NPASS Compound

Structure

CID5871 OpenBabel06191715332D 31 34 0 0 0 0 0 0 0 0999 V2000 5.1894 2.5309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6723 4.1237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5141 -4.4930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7571 -4.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7978 -2.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5514 2.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6352 -2.9716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3502 1.9337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5136 -2.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6755 1.9341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6751 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3503 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6752 1.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4710 3.1780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6355 -3.9860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5127 1.4505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5133 -1.4498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8376 1.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8375 1.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5125 0.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3506 -0.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8374 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5128 0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6756 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6759 -0.9665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8377 0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3785 -0.0172 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2292 -1.4731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7975 -1.4740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5127 1.4515 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 29 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 20 2 0 0 0 0 11 22 1 0 0 0 0 12 21 2 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 30 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 17 25 2 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 26 2 0 0 0 0 20 27 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 30 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 25 29 1 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.19
Volume:	444.249
LogP:	6.933
LogD:	4.482
LogS:	-4.253
# Rotatable Bonds:	5
TPSA:	72.06
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	3.292
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.973
MDCK Permeability:	1.3988342288939748e-05
Pgp-inhibitor:	0.946
Pgp-substrate:	0.405
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.562

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	85.70987701416016%
Volume Distribution (VD):	2.352
Pgp-substrate:	13.469587326049805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.52
CYP1A2-substrate:	0.48
CYP2C19-inhibitor:	0.902
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.73
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.381
CYP2D6-substrate:	0.791
CYP3A4-inhibitor:	0.287
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	13.876
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.968
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.691
Maximum Recommended Daily Dose:	0.77
Skin Sensitization:	0.78
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.646
Respiratory Toxicity:	0.803

Download Data

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

Natural Product: NPC5871

Natural Product ID:	NPC5871
*Common Name:**	Glycyrrhizol A
IUPAC Name:	1-methoxy-2,8-bis(3-methylbut-2-enyl)-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
Synonyms:
Standard InCHIKey:	CBPFOSMNDISZLV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H28O5/c1-14(2)6-8-16-10-18-19-13-30-23-12-21(28)17(9-7-15(3)4)25(29-5)24(23)26(19)31-22(18)11-20(16)27/h6-7,10-12,27-28H,8-9,13H2,1-5H3
SMILES:	CC(=CCc1cc2c3COc4cc(c(CC=C(C)C)c(c4-c3oc2cc1O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522282
PubChem CID:	11546269
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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]
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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	Activity	=	1.0	ug ml-1	PMID[520879]

☑ 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 NPC5871 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	381
0.1-0.2	1552
0.2-0.3	3591
0.3-0.4	9069
0.4-0.5	9657
0.5-0.6	3676
0.6-0.7	5529
0.7-0.8	4837
0.8-0.85	2218
0.85-0.9	1671
0.9-0.95	491
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC213608
0.9932	High Similarity	NPC1477
0.9732	High Similarity	NPC65504
0.9667	High Similarity	NPC40583
0.9658	High Similarity	NPC226644
0.9658	High Similarity	NPC37226
0.9589	High Similarity	NPC135325
0.9533	High Similarity	NPC160015
0.9533	High Similarity	NPC247677
0.953	High Similarity	NPC183874
0.953	High Similarity	NPC122365
0.9527	High Similarity	NPC170169
0.9524	High Similarity	NPC39929
0.9524	High Similarity	NPC178202
0.9524	High Similarity	NPC296030
0.9521	High Similarity	NPC130581
0.9521	High Similarity	NPC12148
0.9474	High Similarity	NPC260296
0.9474	High Similarity	NPC115432
0.947	High Similarity	NPC296957
0.947	High Similarity	NPC260902
0.9467	High Similarity	NPC198490
0.9467	High Similarity	NPC148938
0.9459	High Similarity	NPC78335
0.9459	High Similarity	NPC230713
0.9456	High Similarity	NPC39195
0.9452	High Similarity	NPC51641
0.9452	High Similarity	NPC210826
0.9452	High Similarity	NPC300267
0.9412	High Similarity	NPC30655
0.9412	High Similarity	NPC74854
0.9412	High Similarity	NPC45124
0.9408	High Similarity	NPC244750
0.9408	High Similarity	NPC476349
0.9408	High Similarity	NPC476350
0.9404	High Similarity	NPC180924
0.94	High Similarity	NPC235333
0.94	High Similarity	NPC472462
0.9396	High Similarity	NPC58668
0.9396	High Similarity	NPC106372
0.9392	High Similarity	NPC37208
0.9392	High Similarity	NPC317492
0.9392	High Similarity	NPC221868
0.9388	High Similarity	NPC17816
0.9388	High Similarity	NPC308200
0.9384	High Similarity	NPC230943
0.9355	High Similarity	NPC37183
0.9342	High Similarity	NPC246647
0.9342	High Similarity	NPC96342
0.9342	High Similarity	NPC268360
0.9342	High Similarity	NPC164110
0.9342	High Similarity	NPC212967
0.9338	High Similarity	NPC213936
0.9338	High Similarity	NPC297531
0.9333	High Similarity	NPC207624
0.9333	High Similarity	NPC67654
0.9333	High Similarity	NPC263676
0.9324	High Similarity	NPC145467
0.9324	High Similarity	NPC168085
0.9324	High Similarity	NPC272194
0.932	High Similarity	NPC299011
0.9315	High Similarity	NPC225884
0.9315	High Similarity	NPC302181
0.9295	High Similarity	NPC277480
0.929	High Similarity	NPC109180
0.929	High Similarity	NPC155640
0.929	High Similarity	NPC472581
0.929	High Similarity	NPC38591
0.9267	High Similarity	NPC116604
0.9267	High Similarity	NPC115324
0.9267	High Similarity	NPC156244
0.9267	High Similarity	NPC23668
0.9267	High Similarity	NPC193976
0.9262	High Similarity	NPC471114
0.9252	High Similarity	NPC303185
0.9252	High Similarity	NPC470890
0.9252	High Similarity	NPC271288
0.9252	High Similarity	NPC311144
0.9252	High Similarity	NPC184649
0.9247	High Similarity	NPC53192
0.9236	High Similarity	NPC476459
0.9226	High Similarity	NPC219861
0.9221	High Similarity	NPC220582
0.9221	High Similarity	NPC304839
0.9216	High Similarity	NPC196448
0.9211	High Similarity	NPC99199
0.9205	High Similarity	NPC253872
0.9205	High Similarity	NPC473996
0.9205	High Similarity	NPC142308
0.92	High Similarity	NPC167576
0.92	High Similarity	NPC476185
0.92	High Similarity	NPC29777
0.92	High Similarity	NPC321896
0.92	High Similarity	NPC471115
0.9189	High Similarity	NPC24136
0.9189	High Similarity	NPC187282
0.9189	High Similarity	NPC290133
0.9189	High Similarity	NPC472629
0.9189	High Similarity	NPC477955
0.9184	High Similarity	NPC18585
0.9184	High Similarity	NPC310130
0.9184	High Similarity	NPC113770
0.9184	High Similarity	NPC166138
0.9184	High Similarity	NPC221432
0.9184	High Similarity	NPC106985
0.9184	High Similarity	NPC257097
0.9184	High Similarity	NPC68104
0.9184	High Similarity	NPC164980
0.9184	High Similarity	NPC91560
0.9184	High Similarity	NPC149026
0.9184	High Similarity	NPC175504
0.9184	High Similarity	NPC150408
0.9184	High Similarity	NPC75049
0.9184	High Similarity	NPC143896
0.9184	High Similarity	NPC39329
0.9184	High Similarity	NPC169591
0.9178	High Similarity	NPC17170
0.9178	High Similarity	NPC166689
0.9178	High Similarity	NPC96408
0.9178	High Similarity	NPC3188
0.9178	High Similarity	NPC258630
0.9178	High Similarity	NPC156190
0.9178	High Similarity	NPC279650
0.9145	High Similarity	NPC72370
0.9139	High Similarity	NPC472580
0.9139	High Similarity	NPC472636
0.9133	High Similarity	NPC266499
0.9128	High Similarity	NPC300988
0.9128	High Similarity	NPC10990
0.9122	High Similarity	NPC98926
0.9122	High Similarity	NPC197252
0.9122	High Similarity	NPC473015
0.9122	High Similarity	NPC209040
0.9122	High Similarity	NPC124780
0.9122	High Similarity	NPC234629
0.9122	High Similarity	NPC155144
0.9122	High Similarity	NPC236766
0.9122	High Similarity	NPC224714
0.9122	High Similarity	NPC87486
0.9122	High Similarity	NPC473013
0.9122	High Similarity	NPC311741
0.9119	High Similarity	NPC120220
0.9119	High Similarity	NPC131866
0.9116	High Similarity	NPC66515
0.9116	High Similarity	NPC107572
0.9116	High Similarity	NPC161506
0.9116	High Similarity	NPC37496
0.9116	High Similarity	NPC78
0.9116	High Similarity	NPC166482
0.9116	High Similarity	NPC306829
0.9116	High Similarity	NPC40833
0.9116	High Similarity	NPC76338
0.9116	High Similarity	NPC177354
0.9116	High Similarity	NPC202981
0.9116	High Similarity	NPC470636
0.9116	High Similarity	NPC125855
0.9116	High Similarity	NPC76372
0.9116	High Similarity	NPC166934
0.9116	High Similarity	NPC194432
0.9116	High Similarity	NPC148757
0.9116	High Similarity	NPC144499
0.9116	High Similarity	NPC296917
0.9116	High Similarity	NPC1089
0.9116	High Similarity	NPC328164
0.9116	High Similarity	NPC226942
0.9116	High Similarity	NPC228504
0.9116	High Similarity	NPC10937
0.9116	High Similarity	NPC220998
0.9116	High Similarity	NPC96791
0.9116	High Similarity	NPC167624
0.9116	High Similarity	NPC32739
0.9116	High Similarity	NPC64915
0.9116	High Similarity	NPC227579
0.9116	High Similarity	NPC265040
0.9116	High Similarity	NPC324436
0.9116	High Similarity	NPC223500
0.9116	High Similarity	NPC324134
0.9116	High Similarity	NPC182852
0.9114	High Similarity	NPC320789
0.911	High Similarity	NPC69769
0.911	High Similarity	NPC253822
0.9103	High Similarity	NPC193998
0.9079	High Similarity	NPC31627
0.9079	High Similarity	NPC477957
0.9079	High Similarity	NPC41326
0.9079	High Similarity	NPC476238
0.9079	High Similarity	NPC210597
0.9079	High Similarity	NPC327269
0.9073	High Similarity	NPC135303
0.9073	High Similarity	NPC472406
0.9073	High Similarity	NPC148423
0.9073	High Similarity	NPC472421
0.9067	High Similarity	NPC186397
0.9067	High Similarity	NPC37135
0.9067	High Similarity	NPC266572
0.9062	High Similarity	NPC472584
0.906	High Similarity	NPC470133
0.906	High Similarity	NPC473078
0.906	High Similarity	NPC470134
0.906	High Similarity	NPC470132

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 NPC5871 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	941
0.2-0.3	1510
0.3-0.4	2563
0.4-0.5	2023
0.5-0.6	1165
0.6-0.7	408
0.7-0.8	138
0.8-0.85	46
0.85-0.9	25
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8993	High Similarity	NPD4378	Clinical (unspecified phase)
0.8846	High Similarity	NPD3749	Approved
0.8844	High Similarity	NPD1549	Phase 2
0.8839	High Similarity	NPD8443	Clinical (unspecified phase)
0.8776	High Similarity	NPD1552	Clinical (unspecified phase)
0.8776	High Similarity	NPD1550	Clinical (unspecified phase)
0.8774	High Similarity	NPD2393	Clinical (unspecified phase)
0.8766	High Similarity	NPD7411	Suspended
0.8742	High Similarity	NPD7410	Clinical (unspecified phase)
0.8701	High Similarity	NPD4380	Phase 2
0.8679	High Similarity	NPD6959	Discontinued
0.8658	High Similarity	NPD2800	Approved
0.8654	High Similarity	NPD7819	Suspended
0.8649	High Similarity	NPD2344	Approved
0.8639	High Similarity	NPD1510	Phase 2
0.8634	High Similarity	NPD7852	Clinical (unspecified phase)
0.8627	High Similarity	NPD920	Approved
0.8608	High Similarity	NPD7075	Discontinued
0.8581	High Similarity	NPD2796	Approved
0.8545	High Similarity	NPD6559	Discontinued
0.8544	High Similarity	NPD7768	Phase 2
0.8535	High Similarity	NPD7096	Clinical (unspecified phase)
0.8533	High Similarity	NPD1243	Approved
0.85	High Similarity	NPD5494	Approved
0.8497	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1240	Approved
0.8471	Intermediate Similarity	NPD1934	Approved
0.8428	Intermediate Similarity	NPD3882	Suspended
0.8421	Intermediate Similarity	NPD2309	Approved
0.8378	Intermediate Similarity	NPD1607	Approved
0.8377	Intermediate Similarity	NPD2532	Approved
0.8377	Intermediate Similarity	NPD2533	Approved
0.8377	Intermediate Similarity	NPD2534	Approved
0.8375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD2801	Approved
0.8289	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6801	Discontinued
0.8199	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1511	Approved
0.8194	Intermediate Similarity	NPD6799	Approved
0.8193	Intermediate Similarity	NPD3818	Discontinued
0.8182	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6232	Discontinued
0.8144	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7473	Discontinued
0.8121	Intermediate Similarity	NPD3926	Phase 2
0.8117	Intermediate Similarity	NPD3750	Approved
0.8113	Intermediate Similarity	NPD6599	Discontinued
0.811	Intermediate Similarity	NPD1247	Approved
0.8089	Intermediate Similarity	NPD1512	Approved
0.8059	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8026	Intermediate Similarity	NPD2799	Discontinued
0.7988	Intermediate Similarity	NPD919	Approved
0.7987	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2935	Discontinued
0.7974	Intermediate Similarity	NPD1551	Phase 2
0.7941	Intermediate Similarity	NPD5953	Discontinued
0.7929	Intermediate Similarity	NPD7286	Phase 2
0.7914	Intermediate Similarity	NPD3817	Phase 2
0.7908	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6651	Approved
0.7882	Intermediate Similarity	NPD7074	Phase 3
0.7867	Intermediate Similarity	NPD2313	Discontinued
0.7867	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD4908	Phase 1
0.7848	Intermediate Similarity	NPD7390	Discontinued
0.7844	Intermediate Similarity	NPD5710	Approved
0.7844	Intermediate Similarity	NPD5711	Approved
0.7826	Intermediate Similarity	NPD3226	Approved
0.7824	Intermediate Similarity	NPD7054	Approved
0.7806	Intermediate Similarity	NPD2346	Discontinued
0.7805	Intermediate Similarity	NPD2296	Approved
0.7792	Intermediate Similarity	NPD3748	Approved
0.7784	Intermediate Similarity	NPD4287	Approved
0.7778	Intermediate Similarity	NPD7472	Approved
0.7771	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1465	Phase 2
0.7742	Intermediate Similarity	NPD6100	Approved
0.7742	Intermediate Similarity	NPD6099	Approved
0.7738	Intermediate Similarity	NPD7229	Phase 3
0.7733	Intermediate Similarity	NPD6797	Phase 2
0.7733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD5403	Approved
0.7697	Intermediate Similarity	NPD5402	Approved
0.7688	Intermediate Similarity	NPD7251	Discontinued
0.7683	Intermediate Similarity	NPD6279	Approved
0.7683	Intermediate Similarity	NPD6280	Approved
0.7658	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7644	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7808	Phase 3
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7619	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4360	Phase 2
0.7611	Intermediate Similarity	NPD4363	Phase 3
0.758	Intermediate Similarity	NPD1471	Phase 3
0.7578	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5401	Approved
0.7572	Intermediate Similarity	NPD1729	Discontinued
0.7569	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4361	Phase 2
0.7533	Intermediate Similarity	NPD1203	Approved
0.7532	Intermediate Similarity	NPD943	Approved
0.753	Intermediate Similarity	NPD5761	Phase 2
0.753	Intermediate Similarity	NPD5760	Phase 2
0.7529	Intermediate Similarity	NPD6808	Phase 2
0.7516	Intermediate Similarity	NPD3764	Approved
0.7515	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2654	Approved
0.7483	Intermediate Similarity	NPD2798	Approved
0.7472	Intermediate Similarity	NPD8434	Phase 2
0.7452	Intermediate Similarity	NPD7033	Discontinued
0.7451	Intermediate Similarity	NPD4625	Phase 3
0.7405	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3268	Approved
0.7401	Intermediate Similarity	NPD8312	Approved
0.7401	Intermediate Similarity	NPD8313	Approved
0.7372	Intermediate Similarity	NPD230	Phase 1
0.7356	Intermediate Similarity	NPD3751	Discontinued
0.7347	Intermediate Similarity	NPD1548	Phase 1
0.7341	Intermediate Similarity	NPD2403	Approved
0.7337	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9717	Approved
0.7329	Intermediate Similarity	NPD7003	Approved
0.7303	Intermediate Similarity	NPD2797	Approved
0.7296	Intermediate Similarity	NPD5408	Approved
0.7296	Intermediate Similarity	NPD5404	Approved
0.7296	Intermediate Similarity	NPD5406	Approved
0.7296	Intermediate Similarity	NPD5405	Approved
0.7293	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7458	Discontinued
0.7288	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD8151	Discontinued
0.7267	Intermediate Similarity	NPD7199	Phase 2
0.7262	Intermediate Similarity	NPD37	Approved
0.7261	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5124	Phase 1
0.7251	Intermediate Similarity	NPD6234	Discontinued
0.7241	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4967	Phase 2
0.7235	Intermediate Similarity	NPD4965	Approved
0.7235	Intermediate Similarity	NPD4966	Approved
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.7225	Intermediate Similarity	NPD3787	Discontinued
0.7219	Intermediate Similarity	NPD8455	Phase 2
0.7219	Intermediate Similarity	NPD3972	Approved
0.7208	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2861	Phase 2
0.7205	Intermediate Similarity	NPD2424	Discontinued
0.7197	Intermediate Similarity	NPD1613	Approved
0.7197	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1470	Approved
0.719	Intermediate Similarity	NPD1164	Approved
0.7184	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4288	Approved
0.7173	Intermediate Similarity	NPD7584	Approved
0.7171	Intermediate Similarity	NPD4749	Approved
0.7161	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6844	Discontinued
0.7159	Intermediate Similarity	NPD7177	Discontinued
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1933	Approved
0.7152	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD422	Phase 1
0.7151	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7128	Intermediate Similarity	NPD6778	Approved
0.7128	Intermediate Similarity	NPD6780	Approved
0.7128	Intermediate Similarity	NPD6776	Approved
0.7128	Intermediate Similarity	NPD6782	Approved
0.7128	Intermediate Similarity	NPD6777	Approved
0.7128	Intermediate Similarity	NPD6779	Approved
0.7128	Intermediate Similarity	NPD6781	Approved
0.7127	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9545	Approved
0.7105	Intermediate Similarity	NPD1608	Approved
0.7102	Intermediate Similarity	NPD3446	Phase 1
0.7101	Intermediate Similarity	NPD5889	Approved
0.7101	Intermediate Similarity	NPD5890	Approved
0.7095	Intermediate Similarity	NPD6104	Discontinued
0.7078	Intermediate Similarity	NPD3266	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