NPASS Compound

Structure

NPC183236 OpenBabel07101718222D 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 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 3.4641 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 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 2.5981 -1.5000 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 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 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 -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 -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 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 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 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 2.5981 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 -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 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 7 2 0 0 0 0 5 13 1 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 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 17 1 0 0 0 0 13 18 2 0 0 0 0 14 17 1 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 15 27 1 0 0 0 0 16 21 2 0 0 0 0 16 28 1 0 0 0 0 17 26 2 0 0 0 0 18 20 1 0 0 0 0 18 31 1 0 0 0 0 19 21 1 0 0 0 0 19 31 1 0 0 0 0 20 29 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:	1.964
LogD:	1.572
LogS:	-5.654
# 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:	2.726
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:	-4.844
MDCK Permeability:	2.51440069405362e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.788
20% Bioavailability (F20%):	0.576
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.584
Plasma Protein Binding (PPB):	76.73624420166016%
Volume Distribution (VD):	0.654
Pgp-substrate:	24.91518783569336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.622
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.29
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.756
CYP2C9-substrate:	0.475
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.133
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	1.42
Half-life (T1/2):	0.732

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.002
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.957
Carcinogencity:	0.194
Eye Corrosion:	0.259
Eye Irritation:	0.462
Respiratory Toxicity:	0.178

Download Data

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

Natural Product: NPC183236

Natural Product ID:	NPC183236
*Common Name:**	(4,5,6-Triacetyloxy-9-Oxoxanthen-3-Yl) Acetate
IUPAC Name:	(4,5,6-triacetyloxy-9-oxoxanthen-3-yl) acetate
Synonyms:
Standard InCHIKey:	GTOUZRBAQUHKJV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H16O10/c1-9(22)27-15-7-5-13-17(26)14-6-8-16(28-10(2)23)21(30-12(4)25)19(14)31-18(13)20(15)29-11(3)24/h5-8H,1-4H3
SMILES:	CC(=O)Oc1c(ccc2c1oc1c(OC(=O)C)c(ccc1c2=O)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478777
PubChem CID:	44584696
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	=	7.0	%	PMID[532756]

☑ 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 NPC183236 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	490
0.1-0.2	2017
0.2-0.3	5526
0.3-0.4	11071
0.4-0.5	6133
0.5-0.6	4137
0.6-0.7	5868
0.7-0.8	4748
0.8-0.85	2043
0.85-0.9	602
0.9-0.95	48
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC474648
0.9792	High Similarity	NPC198615
0.9722	High Similarity	NPC29056
0.9655	High Similarity	NPC474663
0.9392	High Similarity	NPC186507
0.9329	High Similarity	NPC471746
0.932	High Similarity	NPC177839
0.9315	High Similarity	NPC63256
0.9315	High Similarity	NPC10304
0.9306	High Similarity	NPC293201
0.9267	High Similarity	NPC474983
0.9262	High Similarity	NPC475895
0.9257	High Similarity	NPC474170
0.9257	High Similarity	NPC474388
0.9257	High Similarity	NPC472535
0.9247	High Similarity	NPC470511
0.9241	High Similarity	NPC471590
0.9241	High Similarity	NPC136278
0.92	High Similarity	NPC34725
0.92	High Similarity	NPC241774
0.92	High Similarity	NPC276059
0.92	High Similarity	NPC122623
0.9178	High Similarity	NPC231013
0.9172	High Similarity	NPC113089
0.9139	High Similarity	NPC257277
0.9122	High Similarity	NPC238366
0.9116	High Similarity	NPC205522
0.9116	High Similarity	NPC85233
0.911	High Similarity	NPC165512
0.9103	High Similarity	NPC9966
0.9103	High Similarity	NPC70853
0.9085	High Similarity	NPC477164
0.9079	High Similarity	NPC108456
0.9067	High Similarity	NPC166201
0.9054	High Similarity	NPC476342
0.9048	High Similarity	NPC283002
0.9048	High Similarity	NPC302408
0.9048	High Similarity	NPC40818
0.9048	High Similarity	NPC106461
0.9048	High Similarity	NPC215932
0.9048	High Similarity	NPC14958
0.9048	High Similarity	NPC110639
0.9034	High Similarity	NPC29536
0.9034	High Similarity	NPC185607
0.9021	High Similarity	NPC103001
0.9021	High Similarity	NPC44573
0.9007	High Similarity	NPC273462
0.9007	High Similarity	NPC49402
0.9007	High Similarity	NPC70433
0.9007	High Similarity	NPC33051
0.9007	High Similarity	NPC227337
0.8986	High Similarity	NPC299923
0.8986	High Similarity	NPC77378
0.898	High Similarity	NPC213482
0.8968	High Similarity	NPC108767
0.8947	High Similarity	NPC117992
0.8947	High Similarity	NPC222185
0.8947	High Similarity	NPC256925
0.8947	High Similarity	NPC57674
0.8947	High Similarity	NPC255807
0.8947	High Similarity	NPC168247
0.8947	High Similarity	NPC230149
0.8947	High Similarity	NPC31018
0.8947	High Similarity	NPC152951
0.894	High Similarity	NPC257648
0.894	High Similarity	NPC475116
0.894	High Similarity	NPC40033
0.894	High Similarity	NPC68882
0.894	High Similarity	NPC477231
0.8933	High Similarity	NPC5840
0.8933	High Similarity	NPC189270
0.8933	High Similarity	NPC259058
0.8933	High Similarity	NPC29231
0.8933	High Similarity	NPC201547
0.8926	High Similarity	NPC196277
0.8926	High Similarity	NPC272721
0.8926	High Similarity	NPC43669
0.8919	High Similarity	NPC195919
0.8919	High Similarity	NPC216314
0.8919	High Similarity	NPC120924
0.8919	High Similarity	NPC310259
0.8912	High Similarity	NPC23955
0.8912	High Similarity	NPC182842
0.891	High Similarity	NPC474350
0.8904	High Similarity	NPC24075
0.8897	High Similarity	NPC136095
0.8889	High Similarity	NPC470600
0.8889	High Similarity	NPC115853
0.8882	High Similarity	NPC244371
0.8882	High Similarity	NPC128961
0.8882	High Similarity	NPC472915
0.8882	High Similarity	NPC472408
0.8874	High Similarity	NPC117579
0.8874	High Similarity	NPC149614
0.8874	High Similarity	NPC31363
0.8874	High Similarity	NPC473732
0.8867	High Similarity	NPC69752
0.8867	High Similarity	NPC181250
0.8859	High Similarity	NPC117463
0.8854	High Similarity	NPC280893
0.8846	High Similarity	NPC414831
0.8846	High Similarity	NPC471745
0.8844	High Similarity	NPC476054
0.8836	High Similarity	NPC171094
0.8836	High Similarity	NPC58229
0.8831	High Similarity	NPC304008
0.8831	High Similarity	NPC218313
0.8831	High Similarity	NPC181960
0.8831	High Similarity	NPC180011
0.8831	High Similarity	NPC474681
0.8831	High Similarity	NPC258644
0.8831	High Similarity	NPC161960
0.8831	High Similarity	NPC299520
0.8831	High Similarity	NPC129684
0.8831	High Similarity	NPC310206
0.8831	High Similarity	NPC219867
0.8831	High Similarity	NPC187745
0.8824	High Similarity	NPC200246
0.8824	High Similarity	NPC472909
0.8824	High Similarity	NPC472280
0.8824	High Similarity	NPC37392
0.8816	High Similarity	NPC39007
0.8816	High Similarity	NPC472912
0.8816	High Similarity	NPC134677
0.8816	High Similarity	NPC161277
0.8816	High Similarity	NPC39732
0.8816	High Similarity	NPC60972
0.8808	High Similarity	NPC473466
0.8808	High Similarity	NPC179183
0.8808	High Similarity	NPC248102
0.8808	High Similarity	NPC338131
0.88	High Similarity	NPC261548
0.88	High Similarity	NPC195202
0.879	High Similarity	NPC300984
0.8782	High Similarity	NPC303565
0.8782	High Similarity	NPC112418
0.8776	High Similarity	NPC124467
0.8776	High Similarity	NPC214919
0.8774	High Similarity	NPC204879
0.8767	High Similarity	NPC472515
0.8767	High Similarity	NPC473209
0.8766	High Similarity	NPC138243
0.8766	High Similarity	NPC472907
0.8766	High Similarity	NPC191146
0.8766	High Similarity	NPC6633
0.8766	High Similarity	NPC180340
0.8766	High Similarity	NPC155063
0.8766	High Similarity	NPC303255
0.8766	High Similarity	NPC5322
0.8766	High Similarity	NPC133970
0.8766	High Similarity	NPC54928
0.8766	High Similarity	NPC472916
0.8766	High Similarity	NPC68093
0.8766	High Similarity	NPC472455
0.8758	High Similarity	NPC206238
0.8758	High Similarity	NPC280937
0.8758	High Similarity	NPC18727
0.8758	High Similarity	NPC167091
0.8758	High Similarity	NPC292214
0.8758	High Similarity	NPC88645
0.8758	High Similarity	NPC271779
0.8758	High Similarity	NPC472905
0.8758	High Similarity	NPC469550
0.875	High Similarity	NPC208043
0.875	High Similarity	NPC308451
0.875	High Similarity	NPC226973
0.875	High Similarity	NPC171010
0.875	High Similarity	NPC251110
0.8742	High Similarity	NPC164299
0.8742	High Similarity	NPC116745
0.8734	High Similarity	NPC88243
0.8734	High Similarity	NPC475369
0.8733	High Similarity	NPC62536
0.8733	High Similarity	NPC33265
0.8733	High Similarity	NPC474999
0.8733	High Similarity	NPC168803
0.8733	High Similarity	NPC12200
0.8726	High Similarity	NPC93739
0.8725	High Similarity	NPC224687
0.8725	High Similarity	NPC287275
0.8725	High Similarity	NPC296575
0.8718	High Similarity	NPC298093
0.8718	High Similarity	NPC188433
0.8718	High Similarity	NPC471744
0.8718	High Similarity	NPC130955
0.8718	High Similarity	NPC53889
0.8716	High Similarity	NPC119663
0.871	High Similarity	NPC475267
0.871	High Similarity	NPC472963
0.871	High Similarity	NPC36852
0.871	High Similarity	NPC19097
0.871	High Similarity	NPC67876
0.871	High Similarity	NPC474836
0.871	High Similarity	NPC78225
0.871	High Similarity	NPC474208
0.871	High Similarity	NPC472913
0.871	High Similarity	NPC136674
0.871	High Similarity	NPC476981
0.871	High Similarity	NPC262286
0.871	High Similarity	NPC472910

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 NPC183236 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	1035
0.2-0.3	1897
0.3-0.4	2674
0.4-0.5	1760
0.5-0.6	898
0.6-0.7	335
0.7-0.8	99
0.8-0.85	37
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD3817	Phase 2
0.8718	High Similarity	NPD5494	Approved
0.8693	High Similarity	NPD1934	Approved
0.8636	High Similarity	NPD2801	Approved
0.8636	High Similarity	NPD7819	Suspended
0.8609	High Similarity	NPD6980	Clinical (unspecified phase)
0.8562	High Similarity	NPD2796	Approved
0.8535	High Similarity	NPD919	Approved
0.8533	High Similarity	NPD6799	Approved
0.8526	High Similarity	NPD3882	Suspended
0.8526	High Similarity	NPD4868	Clinical (unspecified phase)
0.8516	High Similarity	NPD2393	Clinical (unspecified phase)
0.8516	High Similarity	NPD1465	Phase 2
0.8516	High Similarity	NPD7096	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7075	Discontinued
0.8452	Intermediate Similarity	NPD6801	Discontinued
0.8438	Intermediate Similarity	NPD3926	Phase 2
0.8411	Intermediate Similarity	NPD1511	Approved
0.8395	Intermediate Similarity	NPD3818	Discontinued
0.8387	Intermediate Similarity	NPD7411	Suspended
0.8385	Intermediate Similarity	NPD6166	Phase 2
0.8385	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8323	Intermediate Similarity	NPD6599	Discontinued
0.8301	Intermediate Similarity	NPD1512	Approved
0.8293	Intermediate Similarity	NPD7074	Phase 3
0.8288	Intermediate Similarity	NPD1933	Approved
0.8267	Intermediate Similarity	NPD1243	Approved
0.8253	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD920	Approved
0.8243	Intermediate Similarity	NPD3748	Approved
0.8232	Intermediate Similarity	NPD5844	Phase 1
0.8232	Intermediate Similarity	NPD7054	Approved
0.82	Intermediate Similarity	NPD1549	Phase 2
0.8182	Intermediate Similarity	NPD7472	Approved
0.8163	Intermediate Similarity	NPD447	Suspended
0.8133	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3749	Approved
0.8117	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD5402	Approved
0.8089	Intermediate Similarity	NPD4380	Phase 2
0.8086	Intermediate Similarity	NPD1247	Approved
0.8069	Intermediate Similarity	NPD6832	Phase 2
0.8036	Intermediate Similarity	NPD7808	Phase 3
0.8024	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6797	Phase 2
0.8013	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7987	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7251	Discontinued
0.7974	Intermediate Similarity	NPD3750	Approved
0.7973	Intermediate Similarity	NPD1240	Approved
0.7939	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD3226	Approved
0.7888	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2799	Discontinued
0.7867	Intermediate Similarity	NPD1607	Approved
0.7852	Intermediate Similarity	NPD943	Approved
0.7843	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2346	Discontinued
0.7771	Intermediate Similarity	NPD5242	Approved
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7758	Intermediate Similarity	NPD6959	Discontinued
0.7758	Intermediate Similarity	NPD7199	Phase 2
0.773	Intermediate Similarity	NPD7768	Phase 2
0.7718	Intermediate Similarity	NPD2313	Discontinued
0.7712	Intermediate Similarity	NPD2935	Discontinued
0.7712	Intermediate Similarity	NPD1551	Phase 2
0.7707	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5353	Approved
0.7665	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD3266	Approved
0.7619	Intermediate Similarity	NPD1203	Approved
0.7619	Intermediate Similarity	NPD3267	Approved
0.7616	Intermediate Similarity	NPD4307	Phase 2
0.7602	Intermediate Similarity	NPD5953	Discontinued
0.7593	Intermediate Similarity	NPD6386	Approved
0.7593	Intermediate Similarity	NPD6385	Approved
0.7586	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD17	Approved
0.7566	Intermediate Similarity	NPD230	Phase 1
0.7564	Intermediate Similarity	NPD2800	Approved
0.7547	Intermediate Similarity	NPD2534	Approved
0.7547	Intermediate Similarity	NPD2532	Approved
0.7547	Intermediate Similarity	NPD2533	Approved
0.7534	Intermediate Similarity	NPD9717	Approved
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7286	Phase 2
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7483	Intermediate Similarity	NPD3268	Approved
0.7473	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2798	Approved
0.7439	Intermediate Similarity	NPD37	Approved
0.7436	Intermediate Similarity	NPD2344	Approved
0.7419	Intermediate Similarity	NPD4308	Phase 3
0.7415	Intermediate Similarity	NPD1608	Approved
0.7412	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4966	Approved
0.741	Intermediate Similarity	NPD4965	Approved
0.741	Intermediate Similarity	NPD4967	Phase 2
0.7407	Intermediate Similarity	NPD1653	Approved
0.74	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2797	Approved
0.7372	Intermediate Similarity	NPD6100	Approved
0.7372	Intermediate Similarity	NPD6099	Approved
0.7368	Intermediate Similarity	NPD411	Approved
0.7361	Intermediate Similarity	NPD5536	Phase 2
0.7333	Intermediate Similarity	NPD1019	Discontinued
0.7325	Intermediate Similarity	NPD2353	Approved
0.7325	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.731	Intermediate Similarity	NPD2403	Approved
0.7308	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6651	Approved
0.7288	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3018	Phase 2
0.7278	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1613	Approved
0.725	Intermediate Similarity	NPD2309	Approved
0.725	Intermediate Similarity	NPD3887	Approved
0.725	Intermediate Similarity	NPD6190	Approved
0.7246	Intermediate Similarity	NPD4288	Approved
0.7233	Intermediate Similarity	NPD2654	Approved
0.723	Intermediate Similarity	NPD422	Phase 1
0.7225	Intermediate Similarity	NPD3751	Discontinued
0.7222	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1471	Phase 3
0.7212	Intermediate Similarity	NPD6585	Discontinued
0.7202	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3225	Approved
0.7197	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7033	Discontinued
0.7193	Intermediate Similarity	NPD3787	Discontinued
0.7181	Intermediate Similarity	NPD2981	Phase 2
0.7181	Intermediate Similarity	NPD3972	Approved
0.7178	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8313	Approved
0.7175	Intermediate Similarity	NPD8312	Approved
0.7169	Intermediate Similarity	NPD5889	Approved
0.7169	Intermediate Similarity	NPD5890	Approved
0.7167	Intermediate Similarity	NPD4287	Approved
0.7159	Intermediate Similarity	NPD7685	Pre-registration
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD2354	Approved
0.7143	Intermediate Similarity	NPD9268	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7133	Intermediate Similarity	NPD2982	Phase 2
0.7133	Intermediate Similarity	NPD5535	Approved
0.7133	Intermediate Similarity	NPD2983	Phase 2
0.7126	Intermediate Similarity	NPD7228	Approved
0.7126	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3146	Approved
0.7117	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5005	Approved
0.7112	Intermediate Similarity	NPD5006	Approved
0.7093	Intermediate Similarity	NPD5711	Approved
0.7093	Intermediate Similarity	NPD7229	Phase 3
0.7093	Intermediate Similarity	NPD5710	Approved
0.7093	Intermediate Similarity	NPD6808	Phase 2
0.7078	Intermediate Similarity	NPD3027	Phase 3
0.7067	Intermediate Similarity	NPD9269	Phase 2
0.7066	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6971	Discontinued
0.7059	Intermediate Similarity	NPD9494	Approved
0.7055	Intermediate Similarity	NPD7390	Discontinued
0.7048	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7458	Discontinued
0.7043	Intermediate Similarity	NPD8285	Discontinued
0.7041	Intermediate Similarity	NPD5978	Approved
0.7041	Intermediate Similarity	NPD5977	Approved
0.7032	Intermediate Similarity	NPD3764	Approved
0.7022	Intermediate Similarity	NPD7549	Discontinued
0.7022	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1652	Phase 2
0.7013	Intermediate Similarity	NPD4908	Phase 1
0.7006	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5124	Phase 1
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.6989	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