NPASS Compound

Structure

NPC473664 OpenBabel07101718302D 42 44 0 0 0 0 0 0 0 0999 V2000 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 -4.3301 0.5000 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 5.1962 -1.0000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 2.0000 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 -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 2.5981 -1.5000 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 0.0000 -3.0000 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 3.4641 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 -1.7321 -0.0000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 2.0000 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 -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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 7 37 1 0 0 0 0 8 38 1 0 0 0 0 9 39 1 0 0 0 0 10 40 1 0 0 0 0 11 41 1 0 0 0 0 12 15 1 0 0 0 0 12 20 2 0 0 0 0 13 16 1 0 0 0 0 13 21 2 0 0 0 0 14 17 1 0 0 0 0 14 22 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 28 1 0 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 24 33 2 0 0 0 0 25 29 2 0 0 0 0 25 32 1 0 0 0 0 26 37 1 0 0 0 0 27 30 2 0 0 0 0 27 38 1 0 0 0 0 28 32 2 0 0 0 0 28 39 1 0 0 0 0 29 34 1 0 0 0 0 30 31 1 0 0 0 0 30 33 1 0 0 0 0 31 35 1 0 0 0 0 31 36 2 0 0 0 0 32 40 1 0 0 0 0 33 42 1 0 0 0 0 34 35 2 0 0 0 0 34 42 1 0 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.31
Volume:	620.777
LogP:	8.42
LogD:	4.776
LogS:	-6.88
# Rotatable Bonds:	12
TPSA:	76.36
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.202
Synthetic Accessibility Score:	3.423
Fsp3:	0.4
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.763
MDCK Permeability:	1.2510407032095827e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.312
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.654
30% Bioavailability (F30%):	0.125

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	52.80228042602539%
Volume Distribution (VD):	1.758
Pgp-substrate:	51.25082778930664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.782
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.917
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.823
CYP3A4-inhibitor:	0.458
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	8.853
Half-life (T1/2):	0.03

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.986
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.359
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.324

Download Data

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

Natural Product: NPC473664

Natural Product ID:	NPC473664
*Common Name:**	2-[3,4-Dimethoxy-2,6-Bis(3-Methylbut-2-Enyl)Phenyl]-3,5,7-Trimethoxy-8-(3-Methylbut-2-Enyl)Chromen-4-One
IUPAC Name:	2-[3,4-dimethoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-3,5,7-trimethoxy-8-(3-methylbut-2-enyl)chromen-4-one
Synonyms:
Standard InCHIKey:	LTEKIAJZJSEKRE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C35H44O7/c1-20(2)12-15-23-18-28(39-9)32(40-10)25(17-14-22(5)6)29(23)34-35(41-11)31(36)30-27(38-8)19-26(37-7)24(33(30)42-34)16-13-21(3)4/h12-14,18-19H,15-17H2,1-11H3
SMILES:	COc1c(OC)cc(c(c1CC=C(C)C)c1oc2c(CC=C(C)C)c(OC)cc(c2c(=O)c1OC)OC)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448520
PubChem CID:	44584417
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003587] 2'-prenylated flavones

*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
NPO27127	Petalostemum purpureum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8289060]
NPO27127	Petalostemum purpureum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	25.0	ug.mL-1	PMID[482541]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MIC	=	25.0	ug.mL-1	PMID[482541]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[482541]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	5.0	ug.mL-1	PMID[482541]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	5.0	ug.mL-1	PMID[482541]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	5.0	ug.mL-1	PMID[482541]

☑ 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 NPC473664 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	542
0.1-0.2	1881
0.2-0.3	4649
0.3-0.4	11236
0.4-0.5	6766
0.5-0.6	3925
0.6-0.7	5668
0.7-0.8	5141
0.8-0.85	2007
0.85-0.9	760
0.9-0.95	120
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9542	High Similarity	NPC475144
0.9388	High Similarity	NPC310259
0.9351	High Similarity	NPC474239
0.9324	High Similarity	NPC299923
0.9247	High Similarity	NPC29536
0.9231	High Similarity	NPC474240
0.9216	High Similarity	NPC475799
0.9216	High Similarity	NPC13779
0.92	High Similarity	NPC181250
0.92	High Similarity	NPC69752
0.9184	High Similarity	NPC9966
0.9184	High Similarity	NPC70853
0.9172	High Similarity	NPC475888
0.9161	High Similarity	NPC299436
0.9156	High Similarity	NPC273843
0.9139	High Similarity	NPC259058
0.9139	High Similarity	NPC201547
0.9133	High Similarity	NPC476342
0.9133	High Similarity	NPC261548
0.9122	High Similarity	NPC113089
0.9103	High Similarity	NPC475883
0.9103	High Similarity	NPC474351
0.9079	High Similarity	NPC472535
0.9079	High Similarity	NPC474388
0.9079	High Similarity	NPC76376
0.9079	High Similarity	NPC474170
0.9079	High Similarity	NPC236769
0.9067	High Similarity	NPC117463
0.906	High Similarity	NPC471590
0.906	High Similarity	NPC136278
0.9054	High Similarity	NPC476054
0.9045	High Similarity	NPC201800
0.9045	High Similarity	NPC211107
0.9038	High Similarity	NPC474287
0.9038	High Similarity	NPC246478
0.9038	High Similarity	NPC475886
0.9032	High Similarity	NPC165977
0.9032	High Similarity	NPC217677
0.9026	High Similarity	NPC80534
0.9026	High Similarity	NPC56786
0.9026	High Similarity	NPC133392
0.902	High Similarity	NPC471982
0.902	High Similarity	NPC40033
0.9013	High Similarity	NPC189270
0.9013	High Similarity	NPC5840
0.9013	High Similarity	NPC50728
0.9013	High Similarity	NPC219330
0.9013	High Similarity	NPC177839
0.9013	High Similarity	NPC166753
0.9007	High Similarity	NPC476058
0.9	High Similarity	NPC302408
0.9	High Similarity	NPC283002
0.9	High Similarity	NPC40818
0.9	High Similarity	NPC215932
0.9	High Similarity	NPC110639
0.9	High Similarity	NPC106461
0.9	High Similarity	NPC14958
0.8993	High Similarity	NPC189650
0.8981	High Similarity	NPC278052
0.8981	High Similarity	NPC474187
0.8981	High Similarity	NPC66288
0.8981	High Similarity	NPC40491
0.8981	High Similarity	NPC474186
0.8968	High Similarity	NPC257277
0.8961	High Similarity	NPC179126
0.8961	High Similarity	NPC270620
0.8961	High Similarity	NPC246204
0.8961	High Similarity	NPC162351
0.8961	High Similarity	NPC78326
0.8961	High Similarity	NPC58382
0.8961	High Similarity	NPC472408
0.8961	High Similarity	NPC236223
0.8954	High Similarity	NPC205046
0.8954	High Similarity	NPC304295
0.8954	High Similarity	NPC59162
0.8947	High Similarity	NPC159103
0.894	High Similarity	NPC205522
0.894	High Similarity	NPC259632
0.894	High Similarity	NPC85233
0.894	High Similarity	NPC474999
0.894	High Similarity	NPC470511
0.894	High Similarity	NPC62536
0.894	High Similarity	NPC33265
0.8933	High Similarity	NPC165512
0.8924	High Similarity	NPC229632
0.8924	High Similarity	NPC302741
0.8917	High Similarity	NPC56085
0.8917	High Similarity	NPC36217
0.8917	High Similarity	NPC14353
0.8917	High Similarity	NPC320359
0.8917	High Similarity	NPC228785
0.8917	High Similarity	NPC477164
0.8903	High Similarity	NPC284353
0.8903	High Similarity	NPC471746
0.8903	High Similarity	NPC189960
0.8903	High Similarity	NPC34725
0.8903	High Similarity	NPC241774
0.8903	High Similarity	NPC32557
0.8903	High Similarity	NPC276059
0.8903	High Similarity	NPC226025
0.8903	High Similarity	NPC122623
0.8896	High Similarity	NPC157784
0.8896	High Similarity	NPC82325
0.8896	High Similarity	NPC63187
0.8896	High Similarity	NPC134677
0.8896	High Similarity	NPC37684
0.8896	High Similarity	NPC279989
0.8896	High Similarity	NPC123886
0.8896	High Similarity	NPC166201
0.8882	High Similarity	NPC195202
0.8882	High Similarity	NPC10304
0.8882	High Similarity	NPC63256
0.8875	High Similarity	NPC39091
0.8875	High Similarity	NPC470462
0.8868	High Similarity	NPC186686
0.8868	High Similarity	NPC7483
0.8868	High Similarity	NPC270837
0.8868	High Similarity	NPC236132
0.8868	High Similarity	NPC470459
0.8867	High Similarity	NPC23955
0.8867	High Similarity	NPC293201
0.8861	High Similarity	NPC61010
0.8859	High Similarity	NPC185607
0.8854	High Similarity	NPC210459
0.8854	High Similarity	NPC280680
0.8854	High Similarity	NPC100123
0.8846	High Similarity	NPC265511
0.8846	High Similarity	NPC178854
0.8846	High Similarity	NPC248299
0.8846	High Similarity	NPC470328
0.8846	High Similarity	NPC200388
0.8846	High Similarity	NPC3980
0.8846	High Similarity	NPC472626
0.8846	High Similarity	NPC100916
0.8846	High Similarity	NPC474983
0.8846	High Similarity	NPC55619
0.8846	High Similarity	NPC209614
0.8839	High Similarity	NPC86485
0.8839	High Similarity	NPC279930
0.8839	High Similarity	NPC476631
0.8839	High Similarity	NPC128961
0.8831	High Similarity	NPC54394
0.8831	High Similarity	NPC200740
0.8831	High Similarity	NPC28274
0.8831	High Similarity	NPC50403
0.8831	High Similarity	NPC133953
0.8831	High Similarity	NPC125062
0.8831	High Similarity	NPC474414
0.8831	High Similarity	NPC252933
0.8824	High Similarity	NPC177298
0.8824	High Similarity	NPC238366
0.8824	High Similarity	NPC328119
0.8824	High Similarity	NPC48479
0.882	High Similarity	NPC218226
0.882	High Similarity	NPC470456
0.882	High Similarity	NPC158761
0.882	High Similarity	NPC150131
0.8816	High Similarity	NPC12200
0.8812	High Similarity	NPC275780
0.8812	High Similarity	NPC239752
0.8812	High Similarity	NPC293319
0.8812	High Similarity	NPC472450
0.8812	High Similarity	NPC470457
0.8805	High Similarity	NPC78332
0.8805	High Similarity	NPC294965
0.8805	High Similarity	NPC108767
0.8797	High Similarity	NPC321399
0.8797	High Similarity	NPC282009
0.8797	High Similarity	NPC470326
0.8797	High Similarity	NPC471973
0.8797	High Similarity	NPC287328
0.879	High Similarity	NPC472963
0.879	High Similarity	NPC472438
0.879	High Similarity	NPC19097
0.879	High Similarity	NPC284820
0.879	High Similarity	NPC300727
0.879	High Similarity	NPC203891
0.879	High Similarity	NPC136674
0.879	High Similarity	NPC476981
0.879	High Similarity	NPC101830
0.879	High Similarity	NPC471479
0.879	High Similarity	NPC29841
0.879	High Similarity	NPC241904
0.879	High Similarity	NPC471515
0.879	High Similarity	NPC78302
0.879	High Similarity	NPC237418
0.879	High Similarity	NPC236796
0.879	High Similarity	NPC235215
0.879	High Similarity	NPC110070
0.879	High Similarity	NPC7973
0.879	High Similarity	NPC473272
0.8782	High Similarity	NPC477503
0.8782	High Similarity	NPC470327
0.8782	High Similarity	NPC45849
0.8782	High Similarity	NPC200761
0.8782	High Similarity	NPC234255
0.8776	High Similarity	NPC72452
0.8776	High Similarity	NPC61546
0.8774	High Similarity	NPC55205
0.8774	High Similarity	NPC301123

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 NPC473664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	1008
0.2-0.3	1812
0.3-0.4	2728
0.4-0.5	1764
0.5-0.6	878
0.6-0.7	362
0.7-0.8	116
0.8-0.85	23
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8903	High Similarity	NPD3817	Phase 2
0.8684	High Similarity	NPD4378	Clinical (unspecified phase)
0.8679	High Similarity	NPD5494	Approved
0.8599	High Similarity	NPD7819	Suspended
0.8599	High Similarity	NPD2393	Clinical (unspecified phase)
0.8599	High Similarity	NPD2801	Approved
0.8535	High Similarity	NPD1934	Approved
0.8509	High Similarity	NPD1247	Approved
0.8506	High Similarity	NPD1512	Approved
0.85	High Similarity	NPD919	Approved
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8481	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7473	Discontinued
0.84	Intermediate Similarity	NPD2796	Approved
0.8377	Intermediate Similarity	NPD1511	Approved
0.8354	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6166	Phase 2
0.8354	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD7808	Phase 3
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8302	Intermediate Similarity	NPD6801	Discontinued
0.8293	Intermediate Similarity	NPD3926	Phase 2
0.8258	Intermediate Similarity	NPD6799	Approved
0.8204	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6599	Discontinued
0.8166	Intermediate Similarity	NPD7251	Discontinued
0.8107	Intermediate Similarity	NPD6797	Phase 2
0.8095	Intermediate Similarity	NPD7054	Approved
0.8095	Intermediate Similarity	NPD5844	Phase 1
0.8086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD4380	Phase 2
0.8061	Intermediate Similarity	NPD6959	Discontinued
0.8047	Intermediate Similarity	NPD7472	Approved
0.8047	Intermediate Similarity	NPD7074	Phase 3
0.8036	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD3748	Approved
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1243	Approved
0.7875	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD5402	Approved
0.7857	Intermediate Similarity	NPD1510	Phase 2
0.7821	Intermediate Similarity	NPD1549	Phase 2
0.7818	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1465	Phase 2
0.7791	Intermediate Similarity	NPD7411	Suspended
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5403	Approved
0.7764	Intermediate Similarity	NPD920	Approved
0.7751	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5401	Approved
0.775	Intermediate Similarity	NPD2534	Approved
0.775	Intermediate Similarity	NPD2532	Approved
0.775	Intermediate Similarity	NPD2533	Approved
0.7722	Intermediate Similarity	NPD3750	Approved
0.7712	Intermediate Similarity	NPD1240	Approved
0.7711	Intermediate Similarity	NPD7768	Phase 2
0.7688	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2800	Approved
0.764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1607	Approved
0.7602	Intermediate Similarity	NPD2403	Approved
0.7602	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3226	Approved
0.7556	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1933	Approved
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7532	Intermediate Similarity	NPD1471	Phase 3
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7469	Intermediate Similarity	NPD7390	Discontinued
0.7468	Intermediate Similarity	NPD6100	Approved
0.7468	Intermediate Similarity	NPD2935	Discontinued
0.7468	Intermediate Similarity	NPD6099	Approved
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3749	Approved
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6559	Discontinued
0.7438	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD37	Approved
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7405	Intermediate Similarity	NPD2799	Discontinued
0.7405	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4966	Approved
0.7396	Intermediate Similarity	NPD4965	Approved
0.7396	Intermediate Similarity	NPD4967	Phase 2
0.7389	Intermediate Similarity	NPD6651	Approved
0.7372	Intermediate Similarity	NPD943	Approved
0.7355	Intermediate Similarity	NPD2313	Discontinued
0.7341	Intermediate Similarity	NPD5242	Approved
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7325	Intermediate Similarity	NPD447	Suspended
0.731	Intermediate Similarity	NPD6234	Discontinued
0.7303	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7229	Phase 3
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7235	Intermediate Similarity	NPD5353	Approved
0.7226	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2654	Approved
0.7219	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2798	Approved
0.7184	Intermediate Similarity	NPD5711	Approved
0.7184	Intermediate Similarity	NPD5710	Approved
0.7178	Intermediate Similarity	NPD4628	Phase 3
0.7178	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7286	Phase 2
0.7167	Intermediate Similarity	NPD8313	Approved
0.7167	Intermediate Similarity	NPD8312	Approved
0.716	Intermediate Similarity	NPD6386	Approved
0.716	Intermediate Similarity	NPD6385	Approved
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7133	Intermediate Similarity	NPD1651	Approved
0.7119	Intermediate Similarity	NPD7228	Approved
0.7114	Intermediate Similarity	NPD5536	Phase 2
0.7107	Intermediate Similarity	NPD6355	Discontinued
0.7107	Intermediate Similarity	NPD230	Phase 1
0.7099	Intermediate Similarity	NPD2344	Approved
0.7095	Intermediate Similarity	NPD5953	Discontinued
0.7086	Intermediate Similarity	NPD17	Approved
0.707	Intermediate Similarity	NPD4625	Phase 3
0.707	Intermediate Similarity	NPD3027	Phase 3
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7068	Intermediate Similarity	NPD7697	Approved
0.7068	Intermediate Similarity	NPD7696	Phase 3
0.7068	Intermediate Similarity	NPD7698	Approved
0.7066	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD5090	Approved
0.7059	Intermediate Similarity	NPD5089	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.7051	Intermediate Similarity	NPD3018	Phase 2
0.7037	Intermediate Similarity	NPD8285	Discontinued
0.7035	Intermediate Similarity	NPD4288	Approved
0.7031	Intermediate Similarity	NPD7871	Phase 2
0.7031	Intermediate Similarity	NPD7870	Phase 2
0.703	Intermediate Similarity	NPD3887	Approved
0.7029	Intermediate Similarity	NPD8127	Discontinued
0.7025	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6798	Discontinued
0.7025	Intermediate Similarity	NPD3268	Approved
0.7022	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3146	Approved
0.7005	Intermediate Similarity	NPD4363	Phase 3
0.7005	Intermediate Similarity	NPD4360	Phase 2
0.7	Intermediate Similarity	NPD6780	Approved
0.7	Intermediate Similarity	NPD6779	Approved
0.7	Intermediate Similarity	NPD6778	Approved
0.7	Intermediate Similarity	NPD6777	Approved
0.7	Intermediate Similarity	NPD6782	Approved
0.7	Intermediate Similarity	NPD6776	Approved
0.7	Intermediate Similarity	NPD6781	Approved
0.6994	Remote Similarity	NPD2353	Approved
0.6994	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD8032	Phase 2
0.6977	Remote Similarity	NPD4585	Approved
0.697	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1876	Approved
0.6962	Remote Similarity	NPD7095	Approved
0.6961	Remote Similarity	NPD7240	Approved
0.6959	Remote Similarity	NPD5283	Phase 1
0.6948	Remote Similarity	NPD1608	Approved
0.6948	Remote Similarity	NPD2981	Phase 2
0.6941	Remote Similarity	NPD7458	Discontinued
0.6941	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7874	Approved
0.6939	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2979	Phase 3
0.6937	Remote Similarity	NPD4307	Phase 2
0.6936	Remote Similarity	NPD5978	Approved
0.6936	Remote Similarity	NPD5977	Approved
0.6933	Remote Similarity	NPD2438	Suspended
0.6928	Remote Similarity	NPD2309	Approved
0.6928	Remote Similarity	NPD6190	Approved
0.6927	Remote Similarity	NPD5005	Approved
0.6927	Remote Similarity	NPD5006	Approved
0.6923	Remote Similarity	NPD2797	Approved
0.6923	Remote Similarity	NPD7701	Phase 2
0.6918	Remote Similarity	NPD1296	Phase 2

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