NPASS Compound

Structure

NPC475008 OpenBabel07101718232D 27 28 0 0 0 0 0 0 0 0999 V2000 -1.7321 1.0000 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 4.3301 1.5000 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 5.1962 1.0000 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 6.0622 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 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 -0.8660 -1.5000 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 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 2.5000 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 -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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 3.0000 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 -1.7321 0.0000 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 26 1 0 0 0 0 2 27 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 19 2 0 0 0 0 17 19 1 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 20 25 2 0 0 0 0 21 23 2 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.21
Volume:	405.957
LogP:	5.242
LogD:	4.223
LogS:	-5.378
# Rotatable Bonds:	12
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.392
Synthetic Accessibility Score:	2.016
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	1.4148427908367012e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.756

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148
Plasma Protein Binding (PPB):	97.37120056152344%
Volume Distribution (VD):	0.792
Pgp-substrate:	0.4896852970123291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.929
CYP2C19-substrate:	0.166
CYP2C9-inhibitor:	0.874
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.762
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.844
CYP3A4-substrate:	0.389

ADMET: Excretion

Clearance (CL):	8.927
Half-life (T1/2):	0.398

ADMET: Toxicity

hERG Blockers:	0.448
Human Hepatotoxicity (H-HT):	0.036
Drug-inuced Liver Injury (DILI):	0.755
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.935
Carcinogencity:	0.122
Eye Corrosion:	0.005
Eye Irritation:	0.941
Respiratory Toxicity:	0.726

Download Data

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

Natural Product: NPC475008

Natural Product ID:	NPC475008
*Common Name:**	1-(2,6-Dimethoxyphenyl)-9-(4-Hydroxyphenyl)Nonan-1-One
IUPAC Name:	1-(2,6-dimethoxyphenyl)-9-(4-hydroxyphenyl)nonan-1-one
Synonyms:
Standard InCHIKey:	WUIAFOCKBCEKLG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H30O4/c1-26-21-12-9-13-22(27-2)23(21)20(25)11-8-6-4-3-5-7-10-18-14-16-19(24)17-15-18/h9,12-17,24H,3-8,10-11H2,1-2H3
SMILES:	COc1cccc(c1C(=O)CCCCCCCCc1ccc(cc1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491790
PubChem CID:	44576023
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5241	Myristica fragrans	Species	Myristicaceae	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	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[572475]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	<	32.0	ug.mL-1	PMID[572475]
NPT3730	Organism	Enterococcus durans	Enterococcus durans	MIC	<	32.0	ug.mL-1	PMID[572475]
NPT20	Organism	Candida albicans	Candida albicans	MIC	<	32.0	ug.mL-1	PMID[572475]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	32.0	ug.mL-1	PMID[572475]

☑ 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 NPC475008 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	327
0.1-0.2	1484
0.2-0.3	3920
0.3-0.4	11033
0.4-0.5	7226
0.5-0.6	3751
0.6-0.7	5957
0.7-0.8	6180
0.8-0.85	1732
0.85-0.9	738
0.9-0.95	291
0.95-1	58

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC186097
1.0	High Similarity	NPC475009
0.9843	High Similarity	NPC20560
0.9843	High Similarity	NPC18877
0.9843	High Similarity	NPC159623
0.9843	High Similarity	NPC82225
0.9843	High Similarity	NPC144051
0.9843	High Similarity	NPC28753
0.9843	High Similarity	NPC294593
0.9843	High Similarity	NPC204960
0.9766	High Similarity	NPC286336
0.969	High Similarity	NPC13575
0.9688	High Similarity	NPC337373
0.9688	High Similarity	NPC242294
0.9688	High Similarity	NPC56031
0.9688	High Similarity	NPC188646
0.9688	High Similarity	NPC139813
0.9688	High Similarity	NPC192304
0.9688	High Similarity	NPC312318
0.9688	High Similarity	NPC263670
0.9688	High Similarity	NPC472365
0.9688	High Similarity	NPC175098
0.9615	High Similarity	NPC98115
0.9615	High Similarity	NPC1486
0.9615	High Similarity	NPC186838
0.9615	High Similarity	NPC41461
0.9615	High Similarity	NPC25287
0.9615	High Similarity	NPC477244
0.9615	High Similarity	NPC477242
0.9615	High Similarity	NPC168105
0.9615	High Similarity	NPC150399
0.9615	High Similarity	NPC12165
0.9615	High Similarity	NPC477243
0.9615	High Similarity	NPC274109
0.9615	High Similarity	NPC66349
0.9615	High Similarity	NPC249606
0.9612	High Similarity	NPC103842
0.9609	High Similarity	NPC129132
0.9609	High Similarity	NPC257756
0.9609	High Similarity	NPC87231
0.9609	High Similarity	NPC212631
0.9609	High Similarity	NPC205468
0.9542	High Similarity	NPC317119
0.9542	High Similarity	NPC153979
0.9542	High Similarity	NPC472419
0.9538	High Similarity	NPC156092
0.9538	High Similarity	NPC131039
0.9531	High Similarity	NPC313618
0.9531	High Similarity	NPC64359
0.9531	High Similarity	NPC112192
0.9531	High Similarity	NPC66384
0.9531	High Similarity	NPC189106
0.9531	High Similarity	NPC164236
0.9531	High Similarity	NPC308037
0.9531	High Similarity	NPC309717
0.9531	High Similarity	NPC262359
0.9531	High Similarity	NPC128348
0.9524	High Similarity	NPC475017
0.947	High Similarity	NPC251681
0.947	High Similarity	NPC21350
0.947	High Similarity	NPC243528
0.947	High Similarity	NPC124269
0.947	High Similarity	NPC472368
0.9466	High Similarity	NPC213603
0.9466	High Similarity	NPC476333
0.9466	High Similarity	NPC473391
0.9466	High Similarity	NPC472367
0.9466	High Similarity	NPC472364
0.9398	High Similarity	NPC470211
0.9398	High Similarity	NPC472366
0.9398	High Similarity	NPC477956
0.9394	High Similarity	NPC303644
0.9394	High Similarity	NPC116632
0.9394	High Similarity	NPC181124
0.9394	High Similarity	NPC209560
0.9394	High Similarity	NPC294409
0.9394	High Similarity	NPC188879
0.9394	High Similarity	NPC162680
0.9394	High Similarity	NPC7013
0.9385	High Similarity	NPC27643
0.9375	High Similarity	NPC247779
0.9328	High Similarity	NPC188243
0.9328	High Similarity	NPC159275
0.9328	High Similarity	NPC265178
0.9328	High Similarity	NPC204985
0.9328	High Similarity	NPC11056
0.9328	High Similarity	NPC213659
0.9328	High Similarity	NPC76445
0.9328	High Similarity	NPC284550
0.9328	High Similarity	NPC215311
0.9328	High Similarity	NPC241100
0.9328	High Similarity	NPC6407
0.9328	High Similarity	NPC48624
0.9328	High Similarity	NPC172250
0.9328	High Similarity	NPC129853
0.9328	High Similarity	NPC110228
0.9328	High Similarity	NPC259166
0.9328	High Similarity	NPC144118
0.9328	High Similarity	NPC326109
0.9328	High Similarity	NPC80962
0.9328	High Similarity	NPC219917
0.9323	High Similarity	NPC12175
0.9323	High Similarity	NPC471620
0.9323	High Similarity	NPC55162
0.9323	High Similarity	NPC309154
0.9323	High Similarity	NPC278323
0.9323	High Similarity	NPC279668
0.9323	High Similarity	NPC90665
0.9318	High Similarity	NPC127447
0.9318	High Similarity	NPC473887
0.9318	High Similarity	NPC13408
0.9318	High Similarity	NPC231772
0.9318	High Similarity	NPC234133
0.9318	High Similarity	NPC194281
0.9318	High Similarity	NPC29353
0.9318	High Similarity	NPC124784
0.9318	High Similarity	NPC47815
0.9318	High Similarity	NPC240593
0.9308	High Similarity	NPC215875
0.9308	High Similarity	NPC15834
0.9297	High Similarity	NPC211120
0.9297	High Similarity	NPC212379
0.9297	High Similarity	NPC69235
0.9291	High Similarity	NPC128428
0.9291	High Similarity	NPC305518
0.9259	High Similarity	NPC282300
0.9259	High Similarity	NPC26238
0.9259	High Similarity	NPC55832
0.9259	High Similarity	NPC268204
0.9259	High Similarity	NPC470087
0.9259	High Similarity	NPC126534
0.9259	High Similarity	NPC49108
0.9259	High Similarity	NPC110969
0.9259	High Similarity	NPC40118
0.9259	High Similarity	NPC469404
0.9259	High Similarity	NPC26051
0.9259	High Similarity	NPC321980
0.9259	High Similarity	NPC52789
0.9259	High Similarity	NPC232021
0.9259	High Similarity	NPC470089
0.9254	High Similarity	NPC53181
0.9254	High Similarity	NPC217186
0.9254	High Similarity	NPC20709
0.9254	High Similarity	NPC96565
0.9254	High Similarity	NPC140890
0.9254	High Similarity	NPC216978
0.9254	High Similarity	NPC283429
0.9254	High Similarity	NPC109232
0.9254	High Similarity	NPC329203
0.9254	High Similarity	NPC55018
0.9254	High Similarity	NPC78913
0.9254	High Similarity	NPC310135
0.9254	High Similarity	NPC150648
0.9254	High Similarity	NPC265871
0.9254	High Similarity	NPC18260
0.9254	High Similarity	NPC225153
0.9254	High Similarity	NPC274784
0.9254	High Similarity	NPC301217
0.9254	High Similarity	NPC295384
0.9254	High Similarity	NPC220062
0.9254	High Similarity	NPC303633
0.9254	High Similarity	NPC222342
0.9248	High Similarity	NPC250266
0.9248	High Similarity	NPC266597
0.9242	High Similarity	NPC234560
0.9242	High Similarity	NPC39426
0.9237	High Similarity	NPC16197
0.9231	High Similarity	NPC113006
0.9225	High Similarity	NPC84772
0.9219	High Similarity	NPC80694
0.9219	High Similarity	NPC186098
0.9191	High Similarity	NPC324134
0.9191	High Similarity	NPC40833
0.9191	High Similarity	NPC125855
0.9191	High Similarity	NPC182852
0.9191	High Similarity	NPC76372
0.9191	High Similarity	NPC107572
0.9191	High Similarity	NPC161506
0.9191	High Similarity	NPC226636
0.9191	High Similarity	NPC37496
0.9191	High Similarity	NPC78
0.9191	High Similarity	NPC166934
0.9191	High Similarity	NPC166482
0.9191	High Similarity	NPC194432
0.9191	High Similarity	NPC148757
0.9191	High Similarity	NPC11561
0.9191	High Similarity	NPC1089
0.9191	High Similarity	NPC167624
0.9191	High Similarity	NPC228504
0.9191	High Similarity	NPC76338
0.9191	High Similarity	NPC32739
0.9191	High Similarity	NPC227579
0.9191	High Similarity	NPC265040
0.9191	High Similarity	NPC64915
0.9191	High Similarity	NPC223500
0.9191	High Similarity	NPC328164
0.9191	High Similarity	NPC10937
0.9191	High Similarity	NPC220998
0.9191	High Similarity	NPC66515
0.9191	High Similarity	NPC296917

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 NPC475008 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	943
0.2-0.3	1404
0.3-0.4	2585
0.4-0.5	1961
0.5-0.6	1264
0.6-0.7	494
0.7-0.8	159
0.8-0.85	35
0.85-0.9	5
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9531	High Similarity	NPD1240	Approved
0.9385	High Similarity	NPD1607	Approved
0.9242	High Similarity	NPD1510	Phase 2
0.9104	High Similarity	NPD1552	Clinical (unspecified phase)
0.9104	High Similarity	NPD1550	Clinical (unspecified phase)
0.9058	High Similarity	NPD4378	Clinical (unspecified phase)
0.9037	High Similarity	NPD1549	Phase 2
0.8786	High Similarity	NPD7410	Clinical (unspecified phase)
0.875	High Similarity	NPD2796	Approved
0.8613	High Similarity	NPD2935	Discontinued
0.8611	High Similarity	NPD4380	Phase 2
0.8582	High Similarity	NPD6799	Approved
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8552	High Similarity	NPD7411	Suspended
0.8529	High Similarity	NPD6651	Approved
0.8503	High Similarity	NPD8443	Clinical (unspecified phase)
0.85	High Similarity	NPD3750	Approved
0.85	High Similarity	NPD1878	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1934	Approved
0.8489	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD1551	Phase 2
0.8451	Intermediate Similarity	NPD1511	Approved
0.8435	Intermediate Similarity	NPD2801	Approved
0.8389	Intermediate Similarity	NPD7075	Discontinued
0.837	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD6599	Discontinued
0.8333	Intermediate Similarity	NPD1512	Approved
0.8322	Intermediate Similarity	NPD7768	Phase 2
0.8322	Intermediate Similarity	NPD3882	Suspended
0.8311	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD7819	Suspended
0.8271	Intermediate Similarity	NPD1203	Approved
0.8267	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD6801	Discontinued
0.8209	Intermediate Similarity	NPD2798	Approved
0.8169	Intermediate Similarity	NPD2800	Approved
0.8169	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD5403	Approved
0.8143	Intermediate Similarity	NPD3748	Approved
0.8143	Intermediate Similarity	NPD2799	Discontinued
0.8116	Intermediate Similarity	NPD943	Approved
0.8088	Intermediate Similarity	NPD6832	Phase 2
0.8065	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6166	Phase 2
0.8065	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8062	Intermediate Similarity	NPD9493	Approved
0.8052	Intermediate Similarity	NPD6232	Discontinued
0.8045	Intermediate Similarity	NPD9717	Approved
0.8042	Intermediate Similarity	NPD2654	Approved
0.8028	Intermediate Similarity	NPD2344	Approved
0.8026	Intermediate Similarity	NPD3749	Approved
0.8014	Intermediate Similarity	NPD2532	Approved
0.8014	Intermediate Similarity	NPD5401	Approved
0.8014	Intermediate Similarity	NPD2533	Approved
0.8014	Intermediate Similarity	NPD2534	Approved
0.8013	Intermediate Similarity	NPD3817	Phase 2
0.8013	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD6959	Discontinued
0.797	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD422	Phase 1
0.7956	Intermediate Similarity	NPD4908	Phase 1
0.7939	Intermediate Similarity	NPD1548	Phase 1
0.7917	Intermediate Similarity	NPD1243	Approved
0.7911	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD3972	Approved
0.7887	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD2797	Approved
0.7862	Intermediate Similarity	NPD7074	Phase 3
0.7848	Intermediate Similarity	NPD3818	Discontinued
0.7842	Intermediate Similarity	NPD3268	Approved
0.7842	Intermediate Similarity	NPD2313	Discontinued
0.7842	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1610	Phase 2
0.7812	Intermediate Similarity	NPD5953	Discontinued
0.7808	Intermediate Similarity	NPD2309	Approved
0.7799	Intermediate Similarity	NPD7286	Phase 2
0.7799	Intermediate Similarity	NPD7054	Approved
0.7785	Intermediate Similarity	NPD920	Approved
0.7778	Intermediate Similarity	NPD5402	Approved
0.7764	Intermediate Similarity	NPD6559	Discontinued
0.7755	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7472	Approved
0.774	Intermediate Similarity	NPD4628	Phase 3
0.7727	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6100	Approved
0.7708	Intermediate Similarity	NPD6099	Approved
0.7704	Intermediate Similarity	NPD1201	Approved
0.7703	Intermediate Similarity	NPD7390	Discontinued
0.7702	Intermediate Similarity	NPD6797	Phase 2
0.7692	Intermediate Similarity	NPD5494	Approved
0.7669	Intermediate Similarity	NPD9545	Approved
0.7667	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1876	Approved
0.7654	Intermediate Similarity	NPD7251	Discontinued
0.7651	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3027	Phase 3
0.7639	Intermediate Similarity	NPD7033	Discontinued
0.7639	Intermediate Similarity	NPD4308	Phase 3
0.7619	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1164	Approved
0.7609	Intermediate Similarity	NPD1470	Approved
0.7607	Intermediate Similarity	NPD7808	Phase 3
0.7589	Intermediate Similarity	NPD3764	Approved
0.7589	Intermediate Similarity	NPD1296	Phase 2
0.7566	Intermediate Similarity	NPD3226	Approved
0.7557	Intermediate Similarity	NPD1241	Discontinued
0.7552	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1933	Approved
0.7547	Intermediate Similarity	NPD3926	Phase 2
0.7536	Intermediate Similarity	NPD3225	Approved
0.7534	Intermediate Similarity	NPD2346	Discontinued
0.752	Intermediate Similarity	NPD846	Approved
0.752	Intermediate Similarity	NPD940	Approved
0.75	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3847	Discontinued
0.7482	Intermediate Similarity	NPD3266	Approved
0.7482	Intermediate Similarity	NPD3267	Approved
0.7468	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD5405	Approved
0.7466	Intermediate Similarity	NPD5406	Approved
0.7466	Intermediate Similarity	NPD5404	Approved
0.7466	Intermediate Similarity	NPD5408	Approved
0.7465	Intermediate Similarity	NPD411	Approved
0.7465	Intermediate Similarity	NPD6798	Discontinued
0.7464	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD74	Approved
0.7442	Intermediate Similarity	NPD9266	Approved
0.7436	Intermediate Similarity	NPD4288	Approved
0.7431	Intermediate Similarity	NPD5124	Phase 1
0.7431	Intermediate Similarity	NPD230	Phase 1
0.7431	Intermediate Similarity	NPD447	Suspended
0.7431	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1019	Discontinued
0.7405	Intermediate Similarity	NPD919	Approved
0.7397	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4625	Phase 3
0.7391	Intermediate Similarity	NPD1481	Phase 2
0.7391	Intermediate Similarity	NPD1608	Approved
0.7376	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5710	Approved
0.7375	Intermediate Similarity	NPD5711	Approved
0.7364	Intermediate Similarity	NPD9264	Approved
0.7364	Intermediate Similarity	NPD9267	Approved
0.7364	Intermediate Similarity	NPD9263	Approved
0.7362	Intermediate Similarity	NPD5844	Phase 1
0.7361	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4307	Phase 2
0.7361	Intermediate Similarity	NPD1613	Approved
0.7353	Intermediate Similarity	NPD1651	Approved
0.7351	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4749	Approved
0.7338	Intermediate Similarity	NPD7458	Discontinued
0.7319	Intermediate Similarity	NPD1535	Discovery
0.7317	Intermediate Similarity	NPD1729	Discontinued
0.7312	Intermediate Similarity	NPD1247	Approved
0.731	Intermediate Similarity	NPD6355	Discontinued
0.7303	Intermediate Similarity	NPD4662	Approved
0.7303	Intermediate Similarity	NPD4661	Approved
0.7286	Intermediate Similarity	NPD1283	Approved
0.7279	Intermediate Similarity	NPD1894	Discontinued
0.7273	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4360	Phase 2
0.7267	Intermediate Similarity	NPD4363	Phase 3
0.7261	Intermediate Similarity	NPD1465	Phase 2
0.7259	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3018	Phase 2
0.7229	Intermediate Similarity	NPD6104	Discontinued
0.7226	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4361	Phase 2
0.7225	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2296	Approved
0.7214	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5536	Phase 2
0.7203	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD37	Approved
0.719	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4626	Approved
0.7174	Intermediate Similarity	NPD17	Approved
0.7172	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD5049	Phase 3
0.7133	Intermediate Similarity	NPD2861	Phase 2
0.7133	Intermediate Similarity	NPD9494	Approved
0.7125	Intermediate Similarity	NPD6971	Discontinued
0.7124	Intermediate Similarity	NPD4357	Discontinued
0.7124	Intermediate Similarity	NPD7212	Phase 2
0.7124	Intermediate Similarity	NPD7213	Phase 3
0.712	Intermediate Similarity	NPD2859	Approved
0.712	Intermediate Similarity	NPD2860	Approved
0.7115	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4477	Approved
0.7114	Intermediate Similarity	NPD4476	Approved
0.7111	Intermediate Similarity	NPD9281	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