NPASS Compound

Structure

CID246466 OpenBabel06191716052D 29 31 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 -2.0000 1.7321 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 -3.0000 -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 2 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 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 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 12 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 28 1 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 14 23 1 0 0 0 0 15 28 1 0 0 0 0 16 20 1 0 0 0 0 17 19 2 0 0 0 0 17 27 1 0 0 0 0 18 22 1 1 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 21 26 2 0 0 0 0 21 29 1 0 0 0 0 22 3 1 6 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.17
Volume:	406.475
LogP:	2.676
LogD:	1.837
LogS:	-3.532
# Rotatable Bonds:	5
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	4.612
Fsp3:	0.455
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:	-4.949
MDCK Permeability:	2.291826967848465e-05
Pgp-inhibitor:	0.089
Pgp-substrate:	0.627
Human Intestinal Absorption (HIA):	0.156
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.517

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.937
Plasma Protein Binding (PPB):	89.76807403564453%
Volume Distribution (VD):	0.773
Pgp-substrate:	6.6186299324035645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.791
CYP1A2-substrate:	0.445
CYP2C19-inhibitor:	0.483
CYP2C19-substrate:	0.753
CYP2C9-inhibitor:	0.656
CYP2C9-substrate:	0.501
CYP2D6-inhibitor:	0.484
CYP2D6-substrate:	0.217
CYP3A4-inhibitor:	0.909
CYP3A4-substrate:	0.596

ADMET: Excretion

Clearance (CL):	7.98
Half-life (T1/2):	0.711

ADMET: Toxicity

hERG Blockers:	0.351
Human Hepatotoxicity (H-HT):	0.771
Drug-inuced Liver Injury (DILI):	0.448
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.945
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.517
Carcinogencity:	0.304
Eye Corrosion:	0.003
Eye Irritation:	0.048
Respiratory Toxicity:	0.794

Download Data

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

Natural Product: NPC246466

Natural Product ID:	NPC246466
*Common Name:**	Comazaphilone A
IUPAC Name:	[(6R,7R)-6-hydroxy-7-methyl-8-oxo-3-propyl-5,6-dihydro-1H-isochromen-7-yl] 4-hydroxy-2-methoxy-6-methylbenzoate
Synonyms:	Comazaphilone A
Standard InCHIKey:	BJMHMPAXPWFBRJ-XMSQKQJNSA-N
Standard InCHI:	InChI=1S/C22H26O7/c1-5-6-15-8-13-9-18(24)22(3,20(25)16(13)11-28-15)29-21(26)19-12(2)7-14(23)10-17(19)27-4/h7-8,10,18,23-24H,5-6,9,11H2,1-4H3/t18-,22-/m1/s1
SMILES:	CCCC1=CC2=C(CO1)C(=O)[C@@](C)([C@@H](C2)O)OC(=O)c1c(C)cc(cc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689195
PubChem CID:	51041529
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003477] Azaphilones

*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
NPO33529	Penicillium commune QSD-17	Species	Aspergillaceae	Eukaryota	marine sediment	southern China Sea	n.a.	PMID[21226488]
NPO19186	Penicillium commune	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21226488]
NPO19186	Penicillium commune	Species	Aspergillaceae	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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	256.0	ug.mL-1	PMID[511100]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	256.0	ug.mL-1	PMID[511100]
NPT1209	Organism	Pseudomonas fluorescens	Pseudomonas fluorescens	MIC	>	256.0	ug.mL-1	PMID[511100]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	256.0	ug.mL-1	PMID[511100]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	256.0	ug.mL-1	PMID[511100]

☑ 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 NPC246466 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	357
0.1-0.2	1452
0.2-0.3	3518
0.3-0.4	7594
0.4-0.5	10313
0.5-0.6	4518
0.6-0.7	5857
0.7-0.8	7165
0.8-0.85	1603
0.85-0.9	271
0.9-0.95	40
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC472889
0.9603	High Similarity	NPC170189
0.9603	High Similarity	NPC208173
0.96	High Similarity	NPC115249
0.9551	High Similarity	NPC20237
0.9536	High Similarity	NPC137301
0.949	High Similarity	NPC283041
0.9474	High Similarity	NPC478221
0.9474	High Similarity	NPC69043
0.9474	High Similarity	NPC478230
0.947	High Similarity	NPC76041
0.947	High Similarity	NPC478224
0.947	High Similarity	NPC184284
0.9467	High Similarity	NPC472891
0.9423	High Similarity	NPC249181
0.9408	High Similarity	NPC478231
0.9363	High Similarity	NPC191930
0.9346	High Similarity	NPC472890
0.9346	High Similarity	NPC317585
0.9295	High Similarity	NPC117985
0.929	High Similarity	NPC470339
0.9286	High Similarity	NPC472050
0.9272	High Similarity	NPC237440
0.9272	High Similarity	NPC270160
0.9267	High Similarity	NPC210320
0.9231	High Similarity	NPC472055
0.9226	High Similarity	NPC478226
0.9226	High Similarity	NPC478225
0.9205	High Similarity	NPC215711
0.9205	High Similarity	NPC73411
0.9172	High Similarity	NPC317544
0.915	High Similarity	NPC91809
0.9145	High Similarity	NPC4423
0.9145	High Similarity	NPC84142
0.9145	High Similarity	NPC77325
0.9091	High Similarity	NPC470340
0.9085	High Similarity	NPC164762
0.9068	High Similarity	NPC473096
0.9068	High Similarity	NPC473095
0.9067	High Similarity	NPC210425
0.9067	High Similarity	NPC280404
0.9067	High Similarity	NPC277426
0.9067	High Similarity	NPC86373
0.9032	High Similarity	NPC155686
0.9032	High Similarity	NPC471695
0.9026	High Similarity	NPC132990
0.9026	High Similarity	NPC46882
0.9026	High Similarity	NPC70016
0.9026	High Similarity	NPC215921
0.9006	High Similarity	NPC473094
0.9	High Similarity	NPC472049
0.9	High Similarity	NPC51106
0.8993	High Similarity	NPC244923
0.8974	High Similarity	NPC99381
0.8968	High Similarity	NPC268992
0.8968	High Similarity	NPC113608
0.8968	High Similarity	NPC167903
0.8968	High Similarity	NPC51824
0.8968	High Similarity	NPC470337
0.8968	High Similarity	NPC470338
0.8968	High Similarity	NPC256141
0.8961	High Similarity	NPC179178
0.8954	High Similarity	NPC240622
0.8954	High Similarity	NPC471642
0.8954	High Similarity	NPC471641
0.8954	High Similarity	NPC240253
0.8933	High Similarity	NPC474385
0.8924	High Similarity	NPC477410
0.891	High Similarity	NPC192189
0.8903	High Similarity	NPC200773
0.8903	High Similarity	NPC240768
0.8889	High Similarity	NPC259632
0.8889	High Similarity	NPC472036
0.8874	High Similarity	NPC469542
0.8874	High Similarity	NPC472006
0.8868	High Similarity	NPC243701
0.8867	High Similarity	NPC67650
0.8867	High Similarity	NPC158634
0.8867	High Similarity	NPC1704
0.8861	High Similarity	NPC473395
0.8859	High Similarity	NPC247409
0.8859	High Similarity	NPC32360
0.8859	High Similarity	NPC268052
0.8854	High Similarity	NPC82592
0.8854	High Similarity	NPC16082
0.8854	High Similarity	NPC68727
0.8846	High Similarity	NPC180944
0.8839	High Similarity	NPC469619
0.8839	High Similarity	NPC180351
0.8839	High Similarity	NPC469670
0.8834	High Similarity	NPC328321
0.8824	High Similarity	NPC473023
0.8824	High Similarity	NPC260946
0.8824	High Similarity	NPC107625
0.8808	High Similarity	NPC469579
0.8808	High Similarity	NPC82913
0.88	High Similarity	NPC158472
0.8797	High Similarity	NPC164427
0.879	High Similarity	NPC281477
0.879	High Similarity	NPC472799
0.879	High Similarity	NPC301233
0.878	High Similarity	NPC313717
0.878	High Similarity	NPC315306
0.8766	High Similarity	NPC85773
0.8758	High Similarity	NPC211107
0.8758	High Similarity	NPC312789
0.8758	High Similarity	NPC472034
0.875	High Similarity	NPC470810
0.8743	High Similarity	NPC477682
0.8743	High Similarity	NPC477683
0.8742	High Similarity	NPC475730
0.8742	High Similarity	NPC77679
0.8742	High Similarity	NPC84935
0.8742	High Similarity	NPC190020
0.8734	High Similarity	NPC217706
0.8734	High Similarity	NPC259710
0.8734	High Similarity	NPC326910
0.8734	High Similarity	NPC304207
0.8734	High Similarity	NPC48579
0.8734	High Similarity	NPC80534
0.8734	High Similarity	NPC207809
0.8734	High Similarity	NPC79998
0.8734	High Similarity	NPC56786
0.8734	High Similarity	NPC473241
0.8734	High Similarity	NPC237560
0.8727	High Similarity	NPC473113
0.8727	High Similarity	NPC472620
0.8726	High Similarity	NPC273483
0.8725	High Similarity	NPC135837
0.872	High Similarity	NPC472619
0.8718	High Similarity	NPC225854
0.8718	High Similarity	NPC56204
0.8718	High Similarity	NPC150928
0.8718	High Similarity	NPC158866
0.8712	High Similarity	NPC165460
0.871	High Similarity	NPC37139
0.871	High Similarity	NPC10097
0.871	High Similarity	NPC153417
0.8704	High Similarity	NPC474240
0.8704	High Similarity	NPC476822
0.8701	High Similarity	NPC472033
0.8701	High Similarity	NPC474302
0.8696	High Similarity	NPC112418
0.8693	High Similarity	NPC475201
0.8679	High Similarity	NPC227062
0.8679	High Similarity	NPC272550
0.8679	High Similarity	NPC150227
0.8671	High Similarity	NPC180301
0.8671	High Similarity	NPC236756
0.8671	High Similarity	NPC311579
0.8671	High Similarity	NPC248793
0.8671	High Similarity	NPC193200
0.8667	High Similarity	NPC33144
0.8667	High Similarity	NPC212693
0.8667	High Similarity	NPC191835
0.8667	High Similarity	NPC298778
0.8667	High Similarity	NPC478200
0.8667	High Similarity	NPC94248
0.8662	High Similarity	NPC254412
0.8662	High Similarity	NPC295650
0.8662	High Similarity	NPC262039
0.8662	High Similarity	NPC278476
0.8662	High Similarity	NPC262038
0.8662	High Similarity	NPC319910
0.8662	High Similarity	NPC205918
0.8659	High Similarity	NPC472622
0.8654	High Similarity	NPC477941
0.8654	High Similarity	NPC198927
0.8654	High Similarity	NPC139966
0.8654	High Similarity	NPC307052
0.8654	High Similarity	NPC476684
0.865	High Similarity	NPC475888
0.865	High Similarity	NPC294722
0.8645	High Similarity	NPC166583
0.8645	High Similarity	NPC53362
0.8645	High Similarity	NPC91902
0.8645	High Similarity	NPC14098
0.8645	High Similarity	NPC8817
0.8645	High Similarity	NPC47388
0.8645	High Similarity	NPC473133
0.8645	High Similarity	NPC21835
0.8645	High Similarity	NPC51070
0.8645	High Similarity	NPC202494
0.8645	High Similarity	NPC470670
0.8645	High Similarity	NPC222298
0.8642	High Similarity	NPC471745
0.8642	High Similarity	NPC48860
0.8639	High Similarity	NPC208069
0.8636	High Similarity	NPC83272
0.8634	High Similarity	NPC470183
0.8634	High Similarity	NPC155302
0.8634	High Similarity	NPC313368
0.8634	High Similarity	NPC161947
0.8634	High Similarity	NPC471744
0.8627	High Similarity	NPC277369
0.8627	High Similarity	NPC478202
0.8627	High Similarity	NPC215451
0.8627	High Similarity	NPC471731
0.8627	High Similarity	NPC159721
0.8625	High Similarity	NPC263483

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 NPC246466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	917
0.2-0.3	1936
0.3-0.4	2546
0.4-0.5	1876
0.5-0.6	982
0.6-0.7	404
0.7-0.8	152
0.8-0.85	21
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8733	High Similarity	NPD970	Clinical (unspecified phase)
0.8625	High Similarity	NPD7075	Discontinued
0.8616	High Similarity	NPD3817	Phase 2
0.8608	High Similarity	NPD6801	Discontinued
0.8553	High Similarity	NPD7096	Clinical (unspecified phase)
0.8516	High Similarity	NPD2533	Approved
0.8516	High Similarity	NPD2532	Approved
0.8516	High Similarity	NPD2534	Approved
0.8481	Intermediate Similarity	NPD4380	Phase 2
0.8452	Intermediate Similarity	NPD6799	Approved
0.8397	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD5402	Approved
0.8365	Intermediate Similarity	NPD6599	Discontinued
0.8323	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8303	Intermediate Similarity	NPD6232	Discontinued
0.8294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD5403	Approved
0.8284	Intermediate Similarity	NPD6797	Phase 2
0.8274	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7473	Discontinued
0.8261	Intermediate Similarity	NPD1934	Approved
0.8235	Intermediate Similarity	NPD7251	Discontinued
0.8229	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1512	Approved
0.8221	Intermediate Similarity	NPD3882	Suspended
0.821	Intermediate Similarity	NPD2801	Approved
0.8204	Intermediate Similarity	NPD6166	Phase 2
0.8204	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7808	Phase 3
0.8171	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5401	Approved
0.8133	Intermediate Similarity	NPD6959	Discontinued
0.8101	Intermediate Similarity	NPD1511	Approved
0.8059	Intermediate Similarity	NPD5844	Phase 1
0.8059	Intermediate Similarity	NPD7054	Approved
0.8052	Intermediate Similarity	NPD1510	Phase 2
0.8025	Intermediate Similarity	NPD3750	Approved
0.8012	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3818	Discontinued
0.7949	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6559	Discontinued
0.7911	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7074	Phase 3
0.7898	Intermediate Similarity	NPD1549	Phase 2
0.7895	Intermediate Similarity	NPD3751	Discontinued
0.7885	Intermediate Similarity	NPD2796	Approved
0.787	Intermediate Similarity	NPD5710	Approved
0.787	Intermediate Similarity	NPD5711	Approved
0.7866	Intermediate Similarity	NPD7411	Suspended
0.7861	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1607	Approved
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7799	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD919	Approved
0.7797	Intermediate Similarity	NPD8150	Discontinued
0.7792	Intermediate Similarity	NPD1240	Approved
0.7784	Intermediate Similarity	NPD7435	Discontinued
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7765	Intermediate Similarity	NPD3787	Discontinued
0.7742	Intermediate Similarity	NPD230	Phase 1
0.7738	Intermediate Similarity	NPD3749	Approved
0.7736	Intermediate Similarity	NPD2800	Approved
0.7711	Intermediate Similarity	NPD37	Approved
0.7707	Intermediate Similarity	NPD3748	Approved
0.7697	Intermediate Similarity	NPD8434	Phase 2
0.7692	Intermediate Similarity	NPD6234	Discontinued
0.7679	Intermediate Similarity	NPD4966	Approved
0.7679	Intermediate Similarity	NPD4967	Phase 2
0.7679	Intermediate Similarity	NPD4965	Approved
0.7679	Intermediate Similarity	NPD7768	Phase 2
0.7674	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7658	Intermediate Similarity	NPD1551	Phase 2
0.7647	Intermediate Similarity	NPD5494	Approved
0.764	Intermediate Similarity	NPD6190	Approved
0.7636	Intermediate Similarity	NPD3226	Approved
0.7622	Intermediate Similarity	NPD6779	Approved
0.7622	Intermediate Similarity	NPD6780	Approved
0.7622	Intermediate Similarity	NPD6776	Approved
0.7622	Intermediate Similarity	NPD6782	Approved
0.7622	Intermediate Similarity	NPD6781	Approved
0.7622	Intermediate Similarity	NPD6777	Approved
0.7622	Intermediate Similarity	NPD6778	Approved
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6651	Approved
0.7554	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6100	Approved
0.7547	Intermediate Similarity	NPD6099	Approved
0.7546	Intermediate Similarity	NPD7390	Discontinued
0.7542	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7874	Approved
0.7539	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8313	Approved
0.7528	Intermediate Similarity	NPD8312	Approved
0.7516	Intermediate Similarity	NPD1243	Approved
0.7516	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD920	Approved
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1247	Approved
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7486	Intermediate Similarity	NPD7228	Approved
0.7452	Intermediate Similarity	NPD4060	Phase 1
0.7407	Intermediate Similarity	NPD7696	Phase 3
0.7407	Intermediate Similarity	NPD7697	Approved
0.7407	Intermediate Similarity	NPD7698	Approved
0.7399	Intermediate Similarity	NPD7199	Phase 2
0.7394	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7368	Intermediate Similarity	NPD7870	Phase 2
0.7368	Intermediate Similarity	NPD7871	Phase 2
0.7368	Intermediate Similarity	NPD8320	Phase 1
0.7368	Intermediate Similarity	NPD8319	Approved
0.7351	Intermediate Similarity	NPD6535	Approved
0.7351	Intermediate Similarity	NPD6534	Approved
0.7344	Intermediate Similarity	NPD7701	Phase 2
0.7325	Intermediate Similarity	NPD6798	Discontinued
0.7321	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1652	Phase 2
0.7296	Intermediate Similarity	NPD5124	Phase 1
0.7296	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD6355	Discontinued
0.7296	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5763	Approved
0.7284	Intermediate Similarity	NPD5762	Approved
0.7283	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD2403	Approved
0.7267	Intermediate Similarity	NPD2799	Discontinued
0.7263	Intermediate Similarity	NPD5953	Discontinued
0.7262	Intermediate Similarity	NPD1653	Approved
0.7247	Intermediate Similarity	NPD7286	Phase 2
0.7234	Intermediate Similarity	NPD7699	Phase 2
0.7234	Intermediate Similarity	NPD7700	Phase 2
0.7233	Intermediate Similarity	NPD943	Approved
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7801	Approved
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7222	Intermediate Similarity	NPD7685	Pre-registration
0.7222	Intermediate Similarity	NPD5405	Approved
0.7222	Intermediate Similarity	NPD5404	Approved
0.7222	Intermediate Similarity	NPD5406	Approved
0.7222	Intermediate Similarity	NPD5408	Approved
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7216	Intermediate Similarity	NPD3926	Phase 2
0.7215	Intermediate Similarity	NPD2313	Discontinued
0.7215	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD422	Phase 1
0.7175	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.7169	Intermediate Similarity	NPD3300	Phase 2
0.7164	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD9545	Approved
0.7152	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD6273	Approved
0.7127	Intermediate Similarity	NPD7240	Approved
0.7127	Intermediate Similarity	NPD6765	Approved
0.7127	Intermediate Similarity	NPD6764	Approved
0.7126	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1613	Approved
0.7125	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1203	Approved
0.711	Intermediate Similarity	NPD4288	Approved
0.711	Intermediate Similarity	NPD5353	Approved
0.7107	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3268	Approved
0.7107	Intermediate Similarity	NPD411	Approved
0.7107	Intermediate Similarity	NPD3764	Approved
0.7097	Intermediate Similarity	NPD4749	Approved
0.7091	Intermediate Similarity	NPD2654	Approved
0.7089	Intermediate Similarity	NPD6832	Phase 2
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1201	Approved
0.7074	Intermediate Similarity	NPD4363	Phase 3
0.7074	Intermediate Similarity	NPD4360	Phase 2
0.707	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2798	Approved
0.7066	Intermediate Similarity	NPD7236	Approved
0.7059	Intermediate Similarity	NPD4626	Approved
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7048	Intermediate Similarity	NPD7003	Approved
0.7044	Intermediate Similarity	NPD7095	Approved
0.7044	Intermediate Similarity	NPD4625	Phase 3
0.7032	Intermediate Similarity	NPD9269	Phase 2
0.7026	Intermediate Similarity	NPD7584	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