NPASS Compound

Structure

CID115432 OpenBabel06191715472D 28 31 0 0 0 0 0 0 0 0999 V2000 -0.0015 -5.9078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7447 -5.9082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5789 -2.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7043 -3.9155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8720 -4.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9944 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0010 -3.8915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1623 0.4797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1619 -1.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8325 -1.4418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8717 -5.4039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9942 -0.9625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3296 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0007 -2.8833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 -2.4027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3294 -0.9622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6648 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8319 -1.4422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8316 -2.4031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6646 -0.9618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8322 0.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8601 -1.4627 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8323 1.4803 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7059 -2.9065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 -2.9074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4972 -1.4425 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 12 23 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 25 1 0 0 0 0 16 27 1 0 0 0 0 17 19 2 0 0 0 0 17 28 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 24 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.13
Volume:	383.856
LogP:	5.571
LogD:	3.756
LogS:	-5.342
# Rotatable Bonds:	4
TPSA:	82.04
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	2.9
Fsp3:	0.227
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:	-4.844
MDCK Permeability:	1.959639848791994e-05
Pgp-inhibitor:	0.121
Pgp-substrate:	0.19
Human Intestinal Absorption (HIA):	0.088
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.806

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	75.8873519897461%
Volume Distribution (VD):	0.777
Pgp-substrate:	20.97865867614746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.847
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.226
CYP2C9-inhibitor:	0.885
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.412
CYP2D6-substrate:	0.854
CYP3A4-inhibitor:	0.436
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	8.745
Half-life (T1/2):	0.197

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.219
Rat Oral Acute Toxicity:	0.449
Maximum Recommended Daily Dose:	0.735
Skin Sensitization:	0.617
Carcinogencity:	0.233
Eye Corrosion:	0.003
Eye Irritation:	0.227
Respiratory Toxicity:	0.345

Download Data

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

Natural Product: NPC115432

Natural Product ID:	NPC115432
*Common Name:**	5-O-Methylglycryol
IUPAC Name:	9-hydroxy-1,3-dimethoxy-2-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one
Synonyms:	5-O-Methylglycryol
Standard InCHIKey:	ACDSUMGMZHXCRO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H20O6/c1-11(2)5-7-14-15(25-3)10-17-19(20(14)26-4)21-18(22(24)28-17)13-8-6-12(23)9-16(13)27-21/h5-6,8-10,23H,7H2,1-4H3
SMILES:	COc1cc2oc(=O)c3c(c2c(c1CC=C(C)C)OC)oc1c3ccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522369
PubChem CID:	5319666
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000354] Coumestans

*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]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24211545]
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]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	Urine	n.a.	n.a.	PMID[6330305]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	PMID[932730]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO17393	Bubalus bubalis	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17393	Bubalus bubalis	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17393	Bubalus bubalis	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12323	Bos taurus	Species	Bovidae	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]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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]

☑ 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	4

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	>	60.0	%	PMID[508908]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	80.0	%	PMID[508908]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	Activity	=	500.0	ug ml-1	PMID[508907]
NPT2	Others	Unspecified		Inhibition	>	40.0	%	PMID[508908]

☑ 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 NPC115432 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	387
0.1-0.2	1747
0.2-0.3	3945
0.3-0.4	9572
0.4-0.5	9026
0.5-0.6	4018
0.6-0.7	5847
0.7-0.8	4510
0.8-0.85	2464
0.85-0.9	974
0.9-0.95	193
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC260296
0.9934	High Similarity	NPC244750
0.9805	High Similarity	NPC155640
0.9603	High Similarity	NPC41326
0.9539	High Similarity	NPC213608
0.9539	High Similarity	NPC1477
0.9497	High Similarity	NPC120220
0.9494	High Similarity	NPC320789
0.9474	High Similarity	NPC5871
0.9437	High Similarity	NPC472584
0.9416	High Similarity	NPC13879
0.9416	High Similarity	NPC247677
0.9416	High Similarity	NPC160015
0.9404	High Similarity	NPC226644
0.9404	High Similarity	NPC37226
0.9379	High Similarity	NPC261471
0.9355	High Similarity	NPC260902
0.9355	High Similarity	NPC65504
0.9355	High Similarity	NPC296957
0.9338	High Similarity	NPC135325
0.9308	High Similarity	NPC323137
0.9295	High Similarity	NPC40583
0.9295	High Similarity	NPC476349
0.9295	High Similarity	NPC476350
0.9281	High Similarity	NPC170169
0.9272	High Similarity	NPC12148
0.9272	High Similarity	NPC130581
0.9255	High Similarity	NPC218533
0.9255	High Similarity	NPC78830
0.9245	High Similarity	NPC204088
0.9245	High Similarity	NPC329215
0.9245	High Similarity	NPC259007
0.9226	High Similarity	NPC148938
0.9221	High Similarity	NPC67654
0.9216	High Similarity	NPC230713
0.9216	High Similarity	NPC78335
0.9205	High Similarity	NPC51641
0.9205	High Similarity	NPC300267
0.9205	High Similarity	NPC210826
0.9182	High Similarity	NPC38591
0.9161	High Similarity	NPC122365
0.9161	High Similarity	NPC235333
0.9161	High Similarity	NPC472462
0.9156	High Similarity	NPC156244
0.915	High Similarity	NPC296030
0.915	High Similarity	NPC178202
0.915	High Similarity	NPC39929
0.915	High Similarity	NPC221868
0.915	High Similarity	NPC37208
0.9146	High Similarity	NPC164384
0.9141	High Similarity	NPC37606
0.9139	High Similarity	NPC230943
0.913	High Similarity	NPC86477
0.9108	High Similarity	NPC164110
0.9108	High Similarity	NPC270044
0.9108	High Similarity	NPC268360
0.9108	High Similarity	NPC246647
0.9108	High Similarity	NPC96342
0.9108	High Similarity	NPC269495
0.9108	High Similarity	NPC212967
0.9103	High Similarity	NPC297531
0.9103	High Similarity	NPC198490
0.9103	High Similarity	NPC213936
0.9097	High Similarity	NPC207624
0.9085	High Similarity	NPC272194
0.9085	High Similarity	NPC39195
0.9073	High Similarity	NPC225884
0.9073	High Similarity	NPC302181
0.9045	High Similarity	NPC180924
0.9038	High Similarity	NPC183874
0.9032	High Similarity	NPC23668
0.9032	High Similarity	NPC106372
0.9032	High Similarity	NPC115324
0.9032	High Similarity	NPC58668
0.9032	High Similarity	NPC193976
0.9032	High Similarity	NPC290671
0.9026	High Similarity	NPC317492
0.902	High Similarity	NPC308200
0.902	High Similarity	NPC17816
0.9007	High Similarity	NPC53192
0.8982	High Similarity	NPC97523
0.8981	High Similarity	NPC99199
0.8974	High Similarity	NPC263676
0.8974	High Similarity	NPC142308
0.8968	High Similarity	NPC155882
0.8968	High Similarity	NPC191104
0.8968	High Similarity	NPC470107
0.8968	High Similarity	NPC167576
0.8961	High Similarity	NPC145467
0.8961	High Similarity	NPC168085
0.8957	High Similarity	NPC53252
0.8954	High Similarity	NPC477955
0.8954	High Similarity	NPC470322
0.8954	High Similarity	NPC25844
0.8954	High Similarity	NPC299011
0.8954	High Similarity	NPC154217
0.8951	High Similarity	NPC277480
0.8947	High Similarity	NPC18585
0.8947	High Similarity	NPC166138
0.8947	High Similarity	NPC106985
0.8944	High Similarity	NPC472581
0.8944	High Similarity	NPC109180
0.8938	High Similarity	NPC30655
0.8938	High Similarity	NPC74854
0.8938	High Similarity	NPC92589
0.8938	High Similarity	NPC45124
0.8917	High Similarity	NPC72370
0.891	High Similarity	NPC316960
0.891	High Similarity	NPC116604
0.891	High Similarity	NPC78835
0.891	High Similarity	NPC148945
0.891	High Similarity	NPC204561
0.891	High Similarity	NPC209142
0.891	High Similarity	NPC317715
0.891	High Similarity	NPC312549
0.891	High Similarity	NPC309512
0.8903	High Similarity	NPC88445
0.8903	High Similarity	NPC266499
0.8903	High Similarity	NPC471114
0.8896	High Similarity	NPC50394
0.8896	High Similarity	NPC140120
0.8896	High Similarity	NPC476459
0.8889	High Similarity	NPC196137
0.8889	High Similarity	NPC311741
0.8889	High Similarity	NPC234629
0.8889	High Similarity	NPC184649
0.8889	High Similarity	NPC155144
0.8889	High Similarity	NPC469953
0.8889	High Similarity	NPC303185
0.8889	High Similarity	NPC136641
0.8889	High Similarity	NPC271288
0.8889	High Similarity	NPC98926
0.8889	High Similarity	NPC37183
0.8889	High Similarity	NPC29411
0.8889	High Similarity	NPC311144
0.8889	High Similarity	NPC1886
0.8882	High Similarity	NPC313036
0.8882	High Similarity	NPC36181
0.8882	High Similarity	NPC144499
0.8882	High Similarity	NPC96791
0.8882	High Similarity	NPC226942
0.8882	High Similarity	NPC470636
0.8882	High Similarity	NPC219861
0.8875	High Similarity	NPC49009
0.8875	High Similarity	NPC169
0.8874	High Similarity	NPC69769
0.8861	High Similarity	NPC469934
0.8861	High Similarity	NPC108937
0.8861	High Similarity	NPC279218
0.8861	High Similarity	NPC474542
0.8854	High Similarity	NPC473996
0.8846	High Similarity	NPC295036
0.8846	High Similarity	NPC471115
0.8846	High Similarity	NPC29777
0.8846	High Similarity	NPC474735
0.8846	High Similarity	NPC321896
0.8846	High Similarity	NPC476185
0.8839	High Similarity	NPC186397
0.8839	High Similarity	NPC37135
0.8831	High Similarity	NPC181388
0.8831	High Similarity	NPC472629
0.8827	High Similarity	NPC159508
0.8824	High Similarity	NPC221432
0.8824	High Similarity	NPC188632
0.8824	High Similarity	NPC196459
0.8824	High Similarity	NPC257097
0.8824	High Similarity	NPC175504
0.8824	High Similarity	NPC75049
0.8824	High Similarity	NPC470296
0.8824	High Similarity	NPC17262
0.8824	High Similarity	NPC169591
0.8824	High Similarity	NPC310130
0.8824	High Similarity	NPC143896
0.8824	High Similarity	NPC68104
0.8824	High Similarity	NPC113770
0.8824	High Similarity	NPC149026
0.8824	High Similarity	NPC94794
0.8824	High Similarity	NPC87609
0.8824	High Similarity	NPC150408
0.8824	High Similarity	NPC112791
0.8824	High Similarity	NPC91560
0.8824	High Similarity	NPC39329
0.8824	High Similarity	NPC164980
0.882	High Similarity	NPC14822
0.8816	High Similarity	NPC110969
0.8816	High Similarity	NPC3188
0.8812	High Similarity	NPC472877
0.8805	High Similarity	NPC78554
0.8805	High Similarity	NPC469936
0.8805	High Similarity	NPC146211
0.8805	High Similarity	NPC321372
0.8805	High Similarity	NPC474609
0.8805	High Similarity	NPC137100
0.8805	High Similarity	NPC109967
0.8805	High Similarity	NPC474738
0.8805	High Similarity	NPC475797
0.8805	High Similarity	NPC129053
0.879	High Similarity	NPC472580
0.879	High Similarity	NPC318424
0.879	High Similarity	NPC472636

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 NPC115432 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	967
0.2-0.3	1591
0.3-0.4	2590
0.4-0.5	2046
0.5-0.6	1094
0.6-0.7	341
0.7-0.8	108
0.8-0.85	48
0.85-0.9	21
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9108	High Similarity	NPD3749	Approved
0.879	High Similarity	NPD7411	Suspended
0.8774	High Similarity	NPD920	Approved
0.8766	High Similarity	NPD4378	Clinical (unspecified phase)
0.8684	High Similarity	NPD1243	Approved
0.8679	High Similarity	NPD7819	Suspended
0.8675	High Similarity	NPD2344	Approved
0.8659	High Similarity	NPD7852	Clinical (unspecified phase)
0.8645	High Similarity	NPD642	Clinical (unspecified phase)
0.8634	High Similarity	NPD7075	Discontinued
0.8571	High Similarity	NPD7768	Phase 2
0.8562	High Similarity	NPD7096	Clinical (unspecified phase)
0.8526	High Similarity	NPD7410	Clinical (unspecified phase)
0.8516	High Similarity	NPD643	Clinical (unspecified phase)
0.8509	High Similarity	NPD8443	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1549	Phase 2
0.8462	Intermediate Similarity	NPD6559	Discontinued
0.8452	Intermediate Similarity	NPD2309	Approved
0.8447	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD2800	Approved
0.8431	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD6232	Discontinued
0.8383	Intermediate Similarity	NPD7473	Discontinued
0.8375	Intermediate Similarity	NPD4380	Phase 2
0.8323	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1510	Phase 2
0.8291	Intermediate Similarity	NPD2534	Approved
0.8291	Intermediate Similarity	NPD2533	Approved
0.8291	Intermediate Similarity	NPD2532	Approved
0.8278	Intermediate Similarity	NPD1240	Approved
0.8272	Intermediate Similarity	NPD6801	Discontinued
0.8269	Intermediate Similarity	NPD3750	Approved
0.8253	Intermediate Similarity	NPD6959	Discontinued
0.8247	Intermediate Similarity	NPD2796	Approved
0.8228	Intermediate Similarity	NPD6799	Approved
0.8199	Intermediate Similarity	NPD3226	Approved
0.8194	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2799	Discontinued
0.8176	Intermediate Similarity	NPD5844	Phase 1
0.817	Intermediate Similarity	NPD1607	Approved
0.816	Intermediate Similarity	NPD1934	Approved
0.8155	Intermediate Similarity	NPD3926	Phase 2
0.8148	Intermediate Similarity	NPD6599	Discontinued
0.8133	Intermediate Similarity	NPD919	Approved
0.8129	Intermediate Similarity	NPD2935	Discontinued
0.8121	Intermediate Similarity	NPD3882	Suspended
0.8121	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD2801	Approved
0.8081	Intermediate Similarity	NPD5953	Discontinued
0.8026	Intermediate Similarity	NPD2313	Discontinued
0.8025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD4287	Approved
0.8013	Intermediate Similarity	NPD1551	Phase 2
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1511	Approved
0.7965	Intermediate Similarity	NPD7286	Phase 2
0.7965	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2346	Discontinued
0.7952	Intermediate Similarity	NPD3817	Phase 2
0.7949	Intermediate Similarity	NPD3748	Approved
0.7925	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD1512	Approved
0.7895	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6166	Phase 2
0.7892	Intermediate Similarity	NPD1465	Phase 2
0.7844	Intermediate Similarity	NPD2296	Approved
0.7824	Intermediate Similarity	NPD1247	Approved
0.7815	Intermediate Similarity	NPD1203	Approved
0.7784	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5710	Approved
0.7778	Intermediate Similarity	NPD6808	Phase 2
0.7778	Intermediate Similarity	NPD5711	Approved
0.7778	Intermediate Similarity	NPD7229	Phase 3
0.7744	Intermediate Similarity	NPD5403	Approved
0.7738	Intermediate Similarity	NPD5402	Approved
0.7722	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7074	Phase 3
0.7707	Intermediate Similarity	NPD6651	Approved
0.7702	Intermediate Similarity	NPD4628	Phase 3
0.7702	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD3764	Approved
0.7677	Intermediate Similarity	NPD3268	Approved
0.767	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6832	Phase 2
0.7657	Intermediate Similarity	NPD7054	Approved
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1471	Phase 3
0.7622	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5401	Approved
0.7619	Intermediate Similarity	NPD6280	Approved
0.7619	Intermediate Similarity	NPD6279	Approved
0.7616	Intermediate Similarity	NPD9717	Approved
0.7614	Intermediate Similarity	NPD7472	Approved
0.7611	Intermediate Similarity	NPD8434	Phase 2
0.7582	Intermediate Similarity	NPD2797	Approved
0.7571	Intermediate Similarity	NPD6797	Phase 2
0.7561	Intermediate Similarity	NPD7390	Discontinued
0.756	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4908	Phase 1
0.7545	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7486	Intermediate Similarity	NPD7808	Phase 3
0.7485	Intermediate Similarity	NPD7003	Approved
0.7453	Intermediate Similarity	NPD6100	Approved
0.7453	Intermediate Similarity	NPD5408	Approved
0.7453	Intermediate Similarity	NPD5406	Approved
0.7453	Intermediate Similarity	NPD6099	Approved
0.7453	Intermediate Similarity	NPD5404	Approved
0.7453	Intermediate Similarity	NPD5405	Approved
0.7444	Intermediate Similarity	NPD8313	Approved
0.7444	Intermediate Similarity	NPD8312	Approved
0.7434	Intermediate Similarity	NPD422	Phase 1
0.7432	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD447	Suspended
0.7421	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5124	Phase 1
0.7421	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2798	Approved
0.738	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD4363	Phase 3
0.7366	Intermediate Similarity	NPD4360	Phase 2
0.7358	Intermediate Similarity	NPD943	Approved
0.7355	Intermediate Similarity	NPD3266	Approved
0.7355	Intermediate Similarity	NPD1164	Approved
0.7355	Intermediate Similarity	NPD3267	Approved
0.7349	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7458	Discontinued
0.7326	Intermediate Similarity	NPD4361	Phase 2
0.7326	Intermediate Similarity	NPD4288	Approved
0.7326	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1610	Phase 2
0.732	Intermediate Similarity	NPD8151	Discontinued
0.732	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD1729	Discontinued
0.7314	Intermediate Similarity	NPD7199	Phase 2
0.7312	Intermediate Similarity	NPD230	Phase 1
0.7312	Intermediate Similarity	NPD1933	Approved
0.7303	Intermediate Similarity	NPD3751	Discontinued
0.7299	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3225	Approved
0.7278	Intermediate Similarity	NPD4625	Phase 3
0.7273	Intermediate Similarity	NPD1608	Approved
0.7267	Intermediate Similarity	NPD5760	Phase 2
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7267	Intermediate Similarity	NPD5761	Phase 2
0.725	Intermediate Similarity	NPD4307	Phase 2
0.7233	Intermediate Similarity	NPD411	Approved
0.7232	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2654	Approved
0.7209	Intermediate Similarity	NPD37	Approved
0.7207	Intermediate Similarity	NPD7177	Discontinued
0.72	Intermediate Similarity	NPD6234	Discontinued
0.7197	Intermediate Similarity	NPD1019	Discontinued
0.7195	Intermediate Similarity	NPD6004	Phase 3
0.7195	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6002	Phase 3
0.7195	Intermediate Similarity	NPD6005	Phase 3
0.7195	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4966	Approved
0.7184	Intermediate Similarity	NPD4967	Phase 2
0.7184	Intermediate Similarity	NPD4965	Approved
0.7174	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD9545	Approved
0.7161	Intermediate Similarity	NPD3972	Approved
0.716	Intermediate Similarity	NPD6273	Approved
0.7157	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7783	Phase 2
0.7152	Intermediate Similarity	NPD9493	Approved
0.7151	Intermediate Similarity	NPD5889	Approved
0.7151	Intermediate Similarity	NPD5890	Approved
0.715	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD6971	Discontinued
0.7134	Intermediate Similarity	NPD1470	Approved
0.7125	Intermediate Similarity	NPD1296	Phase 2
0.7125	Intermediate Similarity	NPD6798	Discontinued
0.7099	Intermediate Similarity	NPD6355	Discontinued
0.7095	Intermediate Similarity	NPD2403	Approved
0.7093	Intermediate Similarity	NPD6585	Discontinued
0.7083	Intermediate Similarity	NPD6780	Approved
0.7083	Intermediate Similarity	NPD6776	Approved
0.7083	Intermediate Similarity	NPD6781	Approved
0.7083	Intermediate Similarity	NPD6777	Approved
0.7083	Intermediate Similarity	NPD6778	Approved
0.7083	Intermediate Similarity	NPD6779	Approved
0.7083	Intermediate Similarity	NPD6782	Approved
0.7079	Intermediate Similarity	NPD3787	Discontinued
0.7078	Intermediate Similarity	NPD17	Approved
0.7074	Intermediate Similarity	NPD3269	Clinical (unspecified phase)

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