NPASS Compound

Structure

NPC278506 OpenBabel07101719152D 36 38 0 0 1 0 0 0 0 0999 V2000 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3301 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 -3.4641 -1.0000 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 -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 0 0 0 0 0 0 0 0 0 0 6.0622 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 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 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 5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 13 1 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 10 33 1 0 0 0 0 11 1 1 6 0 0 0 11 34 1 0 0 0 0 12 5 1 6 0 0 0 12 24 1 0 0 0 0 13 26 2 0 0 0 0 14 9 1 6 0 0 0 14 16 1 0 0 0 0 14 35 1 0 0 0 0 15 10 1 1 0 0 0 15 17 1 0 0 0 0 15 36 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 1 0 0 0 17 19 1 0 0 0 0 17 28 1 6 0 0 0 18 20 1 0 0 0 0 18 29 1 6 0 0 0 19 21 1 0 0 0 0 19 30 1 1 0 0 0 20 22 1 0 0 0 0 20 31 1 1 0 0 0 21 23 1 0 0 0 0 21 32 1 6 0 0 0 22 33 1 6 0 0 0 22 35 1 0 0 0 0 23 34 1 1 0 0 0 23 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.25
Volume:	498.201
LogP:	-0.273
LogD:	-0.686
LogS:	-1.832
# Rotatable Bonds:	9
TPSA:	195.6
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.167
Synthetic Accessibility Score:	5.099
Fsp3:	0.875
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.73
MDCK Permeability:	5.521957791643217e-05
Pgp-inhibitor:	0.854
Pgp-substrate:	0.39
Human Intestinal Absorption (HIA):	0.945
20% Bioavailability (F20%):	0.85
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	51.33915328979492%
Volume Distribution (VD):	0.426
Pgp-substrate:	39.154476165771484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	0.975
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.35
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.027
Carcinogencity:	0.236
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.079

Download Data

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

Natural Product: NPC278506

Natural Product ID:	NPC278506
*Common Name:**	(6R,9R)-9-Hydroxy-4-Megastigmen-3-One 9-O-Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	(4S)-5,5-dimethyl-4-[(3R)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybutyl]cyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	XTJADGLZHRIXSG-ONWIAJSPSA-N
Standard InCHI:	InChI=1S/C24H40O12/c1-11(4-5-12-6-7-13(26)8-24(12,2)3)34-23-21(32)19(30)17(28)15(36-23)10-33-22-20(31)18(29)16(27)14(9-25)35-22/h6-7,11-12,14-23,25,27-32H,4-5,8-10H2,1-3H3/t11-,12+,14-,15-,16-,17-,18+,19+,20-,21-,22-,23-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H](CC[C@H]3C=CC(=O)CC3(C)C)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521317
PubChem CID:	44575745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620239]
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19123	Polygonatum zanlanscianense	Species	Asparagaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	20.05	ug.mL-1	PMID[503680]

☑ 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 NPC278506 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	209
0.1-0.2	1210
0.2-0.3	4591
0.3-0.4	8976
0.4-0.5	12399
0.5-0.6	7578
0.6-0.7	6273
0.7-0.8	1370
0.8-0.85	80
0.85-0.9	7
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9462	High Similarity	NPC56071
0.9462	High Similarity	NPC70733
0.914	High Similarity	NPC108141
0.8673	High Similarity	NPC476611
0.866	High Similarity	NPC40182
0.866	High Similarity	NPC198422
0.8586	High Similarity	NPC223834
0.8557	High Similarity	NPC476612
0.8557	High Similarity	NPC476613
0.8529	High Similarity	NPC473288
0.8529	High Similarity	NPC272576
0.8396	Intermediate Similarity	NPC165439
0.835	Intermediate Similarity	NPC177524
0.835	Intermediate Similarity	NPC392
0.835	Intermediate Similarity	NPC219900
0.8269	Intermediate Similarity	NPC246205
0.8265	Intermediate Similarity	NPC256230
0.8265	Intermediate Similarity	NPC143446
0.8247	Intermediate Similarity	NPC25701
0.8247	Intermediate Similarity	NPC2003
0.8224	Intermediate Similarity	NPC74727
0.8208	Intermediate Similarity	NPC471967
0.8165	Intermediate Similarity	NPC234522
0.8155	Intermediate Similarity	NPC210178
0.8148	Intermediate Similarity	NPC31797
0.8131	Intermediate Similarity	NPC477944
0.8131	Intermediate Similarity	NPC293038
0.8131	Intermediate Similarity	NPC62696
0.8131	Intermediate Similarity	NPC260665
0.8119	Intermediate Similarity	NPC154127
0.8105	Intermediate Similarity	NPC471755
0.8105	Intermediate Similarity	NPC471756
0.8095	Intermediate Similarity	NPC118225
0.8077	Intermediate Similarity	NPC293512
0.8073	Intermediate Similarity	NPC309433
0.8058	Intermediate Similarity	NPC121566
0.8058	Intermediate Similarity	NPC100955
0.8056	Intermediate Similarity	NPC102088
0.8037	Intermediate Similarity	NPC210420
0.8037	Intermediate Similarity	NPC474265
0.8019	Intermediate Similarity	NPC475317
0.8019	Intermediate Similarity	NPC475296
0.8019	Intermediate Similarity	NPC52241
0.8019	Intermediate Similarity	NPC279554
0.8019	Intermediate Similarity	NPC29069
0.8019	Intermediate Similarity	NPC136877
0.8019	Intermediate Similarity	NPC56713
0.8019	Intermediate Similarity	NPC474589
0.8019	Intermediate Similarity	NPC154856
0.8019	Intermediate Similarity	NPC269095
0.8019	Intermediate Similarity	NPC83005
0.8019	Intermediate Similarity	NPC59804
0.8019	Intermediate Similarity	NPC174679
0.8019	Intermediate Similarity	NPC90856
0.8019	Intermediate Similarity	NPC164194
0.8019	Intermediate Similarity	NPC270667
0.8019	Intermediate Similarity	NPC127056
0.8019	Intermediate Similarity	NPC78046
0.8018	Intermediate Similarity	NPC48692
0.8018	Intermediate Similarity	NPC308459
0.8	Intermediate Similarity	NPC176005
0.8	Intermediate Similarity	NPC474194
0.7982	Intermediate Similarity	NPC473126
0.7981	Intermediate Similarity	NPC162033
0.7981	Intermediate Similarity	NPC63023
0.7981	Intermediate Similarity	NPC95243
0.7961	Intermediate Similarity	NPC151516
0.7957	Intermediate Similarity	NPC470313
0.7957	Intermediate Similarity	NPC473500
0.7957	Intermediate Similarity	NPC156089
0.7957	Intermediate Similarity	NPC38295
0.7944	Intermediate Similarity	NPC108748
0.7944	Intermediate Similarity	NPC297208
0.7944	Intermediate Similarity	NPC235841
0.7944	Intermediate Similarity	NPC30397
0.7944	Intermediate Similarity	NPC164419
0.7944	Intermediate Similarity	NPC179434
0.7944	Intermediate Similarity	NPC473481
0.7944	Intermediate Similarity	NPC211798
0.7928	Intermediate Similarity	NPC127530
0.7928	Intermediate Similarity	NPC473401
0.7928	Intermediate Similarity	NPC197003
0.7928	Intermediate Similarity	NPC473920
0.7928	Intermediate Similarity	NPC279143
0.7928	Intermediate Similarity	NPC190939
0.7925	Intermediate Similarity	NPC237503
0.7925	Intermediate Similarity	NPC204407
0.7925	Intermediate Similarity	NPC57362
0.7925	Intermediate Similarity	NPC137917
0.7925	Intermediate Similarity	NPC306746
0.7925	Intermediate Similarity	NPC167383
0.7921	Intermediate Similarity	NPC61630
0.7921	Intermediate Similarity	NPC307517
0.7921	Intermediate Similarity	NPC81483
0.7921	Intermediate Similarity	NPC472015
0.7921	Intermediate Similarity	NPC469565
0.7921	Intermediate Similarity	NPC169468
0.7909	Intermediate Similarity	NPC474483
0.789	Intermediate Similarity	NPC473882
0.789	Intermediate Similarity	NPC474557
0.7885	Intermediate Similarity	NPC264584
0.7885	Intermediate Similarity	NPC223741
0.7879	Intermediate Similarity	NPC294293
0.787	Intermediate Similarity	NPC324875
0.787	Intermediate Similarity	NPC276093
0.787	Intermediate Similarity	NPC1046
0.787	Intermediate Similarity	NPC102439
0.787	Intermediate Similarity	NPC80843
0.787	Intermediate Similarity	NPC475516
0.787	Intermediate Similarity	NPC475504
0.787	Intermediate Similarity	NPC139044
0.787	Intermediate Similarity	NPC130427
0.787	Intermediate Similarity	NPC79718
0.787	Intermediate Similarity	NPC174836
0.787	Intermediate Similarity	NPC109079
0.787	Intermediate Similarity	NPC139894
0.787	Intermediate Similarity	NPC469946
0.787	Intermediate Similarity	NPC471383
0.787	Intermediate Similarity	NPC128925
0.787	Intermediate Similarity	NPC101744
0.787	Intermediate Similarity	NPC292677
0.787	Intermediate Similarity	NPC104400
0.787	Intermediate Similarity	NPC104071
0.787	Intermediate Similarity	NPC10320
0.787	Intermediate Similarity	NPC256798
0.787	Intermediate Similarity	NPC473373
0.787	Intermediate Similarity	NPC473383
0.787	Intermediate Similarity	NPC257468
0.7864	Intermediate Similarity	NPC476235
0.7864	Intermediate Similarity	NPC214277
0.7864	Intermediate Similarity	NPC476126
0.7864	Intermediate Similarity	NPC201191
0.7864	Intermediate Similarity	NPC150463
0.785	Intermediate Similarity	NPC199457
0.785	Intermediate Similarity	NPC476881
0.785	Intermediate Similarity	NPC476885
0.785	Intermediate Similarity	NPC220984
0.785	Intermediate Similarity	NPC476883
0.785	Intermediate Similarity	NPC110139
0.785	Intermediate Similarity	NPC274507
0.785	Intermediate Similarity	NPC75747
0.785	Intermediate Similarity	NPC476886
0.785	Intermediate Similarity	NPC114961
0.785	Intermediate Similarity	NPC102914
0.785	Intermediate Similarity	NPC476882
0.785	Intermediate Similarity	NPC476880
0.785	Intermediate Similarity	NPC476887
0.785	Intermediate Similarity	NPC7870
0.785	Intermediate Similarity	NPC129340
0.785	Intermediate Similarity	NPC127153
0.785	Intermediate Similarity	NPC476884
0.785	Intermediate Similarity	NPC68419
0.785	Intermediate Similarity	NPC108709
0.785	Intermediate Similarity	NPC27551
0.7849	Intermediate Similarity	NPC20072
0.7838	Intermediate Similarity	NPC13710
0.783	Intermediate Similarity	NPC295389
0.783	Intermediate Similarity	NPC177246
0.783	Intermediate Similarity	NPC476123
0.783	Intermediate Similarity	NPC28198
0.783	Intermediate Similarity	NPC284807
0.7822	Intermediate Similarity	NPC96597
0.7822	Intermediate Similarity	NPC309503
0.7822	Intermediate Similarity	NPC125551
0.7822	Intermediate Similarity	NPC155319
0.7822	Intermediate Similarity	NPC239547
0.7822	Intermediate Similarity	NPC91197
0.7822	Intermediate Similarity	NPC266842
0.7818	Intermediate Similarity	NPC279638
0.781	Intermediate Similarity	NPC476740
0.781	Intermediate Similarity	NPC82251
0.781	Intermediate Similarity	NPC476738
0.7798	Intermediate Similarity	NPC134835
0.7798	Intermediate Similarity	NPC311592
0.7798	Intermediate Similarity	NPC75167
0.7798	Intermediate Similarity	NPC475287
0.7798	Intermediate Similarity	NPC114304
0.7798	Intermediate Similarity	NPC73318
0.7798	Intermediate Similarity	NPC251309
0.7798	Intermediate Similarity	NPC166422
0.7798	Intermediate Similarity	NPC471173
0.7798	Intermediate Similarity	NPC473343
0.7798	Intermediate Similarity	NPC258885
0.7798	Intermediate Similarity	NPC475467
0.7798	Intermediate Similarity	NPC238935
0.7798	Intermediate Similarity	NPC473826
0.7798	Intermediate Similarity	NPC471627
0.7798	Intermediate Similarity	NPC138334
0.7798	Intermediate Similarity	NPC192600
0.7798	Intermediate Similarity	NPC96641
0.7798	Intermediate Similarity	NPC309714
0.7798	Intermediate Similarity	NPC150400
0.7798	Intermediate Similarity	NPC174720
0.7798	Intermediate Similarity	NPC133818
0.7798	Intermediate Similarity	NPC124296
0.7798	Intermediate Similarity	NPC155410
0.7798	Intermediate Similarity	NPC73455
0.7798	Intermediate Similarity	NPC47063
0.7798	Intermediate Similarity	NPC241909
0.7798	Intermediate Similarity	NPC251263

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 NPC278506 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1587
0.2-0.3	3872
0.3-0.4	2299
0.4-0.5	685
0.5-0.6	276
0.6-0.7	226
0.7-0.8	18
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8431	Intermediate Similarity	NPD6412	Phase 2
0.835	Intermediate Similarity	NPD6686	Approved
0.7652	Intermediate Similarity	NPD8328	Phase 3
0.7593	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6370	Approved
0.74	Intermediate Similarity	NPD6698	Approved
0.74	Intermediate Similarity	NPD46	Approved
0.7241	Intermediate Similarity	NPD6054	Approved
0.7238	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7736	Approved
0.7083	Intermediate Similarity	NPD7507	Approved
0.708	Intermediate Similarity	NPD6882	Approved
0.7069	Intermediate Similarity	NPD7641	Discontinued
0.7034	Intermediate Similarity	NPD8517	Approved
0.7034	Intermediate Similarity	NPD7503	Approved
0.7034	Intermediate Similarity	NPD6016	Approved
0.7034	Intermediate Similarity	NPD8513	Phase 3
0.7034	Intermediate Similarity	NPD8516	Approved
0.7034	Intermediate Similarity	NPD8515	Approved
0.7034	Intermediate Similarity	NPD6015	Approved
0.7019	Intermediate Similarity	NPD5282	Discontinued
0.7018	Intermediate Similarity	NPD8133	Approved
0.7	Intermediate Similarity	NPD7492	Approved
0.699	Remote Similarity	NPD6411	Approved
0.6983	Remote Similarity	NPD6009	Approved
0.6975	Remote Similarity	NPD5988	Approved
0.6949	Remote Similarity	NPD6319	Approved
0.6949	Remote Similarity	NPD6059	Approved
0.6942	Remote Similarity	NPD6616	Approved
0.693	Remote Similarity	NPD8297	Approved
0.6917	Remote Similarity	NPD7829	Approved
0.6917	Remote Similarity	NPD6067	Discontinued
0.6917	Remote Similarity	NPD7830	Approved
0.6911	Remote Similarity	NPD7319	Approved
0.6893	Remote Similarity	NPD7838	Discovery
0.6885	Remote Similarity	NPD7078	Approved
0.6885	Remote Similarity	NPD8293	Discontinued
0.687	Remote Similarity	NPD4632	Approved
0.6827	Remote Similarity	NPD7983	Approved
0.6807	Remote Similarity	NPD8377	Approved
0.6807	Remote Similarity	NPD8294	Approved
0.6796	Remote Similarity	NPD6101	Approved
0.6796	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7328	Approved
0.678	Remote Similarity	NPD7327	Approved
0.6754	Remote Similarity	NPD6371	Approved
0.675	Remote Similarity	NPD8335	Approved
0.675	Remote Similarity	NPD8296	Approved
0.675	Remote Similarity	NPD8378	Approved
0.675	Remote Similarity	NPD8380	Approved
0.675	Remote Similarity	NPD8379	Approved
0.675	Remote Similarity	NPD8033	Approved
0.6726	Remote Similarity	NPD6899	Approved
0.6726	Remote Similarity	NPD6881	Approved
0.6723	Remote Similarity	NPD7516	Approved
0.6698	Remote Similarity	NPD7748	Approved
0.6696	Remote Similarity	NPD6650	Approved
0.6696	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.6639	Remote Similarity	NPD7642	Approved
0.6637	Remote Similarity	NPD5697	Approved
0.6634	Remote Similarity	NPD3665	Phase 1
0.6634	Remote Similarity	NPD3666	Approved
0.6634	Remote Similarity	NPD3133	Approved
0.6609	Remote Similarity	NPD7102	Approved
0.6609	Remote Similarity	NPD6883	Approved
0.6609	Remote Similarity	NPD4634	Approved
0.6609	Remote Similarity	NPD7290	Approved
0.6607	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5778	Approved
0.6604	Remote Similarity	NPD5779	Approved
0.6604	Remote Similarity	NPD6399	Phase 3
0.66	Remote Similarity	NPD6435	Approved
0.6587	Remote Similarity	NPD5956	Approved
0.6585	Remote Similarity	NPD8342	Approved
0.6585	Remote Similarity	NPD8341	Approved
0.6585	Remote Similarity	NPD8340	Approved
0.6585	Remote Similarity	NPD8299	Approved
0.6579	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4695	Discontinued
0.656	Remote Similarity	NPD8336	Approved
0.656	Remote Similarity	NPD8337	Approved
0.6557	Remote Similarity	NPD8080	Discontinued
0.6555	Remote Similarity	NPD7115	Discovery
0.6552	Remote Similarity	NPD8130	Phase 1
0.6552	Remote Similarity	NPD6617	Approved
0.6552	Remote Similarity	NPD6869	Approved
0.6552	Remote Similarity	NPD6847	Approved
0.6549	Remote Similarity	NPD5739	Approved
0.6549	Remote Similarity	NPD6402	Approved
0.6549	Remote Similarity	NPD7128	Approved
0.6549	Remote Similarity	NPD6675	Approved
0.6545	Remote Similarity	NPD4696	Approved
0.6545	Remote Similarity	NPD5285	Approved
0.6545	Remote Similarity	NPD5286	Approved
0.6532	Remote Similarity	NPD8451	Approved
0.6522	Remote Similarity	NPD6372	Approved
0.6522	Remote Similarity	NPD6013	Approved
0.6522	Remote Similarity	NPD6014	Approved
0.6522	Remote Similarity	NPD6012	Approved
0.6522	Remote Similarity	NPD6373	Approved
0.6522	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD3618	Phase 1
0.6505	Remote Similarity	NPD7334	Approved
0.6505	Remote Similarity	NPD5279	Phase 3
0.6505	Remote Similarity	NPD6409	Approved
0.6505	Remote Similarity	NPD7521	Approved
0.6505	Remote Similarity	NPD5330	Approved
0.6505	Remote Similarity	NPD7146	Approved
0.6505	Remote Similarity	NPD6684	Approved
0.6504	Remote Similarity	NPD7604	Phase 2
0.6491	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5695	Phase 3
0.6481	Remote Similarity	NPD4629	Approved
0.6481	Remote Similarity	NPD5210	Approved
0.648	Remote Similarity	NPD8448	Approved
0.648	Remote Similarity	NPD8074	Phase 3
0.6476	Remote Similarity	NPD4753	Phase 2
0.6476	Remote Similarity	NPD5328	Approved
0.6475	Remote Similarity	NPD8444	Approved
0.6475	Remote Similarity	NPD5983	Phase 2
0.6471	Remote Similarity	NPD4786	Approved
0.6457	Remote Similarity	NPD8390	Approved
0.6457	Remote Similarity	NPD8392	Approved
0.6457	Remote Similarity	NPD8391	Approved
0.6455	Remote Similarity	NPD7638	Approved
0.6436	Remote Similarity	NPD3667	Approved
0.6435	Remote Similarity	NPD6011	Approved
0.6435	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD5226	Approved
0.6429	Remote Similarity	NPD6033	Approved
0.6429	Remote Similarity	NPD5224	Approved
0.6429	Remote Similarity	NPD5211	Phase 2
0.6429	Remote Similarity	NPD5225	Approved
0.6429	Remote Similarity	NPD4633	Approved
0.6422	Remote Similarity	NPD7839	Suspended
0.6422	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5222	Approved
0.6422	Remote Similarity	NPD5221	Approved
0.6417	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5785	Approved
0.64	Remote Similarity	NPD5368	Approved
0.64	Remote Similarity	NPD6336	Discontinued
0.6396	Remote Similarity	NPD7640	Approved
0.6396	Remote Similarity	NPD7639	Approved
0.6389	Remote Similarity	NPD7900	Approved
0.6389	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6903	Approved
0.6381	Remote Similarity	NPD5737	Approved
0.6381	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6672	Approved
0.6373	Remote Similarity	NPD6110	Phase 1
0.6372	Remote Similarity	NPD5175	Approved
0.6372	Remote Similarity	NPD5174	Approved
0.6364	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD4755	Approved
0.6364	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD8338	Approved
0.6348	Remote Similarity	NPD5701	Approved
0.6341	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5223	Approved
0.6339	Remote Similarity	NPD5344	Discontinued
0.6325	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5141	Approved
0.6311	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5696	Approved
0.6306	Remote Similarity	NPD4225	Approved
0.6296	Remote Similarity	NPD4202	Approved
0.6293	Remote Similarity	NPD4730	Approved
0.6293	Remote Similarity	NPD4729	Approved
0.6286	Remote Similarity	NPD3573	Approved
0.6279	Remote Similarity	NPD7260	Phase 2
0.625	Remote Similarity	NPD4700	Approved
0.625	Remote Similarity	NPD1694	Approved
0.625	Remote Similarity	NPD5363	Approved
0.6238	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6053	Discontinued
0.6204	Remote Similarity	NPD5284	Approved
0.6204	Remote Similarity	NPD5281	Approved
0.6202	Remote Similarity	NPD6914	Discontinued
0.619	Remote Similarity	NPD5690	Phase 2
0.6186	Remote Similarity	NPD5249	Phase 3
0.6186	Remote Similarity	NPD5248	Approved
0.6186	Remote Similarity	NPD5250	Approved
0.6186	Remote Similarity	NPD5247	Approved
0.6186	Remote Similarity	NPD5251	Approved
0.6179	Remote Similarity	NPD4522	Approved
0.6179	Remote Similarity	NPD7100	Approved
0.6179	Remote Similarity	NPD7101	Approved
0.6176	Remote Similarity	NPD5369	Approved
0.6165	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7500	Approved
0.614	Remote Similarity	NPD8138	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