NPASS Compound

Structure

CID145467 OpenBabel06191715502D 33 35 0 0 1 0 0 0 0 0999 V2000 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 31 1 0 0 0 0 6 32 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 33 1 0 0 0 0 17 25 2 0 0 0 0 18 21 2 0 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 27 2 0 0 0 0 20 17 1 6 0 0 0 20 26 1 0 0 0 0 21 28 1 0 0 0 0 22 31 1 0 0 0 0 23 24 2 0 0 0 0 23 33 1 0 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 25 29 1 0 0 0 0 26 30 2 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.22
Volume:	478.892
LogP:	6.418
LogD:	3.863
LogS:	-4.09
# Rotatable Bonds:	7
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.54
Synthetic Accessibility Score:	3.697
Fsp3:	0.37
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.802
MDCK Permeability:	1.3787888747174293e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.42
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	91.89317321777344%
Volume Distribution (VD):	1.001
Pgp-substrate:	7.3946757316589355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.221
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.917
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.912
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.469
CYP2D6-substrate:	0.753
CYP3A4-inhibitor:	0.555
CYP3A4-substrate:	0.608

ADMET: Excretion

Clearance (CL):	12.589
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.852
Drug-inuced Liver Injury (DILI):	0.25
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.578
Maximum Recommended Daily Dose:	0.161
Skin Sensitization:	0.772
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.313
Respiratory Toxicity:	0.401

Download Data

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

Natural Product: NPC145467

Natural Product ID:	NPC145467
*Common Name:**	Licorisoflavan A
IUPAC Name:	(3R)-3-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-5,7-dimethoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	AXLJPECJCPNXRX-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C27H32O6/c1-15(2)7-9-18-21(28)12-11-17(25(18)29)20-14-33-23-13-22(31-5)19(10-8-16(3)4)27(32-6)24(23)26(20)30/h7-8,11-13,20,28-29H,9-10,14H2,1-6H3/t20-/m0/s1
SMILES:	COc1cc2OC[C@H](C(=O)c2c(c1CC=C(C)C)OC)c1ccc(c(c1O)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598721
PubChem CID:	46232311
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003525] 3'-prenylated isoflavanones

*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.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	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]
NPO22336	Glycyrrhiza aspera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22336	Glycyrrhiza aspera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22336	Glycyrrhiza aspera	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[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22336	Glycyrrhiza aspera	Species	Fabaceae	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
MIC	2
Others	3

Activity Type	# Activity
NON-MOLECULAR	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	30.0	%	PMID[506268]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBC	=	100.0	ug ml-1	PMID[506270]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	50.0	ug.mL-1	PMID[506270]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MBC	=	1.56	ug ml-1	PMID[506270]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	1.56	ug.mL-1	PMID[506270]

☑ 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 NPC145467 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	372
0.1-0.2	1447
0.2-0.3	3452
0.3-0.4	8603
0.4-0.5	10016
0.5-0.6	3509
0.6-0.7	5215
0.7-0.8	5448
0.8-0.85	2353
0.85-0.9	1502
0.9-0.95	682
0.95-1	98

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC308200
0.9859	High Similarity	NPC39195
0.979	High Similarity	NPC471114
0.9787	High Similarity	NPC271288
0.9787	High Similarity	NPC311144
0.9722	High Similarity	NPC29777
0.9722	High Similarity	NPC471115
0.9718	High Similarity	NPC299011
0.9716	High Similarity	NPC113770
0.9648	High Similarity	NPC473014
0.9648	High Similarity	NPC235217
0.9648	High Similarity	NPC303185
0.9648	High Similarity	NPC184649
0.958	High Similarity	NPC127059
0.958	High Similarity	NPC477955
0.958	High Similarity	NPC472629
0.958	High Similarity	NPC285630
0.9577	High Similarity	NPC85162
0.9577	High Similarity	NPC125894
0.9577	High Similarity	NPC278249
0.9577	High Similarity	NPC223812
0.9577	High Similarity	NPC185276
0.9577	High Similarity	NPC107177
0.9577	High Similarity	NPC81697
0.9577	High Similarity	NPC77794
0.9524	High Similarity	NPC209760
0.9524	High Similarity	NPC100134
0.9521	High Similarity	NPC178484
0.9517	High Similarity	NPC473016
0.9514	High Similarity	NPC300988
0.9514	High Similarity	NPC10990
0.951	High Similarity	NPC470890
0.951	High Similarity	NPC473013
0.951	High Similarity	NPC131568
0.951	High Similarity	NPC87486
0.951	High Similarity	NPC236766
0.951	High Similarity	NPC124780
0.951	High Similarity	NPC131579
0.951	High Similarity	NPC473015
0.951	High Similarity	NPC197252
0.9507	High Similarity	NPC324134
0.9507	High Similarity	NPC10937
0.9507	High Similarity	NPC40833
0.9507	High Similarity	NPC76372
0.9507	High Similarity	NPC125855
0.9507	High Similarity	NPC182852
0.9507	High Similarity	NPC161506
0.9507	High Similarity	NPC296917
0.9507	High Similarity	NPC37496
0.9507	High Similarity	NPC166934
0.9507	High Similarity	NPC194432
0.9507	High Similarity	NPC306829
0.9507	High Similarity	NPC167624
0.9507	High Similarity	NPC32739
0.9507	High Similarity	NPC76338
0.9507	High Similarity	NPC227579
0.9507	High Similarity	NPC223500
0.9507	High Similarity	NPC107572
0.9507	High Similarity	NPC78
0.9507	High Similarity	NPC166482
0.9507	High Similarity	NPC265040
0.9507	High Similarity	NPC228504
0.9507	High Similarity	NPC177354
0.9507	High Similarity	NPC64915
0.9507	High Similarity	NPC324436
0.9507	High Similarity	NPC1089
0.9507	High Similarity	NPC220998
0.9507	High Similarity	NPC202981
0.9507	High Similarity	NPC66515
0.9507	High Similarity	NPC328164
0.9507	High Similarity	NPC148757
0.9504	High Similarity	NPC129853
0.9504	High Similarity	NPC76445
0.9504	High Similarity	NPC284550
0.9456	High Similarity	NPC210597
0.9444	High Similarity	NPC187282
0.9444	High Similarity	NPC24136
0.9444	High Similarity	NPC290133
0.9441	High Similarity	NPC214166
0.9441	High Similarity	NPC143896
0.9441	High Similarity	NPC316816
0.9441	High Similarity	NPC149026
0.9441	High Similarity	NPC91560
0.9441	High Similarity	NPC75049
0.9441	High Similarity	NPC478086
0.9441	High Similarity	NPC39329
0.9441	High Similarity	NPC310130
0.9441	High Similarity	NPC175504
0.9441	High Similarity	NPC18585
0.9441	High Similarity	NPC164980
0.9441	High Similarity	NPC169591
0.9441	High Similarity	NPC68104
0.9441	High Similarity	NPC257097
0.9441	High Similarity	NPC166138
0.9441	High Similarity	NPC150408
0.9441	High Similarity	NPC106985
0.9441	High Similarity	NPC221432
0.9437	High Similarity	NPC96408
0.9437	High Similarity	NPC279650
0.9437	High Similarity	NPC248372
0.9437	High Similarity	NPC166689
0.9437	High Similarity	NPC324386
0.9437	High Similarity	NPC213322
0.9437	High Similarity	NPC4743
0.9437	High Similarity	NPC312391
0.9437	High Similarity	NPC110038
0.9437	High Similarity	NPC17170
0.9437	High Similarity	NPC3188
0.9437	High Similarity	NPC258630
0.9437	High Similarity	NPC156190
0.9437	High Similarity	NPC282300
0.9433	High Similarity	NPC316480
0.9392	High Similarity	NPC213608
0.9392	High Similarity	NPC1477
0.9388	High Similarity	NPC471677
0.9384	High Similarity	NPC470461
0.9384	High Similarity	NPC223988
0.9384	High Similarity	NPC266499
0.9384	High Similarity	NPC317492
0.9379	High Similarity	NPC296998
0.9379	High Similarity	NPC473077
0.9379	High Similarity	NPC283234
0.9375	High Similarity	NPC224714
0.9375	High Similarity	NPC209040
0.9375	High Similarity	NPC273538
0.9375	High Similarity	NPC216538
0.9375	High Similarity	NPC326500
0.9375	High Similarity	NPC234629
0.9375	High Similarity	NPC311741
0.9371	High Similarity	NPC297600
0.9371	High Similarity	NPC144499
0.9366	High Similarity	NPC159275
0.9366	High Similarity	NPC188243
0.9366	High Similarity	NPC69769
0.9366	High Similarity	NPC241100
0.9366	High Similarity	NPC110228
0.9366	High Similarity	NPC6407
0.9366	High Similarity	NPC477272
0.9362	High Similarity	NPC118813
0.9329	High Similarity	NPC476169
0.9329	High Similarity	NPC471116
0.9324	High Similarity	NPC217149
0.9324	High Similarity	NPC5871
0.9324	High Similarity	NPC138288
0.9324	High Similarity	NPC216035
0.932	High Similarity	NPC227122
0.932	High Similarity	NPC321896
0.932	High Similarity	NPC476185
0.932	High Similarity	NPC472633
0.9315	High Similarity	NPC266572
0.9315	High Similarity	NPC132592
0.9315	High Similarity	NPC160821
0.9315	High Similarity	NPC37135
0.9315	High Similarity	NPC296869
0.9315	High Similarity	NPC470460
0.9315	High Similarity	NPC186397
0.9315	High Similarity	NPC168085
0.931	High Similarity	NPC474161
0.931	High Similarity	NPC5820
0.931	High Similarity	NPC54577
0.931	High Similarity	NPC88964
0.931	High Similarity	NPC176229
0.931	High Similarity	NPC267375
0.931	High Similarity	NPC306488
0.931	High Similarity	NPC470132
0.931	High Similarity	NPC475052
0.931	High Similarity	NPC124729
0.931	High Similarity	NPC109183
0.931	High Similarity	NPC470131
0.931	High Similarity	NPC312973
0.931	High Similarity	NPC111786
0.931	High Similarity	NPC142405
0.931	High Similarity	NPC476088
0.931	High Similarity	NPC83357
0.931	High Similarity	NPC178343
0.931	High Similarity	NPC301276
0.931	High Similarity	NPC246948
0.931	High Similarity	NPC470133
0.931	High Similarity	NPC473078
0.931	High Similarity	NPC214774
0.931	High Similarity	NPC470647
0.931	High Similarity	NPC67805
0.931	High Similarity	NPC195621
0.931	High Similarity	NPC20488
0.931	High Similarity	NPC470134
0.9306	High Similarity	NPC11700
0.9306	High Similarity	NPC219915
0.9306	High Similarity	NPC293053
0.9306	High Similarity	NPC212932
0.9306	High Similarity	NPC9117
0.9306	High Similarity	NPC24821
0.9306	High Similarity	NPC190637
0.9301	High Similarity	NPC268204
0.9301	High Similarity	NPC52789
0.9301	High Similarity	NPC110969
0.9301	High Similarity	NPC26051
0.9301	High Similarity	NPC469404
0.9301	High Similarity	NPC55832
0.9296	High Similarity	NPC274784
0.9296	High Similarity	NPC301217

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 NPC145467 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	912
0.2-0.3	1488
0.3-0.4	2510
0.4-0.5	1981
0.5-0.6	1163
0.6-0.7	514
0.7-0.8	171
0.8-0.85	45
0.85-0.9	18
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9375	High Similarity	NPD4378	Clinical (unspecified phase)
0.9329	High Similarity	NPD8443	Clinical (unspecified phase)
0.9155	High Similarity	NPD1550	Clinical (unspecified phase)
0.9155	High Similarity	NPD1552	Clinical (unspecified phase)
0.9133	High Similarity	NPD2393	Clinical (unspecified phase)
0.9091	High Similarity	NPD1549	Phase 2
0.9007	High Similarity	NPD7819	Suspended
0.8954	High Similarity	NPD7075	Discontinued
0.8933	High Similarity	NPD4380	Phase 2
0.8882	High Similarity	NPD7096	Clinical (unspecified phase)
0.8881	High Similarity	NPD1510	Phase 2
0.8874	High Similarity	NPD7411	Suspended
0.8851	High Similarity	NPD7410	Clinical (unspecified phase)
0.8819	High Similarity	NPD2796	Approved
0.8816	High Similarity	NPD1934	Approved
0.8732	High Similarity	NPD1240	Approved
0.8662	High Similarity	NPD6959	Discontinued
0.8645	High Similarity	NPD7768	Phase 2
0.8639	High Similarity	NPD2800	Approved
0.8636	High Similarity	NPD2801	Approved
0.8616	High Similarity	NPD7852	Clinical (unspecified phase)
0.8611	High Similarity	NPD1607	Approved
0.8599	High Similarity	NPD5494	Approved
0.859	High Similarity	NPD4381	Clinical (unspecified phase)
0.8571	High Similarity	NPD7804	Clinical (unspecified phase)
0.8533	High Similarity	NPD1511	Approved
0.8452	Intermediate Similarity	NPD6801	Discontinued
0.8447	Intermediate Similarity	NPD7473	Discontinued
0.8421	Intermediate Similarity	NPD1512	Approved
0.8411	Intermediate Similarity	NPD6799	Approved
0.8408	Intermediate Similarity	NPD3882	Suspended
0.8389	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6166	Phase 2
0.8385	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD2799	Discontinued
0.8356	Intermediate Similarity	NPD6651	Approved
0.8355	Intermediate Similarity	NPD2534	Approved
0.8355	Intermediate Similarity	NPD2533	Approved
0.8355	Intermediate Similarity	NPD2532	Approved
0.8354	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3750	Approved
0.8323	Intermediate Similarity	NPD6599	Discontinued
0.8322	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7074	Phase 3
0.8261	Intermediate Similarity	NPD6232	Discontinued
0.8253	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD920	Approved
0.8232	Intermediate Similarity	NPD7286	Phase 2
0.8232	Intermediate Similarity	NPD7054	Approved
0.8228	Intermediate Similarity	NPD3817	Phase 2
0.8194	Intermediate Similarity	NPD4908	Phase 1
0.8188	Intermediate Similarity	NPD1551	Phase 2
0.8188	Intermediate Similarity	NPD6099	Approved
0.8188	Intermediate Similarity	NPD2935	Discontinued
0.8188	Intermediate Similarity	NPD6100	Approved
0.8182	Intermediate Similarity	NPD7472	Approved
0.8176	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3818	Discontinued
0.8133	Intermediate Similarity	NPD2344	Approved
0.8133	Intermediate Similarity	NPD5953	Discontinued
0.8117	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD1610	Phase 2
0.8084	Intermediate Similarity	NPD7251	Discontinued
0.8084	Intermediate Similarity	NPD6559	Discontinued
0.8082	Intermediate Similarity	NPD2313	Discontinued
0.8038	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7808	Phase 3
0.8026	Intermediate Similarity	NPD1243	Approved
0.8025	Intermediate Similarity	NPD3226	Approved
0.8024	Intermediate Similarity	NPD6797	Phase 2
0.8013	Intermediate Similarity	NPD2346	Discontinued
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3748	Approved
0.7989	Intermediate Similarity	NPD4360	Phase 2
0.7989	Intermediate Similarity	NPD4363	Phase 3
0.7987	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD2309	Approved
0.7898	Intermediate Similarity	NPD5403	Approved
0.7888	Intermediate Similarity	NPD5402	Approved
0.7857	Intermediate Similarity	NPD4628	Phase 3
0.7838	Intermediate Similarity	NPD3268	Approved
0.7832	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6832	Phase 2
0.7821	Intermediate Similarity	NPD7390	Discontinued
0.7818	Intermediate Similarity	NPD5710	Approved
0.7818	Intermediate Similarity	NPD5711	Approved
0.7818	Intermediate Similarity	NPD7229	Phase 3
0.7808	Intermediate Similarity	NPD2798	Approved
0.7771	Intermediate Similarity	NPD5401	Approved
0.7758	Intermediate Similarity	NPD1247	Approved
0.774	Intermediate Similarity	NPD4361	Phase 2
0.774	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1203	Approved
0.774	Intermediate Similarity	NPD2797	Approved
0.7733	Intermediate Similarity	NPD943	Approved
0.7716	Intermediate Similarity	NPD1465	Phase 2
0.7706	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7458	Discontinued
0.7682	Intermediate Similarity	NPD5124	Phase 1
0.7682	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1548	Phase 1
0.7674	Intermediate Similarity	NPD8312	Approved
0.7674	Intermediate Similarity	NPD8313	Approved
0.767	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD3926	Phase 2
0.7662	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4625	Phase 3
0.7647	Intermediate Similarity	NPD7033	Discontinued
0.7636	Intermediate Similarity	NPD919	Approved
0.76	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD9717	Approved
0.7534	Intermediate Similarity	NPD1608	Approved
0.7517	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD5760	Phase 2
0.75	Intermediate Similarity	NPD5761	Phase 2
0.75	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3266	Approved
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD4749	Approved
0.7467	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD422	Phase 1
0.7452	Intermediate Similarity	NPD2654	Approved
0.7451	Intermediate Similarity	NPD6355	Discontinued
0.7451	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD230	Phase 1
0.7443	Intermediate Similarity	NPD8434	Phase 2
0.7442	Intermediate Similarity	NPD1729	Discontinued
0.7439	Intermediate Similarity	NPD6844	Discontinued
0.7427	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7419	Intermediate Similarity	NPD4308	Phase 3
0.7419	Intermediate Similarity	NPD7584	Approved
0.7415	Intermediate Similarity	NPD3972	Approved
0.7412	Intermediate Similarity	NPD2403	Approved
0.7405	Intermediate Similarity	NPD7003	Approved
0.74	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3787	Discontinued
0.7394	Intermediate Similarity	NPD8455	Phase 2
0.7389	Intermediate Similarity	NPD2424	Discontinued
0.7383	Intermediate Similarity	NPD1470	Approved
0.7368	Intermediate Similarity	NPD3764	Approved
0.736	Intermediate Similarity	NPD4287	Approved
0.736	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6104	Discontinued
0.7349	Intermediate Similarity	NPD4288	Approved
0.7349	Intermediate Similarity	NPD2296	Approved
0.7347	Intermediate Similarity	NPD1201	Approved
0.7346	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8150	Discontinued
0.7338	Intermediate Similarity	NPD1933	Approved
0.7338	Intermediate Similarity	NPD447	Suspended
0.7337	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD7577	Discontinued
0.7333	Intermediate Similarity	NPD37	Approved
0.7329	Intermediate Similarity	NPD17	Approved
0.7325	Intermediate Similarity	NPD1471	Phase 3
0.7325	Intermediate Similarity	NPD6005	Phase 3
0.7325	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6004	Phase 3
0.7325	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6002	Phase 3
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.7315	Intermediate Similarity	NPD3225	Approved
0.731	Intermediate Similarity	NPD9545	Approved
0.7308	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4966	Approved
0.7305	Intermediate Similarity	NPD4965	Approved
0.7305	Intermediate Similarity	NPD4967	Phase 2
0.7288	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6780	Approved
0.7283	Intermediate Similarity	NPD6778	Approved
0.7283	Intermediate Similarity	NPD6777	Approved
0.7283	Intermediate Similarity	NPD6776	Approved
0.7283	Intermediate Similarity	NPD6779	Approved
0.7283	Intermediate Similarity	NPD6781	Approved
0.7283	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD5890	Approved
0.7273	Intermediate Similarity	NPD5889	Approved
0.7267	Intermediate Similarity	NPD1164	Approved
0.7261	Intermediate Similarity	NPD5405	Approved
0.7261	Intermediate Similarity	NPD4477	Approved
0.7261	Intermediate Similarity	NPD5406	Approved
0.7261	Intermediate Similarity	NPD5404	Approved
0.7261	Intermediate Similarity	NPD5408	Approved
0.7261	Intermediate Similarity	NPD4476	Approved
0.7258	Intermediate Similarity	NPD7698	Approved
0.7258	Intermediate Similarity	NPD7435	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