NPASS Compound

Structure

NPC198615 OpenBabel07101718232D 31 33 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 -0.0000 1.0000 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 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 -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 4.3301 -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 -0.8660 -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 -2.5981 -0.5000 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 2.5981 -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 -0.0000 -2.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 3.4641 -0.0000 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 14 2 0 0 0 0 7 17 1 0 0 0 0 8 16 2 0 0 0 0 8 18 1 0 0 0 0 9 22 2 0 0 0 0 9 27 1 0 0 0 0 10 23 2 0 0 0 0 10 28 1 0 0 0 0 11 24 2 0 0 0 0 11 29 1 0 0 0 0 12 25 2 0 0 0 0 12 30 1 0 0 0 0 13 19 1 0 0 0 0 13 20 2 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 21 2 0 0 0 0 15 27 1 0 0 0 0 16 31 1 0 0 0 0 17 18 2 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 26 2 0 0 0 0 20 21 1 0 0 0 0 20 31 1 0 0 0 0 21 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.07
Volume:	405.004
LogP:	2.065
LogD:	1.678
LogS:	-5.862
# Rotatable Bonds:	8
TPSA:	135.41
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	2.674
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.938
MDCK Permeability:	2.099993434967473e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.76
20% Bioavailability (F20%):	0.666
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.586
Plasma Protein Binding (PPB):	76.10712432861328%
Volume Distribution (VD):	0.645
Pgp-substrate:	28.09638023376465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.457
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.206
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.723
CYP2C9-substrate:	0.55
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.107
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	1.372
Half-life (T1/2):	0.696

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.001
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.861
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.965
Carcinogencity:	0.102
Eye Corrosion:	0.151
Eye Irritation:	0.576
Respiratory Toxicity:	0.101

Download Data

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

Natural Product: NPC198615

Natural Product ID:	NPC198615
*Common Name:**	(4,6,7-Triacetyloxy-9-Oxoxanthen-3-Yl) Acetate
IUPAC Name:	(4,6,7-triacetyloxy-9-oxoxanthen-3-yl) acetate
Synonyms:
Standard InCHIKey:	SABQRJRRONNVJZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H16O10/c1-9(22)27-15-6-5-13-19(26)14-7-17(28-10(2)23)18(29-11(3)24)8-16(14)31-20(13)21(15)30-12(4)25/h5-8H,1-4H3
SMILES:	CC(=O)Oc1ccc2c(=O)c3cc(c(cc3oc2c1OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477922
PubChem CID:	10365247
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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	Inhibition	<	9.82	%	PMID[453269]

☑ 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 NPC198615 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	501
0.1-0.2	2090
0.2-0.3	5589
0.3-0.4	11131
0.4-0.5	6070
0.5-0.6	4145
0.6-0.7	5850
0.7-0.8	4783
0.8-0.85	1759
0.85-0.9	654
0.9-0.95	109
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC29056
0.9862	High Similarity	NPC474663
0.9792	High Similarity	NPC183236
0.9724	High Similarity	NPC474648
0.9595	High Similarity	NPC186507
0.9521	High Similarity	NPC63256
0.9521	High Similarity	NPC10304
0.94	High Similarity	NPC34725
0.94	High Similarity	NPC241774
0.94	High Similarity	NPC122623
0.94	High Similarity	NPC276059
0.9384	High Similarity	NPC231013
0.9338	High Similarity	NPC257277
0.9324	High Similarity	NPC238366
0.932	High Similarity	NPC85233
0.932	High Similarity	NPC205522
0.9315	High Similarity	NPC165512
0.9272	High Similarity	NPC471746
0.9267	High Similarity	NPC166201
0.9262	High Similarity	NPC177839
0.9252	High Similarity	NPC106461
0.9252	High Similarity	NPC283002
0.9252	High Similarity	NPC14958
0.9252	High Similarity	NPC40818
0.9252	High Similarity	NPC302408
0.9252	High Similarity	NPC215932
0.9252	High Similarity	NPC110639
0.92	High Similarity	NPC474388
0.92	High Similarity	NPC474170
0.92	High Similarity	NPC472535
0.9184	High Similarity	NPC136278
0.9161	High Similarity	NPC108767
0.9133	High Similarity	NPC259058
0.9133	High Similarity	NPC201547
0.9122	High Similarity	NPC216314
0.9122	High Similarity	NPC195919
0.9122	High Similarity	NPC120924
0.9116	High Similarity	NPC23955
0.9116	High Similarity	NPC182842
0.9116	High Similarity	NPC293201
0.9116	High Similarity	NPC113089
0.9103	High Similarity	NPC474350
0.9085	High Similarity	NPC474983
0.9079	High Similarity	NPC475895
0.9079	High Similarity	NPC128961
0.9079	High Similarity	NPC244371
0.9079	High Similarity	NPC472408
0.9079	High Similarity	NPC472915
0.9073	High Similarity	NPC117579
0.9073	High Similarity	NPC149614
0.9067	High Similarity	NPC69752
0.9067	High Similarity	NPC181250
0.906	High Similarity	NPC470511
0.9054	High Similarity	NPC471590
0.9048	High Similarity	NPC70853
0.9048	High Similarity	NPC9966
0.9045	High Similarity	NPC280893
0.9041	High Similarity	NPC58229
0.9032	High Similarity	NPC477164
0.9026	High Similarity	NPC181960
0.9026	High Similarity	NPC258644
0.9026	High Similarity	NPC108456
0.902	High Similarity	NPC37392
0.902	High Similarity	NPC472909
0.9013	High Similarity	NPC39007
0.9013	High Similarity	NPC134677
0.9013	High Similarity	NPC161277
0.9007	High Similarity	NPC248102
0.9007	High Similarity	NPC179183
0.9	High Similarity	NPC476342
0.8981	High Similarity	NPC300984
0.898	High Similarity	NPC29536
0.898	High Similarity	NPC124467
0.898	High Similarity	NPC214919
0.8974	High Similarity	NPC303565
0.8961	High Similarity	NPC472916
0.8961	High Similarity	NPC191146
0.8961	High Similarity	NPC138243
0.8961	High Similarity	NPC180340
0.8961	High Similarity	NPC303255
0.8961	High Similarity	NPC68093
0.8954	High Similarity	NPC271779
0.8954	High Similarity	NPC292214
0.8954	High Similarity	NPC88645
0.8954	High Similarity	NPC280937
0.8954	High Similarity	NPC206238
0.8954	High Similarity	NPC167091
0.8947	High Similarity	NPC171010
0.8947	High Similarity	NPC208043
0.8947	High Similarity	NPC251110
0.8947	High Similarity	NPC308451
0.8947	High Similarity	NPC226973
0.8933	High Similarity	NPC299923
0.8926	High Similarity	NPC213482
0.8924	High Similarity	NPC475369
0.8917	High Similarity	NPC93739
0.891	High Similarity	NPC298093
0.8903	High Similarity	NPC99597
0.8903	High Similarity	NPC476981
0.8903	High Similarity	NPC472911
0.8903	High Similarity	NPC162869
0.8903	High Similarity	NPC474208
0.8903	High Similarity	NPC472914
0.8903	High Similarity	NPC96167
0.8903	High Similarity	NPC156057
0.8903	High Similarity	NPC222814
0.8903	High Similarity	NPC245758
0.8903	High Similarity	NPC19097
0.8903	High Similarity	NPC78225
0.8903	High Similarity	NPC475267
0.8903	High Similarity	NPC472910
0.8903	High Similarity	NPC36852
0.8903	High Similarity	NPC210084
0.8903	High Similarity	NPC472913
0.8903	High Similarity	NPC48208
0.8903	High Similarity	NPC262286
0.8903	High Similarity	NPC474836
0.8896	High Similarity	NPC50715
0.8896	High Similarity	NPC201136
0.8896	High Similarity	NPC2928
0.8896	High Similarity	NPC196439
0.8896	High Similarity	NPC92659
0.8896	High Similarity	NPC227325
0.8896	High Similarity	NPC222185
0.8896	High Similarity	NPC256612
0.8896	High Similarity	NPC208197
0.8896	High Similarity	NPC20830
0.8896	High Similarity	NPC167815
0.8896	High Similarity	NPC2476
0.8896	High Similarity	NPC31018
0.8896	High Similarity	NPC146165
0.8896	High Similarity	NPC138360
0.8896	High Similarity	NPC280339
0.8896	High Similarity	NPC255807
0.8896	High Similarity	NPC183597
0.8896	High Similarity	NPC128863
0.8896	High Similarity	NPC163780
0.8896	High Similarity	NPC4455
0.8889	High Similarity	NPC120537
0.8889	High Similarity	NPC199100
0.8889	High Similarity	NPC475116
0.8889	High Similarity	NPC40033
0.8889	High Similarity	NPC180234
0.8889	High Similarity	NPC292460
0.8889	High Similarity	NPC101996
0.8889	High Similarity	NPC52623
0.8889	High Similarity	NPC142540
0.8889	High Similarity	NPC289968
0.8882	High Similarity	NPC306821
0.8882	High Similarity	NPC61620
0.8875	High Similarity	NPC280493
0.8875	High Similarity	NPC99613
0.8875	High Similarity	NPC49487
0.8867	High Similarity	NPC310259
0.8861	High Similarity	NPC284007
0.8854	High Similarity	NPC167678
0.8854	High Similarity	NPC266314
0.8854	High Similarity	NPC165549
0.8854	High Similarity	NPC29876
0.8851	High Similarity	NPC185607
0.8846	High Similarity	NPC154304
0.8846	High Similarity	NPC238405
0.8846	High Similarity	NPC190487
0.8846	High Similarity	NPC193842
0.8846	High Similarity	NPC104459
0.8846	High Similarity	NPC257914
0.8846	High Similarity	NPC152904
0.8839	High Similarity	NPC255106
0.8839	High Similarity	NPC274730
0.8839	High Similarity	NPC235165
0.8839	High Similarity	NPC178854
0.8836	High Similarity	NPC44573
0.8836	High Similarity	NPC103001
0.8831	High Similarity	NPC47781
0.8831	High Similarity	NPC86485
0.8831	High Similarity	NPC49402
0.8831	High Similarity	NPC183878
0.8831	High Similarity	NPC176775
0.8831	High Similarity	NPC255350
0.8831	High Similarity	NPC476289
0.8831	High Similarity	NPC276409
0.8831	High Similarity	NPC231018
0.8831	High Similarity	NPC75279
0.8831	High Similarity	NPC70433
0.8831	High Similarity	NPC160951
0.8831	High Similarity	NPC57211
0.8831	High Similarity	NPC478213
0.8831	High Similarity	NPC273462
0.8831	High Similarity	NPC22519
0.8831	High Similarity	NPC250822
0.8831	High Similarity	NPC69394
0.8831	High Similarity	NPC33051
0.8831	High Similarity	NPC227337
0.8831	High Similarity	NPC274327
0.8831	High Similarity	NPC145379
0.8824	High Similarity	NPC262623
0.8824	High Similarity	NPC279061
0.8824	High Similarity	NPC473732
0.8816	High Similarity	NPC328119
0.8812	High Similarity	NPC135345

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 NPC198615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	1044
0.2-0.3	1976
0.3-0.4	2681
0.4-0.5	1719
0.5-0.6	864
0.6-0.7	310
0.7-0.8	99
0.8-0.85	29
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.891	High Similarity	NPD5494	Approved
0.8896	High Similarity	NPD3817	Phase 2
0.8831	High Similarity	NPD2801	Approved
0.8645	High Similarity	NPD1934	Approved
0.8481	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD1465	Phase 2
0.8471	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7819	Suspended
0.8442	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD5844	Phase 1
0.8389	Intermediate Similarity	NPD2796	Approved
0.8375	Intermediate Similarity	NPD919	Approved
0.8366	Intermediate Similarity	NPD1511	Approved
0.8366	Intermediate Similarity	NPD6799	Approved
0.8365	Intermediate Similarity	NPD3882	Suspended
0.8354	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD3818	Discontinued
0.8344	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6166	Phase 2
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8302	Intermediate Similarity	NPD5402	Approved
0.8293	Intermediate Similarity	NPD7473	Discontinued
0.8291	Intermediate Similarity	NPD6801	Discontinued
0.8282	Intermediate Similarity	NPD3926	Phase 2
0.8272	Intermediate Similarity	NPD1247	Approved
0.8258	Intermediate Similarity	NPD1512	Approved
0.8253	Intermediate Similarity	NPD7074	Phase 3
0.8228	Intermediate Similarity	NPD7411	Suspended
0.8205	Intermediate Similarity	NPD920	Approved
0.8193	Intermediate Similarity	NPD7054	Approved
0.8165	Intermediate Similarity	NPD6599	Discontinued
0.8144	Intermediate Similarity	NPD7472	Approved
0.8121	Intermediate Similarity	NPD1933	Approved
0.8121	Intermediate Similarity	NPD447	Suspended
0.8105	Intermediate Similarity	NPD1243	Approved
0.8086	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD3748	Approved
0.8077	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD4380	Phase 2
0.8039	Intermediate Similarity	NPD1549	Phase 2
0.8	Intermediate Similarity	NPD7808	Phase 3
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7988	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3749	Approved
0.7974	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7251	Discontinued
0.7908	Intermediate Similarity	NPD2935	Discontinued
0.7905	Intermediate Similarity	NPD6832	Phase 2
0.7875	Intermediate Similarity	NPD3226	Approved
0.7862	Intermediate Similarity	NPD5403	Approved
0.7848	Intermediate Similarity	NPD5401	Approved
0.7843	Intermediate Similarity	NPD1510	Phase 2
0.7834	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3750	Approved
0.7815	Intermediate Similarity	NPD1240	Approved
0.7798	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2346	Discontinued
0.7738	Intermediate Similarity	NPD5242	Approved
0.7733	Intermediate Similarity	NPD6559	Discontinued
0.7727	Intermediate Similarity	NPD2799	Discontinued
0.7725	Intermediate Similarity	NPD6959	Discontinued
0.7712	Intermediate Similarity	NPD1607	Approved
0.7697	Intermediate Similarity	NPD943	Approved
0.7692	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2313	Discontinued
0.7661	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5353	Approved
0.7627	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7199	Phase 2
0.7593	Intermediate Similarity	NPD1653	Approved
0.759	Intermediate Similarity	NPD7768	Phase 2
0.7564	Intermediate Similarity	NPD1551	Phase 2
0.7562	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6386	Approved
0.7561	Intermediate Similarity	NPD6385	Approved
0.7532	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD2800	Approved
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2532	Approved
0.7516	Intermediate Similarity	NPD2534	Approved
0.7516	Intermediate Similarity	NPD2533	Approved
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD5953	Discontinued
0.7468	Intermediate Similarity	NPD4307	Phase 2
0.7467	Intermediate Similarity	NPD3267	Approved
0.7467	Intermediate Similarity	NPD3266	Approved
0.7467	Intermediate Similarity	NPD1203	Approved
0.7457	Intermediate Similarity	NPD7286	Phase 2
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD17	Approved
0.741	Intermediate Similarity	NPD37	Approved
0.7383	Intermediate Similarity	NPD9717	Approved
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7375	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3268	Approved
0.7338	Intermediate Similarity	NPD1296	Phase 2
0.7329	Intermediate Similarity	NPD6190	Approved
0.7303	Intermediate Similarity	NPD2798	Approved
0.7303	Intermediate Similarity	NPD1019	Discontinued
0.7299	Intermediate Similarity	NPD3751	Discontinued
0.7296	Intermediate Similarity	NPD2344	Approved
0.7294	Intermediate Similarity	NPD6234	Discontinued
0.7283	Intermediate Similarity	NPD2403	Approved
0.7283	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD1608	Approved
0.7244	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1613	Approved
0.7237	Intermediate Similarity	NPD2797	Approved
0.7233	Intermediate Similarity	NPD6100	Approved
0.7233	Intermediate Similarity	NPD6099	Approved
0.7226	Intermediate Similarity	NPD411	Approved
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7211	Intermediate Similarity	NPD5536	Phase 2
0.7191	Intermediate Similarity	NPD7549	Discontinued
0.7188	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2353	Approved
0.717	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6651	Approved
0.7151	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD3018	Phase 2
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7118	Intermediate Similarity	NPD4288	Approved
0.7117	Intermediate Similarity	NPD2309	Approved
0.7117	Intermediate Similarity	NPD3887	Approved
0.7114	Intermediate Similarity	NPD9268	Approved
0.711	Intermediate Similarity	NPD8127	Discontinued
0.7102	Intermediate Similarity	NPD7228	Approved
0.7101	Intermediate Similarity	NPD6844	Discontinued
0.7099	Intermediate Similarity	NPD2654	Approved
0.7093	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5006	Approved
0.709	Intermediate Similarity	NPD5005	Approved
0.7086	Intermediate Similarity	NPD422	Phase 1
0.7083	Intermediate Similarity	NPD6585	Discontinued
0.7081	Intermediate Similarity	NPD1471	Phase 3
0.7076	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6233	Phase 2
0.7069	Intermediate Similarity	NPD5711	Approved
0.7069	Intermediate Similarity	NPD5710	Approved
0.7069	Intermediate Similarity	NPD7229	Phase 3
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7059	Intermediate Similarity	NPD3225	Approved
0.7053	Intermediate Similarity	NPD7435	Discontinued
0.7051	Intermediate Similarity	NPD3027	Phase 3
0.7049	Intermediate Similarity	NPD4287	Approved
0.7041	Intermediate Similarity	NPD5890	Approved
0.7041	Intermediate Similarity	NPD5889	Approved
0.7041	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2981	Phase 2
0.7039	Intermediate Similarity	NPD9269	Phase 2
0.7039	Intermediate Similarity	NPD3972	Approved
0.7033	Intermediate Similarity	NPD8150	Discontinued
0.703	Intermediate Similarity	NPD7390	Discontinued
0.7021	Intermediate Similarity	NPD8285	Discontinued
0.7012	Intermediate Similarity	NPD2354	Approved
0.7006	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6798	Discontinued
0.7005	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1652	Phase 2
0.6993	Remote Similarity	NPD2983	Phase 2
0.6993	Remote Similarity	NPD2982	Phase 2
0.6988	Remote Similarity	NPD3146	Approved
0.6988	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5535	Approved
0.6984	Remote Similarity	NPD6781	Approved
0.6984	Remote Similarity	NPD6777	Approved
0.6984	Remote Similarity	NPD6776	Approved
0.6984	Remote Similarity	NPD6782	Approved
0.6984	Remote Similarity	NPD6780	Approved
0.6984	Remote Similarity	NPD6779	Approved
0.6984	Remote Similarity	NPD6778	Approved
0.6974	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7783	Phase 2
0.6971	Remote Similarity	NPD6808	Phase 2
0.6968	Remote Similarity	NPD4420	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