NPASS Compound

Structure

CID244903 OpenBabel06191716042D 35 40 0 0 1 0 0 0 0 0999 V2000 -2.3401 4.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7858 2.9850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5438 3.9553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8947 2.5658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9762 -4.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5114 -3.0164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7576 -0.1331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3379 1.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0666 2.2902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7193 -3.9946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9655 0.8451 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8065 -0.4421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9311 0.1225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4175 4.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0251 -4.3547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1368 3.5360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5604 -2.7074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3086 1.3200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1828 -3.3765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0634 0.2270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1338 -3.0675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3418 -2.0894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5986 -1.4202 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2224 1.5142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2713 1.2052 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6704 -4.3036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6595 5.2010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7180 -5.0238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8770 -3.7367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2928 -1.7804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4303 2.4923 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8591 2.0142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 3.8116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5947 1.7052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3524 -1.7293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 33 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 14 1 0 0 0 0 4 9 2 0 0 0 0 4 16 1 0 0 0 0 5 10 2 0 0 0 0 5 15 1 0 0 0 0 6 10 1 0 0 0 0 6 17 2 0 0 0 0 7 12 2 0 0 0 0 8 34 1 0 0 0 0 10 26 1 0 0 0 0 11 7 1 6 0 0 0 11 18 1 0 0 0 0 11 24 1 0 0 0 0 12 20 1 0 0 0 0 13 8 1 6 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 27 1 0 0 0 0 15 19 2 0 0 0 0 15 28 1 0 0 0 0 16 33 1 0 0 0 0 17 19 1 0 0 0 0 17 35 1 0 0 0 0 18 9 1 1 0 0 0 19 21 1 0 0 0 0 20 25 1 1 0 0 0 21 22 1 0 0 0 0 21 29 2 0 0 0 0 22 23 1 0 0 0 0 22 30 1 1 0 0 0 23 12 1 6 0 0 0 23 35 1 0 0 0 0 24 25 1 0 0 0 0 24 31 2 0 0 0 0 25 32 1 6 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.12
Volume:	453.791
LogP:	2.244
LogD:	1.717
LogS:	-3.521
# Rotatable Bonds:	3
TPSA:	166.89
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.373
Synthetic Accessibility Score:	5.753
Fsp3:	0.36
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.375
MDCK Permeability:	6.807412319176365e-06
Pgp-inhibitor:	0.181
Pgp-substrate:	0.79
Human Intestinal Absorption (HIA):	0.783
20% Bioavailability (F20%):	0.42
30% Bioavailability (F30%):	0.724

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	94.61882781982422%
Volume Distribution (VD):	0.526
Pgp-substrate:	7.038955211639404%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.91
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.183
CYP2C9-inhibitor:	0.626
CYP2C9-substrate:	0.635
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.358
CYP3A4-substrate:	0.705

ADMET: Excretion

Clearance (CL):	6.631
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.451
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.536
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.253
Respiratory Toxicity:	0.124

Download Data

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

Natural Product: NPC244903

Natural Product ID:	NPC244903
*Common Name:**	Silydianin
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CYGIJEJDYJOUAN-JSGXPVSSSA-N
Standard InCHI:	InChI=1S/C25H22O10/c1-33-16-4-9(2-3-14(16)27)18-11-7-12(20-13(18)8-34-25(20,32)24(11)31)23-22(30)21(29)19-15(28)5-10(26)6-17(19)35-23/h2-7,11,13,18,20,22-23,26-28,30,32H,8H2,1H3/t11-,13-,18+,20+,22+,23-,25-/m1/s1
SMILES:	COc1cc(ccc1O)[C@H]1[C@H]2C=C([C@H]3[C@@H]1CO[C@]3(C2=O)O)[C@@H]1[C@H](C(=O)c2c(cc(cc2O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2397733
PubChem CID:	11982272
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones

*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
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16394559]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24456525]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24597776]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5645	Silybum marianum	Species	Asteraceae	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	3
Ki	4
Others	4

Activity Type	# Activity
Individual Protein	10
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	KA	=	5.814	10'6L/mol	PMID[526267]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	KSV	=	0.1931	10'4L/mol	PMID[526267]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Kis	=	90.8	uM	PMID[526267]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	15000.0	nM	PMID[526267]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	14900.0	nM	PMID[526267]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	16500.0	nM	PMID[526267]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	2100.0	nM	PMID[526267]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	1700.0	nM	PMID[526267]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	2600.0	nM	PMID[526267]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Kis	=	2.3	uM	PMID[526267]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	130000.0	nM	PMID[526264]

☑ 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 NPC244903 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	424
0.1-0.2	1607
0.2-0.3	3243
0.3-0.4	7753
0.4-0.5	10124
0.5-0.6	5079
0.6-0.7	5187
0.7-0.8	6768
0.8-0.85	2197
0.85-0.9	305
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9401	High Similarity	NPC279209
0.9401	High Similarity	NPC102277
0.9226	High Similarity	NPC188079
0.9162	High Similarity	NPC7154
0.9162	High Similarity	NPC36
0.9162	High Similarity	NPC72787
0.9162	High Similarity	NPC36916
0.9162	High Similarity	NPC125039
0.9162	High Similarity	NPC7688
0.9162	High Similarity	NPC58223
0.9123	High Similarity	NPC294629
0.9118	High Similarity	NPC245452
0.9112	High Similarity	NPC203050
0.9112	High Similarity	NPC120099
0.9112	High Similarity	NPC219904
0.9112	High Similarity	NPC225434
0.9112	High Similarity	NPC223747
0.9112	High Similarity	NPC270578
0.9112	High Similarity	NPC52382
0.9096	High Similarity	NPC471499
0.9059	High Similarity	NPC72249
0.9059	High Similarity	NPC206123
0.9059	High Similarity	NPC95866
0.9053	High Similarity	NPC150131
0.9053	High Similarity	NPC92565
0.9053	High Similarity	NPC223424
0.9053	High Similarity	NPC127546
0.9053	High Similarity	NPC226304
0.9053	High Similarity	NPC317489
0.9053	High Similarity	NPC149244
0.9053	High Similarity	NPC52550
0.9053	High Similarity	NPC160156
0.9053	High Similarity	NPC84362
0.9053	High Similarity	NPC325555
0.9053	High Similarity	NPC173637
0.9053	High Similarity	NPC48640
0.9053	High Similarity	NPC265530
0.9042	High Similarity	NPC472635
0.9036	High Similarity	NPC470326
0.9036	High Similarity	NPC282009
0.9036	High Similarity	NPC287328
0.903	High Similarity	NPC471479
0.903	High Similarity	NPC471515
0.9023	High Similarity	NPC473073
0.9023	High Similarity	NPC473071
0.9023	High Similarity	NPC170203
0.9017	High Similarity	NPC168584
0.9017	High Similarity	NPC217520
0.9017	High Similarity	NPC139571
0.9012	High Similarity	NPC294815
0.9012	High Similarity	NPC220173
0.9012	High Similarity	NPC476472
0.9012	High Similarity	NPC16194
0.9012	High Similarity	NPC473327
0.9012	High Similarity	NPC19108
0.9012	High Similarity	NPC108202
0.9006	High Similarity	NPC33054
0.9006	High Similarity	NPC471725
0.9006	High Similarity	NPC153755
0.9006	High Similarity	NPC257667
0.9006	High Similarity	NPC261254
0.9006	High Similarity	NPC203259
0.9006	High Similarity	NPC235575
0.9006	High Similarity	NPC471748
0.9006	High Similarity	NPC176740
0.9006	High Similarity	NPC186847
0.9006	High Similarity	NPC155877
0.9006	High Similarity	NPC134532
0.9006	High Similarity	NPC4200
0.9006	High Similarity	NPC60735
0.9006	High Similarity	NPC472454
0.9006	High Similarity	NPC256760
0.9006	High Similarity	NPC26230
0.8994	High Similarity	NPC21100
0.8994	High Similarity	NPC471213
0.8994	High Similarity	NPC274618
0.8994	High Similarity	NPC5778
0.8994	High Similarity	NPC145038
0.8994	High Similarity	NPC281131
0.8994	High Similarity	NPC113968
0.8994	High Similarity	NPC255615
0.8994	High Similarity	NPC308404
0.8994	High Similarity	NPC253662
0.8994	High Similarity	NPC277174
0.8994	High Similarity	NPC67037
0.8994	High Similarity	NPC254306
0.8994	High Similarity	NPC314020
0.8994	High Similarity	NPC179950
0.8994	High Similarity	NPC118284
0.8994	High Similarity	NPC88789
0.8994	High Similarity	NPC236934
0.8994	High Similarity	NPC135599
0.8994	High Similarity	NPC197285
0.8994	High Similarity	NPC56077
0.8994	High Similarity	NPC73855
0.8994	High Similarity	NPC477517
0.8994	High Similarity	NPC276222
0.8994	High Similarity	NPC328940
0.8988	High Similarity	NPC472625
0.8982	High Similarity	NPC165970
0.8982	High Similarity	NPC158188
0.8982	High Similarity	NPC305987
0.8982	High Similarity	NPC289771
0.8982	High Similarity	NPC113163
0.8982	High Similarity	NPC84324
0.8982	High Similarity	NPC26326
0.8982	High Similarity	NPC112418
0.8982	High Similarity	NPC66618
0.8982	High Similarity	NPC288131
0.8982	High Similarity	NPC142252
0.8976	High Similarity	NPC22192
0.8971	High Similarity	NPC473072
0.897	High Similarity	NPC471500
0.897	High Similarity	NPC320825
0.897	High Similarity	NPC250922
0.897	High Similarity	NPC326037
0.897	High Similarity	NPC13858
0.8966	High Similarity	NPC212290
0.8953	High Similarity	NPC4390
0.8953	High Similarity	NPC101026
0.8953	High Similarity	NPC42773
0.8953	High Similarity	NPC24043
0.8953	High Similarity	NPC21666
0.8953	High Similarity	NPC45522
0.8953	High Similarity	NPC208668
0.8953	High Similarity	NPC169977
0.8947	High Similarity	NPC150767
0.8947	High Similarity	NPC285197
0.8947	High Similarity	NPC177731
0.8947	High Similarity	NPC78734
0.8947	High Similarity	NPC254855
0.8947	High Similarity	NPC105095
0.8947	High Similarity	NPC116864
0.8947	High Similarity	NPC255157
0.8947	High Similarity	NPC231194
0.8947	High Similarity	NPC67326
0.8947	High Similarity	NPC79056
0.8947	High Similarity	NPC51326
0.8947	High Similarity	NPC212748
0.8947	High Similarity	NPC67105
0.8947	High Similarity	NPC29958
0.8947	High Similarity	NPC259896
0.8947	High Similarity	NPC136042
0.8947	High Similarity	NPC44328
0.8947	High Similarity	NPC156869
0.8947	High Similarity	NPC244776
0.8941	High Similarity	NPC260266
0.8941	High Similarity	NPC229729
0.8941	High Similarity	NPC292233
0.8941	High Similarity	NPC476306
0.8941	High Similarity	NPC477502
0.8941	High Similarity	NPC474024
0.8941	High Similarity	NPC295082
0.8941	High Similarity	NPC42892
0.8935	High Similarity	NPC19388
0.8935	High Similarity	NPC240431
0.8935	High Similarity	NPC311830
0.8935	High Similarity	NPC22832
0.8935	High Similarity	NPC62261
0.8935	High Similarity	NPC34531
0.8935	High Similarity	NPC277205
0.8935	High Similarity	NPC475888
0.8935	High Similarity	NPC55786
0.8929	High Similarity	NPC300537
0.8929	High Similarity	NPC125991
0.8929	High Similarity	NPC127782
0.8929	High Similarity	NPC471745
0.8929	High Similarity	NPC211107
0.8929	High Similarity	NPC476247
0.8927	High Similarity	NPC174486
0.8922	High Similarity	NPC470183
0.8922	High Similarity	NPC306978
0.8922	High Similarity	NPC472624
0.8922	High Similarity	NPC471744
0.8922	High Similarity	NPC101731
0.8922	High Similarity	NPC36217
0.892	High Similarity	NPC148710
0.8916	High Similarity	NPC52530
0.8916	High Similarity	NPC474055
0.8916	High Similarity	NPC472598
0.8908	High Similarity	NPC35167
0.8908	High Similarity	NPC89052
0.8908	High Similarity	NPC477895
0.8908	High Similarity	NPC469600
0.8908	High Similarity	NPC173837
0.8908	High Similarity	NPC47191
0.8908	High Similarity	NPC251417
0.8902	High Similarity	NPC34267
0.8902	High Similarity	NPC223426
0.8902	High Similarity	NPC472607
0.8902	High Similarity	NPC214621
0.8902	High Similarity	NPC81042
0.8895	High Similarity	NPC175107
0.8895	High Similarity	NPC121333
0.8895	High Similarity	NPC476405
0.8895	High Similarity	NPC190003
0.8895	High Similarity	NPC117260
0.8889	High Similarity	NPC43587
0.8889	High Similarity	NPC209296
0.8889	High Similarity	NPC229687

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 NPC244903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	876
0.2-0.3	1799
0.3-0.4	2676
0.4-0.5	1939
0.5-0.6	964
0.6-0.7	383
0.7-0.8	125
0.8-0.85	19
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9162	High Similarity	NPD6166	Phase 2
0.9162	High Similarity	NPD6167	Clinical (unspecified phase)
0.9162	High Similarity	NPD6168	Clinical (unspecified phase)
0.9006	High Similarity	NPD6797	Phase 2
0.8953	High Similarity	NPD7251	Discontinued
0.8947	High Similarity	NPD7074	Phase 3
0.8902	High Similarity	NPD7808	Phase 3
0.8889	High Similarity	NPD7054	Approved
0.8837	High Similarity	NPD7472	Approved
0.883	High Similarity	NPD3818	Discontinued
0.8793	High Similarity	NPD4338	Clinical (unspecified phase)
0.8788	High Similarity	NPD1934	Approved
0.8743	High Similarity	NPD3882	Suspended
0.8735	High Similarity	NPD2393	Clinical (unspecified phase)
0.8671	High Similarity	NPD7804	Clinical (unspecified phase)
0.8571	High Similarity	NPD3817	Phase 2
0.848	Intermediate Similarity	NPD5494	Approved
0.8471	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7075	Discontinued
0.8412	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD2801	Approved
0.8362	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD5844	Phase 1
0.8343	Intermediate Similarity	NPD7473	Discontinued
0.8333	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8324	Intermediate Similarity	NPD6959	Discontinued
0.8315	Intermediate Similarity	NPD6559	Discontinued
0.8313	Intermediate Similarity	NPD1512	Approved
0.8295	Intermediate Similarity	NPD7228	Approved
0.8294	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6232	Discontinued
0.8246	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6801	Discontinued
0.8229	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD6234	Discontinued
0.8207	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD1511	Approved
0.8192	Intermediate Similarity	NPD3751	Discontinued
0.8144	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD37	Approved
0.8114	Intermediate Similarity	NPD7199	Phase 2
0.8098	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD4965	Approved
0.8092	Intermediate Similarity	NPD4966	Approved
0.8092	Intermediate Similarity	NPD4967	Phase 2
0.8081	Intermediate Similarity	NPD7819	Suspended
0.8068	Intermediate Similarity	NPD3787	Discontinued
0.8035	Intermediate Similarity	NPD5402	Approved
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.7977	Intermediate Similarity	NPD1465	Phase 2
0.7976	Intermediate Similarity	NPD6799	Approved
0.7965	Intermediate Similarity	NPD7411	Suspended
0.7941	Intermediate Similarity	NPD5403	Approved
0.7939	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD8312	Approved
0.7923	Intermediate Similarity	NPD8313	Approved
0.7898	Intermediate Similarity	NPD919	Approved
0.7892	Intermediate Similarity	NPD1549	Phase 2
0.7877	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD5401	Approved
0.7821	Intermediate Similarity	NPD3926	Phase 2
0.7814	Intermediate Similarity	NPD7240	Approved
0.7812	Intermediate Similarity	NPD6780	Approved
0.7812	Intermediate Similarity	NPD6776	Approved
0.7812	Intermediate Similarity	NPD6777	Approved
0.7812	Intermediate Similarity	NPD6779	Approved
0.7812	Intermediate Similarity	NPD6781	Approved
0.7812	Intermediate Similarity	NPD6778	Approved
0.7812	Intermediate Similarity	NPD6782	Approved
0.7809	Intermediate Similarity	NPD1247	Approved
0.7796	Intermediate Similarity	NPD8150	Discontinued
0.7796	Intermediate Similarity	NPD8434	Phase 2
0.7784	Intermediate Similarity	NPD7435	Discontinued
0.774	Intermediate Similarity	NPD3749	Approved
0.7719	Intermediate Similarity	NPD2534	Approved
0.7719	Intermediate Similarity	NPD2533	Approved
0.7719	Intermediate Similarity	NPD2532	Approved
0.7665	Intermediate Similarity	NPD2796	Approved
0.7622	Intermediate Similarity	NPD7685	Pre-registration
0.7605	Intermediate Similarity	NPD1510	Phase 2
0.7602	Intermediate Similarity	NPD7698	Approved
0.7602	Intermediate Similarity	NPD7696	Phase 3
0.7602	Intermediate Similarity	NPD7697	Approved
0.7588	Intermediate Similarity	NPD8151	Discontinued
0.7588	Intermediate Similarity	NPD3750	Approved
0.7584	Intermediate Similarity	NPD7768	Phase 2
0.7576	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1613	Approved
0.7574	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7870	Phase 2
0.7563	Intermediate Similarity	NPD7871	Phase 2
0.7558	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6535	Approved
0.7552	Intermediate Similarity	NPD6534	Approved
0.755	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7874	Approved
0.7544	Intermediate Similarity	NPD6190	Approved
0.7538	Intermediate Similarity	NPD7701	Phase 2
0.7529	Intermediate Similarity	NPD2800	Approved
0.7514	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7801	Approved
0.7487	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1653	Approved
0.7485	Intermediate Similarity	NPD1607	Approved
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7475	Intermediate Similarity	NPD8320	Phase 1
0.7475	Intermediate Similarity	NPD8319	Approved
0.7474	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1240	Approved
0.7457	Intermediate Similarity	NPD7390	Discontinued
0.7452	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD3226	Approved
0.7436	Intermediate Similarity	NPD7700	Phase 2
0.7436	Intermediate Similarity	NPD7699	Phase 2
0.7426	Intermediate Similarity	NPD7783	Phase 2
0.7426	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7680	Approved
0.7418	Intermediate Similarity	NPD8127	Discontinued
0.7394	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3027	Phase 3
0.7374	Intermediate Similarity	NPD6823	Phase 2
0.7374	Intermediate Similarity	NPD8455	Phase 2
0.7365	Intermediate Similarity	NPD943	Approved
0.736	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6100	Approved
0.7353	Intermediate Similarity	NPD6099	Approved
0.7345	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7458	Discontinued
0.7333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6674	Discontinued
0.7326	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD2494	Approved
0.7323	Intermediate Similarity	NPD2493	Approved
0.7314	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD2488	Approved
0.7306	Intermediate Similarity	NPD2490	Approved
0.73	Intermediate Similarity	NPD4582	Approved
0.73	Intermediate Similarity	NPD4583	Approved
0.7294	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3748	Approved
0.7283	Intermediate Similarity	NPD5711	Approved
0.7283	Intermediate Similarity	NPD5710	Approved
0.7283	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7907	Approved
0.726	Intermediate Similarity	NPD4111	Phase 1
0.726	Intermediate Similarity	NPD4665	Approved
0.7251	Intermediate Similarity	NPD1551	Phase 2
0.7251	Intermediate Similarity	NPD2935	Discontinued
0.725	Intermediate Similarity	NPD4002	Approved
0.725	Intermediate Similarity	NPD4004	Approved
0.7246	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3450	Approved
0.7236	Intermediate Similarity	NPD3452	Approved
0.7232	Intermediate Similarity	NPD920	Approved
0.7229	Intermediate Similarity	NPD4908	Phase 1
0.7228	Intermediate Similarity	NPD7584	Approved
0.7225	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD230	Phase 1
0.7219	Intermediate Similarity	NPD1933	Approved
0.7213	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2346	Discontinued
0.7204	Intermediate Similarity	NPD2403	Approved
0.72	Intermediate Similarity	NPD3057	Approved
0.7194	Intermediate Similarity	NPD4363	Phase 3
0.7194	Intermediate Similarity	NPD4360	Phase 2
0.7193	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7229	Phase 3
0.7184	Intermediate Similarity	NPD8166	Discontinued
0.7184	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6651	Approved
0.7175	Intermediate Similarity	NPD6273	Approved
0.716	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD6212	Phase 3
0.7143	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6213	Phase 3
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7126	Intermediate Similarity	NPD1243	Approved
0.7121	Intermediate Similarity	NPD2973	Approved
0.7121	Intermediate Similarity	NPD2975	Approved
0.7121	Intermediate Similarity	NPD2974	Approved
0.7119	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD447	Suspended
0.7114	Intermediate Similarity	NPD2491	Approved
0.7114	Intermediate Similarity	NPD3533	Approved
0.7114	Intermediate Similarity	NPD2972	Approved
0.7111	Intermediate Similarity	NPD7028	Phase 2
0.711	Intermediate Similarity	NPD7266	Discontinued
0.711	Intermediate Similarity	NPD2344	Approved
0.7105	Intermediate Similarity	NPD5953	Discontinued
0.7102	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4580	Approved
0.7093	Intermediate Similarity	NPD2799	Discontinued

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