NPASS Compound

Structure

NPC469600 OpenBabel07101719522D 37 41 0 0 1 0 0 0 0 0999 V2000 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6010 -4.0000 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 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 2 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 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 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 -1.7321 -3.0000 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 -2.5981 -3.5000 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 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 -3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 -4.8090 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 3 2 0 0 0 0 2 11 1 0 0 0 0 3 14 1 0 0 0 0 4 11 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 13 1 0 0 0 0 6 26 2 0 0 0 0 7 27 1 0 0 0 0 8 12 1 0 0 0 0 8 33 1 0 0 0 0 9 34 1 0 0 0 0 9 35 1 0 0 0 0 10 18 2 0 0 0 0 10 23 1 0 0 0 0 12 4 1 1 0 0 0 12 19 1 0 0 0 0 13 23 2 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 34 1 0 0 0 0 15 35 1 0 0 0 0 16 7 1 6 0 0 0 16 20 1 0 0 0 0 16 36 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 28 1 0 0 0 0 19 29 2 0 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 22 1 0 0 0 0 21 31 1 6 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 37 1 0 0 0 0 24 33 1 0 0 0 0 25 36 1 0 0 0 0 25 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	518.14
Volume:	482.565
LogP:	1.411
LogD:	0.626
LogS:	-4.22
# Rotatable Bonds:	6
TPSA:	181.44
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	4.506
Fsp3:	0.44
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.979
MDCK Permeability:	7.69548842072254e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.08

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	99.20709991455078%
Volume Distribution (VD):	0.723
Pgp-substrate:	1.5964875221252441%

ADMET: Metabolism

CYP1A2-inhibitor:	0.172
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.409
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.28
CYP2D6-inhibitor:	0.742
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.787
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	6.299
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.446
AMES Toxicity:	0.454
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.277
Carcinogencity:	0.857
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC469600

Natural Product ID:	NPC469600
*Common Name:**	Ophiopogoside A
IUPAC Name:	(3R)-3-(1,3-benzodioxol-5-ylmethyl)-5-hydroxy-6-methyl-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromene-8-carbaldehyde
Synonyms:
Standard InCHIKey:	OBMSIXVTKJATDI-QXRDVXQNSA-N
Standard InCHI:	InChI=1S/C25H26O12/c1-10-18(28)17-19(29)12(4-11-2-3-14-15(5-11)35-9-34-14)8-33-24(17)13(6-26)23(10)37-25-22(32)21(31)20(30)16(7-27)36-25/h2-3,5-6,12,16,20-22,25,27-28,30-32H,4,7-9H2,1H3/t12-,16-,20-,21+,22-,25+/m1/s1
SMILES:	CC1=C(C2=C(C(=C1OC3C(C(C(C(O3)CO)O)O)O)C=O)OCC(C2=O)CC4=CC5=C(C=C4)OCO5)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1093535
PubChem CID:	46865651
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans [CHEMONTID:0002898] Homoisoflavanones

*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
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	roots	n.a.	n.a.	PMID[20346658]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23439553]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	tuber	n.a.	Database[Article]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9261	Ophiopogon japonicus	Species	Asparagaceae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	28.5	pg/ml	PMID[460790]

☑ 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 NPC469600 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	1641
0.2-0.3	3577
0.3-0.4	8786
0.4-0.5	9517
0.5-0.6	4223
0.6-0.7	4987
0.7-0.8	6075
0.8-0.85	2605
0.85-0.9	799
0.9-0.95	66
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC469601
0.9455	High Similarity	NPC477502
0.9401	High Similarity	NPC256760
0.9401	High Similarity	NPC261254
0.9394	High Similarity	NPC5778
0.9394	High Similarity	NPC236934
0.9345	High Similarity	NPC208668
0.9341	High Similarity	NPC78734
0.9341	High Similarity	NPC150767
0.9329	High Similarity	NPC125991
0.929	High Similarity	NPC472607
0.9286	High Similarity	NPC235575
0.9281	High Similarity	NPC472381
0.9281	High Similarity	NPC293629
0.9281	High Similarity	NPC472383
0.9281	High Similarity	NPC229687
0.9273	High Similarity	NPC309025
0.9273	High Similarity	NPC29830
0.9273	High Similarity	NPC243930
0.9273	High Similarity	NPC88023
0.9226	High Similarity	NPC212748
0.9226	High Similarity	NPC218488
0.9226	High Similarity	NPC177731
0.9226	High Similarity	NPC21190
0.9226	High Similarity	NPC51326
0.9226	High Similarity	NPC79056
0.9226	High Similarity	NPC105095
0.9226	High Similarity	NPC183357
0.9226	High Similarity	NPC22195
0.9226	High Similarity	NPC231194
0.9226	High Similarity	NPC44558
0.9226	High Similarity	NPC44328
0.9222	High Similarity	NPC45400
0.9222	High Similarity	NPC93099
0.9222	High Similarity	NPC229729
0.9217	High Similarity	NPC22832
0.9217	High Similarity	NPC311830
0.9212	High Similarity	NPC127782
0.9212	High Similarity	NPC300537
0.9181	High Similarity	NPC241196
0.9176	High Similarity	NPC294629
0.9176	High Similarity	NPC108202
0.9172	High Similarity	NPC267254
0.9172	High Similarity	NPC472386
0.9167	High Similarity	NPC95855
0.9167	High Similarity	NPC210042
0.9167	High Similarity	NPC195257
0.9167	High Similarity	NPC52382
0.9167	High Similarity	NPC112755
0.9167	High Similarity	NPC209296
0.9167	High Similarity	NPC270578
0.9167	High Similarity	NPC43587
0.9167	High Similarity	NPC471457
0.9167	High Similarity	NPC170675
0.9162	High Similarity	NPC210073
0.9162	High Similarity	NPC115674
0.9157	High Similarity	NPC191306
0.9157	High Similarity	NPC19709
0.9157	High Similarity	NPC222936
0.9157	High Similarity	NPC284960
0.9157	High Similarity	NPC270335
0.9152	High Similarity	NPC182045
0.9133	High Similarity	NPC473883
0.9123	High Similarity	NPC255799
0.9118	High Similarity	NPC51774
0.9118	High Similarity	NPC236191
0.9118	High Similarity	NPC25724
0.9118	High Similarity	NPC239549
0.9112	High Similarity	NPC474434
0.9112	High Similarity	NPC105511
0.9112	High Similarity	NPC34287
0.9112	High Similarity	NPC471416
0.9107	High Similarity	NPC92565
0.9107	High Similarity	NPC160156
0.9102	High Similarity	NPC165720
0.9102	High Similarity	NPC475497
0.9102	High Similarity	NPC475366
0.9102	High Similarity	NPC284277
0.9096	High Similarity	NPC259834
0.9096	High Similarity	NPC472635
0.9096	High Similarity	NPC473043
0.9096	High Similarity	NPC77660
0.9096	High Similarity	NPC189142
0.9096	High Similarity	NPC44947
0.9091	High Similarity	NPC472320
0.9091	High Similarity	NPC110349
0.907	High Similarity	NPC168584
0.9064	High Similarity	NPC102028
0.9059	High Similarity	NPC205076
0.9059	High Similarity	NPC223375
0.9059	High Similarity	NPC245452
0.9059	High Similarity	NPC307518
0.9059	High Similarity	NPC475825
0.9059	High Similarity	NPC48773
0.9059	High Similarity	NPC156977
0.9059	High Similarity	NPC301683
0.9053	High Similarity	NPC183036
0.9053	High Similarity	NPC58053
0.9053	High Similarity	NPC186807
0.9053	High Similarity	NPC201292
0.9053	High Similarity	NPC226294
0.9053	High Similarity	NPC61791
0.9053	High Similarity	NPC203050
0.9053	High Similarity	NPC105283
0.9053	High Similarity	NPC105025
0.9053	High Similarity	NPC223747
0.9053	High Similarity	NPC86008
0.9053	High Similarity	NPC225434
0.9053	High Similarity	NPC93337
0.9053	High Similarity	NPC475942
0.9053	High Similarity	NPC120099
0.9053	High Similarity	NPC469931
0.9053	High Similarity	NPC45638
0.9053	High Similarity	NPC219904
0.9048	High Similarity	NPC197285
0.9048	High Similarity	NPC254306
0.9048	High Similarity	NPC21100
0.9048	High Similarity	NPC8856
0.9042	High Similarity	NPC88043
0.9042	High Similarity	NPC257566
0.9042	High Similarity	NPC124155
0.9042	High Similarity	NPC168822
0.9036	High Similarity	NPC47923
0.9036	High Similarity	NPC26326
0.9036	High Similarity	NPC472632
0.903	High Similarity	NPC473990
0.903	High Similarity	NPC308265
0.9024	High Similarity	NPC206378
0.9024	High Similarity	NPC155063
0.9012	High Similarity	NPC472384
0.9012	High Similarity	NPC472380
0.9012	High Similarity	NPC472382
0.9012	High Similarity	NPC156635
0.9006	High Similarity	NPC204693
0.9	High Similarity	NPC279209
0.9	High Similarity	NPC102277
0.9	High Similarity	NPC285197
0.9	High Similarity	NPC72249
0.9	High Similarity	NPC293004
0.9	High Similarity	NPC206123
0.9	High Similarity	NPC67105
0.9	High Similarity	NPC95866
0.9	High Similarity	NPC224462
0.8994	High Similarity	NPC84362
0.8994	High Similarity	NPC149244
0.8994	High Similarity	NPC116745
0.8994	High Similarity	NPC45618
0.8994	High Similarity	NPC226304
0.8994	High Similarity	NPC265530
0.8994	High Similarity	NPC127546
0.8994	High Similarity	NPC52550
0.8994	High Similarity	NPC146792
0.8994	High Similarity	NPC135345
0.8994	High Similarity	NPC325555
0.8994	High Similarity	NPC317489
0.8994	High Similarity	NPC223424
0.8994	High Similarity	NPC173637
0.8994	High Similarity	NPC48640
0.8994	High Similarity	NPC58716
0.8988	High Similarity	NPC470773
0.8988	High Similarity	NPC277205
0.8988	High Similarity	NPC15358
0.8982	High Similarity	NPC474034
0.8982	High Similarity	NPC474033
0.8982	High Similarity	NPC190450
0.8982	High Similarity	NPC148273
0.8982	High Similarity	NPC131745
0.8976	High Similarity	NPC475784
0.8976	High Similarity	NPC472624
0.8976	High Similarity	NPC200708
0.8976	High Similarity	NPC174953
0.8976	High Similarity	NPC271479
0.8971	High Similarity	NPC148710
0.897	High Similarity	NPC474055
0.897	High Similarity	NPC472598
0.897	High Similarity	NPC23817
0.897	High Similarity	NPC470606
0.8966	High Similarity	NPC473073
0.8966	High Similarity	NPC473071
0.8963	High Similarity	NPC72649
0.8963	High Similarity	NPC39351
0.8963	High Similarity	NPC26195
0.8963	High Similarity	NPC97052
0.8963	High Similarity	NPC169248
0.896	High Similarity	NPC472387
0.8953	High Similarity	NPC474345
0.8953	High Similarity	NPC19108
0.8953	High Similarity	NPC473327
0.8953	High Similarity	NPC294815
0.8953	High Similarity	NPC142996
0.8953	High Similarity	NPC16194
0.8953	High Similarity	NPC220173
0.8953	High Similarity	NPC198199
0.8953	High Similarity	NPC476472
0.8947	High Similarity	NPC117260
0.8947	High Similarity	NPC60735
0.8947	High Similarity	NPC67134
0.8947	High Similarity	NPC47140
0.8947	High Similarity	NPC26230
0.8947	High Similarity	NPC153755

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 NPC469600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	902
0.2-0.3	1861
0.3-0.4	2650
0.4-0.5	1863
0.5-0.6	957
0.6-0.7	367
0.7-0.8	145
0.8-0.85	22
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9226	High Similarity	NPD7074	Phase 3
0.9167	High Similarity	NPD7054	Approved
0.9112	High Similarity	NPD7472	Approved
0.9107	High Similarity	NPD3818	Discontinued
0.8953	High Similarity	NPD7808	Phase 3
0.8947	High Similarity	NPD6797	Phase 2
0.8895	High Similarity	NPD6559	Discontinued
0.8895	High Similarity	NPD7251	Discontinued
0.8855	High Similarity	NPD4381	Clinical (unspecified phase)
0.883	High Similarity	NPD7804	Clinical (unspecified phase)
0.8788	High Similarity	NPD2393	Clinical (unspecified phase)
0.8765	High Similarity	NPD6166	Phase 2
0.8765	High Similarity	NPD6168	Clinical (unspecified phase)
0.8765	High Similarity	NPD6167	Clinical (unspecified phase)
0.8736	High Similarity	NPD4338	Clinical (unspecified phase)
0.8727	High Similarity	NPD1934	Approved
0.8639	High Similarity	NPD5494	Approved
0.8494	Intermediate Similarity	NPD4380	Phase 2
0.8402	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD3882	Suspended
0.8343	Intermediate Similarity	NPD2801	Approved
0.8304	Intermediate Similarity	NPD7075	Discontinued
0.8294	Intermediate Similarity	NPD3817	Phase 2
0.8246	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7411	Suspended
0.8136	Intermediate Similarity	NPD7228	Approved
0.8133	Intermediate Similarity	NPD1511	Approved
0.8129	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD5844	Phase 1
0.8084	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7473	Discontinued
0.807	Intermediate Similarity	NPD6801	Discontinued
0.8057	Intermediate Similarity	NPD1247	Approved
0.8057	Intermediate Similarity	NPD7199	Phase 2
0.8057	Intermediate Similarity	NPD6959	Discontinued
0.8036	Intermediate Similarity	NPD1512	Approved
0.8023	Intermediate Similarity	NPD7819	Suspended
0.8011	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD8313	Approved
0.7967	Intermediate Similarity	NPD8312	Approved
0.7965	Intermediate Similarity	NPD37	Approved
0.7943	Intermediate Similarity	NPD6234	Discontinued
0.7943	Intermediate Similarity	NPD919	Approved
0.7939	Intermediate Similarity	NPD1549	Phase 2
0.7931	Intermediate Similarity	NPD4965	Approved
0.7931	Intermediate Similarity	NPD4967	Phase 2
0.7931	Intermediate Similarity	NPD4966	Approved
0.7921	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD1465	Phase 2
0.7784	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5402	Approved
0.776	Intermediate Similarity	NPD7240	Approved
0.776	Intermediate Similarity	NPD7685	Pre-registration
0.7733	Intermediate Similarity	NPD1653	Approved
0.7711	Intermediate Similarity	NPD2796	Approved
0.7706	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6799	Approved
0.7674	Intermediate Similarity	NPD5403	Approved
0.766	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1510	Phase 2
0.7626	Intermediate Similarity	NPD8151	Discontinued
0.7614	Intermediate Similarity	NPD7584	Approved
0.7614	Intermediate Similarity	NPD8455	Phase 2
0.7577	Intermediate Similarity	NPD6778	Approved
0.7577	Intermediate Similarity	NPD6779	Approved
0.7577	Intermediate Similarity	NPD6781	Approved
0.7577	Intermediate Similarity	NPD6782	Approved
0.7577	Intermediate Similarity	NPD6780	Approved
0.7577	Intermediate Similarity	NPD6777	Approved
0.7577	Intermediate Similarity	NPD6776	Approved
0.7574	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD920	Approved
0.7569	Intermediate Similarity	NPD3926	Phase 2
0.7558	Intermediate Similarity	NPD5401	Approved
0.7558	Intermediate Similarity	NPD2533	Approved
0.7558	Intermediate Similarity	NPD2534	Approved
0.7558	Intermediate Similarity	NPD2532	Approved
0.7553	Intermediate Similarity	NPD8434	Phase 2
0.7543	Intermediate Similarity	NPD6599	Discontinued
0.7541	Intermediate Similarity	NPD3751	Discontinued
0.7528	Intermediate Similarity	NPD7768	Phase 2
0.7515	Intermediate Similarity	NPD1240	Approved
0.7515	Intermediate Similarity	NPD1613	Approved
0.7515	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD3787	Discontinued
0.7487	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3749	Approved
0.7471	Intermediate Similarity	NPD2800	Approved
0.7463	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7783	Phase 2
0.7462	Intermediate Similarity	NPD7698	Approved
0.7462	Intermediate Similarity	NPD7696	Phase 3
0.7462	Intermediate Similarity	NPD7697	Approved
0.7462	Intermediate Similarity	NPD7435	Discontinued
0.7457	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7266	Discontinued
0.7442	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1607	Approved
0.7412	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7701	Phase 2
0.7396	Intermediate Similarity	NPD2935	Discontinued
0.7396	Intermediate Similarity	NPD1551	Phase 2
0.7386	Intermediate Similarity	NPD3226	Approved
0.7368	Intermediate Similarity	NPD6674	Discontinued
0.7365	Intermediate Similarity	NPD1933	Approved
0.7347	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7870	Phase 2
0.7337	Intermediate Similarity	NPD7871	Phase 2
0.7333	Intermediate Similarity	NPD3027	Phase 3
0.7326	Intermediate Similarity	NPD4628	Phase 3
0.7326	Intermediate Similarity	NPD3750	Approved
0.7326	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD6823	Phase 2
0.732	Intermediate Similarity	NPD6534	Approved
0.732	Intermediate Similarity	NPD6535	Approved
0.7305	Intermediate Similarity	NPD943	Approved
0.7296	Intermediate Similarity	NPD7700	Phase 2
0.7296	Intermediate Similarity	NPD7699	Phase 2
0.7291	Intermediate Similarity	NPD7801	Approved
0.7288	Intermediate Similarity	NPD7458	Discontinued
0.7286	Intermediate Similarity	NPD7680	Approved
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1243	Approved
0.7257	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8320	Phase 1
0.725	Intermediate Similarity	NPD8319	Approved
0.7245	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7874	Approved
0.7241	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5953	Discontinued
0.7231	Intermediate Similarity	NPD4360	Phase 2
0.7231	Intermediate Similarity	NPD4363	Phase 3
0.7228	Intermediate Similarity	NPD7585	Approved
0.7219	Intermediate Similarity	NPD6651	Approved
0.7212	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8150	Discontinued
0.7186	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7930	Approved
0.7178	Intermediate Similarity	NPD7583	Approved
0.716	Intermediate Similarity	NPD447	Suspended
0.716	Intermediate Similarity	NPD230	Phase 1
0.7159	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5710	Approved
0.7135	Intermediate Similarity	NPD2799	Discontinued
0.7135	Intermediate Similarity	NPD5711	Approved
0.7128	Intermediate Similarity	NPD7286	Phase 2
0.7102	Intermediate Similarity	NPD7390	Discontinued
0.7095	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6100	Approved
0.7093	Intermediate Similarity	NPD6099	Approved
0.7092	Intermediate Similarity	NPD6212	Phase 3
0.7092	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6213	Phase 3
0.7086	Intermediate Similarity	NPD6190	Approved
0.7081	Intermediate Similarity	NPD8127	Discontinued
0.7066	Intermediate Similarity	NPD4908	Phase 1
0.7059	Intermediate Similarity	NPD5124	Phase 1
0.7059	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2344	Approved
0.7052	Intermediate Similarity	NPD2346	Discontinued
0.7043	Intermediate Similarity	NPD7229	Phase 3
0.7035	Intermediate Similarity	NPD7033	Discontinued
0.7035	Intermediate Similarity	NPD3748	Approved
0.7029	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4361	Phase 2
0.702	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD9494	Approved
0.6995	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3268	Approved
0.6982	Remote Similarity	NPD2313	Discontinued
0.698	Remote Similarity	NPD5006	Approved
0.698	Remote Similarity	NPD5005	Approved
0.6973	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2403	Approved
0.6961	Remote Similarity	NPD7028	Phase 2
0.6954	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1091	Approved
0.6946	Remote Similarity	NPD2798	Approved
0.694	Remote Similarity	NPD5760	Phase 2
0.694	Remote Similarity	NPD5761	Phase 2
0.6936	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2424	Discontinued
0.6902	Remote Similarity	NPD5353	Approved
0.6901	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD2163	Approved
0.6893	Remote Similarity	NPD2309	Approved
0.6887	Remote Similarity	NPD4111	Phase 1
0.6887	Remote Similarity	NPD4665	Approved
0.6866	Remote Similarity	NPD4420	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data