NPASS Compound

Structure

CID211413 OpenBabel06191716002D 31 34 0 0 1 0 0 0 0 0999 V2000 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -1.7321 0.0000 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 4.3301 0.5000 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 7.7942 -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 1 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 -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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 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 -0.0000 -1.0000 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 -1.7321 -3.0000 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 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 29 1 0 0 0 0 6 7 1 0 0 0 0 6 15 2 0 0 0 0 7 18 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 21 1 0 0 0 0 10 11 2 0 0 0 0 10 19 1 0 0 0 0 11 26 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 22 2 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 30 1 0 0 0 0 16 17 1 6 0 0 0 17 25 2 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 21 2 0 0 0 0 19 25 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 29 1 0 0 0 0 25 31 1 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.21
Volume:	446.886
LogP:	7.293
LogD:	4.973
LogS:	-2.507
# Rotatable Bonds:	4
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.635
Synthetic Accessibility Score:	3.847
Fsp3:	0.385
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:	-4.951
MDCK Permeability:	2.1324407498468645e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.155
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	100.6487045288086%
Volume Distribution (VD):	2.617
Pgp-substrate:	2.1076173782348633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.414
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.883
CYP2C19-substrate:	0.49
CYP2C9-inhibitor:	0.789
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.902
CYP2D6-substrate:	0.751
CYP3A4-inhibitor:	0.579
CYP3A4-substrate:	0.497

ADMET: Excretion

Clearance (CL):	7.811
Half-life (T1/2):	0.088

ADMET: Toxicity

hERG Blockers:	0.426
Human Hepatotoxicity (H-HT):	0.923
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.861
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.929
Carcinogencity:	0.303
Eye Corrosion:	0.003
Eye Irritation:	0.438
Respiratory Toxicity:	0.847

Download Data

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

Natural Product: NPC211413

Natural Product ID:	NPC211413
*Common Name:**	(3R)-7,4'-Dihydroxy-5-Methoxy-6-Prenyl-6''',6'''-Dimethylpyrano[2''',3''':2',3']-Isoflavan
IUPAC Name:	8-[(3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]-2,2-dimethylchromen-5-ol
Synonyms:
Standard InCHIKey:	NPCBOHBGCANYKG-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C26H30O5/c1-15(2)6-7-18-22(28)13-23-20(24(18)29-5)12-16(14-30-23)17-8-9-21(27)19-10-11-26(3,4)31-25(17)19/h6,8-11,13,16,27-28H,7,12,14H2,1-5H3/t16-/m0/s1
SMILES:	CC(=CCc1c(cc2c(C[C@@H](CO2)c2ccc(c3C=CC(C)(C)Oc23)O)c1OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3125428
PubChem CID:	76332672
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.	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]
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]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	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	2

Activity Type	# Activity
NON-MOLECULAR	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBC	=	6.25	ug ml-1	PMID[522752]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	6.25	ug.mL-1	PMID[522752]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MBC	=	6.25	ug ml-1	PMID[522752]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	6.25	ug.mL-1	PMID[522752]

☑ 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 NPC211413 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	393
0.1-0.2	1564
0.2-0.3	3929
0.3-0.4	12013
0.4-0.5	6578
0.5-0.6	4146
0.6-0.7	7688
0.7-0.8	5204
0.8-0.85	846
0.85-0.9	212
0.9-0.95	68
0.95-1	56

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC244888
1.0	High Similarity	NPC118683
1.0	High Similarity	NPC293203
1.0	High Similarity	NPC164804
1.0	High Similarity	NPC68205
0.9841	High Similarity	NPC77196
0.9764	High Similarity	NPC223008
0.9764	High Similarity	NPC296915
0.9764	High Similarity	NPC225696
0.9764	High Similarity	NPC198154
0.9764	High Similarity	NPC115335
0.9764	High Similarity	NPC97834
0.9758	High Similarity	NPC38664
0.9758	High Similarity	NPC53986
0.9685	High Similarity	NPC92805
0.968	High Similarity	NPC134360
0.968	High Similarity	NPC93962
0.9606	High Similarity	NPC13005
0.9597	High Similarity	NPC26879
0.9597	High Similarity	NPC230479
0.9597	High Similarity	NPC283049
0.9597	High Similarity	NPC50315
0.9528	High Similarity	NPC129106
0.9528	High Similarity	NPC164574
0.9528	High Similarity	NPC118114
0.9528	High Similarity	NPC268917
0.9528	High Similarity	NPC228369
0.9528	High Similarity	NPC129784
0.9528	High Similarity	NPC196765
0.9528	High Similarity	NPC476166
0.9528	High Similarity	NPC207892
0.9528	High Similarity	NPC300875
0.9528	High Similarity	NPC12875
0.9528	High Similarity	NPC206224
0.9528	High Similarity	NPC150011
0.9528	High Similarity	NPC280653
0.9528	High Similarity	NPC236014
0.9528	High Similarity	NPC17343
0.952	High Similarity	NPC149796
0.9462	High Similarity	NPC20829
0.9462	High Similarity	NPC262585
0.9462	High Similarity	NPC18189
0.9449	High Similarity	NPC470225
0.9449	High Similarity	NPC27187
0.9444	High Similarity	NPC274717
0.938	High Similarity	NPC85435
0.9375	High Similarity	NPC271945
0.9375	High Similarity	NPC181497
0.936	High Similarity	NPC103420
0.936	High Similarity	NPC188022
0.936	High Similarity	NPC285040
0.936	High Similarity	NPC17809
0.936	High Similarity	NPC102540
0.9323	High Similarity	NPC5155
0.9318	High Similarity	NPC475836
0.9308	High Similarity	NPC117048
0.9308	High Similarity	NPC473107
0.9308	High Similarity	NPC124085
0.9291	High Similarity	NPC47283
0.9291	High Similarity	NPC39064
0.9286	High Similarity	NPC276212
0.928	High Similarity	NPC246648
0.928	High Similarity	NPC86502
0.928	High Similarity	NPC106914
0.928	High Similarity	NPC197351
0.928	High Similarity	NPC134195
0.9254	High Similarity	NPC204347
0.9254	High Similarity	NPC2613
0.9254	High Similarity	NPC59841
0.9254	High Similarity	NPC475891
0.9242	High Similarity	NPC474687
0.9225	High Similarity	NPC103799
0.9225	High Similarity	NPC162801
0.92	High Similarity	NPC76465
0.92	High Similarity	NPC38761
0.9194	High Similarity	NPC193364
0.9194	High Similarity	NPC54972
0.9167	High Similarity	NPC3049
0.9167	High Similarity	NPC471522
0.9141	High Similarity	NPC222572
0.9141	High Similarity	NPC87224
0.9134	High Similarity	NPC262573
0.9134	High Similarity	NPC471215
0.9127	High Similarity	NPC159132
0.912	High Similarity	NPC36016
0.912	High Similarity	NPC100099
0.9098	High Similarity	NPC470308
0.9098	High Similarity	NPC470307
0.9062	High Similarity	NPC473134
0.9051	High Similarity	NPC469557
0.903	High Similarity	NPC260741
0.903	High Similarity	NPC70682
0.9015	High Similarity	NPC476617
0.9015	High Similarity	NPC476616
0.9015	High Similarity	NPC131950
0.9015	High Similarity	NPC476615
0.8978	High Similarity	NPC475492
0.8976	High Similarity	NPC294156
0.8976	High Similarity	NPC256015
0.8952	High Similarity	NPC295259
0.8947	High Similarity	NPC125579
0.8947	High Similarity	NPC473413
0.8931	High Similarity	NPC472590
0.8931	High Similarity	NPC160623
0.8923	High Similarity	NPC222108
0.8923	High Similarity	NPC96719
0.8921	High Similarity	NPC16269
0.8921	High Similarity	NPC21776
0.8915	High Similarity	NPC46978
0.8906	High Similarity	NPC81641
0.8898	High Similarity	NPC474160
0.8897	High Similarity	NPC100482
0.8897	High Similarity	NPC35216
0.8897	High Similarity	NPC277331
0.8889	High Similarity	NPC476633
0.8889	High Similarity	NPC32630
0.8881	High Similarity	NPC248727
0.8881	High Similarity	NPC270456
0.8881	High Similarity	NPC173660
0.8881	High Similarity	NPC162659
0.8881	High Similarity	NPC265433
0.888	High Similarity	NPC8283
0.888	High Similarity	NPC93398
0.888	High Similarity	NPC258979
0.8871	High Similarity	NPC74821
0.8871	High Similarity	NPC131118
0.8864	High Similarity	NPC472798
0.8849	High Similarity	NPC233980
0.8841	High Similarity	NPC473108
0.8828	High Similarity	NPC270030
0.8824	High Similarity	NPC259519
0.8819	High Similarity	NPC150026
0.8806	High Similarity	NPC151224
0.8806	High Similarity	NPC195022
0.88	High Similarity	NPC172253
0.88	High Similarity	NPC59561
0.8797	High Similarity	NPC469610
0.8797	High Similarity	NPC215037
0.8797	High Similarity	NPC11060
0.8779	High Similarity	NPC16577
0.8779	High Similarity	NPC472796
0.8779	High Similarity	NPC472795
0.8779	High Similarity	NPC472797
0.8777	High Similarity	NPC101255
0.8777	High Similarity	NPC475719
0.8777	High Similarity	NPC43716
0.876	High Similarity	NPC167571
0.876	High Similarity	NPC207179
0.876	High Similarity	NPC278552
0.8759	High Similarity	NPC265075
0.875	High Similarity	NPC127218
0.875	High Similarity	NPC47040
0.875	High Similarity	NPC319647
0.875	High Similarity	NPC144512
0.875	High Similarity	NPC471388
0.875	High Similarity	NPC25966
0.875	High Similarity	NPC278600
0.875	High Similarity	NPC245207
0.875	High Similarity	NPC137262
0.875	High Similarity	NPC37428
0.875	High Similarity	NPC35501
0.8741	High Similarity	NPC234952
0.8741	High Similarity	NPC470802
0.8741	High Similarity	NPC474639
0.8741	High Similarity	NPC227503
0.8741	High Similarity	NPC472800
0.8741	High Similarity	NPC230734
0.8741	High Similarity	NPC141717
0.874	High Similarity	NPC190454
0.874	High Similarity	NPC97432
0.8731	High Similarity	NPC317380
0.8722	High Similarity	NPC469611
0.8712	High Similarity	NPC32463
0.8712	High Similarity	NPC254000
0.871	High Similarity	NPC85292
0.871	High Similarity	NPC229147
0.871	High Similarity	NPC54507
0.8705	High Similarity	NPC93323
0.8705	High Similarity	NPC45257
0.8705	High Similarity	NPC12641
0.8705	High Similarity	NPC280092
0.8702	High Similarity	NPC211179
0.8702	High Similarity	NPC38604
0.8686	High Similarity	NPC27495
0.8686	High Similarity	NPC309124
0.8686	High Similarity	NPC184797
0.8676	High Similarity	NPC211549
0.8676	High Similarity	NPC276490
0.8676	High Similarity	NPC477938
0.8672	High Similarity	NPC74137
0.8671	High Similarity	NPC471115
0.8671	High Similarity	NPC29777
0.8667	High Similarity	NPC470356
0.8667	High Similarity	NPC164787
0.8667	High Similarity	NPC15109
0.8667	High Similarity	NPC94750
0.8667	High Similarity	NPC112246
0.8667	High Similarity	NPC61946
0.8667	High Similarity	NPC121812
0.8667	High Similarity	NPC474206

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 NPC211413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	931
0.2-0.3	1565
0.3-0.4	2707
0.4-0.5	1780
0.5-0.6	1030
0.6-0.7	651
0.7-0.8	149
0.8-0.85	7
0.85-0.9	3
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9603	High Similarity	NPD4907	Clinical (unspecified phase)
0.9444	High Similarity	NPD4908	Phase 1
0.9194	High Similarity	NPD1610	Phase 2
0.8871	High Similarity	NPD1548	Phase 1
0.8779	High Similarity	NPD4625	Phase 3
0.8605	High Similarity	NPD4749	Approved
0.8571	High Similarity	NPD6410	Clinical (unspecified phase)
0.8519	High Similarity	NPD5123	Clinical (unspecified phase)
0.8519	High Similarity	NPD5124	Phase 1
0.8485	Intermediate Similarity	NPD2861	Phase 2
0.8444	Intermediate Similarity	NPD1613	Approved
0.8444	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD7447	Phase 1
0.8125	Intermediate Similarity	NPD7213	Phase 3
0.8125	Intermediate Similarity	NPD7212	Phase 2
0.8088	Intermediate Similarity	NPD3027	Phase 3
0.8067	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD422	Phase 1
0.8029	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4380	Phase 2
0.7917	Intermediate Similarity	NPD7466	Approved
0.7917	Intermediate Similarity	NPD3750	Approved
0.7914	Intermediate Similarity	NPD4060	Phase 1
0.791	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6671	Approved
0.7887	Intermediate Similarity	NPD6099	Approved
0.7887	Intermediate Similarity	NPD6100	Approved
0.7881	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD8651	Approved
0.7832	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7768	Phase 2
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.7748	Intermediate Similarity	NPD7411	Suspended
0.7746	Intermediate Similarity	NPD4538	Approved
0.7746	Intermediate Similarity	NPD4536	Approved
0.7746	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1510	Phase 2
0.7664	Intermediate Similarity	NPD2797	Approved
0.7647	Intermediate Similarity	NPD7819	Suspended
0.7639	Intermediate Similarity	NPD2796	Approved
0.763	Intermediate Similarity	NPD1091	Approved
0.7619	Intermediate Similarity	NPD968	Approved
0.7613	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD7075	Discontinued
0.7603	Intermediate Similarity	NPD1652	Phase 2
0.7591	Intermediate Similarity	NPD6696	Suspended
0.7582	Intermediate Similarity	NPD1934	Approved
0.7581	Intermediate Similarity	NPD846	Approved
0.7581	Intermediate Similarity	NPD940	Approved
0.758	Intermediate Similarity	NPD6959	Discontinued
0.7569	Intermediate Similarity	NPD3748	Approved
0.7569	Intermediate Similarity	NPD5960	Phase 3
0.7569	Intermediate Similarity	NPD7033	Discontinued
0.7569	Intermediate Similarity	NPD5588	Approved
0.7568	Intermediate Similarity	NPD5058	Phase 3
0.7551	Intermediate Similarity	NPD3892	Phase 2
0.7547	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD3268	Approved
0.7518	Intermediate Similarity	NPD6582	Phase 2
0.7518	Intermediate Similarity	NPD6583	Phase 3
0.7516	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7097	Phase 1
0.75	Intermediate Similarity	NPD7157	Approved
0.75	Intermediate Similarity	NPD2684	Approved
0.7483	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6674	Discontinued
0.7482	Intermediate Similarity	NPD6584	Phase 3
0.7467	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD3225	Approved
0.745	Intermediate Similarity	NPD6667	Approved
0.745	Intermediate Similarity	NPD6666	Approved
0.7444	Intermediate Similarity	NPD7340	Approved
0.7442	Intermediate Similarity	NPD4750	Phase 3
0.7436	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3018	Phase 2
0.7421	Intermediate Similarity	NPD7229	Phase 3
0.7419	Intermediate Similarity	NPD3020	Approved
0.7419	Intermediate Similarity	NPD2801	Approved
0.7415	Intermediate Similarity	NPD2424	Discontinued
0.7413	Intermediate Similarity	NPD1240	Approved
0.7413	Intermediate Similarity	NPD2238	Phase 2
0.7407	Intermediate Similarity	NPD5844	Phase 1
0.7405	Intermediate Similarity	NPD5535	Approved
0.7405	Intermediate Similarity	NPD7843	Approved
0.7405	Intermediate Similarity	NPD5494	Approved
0.7403	Intermediate Similarity	NPD6072	Discontinued
0.74	Intermediate Similarity	NPD7041	Phase 2
0.74	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1511	Approved
0.7379	Intermediate Similarity	NPD2200	Suspended
0.7361	Intermediate Similarity	NPD6355	Discontinued
0.7357	Intermediate Similarity	NPD3691	Phase 2
0.7357	Intermediate Similarity	NPD3690	Phase 2
0.7355	Intermediate Similarity	NPD6801	Discontinued
0.7348	Intermediate Similarity	NPD1398	Phase 1
0.7348	Intermediate Similarity	NPD5283	Phase 1
0.7347	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6002	Phase 3
0.7347	Intermediate Similarity	NPD6005	Phase 3
0.7347	Intermediate Similarity	NPD6004	Phase 3
0.7347	Intermediate Similarity	NPD7030	Discontinued
0.7347	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7549	Discontinued
0.7329	Intermediate Similarity	NPD6166	Phase 2
0.7329	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1653	Approved
0.731	Intermediate Similarity	NPD4097	Suspended
0.731	Intermediate Similarity	NPD1607	Approved
0.7308	Intermediate Similarity	NPD8455	Phase 2
0.7303	Intermediate Similarity	NPD1512	Approved
0.7297	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD290	Approved
0.7279	Intermediate Similarity	NPD2935	Discontinued
0.7279	Intermediate Similarity	NPD1551	Phase 2
0.7278	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7266	Intermediate Similarity	NPD2983	Phase 2
0.7266	Intermediate Similarity	NPD5327	Phase 3
0.7266	Intermediate Similarity	NPD2982	Phase 2
0.7248	Intermediate Similarity	NPD2800	Approved
0.7244	Intermediate Similarity	NPD37	Approved
0.7241	Intermediate Similarity	NPD5735	Approved
0.7233	Intermediate Similarity	NPD6234	Discontinued
0.7229	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5846	Approved
0.7226	Intermediate Similarity	NPD4626	Approved
0.7226	Intermediate Similarity	NPD2668	Approved
0.7226	Intermediate Similarity	NPD6516	Phase 2
0.7226	Intermediate Similarity	NPD2667	Approved
0.7222	Intermediate Similarity	NPD1242	Phase 1
0.7215	Intermediate Similarity	NPD4966	Approved
0.7215	Intermediate Similarity	NPD4965	Approved
0.7215	Intermediate Similarity	NPD4967	Phase 2
0.7211	Intermediate Similarity	NPD2799	Discontinued
0.7211	Intermediate Similarity	NPD4108	Discontinued
0.7206	Intermediate Similarity	NPD7741	Discontinued
0.7203	Intermediate Similarity	NPD7095	Approved
0.72	Intermediate Similarity	NPD4535	Phase 3
0.7197	Intermediate Similarity	NPD5929	Approved
0.7195	Intermediate Similarity	NPD7054	Approved
0.7194	Intermediate Similarity	NPD2230	Approved
0.7194	Intermediate Similarity	NPD2981	Phase 2
0.7194	Intermediate Similarity	NPD1608	Approved
0.7194	Intermediate Similarity	NPD2233	Approved
0.7194	Intermediate Similarity	NPD2232	Approved
0.7192	Intermediate Similarity	NPD6353	Approved
0.7181	Intermediate Similarity	NPD7037	Approved
0.7177	Intermediate Similarity	NPD2860	Approved
0.7177	Intermediate Similarity	NPD2859	Approved
0.7176	Intermediate Similarity	NPD5451	Approved
0.7174	Intermediate Similarity	NPD3496	Discontinued
0.7172	Intermediate Similarity	NPD4140	Approved
0.7171	Intermediate Similarity	NPD6799	Approved
0.7169	Intermediate Similarity	NPD6559	Discontinued
0.7163	Intermediate Similarity	NPD3266	Approved
0.7163	Intermediate Similarity	NPD3267	Approved
0.7162	Intermediate Similarity	NPD4477	Approved
0.7162	Intermediate Similarity	NPD4476	Approved
0.7161	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5691	Approved
0.7153	Intermediate Similarity	NPD3445	Approved
0.7153	Intermediate Similarity	NPD3443	Approved
0.7153	Intermediate Similarity	NPD3444	Approved
0.7152	Intermediate Similarity	NPD7074	Phase 3
0.7152	Intermediate Similarity	NPD3817	Phase 2
0.7152	Intermediate Similarity	NPD7472	Approved
0.7143	Intermediate Similarity	NPD821	Approved
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD5403	Approved
0.7134	Intermediate Similarity	NPD7228	Approved
0.7133	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2532	Approved
0.7124	Intermediate Similarity	NPD2534	Approved
0.7124	Intermediate Similarity	NPD2533	Approved
0.7123	Intermediate Similarity	NPD4340	Discontinued
0.7122	Intermediate Similarity	NPD1611	Approved
0.7115	Intermediate Similarity	NPD6599	Discontinued
0.7114	Intermediate Similarity	NPD5762	Approved
0.7114	Intermediate Similarity	NPD5763	Approved
0.7113	Intermediate Similarity	NPD4624	Approved
0.7111	Intermediate Similarity	NPD2557	Approved
0.7111	Intermediate Similarity	NPD6387	Discontinued
0.711	Intermediate Similarity	NPD4363	Phase 3
0.711	Intermediate Similarity	NPD4360	Phase 2
0.7108	Intermediate Similarity	NPD6797	Phase 2
0.7107	Intermediate Similarity	NPD3882	Suspended
0.7105	Intermediate Similarity	NPD6815	Approved
0.7103	Intermediate Similarity	NPD6233	Phase 2

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