NPASS Compound

Structure

CID191930 OpenBabel06191715572D 30 32 0 0 1 0 0 0 0 0999 V2000 0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 5.1962 -1.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 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 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 4.3301 1.5000 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 1.7321 -0.0000 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 1 0 0 0 16 30 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 24 1 0 0 0 0 19 28 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 30 1 0 0 0 0 22 3 1 6 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.15
Volume:	412.629
LogP:	1.933
LogD:	1.999
LogS:	-3.529
# 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:	4.403
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:	-4.815
MDCK Permeability:	1.65371093316935e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.05
20% Bioavailability (F20%):	0.404
30% Bioavailability (F30%):	0.102

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	94.51366424560547%
Volume Distribution (VD):	0.821
Pgp-substrate:	6.245826721191406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.656
CYP2C19-inhibitor:	0.334
CYP2C19-substrate:	0.193
CYP2C9-inhibitor:	0.665
CYP2C9-substrate:	0.795
CYP2D6-inhibitor:	0.901
CYP2D6-substrate:	0.285
CYP3A4-inhibitor:	0.679
CYP3A4-substrate:	0.406

ADMET: Excretion

Clearance (CL):	3.575
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.455
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.436
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.937
Carcinogencity:	0.791
Eye Corrosion:	0.003
Eye Irritation:	0.837
Respiratory Toxicity:	0.175

Download Data

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

Natural Product: NPC191930

Natural Product ID:	NPC191930
*Common Name:**	Comazaphilone E
IUPAC Name:	[(6R,7R)-7-hydroxy-7-methyl-8-oxo-3-[(E)-prop-1-enyl]-5,6-dihydro-1H-isochromen-6-yl] 3,4-dihydroxy-2-methoxy-6-methylbenzoate
Synonyms:	Comazaphilone E
Standard InCHIKey:	VWYGBXGOGQHZHM-JBAXFHHXSA-N
Standard InCHI:	InChI=1S/C22H24O8/c1-5-6-13-8-12-9-16(22(3,27)20(25)14(12)10-29-13)30-21(26)17-11(2)7-15(23)18(24)19(17)28-4/h5-8,16,23-24,27H,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)OC(=O)c1c(C)cc(c(c1OC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689199
PubChem CID:	51041754
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
IC50	1
MIC	5

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1312	Cell Line	SW1990	Homo sapiens	IC50	=	26000.0	nM	PMID[508255]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	16.0	ug.mL-1	PMID[508255]
NPT1209	Organism	Pseudomonas fluorescens	Pseudomonas fluorescens	MIC	=	32.0	ug.mL-1	PMID[508255]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	256.0	ug.mL-1	PMID[508255]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	256.0	ug.mL-1	PMID[508255]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	256.0	ug.mL-1	PMID[508255]

☑ 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 NPC191930 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	382
0.1-0.2	1556
0.2-0.3	3892
0.3-0.4	8316
0.4-0.5	9579
0.5-0.6	4092
0.6-0.7	5341
0.7-0.8	6900
0.8-0.85	2210
0.85-0.9	394
0.9-0.95	31
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC249181
0.9873	High Similarity	NPC283041
0.9809	High Similarity	NPC20237
0.9419	High Similarity	NPC137301
0.9363	High Similarity	NPC246466
0.9355	High Similarity	NPC115249
0.9295	High Similarity	NPC478231
0.9241	High Similarity	NPC472889
0.9236	High Similarity	NPC472890
0.9236	High Similarity	NPC69043
0.9236	High Similarity	NPC317585
0.9236	High Similarity	NPC478230
0.9231	High Similarity	NPC76041
0.9231	High Similarity	NPC184284
0.9231	High Similarity	NPC478224
0.9226	High Similarity	NPC472891
0.9125	High Similarity	NPC472055
0.9119	High Similarity	NPC478225
0.9114	High Similarity	NPC170189
0.9114	High Similarity	NPC82592
0.9114	High Similarity	NPC478221
0.9114	High Similarity	NPC16286
0.9114	High Similarity	NPC208173
0.9114	High Similarity	NPC16082
0.9114	High Similarity	NPC79998
0.9085	High Similarity	NPC328321
0.9068	High Similarity	NPC117985
0.9062	High Similarity	NPC477410
0.9062	High Similarity	NPC470339
0.9057	High Similarity	NPC472050
0.9057	High Similarity	NPC227062
0.9057	High Similarity	NPC150227
0.9051	High Similarity	NPC281477
0.9	High Similarity	NPC77679
0.9	High Similarity	NPC84935
0.9	High Similarity	NPC478226
0.9	High Similarity	NPC190020
0.8994	High Similarity	NPC199926
0.8981	High Similarity	NPC96501
0.8963	High Similarity	NPC43319
0.8957	High Similarity	NPC186686
0.8957	High Similarity	NPC476822
0.8951	High Similarity	NPC317544
0.8951	High Similarity	NPC112418
0.8951	High Similarity	NPC87431
0.8944	High Similarity	NPC280680
0.8941	High Similarity	NPC182693
0.8938	High Similarity	NPC197751
0.8938	High Similarity	NPC54928
0.8924	High Similarity	NPC215921
0.8924	High Similarity	NPC70016
0.891	High Similarity	NPC210320
0.8909	High Similarity	NPC218226
0.8909	High Similarity	NPC473094
0.8902	High Similarity	NPC62261
0.8896	High Similarity	NPC474763
0.8896	High Similarity	NPC471745
0.8889	High Similarity	NPC161947
0.8889	High Similarity	NPC130955
0.8889	High Similarity	NPC471744
0.8889	High Similarity	NPC36217
0.8889	High Similarity	NPC155302
0.8889	High Similarity	NPC155101
0.8882	High Similarity	NPC189179
0.8882	High Similarity	NPC224137
0.8882	High Similarity	NPC75215
0.8882	High Similarity	NPC227192
0.8882	High Similarity	NPC93376
0.8875	High Similarity	NPC80534
0.8875	High Similarity	NPC56786
0.8875	High Similarity	NPC234485
0.8875	High Similarity	NPC99381
0.8868	High Similarity	NPC295646
0.8861	High Similarity	NPC164762
0.8855	High Similarity	NPC473095
0.8855	High Similarity	NPC473096
0.8855	High Similarity	NPC188079
0.8854	High Similarity	NPC73411
0.8854	High Similarity	NPC215711
0.8848	High Similarity	NPC477517
0.8848	High Similarity	NPC329119
0.8841	High Similarity	NPC472625
0.8841	High Similarity	NPC41301
0.8834	High Similarity	NPC201560
0.8834	High Similarity	NPC474779
0.8834	High Similarity	NPC471499
0.8834	High Similarity	NPC173137
0.8827	High Similarity	NPC176300
0.8827	High Similarity	NPC253634
0.8827	High Similarity	NPC300943
0.8827	High Similarity	NPC261004
0.8827	High Similarity	NPC105242
0.8827	High Similarity	NPC315157
0.8827	High Similarity	NPC115798
0.8827	High Similarity	NPC22472
0.8827	High Similarity	NPC18772
0.8827	High Similarity	NPC4481
0.8827	High Similarity	NPC204854
0.8827	High Similarity	NPC19687
0.8827	High Similarity	NPC55738
0.8827	High Similarity	NPC152166
0.8827	High Similarity	NPC9609
0.8827	High Similarity	NPC288669
0.8827	High Similarity	NPC7846
0.8827	High Similarity	NPC18607
0.8827	High Similarity	NPC25495
0.8827	High Similarity	NPC191459
0.8827	High Similarity	NPC143828
0.8827	High Similarity	NPC130894
0.882	High Similarity	NPC49824
0.882	High Similarity	NPC98661
0.882	High Similarity	NPC24640
0.882	High Similarity	NPC474520
0.882	High Similarity	NPC265511
0.882	High Similarity	NPC247017
0.8812	High Similarity	NPC144801
0.8812	High Similarity	NPC236223
0.8812	High Similarity	NPC162351
0.8812	High Similarity	NPC43872
0.8812	High Similarity	NPC238672
0.8812	High Similarity	NPC127172
0.8812	High Similarity	NPC116850
0.8812	High Similarity	NPC78326
0.8812	High Similarity	NPC58382
0.8812	High Similarity	NPC270620
0.8812	High Similarity	NPC179126
0.8812	High Similarity	NPC192189
0.8812	High Similarity	NPC155686
0.8812	High Similarity	NPC291510
0.8812	High Similarity	NPC197188
0.881	High Similarity	NPC4390
0.8805	High Similarity	NPC125062
0.8805	High Similarity	NPC200773
0.8805	High Similarity	NPC252933
0.8805	High Similarity	NPC240768
0.8805	High Similarity	NPC54394
0.8805	High Similarity	NPC91809
0.8805	High Similarity	NPC200740
0.8805	High Similarity	NPC28274
0.8805	High Similarity	NPC50403
0.8805	High Similarity	NPC133953
0.8802	High Similarity	NPC109827
0.8802	High Similarity	NPC124470
0.8797	High Similarity	NPC4423
0.8797	High Similarity	NPC77325
0.8797	High Similarity	NPC270160
0.8797	High Similarity	NPC237440
0.8797	High Similarity	NPC84142
0.8795	High Similarity	NPC474024
0.8795	High Similarity	NPC158761
0.8788	High Similarity	NPC470457
0.8788	High Similarity	NPC88243
0.8788	High Similarity	NPC472049
0.8788	High Similarity	NPC239752
0.8788	High Similarity	NPC475888
0.8788	High Similarity	NPC472450
0.8788	High Similarity	NPC471788
0.8788	High Similarity	NPC327652
0.8788	High Similarity	NPC293319
0.8788	High Similarity	NPC303174
0.8788	High Similarity	NPC224280
0.8788	High Similarity	NPC275780
0.878	High Similarity	NPC474150
0.878	High Similarity	NPC472964
0.878	High Similarity	NPC211107
0.878	High Similarity	NPC201800
0.878	High Similarity	NPC215612
0.878	High Similarity	NPC48860
0.878	High Similarity	NPC474162
0.8773	High Similarity	NPC287328
0.8773	High Similarity	NPC282009
0.8773	High Similarity	NPC472902
0.8773	High Similarity	NPC192686
0.8773	High Similarity	NPC471973
0.8773	High Similarity	NPC118256
0.8773	High Similarity	NPC470183
0.8773	High Similarity	NPC24627
0.8773	High Similarity	NPC470326
0.8773	High Similarity	NPC119209
0.8773	High Similarity	NPC474960
0.8765	High Similarity	NPC7973
0.8765	High Similarity	NPC163524
0.8765	High Similarity	NPC110070
0.8765	High Similarity	NPC35598
0.8765	High Similarity	NPC287979
0.8765	High Similarity	NPC305663
0.8765	High Similarity	NPC472438
0.8765	High Similarity	NPC471515
0.8765	High Similarity	NPC470402
0.8765	High Similarity	NPC273843
0.8765	High Similarity	NPC203891
0.8765	High Similarity	NPC78302
0.8765	High Similarity	NPC176665
0.8765	High Similarity	NPC29841
0.8765	High Similarity	NPC136674
0.8765	High Similarity	NPC222689
0.8765	High Similarity	NPC471479
0.8765	High Similarity	NPC27337
0.8765	High Similarity	NPC101830
0.8765	High Similarity	NPC235215

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 NPC191930 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	957
0.2-0.3	1974
0.3-0.4	2545
0.4-0.5	1831
0.5-0.6	934
0.6-0.7	411
0.7-0.8	131
0.8-0.85	23
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8875	High Similarity	NPD3817	Phase 2
0.878	High Similarity	NPD6232	Discontinued
0.8735	High Similarity	NPD7473	Discontinued
0.8696	High Similarity	NPD2801	Approved
0.8647	High Similarity	NPD4338	Clinical (unspecified phase)
0.8634	High Similarity	NPD1934	Approved
0.8589	High Similarity	NPD3882	Suspended
0.858	High Similarity	NPD2393	Clinical (unspecified phase)
0.8563	High Similarity	NPD6166	Phase 2
0.8563	High Similarity	NPD6167	Clinical (unspecified phase)
0.8563	High Similarity	NPD6168	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD1512	Approved
0.8462	Intermediate Similarity	NPD3818	Discontinued
0.8424	Intermediate Similarity	NPD7075	Discontinued
0.8421	Intermediate Similarity	NPD6797	Phase 2
0.8412	Intermediate Similarity	NPD7054	Approved
0.8397	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD7251	Discontinued
0.8365	Intermediate Similarity	NPD1511	Approved
0.8364	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD7472	Approved
0.8324	Intermediate Similarity	NPD7808	Phase 3
0.8313	Intermediate Similarity	NPD2534	Approved
0.8313	Intermediate Similarity	NPD2533	Approved
0.8313	Intermediate Similarity	NPD2532	Approved
0.8293	Intermediate Similarity	NPD6801	Discontinued
0.8282	Intermediate Similarity	NPD4380	Phase 2
0.8256	Intermediate Similarity	NPD7074	Phase 3
0.8242	Intermediate Similarity	NPD7819	Suspended
0.8242	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD5844	Phase 1
0.8193	Intermediate Similarity	NPD5402	Approved
0.8155	Intermediate Similarity	NPD6234	Discontinued
0.8146	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD1465	Phase 2
0.8103	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6599	Discontinued
0.8056	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD230	Phase 1
0.8	Intermediate Similarity	NPD5494	Approved
0.7989	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5403	Approved
0.7975	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD37	Approved
0.7953	Intermediate Similarity	NPD6959	Discontinued
0.7941	Intermediate Similarity	NPD919	Approved
0.7929	Intermediate Similarity	NPD4966	Approved
0.7929	Intermediate Similarity	NPD4967	Phase 2
0.7929	Intermediate Similarity	NPD4965	Approved
0.7901	Intermediate Similarity	NPD6190	Approved
0.7866	Intermediate Similarity	NPD5401	Approved
0.7862	Intermediate Similarity	NPD1510	Phase 2
0.784	Intermediate Similarity	NPD3750	Approved
0.7833	Intermediate Similarity	NPD8150	Discontinued
0.7829	Intermediate Similarity	NPD7228	Approved
0.7798	Intermediate Similarity	NPD7411	Suspended
0.7765	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6559	Discontinued
0.7746	Intermediate Similarity	NPD1247	Approved
0.7735	Intermediate Similarity	NPD8434	Phase 2
0.773	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3751	Discontinued
0.7716	Intermediate Similarity	NPD1549	Phase 2
0.7702	Intermediate Similarity	NPD2796	Approved
0.7701	Intermediate Similarity	NPD5711	Approved
0.7701	Intermediate Similarity	NPD5710	Approved
0.7679	Intermediate Similarity	NPD3226	Approved
0.7674	Intermediate Similarity	NPD3749	Approved
0.7673	Intermediate Similarity	NPD447	Suspended
0.7665	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD3926	Phase 2
0.7654	Intermediate Similarity	NPD7685	Pre-registration
0.7644	Intermediate Similarity	NPD7199	Phase 2
0.7632	Intermediate Similarity	NPD7435	Discontinued
0.7625	Intermediate Similarity	NPD1607	Approved
0.7619	Intermediate Similarity	NPD1653	Approved
0.7614	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD943	Approved
0.761	Intermediate Similarity	NPD1240	Approved
0.76	Intermediate Similarity	NPD3787	Discontinued
0.7593	Intermediate Similarity	NPD2935	Discontinued
0.7566	Intermediate Similarity	NPD6777	Approved
0.7566	Intermediate Similarity	NPD6782	Approved
0.7566	Intermediate Similarity	NPD6778	Approved
0.7566	Intermediate Similarity	NPD6781	Approved
0.7566	Intermediate Similarity	NPD6776	Approved
0.7566	Intermediate Similarity	NPD6780	Approved
0.7566	Intermediate Similarity	NPD6779	Approved
0.7561	Intermediate Similarity	NPD2800	Approved
0.7531	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7473	Intermediate Similarity	NPD8312	Approved
0.7473	Intermediate Similarity	NPD8313	Approved
0.7456	Intermediate Similarity	NPD920	Approved
0.7439	Intermediate Similarity	NPD2346	Discontinued
0.7436	Intermediate Similarity	NPD8151	Discontinued
0.7423	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3027	Phase 3
0.7407	Intermediate Similarity	NPD6651	Approved
0.7405	Intermediate Similarity	NPD9494	Approved
0.7398	Intermediate Similarity	NPD7874	Approved
0.7398	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7390	Discontinued
0.7375	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7240	Approved
0.7358	Intermediate Similarity	NPD7698	Approved
0.7358	Intermediate Similarity	NPD7696	Phase 3
0.7358	Intermediate Similarity	NPD7697	Approved
0.7356	Intermediate Similarity	NPD5353	Approved
0.7349	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7871	Phase 2
0.732	Intermediate Similarity	NPD7870	Phase 2
0.7316	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5953	Discontinued
0.7308	Intermediate Similarity	NPD9269	Phase 2
0.7302	Intermediate Similarity	NPD6535	Approved
0.7302	Intermediate Similarity	NPD6534	Approved
0.7296	Intermediate Similarity	NPD7701	Phase 2
0.7284	Intermediate Similarity	NPD1613	Approved
0.7284	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD6099	Approved
0.7263	Intermediate Similarity	NPD5242	Approved
0.7246	Intermediate Similarity	NPD1243	Approved
0.7231	Intermediate Similarity	NPD8320	Phase 1
0.7231	Intermediate Similarity	NPD8319	Approved
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2799	Discontinued
0.7206	Intermediate Similarity	NPD7907	Approved
0.7202	Intermediate Similarity	NPD8166	Discontinued
0.7198	Intermediate Similarity	NPD7286	Phase 2
0.7188	Intermediate Similarity	NPD7700	Phase 2
0.7188	Intermediate Similarity	NPD7699	Phase 2
0.7186	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7783	Phase 2
0.7186	Intermediate Similarity	NPD7801	Approved
0.7178	Intermediate Similarity	NPD4060	Phase 1
0.716	Intermediate Similarity	NPD2313	Discontinued
0.7151	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1933	Approved
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.7127	Intermediate Similarity	NPD2403	Approved
0.7118	Intermediate Similarity	NPD3300	Phase 2
0.7111	Intermediate Similarity	NPD7229	Phase 3
0.7108	Intermediate Similarity	NPD4111	Phase 1
0.7108	Intermediate Similarity	NPD4665	Approved
0.7108	Intermediate Similarity	NPD7033	Discontinued
0.7086	Intermediate Similarity	NPD6386	Approved
0.7086	Intermediate Similarity	NPD6385	Approved
0.7081	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD2494	Approved
0.7077	Intermediate Similarity	NPD2493	Approved
0.7069	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7066	Intermediate Similarity	NPD5406	Approved
0.7066	Intermediate Similarity	NPD5404	Approved
0.7066	Intermediate Similarity	NPD5405	Approved
0.7066	Intermediate Similarity	NPD5408	Approved
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3764	Approved
0.7055	Intermediate Similarity	NPD6798	Discontinued
0.7053	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD9268	Approved
0.7044	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1652	Phase 2
0.7039	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7035	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6355	Discontinued
0.703	Intermediate Similarity	NPD5124	Phase 1
0.7025	Intermediate Similarity	NPD422	Phase 1
0.7024	Intermediate Similarity	NPD7266	Discontinued
0.7012	Intermediate Similarity	NPD6233	Phase 2
0.7005	Intermediate Similarity	NPD7680	Approved
0.699	Remote Similarity	NPD3450	Approved
0.699	Remote Similarity	NPD3452	Approved
0.6987	Remote Similarity	NPD9545	Approved
0.6981	Remote Similarity	NPD9717	Approved
0.697	Remote Similarity	NPD4583	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