NPASS Compound

Structure

CID169 OpenBabel06191715322D 21 23 0 0 1 0 0 0 0 0999 V2000 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -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 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 1 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 -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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 9 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 15 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 19 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 17 1 6 0 0 0 13 19 1 0 0 0 0 14 21 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	2.438
LogD:	2.451
LogS:	-3.342
# Rotatable Bonds:	4
TPSA:	72.81
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.589
Synthetic Accessibility Score:	3.323
Fsp3:	0.188
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:	-4.903
MDCK Permeability:	1.4355463463289198e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.94
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	90.12303924560547%
Volume Distribution (VD):	0.875
Pgp-substrate:	11.372106552124023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.817
CYP2C19-inhibitor:	0.5
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.246
CYP2C9-substrate:	0.838
CYP2D6-inhibitor:	0.424
CYP2D6-substrate:	0.828
CYP3A4-inhibitor:	0.232
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	9.839
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.35
Drug-inuced Liver Injury (DILI):	0.789
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.283
Carcinogencity:	0.67
Eye Corrosion:	0.003
Eye Irritation:	0.541
Respiratory Toxicity:	0.783

Download Data

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

Natural Product: NPC169

Natural Product ID:	NPC169
*Common Name:**	4-[(2R)-2-Hydroxy-3-Methylbut-3-Enoxy]Furo[3,2-G]Chromen-7-One
IUPAC Name:	4-[(2R)-2-hydroxy-3-methylbut-3-enoxy]furo[3,2-g]chromen-7-one
Synonyms:
Standard InCHIKey:	BVMOMQJYQYBMKL-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-9(2)12(17)8-20-16-10-3-4-15(18)21-14(10)7-13-11(16)5-6-19-13/h3-7,12,17H,1,8H2,2H3/t12-/m0/s1
SMILES:	O=c1ccc2c(o1)cc1c(c2OC[C@@H](C(=C)C)O)cco1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1870203
PubChem CID:	44144315
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens

*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
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	DOI[10.5012/bkcs.2003.24.11.1699]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[12510838]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12568545]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15646793]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191562]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21657081]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27444348]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28093914]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31464439]
NPO15752	Ducrosia anethifolia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6483572]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29747	Selenarctos thibetanus,	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO15752	Ducrosia anethifolia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16027	Niphogeton ternata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12730	Heracleum maximum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16027	Niphogeton ternata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29662	Ursus thibetanus	Species	Ursidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15752	Ducrosia anethifolia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19657	Ursus arctos	Species	Ursidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19657	Ursus arctos	Species	Ursidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16027	Niphogeton ternata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12730	Heracleum maximum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19657	Ursus arctos	Species	Ursidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24758	Angelica dahurica	Species	Apiaceae	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
AC50	1
Others	3
Potency	3

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	2511.9	nM	PMID[557385]
NPT2107	Cell Line	PSN1	Homo sapiens	PC50	>	100.0	uM	PMID[557386]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	PC50	>	100.0	uM	PMID[557386]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	86.6	uM	PMID[557386]
NPT84	Individual Protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Rattus norvegicus	AC50	=	9077.0	nM	PMID[557385]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[557385]
NPT2	Others	Unspecified		Potency	n.a.	501.2	nM	PMID[557385]

☑ 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 NPC169 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	353
0.1-0.2	1579
0.2-0.3	3942
0.3-0.4	9083
0.4-0.5	9641
0.5-0.6	4177
0.6-0.7	5961
0.7-0.8	4909
0.8-0.85	2364
0.85-0.9	575
0.9-0.95	106
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC14822
0.9739	High Similarity	NPC303210
0.9739	High Similarity	NPC95472
0.9739	High Similarity	NPC239270
0.9739	High Similarity	NPC49009
0.9737	High Similarity	NPC269495
0.9404	High Similarity	NPC88445
0.9355	High Similarity	NPC270044
0.9351	High Similarity	NPC278010
0.9351	High Similarity	NPC295608
0.9351	High Similarity	NPC250769
0.9342	High Similarity	NPC191104
0.9342	High Similarity	NPC155882
0.9286	High Similarity	NPC131725
0.9272	High Similarity	NPC304443
0.9272	High Similarity	NPC74539
0.9264	High Similarity	NPC107244
0.9146	High Similarity	NPC325176
0.9141	High Similarity	NPC233956
0.9139	High Similarity	NPC246903
0.9136	High Similarity	NPC51404
0.9103	High Similarity	NPC108937
0.9103	High Similarity	NPC279218
0.9097	High Similarity	NPC263676
0.9085	High Similarity	NPC224165
0.9085	High Similarity	NPC266743
0.908	High Similarity	NPC472584
0.9051	High Similarity	NPC476349
0.9051	High Similarity	NPC476350
0.9045	High Similarity	NPC321372
0.9045	High Similarity	NPC475797
0.9045	High Similarity	NPC474738
0.9045	High Similarity	NPC474609
0.9045	High Similarity	NPC129053
0.9045	High Similarity	NPC78554
0.9045	High Similarity	NPC109967
0.9045	High Similarity	NPC469936
0.9032	High Similarity	NPC474772
0.9032	High Similarity	NPC472423
0.9032	High Similarity	NPC474744
0.9018	High Similarity	NPC120220
0.9018	High Similarity	NPC281835
0.9013	High Similarity	NPC208584
0.9013	High Similarity	NPC297788
0.9007	High Similarity	NPC51146
0.9007	High Similarity	NPC166858
0.9007	High Similarity	NPC313036
0.9006	High Similarity	NPC329215
0.9006	High Similarity	NPC259007
0.9006	High Similarity	NPC204088
0.8974	High Similarity	NPC256141
0.8974	High Similarity	NPC476238
0.8974	High Similarity	NPC31627
0.8974	High Similarity	NPC285623
0.8974	High Similarity	NPC327269
0.897	High Similarity	NPC53917
0.8968	High Similarity	NPC470908
0.8968	High Similarity	NPC472421
0.8954	High Similarity	NPC190572
0.8951	High Similarity	NPC323137
0.8944	High Similarity	NPC15819
0.8938	High Similarity	NPC74854
0.8938	High Similarity	NPC30655
0.8938	High Similarity	NPC45124
0.8924	High Similarity	NPC247677
0.8924	High Similarity	NPC19860
0.8924	High Similarity	NPC160015
0.8917	High Similarity	NPC122365
0.891	High Similarity	NPC116604
0.891	High Similarity	NPC290671
0.891	High Similarity	NPC471675
0.8903	High Similarity	NPC296030
0.8903	High Similarity	NPC226644
0.8903	High Similarity	NPC37226
0.8903	High Similarity	NPC317492
0.8903	High Similarity	NPC39929
0.8896	High Similarity	NPC202494
0.8882	High Similarity	NPC219861
0.8875	High Similarity	NPC260296
0.8875	High Similarity	NPC304839
0.8875	High Similarity	NPC220582
0.8875	High Similarity	NPC243509
0.8875	High Similarity	NPC115432
0.8868	High Similarity	NPC260902
0.8868	High Similarity	NPC296957
0.8854	High Similarity	NPC67654
0.8854	High Similarity	NPC473996
0.8846	High Similarity	NPC180351
0.8846	High Similarity	NPC321387
0.8846	High Similarity	NPC327059
0.8846	High Similarity	NPC474735
0.8846	High Similarity	NPC148423
0.8846	High Similarity	NPC135303
0.8839	High Similarity	NPC168085
0.8834	High Similarity	NPC67450
0.8834	High Similarity	NPC155264
0.8834	High Similarity	NPC193881
0.8834	High Similarity	NPC210460
0.8827	High Similarity	NPC472581
0.8827	High Similarity	NPC179464
0.882	High Similarity	NPC92589
0.882	High Similarity	NPC216092
0.8816	High Similarity	NPC254010
0.8812	High Similarity	NPC33320
0.8812	High Similarity	NPC244750
0.8808	High Similarity	NPC262635
0.8797	High Similarity	NPC7989
0.8797	High Similarity	NPC472583
0.8797	High Similarity	NPC1477
0.8797	High Similarity	NPC213608
0.8797	High Similarity	NPC223701
0.8797	High Similarity	NPC469405
0.879	High Similarity	NPC98028
0.879	High Similarity	NPC471676
0.879	High Similarity	NPC472422
0.879	High Similarity	NPC156244
0.879	High Similarity	NPC244577
0.879	High Similarity	NPC472636
0.879	High Similarity	NPC472580
0.879	High Similarity	NPC472420
0.879	High Similarity	NPC170169
0.879	High Similarity	NPC263384
0.878	High Similarity	NPC320789
0.878	High Similarity	NPC476459
0.8774	High Similarity	NPC130581
0.8774	High Similarity	NPC198427
0.8774	High Similarity	NPC14875
0.8774	High Similarity	NPC12148
0.8773	High Similarity	NPC136641
0.8773	High Similarity	NPC38914
0.8773	High Similarity	NPC173149
0.8773	High Similarity	NPC179015
0.8766	High Similarity	NPC316535
0.8765	High Similarity	NPC193998
0.8765	High Similarity	NPC78612
0.8765	High Similarity	NPC234536
0.8758	High Similarity	NPC294432
0.875	High Similarity	NPC470856
0.875	High Similarity	NPC65504
0.8742	High Similarity	NPC198490
0.8742	High Similarity	NPC473241
0.8742	High Similarity	NPC477530
0.8742	High Similarity	NPC469934
0.8742	High Similarity	NPC470681
0.8742	High Similarity	NPC474542
0.8734	High Similarity	NPC150123
0.8734	High Similarity	NPC38361
0.8734	High Similarity	NPC130015
0.8734	High Similarity	NPC10807
0.8734	High Similarity	NPC171651
0.8734	High Similarity	NPC243171
0.8734	High Similarity	NPC244583
0.8734	High Similarity	NPC161881
0.8734	High Similarity	NPC56232
0.8734	High Similarity	NPC253872
0.8734	High Similarity	NPC477957
0.8734	High Similarity	NPC35567
0.8734	High Similarity	NPC5871
0.8726	High Similarity	NPC78335
0.8726	High Similarity	NPC230713
0.872	High Similarity	NPC53640
0.8718	High Similarity	NPC306788
0.8718	High Similarity	NPC10097
0.8718	High Similarity	NPC135325
0.8712	High Similarity	NPC155640
0.871	High Similarity	NPC210826
0.871	High Similarity	NPC51641
0.871	High Similarity	NPC300267
0.871	High Similarity	NPC316769
0.871	High Similarity	NPC474302
0.8704	High Similarity	NPC97812
0.8701	High Similarity	NPC302181
0.8701	High Similarity	NPC96216
0.8701	High Similarity	NPC184738
0.8701	High Similarity	NPC225884
0.8701	High Similarity	NPC474939
0.8701	High Similarity	NPC470909
0.8701	High Similarity	NPC33653
0.8696	High Similarity	NPC40583
0.8693	High Similarity	NPC171870
0.8688	High Similarity	NPC471787
0.8688	High Similarity	NPC470625
0.8684	High Similarity	NPC137009
0.8684	High Similarity	NPC471697
0.8684	High Similarity	NPC37206
0.8679	High Similarity	NPC41719
0.8679	High Similarity	NPC293286
0.8679	High Similarity	NPC183874
0.8679	High Similarity	NPC472462
0.8675	High Similarity	NPC131866
0.8675	High Similarity	NPC144288
0.8671	High Similarity	NPC262039
0.8671	High Similarity	NPC289774
0.8671	High Similarity	NPC278476
0.8671	High Similarity	NPC319910
0.8671	High Similarity	NPC477897
0.8671	High Similarity	NPC471677
0.8671	High Similarity	NPC472407
0.8671	High Similarity	NPC209846
0.8671	High Similarity	NPC262038

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 NPC169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	881
0.2-0.3	1819
0.3-0.4	2648
0.4-0.5	1933
0.5-0.6	1040
0.6-0.7	337
0.7-0.8	108
0.8-0.85	32
0.85-0.9	12
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9272	High Similarity	NPD920	Approved
0.9139	High Similarity	NPD642	Clinical (unspecified phase)
0.9007	High Similarity	NPD643	Clinical (unspecified phase)
0.8812	High Similarity	NPD919	Approved
0.8808	High Similarity	NPD1243	Approved
0.8734	High Similarity	NPD6801	Discontinued
0.8683	High Similarity	NPD6559	Discontinued
0.8679	High Similarity	NPD7096	Clinical (unspecified phase)
0.8634	High Similarity	NPD7075	Discontinued
0.8608	High Similarity	NPD4380	Phase 2
0.8476	Intermediate Similarity	NPD1247	Approved
0.8462	Intermediate Similarity	NPD6799	Approved
0.8408	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8272	Intermediate Similarity	NPD1934	Approved
0.8261	Intermediate Similarity	NPD6599	Discontinued
0.8258	Intermediate Similarity	NPD1549	Phase 2
0.8247	Intermediate Similarity	NPD2796	Approved
0.8232	Intermediate Similarity	NPD3882	Suspended
0.8221	Intermediate Similarity	NPD7819	Suspended
0.8194	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD5403	Approved
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8176	Intermediate Similarity	NPD5401	Approved
0.8176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3817	Phase 2
0.8171	Intermediate Similarity	NPD5402	Approved
0.8129	Intermediate Similarity	NPD1551	Phase 2
0.811	Intermediate Similarity	NPD2801	Approved
0.8089	Intermediate Similarity	NPD2800	Approved
0.8084	Intermediate Similarity	NPD5494	Approved
0.8077	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD5844	Phase 1
0.8063	Intermediate Similarity	NPD2532	Approved
0.8063	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD2534	Approved
0.8063	Intermediate Similarity	NPD2533	Approved
0.8039	Intermediate Similarity	NPD1240	Approved
0.8038	Intermediate Similarity	NPD4628	Phase 3
0.8038	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.8012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1511	Approved
0.7975	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2344	Approved
0.7952	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1607	Approved
0.7925	Intermediate Similarity	NPD3750	Approved
0.7911	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD8434	Phase 2
0.7908	Intermediate Similarity	NPD2313	Discontinued
0.7901	Intermediate Similarity	NPD1512	Approved
0.7895	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6166	Phase 2
0.7886	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6232	Discontinued
0.7861	Intermediate Similarity	NPD7054	Approved
0.7849	Intermediate Similarity	NPD7473	Discontinued
0.7834	Intermediate Similarity	NPD2799	Discontinued
0.7816	Intermediate Similarity	NPD7472	Approved
0.7816	Intermediate Similarity	NPD7074	Phase 3
0.7792	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7771	Intermediate Similarity	NPD6797	Phase 2
0.7771	Intermediate Similarity	NPD5953	Discontinued
0.7764	Intermediate Similarity	NPD2309	Approved
0.7759	Intermediate Similarity	NPD7286	Phase 2
0.7758	Intermediate Similarity	NPD3226	Approved
0.7733	Intermediate Similarity	NPD3926	Phase 2
0.7727	Intermediate Similarity	NPD7251	Discontinued
0.7722	Intermediate Similarity	NPD3748	Approved
0.7719	Intermediate Similarity	NPD6959	Discontinued
0.7684	Intermediate Similarity	NPD7808	Phase 3
0.7679	Intermediate Similarity	NPD1465	Phase 2
0.767	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD447	Suspended
0.7616	Intermediate Similarity	NPD9717	Approved
0.761	Intermediate Similarity	NPD7033	Discontinued
0.76	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1203	Approved
0.7568	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6832	Phase 2
0.7532	Intermediate Similarity	NPD5124	Phase 1
0.7532	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7471	Intermediate Similarity	NPD5710	Approved
0.7471	Intermediate Similarity	NPD5711	Approved
0.7446	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD422	Phase 1
0.7432	Intermediate Similarity	NPD4287	Approved
0.7425	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1652	Phase 2
0.7421	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD3751	Discontinued
0.7391	Intermediate Similarity	NPD4308	Phase 3
0.7375	Intermediate Similarity	NPD6651	Approved
0.7371	Intermediate Similarity	NPD7229	Phase 3
0.7371	Intermediate Similarity	NPD6808	Phase 2
0.7368	Intermediate Similarity	NPD5761	Phase 2
0.7368	Intermediate Similarity	NPD5760	Phase 2
0.7362	Intermediate Similarity	NPD2424	Discontinued
0.7358	Intermediate Similarity	NPD943	Approved
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8312	Approved
0.7348	Intermediate Similarity	NPD8313	Approved
0.7342	Intermediate Similarity	NPD3268	Approved
0.7337	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7199	Phase 2
0.7312	Intermediate Similarity	NPD6355	Discontinued
0.731	Intermediate Similarity	NPD37	Approved
0.7308	Intermediate Similarity	NPD1019	Discontinued
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6002	Phase 3
0.7301	Intermediate Similarity	NPD6004	Phase 3
0.7301	Intermediate Similarity	NPD6005	Phase 3
0.7301	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4965	Approved
0.7283	Intermediate Similarity	NPD4967	Phase 2
0.7283	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7244	Intermediate Similarity	NPD2797	Approved
0.7235	Intermediate Similarity	NPD7458	Discontinued
0.7235	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1296	Phase 2
0.7233	Intermediate Similarity	NPD411	Approved
0.7233	Intermediate Similarity	NPD6798	Discontinued
0.7225	Intermediate Similarity	NPD2296	Approved
0.7222	Intermediate Similarity	NPD1729	Discontinued
0.7216	Intermediate Similarity	NPD7584	Approved
0.7208	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1933	Approved
0.72	Intermediate Similarity	NPD6234	Discontinued
0.7195	Intermediate Similarity	NPD1471	Phase 3
0.7191	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4360	Phase 2
0.7181	Intermediate Similarity	NPD4363	Phase 3
0.7179	Intermediate Similarity	NPD3225	Approved
0.7178	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1653	Approved
0.7175	Intermediate Similarity	NPD3787	Discontinued
0.7171	Intermediate Similarity	NPD9545	Approved
0.7169	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7143	Intermediate Similarity	NPD8151	Discontinued
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3266	Approved
0.7134	Intermediate Similarity	NPD3267	Approved
0.7128	Intermediate Similarity	NPD7583	Approved
0.7126	Intermediate Similarity	NPD2354	Approved
0.7126	Intermediate Similarity	NPD4288	Approved
0.7125	Intermediate Similarity	NPD3764	Approved
0.711	Intermediate Similarity	NPD6280	Approved
0.711	Intermediate Similarity	NPD6279	Approved
0.7108	Intermediate Similarity	NPD2654	Approved
0.7095	Intermediate Similarity	NPD2403	Approved
0.7095	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7585	Approved
0.7089	Intermediate Similarity	NPD2798	Approved
0.7089	Intermediate Similarity	NPD5647	Approved
0.7081	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6233	Phase 2
0.7071	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7783	Phase 2
0.7062	Intermediate Similarity	NPD7435	Discontinued
0.7059	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD5049	Phase 3
0.7051	Intermediate Similarity	NPD1608	Approved
0.7049	Intermediate Similarity	NPD6764	Approved
0.7049	Intermediate Similarity	NPD6765	Approved
0.7044	Intermediate Similarity	NPD9494	Approved
0.7043	Intermediate Similarity	NPD8150	Discontinued
0.7039	Intermediate Similarity	NPD9493	Approved
0.7025	Intermediate Similarity	NPD1164	Approved
0.7024	Intermediate Similarity	NPD6190	Approved
0.7024	Intermediate Similarity	NPD3887	Approved
0.7019	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7228	Approved
0.7	Intermediate Similarity	NPD4661	Approved
0.7	Intermediate Similarity	NPD4662	Approved
0.6995	Remote Similarity	NPD6777	Approved
0.6995	Remote Similarity	NPD6779	Approved
0.6995	Remote Similarity	NPD6778	Approved
0.6995	Remote Similarity	NPD6782	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