NPASS Compound

Structure

CID149368 OpenBabel06191715522D 39 42 0 0 1 0 0 0 0 0999 V2000 1.6845 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5506 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4166 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8807 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8185 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6845 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0147 4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4166 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0147 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0646 -2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5506 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8807 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8185 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1486 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2826 4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1486 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 3.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6456 2.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6456 1.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7796 1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 1.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 4.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8736 -3.1915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7467 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2826 5.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2826 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 3.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 -2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -2.1970 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 -0.0475 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 13 2 0 0 0 0 2 6 2 0 0 0 0 2 13 1 0 0 0 0 3 8 2 0 0 0 0 3 13 1 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 27 1 0 0 0 0 11 26 1 0 0 0 0 11 28 1 0 0 0 0 12 26 1 0 0 0 0 12 36 1 0 0 0 0 14 29 1 0 0 0 0 15 37 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 30 2 0 0 0 0 18 31 1 0 0 0 0 19 10 1 1 0 0 0 19 20 1 0 0 0 0 19 38 1 0 0 0 0 20 21 1 0 0 0 0 20 32 1 6 0 0 0 21 22 1 0 0 0 0 21 33 1 1 0 0 0 22 24 1 0 0 0 0 22 39 1 6 0 0 0 23 25 1 0 0 0 0 23 26 1 6 0 0 0 23 34 1 0 0 0 0 24 37 1 1 0 0 0 24 38 1 0 0 0 0 25 36 1 0 0 0 0 25 39 1 1 0 0 0 26 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	550.17
Volume:	517.208
LogP:	0.827
LogD:	0.168
LogS:	-3.768
# Rotatable Bonds:	9
TPSA:	215.83
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.134
Synthetic Accessibility Score:	4.505
Fsp3:	0.423
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:	-6.237
MDCK Permeability:	8.112468094623182e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.895
Human Intestinal Absorption (HIA):	0.781
20% Bioavailability (F20%):	0.217
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.197
Plasma Protein Binding (PPB):	91.33727264404297%
Volume Distribution (VD):	0.464
Pgp-substrate:	4.435305595397949%

ADMET: Metabolism

CYP1A2-inhibitor:	0.14
CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.728
CYP3A4-substrate:	0.08

ADMET: Excretion

Clearance (CL):	2.859
Half-life (T1/2):	0.745

ADMET: Toxicity

hERG Blockers:	0.369
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.677
AMES Toxicity:	0.729
Rat Oral Acute Toxicity:	0.135
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.8
Carcinogencity:	0.788
Eye Corrosion:	0.003
Eye Irritation:	0.113
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC149368

Natural Product ID:	NPC149368
*Common Name:**	Isoliquiritin Apioside
IUPAC Name:	(E)-3-[4-[(2S,3R,4S,5S,6R)-3-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1-(2,4-dihydroxyphenyl)prop-2-en-1-one
Synonyms:	Isoliquiritin Apioside
Standard InCHIKey:	VMMVZVPAYFZNBM-SXSJKRSNSA-N
Standard InCHI:	InChI=1S/C26H30O13/c27-10-19-20(32)21(33)22(39-25-23(34)26(35,11-28)12-36-25)24(38-19)37-15-5-1-13(2-6-15)3-8-17(30)16-7-4-14(29)9-18(16)31/h1-9,19-25,27-29,31-35H,10-12H2/b8-3+/t19-,20-,21+,22-,23-,24-,25-,26+/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2)/C=C/C(=O)c2ccc(cc2O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@H]1OC[C@@]([C@@H]1O)(O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL599764
PubChem CID:	46232188
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides

*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
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Ki	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	12900.0	nM	PMID[556078]
NPT2	Others	Unspecified		Ki	=	14200.0	nM	PMID[556078]

☑ 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 NPC149368 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	388
0.1-0.2	1486
0.2-0.3	3467
0.3-0.4	8482
0.4-0.5	10148
0.5-0.6	4558
0.6-0.7	5773
0.7-0.8	6302
0.8-0.85	1657
0.85-0.9	368
0.9-0.95	60
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC265480
0.9801	High Similarity	NPC200708
0.98	High Similarity	NPC122809
0.9797	High Similarity	NPC259767
0.9797	High Similarity	NPC88484
0.9667	High Similarity	NPC99233
0.9664	High Similarity	NPC259182
0.9664	High Similarity	NPC121001
0.9603	High Similarity	NPC170475
0.96	High Similarity	NPC39360
0.96	High Similarity	NPC143851
0.96	High Similarity	NPC106625
0.96	High Similarity	NPC83283
0.96	High Similarity	NPC210003
0.96	High Similarity	NPC29763
0.9597	High Similarity	NPC23253
0.9545	High Similarity	NPC150164
0.9539	High Similarity	NPC156457
0.9539	High Similarity	NPC313163
0.9539	High Similarity	NPC43638
0.9539	High Similarity	NPC258035
0.9539	High Similarity	NPC197896
0.9539	High Similarity	NPC161749
0.9539	High Similarity	NPC288084
0.9539	High Similarity	NPC23817
0.9536	High Similarity	NPC72649
0.9536	High Similarity	NPC97052
0.9536	High Similarity	NPC95090
0.9536	High Similarity	NPC27408
0.9536	High Similarity	NPC169248
0.9536	High Similarity	NPC39351
0.9536	High Similarity	NPC26195
0.9477	High Similarity	NPC73511
0.9474	High Similarity	NPC203500
0.9474	High Similarity	NPC323593
0.9474	High Similarity	NPC127406
0.9474	High Similarity	NPC307938
0.9474	High Similarity	NPC206378
0.9423	High Similarity	NPC72016
0.9416	High Similarity	NPC271479
0.9416	High Similarity	NPC472320
0.9412	High Similarity	NPC78263
0.9412	High Similarity	NPC60966
0.9412	High Similarity	NPC6985
0.9412	High Similarity	NPC182634
0.9412	High Similarity	NPC135391
0.9412	High Similarity	NPC65003
0.9412	High Similarity	NPC473512
0.9412	High Similarity	NPC133671
0.9412	High Similarity	NPC77672
0.9412	High Similarity	NPC54802
0.9412	High Similarity	NPC44931
0.9412	High Similarity	NPC108831
0.9412	High Similarity	NPC129827
0.9412	High Similarity	NPC197304
0.94	High Similarity	NPC191154
0.94	High Similarity	NPC213723
0.9396	High Similarity	NPC199335
0.9355	High Similarity	NPC303913
0.9355	High Similarity	NPC477628
0.9355	High Similarity	NPC270675
0.9355	High Similarity	NPC210961
0.9355	High Similarity	NPC472994
0.9355	High Similarity	NPC477629
0.9355	High Similarity	NPC195685
0.9351	High Similarity	NPC320283
0.9351	High Similarity	NPC22062
0.9351	High Similarity	NPC473634
0.9351	High Similarity	NPC111929
0.9351	High Similarity	NPC470607
0.9351	High Similarity	NPC472459
0.9351	High Similarity	NPC138811
0.9351	High Similarity	NPC41121
0.9351	High Similarity	NPC308265
0.9346	High Similarity	NPC45165
0.9346	High Similarity	NPC261866
0.9338	High Similarity	NPC134819
0.9329	High Similarity	NPC218685
0.9329	High Similarity	NPC23084
0.9308	High Similarity	NPC212748
0.9304	High Similarity	NPC48640
0.9304	High Similarity	NPC149244
0.9295	High Similarity	NPC472876
0.9295	High Similarity	NPC93215
0.929	High Similarity	NPC470405
0.929	High Similarity	NPC142860
0.929	High Similarity	NPC306978
0.929	High Similarity	NPC271270
0.929	High Similarity	NPC471079
0.929	High Similarity	NPC187379
0.929	High Similarity	NPC304741
0.929	High Similarity	NPC97285
0.929	High Similarity	NPC246469
0.929	High Similarity	NPC136761
0.929	High Similarity	NPC473623
0.929	High Similarity	NPC153342
0.9286	High Similarity	NPC470606
0.9272	High Similarity	NPC106025
0.9272	High Similarity	NPC214454
0.9272	High Similarity	NPC477240
0.925	High Similarity	NPC235575
0.9236	High Similarity	NPC121703
0.9236	High Similarity	NPC471286
0.9236	High Similarity	NPC88043
0.9236	High Similarity	NPC183672
0.9236	High Similarity	NPC168822
0.9236	High Similarity	NPC80068
0.9231	High Similarity	NPC47923
0.9231	High Similarity	NPC139320
0.9231	High Similarity	NPC265885
0.9231	High Similarity	NPC297987
0.9231	High Similarity	NPC282169
0.9231	High Similarity	NPC129217
0.9231	High Similarity	NPC159579
0.9231	High Similarity	NPC85707
0.9231	High Similarity	NPC170052
0.9231	High Similarity	NPC215710
0.9231	High Similarity	NPC101636
0.9231	High Similarity	NPC224530
0.9231	High Similarity	NPC473438
0.9231	High Similarity	NPC163242
0.9231	High Similarity	NPC259957
0.9231	High Similarity	NPC476215
0.9231	High Similarity	NPC64305
0.9231	High Similarity	NPC181465
0.9231	High Similarity	NPC276377
0.9231	High Similarity	NPC173582
0.9231	High Similarity	NPC253788
0.9231	High Similarity	NPC135846
0.9231	High Similarity	NPC470125
0.9231	High Similarity	NPC216496
0.9231	High Similarity	NPC249281
0.9231	High Similarity	NPC116458
0.9231	High Similarity	NPC48093
0.9231	High Similarity	NPC246943
0.9226	High Similarity	NPC43761
0.9221	High Similarity	NPC17521
0.9221	High Similarity	NPC295613
0.9221	High Similarity	NPC473657
0.9216	High Similarity	NPC87304
0.9216	High Similarity	NPC268950
0.9216	High Similarity	NPC211158
0.9216	High Similarity	NPC108706
0.9216	High Similarity	NPC78021
0.9211	High Similarity	NPC190217
0.92	High Similarity	NPC302989
0.9187	High Similarity	NPC72249
0.9177	High Similarity	NPC165720
0.9177	High Similarity	NPC205824
0.9177	High Similarity	NPC85751
0.9177	High Similarity	NPC139060
0.9177	High Similarity	NPC19240
0.9177	High Similarity	NPC129264
0.9172	High Similarity	NPC190450
0.9172	High Similarity	NPC259834
0.9172	High Similarity	NPC189142
0.9172	High Similarity	NPC27942
0.9172	High Similarity	NPC131745
0.9172	High Similarity	NPC240306
0.9172	High Similarity	NPC127782
0.9172	High Similarity	NPC77660
0.9172	High Similarity	NPC298171
0.9172	High Similarity	NPC300537
0.9172	High Similarity	NPC475382
0.9172	High Similarity	NPC44947
0.9156	High Similarity	NPC470605
0.9156	High Similarity	NPC470603
0.9156	High Similarity	NPC470604
0.915	High Similarity	NPC473996
0.913	High Similarity	NPC261254
0.913	High Similarity	NPC245452
0.9119	High Similarity	NPC89809
0.9119	High Similarity	NPC67037
0.9119	High Similarity	NPC255615
0.9119	High Similarity	NPC473278
0.9119	High Similarity	NPC254306
0.9119	High Similarity	NPC260504
0.9114	High Similarity	NPC179198
0.9114	High Similarity	NPC191306
0.9114	High Similarity	NPC19709
0.9114	High Similarity	NPC88023
0.9114	High Similarity	NPC257566
0.9114	High Similarity	NPC270335
0.9114	High Similarity	NPC309025
0.9114	High Similarity	NPC473644
0.9114	High Similarity	NPC29830
0.9114	High Similarity	NPC243930
0.9114	High Similarity	NPC66087
0.9114	High Similarity	NPC311850
0.9114	High Similarity	NPC124155
0.9114	High Similarity	NPC278419
0.9103	High Similarity	NPC104677
0.9085	High Similarity	NPC474772
0.9085	High Similarity	NPC474744
0.9085	High Similarity	NPC244577
0.9085	High Similarity	NPC471676
0.9085	High Similarity	NPC472636
0.9085	High Similarity	NPC318424
0.9085	High Similarity	NPC472580
0.9085	High Similarity	NPC472420

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 NPC149368 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	806
0.2-0.3	1737
0.3-0.4	2670
0.4-0.5	2056
0.5-0.6	1074
0.6-0.7	317
0.7-0.8	135
0.8-0.85	23
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9539	High Similarity	NPD4381	Clinical (unspecified phase)
0.9182	High Similarity	NPD3818	Discontinued
0.8896	High Similarity	NPD4380	Phase 2
0.8889	High Similarity	NPD7804	Clinical (unspecified phase)
0.8889	High Similarity	NPD7054	Approved
0.8841	High Similarity	NPD6559	Discontinued
0.8834	High Similarity	NPD7472	Approved
0.8834	High Similarity	NPD7074	Phase 3
0.8792	High Similarity	NPD1549	Phase 2
0.878	High Similarity	NPD6797	Phase 2
0.8727	High Similarity	NPD7251	Discontinued
0.8725	High Similarity	NPD1552	Clinical (unspecified phase)
0.8725	High Similarity	NPD1550	Clinical (unspecified phase)
0.8679	High Similarity	NPD7075	Discontinued
0.8675	High Similarity	NPD7808	Phase 3
0.8675	High Similarity	NPD4338	Clinical (unspecified phase)
0.8544	High Similarity	NPD6801	Discontinued
0.8544	High Similarity	NPD1934	Approved
0.8506	High Similarity	NPD6799	Approved
0.8491	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD5403	Approved
0.8385	Intermediate Similarity	NPD3882	Suspended
0.8365	Intermediate Similarity	NPD7411	Suspended
0.8364	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6166	Phase 2
0.8364	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8333	Intermediate Similarity	NPD5401	Approved
0.8333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD2796	Approved
0.8272	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD1511	Approved
0.8261	Intermediate Similarity	NPD2801	Approved
0.821	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD5402	Approved
0.821	Intermediate Similarity	NPD3817	Phase 2
0.82	Intermediate Similarity	NPD1240	Approved
0.8187	Intermediate Similarity	NPD6599	Discontinued
0.8165	Intermediate Similarity	NPD1512	Approved
0.8148	Intermediate Similarity	NPD7819	Suspended
0.811	Intermediate Similarity	NPD3749	Approved
0.8092	Intermediate Similarity	NPD1607	Approved
0.8012	Intermediate Similarity	NPD5494	Approved
0.7966	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3751	Discontinued
0.7935	Intermediate Similarity	NPD1551	Phase 2
0.7929	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7584	Approved
0.7888	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD8313	Approved
0.7874	Intermediate Similarity	NPD8312	Approved
0.7857	Intermediate Similarity	NPD6959	Discontinued
0.7848	Intermediate Similarity	NPD4628	Phase 3
0.7848	Intermediate Similarity	NPD3750	Approved
0.784	Intermediate Similarity	NPD1653	Approved
0.7829	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3787	Discontinued
0.7785	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7199	Phase 2
0.7725	Intermediate Similarity	NPD7768	Phase 2
0.7711	Intermediate Similarity	NPD8455	Phase 2
0.7703	Intermediate Similarity	NPD1091	Approved
0.7688	Intermediate Similarity	NPD5844	Phase 1
0.7677	Intermediate Similarity	NPD1933	Approved
0.7673	Intermediate Similarity	NPD2800	Approved
0.7669	Intermediate Similarity	NPD920	Approved
0.7663	Intermediate Similarity	NPD6781	Approved
0.7663	Intermediate Similarity	NPD6776	Approved
0.7663	Intermediate Similarity	NPD6780	Approved
0.7663	Intermediate Similarity	NPD6782	Approved
0.7663	Intermediate Similarity	NPD6777	Approved
0.7663	Intermediate Similarity	NPD6778	Approved
0.7663	Intermediate Similarity	NPD6779	Approved
0.7657	Intermediate Similarity	NPD7685	Pre-registration
0.7654	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7033	Discontinued
0.764	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1203	Approved
0.761	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1465	Phase 2
0.7602	Intermediate Similarity	NPD6232	Discontinued
0.7584	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6832	Phase 2
0.7572	Intermediate Similarity	NPD7473	Discontinued
0.7562	Intermediate Similarity	NPD1243	Approved
0.7558	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2344	Approved
0.7546	Intermediate Similarity	NPD2534	Approved
0.7546	Intermediate Similarity	NPD2532	Approved
0.7546	Intermediate Similarity	NPD2533	Approved
0.7545	Intermediate Similarity	NPD37	Approved
0.754	Intermediate Similarity	NPD7435	Discontinued
0.7532	Intermediate Similarity	NPD3748	Approved
0.7529	Intermediate Similarity	NPD7228	Approved
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.7515	Intermediate Similarity	NPD4967	Phase 2
0.7515	Intermediate Similarity	NPD4966	Approved
0.7515	Intermediate Similarity	NPD4965	Approved
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7474	Intermediate Similarity	NPD7585	Approved
0.7457	Intermediate Similarity	NPD3926	Phase 2
0.7447	Intermediate Similarity	NPD7696	Phase 3
0.7447	Intermediate Similarity	NPD7697	Approved
0.7447	Intermediate Similarity	NPD7698	Approved
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7435	Intermediate Similarity	NPD8151	Discontinued
0.7427	Intermediate Similarity	NPD919	Approved
0.7421	Intermediate Similarity	NPD7583	Approved
0.7407	Intermediate Similarity	NPD7871	Phase 2
0.7407	Intermediate Similarity	NPD7870	Phase 2
0.7405	Intermediate Similarity	NPD6651	Approved
0.7394	Intermediate Similarity	NPD6823	Phase 2
0.7391	Intermediate Similarity	NPD6535	Approved
0.7391	Intermediate Similarity	NPD6534	Approved
0.7389	Intermediate Similarity	NPD943	Approved
0.7382	Intermediate Similarity	NPD7701	Phase 2
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7365	Intermediate Similarity	NPD7458	Discontinued
0.7362	Intermediate Similarity	NPD6190	Approved
0.7362	Intermediate Similarity	NPD2309	Approved
0.7358	Intermediate Similarity	NPD7783	Phase 2
0.7358	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1652	Phase 2
0.7341	Intermediate Similarity	NPD1247	Approved
0.7338	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7266	Discontinued
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7312	Intermediate Similarity	NPD2799	Discontinued
0.7306	Intermediate Similarity	NPD7874	Approved
0.7306	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD9717	Approved
0.7273	Intermediate Similarity	NPD7700	Phase 2
0.7273	Intermediate Similarity	NPD7699	Phase 2
0.7268	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7801	Approved
0.7267	Intermediate Similarity	NPD6100	Approved
0.7267	Intermediate Similarity	NPD6099	Approved
0.7262	Intermediate Similarity	NPD3226	Approved
0.7261	Intermediate Similarity	NPD6798	Discontinued
0.7244	Intermediate Similarity	NPD4908	Phase 1
0.7244	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2654	Approved
0.7237	Intermediate Similarity	NPD1610	Phase 2
0.7233	Intermediate Similarity	NPD230	Phase 1
0.7233	Intermediate Similarity	NPD5124	Phase 1
0.7233	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6233	Phase 2
0.7204	Intermediate Similarity	NPD4360	Phase 2
0.7204	Intermediate Similarity	NPD4363	Phase 3
0.7195	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2424	Discontinued
0.7176	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4287	Approved
0.7167	Intermediate Similarity	NPD7240	Approved
0.7157	Intermediate Similarity	NPD7930	Approved
0.7152	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD3764	Approved
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8319	Approved
0.7135	Intermediate Similarity	NPD8320	Phase 1
0.7126	Intermediate Similarity	NPD4662	Approved
0.7126	Intermediate Similarity	NPD4661	Approved
0.7125	Intermediate Similarity	NPD447	Suspended
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD422	Phase 1
0.7117	Intermediate Similarity	NPD2346	Discontinued
0.7108	Intermediate Similarity	NPD5058	Phase 3
0.7102	Intermediate Similarity	NPD5710	Approved
0.7102	Intermediate Similarity	NPD5711	Approved
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7097	Intermediate Similarity	NPD3225	Approved
0.7089	Intermediate Similarity	NPD3027	Phase 3
0.7086	Intermediate Similarity	NPD9545	Approved
0.7074	Intermediate Similarity	NPD4361	Phase 2
0.7074	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8150	Discontinued
0.7059	Intermediate Similarity	NPD6213	Phase 3
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6212	Phase 3
0.7056	Intermediate Similarity	NPD1729	Discontinued
0.7051	Intermediate Similarity	NPD2797	Approved
0.7048	Intermediate Similarity	NPD3887	Approved
0.7048	Intermediate Similarity	NPD2354	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