NPASS Compound

Structure

CID100123 OpenBabel06191715442D 29 31 0 0 0 0 0 0 0 0999 V2000 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -1.7321 -3.0000 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 -2.5981 -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 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -1.7321 -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 -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 -2.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 1.7321 -3.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 12 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 16 1 0 0 0 0 14 21 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 20 2 0 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 27 1 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	409.708
LogP:	5.938
LogD:	2.909
LogS:	-2.639
# 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:	0.373
Synthetic Accessibility Score:	3.255
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.988
MDCK Permeability:	9.045932529261336e-06
Pgp-inhibitor:	0.447
Pgp-substrate:	0.936
Human Intestinal Absorption (HIA):	0.264
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	85.0685043334961%
Volume Distribution (VD):	0.821
Pgp-substrate:	14.159557342529297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.713
CYP1A2-substrate:	0.195
CYP2C19-inhibitor:	0.731
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.785
CYP2C9-substrate:	0.831
CYP2D6-inhibitor:	0.581
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.107
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	8.316
Half-life (T1/2):	0.635

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.909
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.557
Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.102
Skin Sensitization:	0.917
Carcinogencity:	0.095
Eye Corrosion:	0.003
Eye Irritation:	0.874
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC100123

Natural Product ID:	NPC100123
*Common Name:**	Cratoxyarborenone B
IUPAC Name:	1,3,5,7-tetrahydroxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
Synonyms:	cratoxyarborenone B
Standard InCHIKey:	AVGUAOZYPIBDIZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-11(2)5-7-13-15(24)9-17(26)23-19(13)22(28)20-18(29-23)10-16(25)14(21(20)27)8-6-12(3)4/h5-6,9-10,24-27H,7-8H2,1-4H3
SMILES:	CC(=CCc1c(cc(c2c1c(=O)c1c(cc(c(CC=C(C)C)c1O)O)o2)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465407
PubChem CID:	10475842
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
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	stem	n.a.	PMID[11908969]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11908969]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	twig	n.a.	PMID[11908969]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	roots	Daba desert reserve (50 km South of Amman), Jordan	2009-APR	PMID[21650157]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19501	Pseudosuberites hyalinus	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11770	Amphicome emodi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14950	Ardisia polycephala	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6106	Hymeniacidon perlevis	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18995	Gaultheria itoana	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17438	Polygala virgata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19560	Populus italica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18657	Galanthus gracilis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18005	Artemisia leucodes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19359	Parmotrema delicatulum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13263	Verbena brasiliensis	Species	Verbenaceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	1.0	ug.mL-1	PMID[544988]

☑ 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 NPC100123 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	467
0.1-0.2	1982
0.2-0.3	4683
0.3-0.4	11194
0.4-0.5	6564
0.5-0.6	3759
0.6-0.7	5020
0.7-0.8	5017
0.8-0.85	2180
0.85-0.9	1151
0.9-0.95	595
0.95-1	85

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC228785
0.9934	High Similarity	NPC320359
0.9934	High Similarity	NPC56085
0.9934	High Similarity	NPC14353
0.9868	High Similarity	NPC278052
0.9868	High Similarity	NPC61010
0.9868	High Similarity	NPC40491
0.9867	High Similarity	NPC274730
0.9867	High Similarity	NPC142339
0.9804	High Similarity	NPC25152
0.9801	High Similarity	NPC165977
0.9801	High Similarity	NPC241904
0.9801	High Similarity	NPC300727
0.9801	High Similarity	NPC236796
0.9801	High Similarity	NPC217677
0.974	High Similarity	NPC236521
0.974	High Similarity	NPC23298
0.974	High Similarity	NPC7483
0.974	High Similarity	NPC248638
0.974	High Similarity	NPC189473
0.974	High Similarity	NPC220313
0.974	High Similarity	NPC152659
0.974	High Similarity	NPC236132
0.9737	High Similarity	NPC476242
0.9735	High Similarity	NPC191146
0.9735	High Similarity	NPC68093
0.9735	High Similarity	NPC138243
0.9733	High Similarity	NPC89474
0.9677	High Similarity	NPC326520
0.9677	High Similarity	NPC472450
0.9677	High Similarity	NPC239752
0.9677	High Similarity	NPC275780
0.9673	High Similarity	NPC119224
0.9673	High Similarity	NPC475886
0.9673	High Similarity	NPC235018
0.9673	High Similarity	NPC474287
0.9673	High Similarity	NPC45146
0.9673	High Similarity	NPC200746
0.9671	High Similarity	NPC78225
0.9671	High Similarity	NPC36852
0.9671	High Similarity	NPC136674
0.9671	High Similarity	NPC262286
0.9615	High Similarity	NPC37870
0.9615	High Similarity	NPC472449
0.9615	High Similarity	NPC170245
0.9615	High Similarity	NPC39091
0.9613	High Similarity	NPC146134
0.9613	High Similarity	NPC270837
0.961	High Similarity	NPC474351
0.961	High Similarity	NPC32694
0.961	High Similarity	NPC475883
0.961	High Similarity	NPC474186
0.961	High Similarity	NPC474187
0.9608	High Similarity	NPC235448
0.96	High Similarity	NPC202157
0.9554	High Similarity	NPC6588
0.9554	High Similarity	NPC477154
0.9554	High Similarity	NPC117854
0.9548	High Similarity	NPC329760
0.9548	High Similarity	NPC294965
0.9548	High Similarity	NPC229632
0.9548	High Similarity	NPC470694
0.9545	High Similarity	NPC204290
0.9545	High Similarity	NPC80375
0.9545	High Similarity	NPC471973
0.9545	High Similarity	NPC139036
0.9545	High Similarity	NPC36217
0.9542	High Similarity	NPC223787
0.9542	High Similarity	NPC469584
0.9539	High Similarity	NPC113906
0.9533	High Similarity	NPC151473
0.9487	High Similarity	NPC475985
0.9487	High Similarity	NPC474350
0.9487	High Similarity	NPC197168
0.9487	High Similarity	NPC41301
0.9487	High Similarity	NPC207690
0.9484	High Similarity	NPC167678
0.9484	High Similarity	NPC29876
0.9484	High Similarity	NPC266314
0.9484	High Similarity	NPC66288
0.9481	High Similarity	NPC329091
0.9481	High Similarity	NPC250214
0.9481	High Similarity	NPC172770
0.9481	High Similarity	NPC95936
0.9481	High Similarity	NPC474290
0.9481	High Similarity	NPC185258
0.9474	High Similarity	NPC227337
0.9474	High Similarity	NPC273462
0.9474	High Similarity	NPC70433
0.9474	High Similarity	NPC49402
0.9474	High Similarity	NPC33051
0.9427	High Similarity	NPC473286
0.9427	High Similarity	NPC25361
0.9423	High Similarity	NPC201800
0.9423	High Similarity	NPC83922
0.9423	High Similarity	NPC472448
0.9423	High Similarity	NPC52204
0.9419	High Similarity	NPC246478
0.9419	High Similarity	NPC476980
0.9416	High Similarity	NPC474836
0.9416	High Similarity	NPC472910
0.9416	High Similarity	NPC472913
0.9416	High Similarity	NPC472914
0.9416	High Similarity	NPC48208
0.9416	High Similarity	NPC187745
0.9416	High Similarity	NPC96167
0.9416	High Similarity	NPC161960
0.9416	High Similarity	NPC474208
0.9416	High Similarity	NPC304008
0.9416	High Similarity	NPC156057
0.9416	High Similarity	NPC222814
0.9416	High Similarity	NPC162869
0.9416	High Similarity	NPC472911
0.9416	High Similarity	NPC245758
0.9416	High Similarity	NPC79053
0.9416	High Similarity	NPC475267
0.9412	High Similarity	NPC117992
0.9412	High Similarity	NPC230149
0.9412	High Similarity	NPC45849
0.9412	High Similarity	NPC200761
0.9412	High Similarity	NPC470327
0.9412	High Similarity	NPC57674
0.9412	High Similarity	NPC168247
0.9412	High Similarity	NPC152951
0.9412	High Similarity	NPC477503
0.9408	High Similarity	NPC199100
0.9408	High Similarity	NPC249570
0.9408	High Similarity	NPC180234
0.9408	High Similarity	NPC101996
0.9408	High Similarity	NPC471982
0.9408	High Similarity	NPC120537
0.9404	High Similarity	NPC61620
0.9404	High Similarity	NPC227122
0.9363	High Similarity	NPC186686
0.9363	High Similarity	NPC303460
0.9363	High Similarity	NPC306321
0.9359	High Similarity	NPC258331
0.9359	High Similarity	NPC259456
0.9359	High Similarity	NPC278427
0.9359	High Similarity	NPC472275
0.9355	High Similarity	NPC85121
0.9355	High Similarity	NPC210459
0.9351	High Similarity	NPC209614
0.9351	High Similarity	NPC278778
0.9351	High Similarity	NPC472916
0.9351	High Similarity	NPC472907
0.9351	High Similarity	NPC291878
0.9351	High Similarity	NPC255106
0.9351	High Similarity	NPC35038
0.9351	High Similarity	NPC470328
0.9351	High Similarity	NPC115853
0.9351	High Similarity	NPC472626
0.9351	High Similarity	NPC195796
0.9351	High Similarity	NPC235165
0.9351	High Similarity	NPC13779
0.9351	High Similarity	NPC475799
0.9346	High Similarity	NPC472905
0.9346	High Similarity	NPC176775
0.9346	High Similarity	NPC476631
0.9346	High Similarity	NPC292214
0.9346	High Similarity	NPC69394
0.9346	High Similarity	NPC47781
0.9346	High Similarity	NPC75279
0.9346	High Similarity	NPC22519
0.9346	High Similarity	NPC88645
0.9346	High Similarity	NPC160951
0.9346	High Similarity	NPC206238
0.9346	High Similarity	NPC255350
0.9346	High Similarity	NPC145379
0.9346	High Similarity	NPC167091
0.9346	High Similarity	NPC274327
0.9346	High Similarity	NPC271779
0.9346	High Similarity	NPC183878
0.9346	High Similarity	NPC276409
0.9346	High Similarity	NPC250822
0.9346	High Similarity	NPC231018
0.9342	High Similarity	NPC117579
0.9342	High Similarity	NPC171010
0.9342	High Similarity	NPC251110
0.9308	High Similarity	NPC126204
0.9304	High Similarity	NPC293319
0.9304	High Similarity	NPC475888
0.9299	High Similarity	NPC81679
0.9299	High Similarity	NPC474162
0.9299	High Similarity	NPC211107
0.9299	High Similarity	NPC474150
0.9295	High Similarity	NPC321399
0.9295	High Similarity	NPC299436
0.9295	High Similarity	NPC84571
0.929	High Similarity	NPC219867
0.929	High Similarity	NPC476981
0.929	High Similarity	NPC210084
0.929	High Similarity	NPC180011
0.929	High Similarity	NPC27337
0.929	High Similarity	NPC291508
0.929	High Similarity	NPC474055
0.929	High Similarity	NPC299520
0.929	High Similarity	NPC472963
0.929	High Similarity	NPC129684
0.929	High Similarity	NPC181960

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 NPC100123 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	1026
0.2-0.3	1852
0.3-0.4	2701
0.4-0.5	1739
0.5-0.6	900
0.6-0.7	340
0.7-0.8	129
0.8-0.85	26
0.85-0.9	13
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9346	High Similarity	NPD2801	Approved
0.9221	High Similarity	NPD2393	Clinical (unspecified phase)
0.9156	High Similarity	NPD1934	Approved
0.8882	High Similarity	NPD1511	Approved
0.8812	High Similarity	NPD5494	Approved
0.8766	High Similarity	NPD1512	Approved
0.8742	High Similarity	NPD3882	Suspended
0.8712	High Similarity	NPD6168	Clinical (unspecified phase)
0.8712	High Similarity	NPD6166	Phase 2
0.8712	High Similarity	NPD6167	Clinical (unspecified phase)
0.8704	High Similarity	NPD6232	Discontinued
0.8659	High Similarity	NPD7473	Discontinued
0.8616	High Similarity	NPD1465	Phase 2
0.8581	High Similarity	NPD4378	Clinical (unspecified phase)
0.8554	High Similarity	NPD5844	Phase 1
0.8509	High Similarity	NPD4868	Clinical (unspecified phase)
0.8503	High Similarity	NPD7074	Phase 3
0.85	High Similarity	NPD7819	Suspended
0.8494	Intermediate Similarity	NPD3818	Discontinued
0.8462	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD3817	Phase 2
0.8443	Intermediate Similarity	NPD7054	Approved
0.8428	Intermediate Similarity	NPD4380	Phase 2
0.8415	Intermediate Similarity	NPD6959	Discontinued
0.8393	Intermediate Similarity	NPD7472	Approved
0.8344	Intermediate Similarity	NPD7075	Discontinued
0.8272	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6797	Phase 2
0.8228	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1549	Phase 2
0.8187	Intermediate Similarity	NPD7251	Discontinued
0.8141	Intermediate Similarity	NPD2800	Approved
0.814	Intermediate Similarity	NPD7808	Phase 3
0.8121	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD2532	Approved
0.8113	Intermediate Similarity	NPD2534	Approved
0.8113	Intermediate Similarity	NPD2533	Approved
0.8092	Intermediate Similarity	NPD943	Approved
0.8084	Intermediate Similarity	NPD1247	Approved
0.8077	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7411	Suspended
0.8023	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3749	Approved
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7988	Intermediate Similarity	NPD6801	Discontinued
0.7975	Intermediate Similarity	NPD3750	Approved
0.7974	Intermediate Similarity	NPD1240	Approved
0.7966	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD2796	Approved
0.7949	Intermediate Similarity	NPD2935	Discontinued
0.7947	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6799	Approved
0.7914	Intermediate Similarity	NPD3226	Approved
0.7898	Intermediate Similarity	NPD2346	Discontinued
0.7892	Intermediate Similarity	NPD5402	Approved
0.7885	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3926	Phase 2
0.7874	Intermediate Similarity	NPD6559	Discontinued
0.7871	Intermediate Similarity	NPD1607	Approved
0.7869	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6599	Discontinued
0.7857	Intermediate Similarity	NPD6234	Discontinued
0.7836	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6100	Approved
0.7834	Intermediate Similarity	NPD6099	Approved
0.7826	Intermediate Similarity	NPD7390	Discontinued
0.7778	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD919	Approved
0.7742	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1613	Approved
0.7738	Intermediate Similarity	NPD7768	Phase 2
0.7692	Intermediate Similarity	NPD230	Phase 1
0.7692	Intermediate Similarity	NPD447	Suspended
0.7665	Intermediate Similarity	NPD37	Approved
0.7661	Intermediate Similarity	NPD7199	Phase 2
0.7658	Intermediate Similarity	NPD2799	Discontinued
0.7658	Intermediate Similarity	NPD3748	Approved
0.7644	Intermediate Similarity	NPD3751	Discontinued
0.7644	Intermediate Similarity	NPD7228	Approved
0.7633	Intermediate Similarity	NPD4966	Approved
0.7633	Intermediate Similarity	NPD4965	Approved
0.7633	Intermediate Similarity	NPD4967	Phase 2
0.7616	Intermediate Similarity	NPD5710	Approved
0.7616	Intermediate Similarity	NPD3787	Discontinued
0.7616	Intermediate Similarity	NPD5711	Approved
0.7598	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1243	Approved
0.7578	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2344	Approved
0.7561	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4625	Phase 3
0.7548	Intermediate Similarity	NPD3027	Phase 3
0.7532	Intermediate Similarity	NPD6651	Approved
0.7531	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2313	Discontinued
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7486	Intermediate Similarity	NPD8312	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.747	Intermediate Similarity	NPD5403	Approved
0.747	Intermediate Similarity	NPD920	Approved
0.743	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1653	Approved
0.7423	Intermediate Similarity	NPD4628	Phase 3
0.7416	Intermediate Similarity	NPD5953	Discontinued
0.7401	Intermediate Similarity	NPD7286	Phase 2
0.7394	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1551	Phase 2
0.7389	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2309	Approved
0.7368	Intermediate Similarity	NPD7435	Discontinued
0.7363	Intermediate Similarity	NPD8150	Discontinued
0.7358	Intermediate Similarity	NPD8151	Discontinued
0.7358	Intermediate Similarity	NPD1933	Approved
0.7349	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5401	Approved
0.7314	Intermediate Similarity	NPD7229	Phase 3
0.7308	Intermediate Similarity	NPD9494	Approved
0.729	Intermediate Similarity	NPD1470	Approved
0.7282	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7783	Phase 2
0.7277	Intermediate Similarity	NPD7698	Approved
0.7277	Intermediate Similarity	NPD7697	Approved
0.7277	Intermediate Similarity	NPD7696	Phase 3
0.7273	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8434	Phase 2
0.7261	Intermediate Similarity	NPD4908	Phase 1
0.7255	Intermediate Similarity	NPD1201	Approved
0.724	Intermediate Similarity	NPD7870	Phase 2
0.724	Intermediate Similarity	NPD7871	Phase 2
0.7229	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6823	Phase 2
0.7219	Intermediate Similarity	NPD4360	Phase 2
0.7219	Intermediate Similarity	NPD4363	Phase 3
0.7219	Intermediate Similarity	NPD6535	Approved
0.7219	Intermediate Similarity	NPD6534	Approved
0.7216	Intermediate Similarity	NPD7701	Phase 2
0.7212	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD9269	Phase 2
0.7188	Intermediate Similarity	NPD4060	Phase 1
0.7182	Intermediate Similarity	NPD7685	Pre-registration
0.7182	Intermediate Similarity	NPD7240	Approved
0.7179	Intermediate Similarity	NPD1203	Approved
0.7178	Intermediate Similarity	NPD5408	Approved
0.7178	Intermediate Similarity	NPD5406	Approved
0.7178	Intermediate Similarity	NPD5404	Approved
0.7178	Intermediate Similarity	NPD5405	Approved
0.7176	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5242	Approved
0.717	Intermediate Similarity	NPD3268	Approved
0.7161	Intermediate Similarity	NPD4749	Approved
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1610	Phase 2
0.7143	Intermediate Similarity	NPD7874	Approved
0.7135	Intermediate Similarity	NPD2403	Approved
0.7134	Intermediate Similarity	NPD1471	Phase 3
0.7134	Intermediate Similarity	NPD2798	Approved
0.7107	Intermediate Similarity	NPD7801	Approved
0.7105	Intermediate Similarity	NPD7700	Phase 2
0.7105	Intermediate Similarity	NPD7699	Phase 2
0.7097	Intermediate Similarity	NPD4287	Approved
0.7097	Intermediate Similarity	NPD1608	Approved
0.7093	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2861	Phase 2
0.707	Intermediate Similarity	NPD2797	Approved
0.7069	Intermediate Similarity	NPD5353	Approved
0.7069	Intermediate Similarity	NPD4288	Approved
0.7065	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3764	Approved
0.7053	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6844	Discontinued
0.7048	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6674	Discontinued
0.7041	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3300	Phase 2
0.7	Intermediate Similarity	NPD4361	Phase 2
0.7	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2493	Approved
0.6995	Remote Similarity	NPD2494	Approved
0.699	Remote Similarity	NPD7584	Approved
0.6988	Remote Similarity	NPD2424	Discontinued
0.6987	Remote Similarity	NPD9717	Approved
0.6984	Remote Similarity	NPD6212	Phase 3

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