NPASS Compound

Structure

NPC63438 OpenBabel07101718222D 41 46 0 0 1 0 0 0 0 0999 V2000 4.2380 0.4894 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 -1.6952 -0.9787 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 5.0856 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9332 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -3.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 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 5.9332 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 0.8476 -4.4043 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 2.5428 0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 1.9574 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 0.8476 -2.4468 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 0.8476 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -0.9787 0.0000 C 0 0 1 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 -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 1 0 0 0 0 0 0 0 0 0 2.5428 -1.4681 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8476 0.4894 0.0000 C 0 0 2 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 6.7808 0.9787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -5.3830 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 3.3904 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 2.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9362 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 2.5428 -2.4468 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 5 1 0 0 0 0 1 12 2 0 0 0 0 2 6 2 0 0 0 0 2 12 1 0 0 0 0 3 7 1 0 0 0 0 3 13 2 0 0 0 0 4 8 2 0 0 0 0 4 13 1 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 10 20 2 0 0 0 0 11 18 2 0 0 0 0 11 19 1 0 0 0 0 14 31 1 0 0 0 0 15 32 1 0 0 0 0 16 33 1 0 0 0 0 17 21 2 0 0 0 0 17 34 1 0 0 0 0 18 22 1 0 0 0 0 18 35 1 0 0 0 0 19 23 2 0 0 0 0 19 36 1 0 0 0 0 20 21 1 0 0 0 0 20 40 1 0 0 0 0 21 25 1 0 0 0 0 22 30 2 0 0 0 0 23 26 1 0 0 0 0 23 30 1 0 0 0 0 24 22 1 6 0 0 0 24 25 1 0 0 0 0 24 28 1 0 0 0 0 25 37 2 0 0 0 0 26 27 1 0 0 0 0 26 38 2 0 0 0 0 27 29 1 0 0 0 0 27 39 1 1 0 0 0 28 12 1 1 0 0 0 28 40 1 0 0 0 0 29 13 1 6 0 0 0 29 41 1 0 0 0 0 30 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.12
Volume:	535.879
LogP:	3.614
LogD:	2.27
LogS:	-5.223
# Rotatable Bonds:	3
TPSA:	201.28
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.16
Synthetic Accessibility Score:	4.102
Fsp3:	0.1
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:	-6.254
MDCK Permeability:	5.350448645913275e-06
Pgp-inhibitor:	0.015
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.564
20% Bioavailability (F20%):	0.832
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	96.61375427246094%
Volume Distribution (VD):	0.471
Pgp-substrate:	3.526719331741333%

ADMET: Metabolism

CYP1A2-inhibitor:	0.318
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.679
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.146
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.193
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	4.501
Half-life (T1/2):	0.627

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.729
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.211
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.743
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC63438

Natural Product ID:	NPC63438
*Common Name:**	(2S,2'r,3R,3'r)-3',5,5',7,7'-Pentahydroxy-2,2'-Bis(4-Hydroxyphenyl)-3,8'-Bichroman-4,4'-Dione
IUPAC Name:	(2R,3R)-8-[(2S,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	AFDANKUHSLVEBJ-BENTYHEHSA-N
Standard InCHI:	InChI=1S/C30H22O11/c31-14-5-1-12(2-6-14)28-24(25(37)21-17(34)9-16(33)10-20(21)40-28)22-18(35)11-19(36)23-26(38)27(39)29(41-30(22)23)13-3-7-15(32)8-4-13/h1-11,24,27-29,31-36,39H/t24-,27-,28+,29+/m0/s1
SMILES:	c1cc(ccc1[C@@H]1[C@@H](c2c(cc(c3C(=O)[C@@H]([C@@H](c4ccc(cc4)O)Oc23)O)O)O)C(=O)c2c(cc(cc2O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504319
PubChem CID:	161087
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO32446	calophyllum panciflorum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654415]
NPO19087	Garcinia kola	Species	Clusiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[32644811]
NPO19087	Garcinia kola	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19087	Garcinia kola	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19087	Garcinia kola	Species	Clusiaceae	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
MIC	2
Others	10

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	4
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[545740]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[545740]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	25.3	%	PMID[545740]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	61.0	%	PMID[545740]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	88.2	%	PMID[545740]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	95.7	%	PMID[545740]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	>	1000000.0	nM	PMID[545741]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MBC	>	1000.0	uM	PMID[545741]
NPT1483	Organism	Streptococcus sobrinus	Streptococcus sobrinus	MIC	=	250000.0	nM	PMID[545741]
NPT1483	Organism	Streptococcus sobrinus	Streptococcus sobrinus	MBC	=	1000.0	uM	PMID[545741]

☑ 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 NPC63438 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	442
0.1-0.2	1655
0.2-0.3	3756
0.3-0.4	9381
0.4-0.5	9129
0.5-0.6	3875
0.6-0.7	5573
0.7-0.8	4934
0.8-0.85	2856
0.85-0.9	921
0.9-0.95	165
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC123544
0.9625	High Similarity	NPC186847
0.9625	High Similarity	NPC257667
0.9625	High Similarity	NPC472454
0.9613	High Similarity	NPC295090
0.961	High Similarity	NPC69531
0.9548	High Similarity	NPC475184
0.9484	High Similarity	NPC32867
0.9481	High Similarity	NPC20907
0.9481	High Similarity	NPC244250
0.9441	High Similarity	NPC287884
0.9441	High Similarity	NPC8704
0.9419	High Similarity	NPC201227
0.9419	High Similarity	NPC258474
0.9419	High Similarity	NPC134171
0.9419	High Similarity	NPC300668
0.9379	High Similarity	NPC107627
0.9375	High Similarity	NPC224851
0.9375	High Similarity	NPC82330
0.9363	High Similarity	NPC51247
0.9359	High Similarity	NPC61112
0.9359	High Similarity	NPC198489
0.9359	High Similarity	NPC309648
0.9355	High Similarity	NPC109594
0.9355	High Similarity	NPC268193
0.9355	High Similarity	NPC326592
0.9355	High Similarity	NPC112701
0.9325	High Similarity	NPC168789
0.9299	High Similarity	NPC287789
0.9299	High Similarity	NPC1796
0.9299	High Similarity	NPC271741
0.9299	High Similarity	NPC257166
0.9295	High Similarity	NPC304745
0.9295	High Similarity	NPC66441
0.9295	High Similarity	NPC111341
0.9295	High Similarity	NPC182555
0.929	High Similarity	NPC217149
0.929	High Similarity	NPC216035
0.929	High Similarity	NPC174086
0.9259	High Similarity	NPC53252
0.9255	High Similarity	NPC320741
0.9255	High Similarity	NPC171985
0.9245	High Similarity	NPC97812
0.9241	High Similarity	NPC15815
0.9241	High Similarity	NPC51760
0.9236	High Similarity	NPC215917
0.9236	High Similarity	NPC146636
0.9236	High Similarity	NPC20530
0.9236	High Similarity	NPC10754
0.9231	High Similarity	NPC121568
0.9226	High Similarity	NPC262039
0.9226	High Similarity	NPC262038
0.9226	High Similarity	NPC477897
0.9226	High Similarity	NPC254412
0.9226	High Similarity	NPC289774
0.9226	High Similarity	NPC328740
0.9226	High Similarity	NPC278476
0.9226	High Similarity	NPC209846
0.9226	High Similarity	NPC319910
0.9198	High Similarity	NPC260266
0.9182	High Similarity	NPC98023
0.9182	High Similarity	NPC226462
0.9182	High Similarity	NPC42965
0.9172	High Similarity	NPC48579
0.9172	High Similarity	NPC207809
0.9172	High Similarity	NPC259710
0.9172	High Similarity	NPC476169
0.9172	High Similarity	NPC217706
0.9172	High Similarity	NPC304207
0.9167	High Similarity	NPC171651
0.9167	High Similarity	NPC243171
0.9167	High Similarity	NPC475790
0.9167	High Similarity	NPC161881
0.9167	High Similarity	NPC244583
0.9167	High Similarity	NPC138288
0.9167	High Similarity	NPC56232
0.9167	High Similarity	NPC10807
0.9167	High Similarity	NPC150123
0.9167	High Similarity	NPC210597
0.9167	High Similarity	NPC35567
0.9161	High Similarity	NPC105136
0.9156	High Similarity	NPC122894
0.9146	High Similarity	NPC477529
0.913	High Similarity	NPC290160
0.9125	High Similarity	NPC312273
0.9125	High Similarity	NPC301256
0.9119	High Similarity	NPC105584
0.9114	High Similarity	NPC78492
0.9114	High Similarity	NPC208152
0.9108	High Similarity	NPC203080
0.9108	High Similarity	NPC209760
0.9108	High Similarity	NPC100134
0.9108	High Similarity	NPC293286
0.9108	High Similarity	NPC248793
0.9108	High Similarity	NPC180301
0.9103	High Similarity	NPC474021
0.9103	High Similarity	NPC474023
0.9097	High Similarity	NPC3642
0.9085	High Similarity	NPC102277
0.9085	High Similarity	NPC279209
0.9074	High Similarity	NPC36916
0.9074	High Similarity	NPC58223
0.9074	High Similarity	NPC72787
0.9074	High Similarity	NPC125039
0.9074	High Similarity	NPC473010
0.9074	High Similarity	NPC7154
0.9074	High Similarity	NPC7688
0.9074	High Similarity	NPC36
0.9068	High Similarity	NPC477841
0.9068	High Similarity	NPC473011
0.9068	High Similarity	NPC259834
0.9068	High Similarity	NPC473012
0.9062	High Similarity	NPC195136
0.9057	High Similarity	NPC318527
0.9057	High Similarity	NPC324358
0.9057	High Similarity	NPC322459
0.9057	High Similarity	NPC323627
0.9057	High Similarity	NPC208258
0.9051	High Similarity	NPC471116
0.9051	High Similarity	NPC79375
0.9051	High Similarity	NPC37253
0.9051	High Similarity	NPC477958
0.9045	High Similarity	NPC208011
0.9045	High Similarity	NPC39154
0.9045	High Similarity	NPC78324
0.9045	High Similarity	NPC115601
0.9038	High Similarity	NPC124478
0.9038	High Similarity	NPC177308
0.9024	High Similarity	NPC475212
0.9012	High Similarity	NPC38591
0.9012	High Similarity	NPC473009
0.9006	High Similarity	NPC47923
0.9006	High Similarity	NPC142252
0.9006	High Similarity	NPC289771
0.9	High Similarity	NPC308265
0.8994	High Similarity	NPC471787
0.8994	High Similarity	NPC132111
0.8988	High Similarity	NPC324742
0.8987	High Similarity	NPC311579
0.8987	High Similarity	NPC194593
0.8987	High Similarity	NPC472583
0.8987	High Similarity	NPC223701
0.8987	High Similarity	NPC71061
0.8987	High Similarity	NPC469405
0.8987	High Similarity	NPC303485
0.8987	High Similarity	NPC7989
0.8987	High Similarity	NPC72425
0.8987	High Similarity	NPC236756
0.8987	High Similarity	NPC290830
0.8987	High Similarity	NPC88983
0.8981	High Similarity	NPC471229
0.8981	High Similarity	NPC316960
0.8981	High Similarity	NPC472420
0.8981	High Similarity	NPC472422
0.8981	High Similarity	NPC222713
0.8981	High Similarity	NPC309512
0.8981	High Similarity	NPC67322
0.8981	High Similarity	NPC148945
0.8981	High Similarity	NPC263384
0.8981	High Similarity	NPC111112
0.8981	High Similarity	NPC471676
0.8981	High Similarity	NPC178484
0.8981	High Similarity	NPC204561
0.8981	High Similarity	NPC78835
0.8981	High Similarity	NPC471677
0.8981	High Similarity	NPC317715
0.8981	High Similarity	NPC138299
0.8981	High Similarity	NPC244577
0.8974	High Similarity	NPC291746
0.8974	High Similarity	NPC139966
0.8974	High Similarity	NPC288840
0.8974	High Similarity	NPC473016
0.8974	High Similarity	NPC277032
0.8974	High Similarity	NPC307052
0.8974	High Similarity	NPC89442
0.8968	High Similarity	NPC40086
0.8968	High Similarity	NPC308200
0.8968	High Similarity	NPC176869
0.8968	High Similarity	NPC476182
0.8968	High Similarity	NPC122828
0.8968	High Similarity	NPC211466
0.8968	High Similarity	NPC3779
0.8968	High Similarity	NPC44721
0.8963	High Similarity	NPC476459
0.8963	High Similarity	NPC292233
0.8961	High Similarity	NPC49130
0.8961	High Similarity	NPC470136
0.8961	High Similarity	NPC208176
0.8961	High Similarity	NPC279417
0.8961	High Similarity	NPC142731
0.8961	High Similarity	NPC62290
0.8961	High Similarity	NPC470135
0.8961	High Similarity	NPC4152
0.8961	High Similarity	NPC306607
0.8961	High Similarity	NPC326506
0.8961	High Similarity	NPC39045
0.8957	High Similarity	NPC477840
0.8957	High Similarity	NPC62261
0.8951	High Similarity	NPC219927
0.8951	High Similarity	NPC131745

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 NPC63438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	413
0.1-0.2	893
0.2-0.3	1750
0.3-0.4	2646
0.4-0.5	1858
0.5-0.6	1026
0.6-0.7	372
0.7-0.8	138
0.8-0.85	35
0.85-0.9	15
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9074	High Similarity	NPD6168	Clinical (unspecified phase)
0.9074	High Similarity	NPD6166	Phase 2
0.9074	High Similarity	NPD6167	Clinical (unspecified phase)
0.9038	High Similarity	NPD4380	Phase 2
0.8931	High Similarity	NPD8443	Clinical (unspecified phase)
0.8909	High Similarity	NPD7804	Clinical (unspecified phase)
0.8889	High Similarity	NPD6959	Discontinued
0.882	High Similarity	NPD7075	Discontinued
0.8718	High Similarity	NPD4378	Clinical (unspecified phase)
0.8704	High Similarity	NPD4381	Clinical (unspecified phase)
0.869	High Similarity	NPD7993	Clinical (unspecified phase)
0.8634	High Similarity	NPD2393	Clinical (unspecified phase)
0.8634	High Similarity	NPD7096	Clinical (unspecified phase)
0.8614	High Similarity	NPD7852	Clinical (unspecified phase)
0.8571	High Similarity	NPD6801	Discontinued
0.8509	High Similarity	NPD7411	Suspended
0.8506	High Similarity	NPD1550	Clinical (unspecified phase)
0.8506	High Similarity	NPD1552	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6797	Phase 2
0.8457	Intermediate Similarity	NPD1934	Approved
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8421	Intermediate Similarity	NPD7251	Discontinued
0.8415	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD7074	Phase 3
0.8373	Intermediate Similarity	NPD5494	Approved
0.8372	Intermediate Similarity	NPD7808	Phase 3
0.8353	Intermediate Similarity	NPD7054	Approved
0.8324	Intermediate Similarity	NPD8312	Approved
0.8324	Intermediate Similarity	NPD8313	Approved
0.8304	Intermediate Similarity	NPD7472	Approved
0.8303	Intermediate Similarity	NPD7768	Phase 2
0.8266	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD5403	Approved
0.8242	Intermediate Similarity	NPD5402	Approved
0.8199	Intermediate Similarity	NPD1512	Approved
0.8193	Intermediate Similarity	NPD3882	Suspended
0.8187	Intermediate Similarity	NPD6799	Approved
0.8187	Intermediate Similarity	NPD3818	Discontinued
0.8182	Intermediate Similarity	NPD2801	Approved
0.8182	Intermediate Similarity	NPD7819	Suspended
0.8144	Intermediate Similarity	NPD3749	Approved
0.8141	Intermediate Similarity	NPD1510	Phase 2
0.8137	Intermediate Similarity	NPD5401	Approved
0.8133	Intermediate Similarity	NPD3817	Phase 2
0.8129	Intermediate Similarity	NPD7473	Discontinued
0.811	Intermediate Similarity	NPD6599	Discontinued
0.8103	Intermediate Similarity	NPD6559	Discontinued
0.8101	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD2796	Approved
0.8075	Intermediate Similarity	NPD1511	Approved
0.8072	Intermediate Similarity	NPD8455	Phase 2
0.8059	Intermediate Similarity	NPD6232	Discontinued
0.8035	Intermediate Similarity	NPD5844	Phase 1
0.7953	Intermediate Similarity	NPD3787	Discontinued
0.7885	Intermediate Similarity	NPD1240	Approved
0.7874	Intermediate Similarity	NPD3751	Discontinued
0.7871	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7390	Discontinued
0.7826	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD2800	Approved
0.7796	Intermediate Similarity	NPD6781	Approved
0.7796	Intermediate Similarity	NPD6780	Approved
0.7796	Intermediate Similarity	NPD6776	Approved
0.7796	Intermediate Similarity	NPD6779	Approved
0.7796	Intermediate Similarity	NPD6777	Approved
0.7796	Intermediate Similarity	NPD6778	Approved
0.7796	Intermediate Similarity	NPD6782	Approved
0.7785	Intermediate Similarity	NPD1607	Approved
0.7778	Intermediate Similarity	NPD3750	Approved
0.7751	Intermediate Similarity	NPD1465	Phase 2
0.7742	Intermediate Similarity	NPD4908	Phase 1
0.7692	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD8150	Discontinued
0.7672	Intermediate Similarity	NPD7435	Discontinued
0.7672	Intermediate Similarity	NPD7696	Phase 3
0.7672	Intermediate Similarity	NPD7698	Approved
0.7672	Intermediate Similarity	NPD7697	Approved
0.7669	Intermediate Similarity	NPD4628	Phase 3
0.7656	Intermediate Similarity	NPD8151	Discontinued
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7870	Phase 2
0.7632	Intermediate Similarity	NPD7871	Phase 2
0.7622	Intermediate Similarity	NPD4363	Phase 3
0.7622	Intermediate Similarity	NPD4360	Phase 2
0.7604	Intermediate Similarity	NPD7701	Phase 2
0.76	Intermediate Similarity	NPD3926	Phase 2
0.759	Intermediate Similarity	NPD2532	Approved
0.759	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2533	Approved
0.759	Intermediate Similarity	NPD2534	Approved
0.7578	Intermediate Similarity	NPD2799	Discontinued
0.7562	Intermediate Similarity	NPD6651	Approved
0.7546	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5953	Discontinued
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.7527	Intermediate Similarity	NPD6534	Approved
0.7527	Intermediate Similarity	NPD6535	Approved
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3226	Approved
0.7515	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD7699	Phase 2
0.75	Intermediate Similarity	NPD7700	Phase 2
0.75	Intermediate Similarity	NPD920	Approved
0.7487	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7801	Approved
0.7487	Intermediate Similarity	NPD7783	Phase 2
0.7486	Intermediate Similarity	NPD1247	Approved
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD2344	Approved
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7228	Approved
0.7469	Intermediate Similarity	NPD3748	Approved
0.7448	Intermediate Similarity	NPD8320	Phase 1
0.7448	Intermediate Similarity	NPD8319	Approved
0.7438	Intermediate Similarity	NPD1613	Approved
0.7438	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7874	Approved
0.7432	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7286	Phase 2
0.7423	Intermediate Similarity	NPD2935	Discontinued
0.7421	Intermediate Similarity	NPD6798	Discontinued
0.7421	Intermediate Similarity	NPD2313	Discontinued
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1610	Phase 2
0.7401	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7199	Phase 2
0.7381	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD919	Approved
0.7371	Intermediate Similarity	NPD7584	Approved
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6823	Phase 2
0.7329	Intermediate Similarity	NPD943	Approved
0.7326	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6099	Approved
0.7317	Intermediate Similarity	NPD6100	Approved
0.7305	Intermediate Similarity	NPD2309	Approved
0.7305	Intermediate Similarity	NPD6190	Approved
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1243	Approved
0.7284	Intermediate Similarity	NPD5124	Phase 1
0.7284	Intermediate Similarity	NPD6355	Discontinued
0.7284	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD6234	Discontinued
0.7267	Intermediate Similarity	NPD6233	Phase 2
0.7257	Intermediate Similarity	NPD4966	Approved
0.7257	Intermediate Similarity	NPD4967	Phase 2
0.7257	Intermediate Similarity	NPD4965	Approved
0.7247	Intermediate Similarity	NPD7229	Phase 3
0.7246	Intermediate Similarity	NPD7003	Approved
0.724	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2424	Discontinued
0.7219	Intermediate Similarity	NPD4287	Approved
0.7212	Intermediate Similarity	NPD5408	Approved
0.7212	Intermediate Similarity	NPD5404	Approved
0.7212	Intermediate Similarity	NPD5405	Approved
0.7212	Intermediate Similarity	NPD5406	Approved
0.7211	Intermediate Similarity	NPD4361	Phase 2
0.7211	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7097	Phase 1
0.7193	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD2403	Approved
0.7157	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7152	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5710	Approved
0.7151	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7240	Approved
0.7117	Intermediate Similarity	NPD4060	Phase 1
0.7107	Intermediate Similarity	NPD1203	Approved
0.7105	Intermediate Similarity	NPD6213	Phase 3
0.7105	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6212	Phase 3
0.7099	Intermediate Similarity	NPD3268	Approved
0.7081	Intermediate Similarity	NPD6832	Phase 2
0.7072	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2798	Approved
0.7045	Intermediate Similarity	NPD5761	Phase 2
0.7045	Intermediate Similarity	NPD5760	Phase 2
0.7037	Intermediate Similarity	NPD3027	Phase 3
0.7035	Intermediate Similarity	NPD6273	Approved
0.7032	Intermediate Similarity	NPD1548	Phase 1
0.7027	Intermediate Similarity	NPD7685	Pre-registration
0.7019	Intermediate Similarity	NPD2861	Phase 2
0.7	Intermediate Similarity	NPD2797	Approved
0.6995	Remote Similarity	NPD7177	Discontinued
0.6994	Remote Similarity	NPD3764	Approved
0.6989	Remote Similarity	NPD6844	Discontinued
0.6985	Remote Similarity	NPD7585	Approved
0.6982	Remote Similarity	NPD1652	Phase 2

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