NPASS Compound

Structure

CID283041 OpenBabel06191716092D 30 32 0 0 1 0 0 0 0 0999 V2000 5.1962 -3.0000 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 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 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 -1.7321 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 -3.5000 -0.8660 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 -0.0000 -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 -4.5000 -0.8660 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 11 1 0 0 0 0 4 28 1 0 0 0 0 5 6 2 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 13 2 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 29 1 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 13 29 1 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 23 1 0 0 0 0 16 22 1 6 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 19 28 1 0 0 0 0 20 22 1 0 0 0 0 20 26 2 0 0 0 0 21 27 2 0 0 0 0 21 30 1 0 0 0 0 22 3 1 1 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.15
Volume:	412.629
LogP:	1.716
LogD:	1.696
LogS:	-3.419
# Rotatable Bonds:	5
TPSA:	122.52
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.505
Synthetic Accessibility Score:	4.474
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.926
MDCK Permeability:	1.6512380170752294e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.253
Human Intestinal Absorption (HIA):	0.17
20% Bioavailability (F20%):	0.735
30% Bioavailability (F30%):	0.44

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	92.3023452758789%
Volume Distribution (VD):	0.944
Pgp-substrate:	7.679662227630615%

ADMET: Metabolism

CYP1A2-inhibitor:	0.926
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.247
CYP2C19-substrate:	0.442
CYP2C9-inhibitor:	0.667
CYP2C9-substrate:	0.733
CYP2D6-inhibitor:	0.777
CYP2D6-substrate:	0.268
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.476

ADMET: Excretion

Clearance (CL):	6.736
Half-life (T1/2):	0.773

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.75
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.216
Rat Oral Acute Toxicity:	0.823
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.93
Carcinogencity:	0.291
Eye Corrosion:	0.003
Eye Irritation:	0.591
Respiratory Toxicity:	0.597

Download Data

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

Natural Product: NPC283041

Natural Product ID:	NPC283041
*Common Name:**	Comazaphilone C
IUPAC Name:	[(6R,7R)-6-hydroxy-7-methyl-8-oxo-3-[(E)-prop-1-enyl]-5,6-dihydro-1H-isochromen-7-yl] 3,4-dihydroxy-2-methoxy-6-methylbenzoate
Synonyms:	Comazaphilone C
Standard InCHIKey:	BVPLOPDDUJTCFL-JBAXFHHXSA-N
Standard InCHI:	InChI=1S/C22H24O8/c1-5-6-13-8-12-9-16(24)22(3,20(26)14(12)10-29-13)30-21(27)17-11(2)7-15(23)18(25)19(17)28-4/h5-8,16,23-25H,9-10H2,1-4H3/b6-5+/t16-,22-/m1/s1
SMILES:	C/C=C/C1=CC2=C(CO1)C(=O)[C@@](C)([C@@H](C2)O)OC(=O)c1c(C)cc(c(c1OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689197
PubChem CID:	51041752
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	=	16.0	ug.mL-1	PMID[542413]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	32.0	ug.mL-1	PMID[542413]
NPT1209	Organism	Pseudomonas fluorescens	Pseudomonas fluorescens	MIC	=	64.0	ug.mL-1	PMID[542413]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	256.0	ug.mL-1	PMID[542413]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	256.0	ug.mL-1	PMID[542413]

☑ 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 NPC283041 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	383
0.1-0.2	1548
0.2-0.3	3855
0.3-0.4	8242
0.4-0.5	9560
0.5-0.6	4337
0.6-0.7	5402
0.7-0.8	6862
0.8-0.85	2125
0.85-0.9	350
0.9-0.95	29
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC20237
0.9873	High Similarity	NPC191930
0.9809	High Similarity	NPC249181
0.949	High Similarity	NPC246466
0.9367	High Similarity	NPC472889
0.9299	High Similarity	NPC137301
0.9241	High Similarity	NPC170189
0.9241	High Similarity	NPC317585
0.9241	High Similarity	NPC69043
0.9241	High Similarity	NPC208173
0.9241	High Similarity	NPC478230
0.9236	High Similarity	NPC115249
0.9236	High Similarity	NPC478224
0.9207	High Similarity	NPC328321
0.9187	High Similarity	NPC477410
0.9177	High Similarity	NPC478231
0.913	High Similarity	NPC472055
0.9119	High Similarity	NPC478221
0.9119	High Similarity	NPC472890
0.9119	High Similarity	NPC16082
0.9119	High Similarity	NPC82592
0.9114	High Similarity	NPC184284
0.9114	High Similarity	NPC76041
0.9108	High Similarity	NPC472891
0.9074	High Similarity	NPC317544
0.9074	High Similarity	NPC117985
0.9068	High Similarity	NPC470339
0.9057	High Similarity	NPC281477
0.9006	High Similarity	NPC84935
0.9006	High Similarity	NPC190020
0.9006	High Similarity	NPC77679
0.9006	High Similarity	NPC478225
0.9	High Similarity	NPC16286
0.9	High Similarity	NPC79998
0.8976	High Similarity	NPC473095
0.8976	High Similarity	NPC473096
0.8963	High Similarity	NPC476822
0.8957	High Similarity	NPC87431
0.8957	High Similarity	NPC112418
0.8947	High Similarity	NPC182693
0.8944	High Similarity	NPC227062
0.8944	High Similarity	NPC150227
0.8944	High Similarity	NPC472050
0.8931	High Similarity	NPC91809
0.8931	High Similarity	NPC70016
0.8931	High Similarity	NPC215921
0.8929	High Similarity	NPC4390
0.8917	High Similarity	NPC210320
0.8916	High Similarity	NPC473094
0.8916	High Similarity	NPC158761
0.8909	High Similarity	NPC470457
0.8909	High Similarity	NPC472049
0.8902	High Similarity	NPC471745
0.8902	High Similarity	NPC48860
0.8896	High Similarity	NPC155302
0.8896	High Similarity	NPC155101
0.8896	High Similarity	NPC161947
0.8896	High Similarity	NPC471744
0.8889	High Similarity	NPC478226
0.8882	High Similarity	NPC56786
0.8882	High Similarity	NPC80534
0.8882	High Similarity	NPC99381
0.8882	High Similarity	NPC199926
0.8869	High Similarity	NPC153755
0.8869	High Similarity	NPC190003
0.8869	High Similarity	NPC175107
0.8868	High Similarity	NPC96501
0.8868	High Similarity	NPC164762
0.8862	High Similarity	NPC188079
0.8861	High Similarity	NPC215711
0.8861	High Similarity	NPC73411
0.8855	High Similarity	NPC477517
0.8855	High Similarity	NPC43319
0.8848	High Similarity	NPC470459
0.8848	High Similarity	NPC186686
0.8848	High Similarity	NPC472625
0.8841	High Similarity	NPC201560
0.8841	High Similarity	NPC474779
0.8841	High Similarity	NPC471499
0.8834	High Similarity	NPC280680
0.8834	High Similarity	NPC176300
0.8834	High Similarity	NPC9609
0.8834	High Similarity	NPC18607
0.8834	High Similarity	NPC7846
0.8834	High Similarity	NPC25495
0.8834	High Similarity	NPC143828
0.8834	High Similarity	NPC191459
0.8834	High Similarity	NPC130894
0.8834	High Similarity	NPC253634
0.8834	High Similarity	NPC300943
0.8834	High Similarity	NPC261004
0.8834	High Similarity	NPC105242
0.8834	High Similarity	NPC288669
0.8834	High Similarity	NPC115798
0.8834	High Similarity	NPC22472
0.8834	High Similarity	NPC18772
0.8834	High Similarity	NPC152166
0.8834	High Similarity	NPC4481
0.8834	High Similarity	NPC19687
0.8834	High Similarity	NPC204854
0.883	High Similarity	NPC244903
0.8827	High Similarity	NPC265511
0.8827	High Similarity	NPC54928
0.8827	High Similarity	NPC197751
0.8824	High Similarity	NPC472385
0.8824	High Similarity	NPC198324
0.882	High Similarity	NPC155686
0.882	High Similarity	NPC179126
0.882	High Similarity	NPC197188
0.882	High Similarity	NPC238672
0.882	High Similarity	NPC78326
0.882	High Similarity	NPC236223
0.882	High Similarity	NPC291510
0.882	High Similarity	NPC270620
0.882	High Similarity	NPC116850
0.882	High Similarity	NPC43872
0.882	High Similarity	NPC58382
0.882	High Similarity	NPC144801
0.882	High Similarity	NPC162351
0.8817	High Similarity	NPC476374
0.8812	High Similarity	NPC240768
0.8812	High Similarity	NPC200773
0.881	High Similarity	NPC20505
0.881	High Similarity	NPC116864
0.881	High Similarity	NPC235260
0.881	High Similarity	NPC155763
0.881	High Similarity	NPC244776
0.8805	High Similarity	NPC4423
0.8805	High Similarity	NPC237440
0.8805	High Similarity	NPC84142
0.8805	High Similarity	NPC77325
0.8805	High Similarity	NPC270160
0.8802	High Similarity	NPC474024
0.8802	High Similarity	NPC218226
0.8802	High Similarity	NPC470456
0.8795	High Similarity	NPC471788
0.8795	High Similarity	NPC475888
0.8795	High Similarity	NPC62261
0.8788	High Similarity	NPC215612
0.8788	High Similarity	NPC472964
0.8788	High Similarity	NPC211107
0.8788	High Similarity	NPC474763
0.878	High Similarity	NPC24627
0.878	High Similarity	NPC470183
0.878	High Similarity	NPC282009
0.878	High Similarity	NPC287328
0.878	High Similarity	NPC472902
0.878	High Similarity	NPC36217
0.878	High Similarity	NPC130955
0.878	High Similarity	NPC470326
0.8773	High Similarity	NPC78302
0.8773	High Similarity	NPC470402
0.8773	High Similarity	NPC224137
0.8773	High Similarity	NPC75215
0.8773	High Similarity	NPC29841
0.8773	High Similarity	NPC471479
0.8773	High Similarity	NPC235215
0.8773	High Similarity	NPC176665
0.8773	High Similarity	NPC7973
0.8773	High Similarity	NPC163524
0.8773	High Similarity	NPC93376
0.8773	High Similarity	NPC110070
0.8773	High Similarity	NPC305663
0.8773	High Similarity	NPC287979
0.8773	High Similarity	NPC471515
0.8773	High Similarity	NPC227192
0.8773	High Similarity	NPC472438
0.8773	High Similarity	NPC203891
0.8773	High Similarity	NPC189179
0.8773	High Similarity	NPC101830
0.8765	High Similarity	NPC115760
0.8765	High Similarity	NPC101191
0.8765	High Similarity	NPC68727
0.8765	High Similarity	NPC145425
0.8765	High Similarity	NPC135277
0.8765	High Similarity	NPC234485
0.8765	High Similarity	NPC210094
0.8765	High Similarity	NPC477848
0.8765	High Similarity	NPC237435
0.8765	High Similarity	NPC49344
0.8765	High Similarity	NPC43211
0.8765	High Similarity	NPC264735
0.8758	High Similarity	NPC470338
0.8758	High Similarity	NPC470340
0.8758	High Similarity	NPC51824
0.8758	High Similarity	NPC470337
0.8758	High Similarity	NPC295646
0.8758	High Similarity	NPC268992
0.8758	High Similarity	NPC113608
0.8758	High Similarity	NPC279989
0.8758	High Similarity	NPC123886
0.8758	High Similarity	NPC82325
0.8757	High Similarity	NPC476370
0.875	High Similarity	NPC120099
0.875	High Similarity	NPC103509
0.875	High Similarity	NPC469619
0.875	High Similarity	NPC225434
0.875	High Similarity	NPC469670
0.875	High Similarity	NPC219904
0.875	High Similarity	NPC476771

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 NPC283041 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	954
0.2-0.3	2008
0.3-0.4	2564
0.4-0.5	1820
0.5-0.6	901
0.6-0.7	408
0.7-0.8	124
0.8-0.85	28
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8882	High Similarity	NPD3817	Phase 2
0.8765	High Similarity	NPD4338	Clinical (unspecified phase)
0.8675	High Similarity	NPD6232	Discontinued
0.8631	High Similarity	NPD7473	Discontinued
0.8598	High Similarity	NPD3882	Suspended
0.8589	High Similarity	NPD2801	Approved
0.8571	High Similarity	NPD6167	Clinical (unspecified phase)
0.8571	High Similarity	NPD6166	Phase 2
0.8571	High Similarity	NPD6168	Clinical (unspecified phase)
0.8538	High Similarity	NPD6797	Phase 2
0.8528	High Similarity	NPD1934	Approved
0.8488	Intermediate Similarity	NPD7251	Discontinued
0.8476	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD3818	Discontinued
0.8439	Intermediate Similarity	NPD7808	Phase 3
0.8434	Intermediate Similarity	NPD7075	Discontinued
0.8421	Intermediate Similarity	NPD7054	Approved
0.8415	Intermediate Similarity	NPD6801	Discontinued
0.8385	Intermediate Similarity	NPD1512	Approved
0.8372	Intermediate Similarity	NPD7472	Approved
0.8313	Intermediate Similarity	NPD5402	Approved
0.8293	Intermediate Similarity	NPD4380	Phase 2
0.8291	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD7074	Phase 3
0.8263	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD1511	Approved
0.8253	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD2532	Approved
0.821	Intermediate Similarity	NPD2534	Approved
0.821	Intermediate Similarity	NPD2533	Approved
0.8208	Intermediate Similarity	NPD5844	Phase 1
0.8167	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6799	Approved
0.8144	Intermediate Similarity	NPD7819	Suspended
0.8114	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5403	Approved
0.8103	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6599	Discontinued
0.8059	Intermediate Similarity	NPD6234	Discontinued
0.8056	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD1465	Phase 2
0.8025	Intermediate Similarity	NPD6190	Approved
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5401	Approved
0.7976	Intermediate Similarity	NPD37	Approved
0.7953	Intermediate Similarity	NPD919	Approved
0.7941	Intermediate Similarity	NPD4965	Approved
0.7941	Intermediate Similarity	NPD4967	Phase 2
0.7941	Intermediate Similarity	NPD4966	Approved
0.7911	Intermediate Similarity	NPD230	Phase 1
0.7907	Intermediate Similarity	NPD5494	Approved
0.7875	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6959	Discontinued
0.7845	Intermediate Similarity	NPD8150	Discontinued
0.7841	Intermediate Similarity	NPD7228	Approved
0.7841	Intermediate Similarity	NPD3751	Discontinued
0.7771	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7764	Intermediate Similarity	NPD1510	Phase 2
0.7759	Intermediate Similarity	NPD1247	Approved
0.7747	Intermediate Similarity	NPD8434	Phase 2
0.7744	Intermediate Similarity	NPD3750	Approved
0.7744	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD7435	Discontinued
0.7714	Intermediate Similarity	NPD3787	Discontinued
0.7706	Intermediate Similarity	NPD7411	Suspended
0.7674	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7685	Pre-registration
0.7665	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7199	Phase 2
0.7633	Intermediate Similarity	NPD1653	Approved
0.7622	Intermediate Similarity	NPD1549	Phase 2
0.7614	Intermediate Similarity	NPD5710	Approved
0.7614	Intermediate Similarity	NPD5711	Approved
0.7607	Intermediate Similarity	NPD2796	Approved
0.7588	Intermediate Similarity	NPD3226	Approved
0.7586	Intermediate Similarity	NPD3749	Approved
0.7579	Intermediate Similarity	NPD6782	Approved
0.7579	Intermediate Similarity	NPD6779	Approved
0.7579	Intermediate Similarity	NPD6778	Approved
0.7579	Intermediate Similarity	NPD6781	Approved
0.7579	Intermediate Similarity	NPD6777	Approved
0.7579	Intermediate Similarity	NPD6780	Approved
0.7579	Intermediate Similarity	NPD6776	Approved
0.7578	Intermediate Similarity	NPD447	Suspended
0.7574	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3926	Phase 2
0.7531	Intermediate Similarity	NPD1607	Approved
0.753	Intermediate Similarity	NPD4628	Phase 3
0.7528	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1240	Approved
0.7516	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7874	Approved
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7486	Intermediate Similarity	NPD8313	Approved
0.7486	Intermediate Similarity	NPD8312	Approved
0.747	Intermediate Similarity	NPD2800	Approved
0.7449	Intermediate Similarity	NPD8151	Discontinued
0.7439	Intermediate Similarity	NPD3748	Approved
0.7438	Intermediate Similarity	NPD3027	Phase 3
0.7429	Intermediate Similarity	NPD7768	Phase 2
0.7425	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1551	Phase 2
0.7377	Intermediate Similarity	NPD7240	Approved
0.7371	Intermediate Similarity	NPD7697	Approved
0.7371	Intermediate Similarity	NPD7698	Approved
0.7371	Intermediate Similarity	NPD7696	Phase 3
0.7368	Intermediate Similarity	NPD920	Approved
0.7349	Intermediate Similarity	NPD2346	Discontinued
0.7333	Intermediate Similarity	NPD7870	Phase 2
0.7333	Intermediate Similarity	NPD7871	Phase 2
0.7333	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8320	Phase 1
0.7333	Intermediate Similarity	NPD8319	Approved
0.7317	Intermediate Similarity	NPD6651	Approved
0.7316	Intermediate Similarity	NPD6535	Approved
0.7316	Intermediate Similarity	NPD6534	Approved
0.7312	Intermediate Similarity	NPD9494	Approved
0.731	Intermediate Similarity	NPD7701	Phase 2
0.7306	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1613	Approved
0.7294	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7390	Discontinued
0.7284	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5353	Approved
0.7262	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5953	Discontinued
0.722	Intermediate Similarity	NPD7907	Approved
0.7215	Intermediate Similarity	NPD9269	Phase 2
0.7202	Intermediate Similarity	NPD7699	Phase 2
0.7202	Intermediate Similarity	NPD7700	Phase 2
0.72	Intermediate Similarity	NPD7801	Approved
0.72	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7783	Phase 2
0.7195	Intermediate Similarity	NPD4060	Phase 1
0.7186	Intermediate Similarity	NPD6099	Approved
0.7186	Intermediate Similarity	NPD6100	Approved
0.7182	Intermediate Similarity	NPD5242	Approved
0.7167	Intermediate Similarity	NPD8127	Discontinued
0.716	Intermediate Similarity	NPD1243	Approved
0.7151	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7136	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2799	Discontinued
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.7122	Intermediate Similarity	NPD4665	Approved
0.7122	Intermediate Similarity	NPD4111	Phase 1
0.712	Intermediate Similarity	NPD7286	Phase 2
0.7118	Intermediate Similarity	NPD8166	Discontinued
0.7092	Intermediate Similarity	NPD2494	Approved
0.7092	Intermediate Similarity	NPD2493	Approved
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6798	Discontinued
0.7073	Intermediate Similarity	NPD2313	Discontinued
0.7059	Intermediate Similarity	NPD1652	Phase 2
0.7059	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1933	Approved
0.7048	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6355	Discontinued
0.7048	Intermediate Similarity	NPD5124	Phase 1
0.7041	Intermediate Similarity	NPD7266	Discontinued
0.7041	Intermediate Similarity	NPD5762	Approved
0.7041	Intermediate Similarity	NPD5763	Approved
0.7035	Intermediate Similarity	NPD3300	Phase 2
0.7033	Intermediate Similarity	NPD7229	Phase 3
0.703	Intermediate Similarity	NPD6233	Phase 2
0.702	Intermediate Similarity	NPD7680	Approved
0.7006	Intermediate Similarity	NPD6386	Approved
0.7006	Intermediate Similarity	NPD6385	Approved
0.7005	Intermediate Similarity	NPD3452	Approved
0.7005	Intermediate Similarity	NPD3450	Approved
0.7005	Intermediate Similarity	NPD8368	Discontinued
0.6994	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7458	Discontinued
0.6985	Remote Similarity	NPD4582	Approved
0.6985	Remote Similarity	NPD4583	Approved
0.6982	Remote Similarity	NPD5406	Approved
0.6982	Remote Similarity	NPD5404	Approved
0.6982	Remote Similarity	NPD5405	Approved
0.6982	Remote Similarity	NPD5408	Approved
0.697	Remote Similarity	NPD3764	Approved
0.6962	Remote Similarity	NPD9268	Approved
0.6957	Remote Similarity	NPD4379	Clinical (unspecified phase)

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