	High Similarity	NPD3817	Phase 2
0.8528	High Similarity	NPD7074	Phase 3
0.8526	High Similarity	NPD1465	Phase 2
0.8493	Intermediate Similarity	NPD1607	Approved
0.8485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7054	Approved
0.8452	Intermediate Similarity	NPD4380	Phase 2
0.8438	Intermediate Similarity	NPD1247	Approved
0.8415	Intermediate Similarity	NPD7472	Approved
0.8385	Intermediate Similarity	NPD6232	Discontinued
0.8365	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7075	Discontinued
0.8356	Intermediate Similarity	NPD943	Approved
0.8354	Intermediate Similarity	NPD5844	Phase 1
0.8344	Intermediate Similarity	NPD7473	Discontinued
0.8322	Intermediate Similarity	NPD2796	Approved
0.8291	Intermediate Similarity	NPD7819	Suspended
0.8291	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7808	Phase 3
0.8253	Intermediate Similarity	NPD6797	Phase 2
0.8247	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7251	Discontinued
0.8182	Intermediate Similarity	NPD6799	Approved
0.8176	Intermediate Similarity	NPD447	Suspended
0.8165	Intermediate Similarity	NPD7411	Suspended
0.8144	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5402	Approved
0.8125	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD3926	Phase 2
0.8098	Intermediate Similarity	NPD6959	Discontinued
0.8086	Intermediate Similarity	NPD919	Approved
0.8082	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2935	Discontinued
0.8054	Intermediate Similarity	NPD230	Phase 1
0.8039	Intermediate Similarity	NPD2800	Approved
0.8025	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD3750	Approved
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1551	Phase 2
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6559	Discontinued
0.7844	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1933	Approved
0.7806	Intermediate Similarity	NPD1243	Approved
0.7799	Intermediate Similarity	NPD920	Approved
0.7792	Intermediate Similarity	NPD2344	Approved
0.7785	Intermediate Similarity	NPD2532	Approved
0.7785	Intermediate Similarity	NPD2534	Approved
0.7785	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7768	Phase 2
0.7727	Intermediate Similarity	NPD6100	Approved
0.7727	Intermediate Similarity	NPD6099	Approved
0.7702	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5403	Approved
0.768	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2346	Discontinued
0.7673	Intermediate Similarity	NPD5401	Approved
0.7673	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD3748	Approved
0.7651	Intermediate Similarity	NPD9494	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7643	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1653	Approved
0.7635	Intermediate Similarity	NPD1203	Approved
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7616	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2309	Approved
0.7571	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3027	Phase 3
0.7548	Intermediate Similarity	NPD2799	Discontinued
0.7547	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6651	Approved
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1610	Phase 2
0.7456	Intermediate Similarity	NPD7199	Phase 2
0.7455	Intermediate Similarity	NPD37	Approved
0.744	Intermediate Similarity	NPD6234	Discontinued
0.7432	Intermediate Similarity	NPD9717	Approved
0.7432	Intermediate Similarity	NPD9269	Phase 2
0.7425	Intermediate Similarity	NPD4965	Approved
0.7425	Intermediate Similarity	NPD4967	Phase 2
0.7425	Intermediate Similarity	NPD4966	Approved
0.7412	Intermediate Similarity	NPD3787	Discontinued
0.7401	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD9268	Approved
0.7391	Intermediate Similarity	NPD7390	Discontinued
0.7383	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6190	Approved
0.7368	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD5242	Approved
0.7365	Intermediate Similarity	NPD5353	Approved
0.7355	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6844	Discontinued
0.733	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1548	Phase 1
0.7315	Intermediate Similarity	NPD1608	Approved
0.731	Intermediate Similarity	NPD5710	Approved
0.731	Intermediate Similarity	NPD5711	Approved
0.7285	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD411	Approved
0.7255	Intermediate Similarity	NPD6832	Phase 2
0.7248	Intermediate Similarity	NPD422	Phase 1
0.7241	Intermediate Similarity	NPD7228	Approved
0.7237	Intermediate Similarity	NPD2798	Approved
0.7225	Intermediate Similarity	NPD2403	Approved
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7204	Intermediate Similarity	NPD6776	Approved
0.7204	Intermediate Similarity	NPD6777	Approved
0.7204	Intermediate Similarity	NPD6782	Approved
0.7204	Intermediate Similarity	NPD6778	Approved
0.7204	Intermediate Similarity	NPD6781	Approved
0.7204	Intermediate Similarity	NPD6780	Approved
0.7204	Intermediate Similarity	NPD6779	Approved
0.7191	Intermediate Similarity	NPD8312	Approved
0.7191	Intermediate Similarity	NPD8313	Approved
0.719	Intermediate Similarity	NPD2861	Phase 2
0.7186	Intermediate Similarity	NPD6385	Approved
0.7186	Intermediate Similarity	NPD6386	Approved
0.7178	Intermediate Similarity	NPD4357	Discontinued
0.7175	Intermediate Similarity	NPD7685	Pre-registration
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.7161	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD4749	Approved
0.7143	Intermediate Similarity	NPD2654	Approved
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7135	Intermediate Similarity	NPD7549	Discontinued
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1201	Approved
0.7125	Intermediate Similarity	NPD1471	Phase 3
0.712	Intermediate Similarity	NPD4363	Phase 3
0.712	Intermediate Similarity	NPD4360	Phase 2
0.7114	Intermediate Similarity	NPD17	Approved
0.7107	Intermediate Similarity	NPD7033	Discontinued
0.7097	Intermediate Similarity	NPD4625	Phase 3
0.7095	Intermediate Similarity	NPD9545	Approved
0.709	Intermediate Similarity	NPD7435	Discontinued
0.709	Intermediate Similarity	NPD7697	Approved
0.709	Intermediate Similarity	NPD7696	Phase 3
0.709	Intermediate Similarity	NPD7698	Approved
0.7088	Intermediate Similarity	NPD4287	Approved
0.7086	Intermediate Similarity	NPD1481	Phase 2
0.7083	Intermediate Similarity	NPD8151	Discontinued
0.7083	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3018	Phase 2
0.7075	Intermediate Similarity	NPD9493	Approved
0.7072	Intermediate Similarity	NPD8150	Discontinued
0.7059	Intermediate Similarity	NPD4288	Approved
0.7059	Intermediate Similarity	NPD2797	Approved
0.7059	Intermediate Similarity	NPD2296	Approved
0.7053	Intermediate Similarity	NPD7871	Phase 2
0.7053	Intermediate Similarity	NPD7870	Phase 2
0.7051	Intermediate Similarity	NPD3764	Approved
0.7043	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2899	Discontinued
0.702	Intermediate Similarity	NPD1535	Discovery
0.7018	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1019	Discontinued
0.7011	Intermediate Similarity	NPD7229	Phase 3
0.7006	Intermediate Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD3225	Approved
0.6988	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1241	Discontinued
0.6979	Remote Similarity	NPD7584	Approved
0.6974	Remote Similarity	NPD3972	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