NPASS Compound

Structure

CID99591 OpenBabel06191715442D 51 56 0 0 0 0 0 0 0 0999 V2000 -1.7017 5.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1050 0.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9558 0.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4033 -2.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2542 6.3860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7017 -2.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7017 5.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 4.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5525 -0.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7017 0.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 6.3860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.9123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4033 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5525 1.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7017 0.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7017 4.9123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7017 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4033 0.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4033 1.9649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7017 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2542 3.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 -1.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2542 1.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5525 -0.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1050 2.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7017 -1.9649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2542 4.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5525 4.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 -0.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4033 2.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 -0.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1050 1.9649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5525 -1.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4033 4.9123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 -1.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2542 0.4912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4033 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9558 3.4386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7017 -2.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1050 4.9123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 6.3860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2542 1.4737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9558 1.4737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4033 -1.9649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4033 5.8947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7017 -1.9649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5525 3.4386 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 44 1 0 0 0 0 2 45 1 0 0 0 0 3 46 1 0 0 0 0 4 47 1 0 0 0 0 5 48 1 0 0 0 0 6 49 1 0 0 0 0 7 11 1 0 0 0 0 7 16 2 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 17 2 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 44 1 0 0 0 0 19 45 1 0 0 0 0 20 24 1 0 0 0 0 20 32 2 0 0 0 0 21 25 1 0 0 0 0 21 33 2 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 22 32 1 0 0 0 0 23 27 2 0 0 0 0 23 29 1 0 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 24 38 1 0 0 0 0 25 35 2 0 0 0 0 25 39 1 0 0 0 0 26 34 1 0 0 0 0 26 40 1 0 0 0 0 27 35 1 0 0 0 0 27 41 1 0 0 0 0 28 36 1 0 0 0 0 28 42 2 0 0 0 0 29 37 1 0 0 0 0 29 43 2 0 0 0 0 30 36 2 0 0 0 0 30 50 1 0 0 0 0 31 37 2 0 0 0 0 31 51 1 0 0 0 0 32 50 1 0 0 0 0 33 51 1 0 0 0 0 34 46 1 0 0 0 0 35 47 1 0 0 0 0 36 48 1 0 0 0 0 37 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	700.18
Volume:	678.049
LogP:	5.473
LogD:	2.435
LogS:	-3.696
# Rotatable Bonds:	10
TPSA:	196.72
# H-Bond Aceptor:	14
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.136
Synthetic Accessibility Score:	3.234
Fsp3:	0.189
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.097
MDCK Permeability:	2.7266049073659815e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.231
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	83.63459777832031%
Volume Distribution (VD):	0.323
Pgp-substrate:	44.6328010559082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.198
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.829
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.332
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.398

ADMET: Excretion

Clearance (CL):	1.272
Half-life (T1/2):	0.394

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.996
AMES Toxicity:	0.324
Rat Oral Acute Toxicity:	0.5
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.66
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.388
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC99591

Natural Product ID:	NPC99591
*Common Name:**	Methylenebissantin
IUPAC Name:	8-[[5,7-dihydroxy-3,6-dimethoxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]methyl]-5,7-dihydroxy-3,6-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms:	Methylenebissantin
Standard InCHIKey:	PCEQWQQXZCRNCK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C37H32O14/c1-44-18-11-7-16(8-12-18)30-36(48-5)28(42)22-26(40)34(46-3)24(38)20(32(22)50-30)15-21-25(39)35(47-4)27(41)23-29(43)37(49-6)31(51-33(21)23)17-9-13-19(45-2)14-10-17/h7-14,38-41H,15H2,1-6H3
SMILES:	COc1ccc(cc1)c1c(c(=O)c2c(c(c(c(Cc3c(c(c(c4c(=O)c(c(c5ccc(cc5)OC)oc34)OC)O)OC)O)c2o1)O)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1933858
PubChem CID:	56835122
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002591] 6-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
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620239]
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5452	Curcuma parviflora	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3010	Nidorella hottentotica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26259	Streptomyces rimofaciens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16448	Corydalis pseudoadunca	Species	Papaveraceae	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
NPT1333	Individual Protein	Enoyl-acyl-carrier protein reductase	Plasmodium falciparum	IC50	=	91130.0	nM	PMID[522888]

☑ 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 NPC99591 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	489
0.1-0.2	2123
0.2-0.3	5317
0.3-0.4	11320
0.4-0.5	6032
0.5-0.6	4193
0.6-0.7	5385
0.7-0.8	4508
0.8-0.85	1688
0.85-0.9	1287
0.9-0.95	350
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9506	High Similarity	NPC272064
0.9383	High Similarity	NPC196179
0.9383	High Similarity	NPC34089
0.9345	High Similarity	NPC216307
0.9329	High Similarity	NPC259757
0.9321	High Similarity	NPC246478
0.9277	High Similarity	NPC475212
0.9273	High Similarity	NPC470462
0.9268	High Similarity	NPC470459
0.9259	High Similarity	NPC9609
0.9259	High Similarity	NPC25495
0.9259	High Similarity	NPC261004
0.9259	High Similarity	NPC19687
0.9259	High Similarity	NPC18607
0.9259	High Similarity	NPC143828
0.9259	High Similarity	NPC176300
0.9259	High Similarity	NPC253634
0.9259	High Similarity	NPC105242
0.9259	High Similarity	NPC22472
0.9259	High Similarity	NPC130894
0.9259	High Similarity	NPC152166
0.9259	High Similarity	NPC204854
0.9259	High Similarity	NPC7846
0.9259	High Similarity	NPC300943
0.9259	High Similarity	NPC288669
0.9259	High Similarity	NPC191459
0.9259	High Similarity	NPC4481
0.9259	High Similarity	NPC18772
0.9259	High Similarity	NPC115798
0.9235	High Similarity	NPC324742
0.9217	High Similarity	NPC470456
0.9217	High Similarity	NPC295082
0.9217	High Similarity	NPC158761
0.9212	High Similarity	NPC470457
0.9202	High Similarity	NPC188967
0.9198	High Similarity	NPC203891
0.9198	High Similarity	NPC112954
0.9198	High Similarity	NPC305663
0.9198	High Similarity	NPC101830
0.9198	High Similarity	NPC78302
0.9198	High Similarity	NPC287979
0.9198	High Similarity	NPC163524
0.9198	High Similarity	NPC75215
0.9198	High Similarity	NPC472438
0.9198	High Similarity	NPC110070
0.9198	High Similarity	NPC176665
0.9198	High Similarity	NPC224137
0.9198	High Similarity	NPC189179
0.9198	High Similarity	NPC29841
0.9198	High Similarity	NPC93376
0.9198	High Similarity	NPC235215
0.9198	High Similarity	NPC183
0.9198	High Similarity	NPC227192
0.9198	High Similarity	NPC7973
0.9167	High Similarity	NPC476370
0.9162	High Similarity	NPC280493
0.9162	High Similarity	NPC107627
0.9157	High Similarity	NPC272560
0.9146	High Similarity	NPC259456
0.9141	High Similarity	NPC154304
0.9141	High Similarity	NPC190487
0.9141	High Similarity	NPC193842
0.9136	High Similarity	NPC49824
0.9136	High Similarity	NPC98661
0.9136	High Similarity	NPC43243
0.9136	High Similarity	NPC247017
0.9136	High Similarity	NPC178854
0.9136	High Similarity	NPC268161
0.9136	High Similarity	NPC292107
0.9136	High Similarity	NPC266960
0.9136	High Similarity	NPC245546
0.9136	High Similarity	NPC200388
0.9136	High Similarity	NPC100916
0.9136	High Similarity	NPC55619
0.9136	High Similarity	NPC474520
0.9112	High Similarity	NPC476374
0.9102	High Similarity	NPC243877
0.9102	High Similarity	NPC260266
0.9096	High Similarity	NPC477840
0.9096	High Similarity	NPC50960
0.9091	High Similarity	NPC83922
0.9091	High Similarity	NPC261470
0.9091	High Similarity	NPC472448
0.9091	High Similarity	NPC219927
0.9085	High Similarity	NPC204290
0.9085	High Similarity	NPC476980
0.908	High Similarity	NPC218871
0.908	High Similarity	NPC64755
0.908	High Similarity	NPC237418
0.908	High Similarity	NPC78225
0.908	High Similarity	NPC476630
0.908	High Similarity	NPC185526
0.9074	High Similarity	NPC167815
0.9074	High Similarity	NPC92659
0.9074	High Similarity	NPC227325
0.9074	High Similarity	NPC189960
0.9074	High Similarity	NPC201136
0.9074	High Similarity	NPC44079
0.9074	High Similarity	NPC146165
0.9074	High Similarity	NPC2476
0.9074	High Similarity	NPC26227
0.9074	High Similarity	NPC32557
0.9074	High Similarity	NPC128863
0.9074	High Similarity	NPC138360
0.9074	High Similarity	NPC280339
0.9074	High Similarity	NPC50715
0.9074	High Similarity	NPC183597
0.9074	High Similarity	NPC133392
0.9074	High Similarity	NPC196439
0.9074	High Similarity	NPC214138
0.9074	High Similarity	NPC163780
0.9074	High Similarity	NPC201451
0.9074	High Similarity	NPC4455
0.9053	High Similarity	NPC472454
0.9053	High Similarity	NPC186847
0.9053	High Similarity	NPC257667
0.9048	High Similarity	NPC177480
0.9042	High Similarity	NPC320741
0.9042	High Similarity	NPC171985
0.9042	High Similarity	NPC39091
0.9036	High Similarity	NPC41301
0.903	High Similarity	NPC167678
0.903	High Similarity	NPC29876
0.903	High Similarity	NPC258331
0.903	High Similarity	NPC198829
0.903	High Similarity	NPC40037
0.903	High Similarity	NPC266314
0.9024	High Similarity	NPC469658
0.9018	High Similarity	NPC265511
0.9018	High Similarity	NPC191146
0.9018	High Similarity	NPC276444
0.9018	High Similarity	NPC471985
0.9018	High Similarity	NPC68093
0.9017	High Similarity	NPC150977
0.9012	High Similarity	NPC476631
0.9012	High Similarity	NPC236223
0.9012	High Similarity	NPC231018
0.9012	High Similarity	NPC176775
0.9012	High Similarity	NPC274327
0.9012	High Similarity	NPC183878
0.9012	High Similarity	NPC276409
0.9012	High Similarity	NPC145379
0.9012	High Similarity	NPC162351
0.9012	High Similarity	NPC185275
0.9012	High Similarity	NPC246204
0.9012	High Similarity	NPC255350
0.9012	High Similarity	NPC75279
0.9012	High Similarity	NPC160951
0.9012	High Similarity	NPC179126
0.9012	High Similarity	NPC78326
0.9012	High Similarity	NPC270620
0.9012	High Similarity	NPC58382
0.9012	High Similarity	NPC47781
0.9012	High Similarity	NPC86485
0.9012	High Similarity	NPC250822
0.9012	High Similarity	NPC22519
0.9012	High Similarity	NPC69394
0.9006	High Similarity	NPC49667
0.9006	High Similarity	NPC8127
0.9	High Similarity	NPC149846
0.8994	High Similarity	NPC476365
0.8988	High Similarity	NPC14662
0.8982	High Similarity	NPC7688
0.8982	High Similarity	NPC36
0.8982	High Similarity	NPC472450
0.8982	High Similarity	NPC239752
0.8982	High Similarity	NPC275780
0.8982	High Similarity	NPC72787
0.8982	High Similarity	NPC36916
0.8982	High Similarity	NPC7154
0.8982	High Similarity	NPC125039
0.8982	High Similarity	NPC280893
0.8982	High Similarity	NPC58223
0.8976	High Similarity	NPC194427
0.8976	High Similarity	NPC477841
0.8976	High Similarity	NPC78332
0.8966	High Similarity	NPC148710
0.8963	High Similarity	NPC476981
0.8963	High Similarity	NPC262286
0.8963	High Similarity	NPC36852
0.8957	High Similarity	NPC208197
0.8957	High Similarity	NPC256612
0.8957	High Similarity	NPC213622
0.8957	High Similarity	NPC20830
0.8953	High Similarity	NPC265380
0.8953	High Similarity	NPC168584
0.8951	High Similarity	NPC222830
0.8951	High Similarity	NPC198826
0.8951	High Similarity	NPC57030
0.8951	High Similarity	NPC120163
0.8951	High Similarity	NPC82325
0.8951	High Similarity	NPC212678
0.8951	High Similarity	NPC63187
0.8951	High Similarity	NPC293183
0.8951	High Similarity	NPC256283
0.8951	High Similarity	NPC249570
0.8951	High Similarity	NPC27208
0.8951	High Similarity	NPC279989
0.8951	High Similarity	NPC123886
0.8951	High Similarity	NPC239128

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 NPC99591 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	1036
0.2-0.3	1996
0.3-0.4	2726
0.4-0.5	1656
0.5-0.6	871
0.6-0.7	264
0.7-0.8	105
0.8-0.85	24
0.85-0.9	20
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9012	High Similarity	NPD2801	Approved
0.8982	High Similarity	NPD6166	Phase 2
0.8982	High Similarity	NPD6167	Clinical (unspecified phase)
0.8982	High Similarity	NPD6168	Clinical (unspecified phase)
0.8675	High Similarity	NPD3882	Suspended
0.8667	High Similarity	NPD2393	Clinical (unspecified phase)
0.8621	High Similarity	NPD4338	Clinical (unspecified phase)
0.8621	High Similarity	NPD7808	Phase 3
0.8614	High Similarity	NPD3817	Phase 2
0.8606	High Similarity	NPD1934	Approved
0.858	High Similarity	NPD1512	Approved
0.8563	High Similarity	NPD7251	Discontinued
0.8519	High Similarity	NPD4378	Clinical (unspecified phase)
0.8506	High Similarity	NPD6797	Phase 2
0.8506	High Similarity	NPD7993	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD7054	Approved
0.8457	Intermediate Similarity	NPD1511	Approved
0.8448	Intermediate Similarity	NPD7472	Approved
0.8448	Intermediate Similarity	NPD7074	Phase 3
0.8402	Intermediate Similarity	NPD7075	Discontinued
0.8382	Intermediate Similarity	NPD7473	Discontinued
0.8343	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8314	Intermediate Similarity	NPD6232	Discontinued
0.8304	Intermediate Similarity	NPD5494	Approved
0.8293	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD5402	Approved
0.8263	Intermediate Similarity	NPD4380	Phase 2
0.8256	Intermediate Similarity	NPD6959	Discontinued
0.8232	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD6801	Discontinued
0.815	Intermediate Similarity	NPD1247	Approved
0.8114	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD5844	Phase 1
0.8043	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7768	Phase 2
0.8012	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD7411	Suspended
0.7977	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6799	Approved
0.787	Intermediate Similarity	NPD5403	Approved
0.7853	Intermediate Similarity	NPD3926	Phase 2
0.7829	Intermediate Similarity	NPD919	Approved
0.7803	Intermediate Similarity	NPD1465	Phase 2
0.7758	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD5401	Approved
0.7744	Intermediate Similarity	NPD1510	Phase 2
0.7733	Intermediate Similarity	NPD6599	Discontinued
0.7711	Intermediate Similarity	NPD1549	Phase 2
0.7697	Intermediate Similarity	NPD2796	Approved
0.7692	Intermediate Similarity	NPD7390	Discontinued
0.7684	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD8312	Approved
0.7663	Intermediate Similarity	NPD8313	Approved
0.765	Intermediate Similarity	NPD6559	Discontinued
0.7607	Intermediate Similarity	NPD1240	Approved
0.7607	Intermediate Similarity	NPD943	Approved
0.7598	Intermediate Similarity	NPD3787	Discontinued
0.759	Intermediate Similarity	NPD2935	Discontinued
0.7571	Intermediate Similarity	NPD3749	Approved
0.7558	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7435	Discontinued
0.7527	Intermediate Similarity	NPD3751	Discontinued
0.7515	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD7870	Phase 2
0.75	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD6778	Approved
0.7474	Intermediate Similarity	NPD6779	Approved
0.7474	Intermediate Similarity	NPD6781	Approved
0.7474	Intermediate Similarity	NPD6780	Approved
0.7474	Intermediate Similarity	NPD6782	Approved
0.7474	Intermediate Similarity	NPD6776	Approved
0.7474	Intermediate Similarity	NPD6777	Approved
0.7471	Intermediate Similarity	NPD6190	Approved
0.7456	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2800	Approved
0.7449	Intermediate Similarity	NPD7696	Phase 3
0.7449	Intermediate Similarity	NPD7697	Approved
0.7449	Intermediate Similarity	NPD7698	Approved
0.7447	Intermediate Similarity	NPD8150	Discontinued
0.7442	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3750	Approved
0.74	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7874	Approved
0.7396	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7701	Phase 2
0.7385	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3226	Approved
0.7362	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD8151	Discontinued
0.7348	Intermediate Similarity	NPD7199	Phase 2
0.7341	Intermediate Similarity	NPD2534	Approved
0.7341	Intermediate Similarity	NPD2532	Approved
0.7341	Intermediate Similarity	NPD2533	Approved
0.7337	Intermediate Similarity	NPD7228	Approved
0.7333	Intermediate Similarity	NPD6234	Discontinued
0.7321	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6651	Approved
0.7303	Intermediate Similarity	NPD8455	Phase 2
0.7301	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1613	Approved
0.7289	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7699	Phase 2
0.7282	Intermediate Similarity	NPD7700	Phase 2
0.7277	Intermediate Similarity	NPD7801	Approved
0.7277	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7783	Phase 2
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7257	Intermediate Similarity	NPD920	Approved
0.7246	Intermediate Similarity	NPD447	Suspended
0.7246	Intermediate Similarity	NPD230	Phase 1
0.7219	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5953	Discontinued
0.7216	Intermediate Similarity	NPD6535	Approved
0.7216	Intermediate Similarity	NPD6534	Approved
0.7216	Intermediate Similarity	NPD1653	Approved
0.7212	Intermediate Similarity	NPD3027	Phase 3
0.7204	Intermediate Similarity	NPD7286	Phase 2
0.7181	Intermediate Similarity	NPD7685	Pre-registration
0.7169	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2313	Discontinued
0.7169	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD37	Approved
0.7151	Intermediate Similarity	NPD1243	Approved
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6823	Phase 2
0.7135	Intermediate Similarity	NPD2344	Approved
0.7135	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4965	Approved
0.7127	Intermediate Similarity	NPD4967	Phase 2
0.7127	Intermediate Similarity	NPD4966	Approved
0.7126	Intermediate Similarity	NPD6233	Phase 2
0.7118	Intermediate Similarity	NPD2799	Discontinued
0.7118	Intermediate Similarity	NPD3748	Approved
0.7079	Intermediate Similarity	NPD7458	Discontinued
0.7076	Intermediate Similarity	NPD1551	Phase 2
0.7076	Intermediate Similarity	NPD6099	Approved
0.7076	Intermediate Similarity	NPD6100	Approved
0.7066	Intermediate Similarity	NPD6798	Discontinued
0.7065	Intermediate Similarity	NPD8319	Approved
0.7065	Intermediate Similarity	NPD8320	Phase 1
0.7048	Intermediate Similarity	NPD4908	Phase 1
0.7035	Intermediate Similarity	NPD2346	Discontinued
0.7029	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7229	Phase 3
0.7011	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4628	Phase 3
0.6995	Remote Similarity	NPD7584	Approved
0.6988	Remote Similarity	NPD9494	Approved
0.6977	Remote Similarity	NPD5408	Approved
0.6977	Remote Similarity	NPD5404	Approved
0.6977	Remote Similarity	NPD5406	Approved
0.6977	Remote Similarity	NPD5405	Approved
0.6973	Remote Similarity	NPD8127	Discontinued
0.6971	Remote Similarity	NPD2309	Approved
0.6967	Remote Similarity	NPD7907	Approved
0.6963	Remote Similarity	NPD7549	Discontinued
0.6961	Remote Similarity	NPD6844	Discontinued
0.6954	Remote Similarity	NPD4360	Phase 2
0.6954	Remote Similarity	NPD4363	Phase 3
0.6952	Remote Similarity	NPD2403	Approved
0.6951	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1933	Approved
0.6914	Remote Similarity	NPD8166	Discontinued
0.6914	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7240	Approved
0.6882	Remote Similarity	NPD4060	Phase 1
0.6854	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5710	Approved
0.6845	Remote Similarity	NPD6832	Phase 2
0.6845	Remote Similarity	NPD5711	Approved
0.6842	Remote Similarity	NPD6355	Discontinued
0.6832	Remote Similarity	NPD2493	Approved
0.6832	Remote Similarity	NPD2494	Approved
0.6818	Remote Similarity	NPD6213	Phase 3
0.6818	Remote Similarity	NPD7003	Approved
0.6818	Remote Similarity	NPD6212	Phase 3
0.6818	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5242	Approved
0.6805	Remote Similarity	NPD7095	Approved
0.6804	Remote Similarity	NPD8054	Approved
0.6804	Remote Similarity	NPD8053	Approved
0.6796	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7177	Discontinued
0.678	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1203	Approved
0.6765	Remote Similarity	NPD7680	Approved
0.6765	Remote Similarity	NPD3268	Approved
0.6751	Remote Similarity	NPD4287	Approved
0.675	Remote Similarity	NPD4362	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data