NPASS Compound

Structure

NPC45146 OpenBabel07101719252D 29 31 0 0 0 0 0 0 0 0999 V2000 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 -1.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 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 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 0.0000 -2.0000 0.0000 C 0 0 0 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 4.3301 2.5000 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 -0.8660 -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 2.5981 -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 2.5981 -0.5000 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 -0.8660 -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 1.7321 0.0000 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 C 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 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 11 1 0 0 0 0 3 11 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 15 2 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 20 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 29 1 0 0 0 0 16 18 2 0 0 0 0 16 29 1 0 0 0 0 17 21 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	409.708
LogP:	5.639
LogD:	2.685
LogS:	-3.212
# Rotatable Bonds:	4
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.288
Synthetic Accessibility Score:	3.407
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.904
MDCK Permeability:	1.260035605810117e-05
Pgp-inhibitor:	0.855
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.298
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	92.96216583251953%
Volume Distribution (VD):	0.857
Pgp-substrate:	12.098764419555664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.762
CYP1A2-substrate:	0.258
CYP2C19-inhibitor:	0.468
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.776
CYP2C9-substrate:	0.791
CYP2D6-inhibitor:	0.662
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.167
CYP3A4-substrate:	0.075

ADMET: Excretion

Clearance (CL):	1.082
Half-life (T1/2):	0.579

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.349
AMES Toxicity:	0.508
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.31
Skin Sensitization:	0.93
Carcinogencity:	0.184
Eye Corrosion:	0.004
Eye Irritation:	0.912
Respiratory Toxicity:	0.26

Download Data

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

Natural Product: NPC45146

Natural Product ID:	NPC45146
*Common Name:**	1,3,6,7-Tetrahydroxy-2-(2-Methylbut-3-En-2-Yl)-8-(3-Methylbut-2-Enyl)Xanthen-9-One
IUPAC Name:	1,3,6,7-tetrahydroxy-2-(2-methylbut-3-en-2-yl)-8-(3-methylbut-2-enyl)xanthen-9-one
Synonyms:
Standard InCHIKey:	UVBQFJQAVCIWKR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-6-23(4,5)19-13(24)9-16-18(22(19)28)21(27)17-12(8-7-11(2)3)20(26)14(25)10-15(17)29-16/h6-7,9-10,24-26,28H,1,8H2,2-5H3
SMILES:	C=CC(c1c(O)cc2c(c1O)c(=O)c1c(o2)cc(c(c1CC=C(C)C)O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL249948
PubChem CID:	44156959
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003519] 8-prenylated xanthones

*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
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2
Ki	2

Activity Type	# Activity
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	127.4	nM	PMID[509828]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	80.0	nM	PMID[509828]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	58.0	nM	PMID[509828]
NPT2	Others	Unspecified		IC50	=	35800.0	nM	PMID[509827]

☑ 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 NPC45146 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	458
0.1-0.2	1863
0.2-0.3	4205
0.3-0.4	10684
0.4-0.5	7536
0.5-0.6	3573
0.6-0.7	5234
0.7-0.8	5265
0.8-0.85	2315
0.85-0.9	1164
0.9-0.95	353
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC235018
0.9934	High Similarity	NPC32694
0.9868	High Similarity	NPC80375
0.9805	High Similarity	NPC220313
0.9803	High Similarity	NPC172770
0.9803	High Similarity	NPC185258
0.9801	High Similarity	NPC142339
0.974	High Similarity	NPC470694
0.9737	High Similarity	NPC79053
0.9737	High Similarity	NPC236796
0.9675	High Similarity	NPC472275
0.9673	High Similarity	NPC100123
0.9673	High Similarity	NPC235448
0.9669	High Similarity	NPC89474
0.9615	High Similarity	NPC473286
0.9613	High Similarity	NPC329760
0.961	High Similarity	NPC228785
0.961	High Similarity	NPC119224
0.961	High Similarity	NPC320359
0.961	High Similarity	NPC56085
0.961	High Similarity	NPC14353
0.9551	High Similarity	NPC189473
0.9551	High Similarity	NPC23298
0.9551	High Similarity	NPC207690
0.9548	High Similarity	NPC40491
0.9548	High Similarity	NPC61010
0.9548	High Similarity	NPC278052
0.9542	High Similarity	NPC191146
0.9542	High Similarity	NPC68093
0.9542	High Similarity	NPC274730
0.9536	High Similarity	NPC202157
0.949	High Similarity	NPC239752
0.949	High Similarity	NPC472450
0.949	High Similarity	NPC275780
0.9487	High Similarity	NPC25152
0.9481	High Similarity	NPC187745
0.9481	High Similarity	NPC165977
0.9481	High Similarity	NPC300727
0.9481	High Similarity	NPC78225
0.9481	High Similarity	NPC217677
0.9481	High Similarity	NPC241904
0.9481	High Similarity	NPC136674
0.9481	High Similarity	NPC161960
0.9481	High Similarity	NPC304008
0.9477	High Similarity	NPC113906
0.947	High Similarity	NPC227122
0.943	High Similarity	NPC37870
0.943	High Similarity	NPC39091
0.943	High Similarity	NPC472449
0.9427	High Similarity	NPC7483
0.9427	High Similarity	NPC152659
0.9427	High Similarity	NPC236521
0.9427	High Similarity	NPC472278
0.9427	High Similarity	NPC329669
0.9427	High Similarity	NPC473313
0.9427	High Similarity	NPC236132
0.9427	High Similarity	NPC248638
0.9427	High Similarity	NPC306321
0.9427	High Similarity	NPC303460
0.9423	High Similarity	NPC474187
0.9419	High Similarity	NPC210459
0.9419	High Similarity	NPC46736
0.9419	High Similarity	NPC197856
0.9419	High Similarity	NPC476242
0.9419	High Similarity	NPC329091
0.9416	High Similarity	NPC3980
0.9416	High Similarity	NPC115853
0.9416	High Similarity	NPC138243
0.9367	High Similarity	NPC326520
0.9363	High Similarity	NPC229632
0.9363	High Similarity	NPC206605
0.9359	High Similarity	NPC200746
0.9359	High Similarity	NPC204290
0.9359	High Similarity	NPC321399
0.9359	High Similarity	NPC476280
0.9359	High Similarity	NPC474287
0.9359	High Similarity	NPC36217
0.9359	High Similarity	NPC297212
0.9359	High Similarity	NPC139036
0.9359	High Similarity	NPC475886
0.9359	High Similarity	NPC471973
0.9355	High Similarity	NPC262286
0.9355	High Similarity	NPC273843
0.9355	High Similarity	NPC36852
0.9355	High Similarity	NPC180011
0.9355	High Similarity	NPC219867
0.9351	High Similarity	NPC67396
0.9346	High Similarity	NPC249570
0.9342	High Similarity	NPC62042
0.9342	High Similarity	NPC3825
0.9342	High Similarity	NPC88804
0.9338	High Similarity	NPC276930
0.9308	High Similarity	NPC170245
0.9304	High Similarity	NPC12461
0.9304	High Similarity	NPC146134
0.9304	High Similarity	NPC270837
0.9299	High Similarity	NPC167678
0.9299	High Similarity	NPC474351
0.9299	High Similarity	NPC234644
0.9299	High Similarity	NPC29876
0.9299	High Similarity	NPC278427
0.9299	High Similarity	NPC474186
0.9299	High Similarity	NPC266314
0.9299	High Similarity	NPC475883
0.9295	High Similarity	NPC474290
0.9295	High Similarity	NPC85121
0.9295	High Similarity	NPC250214
0.9295	High Similarity	NPC95936
0.929	High Similarity	NPC13779
0.929	High Similarity	NPC475799
0.929	High Similarity	NPC24640
0.929	High Similarity	NPC276444
0.9286	High Similarity	NPC33051
0.9286	High Similarity	NPC280530
0.9286	High Similarity	NPC476631
0.9286	High Similarity	NPC213896
0.9286	High Similarity	NPC227337
0.9286	High Similarity	NPC178964
0.9286	High Similarity	NPC95842
0.9286	High Similarity	NPC273462
0.9286	High Similarity	NPC192083
0.9286	High Similarity	NPC70433
0.9286	High Similarity	NPC49402
0.925	High Similarity	NPC117854
0.925	High Similarity	NPC6588
0.925	High Similarity	NPC477154
0.9245	High Similarity	NPC472277
0.9245	High Similarity	NPC156432
0.9241	High Similarity	NPC294965
0.9241	High Similarity	NPC201800
0.9241	High Similarity	NPC83922
0.9241	High Similarity	NPC472448
0.9236	High Similarity	NPC476283
0.9236	High Similarity	NPC188433
0.9236	High Similarity	NPC476980
0.9231	High Similarity	NPC475267
0.9231	High Similarity	NPC223787
0.9231	High Similarity	NPC218871
0.9231	High Similarity	NPC472910
0.9231	High Similarity	NPC474836
0.9231	High Similarity	NPC245758
0.9231	High Similarity	NPC469584
0.9231	High Similarity	NPC472911
0.9231	High Similarity	NPC156057
0.9231	High Similarity	NPC48208
0.9231	High Similarity	NPC162869
0.9231	High Similarity	NPC476630
0.9231	High Similarity	NPC96167
0.9231	High Similarity	NPC472914
0.9231	High Similarity	NPC222814
0.9231	High Similarity	NPC472913
0.9231	High Similarity	NPC474208
0.9226	High Similarity	NPC117992
0.9226	High Similarity	NPC321779
0.9226	High Similarity	NPC152951
0.9226	High Similarity	NPC57674
0.9226	High Similarity	NPC230149
0.9226	High Similarity	NPC168247
0.9221	High Similarity	NPC63187
0.9221	High Similarity	NPC106976
0.9221	High Similarity	NPC157784
0.9221	High Similarity	NPC199100
0.9221	High Similarity	NPC120537
0.9221	High Similarity	NPC180234
0.9221	High Similarity	NPC37684
0.9216	High Similarity	NPC151473
0.9216	High Similarity	NPC61620
0.9216	High Similarity	NPC184136
0.9211	High Similarity	NPC194856
0.9211	High Similarity	NPC186397
0.9211	High Similarity	NPC37135
0.9187	High Similarity	NPC277480
0.9182	High Similarity	NPC186686
0.9182	High Similarity	NPC476295
0.9182	High Similarity	NPC187491
0.9182	High Similarity	NPC18100
0.9182	High Similarity	NPC41301
0.9182	High Similarity	NPC472281
0.9182	High Similarity	NPC474350
0.9182	High Similarity	NPC319200
0.9182	High Similarity	NPC475985
0.9182	High Similarity	NPC205265
0.9182	High Similarity	NPC197168
0.9177	High Similarity	NPC259456
0.9177	High Similarity	NPC57715
0.9177	High Similarity	NPC258331
0.9177	High Similarity	NPC472906
0.9177	High Similarity	NPC66288
0.9167	High Similarity	NPC472907
0.9167	High Similarity	NPC255106
0.9167	High Similarity	NPC278778
0.9167	High Similarity	NPC472916
0.9167	High Similarity	NPC291878
0.9167	High Similarity	NPC235165
0.9167	High Similarity	NPC195796
0.9167	High Similarity	NPC35038
0.9161	High Similarity	NPC274327
0.9161	High Similarity	NPC74924
0.9161	High Similarity	NPC69394
0.9161	High Similarity	NPC47781

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 NPC45146 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	1003
0.2-0.3	1682
0.3-0.4	2767
0.4-0.5	1793
0.5-0.6	936
0.6-0.7	396
0.7-0.8	127
0.8-0.85	26
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD2393	Clinical (unspecified phase)
0.9161	High Similarity	NPD2801	Approved
0.8974	High Similarity	NPD1934	Approved
0.8947	High Similarity	NPD1511	Approved
0.8831	High Similarity	NPD1512	Approved
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8642	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD3882	Suspended
0.8562	High Similarity	NPD7819	Suspended
0.8545	High Similarity	NPD6166	Phase 2
0.8545	High Similarity	NPD6167	Clinical (unspecified phase)
0.8545	High Similarity	NPD6168	Clinical (unspecified phase)
0.8537	High Similarity	NPD6232	Discontinued
0.8494	Intermediate Similarity	NPD7473	Discontinued
0.8393	Intermediate Similarity	NPD5844	Phase 1
0.8375	Intermediate Similarity	NPD4380	Phase 2
0.8364	Intermediate Similarity	NPD6959	Discontinued
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7074	Phase 3
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD1465	Phase 2
0.8323	Intermediate Similarity	NPD2800	Approved
0.8312	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7075	Discontinued
0.8291	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7054	Approved
0.8282	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD3817	Phase 2
0.8258	Intermediate Similarity	NPD1549	Phase 2
0.8235	Intermediate Similarity	NPD7472	Approved
0.8221	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6797	Phase 2
0.8158	Intermediate Similarity	NPD943	Approved
0.814	Intermediate Similarity	NPD7251	Discontinued
0.8098	Intermediate Similarity	NPD7411	Suspended
0.8072	Intermediate Similarity	NPD3749	Approved
0.8072	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1510	Phase 2
0.8063	Intermediate Similarity	NPD2532	Approved
0.8063	Intermediate Similarity	NPD2534	Approved
0.8063	Intermediate Similarity	NPD2533	Approved
0.8039	Intermediate Similarity	NPD1240	Approved
0.8038	Intermediate Similarity	NPD3750	Approved
0.8037	Intermediate Similarity	NPD6599	Discontinued
0.8025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6099	Approved
0.8013	Intermediate Similarity	NPD2796	Approved
0.8013	Intermediate Similarity	NPD6100	Approved
0.8013	Intermediate Similarity	NPD2935	Discontinued
0.7989	Intermediate Similarity	NPD7808	Phase 3
0.7975	Intermediate Similarity	NPD3226	Approved
0.7965	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2346	Discontinued
0.7949	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6801	Discontinued
0.7935	Intermediate Similarity	NPD1607	Approved
0.7929	Intermediate Similarity	NPD1247	Approved
0.7895	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6799	Approved
0.7874	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5402	Approved
0.7829	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6559	Discontinued
0.7821	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7768	Phase 2
0.7778	Intermediate Similarity	NPD7390	Discontinued
0.7735	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3926	Phase 2
0.773	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2799	Discontinued
0.7722	Intermediate Similarity	NPD3748	Approved
0.7707	Intermediate Similarity	NPD6651	Approved
0.7702	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1613	Approved
0.7692	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD230	Phase 1
0.764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2344	Approved
0.7613	Intermediate Similarity	NPD4625	Phase 3
0.7602	Intermediate Similarity	NPD919	Approved
0.7602	Intermediate Similarity	NPD6234	Discontinued
0.76	Intermediate Similarity	NPD3751	Discontinued
0.7593	Intermediate Similarity	NPD4628	Phase 3
0.7572	Intermediate Similarity	NPD3787	Discontinued
0.7572	Intermediate Similarity	NPD5710	Approved
0.7572	Intermediate Similarity	NPD5711	Approved
0.7564	Intermediate Similarity	NPD2313	Discontinued
0.7532	Intermediate Similarity	NPD447	Suspended
0.7531	Intermediate Similarity	NPD1243	Approved
0.753	Intermediate Similarity	NPD920	Approved
0.7515	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7199	Phase 2
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7459	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7286	Phase 2
0.7453	Intermediate Similarity	NPD1551	Phase 2
0.7452	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6782	Approved
0.7447	Intermediate Similarity	NPD6780	Approved
0.7447	Intermediate Similarity	NPD6778	Approved
0.7447	Intermediate Similarity	NPD6781	Approved
0.7447	Intermediate Similarity	NPD6776	Approved
0.7447	Intermediate Similarity	NPD6777	Approved
0.7447	Intermediate Similarity	NPD6779	Approved
0.7444	Intermediate Similarity	NPD8313	Approved
0.7444	Intermediate Similarity	NPD8312	Approved
0.7439	Intermediate Similarity	NPD2309	Approved
0.7429	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5403	Approved
0.7418	Intermediate Similarity	NPD8434	Phase 2
0.7412	Intermediate Similarity	NPD37	Approved
0.741	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7228	Approved
0.7389	Intermediate Similarity	NPD3027	Phase 3
0.7384	Intermediate Similarity	NPD4966	Approved
0.7384	Intermediate Similarity	NPD4965	Approved
0.7384	Intermediate Similarity	NPD4967	Phase 2
0.7371	Intermediate Similarity	NPD7229	Phase 3
0.7355	Intermediate Similarity	NPD1470	Approved
0.733	Intermediate Similarity	NPD7435	Discontinued
0.7325	Intermediate Similarity	NPD4908	Phase 1
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.732	Intermediate Similarity	NPD1201	Approved
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5401	Approved
0.7289	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1653	Approved
0.7273	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4360	Phase 2
0.7273	Intermediate Similarity	NPD4363	Phase 3
0.7246	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7783	Phase 2
0.7244	Intermediate Similarity	NPD1203	Approved
0.724	Intermediate Similarity	NPD7697	Approved
0.724	Intermediate Similarity	NPD7696	Phase 3
0.724	Intermediate Similarity	NPD7698	Approved
0.7239	Intermediate Similarity	NPD5404	Approved
0.7239	Intermediate Similarity	NPD5405	Approved
0.7239	Intermediate Similarity	NPD5406	Approved
0.7239	Intermediate Similarity	NPD5408	Approved
0.7235	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3268	Approved
0.7231	Intermediate Similarity	NPD8151	Discontinued
0.7229	Intermediate Similarity	NPD6190	Approved
0.7208	Intermediate Similarity	NPD1610	Phase 2
0.7205	Intermediate Similarity	NPD1933	Approved
0.7202	Intermediate Similarity	NPD7870	Phase 2
0.7202	Intermediate Similarity	NPD7871	Phase 2
0.7197	Intermediate Similarity	NPD2798	Approved
0.7195	Intermediate Similarity	NPD1471	Phase 3
0.7188	Intermediate Similarity	NPD6823	Phase 2
0.7181	Intermediate Similarity	NPD6534	Approved
0.7181	Intermediate Similarity	NPD6535	Approved
0.7179	Intermediate Similarity	NPD7701	Phase 2
0.7169	Intermediate Similarity	NPD7003	Approved
0.7161	Intermediate Similarity	NPD9269	Phase 2
0.7161	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD9494	Approved
0.7152	Intermediate Similarity	NPD2861	Phase 2
0.7151	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7135	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD2797	Approved
0.7126	Intermediate Similarity	NPD4288	Approved
0.7125	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3764	Approved
0.7115	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4749	Approved
0.711	Intermediate Similarity	NPD6844	Discontinued
0.7108	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7874	Approved
0.7107	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3300	Phase 2
0.7071	Intermediate Similarity	NPD7801	Approved
0.707	Intermediate Similarity	NPD6696	Suspended
0.7069	Intermediate Similarity	NPD5760	Phase 2
0.7069	Intermediate Similarity	NPD5761	Phase 2
0.7068	Intermediate Similarity	NPD7699	Phase 2
0.7068	Intermediate Similarity	NPD7700	Phase 2
0.7066	Intermediate Similarity	NPD8166	Discontinued
0.7059	Intermediate Similarity	NPD6273	Approved
0.7053	Intermediate Similarity	NPD4361	Phase 2
0.7053	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD9717	Approved
0.7051	Intermediate Similarity	NPD3972	Approved
0.7049	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7685	Pre-registration
0.7047	Intermediate Similarity	NPD2494	Approved
0.7047	Intermediate Similarity	NPD2493	Approved
0.7039	Intermediate Similarity	NPD5242	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