NPASS Compound

Structure

NPC88243 OpenBabel07101718302D 29 31 0 0 1 0 0 0 0 0999 V2000 1.7075 -4.6946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4844 -3.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4531 -1.8077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4219 -1.8077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4531 -0.1298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5240 -2.1381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9688 -0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9063 -0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4219 -0.1298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2732 -3.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 -1.4531 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6779 2.9062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8750 -0.9687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9062 0.7092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3558 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3375 -3.3246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 -1.4531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0560 -1.8238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9583 -3.7589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9688 -2.6467 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 27 1 0 0 0 0 2 28 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 16 2 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 29 1 0 0 0 0 15 24 2 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 25 2 0 0 0 0 18 19 1 1 0 0 0 18 26 1 0 0 0 0 19 28 1 6 0 0 0 19 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.09
Volume:	378.321
LogP:	1.768
LogD:	1.404
LogS:	-2.642
# Rotatable Bonds:	5
TPSA:	162.98
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	3.878
Fsp3:	0.263
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:	-6.086
MDCK Permeability:	5.640294148179237e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.794
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	83.30896759033203%
Volume Distribution (VD):	0.859
Pgp-substrate:	8.412175178527832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.193
CYP1A2-substrate:	0.698
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.24
CYP2C9-substrate:	0.548
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.391

ADMET: Excretion

Clearance (CL):	9.509
Half-life (T1/2):	0.945

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.842
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.064
Skin Sensitization:	0.493
Carcinogencity:	0.09
Eye Corrosion:	0.003
Eye Irritation:	0.173
Respiratory Toxicity:	0.075

Download Data

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

Natural Product: NPC88243

Natural Product ID:	NPC88243
*Common Name:**	Erigeroflavanone
IUPAC Name:	methyl 2-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2-methoxy-4-oxochromen-3-yl]acetate
Synonyms:	erigeroflavanone
Standard InCHIKey:	ZPKRBBYQFOQJRL-RBUKOAKNSA-N
Standard InCHI:	InChI=1S/C19H18O10/c1-27-15(24)8-18(26)17(25)16-13(23)6-10(20)7-14(16)29-19(18,28-2)9-3-4-11(21)12(22)5-9/h3-7,20-23,26H,8H2,1-2H3/t18-,19+/m0/s1
SMILES:	COC(=O)C[C@]1(O)C(=O)c2c(O)cc(cc2O[C@]1(OC)c1ccc(c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465526
PubChem CID:	24850296
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002587] 2-O-methylated flavonoids

*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
NPO4380	Erigeron annuus	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[18298080]
NPO4380	Erigeron annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4380	Erigeron annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4380	Erigeron annuus	Species	Asteraceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	46900.0	nM	PMID[522756]

☑ 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 NPC88243 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	392
0.1-0.2	1773
0.2-0.3	4565
0.3-0.4	9485
0.4-0.5	8151
0.5-0.6	3767
0.6-0.7	4863
0.7-0.8	5574
0.8-0.85	2810
0.85-0.9	1272
0.9-0.95	44
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.943	High Similarity	NPC112418
0.9371	High Similarity	NPC471745
0.9367	High Similarity	NPC471744
0.9325	High Similarity	NPC175107
0.9325	High Similarity	NPC190003
0.9268	High Similarity	NPC4390
0.9264	High Similarity	NPC20505
0.9264	High Similarity	NPC116864
0.9264	High Similarity	NPC244776
0.9264	High Similarity	NPC235260
0.9264	High Similarity	NPC155763
0.9259	High Similarity	NPC116745
0.925	High Similarity	NPC300537
0.925	High Similarity	NPC127782
0.9241	High Similarity	NPC67876
0.9212	High Similarity	NPC108202
0.9212	High Similarity	NPC477848
0.9207	High Similarity	NPC153755
0.9202	High Similarity	NPC270578
0.9202	High Similarity	NPC138927
0.9202	High Similarity	NPC52382
0.9198	High Similarity	NPC113093
0.9182	High Similarity	NPC55738
0.9182	High Similarity	NPC152904
0.9177	High Similarity	NPC471500
0.9177	High Similarity	NPC474638
0.9172	High Similarity	NPC141212
0.9157	High Similarity	NPC211532
0.9157	High Similarity	NPC472384
0.9157	High Similarity	NPC472385
0.9157	High Similarity	NPC198324
0.9157	High Similarity	NPC472382
0.9157	High Similarity	NPC472380
0.9157	High Similarity	NPC268533
0.9157	High Similarity	NPC233994
0.9146	High Similarity	NPC212748
0.9141	High Similarity	NPC317489
0.9141	High Similarity	NPC127546
0.9141	High Similarity	NPC173637
0.9141	High Similarity	NPC223424
0.9141	High Similarity	NPC92565
0.9141	High Similarity	NPC84362
0.9141	High Similarity	NPC76482
0.9141	High Similarity	NPC52550
0.9141	High Similarity	NPC160156
0.9136	High Similarity	NPC277205
0.9136	High Similarity	NPC165720
0.9125	High Similarity	NPC470183
0.9125	High Similarity	NPC130955
0.9119	High Similarity	NPC227192
0.9119	High Similarity	NPC75215
0.9119	High Similarity	NPC93376
0.9119	High Similarity	NPC471515
0.9119	High Similarity	NPC224137
0.9119	High Similarity	NPC471479
0.9119	High Similarity	NPC189179
0.9102	High Similarity	NPC35167
0.9096	High Similarity	NPC43211
0.9096	High Similarity	NPC49344
0.9096	High Similarity	NPC210094
0.9096	High Similarity	NPC135277
0.9096	High Similarity	NPC101191
0.9096	High Similarity	NPC253685
0.9096	High Similarity	NPC115760
0.9096	High Similarity	NPC264735
0.9096	High Similarity	NPC237435
0.9091	High Similarity	NPC476405
0.9091	High Similarity	NPC472386
0.9091	High Similarity	NPC117260
0.9091	High Similarity	NPC211594
0.9091	High Similarity	NPC254540
0.9091	High Similarity	NPC172807
0.9091	High Similarity	NPC245452
0.9085	High Similarity	NPC476771
0.9085	High Similarity	NPC120099
0.9085	High Similarity	NPC223747
0.9085	High Similarity	NPC229687
0.9085	High Similarity	NPC203050
0.9085	High Similarity	NPC219904
0.9085	High Similarity	NPC225434
0.908	High Similarity	NPC73855
0.908	High Similarity	NPC145038
0.908	High Similarity	NPC277174
0.908	High Similarity	NPC88789
0.908	High Similarity	NPC197285
0.908	High Similarity	NPC118284
0.908	High Similarity	NPC281131
0.908	High Similarity	NPC135599
0.908	High Similarity	NPC253662
0.908	High Similarity	NPC308404
0.908	High Similarity	NPC236934
0.908	High Similarity	NPC113968
0.908	High Similarity	NPC21100
0.908	High Similarity	NPC179950
0.908	High Similarity	NPC5778
0.908	High Similarity	NPC274618
0.908	High Similarity	NPC328940
0.908	High Similarity	NPC276222
0.908	High Similarity	NPC56077
0.9074	High Similarity	NPC19709
0.9074	High Similarity	NPC41301
0.9074	High Similarity	NPC88043
0.9074	High Similarity	NPC29830
0.9068	High Similarity	NPC173137
0.9068	High Similarity	NPC471499
0.9062	High Similarity	NPC143828
0.9062	High Similarity	NPC19687
0.9062	High Similarity	NPC7846
0.9062	High Similarity	NPC288669
0.9062	High Similarity	NPC18607
0.9062	High Similarity	NPC152166
0.9062	High Similarity	NPC22192
0.9062	High Similarity	NPC25495
0.9062	High Similarity	NPC261004
0.9062	High Similarity	NPC204854
0.9062	High Similarity	NPC105242
0.9062	High Similarity	NPC130894
0.9062	High Similarity	NPC300943
0.9062	High Similarity	NPC9609
0.9062	High Similarity	NPC191459
0.9062	High Similarity	NPC18772
0.9062	High Similarity	NPC176300
0.9062	High Similarity	NPC253634
0.9062	High Similarity	NPC115798
0.9062	High Similarity	NPC4481
0.9062	High Similarity	NPC22472
0.9057	High Similarity	NPC326037
0.9057	High Similarity	NPC49824
0.9057	High Similarity	NPC250922
0.9057	High Similarity	NPC98661
0.9057	High Similarity	NPC303255
0.9057	High Similarity	NPC474520
0.9057	High Similarity	NPC320825
0.9057	High Similarity	NPC13858
0.9057	High Similarity	NPC247017
0.9057	High Similarity	NPC265511
0.9051	High Similarity	NPC18727
0.9051	High Similarity	NPC162351
0.9051	High Similarity	NPC78326
0.9051	High Similarity	NPC58382
0.9051	High Similarity	NPC236223
0.9051	High Similarity	NPC179126
0.9051	High Similarity	NPC270620
0.9045	High Similarity	NPC133953
0.9045	High Similarity	NPC125062
0.9045	High Similarity	NPC200740
0.9045	High Similarity	NPC54394
0.9045	High Similarity	NPC28274
0.9045	High Similarity	NPC252933
0.9045	High Similarity	NPC50403
0.9042	High Similarity	NPC89127
0.9042	High Similarity	NPC471669
0.9042	High Similarity	NPC144097
0.9042	High Similarity	NPC61904
0.9042	High Similarity	NPC473862
0.9038	High Similarity	NPC87125
0.9038	High Similarity	NPC270465
0.9036	High Similarity	NPC175230
0.9036	High Similarity	NPC172033
0.9036	High Similarity	NPC169977
0.9036	High Similarity	NPC45522
0.9036	High Similarity	NPC21666
0.9036	High Similarity	NPC42773
0.9036	High Similarity	NPC101026
0.9036	High Similarity	NPC88560
0.9036	High Similarity	NPC24043
0.903	High Similarity	NPC245014
0.903	High Similarity	NPC84265
0.903	High Similarity	NPC149011
0.903	High Similarity	NPC67105
0.903	High Similarity	NPC206123
0.903	High Similarity	NPC22195
0.903	High Similarity	NPC95866
0.903	High Similarity	NPC21190
0.903	High Similarity	NPC72249
0.903	High Similarity	NPC204937
0.903	High Similarity	NPC282987
0.903	High Similarity	NPC183357
0.9024	High Similarity	NPC229729
0.9024	High Similarity	NPC265530
0.9024	High Similarity	NPC48640
0.9024	High Similarity	NPC325555
0.9024	High Similarity	NPC45400
0.9024	High Similarity	NPC149244
0.9024	High Similarity	NPC226304
0.9024	High Similarity	NPC42892
0.9018	High Similarity	NPC62261
0.9018	High Similarity	NPC22832
0.9018	High Similarity	NPC55786
0.9018	High Similarity	NPC19388
0.9018	High Similarity	NPC224280
0.9018	High Similarity	NPC240431
0.9018	High Similarity	NPC311830
0.9012	High Similarity	NPC473043
0.9012	High Similarity	NPC189142
0.9012	High Similarity	NPC77660
0.9006	High Similarity	NPC282009
0.9006	High Similarity	NPC263449
0.9006	High Similarity	NPC287328
0.9006	High Similarity	NPC470326

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 NPC88243 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	956
0.2-0.3	1931
0.3-0.4	2622
0.4-0.5	1727
0.5-0.6	962
0.6-0.7	387
0.7-0.8	147
0.8-0.85	30
0.85-0.9	20
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9096	High Similarity	NPD4338	Clinical (unspecified phase)
0.8994	High Similarity	NPD3817	Phase 2
0.8987	High Similarity	NPD1934	Approved
0.8976	High Similarity	NPD6797	Phase 2
0.8931	High Similarity	NPD2393	Clinical (unspecified phase)
0.8931	High Similarity	NPD2801	Approved
0.8922	High Similarity	NPD7251	Discontinued
0.8916	High Similarity	NPD7074	Phase 3
0.8909	High Similarity	NPD3818	Discontinued
0.8902	High Similarity	NPD6166	Phase 2
0.8902	High Similarity	NPD6168	Clinical (unspecified phase)
0.8902	High Similarity	NPD6167	Clinical (unspecified phase)
0.8855	High Similarity	NPD7054	Approved
0.8846	High Similarity	NPD1512	Approved
0.882	High Similarity	NPD3882	Suspended
0.882	High Similarity	NPD4868	Clinical (unspecified phase)
0.8802	High Similarity	NPD7472	Approved
0.8765	High Similarity	NPD7075	Discontinued
0.8757	High Similarity	NPD7808	Phase 3
0.8718	High Similarity	NPD1511	Approved
0.865	High Similarity	NPD4381	Clinical (unspecified phase)
0.858	High Similarity	NPD7096	Clinical (unspecified phase)
0.8554	High Similarity	NPD6232	Discontinued
0.8544	High Similarity	NPD4378	Clinical (unspecified phase)
0.8529	High Similarity	NPD7993	Clinical (unspecified phase)
0.8521	High Similarity	NPD7804	Clinical (unspecified phase)
0.8512	High Similarity	NPD7473	Discontinued
0.8481	Intermediate Similarity	NPD6799	Approved
0.8405	Intermediate Similarity	NPD6801	Discontinued
0.8354	Intermediate Similarity	NPD7819	Suspended
0.8354	Intermediate Similarity	NPD1465	Phase 2
0.8303	Intermediate Similarity	NPD5402	Approved
0.8282	Intermediate Similarity	NPD6599	Discontinued
0.8282	Intermediate Similarity	NPD4380	Phase 2
0.8266	Intermediate Similarity	NPD6559	Discontinued
0.8232	Intermediate Similarity	NPD7411	Suspended
0.8217	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1549	Phase 2
0.8156	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD5494	Approved
0.8098	Intermediate Similarity	NPD5403	Approved
0.8086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3926	Phase 2
0.807	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD3751	Discontinued
0.7989	Intermediate Similarity	NPD5844	Phase 1
0.7988	Intermediate Similarity	NPD3749	Approved
0.7976	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1510	Phase 2
0.7975	Intermediate Similarity	NPD5401	Approved
0.7953	Intermediate Similarity	NPD7199	Phase 2
0.795	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1240	Approved
0.7949	Intermediate Similarity	NPD943	Approved
0.7941	Intermediate Similarity	NPD6234	Discontinued
0.7941	Intermediate Similarity	NPD919	Approved
0.7937	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD2796	Approved
0.7919	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3787	Discontinued
0.7901	Intermediate Similarity	NPD6190	Approved
0.7898	Intermediate Similarity	NPD1933	Approved
0.7898	Intermediate Similarity	NPD230	Phase 1
0.7849	Intermediate Similarity	NPD6959	Discontinued
0.7848	Intermediate Similarity	NPD1607	Approved
0.7845	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD3750	Approved
0.7831	Intermediate Similarity	NPD1653	Approved
0.7812	Intermediate Similarity	NPD2935	Discontinued
0.7806	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD447	Suspended
0.7784	Intermediate Similarity	NPD3226	Approved
0.7758	Intermediate Similarity	NPD2534	Approved
0.7758	Intermediate Similarity	NPD2532	Approved
0.7758	Intermediate Similarity	NPD2533	Approved
0.7753	Intermediate Similarity	NPD7685	Pre-registration
0.7751	Intermediate Similarity	NPD37	Approved
0.7746	Intermediate Similarity	NPD1247	Approved
0.7742	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7228	Approved
0.7725	Intermediate Similarity	NPD7435	Discontinued
0.7722	Intermediate Similarity	NPD1613	Approved
0.7722	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD4966	Approved
0.7719	Intermediate Similarity	NPD4967	Phase 2
0.7719	Intermediate Similarity	NPD4965	Approved
0.7719	Intermediate Similarity	NPD7768	Phase 2
0.7707	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1551	Phase 2
0.7697	Intermediate Similarity	NPD5953	Discontinued
0.7669	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8313	Approved
0.7667	Intermediate Similarity	NPD8312	Approved
0.766	Intermediate Similarity	NPD6776	Approved
0.766	Intermediate Similarity	NPD6782	Approved
0.766	Intermediate Similarity	NPD6781	Approved
0.766	Intermediate Similarity	NPD6778	Approved
0.766	Intermediate Similarity	NPD6779	Approved
0.766	Intermediate Similarity	NPD6780	Approved
0.766	Intermediate Similarity	NPD6777	Approved
0.764	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8434	Phase 2
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7561	Intermediate Similarity	NPD2800	Approved
0.756	Intermediate Similarity	NPD920	Approved
0.7546	Intermediate Similarity	NPD2346	Discontinued
0.7531	Intermediate Similarity	NPD2799	Discontinued
0.7531	Intermediate Similarity	NPD3748	Approved
0.7526	Intermediate Similarity	NPD8151	Discontinued
0.7515	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7874	Approved
0.7487	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7485	Intermediate Similarity	NPD6100	Approved
0.7485	Intermediate Similarity	NPD6099	Approved
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7455	Intermediate Similarity	NPD1243	Approved
0.7448	Intermediate Similarity	NPD7696	Phase 3
0.7448	Intermediate Similarity	NPD7697	Approved
0.7448	Intermediate Similarity	NPD7698	Approved
0.7446	Intermediate Similarity	NPD8150	Discontinued
0.744	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7266	Discontinued
0.7439	Intermediate Similarity	NPD2344	Approved
0.7421	Intermediate Similarity	NPD3027	Phase 3
0.7409	Intermediate Similarity	NPD7871	Phase 2
0.7409	Intermediate Similarity	NPD7870	Phase 2
0.7407	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6535	Approved
0.7394	Intermediate Similarity	NPD6534	Approved
0.7389	Intermediate Similarity	NPD1203	Approved
0.7385	Intermediate Similarity	NPD7701	Phase 2
0.7382	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6798	Discontinued
0.736	Intermediate Similarity	NPD7783	Phase 2
0.736	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD7584	Approved
0.7321	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8319	Approved
0.732	Intermediate Similarity	NPD8320	Phase 1
0.7317	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7033	Discontinued
0.7308	Intermediate Similarity	NPD9269	Phase 2
0.7303	Intermediate Similarity	NPD5710	Approved
0.7303	Intermediate Similarity	NPD5711	Approved
0.7301	Intermediate Similarity	NPD6651	Approved
0.7299	Intermediate Similarity	NPD8455	Phase 2
0.7277	Intermediate Similarity	NPD7700	Phase 2
0.7277	Intermediate Similarity	NPD7699	Phase 2
0.7273	Intermediate Similarity	NPD7801	Approved
0.7268	Intermediate Similarity	NPD7240	Approved
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD3268	Approved
0.7263	Intermediate Similarity	NPD5242	Approved
0.7262	Intermediate Similarity	NPD2309	Approved
0.7262	Intermediate Similarity	NPD2354	Approved
0.7239	Intermediate Similarity	NPD6355	Discontinued
0.7239	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2798	Approved
0.7222	Intermediate Similarity	NPD6233	Phase 2
0.7222	Intermediate Similarity	NPD2403	Approved
0.7212	Intermediate Similarity	NPD4308	Phase 3
0.7205	Intermediate Similarity	NPD7095	Approved
0.7197	Intermediate Similarity	NPD1608	Approved
0.7197	Intermediate Similarity	NPD9717	Approved
0.7188	Intermediate Similarity	NPD9494	Approved
0.7184	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4060	Phase 1
0.7176	Intermediate Similarity	NPD7390	Discontinued
0.717	Intermediate Similarity	NPD2797	Approved
0.7159	Intermediate Similarity	NPD5353	Approved
0.7152	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7097	Phase 1
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7135	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD422	Phase 1
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.7127	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7585	Approved
0.7111	Intermediate Similarity	NPD7229	Phase 3
0.7093	Intermediate Similarity	NPD5049	Phase 3
0.709	Intermediate Similarity	NPD4287	Approved
0.7086	Intermediate Similarity	NPD6386	Approved
0.7086	Intermediate Similarity	NPD6385	Approved
0.7071	Intermediate Similarity	NPD7583	Approved
0.7059	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3887	Approved
0.7055	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3764	Approved
0.7055	Intermediate Similarity	NPD411	Approved
0.7051	Intermediate Similarity	NPD9268	Approved
0.7041	Intermediate Similarity	NPD5006	Approved
0.7041	Intermediate Similarity	NPD1652	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