NPASS Compound

Structure

CID124269 OpenBabel06191715482D 27 28 0 0 0 0 0 0 0 0999 V2000 -7.7942 -1.5000 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 -3.4641 -3.0000 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 2.5981 -1.5000 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 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -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 0.0000 -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 0.8660 -1.5000 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 0.8660 1.5000 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 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 17 2 0 0 0 0 13 27 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 18 23 1 0 0 0 0 19 27 1 0 0 0 0 20 22 2 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 0 0 0 0 22 23 1 0 0 0 0 23 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.18
Volume:	400.684
LogP:	6.289
LogD:	4.624
LogS:	-4.17
# Rotatable Bonds:	8
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.485
Synthetic Accessibility Score:	2.528
Fsp3:	0.261
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:	-4.909
MDCK Permeability:	1.8997690858668648e-05
Pgp-inhibitor:	0.844
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.759
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	101.93290710449219%
Volume Distribution (VD):	0.508
Pgp-substrate:	0.5998778343200684%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.909
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.925
CYP2D6-substrate:	0.384
CYP3A4-inhibitor:	0.616
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	8.772
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.521
Drug-inuced Liver Injury (DILI):	0.746
AMES Toxicity:	0.151
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.587
Skin Sensitization:	0.888
Carcinogencity:	0.096
Eye Corrosion:	0.003
Eye Irritation:	0.933
Respiratory Toxicity:	0.509

Download Data

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

Natural Product: NPC124269

Natural Product ID:	NPC124269
*Common Name:**	4-Geranyloxy-2,6-Dihydroxybenzophenone
IUPAC Name:	[4-[(2E)-3,7-dimethylocta-2,6-dienoxy]-2,6-dihydroxyphenyl]-phenylmethanone
Synonyms:
Standard InCHIKey:	CPWFSCYLMXLCDK-SFQUDFHCSA-N
Standard InCHI:	InChI=1S/C23H26O4/c1-16(2)8-7-9-17(3)12-13-27-19-14-20(24)22(21(25)15-19)23(26)18-10-5-4-6-11-18/h4-6,8,10-12,14-15,24-25H,7,9,13H2,1-3H3/b17-12+
SMILES:	C/C(=CCOc1cc(O)c(c(c1)O)C(=O)c1ccccc1)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510517
PubChem CID:	44575287
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
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	twig	n.a.	PMID[11908969]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	stem	n.a.	PMID[11908969]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11908969]
NPO22504	Tovomita longifolia	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16562847]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	roots	Daba desert reserve (50 km South of Amman), Jordan	2009-APR	PMID[21650157]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO18005	Artemisia leucodes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19359	Parmotrema delicatulum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13263	Verbena brasiliensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19501	Pseudosuberites hyalinus	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22504	Tovomita longifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11770	Amphicome emodi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14950	Ardisia polycephala	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6106	Hymeniacidon perlevis	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18995	Gaultheria itoana	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17438	Polygala virgata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19560	Populus italica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18657	Galanthus gracilis	Species	Amaryllidaceae	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
GI50	3
MIC	2

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	4.8	ug.mL-1	PMID[533376]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	4.4	ug.mL-1	PMID[533376]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	2.0	ug.mL-1	PMID[533376]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[533376]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	12.5	ug.mL-1	PMID[533376]

☑ 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 NPC124269 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	340
0.1-0.2	1463
0.2-0.3	3956
0.3-0.4	10120
0.4-0.5	8111
0.5-0.6	3565
0.6-0.7	5601
0.7-0.8	5379
0.8-0.85	2151
0.85-0.9	1266
0.9-0.95	542
0.95-1	203

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC188879
0.9848	High Similarity	NPC240593
0.9704	High Similarity	NPC110228
0.9704	High Similarity	NPC188243
0.9704	High Similarity	NPC76445
0.9704	High Similarity	NPC129853
0.9704	High Similarity	NPC284550
0.9704	High Similarity	NPC6407
0.9701	High Similarity	NPC188947
0.9701	High Similarity	NPC99333
0.9701	High Similarity	NPC280284
0.9697	High Similarity	NPC286336
0.9635	High Similarity	NPC149026
0.9635	High Similarity	NPC68104
0.9635	High Similarity	NPC91560
0.9635	High Similarity	NPC175504
0.9635	High Similarity	NPC257097
0.9635	High Similarity	NPC39329
0.9635	High Similarity	NPC221432
0.9635	High Similarity	NPC150408
0.9635	High Similarity	NPC169591
0.9635	High Similarity	NPC75049
0.9635	High Similarity	NPC143896
0.9635	High Similarity	NPC164980
0.9635	High Similarity	NPC310130
0.9632	High Similarity	NPC110969
0.9632	High Similarity	NPC3188
0.963	High Similarity	NPC265871
0.963	High Similarity	NPC225153
0.963	High Similarity	NPC261234
0.963	High Similarity	NPC20709
0.963	High Similarity	NPC222342
0.963	High Similarity	NPC150648
0.963	High Similarity	NPC274784
0.963	High Similarity	NPC140890
0.963	High Similarity	NPC329203
0.963	High Similarity	NPC310135
0.9627	High Similarity	NPC290291
0.9627	High Similarity	NPC275055
0.9627	High Similarity	NPC250266
0.9627	High Similarity	NPC266597
0.9621	High Similarity	NPC188646
0.9621	High Similarity	NPC204960
0.9621	High Similarity	NPC242294
0.9621	High Similarity	NPC139813
0.9621	High Similarity	NPC20560
0.9621	High Similarity	NPC294593
0.9621	High Similarity	NPC56031
0.9621	High Similarity	NPC192304
0.9621	High Similarity	NPC312318
0.9621	High Similarity	NPC159623
0.9621	High Similarity	NPC263670
0.9621	High Similarity	NPC144051
0.9621	High Similarity	NPC18877
0.9621	High Similarity	NPC28753
0.9621	High Similarity	NPC472365
0.9621	High Similarity	NPC337373
0.9621	High Similarity	NPC175098
0.9621	High Similarity	NPC82225
0.9565	High Similarity	NPC236766
0.9565	High Similarity	NPC473015
0.9565	High Similarity	NPC209040
0.9565	High Similarity	NPC197252
0.9565	High Similarity	NPC473013
0.9562	High Similarity	NPC148757
0.9562	High Similarity	NPC37496
0.9562	High Similarity	NPC226636
0.9562	High Similarity	NPC125855
0.9562	High Similarity	NPC296917
0.9562	High Similarity	NPC1089
0.9562	High Similarity	NPC194432
0.9562	High Similarity	NPC76338
0.9562	High Similarity	NPC306829
0.9562	High Similarity	NPC166934
0.9562	High Similarity	NPC182852
0.9562	High Similarity	NPC161506
0.9562	High Similarity	NPC228504
0.9562	High Similarity	NPC107572
0.9562	High Similarity	NPC227579
0.9562	High Similarity	NPC78
0.9562	High Similarity	NPC166482
0.9562	High Similarity	NPC223500
0.9562	High Similarity	NPC11561
0.9562	High Similarity	NPC177354
0.9562	High Similarity	NPC64915
0.9562	High Similarity	NPC265040
0.9562	High Similarity	NPC167624
0.9562	High Similarity	NPC324436
0.9562	High Similarity	NPC220998
0.9562	High Similarity	NPC66515
0.9562	High Similarity	NPC202981
0.9562	High Similarity	NPC324134
0.9562	High Similarity	NPC10937
0.9562	High Similarity	NPC328164
0.9562	High Similarity	NPC40833
0.9562	High Similarity	NPC76372
0.9562	High Similarity	NPC32739
0.9559	High Similarity	NPC159275
0.9559	High Similarity	NPC69769
0.9559	High Similarity	NPC261227
0.9559	High Similarity	NPC241100
0.9559	High Similarity	NPC270883
0.9559	High Similarity	NPC172986
0.9556	High Similarity	NPC472460
0.9556	High Similarity	NPC329225
0.9556	High Similarity	NPC118813
0.9556	High Similarity	NPC147686
0.9552	High Similarity	NPC98115
0.9552	High Similarity	NPC477243
0.9552	High Similarity	NPC473887
0.9552	High Similarity	NPC1486
0.9552	High Similarity	NPC186838
0.9552	High Similarity	NPC29353
0.9552	High Similarity	NPC477242
0.9552	High Similarity	NPC124784
0.9552	High Similarity	NPC168105
0.9552	High Similarity	NPC194281
0.9552	High Similarity	NPC127447
0.9552	High Similarity	NPC274109
0.9552	High Similarity	NPC66349
0.9552	High Similarity	NPC187826
0.9552	High Similarity	NPC477244
0.9552	High Similarity	NPC231772
0.9552	High Similarity	NPC249606
0.9552	High Similarity	NPC12165
0.9552	High Similarity	NPC150399
0.9552	High Similarity	NPC41461
0.9552	High Similarity	NPC25287
0.9552	High Similarity	NPC13408
0.9552	High Similarity	NPC47815
0.9552	High Similarity	NPC234133
0.9549	High Similarity	NPC144027
0.9549	High Similarity	NPC236974
0.9545	High Similarity	NPC129132
0.9545	High Similarity	NPC205468
0.9545	High Similarity	NPC87231
0.9545	High Similarity	NPC212631
0.9545	High Similarity	NPC203817
0.9545	High Similarity	NPC257756
0.9496	High Similarity	NPC299011
0.9496	High Similarity	NPC130176
0.9496	High Similarity	NPC99454
0.9493	High Similarity	NPC166138
0.9493	High Similarity	NPC18585
0.9493	High Similarity	NPC81697
0.9493	High Similarity	NPC85162
0.9493	High Similarity	NPC107177
0.9493	High Similarity	NPC278249
0.9493	High Similarity	NPC77794
0.9493	High Similarity	NPC106985
0.9493	High Similarity	NPC125894
0.9493	High Similarity	NPC478086
0.9493	High Similarity	NPC185276
0.9493	High Similarity	NPC223812
0.9493	High Similarity	NPC214166
0.9493	High Similarity	NPC316816
0.9489	High Similarity	NPC118840
0.9489	High Similarity	NPC110038
0.9489	High Similarity	NPC324386
0.9489	High Similarity	NPC64908
0.9489	High Similarity	NPC147688
0.9489	High Similarity	NPC96408
0.9489	High Similarity	NPC17170
0.9489	High Similarity	NPC258630
0.9489	High Similarity	NPC282300
0.9489	High Similarity	NPC156190
0.9489	High Similarity	NPC4743
0.9489	High Similarity	NPC312391
0.9489	High Similarity	NPC213322
0.9489	High Similarity	NPC205006
0.9489	High Similarity	NPC103362
0.9489	High Similarity	NPC248372
0.9489	High Similarity	NPC279650
0.9489	High Similarity	NPC166689
0.9489	High Similarity	NPC156590
0.9485	High Similarity	NPC96565
0.9485	High Similarity	NPC216978
0.9485	High Similarity	NPC301217
0.9485	High Similarity	NPC303633
0.9485	High Similarity	NPC217186
0.9485	High Similarity	NPC53181
0.9485	High Similarity	NPC470211
0.9485	High Similarity	NPC55018
0.9485	High Similarity	NPC18260
0.9485	High Similarity	NPC23257
0.9485	High Similarity	NPC220062
0.9485	High Similarity	NPC78913
0.9481	High Similarity	NPC303644
0.9481	High Similarity	NPC317119
0.9481	High Similarity	NPC116632
0.9481	High Similarity	NPC296490
0.9481	High Similarity	NPC32441
0.9481	High Similarity	NPC79943
0.9481	High Similarity	NPC287246
0.9481	High Similarity	NPC162680
0.9481	High Similarity	NPC84585
0.9481	High Similarity	NPC294409
0.9481	High Similarity	NPC209560
0.9481	High Similarity	NPC153979
0.9481	High Similarity	NPC243083

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 NPC124269 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	928
0.2-0.3	1514
0.3-0.4	2514
0.4-0.5	1930
0.5-0.6	1224
0.6-0.7	502
0.7-0.8	159
0.8-0.85	45
0.85-0.9	20
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9556	High Similarity	NPD1549	Phase 2
0.9481	High Similarity	NPD1550	Clinical (unspecified phase)
0.9481	High Similarity	NPD1552	Clinical (unspecified phase)
0.947	High Similarity	NPD1240	Approved
0.9333	High Similarity	NPD1510	Phase 2
0.9328	High Similarity	NPD1607	Approved
0.9286	High Similarity	NPD4378	Clinical (unspecified phase)
0.9265	High Similarity	NPD2796	Approved
0.9149	High Similarity	NPD7410	Clinical (unspecified phase)
0.9078	High Similarity	NPD6799	Approved
0.9034	High Similarity	NPD7411	Suspended
0.8912	High Similarity	NPD2393	Clinical (unspecified phase)
0.8859	High Similarity	NPD7075	Discontinued
0.8851	High Similarity	NPD8443	Clinical (unspecified phase)
0.8844	High Similarity	NPD1934	Approved
0.8836	High Similarity	NPD6599	Discontinued
0.8836	High Similarity	NPD4380	Phase 2
0.8792	High Similarity	NPD3882	Suspended
0.8784	High Similarity	NPD7096	Clinical (unspecified phase)
0.8784	High Similarity	NPD7819	Suspended
0.875	High Similarity	NPD6859	Clinical (unspecified phase)
0.8733	High Similarity	NPD4381	Clinical (unspecified phase)
0.8716	High Similarity	NPD6801	Discontinued
0.8714	High Similarity	NPD1551	Phase 2
0.8681	High Similarity	NPD1511	Approved
0.8662	High Similarity	NPD7421	Clinical (unspecified phase)
0.8658	High Similarity	NPD2801	Approved
0.8601	High Similarity	NPD3750	Approved
0.8562	High Similarity	NPD1512	Approved
0.8543	High Similarity	NPD7768	Phase 2
0.8516	High Similarity	NPD7852	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD2800	Approved
0.8397	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD6166	Phase 2
0.8397	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD2344	Approved
0.8382	Intermediate Similarity	NPD1203	Approved
0.8378	Intermediate Similarity	NPD5403	Approved
0.8369	Intermediate Similarity	NPD6651	Approved
0.8366	Intermediate Similarity	NPD3749	Approved
0.8355	Intermediate Similarity	NPD3817	Phase 2
0.8345	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6832	Phase 2
0.8323	Intermediate Similarity	NPD6959	Discontinued
0.8322	Intermediate Similarity	NPD2935	Discontinued
0.8291	Intermediate Similarity	NPD3818	Discontinued
0.8276	Intermediate Similarity	NPD1243	Approved
0.8255	Intermediate Similarity	NPD920	Approved
0.8252	Intermediate Similarity	NPD2799	Discontinued
0.8252	Intermediate Similarity	NPD3748	Approved
0.825	Intermediate Similarity	NPD5953	Discontinued
0.8243	Intermediate Similarity	NPD5401	Approved
0.8239	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7286	Phase 2
0.8231	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD4628	Phase 3
0.8187	Intermediate Similarity	NPD7074	Phase 3
0.8182	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD2309	Approved
0.8162	Intermediate Similarity	NPD9717	Approved
0.8141	Intermediate Similarity	NPD5494	Approved
0.8125	Intermediate Similarity	NPD7054	Approved
0.8121	Intermediate Similarity	NPD2533	Approved
0.8121	Intermediate Similarity	NPD2532	Approved
0.8121	Intermediate Similarity	NPD2534	Approved
0.8121	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD943	Approved
0.8075	Intermediate Similarity	NPD7472	Approved
0.8071	Intermediate Similarity	NPD4908	Phase 1
0.806	Intermediate Similarity	NPD1548	Phase 1
0.8037	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6797	Phase 2
0.8	Intermediate Similarity	NPD7033	Discontinued
0.8	Intermediate Similarity	NPD5402	Approved
0.7975	Intermediate Similarity	NPD7251	Discontinued
0.7975	Intermediate Similarity	NPD6559	Discontinued
0.7958	Intermediate Similarity	NPD3268	Approved
0.7958	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD2313	Discontinued
0.7956	Intermediate Similarity	NPD1610	Phase 2
0.7956	Intermediate Similarity	NPD422	Phase 1
0.7945	Intermediate Similarity	NPD6099	Approved
0.7945	Intermediate Similarity	NPD6100	Approved
0.7929	Intermediate Similarity	NPD2798	Approved
0.7927	Intermediate Similarity	NPD7808	Phase 3
0.7926	Intermediate Similarity	NPD9545	Approved
0.7925	Intermediate Similarity	NPD6232	Discontinued
0.7905	Intermediate Similarity	NPD2654	Approved
0.7899	Intermediate Similarity	NPD3972	Approved
0.7888	Intermediate Similarity	NPD7473	Discontinued
0.7877	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3926	Phase 2
0.7857	Intermediate Similarity	NPD2797	Approved
0.7848	Intermediate Similarity	NPD919	Approved
0.782	Intermediate Similarity	NPD1241	Discontinued
0.7818	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3226	Approved
0.7791	Intermediate Similarity	NPD5844	Phase 1
0.7778	Intermediate Similarity	NPD9493	Approved
0.7755	Intermediate Similarity	NPD4308	Phase 3
0.775	Intermediate Similarity	NPD1247	Approved
0.7744	Intermediate Similarity	NPD1729	Discontinued
0.7733	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1019	Discontinued
0.7671	Intermediate Similarity	NPD230	Phase 1
0.7671	Intermediate Similarity	NPD1933	Approved
0.7662	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD3225	Approved
0.7651	Intermediate Similarity	NPD2346	Discontinued
0.7651	Intermediate Similarity	NPD6104	Discontinued
0.7643	Intermediate Similarity	NPD1608	Approved
0.7606	Intermediate Similarity	NPD3267	Approved
0.7606	Intermediate Similarity	NPD3266	Approved
0.7595	Intermediate Similarity	NPD1465	Phase 2
0.7586	Intermediate Similarity	NPD6798	Discontinued
0.7586	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD411	Approved
0.7586	Intermediate Similarity	NPD1296	Phase 2
0.7582	Intermediate Similarity	NPD7390	Discontinued
0.758	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4360	Phase 2
0.7572	Intermediate Similarity	NPD4363	Phase 3
0.7551	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD447	Suspended
0.7551	Intermediate Similarity	NPD5124	Phase 1
0.7547	Intermediate Similarity	NPD2296	Approved
0.7547	Intermediate Similarity	NPD4288	Approved
0.7532	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4662	Approved
0.7532	Intermediate Similarity	NPD4661	Approved
0.7529	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4361	Phase 2
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD5711	Approved
0.7483	Intermediate Similarity	NPD3142	Approved
0.7483	Intermediate Similarity	NPD4307	Phase 2
0.7483	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3140	Approved
0.7466	Intermediate Similarity	NPD3764	Approved
0.7452	Intermediate Similarity	NPD7458	Discontinued
0.7451	Intermediate Similarity	NPD3887	Approved
0.7451	Intermediate Similarity	NPD2354	Approved
0.7448	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6355	Discontinued
0.7429	Intermediate Similarity	NPD17	Approved
0.7421	Intermediate Similarity	NPD6279	Approved
0.7421	Intermediate Similarity	NPD6280	Approved
0.7417	Intermediate Similarity	NPD1471	Phase 3
0.7417	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1876	Approved
0.741	Intermediate Similarity	NPD1894	Discontinued
0.74	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4625	Phase 3
0.7397	Intermediate Similarity	NPD3027	Phase 3
0.7394	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1481	Phase 2
0.7379	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1164	Approved
0.7361	Intermediate Similarity	NPD1470	Approved
0.736	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5889	Approved
0.7358	Intermediate Similarity	NPD5890	Approved
0.7355	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4749	Approved
0.7342	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD4287	Approved
0.7324	Intermediate Similarity	NPD1201	Approved
0.7324	Intermediate Similarity	NPD1535	Discovery
0.7317	Intermediate Similarity	NPD7199	Phase 2
0.7312	Intermediate Similarity	NPD7577	Discontinued
0.7312	Intermediate Similarity	NPD6844	Discontinued
0.7305	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3751	Discontinued
0.7303	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2353	Approved
0.7297	Intermediate Similarity	NPD6233	Phase 2
0.729	Intermediate Similarity	NPD7440	Discontinued
0.7289	Intermediate Similarity	NPD2403	Approved
0.7273	Intermediate Similarity	NPD7003	Approved
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD6808	Phase 2
0.7261	Intermediate Similarity	NPD5049	Phase 3
0.726	Intermediate Similarity	NPD2861	Phase 2
0.726	Intermediate Similarity	NPD9494	Approved
0.7257	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7213	Phase 3
0.7244	Intermediate Similarity	NPD7212	Phase 2
0.7239	Intermediate Similarity	NPD6971	Discontinued
0.7237	Intermediate Similarity	NPD5404	Approved
0.7237	Intermediate Similarity	NPD5405	Approved
0.7237	Intermediate Similarity	NPD5406	Approved
0.7237	Intermediate Similarity	NPD4476	Approved
0.7237	Intermediate Similarity	NPD5408	Approved
0.7237	Intermediate Similarity	NPD4477	Approved
0.7235	Intermediate Similarity	NPD3658	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