NPASS Compound

Structure

CID126836 OpenBabel06191715482D 21 22 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -3.4641 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 12 1 0 0 0 0 6 15 2 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 17 2 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.14
Volume:	304.817
LogP:	3.663
LogD:	3.604
LogS:	-3.404
# Rotatable Bonds:	5
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.887
Synthetic Accessibility Score:	2.312
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.918
MDCK Permeability:	1.8059878129861318e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.073
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.849
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	98.17137908935547%
Volume Distribution (VD):	0.967
Pgp-substrate:	1.233614206314087%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.91
CYP2C19-substrate:	0.427
CYP2C9-inhibitor:	0.527
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.926
CYP2D6-substrate:	0.939
CYP3A4-inhibitor:	0.75
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	11.962
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.384
Skin Sensitization:	0.944
Carcinogencity:	0.081
Eye Corrosion:	0.025
Eye Irritation:	0.952
Respiratory Toxicity:	0.404

Download Data

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

Natural Product: NPC126836

Natural Product ID:	NPC126836
*Common Name:**	Stilbostemin F
IUPAC Name:	3-[2-(3-hydroxy-2-methoxyphenyl)ethyl]-5-methoxy-2-methylphenol
Synonyms:
Standard InCHIKey:	XCEKLBSFNZXDES-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H20O4/c1-11-13(9-14(20-2)10-16(11)19)8-7-12-5-4-6-15(18)17(12)21-3/h4-6,9-10,18-19H,7-8H2,1-3H3
SMILES:	COc1cc(CCc2cccc(c2OC)O)c(c(c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464292
PubChem CID:	636713
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	Leaves, rhizomes, and roots	southeast Thailand near Chonburi	2000-Feb, 2001-Jan	PMID[12088422]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	slowly dried tubers	Bangkok, Thailand	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	n.a.	Southeast Thailand near Chonburi, Khao Khieo, close to the Chanthathen waterfall and Sri Racha	n.a.	PMID[15679323]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[16643052]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	Roots; Stems; Tubers	n.a.	n.a.	PMID[16872143]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[18452334]
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	Roots; Stems	n.a.	n.a.	PMID[19374387]
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20415428]
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	n.a.	root	n.a.	PMID[21126060]
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	Roots	Lampang Province, Thailand	2009-APR	PMID[21126060]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21902195]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21902195]
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21902195]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	leaf and root	n.a.	n.a.	Database[Title]
NPO10593	Aspergillus pulvinus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13984	Helenium radiatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9624	Myoporum bontioides	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO866	Heliomeris longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28187	Duguetia confinis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19620	Stemona tuberosa	Species	Stemonaceae	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
IC50	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[451046]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[451046]

☑ 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 NPC126836 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	433
0.1-0.2	1778
0.2-0.3	5210
0.3-0.4	13225
0.4-0.5	4285
0.5-0.6	3956
0.6-0.7	7164
0.7-0.8	5020
0.8-0.85	816
0.85-0.9	514
0.9-0.95	213
0.95-1	83

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC32778
0.9756	High Similarity	NPC82679
0.9756	High Similarity	NPC236791
0.9756	High Similarity	NPC282000
0.9756	High Similarity	NPC324112
0.9756	High Similarity	NPC124452
0.9756	High Similarity	NPC246620
0.9756	High Similarity	NPC293054
0.9756	High Similarity	NPC74817
0.9756	High Similarity	NPC159968
0.9756	High Similarity	NPC169474
0.9677	High Similarity	NPC154866
0.9675	High Similarity	NPC44748
0.9675	High Similarity	NPC28730
0.9675	High Similarity	NPC214406
0.9675	High Similarity	NPC78974
0.9675	High Similarity	NPC223136
0.9675	High Similarity	NPC18924
0.9675	High Similarity	NPC103823
0.9609	High Similarity	NPC313081
0.9609	High Similarity	NPC108198
0.9609	High Similarity	NPC158142
0.9609	High Similarity	NPC10314
0.9609	High Similarity	NPC69029
0.9609	High Similarity	NPC200557
0.9609	High Similarity	NPC294884
0.9603	High Similarity	NPC15543
0.9597	High Similarity	NPC266555
0.9597	High Similarity	NPC127587
0.9593	High Similarity	NPC299584
0.9593	High Similarity	NPC233410
0.9593	High Similarity	NPC475169
0.9593	High Similarity	NPC265483
0.9593	High Similarity	NPC17943
0.9593	High Similarity	NPC193544
0.9593	High Similarity	NPC105925
0.9593	High Similarity	NPC60885
0.9593	High Similarity	NPC82483
0.9593	High Similarity	NPC251855
0.9593	High Similarity	NPC57490
0.9593	High Similarity	NPC208950
0.9593	High Similarity	NPC298757
0.9593	High Similarity	NPC203133
0.9593	High Similarity	NPC116907
0.9593	High Similarity	NPC117214
0.9593	High Similarity	NPC234400
0.9593	High Similarity	NPC221077
0.9593	High Similarity	NPC472093
0.9535	High Similarity	NPC202846
0.9535	High Similarity	NPC143139
0.9531	High Similarity	NPC289258
0.9531	High Similarity	NPC188378
0.9531	High Similarity	NPC125649
0.9531	High Similarity	NPC469659
0.9531	High Similarity	NPC56764
0.9531	High Similarity	NPC7515
0.9531	High Similarity	NPC276026
0.9531	High Similarity	NPC555
0.9531	High Similarity	NPC206737
0.9531	High Similarity	NPC209199
0.9528	High Similarity	NPC6451
0.9524	High Similarity	NPC51840
0.9524	High Similarity	NPC311680
0.9524	High Similarity	NPC234488
0.9524	High Similarity	NPC299221
0.952	High Similarity	NPC28765
0.9516	High Similarity	NPC76451
0.9516	High Similarity	NPC223953
0.9462	High Similarity	NPC56329
0.9462	High Similarity	NPC242715
0.9457	High Similarity	NPC55239
0.9457	High Similarity	NPC180602
0.9457	High Similarity	NPC240279
0.9457	High Similarity	NPC214853
0.9457	High Similarity	NPC241241
0.9449	High Similarity	NPC474356
0.9449	High Similarity	NPC45715
0.9449	High Similarity	NPC12275
0.9449	High Similarity	NPC232275
0.9444	High Similarity	NPC58164
0.9444	High Similarity	NPC10225
0.9444	High Similarity	NPC212015
0.944	High Similarity	NPC236760
0.944	High Similarity	NPC252131
0.9431	High Similarity	NPC136319
0.9431	High Similarity	NPC228922
0.9431	High Similarity	NPC197757
0.9431	High Similarity	NPC233526
0.9431	High Similarity	NPC121115
0.9431	High Similarity	NPC95168
0.9431	High Similarity	NPC282496
0.9389	High Similarity	NPC212942
0.9389	High Similarity	NPC275061
0.9389	High Similarity	NPC220344
0.9389	High Similarity	NPC243996
0.9389	High Similarity	NPC132804
0.9389	High Similarity	NPC29868
0.9389	High Similarity	NPC79622
0.9389	High Similarity	NPC184613
0.9385	High Similarity	NPC133025
0.9385	High Similarity	NPC30632
0.938	High Similarity	NPC160697
0.9375	High Similarity	NPC161958
0.9375	High Similarity	NPC14224
0.937	High Similarity	NPC224157
0.937	High Similarity	NPC192687
0.9365	High Similarity	NPC206615
0.9365	High Similarity	NPC98631
0.9365	High Similarity	NPC266691
0.9365	High Similarity	NPC470213
0.9365	High Similarity	NPC186843
0.9355	High Similarity	NPC5796
0.9355	High Similarity	NPC206487
0.935	High Similarity	NPC262253
0.935	High Similarity	NPC71579
0.935	High Similarity	NPC473411
0.935	High Similarity	NPC41562
0.9318	High Similarity	NPC472090
0.9318	High Similarity	NPC472092
0.9318	High Similarity	NPC472091
0.9318	High Similarity	NPC12668
0.9318	High Similarity	NPC308768
0.9313	High Similarity	NPC156948
0.9313	High Similarity	NPC230919
0.9313	High Similarity	NPC22902
0.9313	High Similarity	NPC266453
0.9313	High Similarity	NPC301765
0.9313	High Similarity	NPC200935
0.9313	High Similarity	NPC3072
0.9313	High Similarity	NPC86605
0.9313	High Similarity	NPC46277
0.9308	High Similarity	NPC256262
0.9302	High Similarity	NPC475840
0.9297	High Similarity	NPC474017
0.9291	High Similarity	NPC190144
0.9291	High Similarity	NPC476968
0.9291	High Similarity	NPC170844
0.9286	High Similarity	NPC210355
0.9274	High Similarity	NPC84086
0.9268	High Similarity	NPC75713
0.9248	High Similarity	NPC472089
0.9242	High Similarity	NPC230124
0.9242	High Similarity	NPC105847
0.9242	High Similarity	NPC243759
0.9242	High Similarity	NPC6300
0.9242	High Similarity	NPC218131
0.9242	High Similarity	NPC114171
0.9242	High Similarity	NPC471183
0.9237	High Similarity	NPC162659
0.9237	High Similarity	NPC248727
0.9237	High Similarity	NPC270456
0.9237	High Similarity	NPC205442
0.9237	High Similarity	NPC234952
0.9237	High Similarity	NPC265433
0.9231	High Similarity	NPC317380
0.9225	High Similarity	NPC86655
0.9225	High Similarity	NPC202762
0.9225	High Similarity	NPC127624
0.9187	High Similarity	NPC166759
0.9187	High Similarity	NPC102639
0.9179	High Similarity	NPC472087
0.9179	High Similarity	NPC472088
0.9179	High Similarity	NPC175838
0.9179	High Similarity	NPC183709
0.9173	High Similarity	NPC109240
0.9167	High Similarity	NPC73535
0.9167	High Similarity	NPC272157
0.9167	High Similarity	NPC266006
0.9167	High Similarity	NPC201145
0.9167	High Similarity	NPC25111
0.9167	High Similarity	NPC6262
0.9167	High Similarity	NPC151656
0.9167	High Similarity	NPC90615
0.916	High Similarity	NPC121812
0.916	High Similarity	NPC112246
0.916	High Similarity	NPC94750
0.916	High Similarity	NPC112939
0.916	High Similarity	NPC474206
0.916	High Similarity	NPC470356
0.9154	High Similarity	NPC471391
0.9154	High Similarity	NPC229442
0.9154	High Similarity	NPC471390
0.9154	High Similarity	NPC168059
0.9154	High Similarity	NPC158331
0.9147	High Similarity	NPC469907
0.9141	High Similarity	NPC469963
0.9141	High Similarity	NPC469951
0.9134	High Similarity	NPC21563
0.9134	High Similarity	NPC242032
0.9134	High Similarity	NPC470699
0.9134	High Similarity	NPC106511
0.9127	High Similarity	NPC113495
0.9111	High Similarity	NPC469630
0.9106	High Similarity	NPC232084
0.9106	High Similarity	NPC10932
0.9106	High Similarity	NPC61516
0.9106	High Similarity	NPC474565
0.9106	High Similarity	NPC247364
0.9098	High Similarity	NPC245207
0.9098	High Similarity	NPC260741

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 NPC126836 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	981
0.2-0.3	1739
0.3-0.4	2781
0.4-0.5	1610
0.5-0.6	877
0.6-0.7	641
0.7-0.8	129
0.8-0.85	12
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9291	High Similarity	NPD3027	Phase 3
0.8915	High Similarity	NPD1529	Clinical (unspecified phase)
0.8837	High Similarity	NPD1530	Clinical (unspecified phase)
0.8788	High Similarity	NPD1612	Clinical (unspecified phase)
0.8788	High Similarity	NPD1613	Approved
0.855	High Similarity	NPD3018	Phase 2
0.8387	Intermediate Similarity	NPD5283	Phase 1
0.8385	Intermediate Similarity	NPD2983	Phase 2
0.8385	Intermediate Similarity	NPD2982	Phase 2
0.8374	Intermediate Similarity	NPD228	Approved
0.8346	Intermediate Similarity	NPD4908	Phase 1
0.8308	Intermediate Similarity	NPD2981	Phase 2
0.8284	Intermediate Similarity	NPD4625	Phase 3
0.8231	Intermediate Similarity	NPD1610	Phase 2
0.8222	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD3021	Approved
0.8065	Intermediate Similarity	NPD3022	Approved
0.8062	Intermediate Similarity	NPD1548	Phase 1
0.7987	Intermediate Similarity	NPD1934	Approved
0.7971	Intermediate Similarity	NPD3620	Phase 2
0.7971	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD4060	Phase 1
0.797	Intermediate Similarity	NPD4749	Approved
0.7961	Intermediate Similarity	NPD6234	Discontinued
0.7933	Intermediate Similarity	NPD2801	Approved
0.7926	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD3540	Phase 1
0.7867	Intermediate Similarity	NPD37	Approved
0.7829	Intermediate Similarity	NPD3882	Suspended
0.782	Intermediate Similarity	NPD3705	Approved
0.7817	Intermediate Similarity	NPD3539	Phase 1
0.7815	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6232	Discontinued
0.7785	Intermediate Similarity	NPD4005	Discontinued
0.7742	Intermediate Similarity	NPD7199	Phase 2
0.7737	Intermediate Similarity	NPD2861	Phase 2
0.7714	Intermediate Similarity	NPD1558	Phase 1
0.7712	Intermediate Similarity	NPD4966	Approved
0.7712	Intermediate Similarity	NPD4967	Phase 2
0.7712	Intermediate Similarity	NPD4965	Approved
0.7698	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1511	Approved
0.7671	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4055	Discovery
0.7658	Intermediate Similarity	NPD7473	Discontinued
0.7655	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD940	Approved
0.7642	Intermediate Similarity	NPD846	Approved
0.7639	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD4750	Phase 3
0.7619	Intermediate Similarity	NPD7124	Phase 2
0.761	Intermediate Similarity	NPD7228	Approved
0.76	Intermediate Similarity	NPD1653	Approved
0.7597	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6166	Phase 2
0.7595	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1512	Approved
0.7582	Intermediate Similarity	NPD1465	Phase 2
0.7576	Intermediate Similarity	NPD5536	Phase 2
0.7571	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5111	Phase 2
0.7571	Intermediate Similarity	NPD5110	Phase 2
0.7571	Intermediate Similarity	NPD5109	Approved
0.7568	Intermediate Similarity	NPD4357	Discontinued
0.7561	Intermediate Similarity	NPD1242	Phase 1
0.7556	Intermediate Similarity	NPD422	Phase 1
0.7537	Intermediate Similarity	NPD4626	Approved
0.7534	Intermediate Similarity	NPD6674	Discontinued
0.75	Intermediate Similarity	NPD8053	Approved
0.75	Intermediate Similarity	NPD8054	Approved
0.7483	Intermediate Similarity	NPD3892	Phase 2
0.7483	Intermediate Similarity	NPD3750	Approved
0.7466	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1240	Approved
0.7453	Intermediate Similarity	NPD5844	Phase 1
0.7451	Intermediate Similarity	NPD5089	Approved
0.7451	Intermediate Similarity	NPD5090	Approved
0.7448	Intermediate Similarity	NPD6100	Approved
0.7448	Intermediate Similarity	NPD6099	Approved
0.7436	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6111	Discontinued
0.7424	Intermediate Similarity	NPD6671	Approved
0.7424	Intermediate Similarity	NPD7157	Approved
0.7422	Intermediate Similarity	NPD2684	Approved
0.7419	Intermediate Similarity	NPD3817	Phase 2
0.7415	Intermediate Similarity	NPD3060	Approved
0.7407	Intermediate Similarity	NPD7074	Phase 3
0.7394	Intermediate Similarity	NPD2674	Phase 3
0.7391	Intermediate Similarity	NPD3818	Discontinued
0.7391	Intermediate Similarity	NPD8651	Approved
0.7386	Intermediate Similarity	NPD4675	Approved
0.7386	Intermediate Similarity	NPD4678	Approved
0.7379	Intermediate Similarity	NPD1510	Phase 2
0.7361	Intermediate Similarity	NPD1607	Approved
0.7361	Intermediate Similarity	NPD4097	Suspended
0.7351	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7054	Approved
0.7343	Intermediate Similarity	NPD943	Approved
0.7343	Intermediate Similarity	NPD2238	Phase 2
0.7339	Intermediate Similarity	NPD3020	Approved
0.7333	Intermediate Similarity	NPD1357	Approved
0.7333	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7843	Approved
0.7315	Intermediate Similarity	NPD2677	Approved
0.7315	Intermediate Similarity	NPD2219	Phase 1
0.7303	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7472	Approved
0.7299	Intermediate Similarity	NPD1091	Approved
0.7297	Intermediate Similarity	NPD5177	Phase 3
0.7293	Intermediate Similarity	NPD709	Approved
0.7285	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7447	Phase 1
0.7279	Intermediate Similarity	NPD7266	Discontinued
0.7279	Intermediate Similarity	NPD5763	Approved
0.7279	Intermediate Similarity	NPD5762	Approved
0.7273	Intermediate Similarity	NPD4380	Phase 2
0.7266	Intermediate Similarity	NPD6696	Suspended
0.7266	Intermediate Similarity	NPD2922	Phase 1
0.7254	Intermediate Similarity	NPD7095	Approved
0.7246	Intermediate Similarity	NPD2232	Approved
0.7246	Intermediate Similarity	NPD2230	Approved
0.7246	Intermediate Similarity	NPD2233	Approved
0.7244	Intermediate Similarity	NPD7819	Suspended
0.7236	Intermediate Similarity	NPD2859	Approved
0.7236	Intermediate Similarity	NPD2860	Approved
0.7219	Intermediate Similarity	NPD7212	Phase 2
0.7219	Intermediate Similarity	NPD7213	Phase 3
0.7211	Intermediate Similarity	NPD2935	Discontinued
0.7209	Intermediate Similarity	NPD290	Approved
0.7206	Intermediate Similarity	NPD5691	Approved
0.7206	Intermediate Similarity	NPD1651	Approved
0.7203	Intermediate Similarity	NPD3144	Approved
0.7203	Intermediate Similarity	NPD3145	Approved
0.72	Intermediate Similarity	NPD5241	Discontinued
0.7197	Intermediate Similarity	NPD2560	Approved
0.7197	Intermediate Similarity	NPD2563	Approved
0.7194	Intermediate Similarity	NPD1669	Approved
0.7186	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4236	Phase 3
0.7181	Intermediate Similarity	NPD4237	Approved
0.7172	Intermediate Similarity	NPD3657	Discovery
0.7172	Intermediate Similarity	NPD6355	Discontinued
0.7172	Intermediate Similarity	NPD5735	Approved
0.7172	Intermediate Similarity	NPD230	Phase 1
0.7171	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4624	Approved
0.7163	Intermediate Similarity	NPD6584	Phase 3
0.7162	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2933	Approved
0.7154	Intermediate Similarity	NPD2934	Approved
0.7154	Intermediate Similarity	NPD9296	Approved
0.7152	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD3748	Approved
0.7134	Intermediate Similarity	NPD4585	Approved
0.7133	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5494	Approved
0.7114	Intermediate Similarity	NPD1549	Phase 2
0.7114	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD9494	Approved
0.7108	Intermediate Similarity	NPD7251	Discontinued
0.7108	Intermediate Similarity	NPD7240	Approved
0.7107	Intermediate Similarity	NPD7075	Discontinued
0.7105	Intermediate Similarity	NPD7041	Phase 2
0.7105	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6799	Approved
0.7099	Intermediate Similarity	NPD5451	Approved
0.7097	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3094	Phase 2
0.7089	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6798	Discontinued
0.7075	Intermediate Similarity	NPD4536	Approved
0.7075	Intermediate Similarity	NPD6896	Approved
0.7075	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6895	Approved
0.7075	Intermediate Similarity	NPD4538	Approved
0.7073	Intermediate Similarity	NPD8252	Approved
0.7073	Intermediate Similarity	NPD8251	Approved
0.7073	Intermediate Similarity	NPD8099	Discontinued
0.7068	Intermediate Similarity	NPD7635	Approved
0.7067	Intermediate Similarity	NPD1652	Phase 2
0.7066	Intermediate Similarity	NPD7549	Discontinued
0.7066	Intermediate Similarity	NPD7808	Phase 3
0.7066	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4123	Phase 3
0.7059	Intermediate Similarity	NPD2532	Approved
0.7059	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD2533	Approved
0.7059	Intermediate Similarity	NPD4584	Approved
0.7055	Intermediate Similarity	NPD5124	Phase 1

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