NPASS Compound

Structure

CID112237 OpenBabel06191715462D 21 23 0 0 1 0 0 0 0 0999 V2000 1.9400 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4041 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4041 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 4.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5380 4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2701 2.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 5.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 5.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 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 5 1 0 0 0 0 1 10 1 0 0 0 0 2 6 2 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 9 21 1 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 14 2 0 0 0 0 13 18 1 6 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	287.755
LogP:	2.16
LogD:	2.806
LogS:	-3.024
# Rotatable Bonds:	4
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.805
Synthetic Accessibility Score:	2.695
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.838
MDCK Permeability:	1.7304904758930206e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.809
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	96.1915054321289%
Volume Distribution (VD):	0.918
Pgp-substrate:	4.365854263305664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.42
CYP2C19-inhibitor:	0.939
CYP2C19-substrate:	0.136
CYP2C9-inhibitor:	0.671
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.974
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.319

ADMET: Excretion

Clearance (CL):	18.045
Half-life (T1/2):	0.8

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.411
Rat Oral Acute Toxicity:	0.295
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.921
Carcinogencity:	0.867
Eye Corrosion:	0.006
Eye Irritation:	0.614
Respiratory Toxicity:	0.623

Download Data

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

Natural Product: NPC112237

Natural Product ID:	NPC112237
*Common Name:**	4-[(1S)-3-(1,3-Benzodioxol-5-Yl)-1-Hydroxypropyl]Benzene-1,3-Diol
IUPAC Name:	4-[(1S)-3-(1,3-benzodioxol-5-yl)-1-hydroxypropyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	CWAZIFFOONOPTR-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C16H16O5/c17-11-3-4-12(14(19)8-11)13(18)5-1-10-2-6-15-16(7-10)21-9-20-15/h2-4,6-8,13,17-19H,1,5,9H2/t13-/m0/s1
SMILES:	Oc1ccc(c(c1)O)[C@H](CCc1ccc2c(c1)OCO2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1909923
PubChem CID:	57403255
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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	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.		Database[FooDB]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	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]
NPO17811	Cephalonoplos segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5746	Pancratium trianthum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7393	Esenbeckia nesiotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5334	Rhodotypos scandens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19928	Lachnoanaerobaculum saburreum	Species	Lachnospiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2665	Andinobates fulguritus	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7237	Xanthostemon oppositifolius	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28409	Lens phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8532	Helipterum tenellum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6113	Piper pedicellosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5162	Comaster multifida	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4539	Ipomoea cristulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO490	Lophozonia menziesii	Species	0thofagaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[464367]

☑ 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 NPC112237 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	406
0.1-0.2	1669
0.2-0.3	4945
0.3-0.4	12704
0.4-0.5	5193
0.5-0.6	4421
0.6-0.7	7902
0.7-0.8	4082
0.8-0.85	983
0.85-0.9	353
0.9-0.95	35
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC184814
0.9535	High Similarity	NPC58585
0.9453	High Similarity	NPC63574
0.9385	High Similarity	NPC471390
0.9385	High Similarity	NPC471391
0.9333	High Similarity	NPC474808
0.9323	High Similarity	NPC292487
0.9248	High Similarity	NPC474039
0.9237	High Similarity	NPC196937
0.9225	High Similarity	NPC212015
0.9173	High Similarity	NPC25695
0.9173	High Similarity	NPC172818
0.9173	High Similarity	NPC197166
0.9118	High Similarity	NPC36531
0.9118	High Similarity	NPC229172
0.9118	High Similarity	NPC41782
0.9118	High Similarity	NPC103637
0.9118	High Similarity	NPC230538
0.9111	High Similarity	NPC284464
0.9077	High Similarity	NPC470633
0.9077	High Similarity	NPC469963
0.9077	High Similarity	NPC228769
0.9077	High Similarity	NPC469951
0.907	High Similarity	NPC242032
0.9062	High Similarity	NPC105925
0.9058	High Similarity	NPC180953
0.9058	High Similarity	NPC166506
0.9058	High Similarity	NPC189239
0.9058	High Similarity	NPC110763
0.9058	High Similarity	NPC197352
0.9051	High Similarity	NPC324962
0.9051	High Similarity	NPC81638
0.9037	High Similarity	NPC30951
0.9037	High Similarity	NPC6369
0.9037	High Similarity	NPC9068
0.9015	High Similarity	NPC106739
0.9	High Similarity	NPC470213
0.9	High Similarity	NPC98631
0.9	High Similarity	NPC186843
0.9	High Similarity	NPC206615
0.8992	High Similarity	NPC473960
0.8986	High Similarity	NPC121661
0.8986	High Similarity	NPC239254
0.8986	High Similarity	NPC73467
0.8986	High Similarity	NPC172171
0.8971	High Similarity	NPC177868
0.8963	High Similarity	NPC185908
0.8955	High Similarity	NPC184938
0.8955	High Similarity	NPC150534
0.8955	High Similarity	NPC101624
0.8947	High Similarity	NPC475840
0.8931	High Similarity	NPC170844
0.8931	High Similarity	NPC476968
0.8923	High Similarity	NPC124452
0.8923	High Similarity	NPC324112
0.8923	High Similarity	NPC159968
0.8923	High Similarity	NPC282000
0.8923	High Similarity	NPC236791
0.8923	High Similarity	NPC74817
0.8923	High Similarity	NPC169474
0.8923	High Similarity	NPC293054
0.8923	High Similarity	NPC82679
0.8923	High Similarity	NPC246620
0.8921	High Similarity	NPC178014
0.8921	High Similarity	NPC11422
0.8921	High Similarity	NPC474749
0.8921	High Similarity	NPC42716
0.8921	High Similarity	NPC475868
0.8921	High Similarity	NPC475096
0.8913	High Similarity	NPC298317
0.8913	High Similarity	NPC255566
0.8906	High Similarity	NPC233526
0.8906	High Similarity	NPC282496
0.8905	High Similarity	NPC469661
0.8881	High Similarity	NPC287745
0.8872	High Similarity	NPC471505
0.8872	High Similarity	NPC259742
0.8872	High Similarity	NPC104077
0.8872	High Similarity	NPC219671
0.8872	High Similarity	NPC147616
0.8857	High Similarity	NPC190714
0.8857	High Similarity	NPC125755
0.8857	High Similarity	NPC252286
0.8857	High Similarity	NPC99515
0.8857	High Similarity	NPC154971
0.8849	High Similarity	NPC187774
0.8849	High Similarity	NPC472713
0.8849	High Similarity	NPC76176
0.8849	High Similarity	NPC118385
0.8849	High Similarity	NPC168579
0.8849	High Similarity	NPC473046
0.8849	High Similarity	NPC469313
0.8849	High Similarity	NPC472712
0.8849	High Similarity	NPC138227
0.8846	High Similarity	NPC78974
0.8846	High Similarity	NPC223136
0.8846	High Similarity	NPC28730
0.8846	High Similarity	NPC103823
0.8846	High Similarity	NPC223953
0.8846	High Similarity	NPC214406
0.8846	High Similarity	NPC18924
0.8846	High Similarity	NPC44748
0.8841	High Similarity	NPC133934
0.8841	High Similarity	NPC184641
0.8841	High Similarity	NPC184684
0.8841	High Similarity	NPC475084
0.8841	High Similarity	NPC189115
0.8841	High Similarity	NPC191231
0.8832	High Similarity	NPC46591
0.8824	High Similarity	NPC477938
0.8824	High Similarity	NPC283949
0.8815	High Similarity	NPC236522
0.8815	High Similarity	NPC61946
0.8815	High Similarity	NPC18576
0.8815	High Similarity	NPC256262
0.8806	High Similarity	NPC158331
0.8806	High Similarity	NPC266848
0.8806	High Similarity	NPC136750
0.8797	High Similarity	NPC474017
0.8797	High Similarity	NPC192255
0.8794	High Similarity	NPC39657
0.8794	High Similarity	NPC227902
0.8786	High Similarity	NPC161700
0.8786	High Similarity	NPC307466
0.8786	High Similarity	NPC277867
0.8779	High Similarity	NPC252131
0.8777	High Similarity	NPC12728
0.8777	High Similarity	NPC37793
0.8777	High Similarity	NPC185071
0.8777	High Similarity	NPC252169
0.8769	High Similarity	NPC203133
0.8769	High Similarity	NPC17943
0.8769	High Similarity	NPC82483
0.8769	High Similarity	NPC265483
0.8769	High Similarity	NPC251855
0.8769	High Similarity	NPC299584
0.8769	High Similarity	NPC116907
0.8769	High Similarity	NPC472093
0.8769	High Similarity	NPC298757
0.8769	High Similarity	NPC234400
0.8769	High Similarity	NPC60885
0.8769	High Similarity	NPC233410
0.8769	High Similarity	NPC117214
0.8769	High Similarity	NPC208950
0.8769	High Similarity	NPC193544
0.8769	High Similarity	NPC475169
0.8769	High Similarity	NPC221077
0.8769	High Similarity	NPC57490
0.8768	High Similarity	NPC263261
0.8768	High Similarity	NPC87725
0.876	High Similarity	NPC197757
0.876	High Similarity	NPC121115
0.876	High Similarity	NPC228922
0.876	High Similarity	NPC249788
0.8759	High Similarity	NPC290714
0.8759	High Similarity	NPC201404
0.8759	High Similarity	NPC53722
0.875	High Similarity	NPC75713
0.875	High Similarity	NPC269091
0.875	High Similarity	NPC472334
0.875	High Similarity	NPC306441
0.875	High Similarity	NPC472336
0.875	High Similarity	NPC302701
0.875	High Similarity	NPC16435
0.8741	High Similarity	NPC472709
0.8741	High Similarity	NPC47181
0.8741	High Similarity	NPC107478
0.8741	High Similarity	NPC244983
0.8741	High Similarity	NPC472710
0.8741	High Similarity	NPC326095
0.874	High Similarity	NPC474565
0.8732	High Similarity	NPC325720
0.8732	High Similarity	NPC175976
0.8732	High Similarity	NPC316676
0.8732	High Similarity	NPC166584
0.8732	High Similarity	NPC71726
0.8732	High Similarity	NPC270751
0.8732	High Similarity	NPC301961
0.8731	High Similarity	NPC204215
0.8731	High Similarity	NPC201587
0.8731	High Similarity	NPC65183
0.8731	High Similarity	NPC72046
0.8731	High Similarity	NPC175067
0.8731	High Similarity	NPC253105
0.8731	High Similarity	NPC7744
0.8731	High Similarity	NPC97316
0.8731	High Similarity	NPC261812
0.8731	High Similarity	NPC470752
0.8723	High Similarity	NPC212890
0.8723	High Similarity	NPC226540
0.8723	High Similarity	NPC162193
0.8723	High Similarity	NPC33832
0.8722	High Similarity	NPC299221
0.8722	High Similarity	NPC472338
0.8722	High Similarity	NPC51840
0.8722	High Similarity	NPC192687
0.8722	High Similarity	NPC311680
0.8722	High Similarity	NPC234488
0.8722	High Similarity	NPC224157
0.8722	High Similarity	NPC126836

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 NPC112237 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	898
0.2-0.3	1913
0.3-0.4	2778
0.4-0.5	1581
0.5-0.6	928
0.6-0.7	602
0.7-0.8	91
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8931	High Similarity	NPD3027	Phase 3
0.8593	High Similarity	NPD1612	Clinical (unspecified phase)
0.8593	High Similarity	NPD1613	Approved
0.8372	Intermediate Similarity	NPD1357	Approved
0.8311	Intermediate Similarity	NPD37	Approved
0.8296	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD4967	Phase 2
0.8146	Intermediate Similarity	NPD4965	Approved
0.8146	Intermediate Similarity	NPD4966	Approved
0.8088	Intermediate Similarity	NPD3018	Phase 2
0.8045	Intermediate Similarity	NPD3705	Approved
0.8041	Intermediate Similarity	NPD1653	Approved
0.8039	Intermediate Similarity	NPD6234	Discontinued
0.8025	Intermediate Similarity	NPD3818	Discontinued
0.7935	Intermediate Similarity	NPD7199	Phase 2
0.7926	Intermediate Similarity	NPD2982	Phase 2
0.7926	Intermediate Similarity	NPD2983	Phase 2
0.791	Intermediate Similarity	NPD1610	Phase 2
0.791	Intermediate Similarity	NPD1091	Approved
0.7907	Intermediate Similarity	NPD5283	Phase 1
0.7899	Intermediate Similarity	NPD4908	Phase 1
0.7879	Intermediate Similarity	NPD1548	Phase 1
0.7852	Intermediate Similarity	NPD2981	Phase 2
0.7799	Intermediate Similarity	NPD7228	Approved
0.7786	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD228	Approved
0.7742	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7074	Phase 3
0.7698	Intermediate Similarity	NPD2861	Phase 2
0.7662	Intermediate Similarity	NPD2978	Approved
0.7662	Intermediate Similarity	NPD2977	Approved
0.764	Intermediate Similarity	NPD7054	Approved
0.7619	Intermediate Similarity	NPD6674	Discontinued
0.7603	Intermediate Similarity	NPD7266	Discontinued
0.7597	Intermediate Similarity	NPD1934	Approved
0.7593	Intermediate Similarity	NPD7472	Approved
0.7564	Intermediate Similarity	NPD3882	Suspended
0.7552	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3620	Phase 2
0.7536	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3060	Approved
0.75	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3540	Phase 1
0.7465	Intermediate Similarity	NPD4625	Phase 3
0.7455	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7808	Phase 3
0.7452	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6797	Phase 2
0.7436	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4060	Phase 1
0.7415	Intermediate Similarity	NPD3539	Phase 1
0.7413	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4749	Approved
0.7394	Intermediate Similarity	NPD7251	Discontinued
0.7394	Intermediate Similarity	NPD6559	Discontinued
0.7394	Intermediate Similarity	NPD7240	Approved
0.7383	Intermediate Similarity	NPD4237	Approved
0.7383	Intermediate Similarity	NPD4236	Phase 3
0.7383	Intermediate Similarity	NPD5177	Phase 3
0.7381	Intermediate Similarity	NPD1242	Phase 1
0.7351	Intermediate Similarity	NPD5058	Phase 3
0.7346	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6166	Phase 2
0.7346	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3022	Approved
0.7328	Intermediate Similarity	NPD3021	Approved
0.7325	Intermediate Similarity	NPD2801	Approved
0.7323	Intermediate Similarity	NPD940	Approved
0.7323	Intermediate Similarity	NPD846	Approved
0.7303	Intermediate Similarity	NPD4357	Discontinued
0.729	Intermediate Similarity	NPD4005	Discontinued
0.7285	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5536	Phase 2
0.7278	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD422	Phase 1
0.7252	Intermediate Similarity	NPD2684	Approved
0.7244	Intermediate Similarity	NPD4380	Phase 2
0.7237	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1510	Phase 2
0.723	Intermediate Similarity	NPD5588	Approved
0.7222	Intermediate Similarity	NPD6232	Discontinued
0.7219	Intermediate Similarity	NPD3892	Phase 2
0.7212	Intermediate Similarity	NPD5844	Phase 1
0.7197	Intermediate Similarity	NPD4750	Phase 3
0.7192	Intermediate Similarity	NPD2238	Phase 2
0.719	Intermediate Similarity	NPD1511	Approved
0.7179	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD290	Approved
0.717	Intermediate Similarity	NPD3817	Phase 2
0.7164	Intermediate Similarity	NPD7843	Approved
0.716	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4678	Approved
0.7134	Intermediate Similarity	NPD4675	Approved
0.7133	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5762	Approved
0.7133	Intermediate Similarity	NPD5763	Approved
0.7133	Intermediate Similarity	NPD1375	Discontinued
0.7132	Intermediate Similarity	NPD6671	Approved
0.7132	Intermediate Similarity	NPD7157	Approved
0.7124	Intermediate Similarity	NPD7124	Phase 2
0.7108	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4110	Phase 3
0.7105	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5494	Approved
0.7097	Intermediate Similarity	NPD1512	Approved
0.7091	Intermediate Similarity	NPD7473	Discontinued
0.7086	Intermediate Similarity	NPD1549	Phase 2
0.7078	Intermediate Similarity	NPD7213	Phase 3
0.7078	Intermediate Similarity	NPD7212	Phase 2
0.7075	Intermediate Similarity	NPD1558	Phase 1
0.7075	Intermediate Similarity	NPD1240	Approved
0.7067	Intermediate Similarity	NPD2935	Discontinued
0.7063	Intermediate Similarity	NPD2563	Approved
0.7063	Intermediate Similarity	NPD2560	Approved
0.7055	Intermediate Similarity	NPD6798	Discontinued
0.7047	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4536	Approved
0.7047	Intermediate Similarity	NPD4538	Approved
0.7039	Intermediate Similarity	NPD1652	Phase 2
0.7032	Intermediate Similarity	NPD7447	Phase 1
0.7032	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7028	Phase 2
0.7024	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6584	Phase 3
0.7012	Intermediate Similarity	NPD3787	Discontinued
0.7007	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD709	Approved
0.7	Intermediate Similarity	NPD6516	Phase 2
0.7	Intermediate Similarity	NPD5126	Approved
0.7	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD4108	Discontinued
0.7	Intermediate Similarity	NPD8455	Phase 2
0.7	Intermediate Similarity	NPD5960	Phase 3
0.7	Intermediate Similarity	NPD5846	Approved
0.7	Intermediate Similarity	NPD5125	Phase 3
0.6993	Remote Similarity	NPD8651	Approved
0.6993	Remote Similarity	NPD2922	Phase 1
0.6993	Remote Similarity	NPD6331	Phase 2
0.6993	Remote Similarity	NPD3750	Approved
0.6987	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1607	Approved
0.6975	Remote Similarity	NPD7075	Discontinued
0.6975	Remote Similarity	NPD4055	Discovery
0.697	Remote Similarity	NPD968	Approved
0.6966	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD943	Approved
0.6948	Remote Similarity	NPD2219	Phase 1
0.6948	Remote Similarity	NPD6190	Approved
0.6948	Remote Similarity	NPD5241	Discontinued
0.6939	Remote Similarity	NPD5109	Approved
0.6939	Remote Similarity	NPD5111	Phase 2
0.6939	Remote Similarity	NPD5110	Phase 2
0.6937	Remote Similarity	NPD3384	Approved
0.6937	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3382	Approved
0.6937	Remote Similarity	NPD3383	Approved
0.6933	Remote Similarity	NPD6111	Discontinued
0.6929	Remote Similarity	NPD2860	Approved
0.6929	Remote Similarity	NPD2859	Approved
0.6928	Remote Similarity	NPD4162	Approved
0.6923	Remote Similarity	NPD3685	Discontinued
0.6923	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3657	Discovery
0.6913	Remote Similarity	NPD5735	Approved
0.6906	Remote Similarity	NPD7680	Approved
0.6899	Remote Similarity	NPD3020	Approved
0.6894	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1465	Phase 2
0.6892	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2674	Phase 3
0.6887	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4628	Phase 3
0.6882	Remote Similarity	NPD7685	Pre-registration
0.6871	Remote Similarity	NPD7095	Approved
0.6871	Remote Similarity	NPD5604	Discontinued
0.6867	Remote Similarity	NPD2492	Phase 1
0.6867	Remote Similarity	NPD4097	Suspended
0.6863	Remote Similarity	NPD2424	Discontinued
0.6863	Remote Similarity	NPD970	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