NPASS Compound

Structure

NPC282957 OpenBabel07101719252D 43 46 0 0 0 0 0 0 0 0999 V2000 -1.6952 1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7808 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6284 -2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 4.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9332 -2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6284 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4760 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 4.8936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7808 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4760 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 4.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3236 -0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 4.8936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9332 -0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 1.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 0.9787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -1.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 0.9787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -2.4468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 42 1 0 0 0 0 2 43 1 0 0 0 0 3 9 1 0 0 0 0 3 18 2 0 0 0 0 4 10 2 0 0 0 0 4 18 1 0 0 0 0 5 11 1 0 0 0 0 5 19 2 0 0 0 0 6 12 2 0 0 0 0 6 19 1 0 0 0 0 7 13 1 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 19 1 0 0 0 0 9 20 2 0 0 0 0 10 20 1 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 26 2 0 0 0 0 16 28 1 0 0 0 0 17 27 2 0 0 0 0 17 29 1 0 0 0 0 20 34 1 0 0 0 0 21 35 1 0 0 0 0 22 28 2 0 0 0 0 22 32 1 0 0 0 0 23 29 2 0 0 0 0 23 33 1 0 0 0 0 24 30 1 0 0 0 0 24 36 2 0 0 0 0 25 31 1 0 0 0 0 25 37 2 0 0 0 0 26 30 1 0 0 0 0 26 38 1 0 0 0 0 27 31 1 0 0 0 0 27 39 1 0 0 0 0 28 42 1 0 0 0 0 29 43 1 0 0 0 0 30 32 2 0 0 0 0 31 33 2 0 0 0 0 32 40 1 0 0 0 0 33 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	588.2
Volume:	596.09
LogP:	5.981
LogD:	3.442
LogS:	-3.152
# Rotatable Bonds:	12
TPSA:	173.98
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.121
Synthetic Accessibility Score:	2.94
Fsp3:	0.212
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:	-5.932
MDCK Permeability:	9.257334568246733e-06
Pgp-inhibitor:	0.171
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.961
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	98.67965698242188%
Volume Distribution (VD):	0.261
Pgp-substrate:	1.6380631923675537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.479
CYP1A2-substrate:	0.874
CYP2C19-inhibitor:	0.913
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.481
CYP2D6-substrate:	0.843
CYP3A4-inhibitor:	0.458
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	10.395
Half-life (T1/2):	0.794

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.552
Rat Oral Acute Toxicity:	0.141
Maximum Recommended Daily Dose:	0.107
Skin Sensitization:	0.949
Carcinogencity:	0.087
Eye Corrosion:	0.003
Eye Irritation:	0.86
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC282957

Natural Product ID:	NPC282957
*Common Name:**	Pierotin A
IUPAC Name:	1-[3-[[2,4-dihydroxy-3-[3-(4-hydroxyphenyl)propanoyl]-6-methoxyphenyl]methyl]-2,6-dihydroxy-4-methoxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	FLBZSYKHHHOVLP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C33H32O10/c1-42-28-16-26(38)30(24(36)13-7-18-3-9-20(34)10-4-18)32(40)22(28)15-23-29(43-2)17-27(39)31(33(23)41)25(37)14-8-19-5-11-21(35)12-6-19/h3-6,9-12,16-17,34-35,38-41H,7-8,13-15H2,1-2H3
SMILES:	COc1cc(O)c(c(c1Cc1c(OC)cc(c(c1O)C(=O)CCc1ccc(cc1)O)O)O)C(=O)CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451422
PubChem CID:	11192582
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787442]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15787442]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31809052]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13961	Pieris japonica	Species	Ericaceae	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	6

Activity Type	# Activity
NON-MOLECULAR	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	36.5	10'-3cpm	PMID[493519]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	32.7	10'-3cpm	PMID[493519]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	38.12	10'-3cpm	PMID[493519]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	22.62	10'-3cpm	PMID[493519]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	74.98	10'-3cpm	PMID[493519]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	75.44	10'-3cpm	PMID[493519]

☑ 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 NPC282957 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	380
0.1-0.2	1614
0.2-0.3	3986
0.3-0.4	11265
0.4-0.5	7116
0.5-0.6	4012
0.6-0.7	5984
0.7-0.8	5541
0.8-0.85	1659
0.85-0.9	782
0.9-0.95	348
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC194949
0.9783	High Similarity	NPC26238
0.9716	High Similarity	NPC261271
0.9716	High Similarity	NPC475348
0.9648	High Similarity	NPC152233
0.9565	High Similarity	NPC243528
0.9565	High Similarity	NPC251681
0.9517	High Similarity	NPC43345
0.9452	High Similarity	NPC324447
0.9448	High Similarity	NPC476552
0.9448	High Similarity	NPC476553
0.9448	High Similarity	NPC476551
0.9437	High Similarity	NPC471524
0.9437	High Similarity	NPC471473
0.9437	High Similarity	NPC471523
0.9388	High Similarity	NPC37253
0.9388	High Similarity	NPC79375
0.9384	High Similarity	NPC78324
0.9384	High Similarity	NPC208011
0.9384	High Similarity	NPC39154
0.9384	High Similarity	NPC115601
0.9348	High Similarity	NPC13575
0.931	High Similarity	NPC3642
0.9281	High Similarity	NPC12165
0.9281	High Similarity	NPC98115
0.9281	High Similarity	NPC249606
0.9281	High Similarity	NPC41461
0.9281	High Similarity	NPC25287
0.9281	High Similarity	NPC477242
0.9281	High Similarity	NPC150399
0.9281	High Similarity	NPC1486
0.9281	High Similarity	NPC477244
0.9281	High Similarity	NPC274109
0.9281	High Similarity	NPC168105
0.9281	High Similarity	NPC66349
0.9281	High Similarity	NPC477243
0.9281	High Similarity	NPC186838
0.9275	High Similarity	NPC103842
0.9262	High Similarity	NPC208258
0.9262	High Similarity	NPC257166
0.9262	High Similarity	NPC1796
0.9257	High Similarity	NPC265624
0.9257	High Similarity	NPC121649
0.9257	High Similarity	NPC215203
0.9257	High Similarity	NPC205026
0.9257	High Similarity	NPC150908
0.9257	High Similarity	NPC186227
0.9257	High Similarity	NPC248739
0.9257	High Similarity	NPC14606
0.9257	High Similarity	NPC158027
0.9257	High Similarity	NPC52611
0.9257	High Similarity	NPC100049
0.9257	High Similarity	NPC159707
0.9241	High Similarity	NPC122894
0.9236	High Similarity	NPC470134
0.9236	High Similarity	NPC109183
0.9236	High Similarity	NPC470133
0.9236	High Similarity	NPC473078
0.9236	High Similarity	NPC470131
0.9236	High Similarity	NPC470132
0.9236	High Similarity	NPC228779
0.9225	High Similarity	NPC14871
0.9214	High Similarity	NPC317119
0.9214	High Similarity	NPC153979
0.9214	High Similarity	NPC472419
0.9209	High Similarity	NPC131039
0.9209	High Similarity	NPC156092
0.9203	High Similarity	NPC204960
0.9203	High Similarity	NPC16197
0.9203	High Similarity	NPC20560
0.9203	High Similarity	NPC144051
0.9203	High Similarity	NPC82225
0.9203	High Similarity	NPC28753
0.9203	High Similarity	NPC18877
0.9203	High Similarity	NPC294593
0.9203	High Similarity	NPC159623
0.92	High Similarity	NPC51247
0.92	High Similarity	NPC15815
0.92	High Similarity	NPC90497
0.9195	High Similarity	NPC54830
0.9195	High Similarity	NPC56049
0.9189	High Similarity	NPC121568
0.9189	High Similarity	NPC303485
0.9189	High Similarity	NPC71061
0.9189	High Similarity	NPC72425
0.9189	High Similarity	NPC290830
0.9189	High Similarity	NPC194593
0.9184	High Similarity	NPC178484
0.9178	High Similarity	NPC291746
0.9178	High Similarity	NPC288840
0.9178	High Similarity	NPC132345
0.9167	High Similarity	NPC257236
0.9167	High Similarity	NPC470136
0.9167	High Similarity	NPC470135
0.9167	High Similarity	NPC278175
0.9167	High Similarity	NPC39045
0.9161	High Similarity	NPC297600
0.9155	High Similarity	NPC326109
0.9155	High Similarity	NPC219917
0.9155	High Similarity	NPC213659
0.9155	High Similarity	NPC241100
0.9155	High Similarity	NPC259166
0.9155	High Similarity	NPC159275
0.9155	High Similarity	NPC204985
0.9155	High Similarity	NPC172250
0.9155	High Similarity	NPC215311
0.9155	High Similarity	NPC48624
0.9155	High Similarity	NPC144118
0.9155	High Similarity	NPC80962
0.9149	High Similarity	NPC21350
0.9139	High Similarity	NPC42965
0.9139	High Similarity	NPC226462
0.9139	High Similarity	NPC195136
0.9139	High Similarity	NPC121647
0.9139	High Similarity	NPC98023
0.9137	High Similarity	NPC286336
0.913	High Similarity	NPC215875
0.913	High Similarity	NPC15834
0.9122	High Similarity	NPC174086
0.9103	High Similarity	NPC25844
0.9097	High Similarity	NPC185276
0.9091	High Similarity	NPC268204
0.9091	High Similarity	NPC469404
0.9091	High Similarity	NPC55832
0.9091	High Similarity	NPC110969
0.9091	High Similarity	NPC282300
0.9091	High Similarity	NPC52789
0.9091	High Similarity	NPC26051
0.9085	High Similarity	NPC53181
0.9085	High Similarity	NPC470211
0.9085	High Similarity	NPC96565
0.9085	High Similarity	NPC217186
0.9085	High Similarity	NPC220062
0.9085	High Similarity	NPC55018
0.9085	High Similarity	NPC216978
0.9085	High Similarity	NPC283429
0.9085	High Similarity	NPC78913
0.9085	High Similarity	NPC472366
0.9085	High Similarity	NPC295384
0.9085	High Similarity	NPC301217
0.9085	High Similarity	NPC303633
0.9085	High Similarity	NPC477956
0.9085	High Similarity	NPC18260
0.9078	High Similarity	NPC322301
0.9078	High Similarity	NPC255801
0.9073	High Similarity	NPC18699
0.9073	High Similarity	NPC55443
0.9073	High Similarity	NPC105584
0.9065	High Similarity	NPC242294
0.9065	High Similarity	NPC192304
0.9065	High Similarity	NPC56031
0.9065	High Similarity	NPC337373
0.9065	High Similarity	NPC27643
0.9065	High Similarity	NPC263670
0.9065	High Similarity	NPC472365
0.9065	High Similarity	NPC188646
0.9065	High Similarity	NPC175098
0.9065	High Similarity	NPC312318
0.9065	High Similarity	NPC139813
0.9058	High Similarity	NPC475009
0.9058	High Similarity	NPC475008
0.9058	High Similarity	NPC186097
0.9054	High Similarity	NPC222713
0.9054	High Similarity	NPC138299
0.9054	High Similarity	NPC67322
0.9054	High Similarity	NPC111112
0.9041	High Similarity	NPC283234
0.9034	High Similarity	NPC328623
0.9034	High Similarity	NPC197252
0.9034	High Similarity	NPC236766
0.9034	High Similarity	NPC235217
0.9034	High Similarity	NPC319752
0.9034	High Similarity	NPC473014
0.9028	High Similarity	NPC324436
0.9028	High Similarity	NPC194432
0.9028	High Similarity	NPC223500
0.9028	High Similarity	NPC226636
0.9028	High Similarity	NPC32739
0.9028	High Similarity	NPC76372
0.9028	High Similarity	NPC66515
0.9028	High Similarity	NPC78803
0.9028	High Similarity	NPC182852
0.9028	High Similarity	NPC228504
0.9028	High Similarity	NPC62840
0.9028	High Similarity	NPC328164
0.9028	High Similarity	NPC306829
0.9028	High Similarity	NPC59739
0.9028	High Similarity	NPC214236
0.9028	High Similarity	NPC64915
0.9028	High Similarity	NPC40833
0.9028	High Similarity	NPC125855
0.9028	High Similarity	NPC166934
0.9028	High Similarity	NPC296917
0.9028	High Similarity	NPC324134
0.9028	High Similarity	NPC148757
0.9028	High Similarity	NPC161506
0.9028	High Similarity	NPC78
0.9028	High Similarity	NPC166482
0.9028	High Similarity	NPC293852
0.9028	High Similarity	NPC37496

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 NPC282957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	965
0.2-0.3	1420
0.3-0.4	2718
0.4-0.5	1940
0.5-0.6	1218
0.6-0.7	371
0.7-0.8	140
0.8-0.85	23
0.85-0.9	11
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD7410	Clinical (unspecified phase)
0.9128	High Similarity	NPD8443	Clinical (unspecified phase)
0.8926	High Similarity	NPD7411	Suspended
0.8921	High Similarity	NPD1240	Approved
0.8904	High Similarity	NPD4378	Clinical (unspecified phase)
0.8816	High Similarity	NPD7768	Phase 2
0.8803	High Similarity	NPD1510	Phase 2
0.8794	High Similarity	NPD1607	Approved
0.8782	High Similarity	NPD7852	Clinical (unspecified phase)
0.8733	High Similarity	NPD4380	Phase 2
0.8681	High Similarity	NPD1552	Clinical (unspecified phase)
0.8681	High Similarity	NPD1550	Clinical (unspecified phase)
0.8621	High Similarity	NPD1549	Phase 2
0.859	High Similarity	NPD6959	Discontinued
0.8562	High Similarity	NPD7819	Suspended
0.8531	High Similarity	NPD6651	Approved
0.8516	High Similarity	NPD7075	Discontinued
0.8442	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD7473	Discontinued
0.8356	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD7390	Discontinued
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD6232	Discontinued
0.8272	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6801	Discontinued
0.8199	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6166	Phase 2
0.8165	Intermediate Similarity	NPD3749	Approved
0.8165	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1934	Approved
0.8108	Intermediate Similarity	NPD2935	Discontinued
0.8092	Intermediate Similarity	NPD6799	Approved
0.8092	Intermediate Similarity	NPD1511	Approved
0.8089	Intermediate Similarity	NPD2801	Approved
0.8013	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1512	Approved
0.7947	Intermediate Similarity	NPD2800	Approved
0.7919	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6599	Discontinued
0.7892	Intermediate Similarity	NPD7074	Phase 3
0.7877	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3882	Suspended
0.7875	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7054	Approved
0.7821	Intermediate Similarity	NPD5403	Approved
0.7812	Intermediate Similarity	NPD3817	Phase 2
0.7806	Intermediate Similarity	NPD2533	Approved
0.7806	Intermediate Similarity	NPD2532	Approved
0.7806	Intermediate Similarity	NPD2534	Approved
0.7784	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.7748	Intermediate Similarity	NPD5404	Approved
0.7748	Intermediate Similarity	NPD1551	Phase 2
0.7748	Intermediate Similarity	NPD5408	Approved
0.7748	Intermediate Similarity	NPD5405	Approved
0.7748	Intermediate Similarity	NPD5406	Approved
0.774	Intermediate Similarity	NPD4908	Phase 1
0.7738	Intermediate Similarity	NPD5953	Discontinued
0.7738	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD5494	Approved
0.7727	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7286	Phase 2
0.7722	Intermediate Similarity	NPD7458	Discontinued
0.7712	Intermediate Similarity	NPD1243	Approved
0.7707	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2344	Approved
0.7692	Intermediate Similarity	NPD6559	Discontinued
0.7692	Intermediate Similarity	NPD5401	Approved
0.7692	Intermediate Similarity	NPD7251	Discontinued
0.7682	Intermediate Similarity	NPD3748	Approved
0.7682	Intermediate Similarity	NPD2799	Discontinued
0.7665	Intermediate Similarity	NPD3818	Discontinued
0.7662	Intermediate Similarity	NPD7003	Approved
0.7651	Intermediate Similarity	NPD943	Approved
0.7647	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6797	Phase 2
0.7619	Intermediate Similarity	NPD5844	Phase 1
0.7619	Intermediate Similarity	NPD6832	Phase 2
0.761	Intermediate Similarity	NPD3226	Approved
0.7603	Intermediate Similarity	NPD2798	Approved
0.76	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2654	Approved
0.7595	Intermediate Similarity	NPD920	Approved
0.7586	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1203	Approved
0.7517	Intermediate Similarity	NPD2313	Discontinued
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.7485	Intermediate Similarity	NPD5402	Approved
0.7468	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3972	Approved
0.7442	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD8455	Phase 2
0.74	Intermediate Similarity	NPD3268	Approved
0.7381	Intermediate Similarity	NPD3926	Phase 2
0.7379	Intermediate Similarity	NPD1201	Approved
0.7379	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1548	Phase 1
0.7338	Intermediate Similarity	NPD7033	Discontinued
0.7329	Intermediate Similarity	NPD9717	Approved
0.7325	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4628	Phase 3
0.7324	Intermediate Similarity	NPD9493	Approved
0.7318	Intermediate Similarity	NPD4360	Phase 2
0.7318	Intermediate Similarity	NPD4363	Phase 3
0.7301	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2797	Approved
0.7297	Intermediate Similarity	NPD1470	Approved
0.7296	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3764	Approved
0.7273	Intermediate Similarity	NPD8151	Discontinued
0.726	Intermediate Similarity	NPD1610	Phase 2
0.726	Intermediate Similarity	NPD422	Phase 1
0.7255	Intermediate Similarity	NPD5124	Phase 1
0.7255	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD919	Approved
0.7244	Intermediate Similarity	NPD2346	Discontinued
0.7243	Intermediate Similarity	NPD7870	Phase 2
0.7243	Intermediate Similarity	NPD7871	Phase 2
0.723	Intermediate Similarity	NPD3225	Approved
0.7222	Intermediate Similarity	NPD9545	Approved
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD5711	Approved
0.7219	Intermediate Similarity	NPD5710	Approved
0.7212	Intermediate Similarity	NPD1465	Phase 2
0.7191	Intermediate Similarity	NPD4287	Approved
0.7189	Intermediate Similarity	NPD7697	Approved
0.7189	Intermediate Similarity	NPD7698	Approved
0.7189	Intermediate Similarity	NPD7696	Phase 3
0.7182	Intermediate Similarity	NPD4361	Phase 2
0.7182	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1164	Approved
0.7178	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6798	Discontinued
0.7168	Intermediate Similarity	NPD1729	Discontinued
0.716	Intermediate Similarity	NPD1247	Approved
0.7151	Intermediate Similarity	NPD7177	Discontinued
0.7135	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6780	Approved
0.712	Intermediate Similarity	NPD6778	Approved
0.712	Intermediate Similarity	NPD6782	Approved
0.712	Intermediate Similarity	NPD6777	Approved
0.712	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6781	Approved
0.712	Intermediate Similarity	NPD6776	Approved
0.712	Intermediate Similarity	NPD6779	Approved
0.7115	Intermediate Similarity	NPD4308	Phase 3
0.7105	Intermediate Similarity	NPD4625	Phase 3
0.7097	Intermediate Similarity	NPD7435	Discontinued
0.7079	Intermediate Similarity	NPD8150	Discontinued
0.7074	Intermediate Similarity	NPD7584	Approved
0.7067	Intermediate Similarity	NPD3266	Approved
0.7067	Intermediate Similarity	NPD3267	Approved
0.7066	Intermediate Similarity	NPD4288	Approved
0.7059	Intermediate Similarity	NPD7199	Phase 2
0.7055	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD37	Approved
0.7048	Intermediate Similarity	NPD7577	Discontinued
0.7037	Intermediate Similarity	NPD7447	Phase 1
0.7037	Intermediate Similarity	NPD7701	Phase 2
0.7032	Intermediate Similarity	NPD230	Phase 1
0.7032	Intermediate Similarity	NPD1933	Approved
0.7022	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1876	Approved
0.6993	Remote Similarity	NPD3027	Phase 3
0.6989	Remote Similarity	NPD6104	Discontinued
0.6988	Remote Similarity	NPD5890	Approved
0.6988	Remote Similarity	NPD5889	Approved
0.698	Remote Similarity	NPD1608	Approved
0.6977	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7212	Phase 2
0.6975	Remote Similarity	NPD7213	Phase 3
0.6964	Remote Similarity	NPD2296	Approved
0.6963	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7874	Approved
0.6952	Remote Similarity	NPD6823	Phase 2
0.6948	Remote Similarity	NPD1296	Phase 2
0.6941	Remote Similarity	NPD6234	Discontinued
0.6939	Remote Similarity	NPD1651	Approved
0.6928	Remote Similarity	NPD6585	Discontinued
0.6928	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7801	Approved
0.6927	Remote Similarity	NPD7783	Phase 2
0.6923	Remote Similarity	NPD4966	Approved
0.6923	Remote Similarity	NPD4965	Approved
0.6923	Remote Similarity	NPD1899	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