NPASS Compound

Structure

CID115249 OpenBabel06191715472D 28 30 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 -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 5.1962 0.0000 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 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 5.1962 -1.0000 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 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 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 -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 4.3301 1.5000 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 -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 4 1 0 0 0 0 2 11 1 0 0 0 0 4 5 2 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 12 1 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 27 1 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 13 22 1 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 21 1 1 0 0 0 17 28 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 19 24 2 0 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 3 1 6 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.14
Volume:	386.543
LogP:	2.719
LogD:	2.425
LogS:	-3.462
# Rotatable Bonds:	4
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.684
Synthetic Accessibility Score:	4.344
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.925
MDCK Permeability:	1.8037644622381777e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.782
30% Bioavailability (F30%):	0.24

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	94.97071075439453%
Volume Distribution (VD):	0.846
Pgp-substrate:	3.1816482543945312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.509
CYP2C19-inhibitor:	0.596
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.739
CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.953
CYP2D6-substrate:	0.324
CYP3A4-inhibitor:	0.839
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	5.225
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.402
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.278
Rat Oral Acute Toxicity:	0.397
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.948
Carcinogencity:	0.866
Eye Corrosion:	0.003
Eye Irritation:	0.878
Respiratory Toxicity:	0.25

Download Data

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

Natural Product: NPC115249

Natural Product ID:	NPC115249
*Common Name:**	Comazaphilone D
IUPAC Name:	[(6R,7R)-7-hydroxy-7-methyl-8-oxo-3-[(E)-prop-1-enyl]-5,6-dihydro-1H-isochromen-6-yl] 2,4-dihydroxy-6-methylbenzoate
Synonyms:	Comazaphilone D
Standard InCHIKey:	GIROBNCADSJPIJ-OQBWYENPSA-N
Standard InCHI:	InChI=1S/C21H22O7/c1-4-5-14-7-12-8-17(21(3,26)19(24)15(12)10-27-14)28-20(25)18-11(2)6-13(22)9-16(18)23/h4-7,9,17,22-23,26H,8,10H2,1-3H3/b5-4+/t17-,21-/m1/s1
SMILES:	C/C=C/C1=CC2=C(CO1)C(=O)[C@@](C)([C@@H](C2)OC(=O)c1c(C)cc(cc1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689198
PubChem CID:	51041753
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	=	51000.0	nM	PMID[575739]
NPT1209	Organism	Pseudomonas fluorescens	Pseudomonas fluorescens	MIC	=	16.0	ug.mL-1	PMID[575739]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[575739]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	256.0	ug.mL-1	PMID[575739]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	256.0	ug.mL-1	PMID[575739]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	256.0	ug.mL-1	PMID[575739]

☑ 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 NPC115249 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	345
0.1-0.2	1398
0.2-0.3	3433
0.3-0.4	7549
0.4-0.5	10391
0.5-0.6	4495
0.6-0.7	6148
0.7-0.8	7273
0.8-0.85	1418
0.85-0.9	198
0.9-0.95	29
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC137301
0.9863	High Similarity	NPC76041
0.9863	High Similarity	NPC184284
0.9862	High Similarity	NPC472891
0.9732	High Similarity	NPC472889
0.973	High Similarity	NPC472890
0.973	High Similarity	NPC69043
0.973	High Similarity	NPC208173
0.973	High Similarity	NPC478230
0.973	High Similarity	NPC170189
0.9728	High Similarity	NPC478224
0.9662	High Similarity	NPC478231
0.96	High Similarity	NPC478225
0.96	High Similarity	NPC246466
0.9597	High Similarity	NPC478221
0.9597	High Similarity	NPC317585
0.947	High Similarity	NPC478226
0.9392	High Similarity	NPC84142
0.9355	High Similarity	NPC191930
0.9329	High Similarity	NPC164762
0.929	High Similarity	NPC249181
0.9286	High Similarity	NPC317544
0.9267	High Similarity	NPC91809
0.9236	High Similarity	NPC283041
0.9172	High Similarity	NPC20237
0.915	High Similarity	NPC472050
0.9145	High Similarity	NPC471695
0.9128	High Similarity	NPC210320
0.911	High Similarity	NPC158634
0.9067	High Similarity	NPC215711
0.9067	High Similarity	NPC73411
0.9041	High Similarity	NPC158472
0.9038	High Similarity	NPC117985
0.9034	High Similarity	NPC33144
0.9034	High Similarity	NPC478200
0.9032	High Similarity	NPC470339
0.9007	High Similarity	NPC270160
0.9007	High Similarity	NPC237440
0.8986	High Similarity	NPC478202
0.898	High Similarity	NPC244923
0.8974	High Similarity	NPC472055
0.8973	High Similarity	NPC32360
0.8973	High Similarity	NPC247409
0.8973	High Similarity	NPC268052
0.8947	High Similarity	NPC56204
0.8938	High Similarity	NPC328321
0.8933	High Similarity	NPC473023
0.8926	High Similarity	NPC86373
0.8926	High Similarity	NPC280404
0.8926	High Similarity	NPC42540
0.8926	High Similarity	NPC210425
0.8926	High Similarity	NPC277426
0.8926	High Similarity	NPC151607
0.8919	High Similarity	NPC82913
0.8904	High Similarity	NPC191835
0.8889	High Similarity	NPC70016
0.8889	High Similarity	NPC215921
0.8882	High Similarity	NPC4423
0.8882	High Similarity	NPC77325
0.8867	High Similarity	NPC83272
0.8859	High Similarity	NPC159721
0.8851	High Similarity	NPC472035
0.8851	High Similarity	NPC313123
0.8851	High Similarity	NPC478217
0.8851	High Similarity	NPC53649
0.8851	High Similarity	NPC478201
0.8851	High Similarity	NPC472603
0.8844	High Similarity	NPC52358
0.8839	High Similarity	NPC471456
0.8839	High Similarity	NPC99381
0.8836	High Similarity	NPC70380
0.8831	High Similarity	NPC470340
0.8816	High Similarity	NPC94781
0.88	High Similarity	NPC478203
0.88	High Similarity	NPC126882
0.88	High Similarity	NPC210966
0.88	High Similarity	NPC103910
0.8792	High Similarity	NPC474385
0.8792	High Similarity	NPC322112
0.8784	High Similarity	NPC472600
0.8784	High Similarity	NPC156872
0.8784	High Similarity	NPC472601
0.8776	High Similarity	NPC94248
0.8776	High Similarity	NPC212693
0.8776	High Similarity	NPC472602
0.8774	High Similarity	NPC155686
0.8774	High Similarity	NPC192189
0.8767	High Similarity	NPC235115
0.8766	High Similarity	NPC46882
0.8766	High Similarity	NPC205918
0.8766	High Similarity	NPC200773
0.8766	High Similarity	NPC240768
0.8766	High Similarity	NPC132990
0.8759	High Similarity	NPC175943
0.8758	High Similarity	NPC44378
0.8758	High Similarity	NPC473094
0.8758	High Similarity	NPC280753
0.875	High Similarity	NPC166583
0.875	High Similarity	NPC53362
0.875	High Similarity	NPC472036
0.8742	High Similarity	NPC257558
0.8742	High Similarity	NPC472034
0.8733	High Similarity	NPC51106
0.8733	High Similarity	NPC472006
0.8733	High Similarity	NPC471731
0.8725	High Similarity	NPC472605
0.8725	High Similarity	NPC1704
0.8725	High Similarity	NPC472604
0.8725	High Similarity	NPC475730
0.8725	High Similarity	NPC67650
0.8716	High Similarity	NPC92655
0.871	High Similarity	NPC470338
0.871	High Similarity	NPC256141
0.871	High Similarity	NPC167903
0.871	High Similarity	NPC268992
0.871	High Similarity	NPC113608
0.871	High Similarity	NPC51824
0.871	High Similarity	NPC470337
0.8707	High Similarity	NPC71256
0.8704	High Similarity	NPC473095
0.8704	High Similarity	NPC473096
0.8701	High Similarity	NPC158866
0.8701	High Similarity	NPC180351
0.8701	High Similarity	NPC469619
0.8701	High Similarity	NPC469670
0.8701	High Similarity	NPC179178
0.8693	High Similarity	NPC37139
0.8693	High Similarity	NPC240253
0.8693	High Similarity	NPC471642
0.8693	High Similarity	NPC240622
0.8693	High Similarity	NPC471641
0.869	High Similarity	NPC153783
0.8684	High Similarity	NPC260946
0.8684	High Similarity	NPC107625
0.8684	High Similarity	NPC472033
0.8675	High Similarity	NPC257025
0.8675	High Similarity	NPC475201
0.8667	High Similarity	NPC471733
0.8662	High Similarity	NPC227062
0.8662	High Similarity	NPC478027
0.8658	High Similarity	NPC155205
0.8654	High Similarity	NPC472799
0.8649	High Similarity	NPC126739
0.8649	High Similarity	NPC9121
0.8649	High Similarity	NPC177307
0.8649	High Similarity	NPC197666
0.8639	High Similarity	NPC50455
0.8636	High Similarity	NPC120171
0.8634	High Similarity	NPC472049
0.8627	High Similarity	NPC259632
0.8627	High Similarity	NPC476463
0.8627	High Similarity	NPC81835
0.8618	High Similarity	NPC312789
0.8616	High Similarity	NPC243701
0.8616	High Similarity	NPC470810
0.8609	High Similarity	NPC21873
0.8609	High Similarity	NPC469542
0.8609	High Similarity	NPC472610
0.8609	High Similarity	NPC354984
0.8608	High Similarity	NPC473395
0.86	High Similarity	NPC130485
0.8599	High Similarity	NPC16082
0.8599	High Similarity	NPC304207
0.8599	High Similarity	NPC79998
0.8599	High Similarity	NPC56786
0.8599	High Similarity	NPC476169
0.8599	High Similarity	NPC80534
0.8599	High Similarity	NPC68727
0.8599	High Similarity	NPC259710
0.8599	High Similarity	NPC217706
0.8599	High Similarity	NPC48579
0.8599	High Similarity	NPC207809
0.8599	High Similarity	NPC82592
0.8599	High Similarity	NPC473241
0.8599	High Similarity	NPC108937
0.8599	High Similarity	NPC279218
0.8598	High Similarity	NPC472620
0.8591	High Similarity	NPC105456
0.8591	High Similarity	NPC295339
0.8591	High Similarity	NPC139634
0.8591	High Similarity	NPC88269
0.859	High Similarity	NPC271681
0.859	High Similarity	NPC210597
0.859	High Similarity	NPC180944
0.8589	High Similarity	NPC472619
0.8581	High Similarity	NPC295036
0.8581	High Similarity	NPC194579
0.8581	High Similarity	NPC178467
0.8581	High Similarity	NPC65837
0.8581	High Similarity	NPC474771
0.8581	High Similarity	NPC135837
0.8581	High Similarity	NPC150928
0.8581	High Similarity	NPC149372
0.8581	High Similarity	NPC474849
0.858	High Similarity	NPC43319
0.858	High Similarity	NPC165460
0.8571	High Similarity	NPC27407
0.8571	High Similarity	NPC186686
0.8562	High Similarity	NPC225173
0.8562	High Similarity	NPC202112

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 NPC115249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	866
0.2-0.3	1806
0.3-0.4	2623
0.4-0.5	1911
0.5-0.6	1063
0.6-0.7	416
0.7-0.8	148
0.8-0.85	19
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8591	High Similarity	NPD970	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD7075	Discontinued
0.8481	Intermediate Similarity	NPD3817	Phase 2
0.8418	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD2532	Approved
0.8377	Intermediate Similarity	NPD2533	Approved
0.8377	Intermediate Similarity	NPD2534	Approved
0.8354	Intermediate Similarity	NPD6801	Discontinued
0.8344	Intermediate Similarity	NPD4380	Phase 2
0.8312	Intermediate Similarity	NPD6799	Approved
0.8302	Intermediate Similarity	NPD7819	Suspended
0.8302	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6232	Discontinued
0.8242	Intermediate Similarity	NPD7473	Discontinued
0.8239	Intermediate Similarity	NPD1934	Approved
0.8228	Intermediate Similarity	NPD6599	Discontinued
0.8205	Intermediate Similarity	NPD1512	Approved
0.8187	Intermediate Similarity	NPD2801	Approved
0.8137	Intermediate Similarity	NPD5402	Approved
0.8086	Intermediate Similarity	NPD3882	Suspended
0.8077	Intermediate Similarity	NPD1511	Approved
0.8072	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6166	Phase 2
0.8059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6797	Phase 2
0.8038	Intermediate Similarity	NPD5403	Approved
0.8037	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1510	Phase 2
0.8	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD8150	Discontinued
0.7953	Intermediate Similarity	NPD7808	Phase 3
0.7947	Intermediate Similarity	NPD230	Phase 1
0.7929	Intermediate Similarity	NPD7054	Approved
0.7929	Intermediate Similarity	NPD5844	Phase 1
0.7922	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD5401	Approved
0.7908	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7472	Approved
0.7871	Intermediate Similarity	NPD1549	Phase 2
0.787	Intermediate Similarity	NPD3818	Discontinued
0.7866	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2796	Approved
0.784	Intermediate Similarity	NPD7411	Suspended
0.7805	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD7074	Phase 3
0.7778	Intermediate Similarity	NPD1607	Approved
0.7771	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1240	Approved
0.7742	Intermediate Similarity	NPD2935	Discontinued
0.7738	Intermediate Similarity	NPD5711	Approved
0.7738	Intermediate Similarity	NPD5710	Approved
0.7736	Intermediate Similarity	NPD7390	Discontinued
0.7722	Intermediate Similarity	NPD6190	Approved
0.7711	Intermediate Similarity	NPD3749	Approved
0.7677	Intermediate Similarity	NPD3748	Approved
0.7665	Intermediate Similarity	NPD919	Approved
0.7661	Intermediate Similarity	NPD3751	Discontinued
0.7658	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7651	Intermediate Similarity	NPD7768	Phase 2
0.7647	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1551	Phase 2
0.7619	Intermediate Similarity	NPD5494	Approved
0.7607	Intermediate Similarity	NPD3226	Approved
0.7595	Intermediate Similarity	NPD2800	Approved
0.7584	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8434	Phase 2
0.7568	Intermediate Similarity	NPD7435	Discontinued
0.756	Intermediate Similarity	NPD6234	Discontinued
0.7532	Intermediate Similarity	NPD943	Approved
0.753	Intermediate Similarity	NPD1465	Phase 2
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7516	Intermediate Similarity	NPD5406	Approved
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5408	Approved
0.7516	Intermediate Similarity	NPD5404	Approved
0.7516	Intermediate Similarity	NPD5405	Approved
0.7514	Intermediate Similarity	NPD6535	Approved
0.7514	Intermediate Similarity	NPD6534	Approved
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.7485	Intermediate Similarity	NPD920	Approved
0.7484	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD37	Approved
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7466	Intermediate Similarity	NPD9545	Approved
0.7453	Intermediate Similarity	NPD3300	Phase 2
0.744	Intermediate Similarity	NPD4965	Approved
0.744	Intermediate Similarity	NPD4966	Approved
0.744	Intermediate Similarity	NPD4967	Phase 2
0.7436	Intermediate Similarity	NPD6651	Approved
0.7433	Intermediate Similarity	NPD8319	Approved
0.7433	Intermediate Similarity	NPD8320	Phase 1
0.7405	Intermediate Similarity	NPD6099	Approved
0.7405	Intermediate Similarity	NPD6100	Approved
0.7403	Intermediate Similarity	NPD3764	Approved
0.7401	Intermediate Similarity	NPD8312	Approved
0.7401	Intermediate Similarity	NPD8313	Approved
0.7391	Intermediate Similarity	NPD7700	Phase 2
0.7391	Intermediate Similarity	NPD7699	Phase 2
0.7384	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1201	Approved
0.7375	Intermediate Similarity	NPD1243	Approved
0.7368	Intermediate Similarity	NPD1247	Approved
0.7362	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7874	Approved
0.7329	Intermediate Similarity	NPD9493	Approved
0.7308	Intermediate Similarity	NPD4060	Phase 1
0.7303	Intermediate Similarity	NPD1470	Approved
0.7287	Intermediate Similarity	NPD7698	Approved
0.7287	Intermediate Similarity	NPD7696	Phase 3
0.7287	Intermediate Similarity	NPD7697	Approved
0.7277	Intermediate Similarity	NPD8151	Discontinued
0.7273	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7199	Phase 2
0.7261	Intermediate Similarity	NPD447	Suspended
0.7257	Intermediate Similarity	NPD7228	Approved
0.7249	Intermediate Similarity	NPD7870	Phase 2
0.7249	Intermediate Similarity	NPD7871	Phase 2
0.7233	Intermediate Similarity	NPD2799	Discontinued
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.7232	Intermediate Similarity	NPD5953	Discontinued
0.7225	Intermediate Similarity	NPD7701	Phase 2
0.7222	Intermediate Similarity	NPD8166	Discontinued
0.7219	Intermediate Similarity	NPD9269	Phase 2
0.7216	Intermediate Similarity	NPD7286	Phase 2
0.7186	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7458	Discontinued
0.7184	Intermediate Similarity	NPD3926	Phase 2
0.7179	Intermediate Similarity	NPD6798	Discontinued
0.7179	Intermediate Similarity	NPD2313	Discontinued
0.716	Intermediate Similarity	NPD1652	Phase 2
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD422	Phase 1
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7236	Approved
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7126	Intermediate Similarity	NPD1653	Approved
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7113	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7783	Phase 2
0.7113	Intermediate Similarity	NPD7801	Approved
0.7105	Intermediate Similarity	NPD9717	Approved
0.7095	Intermediate Similarity	NPD7685	Pre-registration
0.7095	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1203	Approved
0.7076	Intermediate Similarity	NPD4288	Approved
0.707	Intermediate Similarity	NPD3268	Approved
0.707	Intermediate Similarity	NPD411	Approved
0.7067	Intermediate Similarity	NPD9268	Approved
0.7053	Intermediate Similarity	NPD6823	Phase 2
0.7052	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6832	Phase 2
0.7045	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2403	Approved
0.7044	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5762	Approved
0.7037	Intermediate Similarity	NPD5763	Approved
0.7032	Intermediate Similarity	NPD2798	Approved
0.7031	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4626	Approved
0.7019	Intermediate Similarity	NPD4308	Phase 3
0.7012	Intermediate Similarity	NPD7003	Approved
0.7006	Intermediate Similarity	NPD6273	Approved
0.7006	Intermediate Similarity	NPD3027	Phase 3
0.7006	Intermediate Similarity	NPD4625	Phase 3
0.7	Intermediate Similarity	NPD8368	Discontinued
0.6989	Remote Similarity	NPD6212	Phase 3
0.6989	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6213	Phase 3
0.6981	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1613	Approved
0.6977	Remote Similarity	NPD5353	Approved
0.6975	Remote Similarity	NPD2438	Suspended
0.6968	Remote Similarity	NPD2797	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