NPASS Compound

Structure

CID59841 OpenBabel06191715392D 26 29 0 0 1 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 6.0622 3.5000 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 1.7321 -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 3.4641 2.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 6.9282 3.0000 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 21 1 0 0 0 0 2 21 1 0 0 0 0 3 24 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 19 2 0 0 0 0 13 14 1 6 0 0 0 14 18 2 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 20 24 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	84.09
Volume:	103.776
LogP:	3.358
LogD:	3.059
LogS:	-3.297
# Rotatable Bonds:	0
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.422
Synthetic Accessibility Score:	1.573
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.264
MDCK Permeability:	2.0516297809081152e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.122

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.993
Plasma Protein Binding (PPB):	86.0199203491211%
Volume Distribution (VD):	1.726
Pgp-substrate:	13.26026439666748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.936
CYP1A2-substrate:	0.678
CYP2C19-inhibitor:	0.363
CYP2C19-substrate:	0.522
CYP2C9-inhibitor:	0.334
CYP2C9-substrate:	0.843
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	8.088
Half-life (T1/2):	0.336

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.036
Drug-inuced Liver Injury (DILI):	0.202
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.727
Carcinogencity:	0.277
Eye Corrosion:	0.99
Eye Irritation:	0.993
Respiratory Toxicity:	0.644

Download Data

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

Natural Product: NPC59841

Natural Product ID:	NPC59841
*Common Name:**	3'-Methoxyglabridin
IUPAC Name:	4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]-2-methoxybenzene-1,3-diol
Synonyms:	3'-Methoxyglabridin
Standard InCHIKey:	SBQBKTSYEKPBJF-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-21(2)9-8-15-17(26-21)7-4-12-10-13(11-25-19(12)15)14-5-6-16(22)20(24-3)18(14)23/h4-9,13,22-23H,10-11H2,1-3H3/t13-/m0/s1
SMILES:	CC1(C)C=Cc2c(ccc3C[C@@H](COc23)c2ccc(c(c2O)OC)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463948
PubChem CID:	15228663
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0003530] Pyranoisoflavonoids

*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.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[464564]

☑ 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 NPC59841 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	463
0.1-0.2	1631
0.2-0.3	4465
0.3-0.4	11988
0.4-0.5	6146
0.5-0.6	3975
0.6-0.7	6254
0.7-0.8	5934
0.8-0.85	1003
0.85-0.9	643
0.9-0.95	170
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475891
1.0	High Similarity	NPC2613
1.0	High Similarity	NPC204347
0.9776	High Similarity	NPC260741
0.9776	High Similarity	NPC70682
0.964	High Similarity	NPC21776
0.964	High Similarity	NPC16269
0.9632	High Similarity	NPC35216
0.9627	High Similarity	NPC162659
0.9627	High Similarity	NPC265433
0.9627	High Similarity	NPC248727
0.9627	High Similarity	NPC270456
0.9568	High Similarity	NPC233980
0.9565	High Similarity	NPC473108
0.9559	High Similarity	NPC259519
0.9496	High Similarity	NPC469557
0.9485	High Similarity	NPC25966
0.9485	High Similarity	NPC127218
0.9485	High Similarity	NPC319647
0.9485	High Similarity	NPC245207
0.9481	High Similarity	NPC474639
0.9481	High Similarity	NPC230734
0.9481	High Similarity	NPC227503
0.9478	High Similarity	NPC317380
0.9424	High Similarity	NPC93323
0.9424	High Similarity	NPC45257
0.9424	High Similarity	NPC280092
0.9424	High Similarity	NPC12641
0.9416	High Similarity	NPC309124
0.9416	High Similarity	NPC184797
0.9412	High Similarity	NPC276490
0.9412	High Similarity	NPC211549
0.9407	High Similarity	NPC112246
0.9407	High Similarity	NPC470356
0.9407	High Similarity	NPC474206
0.9407	High Similarity	NPC473413
0.9407	High Similarity	NPC121812
0.9407	High Similarity	NPC112939
0.9407	High Similarity	NPC151224
0.9407	High Similarity	NPC94750
0.9403	High Similarity	NPC92805
0.9403	High Similarity	NPC229442
0.9403	High Similarity	NPC168059
0.9362	High Similarity	NPC474397
0.9362	High Similarity	NPC101376
0.9353	High Similarity	NPC102044
0.9353	High Similarity	NPC47633
0.9353	High Similarity	NPC85264
0.9348	High Similarity	NPC87725
0.9348	High Similarity	NPC471389
0.9348	High Similarity	NPC263261
0.9343	High Similarity	NPC236306
0.9343	High Similarity	NPC232164
0.9343	High Similarity	NPC32630
0.9343	High Similarity	NPC473739
0.9338	High Similarity	NPC173660
0.9338	High Similarity	NPC269091
0.9338	High Similarity	NPC470802
0.9338	High Similarity	NPC302701
0.9338	High Similarity	NPC16435
0.9338	High Similarity	NPC306441
0.9328	High Similarity	NPC86655
0.9328	High Similarity	NPC202762
0.9328	High Similarity	NPC127624
0.9306	High Similarity	NPC160196
0.9296	High Similarity	NPC473876
0.9286	High Similarity	NPC50250
0.9286	High Similarity	NPC63879
0.9286	High Similarity	NPC469795
0.9281	High Similarity	NPC107161
0.927	High Similarity	NPC102904
0.927	High Similarity	NPC103976
0.927	High Similarity	NPC326797
0.927	High Similarity	NPC474282
0.927	High Similarity	NPC176051
0.927	High Similarity	NPC107551
0.9265	High Similarity	NPC260898
0.9265	High Similarity	NPC234333
0.9265	High Similarity	NPC195022
0.9265	High Similarity	NPC61946
0.9265	High Similarity	NPC47398
0.9265	High Similarity	NPC164787
0.9259	High Similarity	NPC11060
0.9254	High Similarity	NPC118683
0.9254	High Similarity	NPC244888
0.9254	High Similarity	NPC211413
0.9254	High Similarity	NPC68205
0.9254	High Similarity	NPC293203
0.9254	High Similarity	NPC164804
0.9236	High Similarity	NPC2745
0.9231	High Similarity	NPC211561
0.9209	High Similarity	NPC178054
0.9209	High Similarity	NPC265075
0.9209	High Similarity	NPC247291
0.9203	High Similarity	NPC471388
0.9197	High Similarity	NPC18189
0.9197	High Similarity	NPC234952
0.9197	High Similarity	NPC20829
0.9197	High Similarity	NPC262585
0.9191	High Similarity	NPC478085
0.9191	High Similarity	NPC106215
0.9179	High Similarity	NPC91291
0.9178	High Similarity	NPC159922
0.9178	High Similarity	NPC188578
0.9178	High Similarity	NPC80918
0.9172	High Similarity	NPC157783
0.9167	High Similarity	NPC195561
0.9167	High Similarity	NPC158784
0.9167	High Similarity	NPC477612
0.9155	High Similarity	NPC87794
0.9155	High Similarity	NPC260397
0.9155	High Similarity	NPC211758
0.9137	High Similarity	NPC234568
0.9137	High Similarity	NPC198038
0.9137	High Similarity	NPC27495
0.9137	High Similarity	NPC254759
0.9137	High Similarity	NPC160283
0.9137	High Similarity	NPC22317
0.913	High Similarity	NPC477938
0.9124	High Similarity	NPC256262
0.9118	High Similarity	NPC475840
0.9118	High Similarity	NPC77196
0.9118	High Similarity	NPC36661
0.9118	High Similarity	NPC263064
0.9103	High Similarity	NPC302915
0.9091	High Similarity	NPC82917
0.9091	High Similarity	NPC170103
0.9091	High Similarity	NPC108811
0.9091	High Similarity	NPC70409
0.9091	High Similarity	NPC18185
0.9091	High Similarity	NPC262911
0.9091	High Similarity	NPC294558
0.9091	High Similarity	NPC263940
0.9091	High Similarity	NPC58190
0.9091	High Similarity	NPC202742
0.9091	High Similarity	NPC236202
0.9091	High Similarity	NPC204770
0.9078	High Similarity	NPC81638
0.9071	High Similarity	NPC71046
0.9065	High Similarity	NPC475836
0.9065	High Similarity	NPC184613
0.9065	High Similarity	NPC292882
0.9065	High Similarity	NPC19869
0.9058	High Similarity	NPC29799
0.9058	High Similarity	NPC209985
0.9058	High Similarity	NPC472334
0.9058	High Similarity	NPC177160
0.9058	High Similarity	NPC10737
0.9058	High Similarity	NPC472336
0.9058	High Similarity	NPC54743
0.9058	High Similarity	NPC263367
0.9058	High Similarity	NPC156502
0.9058	High Similarity	NPC477939
0.9051	High Similarity	NPC187616
0.9051	High Similarity	NPC223008
0.9051	High Similarity	NPC225696
0.9051	High Similarity	NPC115335
0.9051	High Similarity	NPC124085
0.9051	High Similarity	NPC117048
0.9051	High Similarity	NPC296915
0.9051	High Similarity	NPC97834
0.9051	High Similarity	NPC49603
0.9051	High Similarity	NPC198154
0.9051	High Similarity	NPC170694
0.9051	High Similarity	NPC193026
0.9044	High Similarity	NPC253105
0.9044	High Similarity	NPC219876
0.9044	High Similarity	NPC185604
0.9044	High Similarity	NPC6451
0.9044	High Similarity	NPC61477
0.9044	High Similarity	NPC261619
0.9044	High Similarity	NPC201587
0.9044	High Similarity	NPC78770
0.9044	High Similarity	NPC126029
0.9044	High Similarity	NPC15658
0.9041	High Similarity	NPC325860
0.903	High Similarity	NPC28765
0.903	High Similarity	NPC38664
0.903	High Similarity	NPC46274
0.903	High Similarity	NPC226331
0.903	High Similarity	NPC53986
0.9028	High Similarity	NPC212142
0.9028	High Similarity	NPC227516
0.9028	High Similarity	NPC20757
0.9021	High Similarity	NPC96576
0.9014	High Similarity	NPC277951
0.9014	High Similarity	NPC317237
0.9014	High Similarity	NPC473845
0.9014	High Similarity	NPC44530
0.9	High Similarity	NPC291101
0.9	High Similarity	NPC266197
0.8993	High Similarity	NPC474687
0.8986	High Similarity	NPC472337
0.8986	High Similarity	NPC313081
0.8978	High Similarity	NPC85435
0.8978	High Similarity	NPC158331
0.8971	High Similarity	NPC220825
0.8971	High Similarity	NPC103799
0.8971	High Similarity	NPC232275
0.8971	High Similarity	NPC268266

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 NPC59841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	917
0.2-0.3	1829
0.3-0.4	2739
0.4-0.5	1595
0.5-0.6	898
0.6-0.7	631
0.7-0.8	146
0.8-0.85	7
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9044	High Similarity	NPD1613	Approved
0.9044	High Similarity	NPD1612	Clinical (unspecified phase)
0.903	High Similarity	NPD1529	Clinical (unspecified phase)
0.8955	High Similarity	NPD1530	Clinical (unspecified phase)
0.8897	High Similarity	NPD4907	Clinical (unspecified phase)
0.8824	High Similarity	NPD3027	Phase 3
0.875	High Similarity	NPD4908	Phase 1
0.8507	High Similarity	NPD1610	Phase 2
0.8417	Intermediate Similarity	NPD4625	Phase 3
0.8301	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD4749	Approved
0.8235	Intermediate Similarity	NPD1934	Approved
0.8227	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1548	Phase 1
0.8143	Intermediate Similarity	NPD2861	Phase 2
0.8065	Intermediate Similarity	NPD2801	Approved
0.8041	Intermediate Similarity	NPD6674	Discontinued
0.7986	Intermediate Similarity	NPD4060	Phase 1
0.7974	Intermediate Similarity	NPD1653	Approved
0.7962	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6166	Phase 2
0.795	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD5124	Phase 1
0.7931	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD3018	Phase 2
0.7862	Intermediate Similarity	NPD6234	Discontinued
0.7836	Intermediate Similarity	NPD5283	Phase 1
0.7829	Intermediate Similarity	NPD1511	Approved
0.7812	Intermediate Similarity	NPD5494	Approved
0.7805	Intermediate Similarity	NPD5844	Phase 1
0.7805	Intermediate Similarity	NPD7054	Approved
0.7758	Intermediate Similarity	NPD7472	Approved
0.7758	Intermediate Similarity	NPD7074	Phase 3
0.7756	Intermediate Similarity	NPD4380	Phase 2
0.7744	Intermediate Similarity	NPD7228	Approved
0.7736	Intermediate Similarity	NPD3882	Suspended
0.773	Intermediate Similarity	NPD2982	Phase 2
0.773	Intermediate Similarity	NPD2983	Phase 2
0.7727	Intermediate Similarity	NPD1512	Approved
0.7725	Intermediate Similarity	NPD7549	Discontinued
0.7687	Intermediate Similarity	NPD228	Approved
0.7676	Intermediate Similarity	NPD8651	Approved
0.7673	Intermediate Similarity	NPD3817	Phase 2
0.7662	Intermediate Similarity	NPD7447	Phase 1
0.7662	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD2981	Phase 2
0.7658	Intermediate Similarity	NPD37	Approved
0.7654	Intermediate Similarity	NPD7199	Phase 2
0.7636	Intermediate Similarity	NPD3818	Discontinued
0.7625	Intermediate Similarity	NPD4967	Phase 2
0.7625	Intermediate Similarity	NPD4966	Approved
0.7625	Intermediate Similarity	NPD4965	Approved
0.7619	Intermediate Similarity	NPD3620	Phase 2
0.7619	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1465	Phase 2
0.7606	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6797	Phase 2
0.76	Intermediate Similarity	NPD6099	Approved
0.76	Intermediate Similarity	NPD6100	Approved
0.7597	Intermediate Similarity	NPD7213	Phase 3
0.7597	Intermediate Similarity	NPD7212	Phase 2
0.7591	Intermediate Similarity	NPD6671	Approved
0.7584	Intermediate Similarity	NPD4538	Approved
0.7584	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4536	Approved
0.7569	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7251	Discontinued
0.7537	Intermediate Similarity	NPD3021	Approved
0.7537	Intermediate Similarity	NPD3022	Approved
0.7533	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6331	Phase 2
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7808	Phase 3
0.7515	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD1558	Phase 1
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7473	Discontinued
0.7469	Intermediate Similarity	NPD7075	Discontinued
0.7469	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD422	Phase 1
0.7465	Intermediate Similarity	NPD1091	Approved
0.7451	Intermediate Similarity	NPD1652	Phase 2
0.7436	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7266	Discontinued
0.7427	Intermediate Similarity	NPD8053	Approved
0.7427	Intermediate Similarity	NPD8054	Approved
0.7421	Intermediate Similarity	NPD4675	Approved
0.7421	Intermediate Similarity	NPD4678	Approved
0.7419	Intermediate Similarity	NPD5058	Phase 3
0.7417	Intermediate Similarity	NPD5960	Phase 3
0.7417	Intermediate Similarity	NPD5588	Approved
0.7403	Intermediate Similarity	NPD7466	Approved
0.7403	Intermediate Similarity	NPD3750	Approved
0.7396	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7819	Suspended
0.7381	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4578	Approved
0.7368	Intermediate Similarity	NPD7311	Approved
0.7368	Intermediate Similarity	NPD7310	Approved
0.7368	Intermediate Similarity	NPD7312	Approved
0.7368	Intermediate Similarity	NPD7313	Approved
0.7368	Intermediate Similarity	NPD4577	Approved
0.7362	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4005	Discontinued
0.7343	Intermediate Similarity	NPD3705	Approved
0.7341	Intermediate Similarity	NPD4663	Approved
0.7338	Intermediate Similarity	NPD5177	Phase 3
0.7338	Intermediate Similarity	NPD7157	Approved
0.7333	Intermediate Similarity	NPD6959	Discontinued
0.7333	Intermediate Similarity	NPD2684	Approved
0.7326	Intermediate Similarity	NPD7309	Approved
0.7325	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3540	Phase 1
0.732	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6696	Suspended
0.7305	Intermediate Similarity	NPD2489	Approved
0.7305	Intermediate Similarity	NPD27	Approved
0.7301	Intermediate Similarity	NPD7768	Phase 2
0.7299	Intermediate Similarity	NPD7906	Approved
0.7297	Intermediate Similarity	NPD7095	Approved
0.729	Intermediate Similarity	NPD3892	Phase 2
0.7283	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.7267	Intermediate Similarity	NPD7411	Suspended
0.7267	Intermediate Similarity	NPD6072	Discontinued
0.7255	Intermediate Similarity	NPD3539	Phase 1
0.7251	Intermediate Similarity	NPD7240	Approved
0.7251	Intermediate Similarity	NPD6559	Discontinued
0.7246	Intermediate Similarity	NPD2969	Approved
0.7246	Intermediate Similarity	NPD7843	Approved
0.7246	Intermediate Similarity	NPD2970	Approved
0.7237	Intermediate Similarity	NPD7097	Phase 1
0.7222	Intermediate Similarity	NPD6801	Discontinued
0.7219	Intermediate Similarity	NPD5735	Approved
0.7219	Intermediate Similarity	NPD6355	Discontinued
0.7215	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6584	Phase 3
0.7208	Intermediate Similarity	NPD5762	Approved
0.7208	Intermediate Similarity	NPD1375	Discontinued
0.7208	Intermediate Similarity	NPD5763	Approved
0.7197	Intermediate Similarity	NPD7124	Phase 2
0.719	Intermediate Similarity	NPD1510	Phase 2
0.7186	Intermediate Similarity	NPD3051	Approved
0.7186	Intermediate Similarity	NPD3787	Discontinued
0.7186	Intermediate Similarity	NPD7229	Phase 3
0.7178	Intermediate Similarity	NPD8455	Phase 2
0.7178	Intermediate Similarity	NPD5929	Approved
0.7163	Intermediate Similarity	NPD7340	Approved
0.7153	Intermediate Similarity	NPD4750	Phase 3
0.7152	Intermediate Similarity	NPD2238	Phase 2
0.7152	Intermediate Similarity	NPD7041	Phase 2
0.7152	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD2796	Approved
0.7143	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5402	Approved
0.7134	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2677	Approved
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7132	Intermediate Similarity	NPD290	Approved
0.7107	Intermediate Similarity	NPD4123	Phase 3
0.7101	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6516	Phase 2
0.7083	Intermediate Similarity	NPD5846	Approved
0.7078	Intermediate Similarity	NPD3748	Approved
0.7078	Intermediate Similarity	NPD7033	Discontinued
0.7076	Intermediate Similarity	NPD8156	Discontinued
0.7071	Intermediate Similarity	NPD1398	Phase 1
0.707	Intermediate Similarity	NPD4110	Phase 3
0.707	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4535	Phase 3
0.7059	Intermediate Similarity	NPD4097	Suspended
0.7059	Intermediate Similarity	NPD968	Approved
0.7052	Intermediate Similarity	NPD7685	Pre-registration
0.7051	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4357	Discontinued
0.7044	Intermediate Similarity	NPD6799	Approved
0.7044	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2935	Discontinued
0.7029	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6190	Approved
0.7024	Intermediate Similarity	NPD1247	Approved
0.7024	Intermediate Similarity	NPD8127	Discontinued
0.702	Intermediate Similarity	NPD3268	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