NPASS Compound

Structure

CID92589 OpenBabel06191715432D 37 40 0 0 1 0 0 0 0 0999 V2000 0.9593 -2.2796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9593 -1.2796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4742 -3.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4530 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5870 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4530 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5870 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4087 -3.0385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7177 -2.0874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7614 -2.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4305 -3.2464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 -1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0485 -1.3443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1215 -4.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3576 -0.3932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7906 -4.9406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -2.6456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1433 -4.4053 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 29 1 0 0 0 0 2 29 1 0 0 0 0 3 35 1 0 0 0 0 4 36 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 17 28 1 0 0 0 0 18 19 2 0 0 0 0 19 30 1 0 0 0 0 20 24 1 0 0 0 0 20 31 2 0 0 0 0 21 24 1 0 0 0 0 21 32 1 0 0 0 0 22 25 2 0 0 0 0 22 35 1 0 0 0 0 23 18 1 1 0 0 0 23 25 1 0 0 0 0 23 27 1 0 0 0 0 24 26 2 0 0 0 0 25 26 1 0 0 0 0 26 37 1 0 0 0 0 27 29 1 6 0 0 0 27 37 1 0 0 0 0 28 33 2 0 0 0 0 28 36 1 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.19
Volume:	517.235
LogP:	5.088
LogD:	3.493
LogS:	-3.107
# Rotatable Bonds:	9
TPSA:	122.52
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.304
Synthetic Accessibility Score:	3.616
Fsp3:	0.31
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.938
MDCK Permeability:	2.9270471713971347e-05
Pgp-inhibitor:	0.915
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	99.55364227294922%
Volume Distribution (VD):	0.401
Pgp-substrate:	1.381725788116455%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.71
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.292
CYP2C9-inhibitor:	0.926
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.875
CYP2D6-substrate:	0.452
CYP3A4-inhibitor:	0.777
CYP3A4-substrate:	0.548

ADMET: Excretion

Clearance (CL):	8.738
Half-life (T1/2):	0.267

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.393
Maximum Recommended Daily Dose:	0.495
Skin Sensitization:	0.137
Carcinogencity:	0.072
Eye Corrosion:	0.003
Eye Irritation:	0.121
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC92589

Natural Product ID:	NPC92589
*Common Name:**	Piperaduncin B
IUPAC Name:	methyl 4-hydroxy-3-[(2S,3S)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate
Synonyms:	Piperaduncin B
Standard InCHIKey:	KGNWKZGVYSTAOX-HOFKKMOUSA-N
Standard InCHI:	InChI=1S/C29H30O8/c1-29(2,34)27-23(18-14-17(28(33)36-4)11-13-19(18)30)25-22(35-3)15-21(32)24(26(25)37-27)20(31)12-10-16-8-6-5-7-9-16/h5-9,11,13-15,23,27,30,32,34H,10,12H2,1-4H3/t23-,27-/m0/s1
SMILES:	CC(C)([C@@H]1[C@@H](c2cc(ccc2O)C(=O)OC)c2c(cc(c(C(=O)CCc3ccccc3)c2O1)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486612
PubChem CID:	442455
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO8059	Piper aduncum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158163]
NPO8059	Piper aduncum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8059	Piper aduncum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8059	Piper aduncum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8059	Piper aduncum	Species	Piperaceae	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
ED50	1
MIC	3

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.7	ug ml-1	PMID[462901]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.2	ug	PMID[462901]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	0.4	ug	PMID[462901]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	5.0	ug	PMID[462901]

☑ 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 NPC92589 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	360
0.1-0.2	1364
0.2-0.3	3050
0.3-0.4	7221
0.4-0.5	10779
0.5-0.6	4555
0.6-0.7	4658
0.7-0.8	5766
0.8-0.85	3131
0.85-0.9	1652
0.9-0.95	160
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC474609
0.9481	High Similarity	NPC475797
0.9481	High Similarity	NPC129053
0.9481	High Similarity	NPC78554
0.9481	High Similarity	NPC469936
0.9481	High Similarity	NPC109967
0.9481	High Similarity	NPC321372
0.9481	High Similarity	NPC474738
0.9416	High Similarity	NPC108937
0.9416	High Similarity	NPC279218
0.9412	High Similarity	NPC476238
0.9412	High Similarity	NPC473996
0.9412	High Similarity	NPC327269
0.9412	High Similarity	NPC31627
0.9408	High Similarity	NPC472421
0.9363	High Similarity	NPC97812
0.9355	High Similarity	NPC471787
0.9346	High Similarity	NPC471675
0.9346	High Similarity	NPC472580
0.9346	High Similarity	NPC472636
0.9346	High Similarity	NPC474744
0.9346	High Similarity	NPC474772
0.9346	High Similarity	NPC472423
0.929	High Similarity	NPC469934
0.9286	High Similarity	NPC285623
0.9286	High Similarity	NPC477957
0.9245	High Similarity	NPC91288
0.9221	High Similarity	NPC290671
0.9221	High Similarity	NPC316960
0.9221	High Similarity	NPC148945
0.9221	High Similarity	NPC204561
0.9221	High Similarity	NPC472420
0.9221	High Similarity	NPC309512
0.9221	High Similarity	NPC317715
0.9221	High Similarity	NPC78835
0.9221	High Similarity	NPC472422
0.9221	High Similarity	NPC471676
0.9221	High Similarity	NPC263384
0.9221	High Similarity	NPC244577
0.9211	High Similarity	NPC14875
0.9198	High Similarity	NPC120220
0.9167	High Similarity	NPC470681
0.9161	High Similarity	NPC256141
0.9156	High Similarity	NPC327059
0.9156	High Similarity	NPC476509
0.9156	High Similarity	NPC321387
0.9156	High Similarity	NPC180351
0.915	High Similarity	NPC168085
0.9145	High Similarity	NPC25844
0.9141	High Similarity	NPC472584
0.9125	High Similarity	NPC471286
0.9108	High Similarity	NPC215917
0.9108	High Similarity	NPC10754
0.9108	High Similarity	NPC20530
0.9108	High Similarity	NPC78492
0.9108	High Similarity	NPC208152
0.9103	High Similarity	NPC223701
0.9103	High Similarity	NPC7989
0.9103	High Similarity	NPC472583
0.9097	High Similarity	NPC471677
0.9091	High Similarity	NPC89442
0.9091	High Similarity	NPC317492
0.9074	High Similarity	NPC476459
0.9068	High Similarity	NPC204088
0.9068	High Similarity	NPC329215
0.9068	High Similarity	NPC259007
0.9062	High Similarity	NPC93215
0.9057	High Similarity	NPC306978
0.9057	High Similarity	NPC328102
0.9057	High Similarity	NPC470810
0.9045	High Similarity	NPC477958
0.9038	High Similarity	NPC56232
0.9038	High Similarity	NPC150123
0.9038	High Similarity	NPC171651
0.9038	High Similarity	NPC216035
0.9038	High Similarity	NPC35567
0.9038	High Similarity	NPC217149
0.9038	High Similarity	NPC243171
0.9038	High Similarity	NPC475790
0.9038	High Similarity	NPC244583
0.9038	High Similarity	NPC161881
0.9038	High Similarity	NPC210597
0.9038	High Similarity	NPC10807
0.9032	High Similarity	NPC321896
0.9032	High Similarity	NPC476185
0.9032	High Similarity	NPC474735
0.9032	High Similarity	NPC470908
0.9026	High Similarity	NPC39195
0.9024	High Similarity	NPC477529
0.902	High Similarity	NPC316769
0.902	High Similarity	NPC477955
0.9012	High Similarity	NPC323137
0.9006	High Similarity	NPC473009
0.9006	High Similarity	NPC472581
0.9	High Similarity	NPC30655
0.9	High Similarity	NPC301256
0.9	High Similarity	NPC74854
0.9	High Similarity	NPC45124
0.9	High Similarity	NPC312273
0.8994	High Similarity	NPC40583
0.8987	High Similarity	NPC470625
0.8981	High Similarity	NPC213608
0.8981	High Similarity	NPC1477
0.8981	High Similarity	NPC244250
0.8981	High Similarity	NPC469405
0.8981	High Similarity	NPC293286
0.8981	High Similarity	NPC100134
0.8981	High Similarity	NPC209760
0.8981	High Similarity	NPC20907
0.8976	High Similarity	NPC324220
0.8976	High Similarity	NPC312630
0.8974	High Similarity	NPC474023
0.8974	High Similarity	NPC278476
0.8974	High Similarity	NPC178484
0.8974	High Similarity	NPC295650
0.8974	High Similarity	NPC262039
0.8974	High Similarity	NPC312549
0.8974	High Similarity	NPC209142
0.8974	High Similarity	NPC328740
0.8974	High Similarity	NPC254412
0.8974	High Similarity	NPC209846
0.8974	High Similarity	NPC471229
0.8974	High Similarity	NPC477897
0.8974	High Similarity	NPC289774
0.8974	High Similarity	NPC262038
0.8974	High Similarity	NPC319910
0.8974	High Similarity	NPC474021
0.8968	High Similarity	NPC164299
0.8968	High Similarity	NPC472628
0.8968	High Similarity	NPC307052
0.8968	High Similarity	NPC139966
0.8968	High Similarity	NPC164205
0.8968	High Similarity	NPC473016
0.8968	High Similarity	NPC104236
0.8963	High Similarity	NPC102277
0.8963	High Similarity	NPC180768
0.8963	High Similarity	NPC287884
0.8963	High Similarity	NPC279209
0.8963	High Similarity	NPC8704
0.8963	High Similarity	NPC76047
0.8961	High Similarity	NPC472627
0.8961	High Similarity	NPC308200
0.8961	High Similarity	NPC222298
0.8961	High Similarity	NPC202494
0.8961	High Similarity	NPC47388
0.8961	High Similarity	NPC473133
0.8961	High Similarity	NPC51070
0.8961	High Similarity	NPC470670
0.8957	High Similarity	NPC292233
0.8954	High Similarity	NPC473015
0.8954	High Similarity	NPC209040
0.8954	High Similarity	NPC271288
0.8954	High Similarity	NPC469953
0.8954	High Similarity	NPC131579
0.8954	High Similarity	NPC131568
0.8954	High Similarity	NPC473013
0.8951	High Similarity	NPC473010
0.8951	High Similarity	NPC471788
0.8947	High Similarity	NPC130206
0.8944	High Similarity	NPC473012
0.8944	High Similarity	NPC219861
0.8944	High Similarity	NPC472635
0.8944	High Similarity	NPC310603
0.8938	High Similarity	NPC115432
0.8938	High Similarity	NPC260296
0.8938	High Similarity	NPC74749
0.8938	High Similarity	NPC472624
0.8938	High Similarity	NPC472055
0.8938	High Similarity	NPC220582
0.8938	High Similarity	NPC304839
0.8938	High Similarity	NPC114147
0.8938	High Similarity	NPC19554
0.8938	High Similarity	NPC43971
0.8931	High Similarity	NPC322459
0.8931	High Similarity	NPC35598
0.8931	High Similarity	NPC323627
0.8931	High Similarity	NPC475184
0.8931	High Similarity	NPC65504
0.8931	High Similarity	NPC318527
0.8931	High Similarity	NPC23817
0.8931	High Similarity	NPC324358
0.8931	High Similarity	NPC43638
0.8931	High Similarity	NPC161650
0.8931	High Similarity	NPC222689
0.8924	High Similarity	NPC471116
0.8924	High Similarity	NPC476169
0.8924	High Similarity	NPC304745
0.8924	High Similarity	NPC207809
0.8924	High Similarity	NPC48579
0.8924	High Similarity	NPC111341
0.8924	High Similarity	NPC304207
0.8924	High Similarity	NPC259710
0.8924	High Similarity	NPC217706
0.8917	High Similarity	NPC5871
0.8917	High Similarity	NPC138288
0.891	High Similarity	NPC124478
0.891	High Similarity	NPC471115
0.891	High Similarity	NPC61258
0.891	High Similarity	NPC267117
0.891	High Similarity	NPC105136

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 NPC92589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	858
0.2-0.3	1625
0.3-0.4	2474
0.4-0.5	2027
0.5-0.6	1143
0.6-0.7	471
0.7-0.8	171
0.8-0.85	42
0.85-0.9	28
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9172	High Similarity	NPD7075	Discontinued
0.8981	High Similarity	NPD7096	Clinical (unspecified phase)
0.8974	High Similarity	NPD7411	Suspended
0.8924	High Similarity	NPD8443	Clinical (unspecified phase)
0.8917	High Similarity	NPD6801	Discontinued
0.891	High Similarity	NPD4380	Phase 2
0.8831	High Similarity	NPD7410	Clinical (unspecified phase)
0.8742	High Similarity	NPD2393	Clinical (unspecified phase)
0.8742	High Similarity	NPD7819	Suspended
0.872	High Similarity	NPD7852	Clinical (unspecified phase)
0.871	High Similarity	NPD4378	Clinical (unspecified phase)
0.8696	High Similarity	NPD4381	Clinical (unspecified phase)
0.8645	High Similarity	NPD6799	Approved
0.8634	High Similarity	NPD7768	Phase 2
0.8634	High Similarity	NPD4868	Clinical (unspecified phase)
0.8631	High Similarity	NPD6559	Discontinued
0.858	High Similarity	NPD3749	Approved
0.8562	High Similarity	NPD1549	Phase 2
0.8562	High Similarity	NPD1934	Approved
0.8554	High Similarity	NPD7473	Discontinued
0.8553	High Similarity	NPD6599	Discontinued
0.8506	High Similarity	NPD7421	Clinical (unspecified phase)
0.8503	High Similarity	NPD3818	Discontinued
0.8497	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6166	Phase 2
0.8494	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD6232	Discontinued
0.8476	Intermediate Similarity	NPD5494	Approved
0.8457	Intermediate Similarity	NPD3817	Phase 2
0.8452	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD2796	Approved
0.8424	Intermediate Similarity	NPD6959	Discontinued
0.8405	Intermediate Similarity	NPD3882	Suspended
0.8366	Intermediate Similarity	NPD1510	Phase 2
0.8365	Intermediate Similarity	NPD5403	Approved
0.8343	Intermediate Similarity	NPD5844	Phase 1
0.8282	Intermediate Similarity	NPD2801	Approved
0.825	Intermediate Similarity	NPD920	Approved
0.8239	Intermediate Similarity	NPD2532	Approved
0.8239	Intermediate Similarity	NPD2533	Approved
0.8239	Intermediate Similarity	NPD2534	Approved
0.8239	Intermediate Similarity	NPD5401	Approved
0.8232	Intermediate Similarity	NPD5402	Approved
0.8224	Intermediate Similarity	NPD1240	Approved
0.8217	Intermediate Similarity	NPD3750	Approved
0.8217	Intermediate Similarity	NPD4628	Phase 3
0.8187	Intermediate Similarity	NPD7074	Phase 3
0.8176	Intermediate Similarity	NPD1511	Approved
0.8153	Intermediate Similarity	NPD1243	Approved
0.8153	Intermediate Similarity	NPD2800	Approved
0.814	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2799	Discontinued
0.8129	Intermediate Similarity	NPD7054	Approved
0.8125	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD1607	Approved
0.8113	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7472	Approved
0.8077	Intermediate Similarity	NPD2935	Discontinued
0.8077	Intermediate Similarity	NPD1551	Phase 2
0.8075	Intermediate Similarity	NPD1512	Approved
0.8046	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD3226	Approved
0.8035	Intermediate Similarity	NPD5953	Discontinued
0.8035	Intermediate Similarity	NPD6797	Phase 2
0.8025	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8313	Approved
0.8	Intermediate Similarity	NPD8312	Approved
0.7989	Intermediate Similarity	NPD7251	Discontinued
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7199	Phase 2
0.7976	Intermediate Similarity	NPD919	Approved
0.7974	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD8434	Phase 2
0.7943	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7808	Phase 3
0.7919	Intermediate Similarity	NPD7286	Phase 2
0.7911	Intermediate Similarity	NPD2344	Approved
0.7898	Intermediate Similarity	NPD3748	Approved
0.7895	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6234	Discontinued
0.7857	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2313	Discontinued
0.7844	Intermediate Similarity	NPD1465	Phase 2
0.7836	Intermediate Similarity	NPD7229	Phase 3
0.7818	Intermediate Similarity	NPD7458	Discontinued
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7785	Intermediate Similarity	NPD7033	Discontinued
0.7784	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6651	Approved
0.7764	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD4967	Phase 2
0.7751	Intermediate Similarity	NPD4966	Approved
0.7751	Intermediate Similarity	NPD4965	Approved
0.7742	Intermediate Similarity	NPD6798	Discontinued
0.7742	Intermediate Similarity	NPD3764	Approved
0.7738	Intermediate Similarity	NPD8455	Phase 2
0.7727	Intermediate Similarity	NPD4908	Phase 1
0.7727	Intermediate Similarity	NPD6832	Phase 2
0.7716	Intermediate Similarity	NPD2309	Approved
0.7711	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6355	Discontinued
0.7688	Intermediate Similarity	NPD2346	Discontinued
0.7674	Intermediate Similarity	NPD1247	Approved
0.7667	Intermediate Similarity	NPD8150	Discontinued
0.7647	Intermediate Similarity	NPD1203	Approved
0.763	Intermediate Similarity	NPD5710	Approved
0.763	Intermediate Similarity	NPD5711	Approved
0.7628	Intermediate Similarity	NPD3268	Approved
0.7622	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7390	Discontinued
0.7619	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5124	Phase 1
0.7582	Intermediate Similarity	NPD4287	Approved
0.758	Intermediate Similarity	NPD6233	Phase 2
0.7566	Intermediate Similarity	NPD7435	Discontinued
0.7562	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7228	Approved
0.7557	Intermediate Similarity	NPD3751	Discontinued
0.7557	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7546	Intermediate Similarity	NPD7003	Approved
0.7539	Intermediate Similarity	NPD7584	Approved
0.7532	Intermediate Similarity	NPD2797	Approved
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.7484	Intermediate Similarity	NPD230	Phase 1
0.7484	Intermediate Similarity	NPD2798	Approved
0.7474	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7783	Phase 2
0.7473	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4361	Phase 2
0.7469	Intermediate Similarity	NPD6002	Phase 3
0.7469	Intermediate Similarity	NPD6005	Phase 3
0.7469	Intermediate Similarity	NPD6004	Phase 3
0.7469	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4308	Phase 3
0.7451	Intermediate Similarity	NPD9717	Approved
0.7429	Intermediate Similarity	NPD3787	Discontinued
0.7427	Intermediate Similarity	NPD5761	Phase 2
0.7427	Intermediate Similarity	NPD5760	Phase 2
0.7425	Intermediate Similarity	NPD6273	Approved
0.7421	Intermediate Similarity	NPD4060	Phase 1
0.7421	Intermediate Similarity	NPD943	Approved
0.7407	Intermediate Similarity	NPD5405	Approved
0.7407	Intermediate Similarity	NPD5408	Approved
0.7407	Intermediate Similarity	NPD5404	Approved
0.7407	Intermediate Similarity	NPD5406	Approved
0.7389	Intermediate Similarity	NPD7685	Pre-registration
0.7386	Intermediate Similarity	NPD1610	Phase 2
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1933	Approved
0.7375	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD447	Suspended
0.7345	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD2403	Approved
0.7344	Intermediate Similarity	NPD7870	Phase 2
0.7344	Intermediate Similarity	NPD7871	Phase 2
0.7338	Intermediate Similarity	NPD1608	Approved
0.7333	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7874	Approved
0.733	Intermediate Similarity	NPD6808	Phase 2
0.7321	Intermediate Similarity	NPD5049	Phase 3
0.732	Intermediate Similarity	NPD7585	Approved
0.7317	Intermediate Similarity	NPD2424	Discontinued
0.7316	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1613	Approved
0.7312	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3266	Approved
0.7308	Intermediate Similarity	NPD3267	Approved
0.7292	Intermediate Similarity	NPD7696	Phase 3
0.7292	Intermediate Similarity	NPD7698	Approved
0.7292	Intermediate Similarity	NPD7697	Approved
0.7289	Intermediate Similarity	NPD3887	Approved
0.7289	Intermediate Similarity	NPD2354	Approved
0.7284	Intermediate Similarity	NPD7097	Phase 1
0.7283	Intermediate Similarity	NPD4288	Approved
0.7278	Intermediate Similarity	NPD1729	Discontinued
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7273	Intermediate Similarity	NPD8127	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