NPASS Compound

Structure

NPC291110 OpenBabel07101719402D 25 27 0 0 0 0 0 0 0 0999 V2000 5.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 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 4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.9230 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 9 2 0 0 0 0 4 15 1 0 0 0 0 5 9 1 0 0 0 0 5 16 2 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 18 2 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 25 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.09
Volume:	334.655
LogP:	2.817
LogD:	2.792
LogS:	-4.267
# Rotatable Bonds:	5
TPSA:	98.36
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	2.678
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.011
MDCK Permeability:	1.4889207704982255e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.087
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	88.8495101928711%
Volume Distribution (VD):	0.966
Pgp-substrate:	12.152996063232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.138
CYP2C19-substrate:	0.164
CYP2C9-inhibitor:	0.283
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.272
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.6
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	10.728
Half-life (T1/2):	0.724

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.611
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.134
Carcinogencity:	0.028
Eye Corrosion:	0.016
Eye Irritation:	0.92
Respiratory Toxicity:	0.504

Download Data

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

Natural Product: NPC291110

Natural Product ID:	NPC291110
*Common Name:**	Lespedezavirgatal
IUPAC Name:	5,6-dihydroxy-2-(2,4,6-trimethoxyphenyl)-1-benzofuran-3-carbaldehyde
Synonyms:	Lespedezavirgatal
Standard InCHIKey:	OUBWKVRCMQAWKH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O7/c1-22-9-4-15(23-2)17(16(5-9)24-3)18-11(8-19)10-6-12(20)13(21)7-14(10)25-18/h4-8,20-21H,1-3H3
SMILES:	COc1cc(OC)c(c(c1)OC)c1oc2c(c1C=O)cc(c(c2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520533
PubChem CID:	24899158
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran 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
NPO8311	Lespedeza virgata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17890083]
NPO8311	Lespedeza virgata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18484774]

☑ 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	2
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	188.99	n.a.	PMID[452627]
NPT614	Tissue	Plasma	Rattus norvegicus	IC50	=	750000.0	nM	PMID[452627]
NPT1590	Tissue	Kidney	Rattus norvegicus	IC50	=	640000.0	nM	PMID[452627]

☑ 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 NPC291110 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	419
0.1-0.2	1851
0.2-0.3	4572
0.3-0.4	11178
0.4-0.5	6857
0.5-0.6	3834
0.6-0.7	5206
0.7-0.8	5313
0.8-0.85	2049
0.85-0.9	1119
0.9-0.95	298
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9497	High Similarity	NPC37183
0.9494	High Similarity	NPC84515
0.9494	High Similarity	NPC312056
0.9437	High Similarity	NPC277480
0.9434	High Similarity	NPC133065
0.943	High Similarity	NPC188486
0.9427	High Similarity	NPC196879
0.9379	High Similarity	NPC86477
0.9379	High Similarity	NPC247973
0.9379	High Similarity	NPC50394
0.9375	High Similarity	NPC39306
0.9355	High Similarity	NPC125300
0.9325	High Similarity	NPC307286
0.9304	High Similarity	NPC16935
0.9299	High Similarity	NPC45131
0.9268	High Similarity	NPC261471
0.9264	High Similarity	NPC78830
0.9264	High Similarity	NPC218533
0.9264	High Similarity	NPC131866
0.9255	High Similarity	NPC36320
0.9255	High Similarity	NPC29411
0.9255	High Similarity	NPC45449
0.9231	High Similarity	NPC67654
0.9212	High Similarity	NPC290304
0.9212	High Similarity	NPC236327
0.9207	High Similarity	NPC174700
0.9193	High Similarity	NPC1755
0.9193	High Similarity	NPC39305
0.9193	High Similarity	NPC1706
0.9193	High Similarity	NPC263092
0.9193	High Similarity	NPC59295
0.9177	High Similarity	NPC247677
0.9177	High Similarity	NPC160015
0.9167	High Similarity	NPC156244
0.9152	High Similarity	NPC310794
0.9152	High Similarity	NPC37606
0.9152	High Similarity	NPC473834
0.9136	High Similarity	NPC38914
0.913	High Similarity	NPC272722
0.913	High Similarity	NPC238995
0.9119	High Similarity	NPC296957
0.9119	High Similarity	NPC260902
0.9096	High Similarity	NPC287243
0.9085	High Similarity	NPC202470
0.9085	High Similarity	NPC247136
0.9074	High Similarity	NPC329669
0.9074	High Similarity	NPC472278
0.9074	High Similarity	NPC473313
0.9062	High Similarity	NPC476349
0.9062	High Similarity	NPC476350
0.9045	High Similarity	NPC106372
0.9045	High Similarity	NPC58668
0.9042	High Similarity	NPC164384
0.9036	High Similarity	NPC216842
0.9036	High Similarity	NPC277510
0.9036	High Similarity	NPC476640
0.9036	High Similarity	NPC82217
0.9032	High Similarity	NPC17816
0.9024	High Similarity	NPC186392
0.9024	High Similarity	NPC241820
0.9012	High Similarity	NPC81679
0.9	High Similarity	NPC469584
0.8994	High Similarity	NPC113906
0.8987	High Similarity	NPC207624
0.8976	High Similarity	NPC54098
0.8976	High Similarity	NPC248593
0.8976	High Similarity	NPC28589
0.8976	High Similarity	NPC230619
0.8957	High Similarity	NPC475985
0.8947	High Similarity	NPC304322
0.8944	High Similarity	NPC329091
0.8944	High Similarity	NPC195832
0.8944	High Similarity	NPC472877
0.8938	High Similarity	NPC472916
0.8938	High Similarity	NPC472461
0.8931	High Similarity	NPC89474
0.8931	High Similarity	NPC280937
0.8931	High Similarity	NPC183874
0.8929	High Similarity	NPC49667
0.8929	High Similarity	NPC8127
0.8924	High Similarity	NPC23668
0.8924	High Similarity	NPC170169
0.8924	High Similarity	NPC193976
0.8924	High Similarity	NPC115324
0.8922	High Similarity	NPC233956
0.8917	High Similarity	NPC178202
0.8916	High Similarity	NPC28042
0.8916	High Similarity	NPC476641
0.8909	High Similarity	NPC470704
0.8902	High Similarity	NPC326520
0.8902	High Similarity	NPC473286
0.8895	High Similarity	NPC73929
0.8895	High Similarity	NPC139683
0.8895	High Similarity	NPC47905
0.8889	High Similarity	NPC220582
0.8889	High Similarity	NPC304839
0.8889	High Similarity	NPC300680
0.8882	High Similarity	NPC299520
0.8882	High Similarity	NPC96167
0.8882	High Similarity	NPC97523
0.8882	High Similarity	NPC472913
0.8882	High Similarity	NPC475267
0.8882	High Similarity	NPC222814
0.8882	High Similarity	NPC472911
0.8882	High Similarity	NPC129684
0.8882	High Similarity	NPC474836
0.8882	High Similarity	NPC262286
0.8882	High Similarity	NPC474208
0.8882	High Similarity	NPC210084
0.8882	High Similarity	NPC472910
0.8882	High Similarity	NPC99597
0.8882	High Similarity	NPC36852
0.8882	High Similarity	NPC472914
0.8882	High Similarity	NPC48208
0.8882	High Similarity	NPC241904
0.8882	High Similarity	NPC181960
0.8882	High Similarity	NPC156057
0.8882	High Similarity	NPC245758
0.8882	High Similarity	NPC300727
0.8882	High Similarity	NPC162869
0.8876	High Similarity	NPC475783
0.8875	High Similarity	NPC2928
0.8875	High Similarity	NPC256612
0.8875	High Similarity	NPC148938
0.8875	High Similarity	NPC20830
0.8875	High Similarity	NPC213622
0.8875	High Similarity	NPC198490
0.8875	High Similarity	NPC208197
0.8869	High Similarity	NPC289244
0.8868	High Similarity	NPC5871
0.8868	High Similarity	NPC253872
0.8868	High Similarity	NPC101996
0.8868	High Similarity	NPC142308
0.8861	High Similarity	NPC167576
0.8861	High Similarity	NPC78335
0.8861	High Similarity	NPC230713
0.8861	High Similarity	NPC10467
0.8861	High Similarity	NPC62042
0.8861	High Similarity	NPC184136
0.8855	High Similarity	NPC211309
0.8854	High Similarity	NPC194856
0.8848	High Similarity	NPC170245
0.8841	High Similarity	NPC89131
0.8841	High Similarity	NPC18100
0.8841	High Similarity	NPC65846
0.8834	High Similarity	NPC45124
0.8834	High Similarity	NPC30655
0.8834	High Similarity	NPC74854
0.8834	High Similarity	NPC472275
0.8827	High Similarity	NPC185258
0.8827	High Similarity	NPC172770
0.8827	High Similarity	NPC476242
0.8824	High Similarity	NPC183843
0.882	High Similarity	NPC274730
0.882	High Similarity	NPC180924
0.882	High Similarity	NPC255106
0.882	High Similarity	NPC138243
0.882	High Similarity	NPC142339
0.882	High Similarity	NPC235165
0.8817	High Similarity	NPC24258
0.8812	High Similarity	NPC88645
0.8812	High Similarity	NPC47781
0.8812	High Similarity	NPC69394
0.8812	High Similarity	NPC235333
0.8812	High Similarity	NPC271779
0.8812	High Similarity	NPC250557
0.8812	High Similarity	NPC292214
0.8812	High Similarity	NPC176775
0.8812	High Similarity	NPC276409
0.8812	High Similarity	NPC472915
0.8812	High Similarity	NPC255350
0.8812	High Similarity	NPC206238
0.8812	High Similarity	NPC231018
0.8812	High Similarity	NPC250822
0.8812	High Similarity	NPC75279
0.8812	High Similarity	NPC160951
0.8812	High Similarity	NPC167091
0.8812	High Similarity	NPC1477
0.8812	High Similarity	NPC183878
0.8812	High Similarity	NPC274327
0.8812	High Similarity	NPC22519
0.8812	High Similarity	NPC145379
0.8812	High Similarity	NPC124714
0.8812	High Similarity	NPC213608
0.881	High Similarity	NPC65885
0.881	High Similarity	NPC117450
0.881	High Similarity	NPC30550
0.8805	High Similarity	NPC45291
0.8805	High Similarity	NPC171010
0.8805	High Similarity	NPC204515
0.8805	High Similarity	NPC19980
0.8805	High Similarity	NPC202157
0.8802	High Similarity	NPC281835
0.8797	High Similarity	NPC92722
0.8797	High Similarity	NPC226644
0.8797	High Similarity	NPC102003
0.8797	High Similarity	NPC37226
0.879	High Similarity	NPC207729
0.8788	High Similarity	NPC472277
0.8782	High Similarity	NPC155144

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 NPC291110 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	986
0.2-0.3	1895
0.3-0.4	2699
0.4-0.5	1747
0.5-0.6	957
0.6-0.7	330
0.7-0.8	110
0.8-0.85	29
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.882	High Similarity	NPD3882	Suspended
0.8812	High Similarity	NPD2801	Approved
0.8696	High Similarity	NPD2393	Clinical (unspecified phase)
0.8634	High Similarity	NPD1934	Approved
0.8503	High Similarity	NPD3926	Phase 2
0.8494	Intermediate Similarity	NPD1247	Approved
0.8481	Intermediate Similarity	NPD1511	Approved
0.8462	Intermediate Similarity	NPD3818	Discontinued
0.8434	Intermediate Similarity	NPD5494	Approved
0.8375	Intermediate Similarity	NPD1512	Approved
0.8364	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6166	Phase 2
0.8343	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2344	Approved
0.8266	Intermediate Similarity	NPD6559	Discontinued
0.8155	Intermediate Similarity	NPD919	Approved
0.8125	Intermediate Similarity	NPD2309	Approved
0.8118	Intermediate Similarity	NPD6232	Discontinued
0.8098	Intermediate Similarity	NPD920	Approved
0.8095	Intermediate Similarity	NPD3749	Approved
0.8086	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD3817	Phase 2
0.8081	Intermediate Similarity	NPD7473	Discontinued
0.805	Intermediate Similarity	NPD1549	Phase 2
0.8046	Intermediate Similarity	NPD7074	Phase 3
0.8011	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2800	Approved
0.7989	Intermediate Similarity	NPD7054	Approved
0.7989	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1510	Phase 2
0.7953	Intermediate Similarity	NPD6959	Discontinued
0.7952	Intermediate Similarity	NPD4380	Phase 2
0.7949	Intermediate Similarity	NPD1240	Approved
0.7949	Intermediate Similarity	NPD943	Approved
0.7943	Intermediate Similarity	NPD7472	Approved
0.7925	Intermediate Similarity	NPD2796	Approved
0.7917	Intermediate Similarity	NPD1465	Phase 2
0.7917	Intermediate Similarity	NPD7819	Suspended
0.7914	Intermediate Similarity	NPD6799	Approved
0.7898	Intermediate Similarity	NPD6797	Phase 2
0.7898	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7075	Discontinued
0.7882	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD2532	Approved
0.7866	Intermediate Similarity	NPD2534	Approved
0.7866	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD2533	Approved
0.7853	Intermediate Similarity	NPD7251	Discontinued
0.7853	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1607	Approved
0.7844	Intermediate Similarity	NPD6599	Discontinued
0.7811	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7411	Suspended
0.7785	Intermediate Similarity	NPD230	Phase 1
0.7778	Intermediate Similarity	NPD1243	Approved
0.7765	Intermediate Similarity	NPD5402	Approved
0.7719	Intermediate Similarity	NPD7768	Phase 2
0.7716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7808	Phase 3
0.7702	Intermediate Similarity	NPD1551	Phase 2
0.7702	Intermediate Similarity	NPD2935	Discontinued
0.7654	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6801	Discontinued
0.7637	Intermediate Similarity	NPD8434	Phase 2
0.756	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD2296	Approved
0.7554	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3750	Approved
0.7486	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7199	Phase 2
0.7442	Intermediate Similarity	NPD6280	Approved
0.7442	Intermediate Similarity	NPD6279	Approved
0.744	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD3751	Discontinued
0.7429	Intermediate Similarity	NPD6234	Discontinued
0.7423	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4628	Phase 3
0.741	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD9494	Approved
0.7405	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5953	Discontinued
0.7391	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1613	Approved
0.7375	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3226	Approved
0.736	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5403	Approved
0.7346	Intermediate Similarity	NPD447	Suspended
0.7333	Intermediate Similarity	NPD1471	Phase 3
0.7333	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2799	Discontinued
0.7312	Intermediate Similarity	NPD3027	Phase 3
0.7303	Intermediate Similarity	NPD5710	Approved
0.7303	Intermediate Similarity	NPD6808	Phase 2
0.7303	Intermediate Similarity	NPD5711	Approved
0.7301	Intermediate Similarity	NPD6651	Approved
0.7297	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7286	Phase 2
0.7287	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD6099	Approved
0.7241	Intermediate Similarity	NPD37	Approved
0.7235	Intermediate Similarity	NPD5401	Approved
0.7216	Intermediate Similarity	NPD4966	Approved
0.7216	Intermediate Similarity	NPD4967	Phase 2
0.7216	Intermediate Similarity	NPD4965	Approved
0.7212	Intermediate Similarity	NPD3748	Approved
0.7207	Intermediate Similarity	NPD3787	Discontinued
0.7207	Intermediate Similarity	NPD7229	Phase 3
0.7202	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5760	Phase 2
0.72	Intermediate Similarity	NPD5761	Phase 2
0.7181	Intermediate Similarity	NPD4287	Approved
0.716	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2403	Approved
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.711	Intermediate Similarity	NPD1653	Approved
0.7101	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD9269	Phase 2
0.7085	Intermediate Similarity	NPD8151	Discontinued
0.7081	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5242	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7055	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7041	Intermediate Similarity	NPD2654	Approved
0.7039	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7033	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6782	Approved
0.7026	Intermediate Similarity	NPD6780	Approved
0.7026	Intermediate Similarity	NPD6781	Approved
0.7026	Intermediate Similarity	NPD6778	Approved
0.7026	Intermediate Similarity	NPD6777	Approved
0.7026	Intermediate Similarity	NPD6779	Approved
0.7026	Intermediate Similarity	NPD6776	Approved
0.7005	Intermediate Similarity	NPD8312	Approved
0.7005	Intermediate Similarity	NPD8313	Approved
0.6989	Remote Similarity	NPD7685	Pre-registration
0.6975	Remote Similarity	NPD2861	Phase 2
0.6973	Remote Similarity	NPD1729	Discontinued
0.6957	Remote Similarity	NPD7907	Approved
0.6957	Remote Similarity	NPD2163	Approved
0.6951	Remote Similarity	NPD3764	Approved
0.6949	Remote Similarity	NPD6844	Discontinued
0.6942	Remote Similarity	NPD4665	Approved
0.6942	Remote Similarity	NPD4111	Phase 1
0.6928	Remote Similarity	NPD1933	Approved
0.6919	Remote Similarity	NPD7435	Discontinued
0.6918	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1610	Phase 2
0.6914	Remote Similarity	NPD2798	Approved
0.6907	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4361	Phase 2
0.6905	Remote Similarity	NPD7033	Discontinued
0.6884	Remote Similarity	NPD7870	Phase 2
0.6884	Remote Similarity	NPD7871	Phase 2
0.6875	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9717	Approved
0.6875	Remote Similarity	NPD3972	Approved
0.6875	Remote Similarity	NPD1608	Approved
0.6872	Remote Similarity	NPD5353	Approved
0.6872	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD4360	Phase 2
0.6856	Remote Similarity	NPD4363	Phase 3
0.6852	Remote Similarity	NPD1470	Approved
0.6848	Remote Similarity	NPD3268	Approved
0.6847	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7783	Phase 2
0.6839	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD9268	Approved
0.6834	Remote Similarity	NPD7697	Approved
0.6834	Remote Similarity	NPD7696	Phase 3
0.6834	Remote Similarity	NPD7698	Approved
0.6826	Remote Similarity	NPD6355	Discontinued
0.6807	Remote Similarity	NPD6233	Phase 2
0.6806	Remote Similarity	NPD8150	Discontinued
0.6798	Remote Similarity	NPD6386	Approved
0.6798	Remote Similarity	NPD6385	Approved
0.679	Remote Similarity	NPD1876	Approved
0.6788	Remote Similarity	NPD4625	Phase 3
0.6782	Remote Similarity	NPD7701	Phase 2
0.6782	Remote Similarity	NPD4357	Discontinued

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