NPASS Compound

Structure

CID318432 OpenBabel06191716142D 32 35 0 0 1 0 0 0 0 0999 V2000 0.0000 -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 -0.5000 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 5.1962 -2.0000 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 0.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -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 3.4641 -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 -0.8660 -0.5000 0.0000 C 0 0 3 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 4.3301 -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 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 12 1 0 0 0 0 2 18 1 0 0 0 0 3 9 2 0 0 0 0 3 14 1 0 0 0 0 4 9 1 0 0 0 0 4 15 2 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 10 1 0 0 0 0 6 17 2 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 19 2 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 31 1 0 0 0 0 12 13 2 0 0 0 0 12 19 1 0 0 0 0 13 23 1 0 0 0 0 14 20 2 0 0 0 0 14 24 1 0 0 0 0 15 20 1 0 0 0 0 15 25 1 0 0 0 0 16 21 2 0 0 0 0 16 26 1 0 0 0 0 17 21 1 0 0 0 0 17 27 1 0 0 0 0 18 32 1 0 0 0 0 19 32 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 30 2 0 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.09
Volume:	416.38
LogP:	2.855
LogD:	1.734
LogS:	-4.037
# Rotatable Bonds:	4
TPSA:	177.14
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.181
Synthetic Accessibility Score:	3.405
Fsp3:	0.136
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.347
MDCK Permeability:	5.820998467243044e-06
Pgp-inhibitor:	0.013
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.278
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	92.59221649169922%
Volume Distribution (VD):	0.509
Pgp-substrate:	4.8555192947387695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.449
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.592
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	15.298
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.518
AMES Toxicity:	0.397
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.977
Carcinogencity:	0.043
Eye Corrosion:	0.003
Eye Irritation:	0.928
Respiratory Toxicity:	0.054

Download Data

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

Natural Product: NPC318432

Natural Product ID:	NPC318432
*Common Name:**	7-O-Galloyltricetifavan
IUPAC Name:	[5-hydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-7-yl] 3,4,5-trihydroxybenzoate
Synonyms:	7-O-Galloyltricetifavan; 7-O-Galloyltricetinflavan
Standard InCHIKey:	XQLJWQWRTLHKGO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H18O10/c23-13-7-11(31-22(30)10-5-16(26)21(29)17(27)6-10)8-19-12(13)1-2-18(32-19)9-3-14(24)20(28)15(25)4-9/h3-8,18,23-29H,1-2H2
SMILES:	C1CC2=C(C=C(C=C2OC1C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498441
PubChem CID:	11669392
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002991] Hydroxyflavonoids [CHEMONTID:0002992] 5-hydroxyflavonoids

*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
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16724853]
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16724853]
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Others	11

Activity Type	# Activity
Cell Line	4
Individual Protein	2
Organism	4
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	120.0	ug.mL-1	PMID[515630]
NPT189	Cell Line	Vero	Chlorocebus aethiops	MNCC	=	31.3	ug ml-1	PMID[515630]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	=	110.0	ug.mL-1	PMID[515630]
NPT616	Cell Line	MDCK	Canis lupus familiaris	MNCC	=	62.5	ug ml-1	PMID[515630]
NPT1602	Individual Protein	Neuraminidase	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	15.7	ug.mL-1	PMID[515631]
NPT1602	Individual Protein	Neuraminidase	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	logIC50	=	1.196	n.a.	PMID[515631]
NPT27	Others	Unspecified		CC50	=	95.0	ug.mL-1	PMID[515630]
NPT27	Others	Unspecified		MNCC	=	25.0	ug ml-1	PMID[515630]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	IC50	=	5.0	ug.mL-1	PMID[515630]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	19.0	n.a.	PMID[515630]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	30.0	ug.mL-1	PMID[515630]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	4.0	n.a.	PMID[515630]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	15.7	ug.mL-1	PMID[515630]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	7.0	n.a.	PMID[515630]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	=	12.5	ug.mL-1	PMID[515630]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	7.6	n.a.	PMID[515630]

☑ 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 NPC318432 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	386
0.1-0.2	1690
0.2-0.3	4278
0.3-0.4	9359
0.4-0.5	8633
0.5-0.6	3481
0.6-0.7	4915
0.7-0.8	6407
0.8-0.85	2868
0.85-0.9	635
0.9-0.95	23
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC250436
0.9866	High Similarity	NPC104983
0.9866	High Similarity	NPC300845
0.9866	High Similarity	NPC88803
0.9866	High Similarity	NPC291948
0.9801	High Similarity	NPC24164
0.98	High Similarity	NPC160512
0.98	High Similarity	NPC289322
0.98	High Similarity	NPC114179
0.98	High Similarity	NPC156818
0.98	High Similarity	NPC68324
0.98	High Similarity	NPC38779
0.9735	High Similarity	NPC87317
0.9671	High Similarity	NPC53889
0.9533	High Similarity	NPC474656
0.9427	High Similarity	NPC473818
0.9423	High Similarity	NPC142614
0.9267	High Similarity	NPC107636
0.9195	High Similarity	NPC262282
0.9177	High Similarity	NPC471788
0.9172	High Similarity	NPC476372
0.9172	High Similarity	NPC476371
0.9167	High Similarity	NPC289346
0.9167	High Similarity	NPC24627
0.9156	High Similarity	NPC222185
0.913	High Similarity	NPC289396
0.913	High Similarity	NPC212038
0.913	High Similarity	NPC65333
0.913	High Similarity	NPC100251
0.913	High Similarity	NPC271848
0.913	High Similarity	NPC81332
0.913	High Similarity	NPC262580
0.9119	High Similarity	NPC207575
0.9119	High Similarity	NPC13481
0.9114	High Similarity	NPC121290
0.9103	High Similarity	NPC37502
0.9103	High Similarity	NPC40702
0.9103	High Similarity	NPC267627
0.9085	High Similarity	NPC75695
0.908	High Similarity	NPC297574
0.9074	High Similarity	NPC98583
0.9073	High Similarity	NPC142528
0.9068	High Similarity	NPC204937
0.9068	High Similarity	NPC476365
0.9068	High Similarity	NPC149011
0.9067	High Similarity	NPC268515
0.9067	High Similarity	NPC40222
0.9051	High Similarity	NPC90905
0.9051	High Similarity	NPC4013
0.9051	High Similarity	NPC471745
0.9051	High Similarity	NPC33298
0.9051	High Similarity	NPC285108
0.9045	High Similarity	NPC476373
0.9038	High Similarity	NPC247713
0.9012	High Similarity	NPC67134
0.9012	High Similarity	NPC47140
0.8994	High Similarity	NPC67959
0.8987	High Similarity	NPC158188
0.8987	High Similarity	NPC112418
0.8987	High Similarity	NPC142252
0.8981	High Similarity	NPC24339
0.8981	High Similarity	NPC166456
0.8981	High Similarity	NPC98083
0.8981	High Similarity	NPC7543
0.8981	High Similarity	NPC94220
0.8974	High Similarity	NPC165483
0.897	High Similarity	NPC80956
0.8968	High Similarity	NPC178134
0.8963	High Similarity	NPC67629
0.8963	High Similarity	NPC79736
0.8957	High Similarity	NPC172033
0.8957	High Similarity	NPC88560
0.8957	High Similarity	NPC175230
0.8954	High Similarity	NPC1612
0.8954	High Similarity	NPC183959
0.8954	High Similarity	NPC473091
0.8951	High Similarity	NPC180768
0.8944	High Similarity	NPC260266
0.8944	High Similarity	NPC243877
0.8944	High Similarity	NPC14662
0.8933	High Similarity	NPC226738
0.8933	High Similarity	NPC22176
0.8933	High Similarity	NPC190587
0.8933	High Similarity	NPC121573
0.8933	High Similarity	NPC134975
0.8931	High Similarity	NPC476247
0.8931	High Similarity	NPC477841
0.8931	High Similarity	NPC219927
0.8924	High Similarity	NPC203020
0.8924	High Similarity	NPC471744
0.8924	High Similarity	NPC101731
0.8924	High Similarity	NPC239966
0.8917	High Similarity	NPC108456
0.8917	High Similarity	NPC1913
0.8916	High Similarity	NPC208797
0.8916	High Similarity	NPC117668
0.8916	High Similarity	NPC53680
0.891	High Similarity	NPC203757
0.8909	High Similarity	NPC476623
0.8909	High Similarity	NPC267549
0.8909	High Similarity	NPC476621
0.8909	High Similarity	NPC476622
0.8909	High Similarity	NPC476620
0.8909	High Similarity	NPC476618
0.8909	High Similarity	NPC476619
0.8903	High Similarity	NPC106976
0.8896	High Similarity	NPC476370
0.8889	High Similarity	NPC149300
0.8889	High Similarity	NPC294852
0.8889	High Similarity	NPC476394
0.8889	High Similarity	NPC280493
0.8889	High Similarity	NPC98809
0.8889	High Similarity	NPC188679
0.8889	High Similarity	NPC476279
0.8889	High Similarity	NPC321011
0.8882	High Similarity	NPC471823
0.8882	High Similarity	NPC320741
0.8882	High Similarity	NPC171985
0.8882	High Similarity	NPC224851
0.8868	High Similarity	NPC139540
0.8868	High Similarity	NPC305987
0.8868	High Similarity	NPC113163
0.8868	High Similarity	NPC177100
0.8868	High Similarity	NPC165970
0.8868	High Similarity	NPC84324
0.8868	High Similarity	NPC134783
0.8868	High Similarity	NPC228383
0.8868	High Similarity	NPC109061
0.8868	High Similarity	NPC66618
0.8868	High Similarity	NPC288131
0.8861	High Similarity	NPC284127
0.8861	High Similarity	NPC74319
0.8861	High Similarity	NPC117418
0.8861	High Similarity	NPC53545
0.8861	High Similarity	NPC476410
0.8861	High Similarity	NPC172202
0.8861	High Similarity	NPC287872
0.8861	High Similarity	NPC160780
0.8861	High Similarity	NPC289811
0.8854	High Similarity	NPC54928
0.8848	High Similarity	NPC472991
0.8848	High Similarity	NPC144097
0.8848	High Similarity	NPC61904
0.8848	High Similarity	NPC472992
0.8846	High Similarity	NPC192083
0.8846	High Similarity	NPC18727
0.8846	High Similarity	NPC298692
0.8846	High Similarity	NPC197188
0.8846	High Similarity	NPC291510
0.8846	High Similarity	NPC469888
0.8846	High Similarity	NPC43872
0.8846	High Similarity	NPC144801
0.8846	High Similarity	NPC74924
0.8846	High Similarity	NPC213896
0.8846	High Similarity	NPC116850
0.8846	High Similarity	NPC238672
0.8841	High Similarity	NPC219600
0.8841	High Similarity	NPC166674
0.8841	High Similarity	NPC46640
0.8841	High Similarity	NPC476374
0.8841	High Similarity	NPC34436
0.8841	High Similarity	NPC473550
0.8841	High Similarity	NPC472993
0.8841	High Similarity	NPC263119
0.8839	High Similarity	NPC204515
0.8834	High Similarity	NPC181778
0.8831	High Similarity	NPC105512
0.8827	High Similarity	NPC45400
0.8827	High Similarity	NPC116745
0.8824	High Similarity	NPC95864
0.8824	High Similarity	NPC472969
0.882	High Similarity	NPC477840
0.882	High Similarity	NPC36
0.882	High Similarity	NPC58223
0.882	High Similarity	NPC7688
0.882	High Similarity	NPC7154
0.882	High Similarity	NPC165720
0.882	High Similarity	NPC125039
0.882	High Similarity	NPC36916
0.882	High Similarity	NPC72787
0.8812	High Similarity	NPC291957
0.8812	High Similarity	NPC14030
0.8812	High Similarity	NPC220912
0.8805	High Similarity	NPC119125
0.8805	High Similarity	NPC166277
0.8805	High Similarity	NPC155101
0.8802	High Similarity	NPC8940
0.8802	High Similarity	NPC125352
0.8797	High Similarity	NPC156057
0.8797	High Similarity	NPC222689
0.8797	High Similarity	NPC162869
0.8797	High Similarity	NPC472860
0.8797	High Similarity	NPC471209
0.8797	High Similarity	NPC99597
0.8797	High Similarity	NPC474836
0.8797	High Similarity	NPC63454
0.8797	High Similarity	NPC133984
0.8797	High Similarity	NPC129684
0.8797	High Similarity	NPC291508
0.8797	High Similarity	NPC183851

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 NPC318432 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	361
0.1-0.2	932
0.2-0.3	1855
0.3-0.4	2570
0.4-0.5	1785
0.5-0.6	1008
0.6-0.7	452
0.7-0.8	136
0.8-0.85	42
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9866	High Similarity	NPD4868	Clinical (unspecified phase)
0.913	High Similarity	NPD7993	Clinical (unspecified phase)
0.8968	High Similarity	NPD1465	Phase 2
0.8846	High Similarity	NPD2393	Clinical (unspecified phase)
0.882	High Similarity	NPD6167	Clinical (unspecified phase)
0.882	High Similarity	NPD6166	Phase 2
0.882	High Similarity	NPD6168	Clinical (unspecified phase)
0.8782	High Similarity	NPD1934	Approved
0.8773	High Similarity	NPD5844	Phase 1
0.8598	High Similarity	NPD3818	Discontinued
0.8563	High Similarity	NPD4338	Clinical (unspecified phase)
0.8506	High Similarity	NPD1511	Approved
0.8494	Intermediate Similarity	NPD7074	Phase 3
0.8491	Intermediate Similarity	NPD2801	Approved
0.8481	Intermediate Similarity	NPD7411	Suspended
0.8447	Intermediate Similarity	NPD7075	Discontinued
0.8447	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD3817	Phase 2
0.8434	Intermediate Similarity	NPD7054	Approved
0.8418	Intermediate Similarity	NPD4380	Phase 2
0.8397	Intermediate Similarity	NPD1512	Approved
0.8389	Intermediate Similarity	NPD230	Phase 1
0.8385	Intermediate Similarity	NPD3882	Suspended
0.8383	Intermediate Similarity	NPD7472	Approved
0.8354	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD6797	Phase 2
0.8301	Intermediate Similarity	NPD1549	Phase 2
0.8284	Intermediate Similarity	NPD7251	Discontinued
0.8261	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7819	Suspended
0.8235	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD3749	Approved
0.821	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD5402	Approved
0.8204	Intermediate Similarity	NPD7473	Discontinued
0.8194	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD6959	Discontinued
0.8144	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6190	Approved
0.8129	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7808	Phase 3
0.8121	Intermediate Similarity	NPD5494	Approved
0.8113	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6801	Discontinued
0.8079	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1613	Approved
0.8063	Intermediate Similarity	NPD1653	Approved
0.8061	Intermediate Similarity	NPD6234	Discontinued
0.8049	Intermediate Similarity	NPD7768	Phase 2
0.8038	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.7987	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1510	Phase 2
0.7987	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6559	Discontinued
0.7964	Intermediate Similarity	NPD7199	Phase 2
0.7962	Intermediate Similarity	NPD4628	Phase 3
0.7947	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7228	Approved
0.7935	Intermediate Similarity	NPD2796	Approved
0.7933	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5401	Approved
0.7871	Intermediate Similarity	NPD3748	Approved
0.787	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD37	Approved
0.7853	Intermediate Similarity	NPD6599	Discontinued
0.7853	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD943	Approved
0.7834	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD4967	Phase 2
0.7831	Intermediate Similarity	NPD4966	Approved
0.7831	Intermediate Similarity	NPD4965	Approved
0.7821	Intermediate Similarity	NPD1551	Phase 2
0.7812	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD9269	Phase 2
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7759	Intermediate Similarity	NPD7685	Pre-registration
0.7736	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1240	Approved
0.7707	Intermediate Similarity	NPD2935	Discontinued
0.7697	Intermediate Similarity	NPD4908	Phase 1
0.7683	Intermediate Similarity	NPD3226	Approved
0.7677	Intermediate Similarity	NPD447	Suspended
0.767	Intermediate Similarity	NPD8313	Approved
0.767	Intermediate Similarity	NPD8312	Approved
0.7647	Intermediate Similarity	NPD3027	Phase 3
0.7633	Intermediate Similarity	NPD919	Approved
0.763	Intermediate Similarity	NPD3751	Discontinued
0.7628	Intermediate Similarity	NPD1607	Approved
0.7605	Intermediate Similarity	NPD8455	Phase 2
0.7597	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6798	Discontinued
0.7569	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD920	Approved
0.756	Intermediate Similarity	NPD5353	Approved
0.7558	Intermediate Similarity	NPD3926	Phase 2
0.7547	Intermediate Similarity	NPD7266	Discontinued
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD9268	Approved
0.75	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD6099	Approved
0.7484	Intermediate Similarity	NPD3764	Approved
0.7468	Intermediate Similarity	NPD6832	Phase 2
0.7458	Intermediate Similarity	NPD7240	Approved
0.7457	Intermediate Similarity	NPD5242	Approved
0.7453	Intermediate Similarity	NPD1243	Approved
0.7452	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5124	Phase 1
0.7442	Intermediate Similarity	NPD8127	Discontinued
0.7436	Intermediate Similarity	NPD6233	Phase 2
0.7435	Intermediate Similarity	NPD8151	Discontinued
0.7434	Intermediate Similarity	NPD3225	Approved
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4308	Phase 3
0.7416	Intermediate Similarity	NPD7549	Discontinued
0.7407	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD9494	Approved
0.7394	Intermediate Similarity	NPD6273	Approved
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.7386	Intermediate Similarity	NPD2797	Approved
0.7372	Intermediate Similarity	NPD3268	Approved
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.736	Intermediate Similarity	NPD7038	Approved
0.736	Intermediate Similarity	NPD7039	Approved
0.7353	Intermediate Similarity	NPD4288	Approved
0.7351	Intermediate Similarity	NPD422	Phase 1
0.7351	Intermediate Similarity	NPD1610	Phase 2
0.7346	Intermediate Similarity	NPD2800	Approved
0.7346	Intermediate Similarity	NPD1652	Phase 2
0.7342	Intermediate Similarity	NPD1933	Approved
0.7342	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD1247	Approved
0.7333	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7312	Intermediate Similarity	NPD2799	Discontinued
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7312	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1608	Approved
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.7278	Intermediate Similarity	NPD6386	Approved
0.7278	Intermediate Similarity	NPD6385	Approved
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7268	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7783	Phase 2
0.7268	Intermediate Similarity	NPD4287	Approved
0.7267	Intermediate Similarity	NPD6971	Discontinued
0.7262	Intermediate Similarity	NPD7458	Discontinued
0.7253	Intermediate Similarity	NPD8150	Discontinued
0.7253	Intermediate Similarity	NPD8434	Phase 2
0.7233	Intermediate Similarity	NPD6355	Discontinued
0.7232	Intermediate Similarity	NPD7177	Discontinued
0.7222	Intermediate Similarity	NPD2344	Approved
0.7212	Intermediate Similarity	NPD7440	Discontinued
0.7205	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7585	Approved
0.72	Intermediate Similarity	NPD1548	Phase 1
0.72	Intermediate Similarity	NPD9545	Approved
0.7196	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7003	Approved
0.7195	Intermediate Similarity	NPD8166	Discontinued
0.719	Intermediate Similarity	NPD9717	Approved
0.7179	Intermediate Similarity	NPD2861	Phase 2
0.7173	Intermediate Similarity	NPD7435	Discontinued
0.717	Intermediate Similarity	NPD4307	Phase 2
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD1296	Phase 2
0.715	Intermediate Similarity	NPD7583	Approved
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7097	Phase 1
0.7124	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6782	Approved
0.7105	Intermediate Similarity	NPD6780	Approved
0.7105	Intermediate Similarity	NPD6776	Approved
0.7105	Intermediate Similarity	NPD6781	Approved
0.7105	Intermediate Similarity	NPD6777	Approved
0.7105	Intermediate Similarity	NPD6779	Approved
0.7105	Intermediate Similarity	NPD6778	Approved
0.7105	Intermediate Similarity	NPD17	Approved
0.7083	Intermediate Similarity	NPD7680	Approved
0.7081	Intermediate Similarity	NPD6651	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