NPASS Compound

Structure

CID166480 OpenBabel06191715542D 28 29 0 0 0 0 0 0 0 0999 V2000 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 2.5981 3.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 -1.7321 -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 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 0.0000 -1.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 16 1 0 0 0 0 7 18 2 0 0 0 0 8 10 1 0 0 0 0 8 13 2 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 21 2 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 27 2 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.18
Volume:	409.474
LogP:	6.419
LogD:	3.566
LogS:	-3.314
# Rotatable Bonds:	6
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	2.937
Fsp3:	0.261
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:	-5.142
MDCK Permeability:	1.3826940630679019e-05
Pgp-inhibitor:	0.495
Pgp-substrate:	0.048
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	99.4625015258789%
Volume Distribution (VD):	1.62
Pgp-substrate:	2.671516180038452%

ADMET: Metabolism

CYP1A2-inhibitor:	0.88
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.859
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.825
CYP2C9-substrate:	0.755
CYP2D6-inhibitor:	0.898
CYP2D6-substrate:	0.22
CYP3A4-inhibitor:	0.291
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	15.628
Half-life (T1/2):	0.362

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.662
Drug-inuced Liver Injury (DILI):	0.788
AMES Toxicity:	0.491
Rat Oral Acute Toxicity:	0.285
Maximum Recommended Daily Dose:	0.241
Skin Sensitization:	0.921
Carcinogencity:	0.147
Eye Corrosion:	0.003
Eye Irritation:	0.874
Respiratory Toxicity:	0.219

Download Data

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

Natural Product: NPC166480

Natural Product ID:	NPC166480
*Common Name:**	Cudraphenone D
IUPAC Name:	[3-hydroxy-2-(3-methylbut-2-enyl)phenyl]-[2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl]methanone
Synonyms:	Cudraphenone D
Standard InCHIKey:	RJRXEFUEAJKCQJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H26O5/c1-13(2)8-10-15-16(6-5-7-18(15)24)22(27)21-20(26)12-19(25)17(23(21)28)11-9-14(3)4/h5-9,12,24-26,28H,10-11H2,1-4H3
SMILES:	CC(=CCc1c(cccc1O)C(=O)c1c(cc(c(CC=C(C)C)c1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458135
PubChem CID:	509243
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*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
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[11170668]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[12932139]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23156	Maclura cochinchinensis	Species	Moraceae	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	8
Others	4

Activity Type	# Activity
Cell Line	2
Organism	9
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	=	52000.0	nM	PMID[551402]
NPT924	Cell Line	HSC-2	Homo sapiens	Ratio	=	3.7	n.a.	PMID[551402]
NPT27	Others	Unspecified		CC50	=	190000.0	nM	PMID[551402]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	11.0	mm	PMID[551403]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	2.0	ug.mL-1	PMID[551403]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	4.0	ug.mL-1	PMID[551403]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	8.0	ug.mL-1	PMID[551403]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	8.0	ug.mL-1	PMID[551403]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	16.0	ug.mL-1	PMID[551403]
NPT925	Organism	Emericella nidulans	Emericella nidulans	MIC	=	16.0	ug.mL-1	PMID[551403]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	32.0	ug.mL-1	PMID[551403]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	64.0	ug.mL-1	PMID[551403]

☑ 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 NPC166480 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	368
0.1-0.2	1595
0.2-0.3	3598
0.3-0.4	10160
0.4-0.5	8905
0.5-0.6	4596
0.6-0.7	6360
0.7-0.8	5392
0.8-0.85	1278
0.85-0.9	322
0.9-0.95	112
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC282780
0.9621	High Similarity	NPC242994
0.9621	High Similarity	NPC138099
0.9606	High Similarity	NPC92624
0.9549	High Similarity	NPC169452
0.9549	High Similarity	NPC181560
0.9531	High Similarity	NPC259942
0.947	High Similarity	NPC471905
0.947	High Similarity	NPC53206
0.947	High Similarity	NPC53414
0.9453	High Similarity	NPC474998
0.9449	High Similarity	NPC23126
0.9449	High Similarity	NPC72158
0.9449	High Similarity	NPC30501
0.9449	High Similarity	NPC266689
0.9449	High Similarity	NPC103356
0.9449	High Similarity	NPC100067
0.9449	High Similarity	NPC169250
0.9449	High Similarity	NPC105157
0.9449	High Similarity	NPC162612
0.9449	High Similarity	NPC190043
0.9449	High Similarity	NPC98254
0.9407	High Similarity	NPC193555
0.9394	High Similarity	NPC254847
0.9394	High Similarity	NPC191976
0.9394	High Similarity	NPC118919
0.9389	High Similarity	NPC44437
0.9375	High Similarity	NPC221777
0.9375	High Similarity	NPC473017
0.9375	High Similarity	NPC21305
0.937	High Similarity	NPC62952
0.937	High Similarity	NPC8745
0.937	High Similarity	NPC267846
0.9323	High Similarity	NPC290030
0.9313	High Similarity	NPC267205
0.9297	High Similarity	NPC116513
0.9291	High Similarity	NPC10926
0.9291	High Similarity	NPC477454
0.9265	High Similarity	NPC135524
0.9248	High Similarity	NPC65005
0.9248	High Similarity	NPC264112
0.9248	High Similarity	NPC194764
0.9237	High Similarity	NPC175738
0.9219	High Similarity	NPC473691
0.9213	High Similarity	NPC13238
0.9191	High Similarity	NPC305845
0.9191	High Similarity	NPC204045
0.9191	High Similarity	NPC246638
0.9185	High Similarity	NPC143438
0.9185	High Similarity	NPC472903
0.9167	High Similarity	NPC213485
0.9167	High Similarity	NPC40524
0.9167	High Similarity	NPC139074
0.916	High Similarity	NPC475042
0.9154	High Similarity	NPC109123
0.913	High Similarity	NPC193703
0.913	High Similarity	NPC21599
0.9124	High Similarity	NPC474961
0.9124	High Similarity	NPC49108
0.9084	High Similarity	NPC17840
0.9084	High Similarity	NPC247477
0.9065	High Similarity	NPC34482
0.9058	High Similarity	NPC474203
0.9058	High Similarity	NPC313047
0.9058	High Similarity	NPC451542
0.9058	High Similarity	NPC295712
0.9055	High Similarity	NPC133909
0.9055	High Similarity	NPC309765
0.9055	High Similarity	NPC91105
0.9055	High Similarity	NPC32032
0.9051	High Similarity	NPC472904
0.9051	High Similarity	NPC187843
0.9044	High Similarity	NPC162939
0.9044	High Similarity	NPC190457
0.9037	High Similarity	NPC53001
0.903	High Similarity	NPC61153
0.903	High Similarity	NPC70859
0.903	High Similarity	NPC130899
0.903	High Similarity	NPC290803
0.903	High Similarity	NPC161632
0.903	High Similarity	NPC283590
0.9023	High Similarity	NPC180261
0.9023	High Similarity	NPC37299
0.9008	High Similarity	NPC99731
0.9008	High Similarity	NPC476119
0.9	High Similarity	NPC470570
0.8993	High Similarity	NPC244691
0.8993	High Similarity	NPC48762
0.8993	High Similarity	NPC471906
0.8992	High Similarity	NPC475733
0.8986	High Similarity	NPC137649
0.8986	High Similarity	NPC73061
0.8984	High Similarity	NPC472029
0.8984	High Similarity	NPC65761
0.8978	High Similarity	NPC203063
0.8978	High Similarity	NPC472366
0.8976	High Similarity	NPC242895
0.8976	High Similarity	NPC196976
0.8976	High Similarity	NPC156139
0.8976	High Similarity	NPC224273
0.8976	High Similarity	NPC73532
0.8976	High Similarity	NPC45438
0.8976	High Similarity	NPC267552
0.8976	High Similarity	NPC215392
0.8976	High Similarity	NPC303737
0.8976	High Similarity	NPC115159
0.8976	High Similarity	NPC19174
0.8976	High Similarity	NPC143427
0.8971	High Similarity	NPC87723
0.8955	High Similarity	NPC475088
0.8955	High Similarity	NPC12070
0.8947	High Similarity	NPC135801
0.8944	High Similarity	NPC10027
0.8944	High Similarity	NPC65775
0.8939	High Similarity	NPC147757
0.8936	High Similarity	NPC37709
0.8931	High Similarity	NPC179898
0.8923	High Similarity	NPC160499
0.8921	High Similarity	NPC174905
0.8921	High Similarity	NPC293545
0.8913	High Similarity	NPC290550
0.8898	High Similarity	NPC248363
0.8898	High Similarity	NPC149246
0.8898	High Similarity	NPC297186
0.8897	High Similarity	NPC474110
0.8897	High Similarity	NPC44960
0.8889	High Similarity	NPC470210
0.8889	High Similarity	NPC249272
0.8889	High Similarity	NPC283088
0.8881	High Similarity	NPC114183
0.8881	High Similarity	NPC48036
0.8872	High Similarity	NPC34070
0.8872	High Similarity	NPC469526
0.8872	High Similarity	NPC275504
0.8865	High Similarity	NPC271944
0.8865	High Similarity	NPC110882
0.8865	High Similarity	NPC85393
0.8857	High Similarity	NPC10764
0.8857	High Similarity	NPC227841
0.8846	High Similarity	NPC262671
0.8846	High Similarity	NPC201728
0.8841	High Similarity	NPC477956
0.8832	High Similarity	NPC4214
0.8832	High Similarity	NPC472419
0.8832	High Similarity	NPC13715
0.8824	High Similarity	NPC131039
0.8819	High Similarity	NPC159525
0.8815	High Similarity	NPC50924
0.8815	High Similarity	NPC270899
0.8815	High Similarity	NPC474519
0.8806	High Similarity	NPC478190
0.8803	High Similarity	NPC118027
0.8803	High Similarity	NPC245584
0.8803	High Similarity	NPC126767
0.8803	High Similarity	NPC56433
0.8803	High Similarity	NPC190648
0.8803	High Similarity	NPC312929
0.8803	High Similarity	NPC289042
0.8797	High Similarity	NPC62219
0.8797	High Similarity	NPC26697
0.8797	High Similarity	NPC244441
0.8797	High Similarity	NPC233056
0.8794	High Similarity	NPC12402
0.8788	High Similarity	NPC48248
0.8788	High Similarity	NPC24869
0.8788	High Similarity	NPC95537
0.8788	High Similarity	NPC41263
0.8788	High Similarity	NPC282923
0.8786	High Similarity	NPC238629
0.8786	High Similarity	NPC84266
0.8786	High Similarity	NPC296752
0.8777	High Similarity	NPC11056
0.8777	High Similarity	NPC110810
0.8768	High Similarity	NPC472368
0.8768	High Similarity	NPC21350
0.8759	High Similarity	NPC12165
0.8759	High Similarity	NPC186838
0.8759	High Similarity	NPC1486
0.8759	High Similarity	NPC472364
0.8759	High Similarity	NPC476333
0.8759	High Similarity	NPC66349
0.8759	High Similarity	NPC98115
0.8759	High Similarity	NPC477244
0.8759	High Similarity	NPC150399
0.8759	High Similarity	NPC477242
0.8759	High Similarity	NPC477243
0.8759	High Similarity	NPC41461
0.8759	High Similarity	NPC25287
0.8759	High Similarity	NPC472367
0.8759	High Similarity	NPC213603
0.8759	High Similarity	NPC168105
0.8759	High Similarity	NPC473391
0.8759	High Similarity	NPC249606
0.8759	High Similarity	NPC194579
0.8759	High Similarity	NPC274109
0.875	High Similarity	NPC255641
0.875	High Similarity	NPC227122
0.875	High Similarity	NPC146642
0.875	High Similarity	NPC290954
0.875	High Similarity	NPC229649

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 NPC166480 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	971
0.2-0.3	1424
0.3-0.4	2711
0.4-0.5	2078
0.5-0.6	1123
0.6-0.7	381
0.7-0.8	118
0.8-0.85	10
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9394	High Similarity	NPD1509	Clinical (unspecified phase)
0.8947	High Similarity	NPD943	Approved
0.8857	High Similarity	NPD7390	Discontinued
0.8702	High Similarity	NPD1470	Approved
0.8551	High Similarity	NPD651	Clinical (unspecified phase)
0.8538	High Similarity	NPD1201	Approved
0.8489	Intermediate Similarity	NPD5406	Approved
0.8489	Intermediate Similarity	NPD5404	Approved
0.8489	Intermediate Similarity	NPD5405	Approved
0.8489	Intermediate Similarity	NPD5408	Approved
0.8394	Intermediate Similarity	NPD1240	Approved
0.8322	Intermediate Similarity	NPD7819	Suspended
0.8286	Intermediate Similarity	NPD1510	Phase 2
0.8276	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD1607	Approved
0.8217	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD1164	Approved
0.8112	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD2935	Discontinued
0.8079	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6232	Discontinued
0.8027	Intermediate Similarity	NPD2532	Approved
0.8027	Intermediate Similarity	NPD2534	Approved
0.8027	Intermediate Similarity	NPD2533	Approved
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD4380	Phase 2
0.7986	Intermediate Similarity	NPD1549	Phase 2
0.7917	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6959	Discontinued
0.7877	Intermediate Similarity	NPD3750	Approved
0.7857	Intermediate Similarity	NPD3882	Suspended
0.7847	Intermediate Similarity	NPD2796	Approved
0.7843	Intermediate Similarity	NPD2801	Approved
0.7838	Intermediate Similarity	NPD1511	Approved
0.7829	Intermediate Similarity	NPD7411	Suspended
0.7808	Intermediate Similarity	NPD2800	Approved
0.7806	Intermediate Similarity	NPD3749	Approved
0.7806	Intermediate Similarity	NPD7075	Discontinued
0.7785	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD2799	Discontinued
0.7733	Intermediate Similarity	NPD1512	Approved
0.7727	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3226	Approved
0.7671	Intermediate Similarity	NPD2344	Approved
0.7671	Intermediate Similarity	NPD2346	Discontinued
0.7664	Intermediate Similarity	NPD9269	Phase 2
0.7639	Intermediate Similarity	NPD6651	Approved
0.763	Intermediate Similarity	NPD9268	Approved
0.7628	Intermediate Similarity	NPD7768	Phase 2
0.7625	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3764	Approved
0.76	Intermediate Similarity	NPD6799	Approved
0.7595	Intermediate Similarity	NPD5494	Approved
0.7574	Intermediate Similarity	NPD3019	Approved
0.7574	Intermediate Similarity	NPD2932	Approved
0.7548	Intermediate Similarity	NPD6801	Discontinued
0.7534	Intermediate Similarity	NPD3748	Approved
0.7533	Intermediate Similarity	NPD3300	Phase 2
0.7532	Intermediate Similarity	NPD6599	Discontinued
0.7517	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6020	Phase 2
0.7468	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2309	Approved
0.7462	Intermediate Similarity	NPD74	Approved
0.7462	Intermediate Similarity	NPD9266	Approved
0.745	Intermediate Similarity	NPD1243	Approved
0.745	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD230	Phase 1
0.7447	Intermediate Similarity	NPD2798	Approved
0.7423	Intermediate Similarity	NPD3818	Discontinued
0.7415	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD9493	Approved
0.7407	Intermediate Similarity	NPD6166	Phase 2
0.7407	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4750	Phase 3
0.7402	Intermediate Similarity	NPD846	Approved
0.7402	Intermediate Similarity	NPD940	Approved
0.7394	Intermediate Similarity	NPD5953	Discontinued
0.7391	Intermediate Similarity	NPD5711	Approved
0.7391	Intermediate Similarity	NPD5710	Approved
0.7385	Intermediate Similarity	NPD9264	Approved
0.7385	Intermediate Similarity	NPD9267	Approved
0.7385	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD9263	Approved
0.7378	Intermediate Similarity	NPD5844	Phase 1
0.7365	Intermediate Similarity	NPD1551	Phase 2
0.7365	Intermediate Similarity	NPD6100	Approved
0.7365	Intermediate Similarity	NPD6099	Approved
0.7361	Intermediate Similarity	NPD2313	Discontinued
0.7342	Intermediate Similarity	NPD3817	Phase 2
0.7338	Intermediate Similarity	NPD920	Approved
0.7323	Intermediate Similarity	NPD1242	Phase 1
0.7296	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1465	Phase 2
0.7273	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7286	Phase 2
0.7254	Intermediate Similarity	NPD1203	Approved
0.7246	Intermediate Similarity	NPD6559	Discontinued
0.7241	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3926	Phase 2
0.7229	Intermediate Similarity	NPD7074	Phase 3
0.7208	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1471	Phase 3
0.719	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD9545	Approved
0.7172	Intermediate Similarity	NPD4625	Phase 3
0.7171	Intermediate Similarity	NPD7003	Approved
0.7171	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7054	Approved
0.7168	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD3023	Approved
0.7143	Intermediate Similarity	NPD3026	Approved
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7132	Intermediate Similarity	NPD5951	Approved
0.7132	Intermediate Similarity	NPD9281	Approved
0.7126	Intermediate Similarity	NPD7472	Approved
0.7125	Intermediate Similarity	NPD5402	Approved
0.7122	Intermediate Similarity	NPD3025	Approved
0.7122	Intermediate Similarity	NPD1651	Approved
0.7122	Intermediate Similarity	NPD3024	Approved
0.7117	Intermediate Similarity	NPD1247	Approved
0.7115	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7635	Approved
0.7109	Intermediate Similarity	NPD3020	Approved
0.7099	Intermediate Similarity	NPD919	Approved
0.7083	Intermediate Similarity	NPD6797	Phase 2
0.7077	Intermediate Similarity	NPD9261	Approved
0.7063	Intermediate Similarity	NPD1283	Approved
0.7063	Intermediate Similarity	NPD1876	Approved
0.7059	Intermediate Similarity	NPD4628	Phase 3
0.7042	Intermediate Similarity	NPD9717	Approved
0.7041	Intermediate Similarity	NPD7251	Discontinued
0.7025	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7458	Discontinued
0.7015	Intermediate Similarity	NPD3021	Approved
0.7015	Intermediate Similarity	NPD3022	Approved
0.7008	Intermediate Similarity	NPD2860	Approved
0.7008	Intermediate Similarity	NPD2859	Approved
0.7007	Intermediate Similarity	NPD3268	Approved
0.7007	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD7808	Phase 3
0.7	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2654	Approved
0.6992	Remote Similarity	NPD2342	Discontinued
0.6989	Remote Similarity	NPD6535	Approved
0.6989	Remote Similarity	NPD6534	Approved
0.6986	Remote Similarity	NPD6832	Phase 2
0.698	Remote Similarity	NPD447	Suspended
0.697	Remote Similarity	NPD7229	Phase 3
0.6954	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4626	Approved
0.6948	Remote Similarity	NPD3400	Discontinued
0.6947	Remote Similarity	NPD1929	Approved
0.6947	Remote Similarity	NPD1930	Approved
0.6947	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2934	Approved
0.6929	Remote Similarity	NPD2933	Approved
0.6923	Remote Similarity	NPD1608	Approved
0.6914	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2296	Approved
0.6914	Remote Similarity	NPD4288	Approved
0.6903	Remote Similarity	NPD6190	Approved
0.6897	Remote Similarity	NPD2797	Approved
0.6894	Remote Similarity	NPD37	Approved
0.6892	Remote Similarity	NPD411	Approved
0.6889	Remote Similarity	NPD6777	Approved
0.6889	Remote Similarity	NPD6780	Approved
0.6889	Remote Similarity	NPD6776	Approved
0.6889	Remote Similarity	NPD6781	Approved
0.6889	Remote Similarity	NPD6778	Approved
0.6889	Remote Similarity	NPD6779	Approved
0.6889	Remote Similarity	NPD6782	Approved
0.6882	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5401	Approved
0.6875	Remote Similarity	NPD1755	Approved
0.6872	Remote Similarity	NPD7699	Phase 2
0.6872	Remote Similarity	NPD7700	Phase 2
0.6871	Remote Similarity	NPD4908	Phase 1
0.6867	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8312	Approved
0.686	Remote Similarity	NPD8313	Approved
0.6857	Remote Similarity	NPD4287	Approved
0.6853	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1281	Approved
0.6846	Remote Similarity	NPD6663	Approved
0.6842	Remote Similarity	NPD4308	Phase 3
0.6839	Remote Similarity	NPD8166	Discontinued
0.6831	Remote Similarity	NPD7163	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