NPASS Compound

Structure

NPC476306 OpenBabel07101719522D 32 36 0 0 1 0 0 0 0 0999 V2000 1.1248 3.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6594 1.8912 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 5.1962 3.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 3.4641 1.0000 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 24 1 0 0 0 0 2 24 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 17 2 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 26 1 0 0 0 0 13 14 2 0 0 0 0 13 23 1 0 0 0 0 14 22 1 0 0 0 0 15 22 2 0 0 0 0 15 27 1 0 0 0 0 16 19 2 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 17 31 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 1 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 29 2 0 0 0 0 21 23 2 0 0 0 0 21 30 1 0 0 0 0 22 32 1 0 0 0 0 23 31 1 0 0 0 0 25 3 1 6 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.17
Volume:	438.614
LogP:	5.241
LogD:	3.254
LogS:	-4.084
# Rotatable Bonds:	1
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.431
Synthetic Accessibility Score:	3.97
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.9
MDCK Permeability:	1.4142262443783693e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	98.51386260986328%
Volume Distribution (VD):	0.518
Pgp-substrate:	3.617213726043701%

ADMET: Metabolism

CYP1A2-inhibitor:	0.775
CYP1A2-substrate:	0.552
CYP2C19-inhibitor:	0.521
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.664
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.549
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.311
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	5.729
Half-life (T1/2):	0.494

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.435
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.743
Skin Sensitization:	0.855
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.862
Respiratory Toxicity:	0.647

Download Data

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

Natural Product: NPC476306

Natural Product ID:	NPC476306
*Common Name:**	Ugonin N
IUPAC Name:	2-[(8aR,10aS)-4-hydroxy-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthen-1-yl]-3,5,7-trihydroxychromen-4-one
Synonyms:	Ugonin N
Standard InCHIKey:	RQGIPLQXOXXTRU-CJAUYULYSA-N
Standard InCHI:	InChI=1S/C25H26O7/c1-24(2)7-4-8-25(3)18(24)11-14-13(5-6-15(27)22(14)32-25)23-21(30)20(29)19-16(28)9-12(26)10-17(19)31-23/h5-6,9-10,18,26-28,30H,4,7-8,11H2,1-3H3/t18-,25+/m1/s1
SMILES:	CC1(CCCC2(C1CC3=C(C=CC(=C3O2)O)C4=C(C(=O)C5=C(C=C(C=C5O4)O)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563382
PubChem CID:	44233937
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003587] 2'-prenylated flavones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19583252]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[28169537]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[558832]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[558832]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[558832]

☑ 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 NPC476306 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	484
0.1-0.2	1888
0.2-0.3	3709
0.3-0.4	9564
0.4-0.5	8709
0.5-0.6	4109
0.6-0.7	5412
0.7-0.8	5352
0.8-0.85	2274
0.85-0.9	1016
0.9-0.95	169
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC206605
0.956	High Similarity	NPC12461
0.9557	High Similarity	NPC472906
0.9497	High Similarity	NPC78332
0.9494	High Similarity	NPC476280
0.943	High Similarity	NPC280680
0.943	High Similarity	NPC46736
0.9371	High Similarity	NPC471973
0.9371	High Similarity	NPC297212
0.9321	High Similarity	NPC472449
0.9317	High Similarity	NPC186686
0.9317	High Similarity	NPC189473
0.9317	High Similarity	NPC23298
0.9313	High Similarity	NPC234644
0.9308	High Similarity	NPC235448
0.9308	High Similarity	NPC197856
0.9304	High Similarity	NPC3980
0.9259	High Similarity	NPC275780
0.9259	High Similarity	NPC472450
0.9259	High Similarity	NPC239752
0.9255	High Similarity	NPC474150
0.9255	High Similarity	NPC474162
0.925	High Similarity	NPC474960
0.925	High Similarity	NPC139036
0.925	High Similarity	NPC188433
0.9245	High Similarity	NPC136674
0.9245	High Similarity	NPC273843
0.9207	High Similarity	NPC188079
0.9207	High Similarity	NPC165456
0.9207	High Similarity	NPC476637
0.9202	High Similarity	NPC43319
0.9202	High Similarity	NPC39091
0.9202	High Similarity	NPC37870
0.9198	High Similarity	NPC303460
0.9198	High Similarity	NPC476295
0.9198	High Similarity	NPC306321
0.9198	High Similarity	NPC472625
0.9198	High Similarity	NPC220313
0.9193	High Similarity	NPC57715
0.9187	High Similarity	NPC474290
0.9182	High Similarity	NPC13779
0.9182	High Similarity	NPC472907
0.9182	High Similarity	NPC475799
0.9182	High Similarity	NPC471985
0.9177	High Similarity	NPC472905
0.9152	High Similarity	NPC101107
0.9146	High Similarity	NPC150131
0.9146	High Similarity	NPC218226
0.9141	High Similarity	NPC62261
0.9141	High Similarity	NPC156432
0.9141	High Similarity	NPC293319
0.9136	High Similarity	NPC25152
0.9136	High Similarity	NPC229632
0.9136	High Similarity	NPC329760
0.913	High Similarity	NPC80375
0.913	High Similarity	NPC204290
0.913	High Similarity	NPC200746
0.913	High Similarity	NPC192686
0.913	High Similarity	NPC118256
0.913	High Similarity	NPC235018
0.913	High Similarity	NPC36217
0.913	High Similarity	NPC119209
0.913	High Similarity	NPC45146
0.9125	High Similarity	NPC218313
0.9125	High Similarity	NPC474681
0.9125	High Similarity	NPC237418
0.9125	High Similarity	NPC67876
0.9125	High Similarity	NPC187745
0.9125	High Similarity	NPC161960
0.9125	High Similarity	NPC304008
0.9125	High Similarity	NPC472963
0.9119	High Similarity	NPC56786
0.9119	High Similarity	NPC80534
0.9114	High Similarity	NPC37684
0.9114	High Similarity	NPC157784
0.9114	High Similarity	NPC63187
0.9096	High Similarity	NPC4200
0.9091	High Similarity	NPC288813
0.9091	High Similarity	NPC475805
0.9085	High Similarity	NPC477517
0.9085	High Similarity	NPC272502
0.908	High Similarity	NPC152659
0.908	High Similarity	NPC207690
0.908	High Similarity	NPC146134
0.908	High Similarity	NPC236521
0.908	High Similarity	NPC248638
0.9074	High Similarity	NPC167678
0.9074	High Similarity	NPC29876
0.9074	High Similarity	NPC474038
0.9074	High Similarity	NPC32694
0.9074	High Similarity	NPC173137
0.9074	High Similarity	NPC61010
0.9068	High Similarity	NPC204879
0.9068	High Similarity	NPC476242
0.9068	High Similarity	NPC55738
0.9068	High Similarity	NPC100123
0.9062	High Similarity	NPC6633
0.9062	High Similarity	NPC274730
0.9062	High Similarity	NPC133970
0.9062	High Similarity	NPC5322
0.9062	High Similarity	NPC115853
0.9062	High Similarity	NPC24640
0.9057	High Similarity	NPC170492
0.9057	High Similarity	NPC236223
0.9057	High Similarity	NPC78326
0.9057	High Similarity	NPC179126
0.9057	High Similarity	NPC270620
0.9051	High Similarity	NPC205046
0.9051	High Similarity	NPC59162
0.9051	High Similarity	NPC125062
0.9051	High Similarity	NPC200740
0.9051	High Similarity	NPC54394
0.9051	High Similarity	NPC304295
0.9051	High Similarity	NPC252933
0.9036	High Similarity	NPC279209
0.9036	High Similarity	NPC102277
0.903	High Similarity	NPC126204
0.9024	High Similarity	NPC224280
0.9024	High Similarity	NPC125039
0.9024	High Similarity	NPC7154
0.9024	High Similarity	NPC72787
0.9024	High Similarity	NPC58223
0.9024	High Similarity	NPC36
0.9024	High Similarity	NPC475888
0.9024	High Similarity	NPC36916
0.9024	High Similarity	NPC303174
0.9024	High Similarity	NPC7688
0.9018	High Similarity	NPC211107
0.9018	High Similarity	NPC83922
0.9018	High Similarity	NPC472964
0.9018	High Similarity	NPC472448
0.9018	High Similarity	NPC201800
0.9012	High Similarity	NPC470183
0.9012	High Similarity	NPC14353
0.9012	High Similarity	NPC228785
0.9012	High Similarity	NPC472902
0.9012	High Similarity	NPC282009
0.9012	High Similarity	NPC320359
0.9012	High Similarity	NPC56085
0.9012	High Similarity	NPC287328
0.9012	High Similarity	NPC475784
0.9006	High Similarity	NPC471479
0.9006	High Similarity	NPC219867
0.9006	High Similarity	NPC299520
0.9006	High Similarity	NPC471515
0.9006	High Similarity	NPC476170
0.9006	High Similarity	NPC180011
0.9006	High Similarity	NPC27337
0.9006	High Similarity	NPC241904
0.9006	High Similarity	NPC473272
0.9006	High Similarity	NPC52889
0.9006	High Similarity	NPC111969
0.9006	High Similarity	NPC284820
0.9006	High Similarity	NPC300727
0.9006	High Similarity	NPC129684
0.9	High Similarity	NPC234255
0.9	High Similarity	NPC133392
0.9	High Similarity	NPC200246
0.9	High Similarity	NPC472280
0.9	High Similarity	NPC67396
0.8994	High Similarity	NPC237994
0.8994	High Similarity	NPC260979
0.8994	High Similarity	NPC279989
0.8994	High Similarity	NPC472912
0.8994	High Similarity	NPC55205
0.8994	High Similarity	NPC471982
0.8994	High Similarity	NPC82325
0.8987	High Similarity	NPC88804
0.8987	High Similarity	NPC50728
0.8987	High Similarity	NPC151473
0.8987	High Similarity	NPC3825
0.8987	High Similarity	NPC166753
0.8976	High Similarity	NPC177480
0.8976	High Similarity	NPC107627
0.8976	High Similarity	NPC300307
0.897	High Similarity	NPC120593
0.897	High Similarity	NPC471213
0.8963	High Similarity	NPC474240
0.8963	High Similarity	NPC41301
0.8963	High Similarity	NPC319200
0.8963	High Similarity	NPC187491
0.8957	High Similarity	NPC472632
0.8957	High Similarity	NPC472275
0.8957	High Similarity	NPC278052
0.8957	High Similarity	NPC278427
0.8957	High Similarity	NPC84324
0.8957	High Similarity	NPC40491
0.8957	High Similarity	NPC471499
0.8957	High Similarity	NPC165970
0.8957	High Similarity	NPC187354
0.8957	High Similarity	NPC471210
0.8957	High Similarity	NPC288131
0.8957	High Similarity	NPC305987
0.8957	High Similarity	NPC289771
0.8957	High Similarity	NPC259456
0.8957	High Similarity	NPC26326
0.8957	High Similarity	NPC66618
0.8957	High Similarity	NPC113163
0.8951	High Similarity	NPC74178
0.8951	High Similarity	NPC210459

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 NPC476306 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	424
0.1-0.2	980
0.2-0.3	1736
0.3-0.4	2698
0.4-0.5	1872
0.5-0.6	902
0.6-0.7	355
0.7-0.8	148
0.8-0.85	23
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9024	High Similarity	NPD6167	Clinical (unspecified phase)
0.9024	High Similarity	NPD6168	Clinical (unspecified phase)
0.9024	High Similarity	NPD6166	Phase 2
0.8875	High Similarity	NPD1934	Approved
0.8854	High Similarity	NPD1512	Approved
0.882	High Similarity	NPD2801	Approved
0.882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8726	High Similarity	NPD1511	Approved
0.8598	High Similarity	NPD3882	Suspended
0.8553	High Similarity	NPD4378	Clinical (unspecified phase)
0.8538	High Similarity	NPD6797	Phase 2
0.8537	High Similarity	NPD3817	Phase 2
0.8529	High Similarity	NPD7054	Approved
0.8488	Intermediate Similarity	NPD7251	Discontinued
0.848	Intermediate Similarity	NPD7472	Approved
0.848	Intermediate Similarity	NPD7074	Phase 3
0.8439	Intermediate Similarity	NPD7808	Phase 3
0.8412	Intermediate Similarity	NPD7473	Discontinued
0.8343	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD5494	Approved
0.8333	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD4380	Phase 2
0.8284	Intermediate Similarity	NPD6959	Discontinued
0.8263	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD3818	Discontinued
0.8253	Intermediate Similarity	NPD1465	Phase 2
0.8214	Intermediate Similarity	NPD7075	Discontinued
0.8208	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD5844	Phase 1
0.8204	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7819	Suspended
0.8114	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6801	Discontinued
0.7963	Intermediate Similarity	NPD3750	Approved
0.795	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1549	Phase 2
0.7937	Intermediate Similarity	NPD6099	Approved
0.7937	Intermediate Similarity	NPD6100	Approved
0.7927	Intermediate Similarity	NPD6799	Approved
0.7917	Intermediate Similarity	NPD7411	Suspended
0.7875	Intermediate Similarity	NPD1510	Phase 2
0.7841	Intermediate Similarity	NPD3751	Discontinued
0.7829	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD2796	Approved
0.7816	Intermediate Similarity	NPD3787	Discontinued
0.7791	Intermediate Similarity	NPD2800	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5402	Approved
0.7772	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3926	Phase 2
0.7764	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD1247	Approved
0.7746	Intermediate Similarity	NPD919	Approved
0.7736	Intermediate Similarity	NPD1240	Approved
0.7736	Intermediate Similarity	NPD943	Approved
0.7711	Intermediate Similarity	NPD7390	Discontinued
0.7707	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5403	Approved
0.7663	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7199	Phase 2
0.7654	Intermediate Similarity	NPD3748	Approved
0.7644	Intermediate Similarity	NPD6234	Discontinued
0.7643	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1607	Approved
0.764	Intermediate Similarity	NPD7228	Approved
0.7636	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7768	Phase 2
0.7588	Intermediate Similarity	NPD3226	Approved
0.7569	Intermediate Similarity	NPD6559	Discontinued
0.756	Intermediate Similarity	NPD2532	Approved
0.756	Intermediate Similarity	NPD5401	Approved
0.756	Intermediate Similarity	NPD2533	Approved
0.756	Intermediate Similarity	NPD2534	Approved
0.7554	Intermediate Similarity	NPD8150	Discontinued
0.7546	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1613	Approved
0.7516	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.7486	Intermediate Similarity	NPD8312	Approved
0.7471	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8434	Phase 2
0.7457	Intermediate Similarity	NPD37	Approved
0.7455	Intermediate Similarity	NPD2346	Discontinued
0.7429	Intermediate Similarity	NPD4965	Approved
0.7429	Intermediate Similarity	NPD4966	Approved
0.7429	Intermediate Similarity	NPD4967	Phase 2
0.7425	Intermediate Similarity	NPD4628	Phase 3
0.7423	Intermediate Similarity	NPD6651	Approved
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7391	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4908	Phase 1
0.7371	Intermediate Similarity	NPD7435	Discontinued
0.7365	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD447	Suspended
0.7358	Intermediate Similarity	NPD2494	Approved
0.7358	Intermediate Similarity	NPD2493	Approved
0.7353	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4582	Approved
0.7333	Intermediate Similarity	NPD4583	Approved
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.7329	Intermediate Similarity	NPD3027	Phase 3
0.7329	Intermediate Similarity	NPD4625	Phase 3
0.7294	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7458	Discontinued
0.7283	Intermediate Similarity	NPD7685	Pre-registration
0.7282	Intermediate Similarity	NPD7697	Approved
0.7282	Intermediate Similarity	NPD7696	Phase 3
0.7282	Intermediate Similarity	NPD4002	Approved
0.7282	Intermediate Similarity	NPD7698	Approved
0.7282	Intermediate Similarity	NPD4004	Approved
0.7278	Intermediate Similarity	NPD6190	Approved
0.7268	Intermediate Similarity	NPD3450	Approved
0.7268	Intermediate Similarity	NPD3452	Approved
0.7262	Intermediate Similarity	NPD1243	Approved
0.7256	Intermediate Similarity	NPD230	Phase 1
0.7249	Intermediate Similarity	NPD2488	Approved
0.7249	Intermediate Similarity	NPD2490	Approved
0.7246	Intermediate Similarity	NPD2344	Approved
0.7245	Intermediate Similarity	NPD7870	Phase 2
0.7245	Intermediate Similarity	NPD7871	Phase 2
0.724	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3300	Phase 2
0.7225	Intermediate Similarity	NPD6534	Approved
0.7225	Intermediate Similarity	NPD6535	Approved
0.7225	Intermediate Similarity	NPD4363	Phase 3
0.7225	Intermediate Similarity	NPD4360	Phase 2
0.7222	Intermediate Similarity	NPD7095	Approved
0.7222	Intermediate Similarity	NPD7701	Phase 2
0.7219	Intermediate Similarity	NPD7003	Approved
0.7219	Intermediate Similarity	NPD8166	Discontinued
0.7206	Intermediate Similarity	NPD4111	Phase 1
0.7206	Intermediate Similarity	NPD4665	Approved
0.7204	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7801	Approved
0.7195	Intermediate Similarity	NPD4060	Phase 1
0.7189	Intermediate Similarity	NPD7240	Approved
0.7186	Intermediate Similarity	NPD8151	Discontinued
0.7186	Intermediate Similarity	NPD1551	Phase 2
0.7184	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2313	Discontinued
0.7178	Intermediate Similarity	NPD3268	Approved
0.7178	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD920	Approved
0.7167	Intermediate Similarity	NPD8127	Discontinued
0.7152	Intermediate Similarity	NPD1201	Approved
0.7152	Intermediate Similarity	NPD1933	Approved
0.7151	Intermediate Similarity	NPD7549	Discontinued
0.715	Intermediate Similarity	NPD2974	Approved
0.715	Intermediate Similarity	NPD2973	Approved
0.715	Intermediate Similarity	NPD2975	Approved
0.715	Intermediate Similarity	NPD7874	Approved
0.715	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD2798	Approved
0.7136	Intermediate Similarity	NPD7907	Approved
0.7128	Intermediate Similarity	NPD4580	Approved
0.7127	Intermediate Similarity	NPD5710	Approved
0.7127	Intermediate Similarity	NPD7229	Phase 3
0.7127	Intermediate Similarity	NPD5711	Approved
0.7126	Intermediate Similarity	NPD1653	Approved
0.7114	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7783	Phase 2
0.7113	Intermediate Similarity	NPD7699	Phase 2
0.7113	Intermediate Similarity	NPD7700	Phase 2
0.711	Intermediate Similarity	NPD6273	Approved
0.7105	Intermediate Similarity	NPD4287	Approved
0.7083	Intermediate Similarity	NPD5405	Approved
0.7083	Intermediate Similarity	NPD5404	Approved
0.7083	Intermediate Similarity	NPD5408	Approved
0.7083	Intermediate Similarity	NPD5406	Approved
0.7081	Intermediate Similarity	NPD1470	Approved
0.7081	Intermediate Similarity	NPD2797	Approved
0.7079	Intermediate Similarity	NPD4288	Approved
0.7076	Intermediate Similarity	NPD2309	Approved
0.7073	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8320	Phase 1
0.7071	Intermediate Similarity	NPD8319	Approved
0.7063	Intermediate Similarity	NPD4749	Approved
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6823	Phase 2
0.7052	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1610	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