NPASS Compound

Structure

NPC474290 OpenBabel07101718332D 28 31 0 0 1 0 0 0 0 0999 V2000 -3.1566 -2.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7083 -4.4154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 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 -1.2247 -2.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4836 -3.1907 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -1.9659 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 -2.4495 -3.4495 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 5.1962 -0.0000 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 4.3301 1.5000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -0.0000 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1962 -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 3.4641 -1.0000 0.0000 O 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 23 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 13 2 0 0 0 0 7 15 1 0 0 0 0 8 17 2 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 23 1 0 0 0 0 11 23 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 22 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 21 1 0 0 0 0 19 22 2 0 0 0 0 20 21 1 0 0 0 0 21 26 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.15
Volume:	392.361
LogP:	5.098
LogD:	3.045
LogS:	-4.097
# Rotatable Bonds:	3
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	4.062
Fsp3:	0.304
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:	-4.795
MDCK Permeability:	1.6626556316623464e-05
Pgp-inhibitor:	0.432
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.184

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	74.43445587158203%
Volume Distribution (VD):	1.224
Pgp-substrate:	12.930477142333984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.919
CYP1A2-substrate:	0.475
CYP2C19-inhibitor:	0.647
CYP2C19-substrate:	0.291
CYP2C9-inhibitor:	0.643
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.628
CYP2D6-substrate:	0.206
CYP3A4-inhibitor:	0.265
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	1.973
Half-life (T1/2):	0.211

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.952
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.213
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.242
Skin Sensitization:	0.835
Carcinogencity:	0.891
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.269

Download Data

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

Natural Product: NPC474290

Natural Product ID:	NPC474290
*Common Name:**	Globulixanthone B
IUPAC Name:	6,11-dihydroxy-3-methyl-3-(4-methylpent-3-enyl)pyrano[3,2-a]xanthen-12-one
Synonyms:	globulixanthone B
Standard InCHIKey:	DZEKDJJYJJYEFB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H22O5/c1-13(2)6-5-10-23(3)11-9-14-18(28-23)12-16(25)22-19(14)21(26)20-15(24)7-4-8-17(20)27-22/h4,6-9,11-12,24-25H,5,10H2,1-3H3
SMILES:	CC(=CCCC1(C=CC2=C(O1)C=C(C3=C2C(=O)C4=C(C=CC=C4O3)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464752
PubChem CID:	10452251
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:0003521] Pyranoxanthones

*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
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	Tanzania	n.a.	PMID[11430019]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[12027753]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12502337]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17960072]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	root	n.a.	PMID[17960072]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26221771]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8408	Symphonia globulifera	Species	Clusiaceae	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
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.78	ug.mL-1	PMID[572725]

☑ 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 NPC474290 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	1921
0.2-0.3	4679
0.3-0.4	11070
0.4-0.5	6631
0.5-0.6	3692
0.6-0.7	5224
0.7-0.8	5147
0.8-0.85	2082
0.85-0.9	1105
0.9-0.95	638
0.95-1	41

Similarity Score	Similarity Level	Natural Product ID
0.9803	High Similarity	NPC139036
0.974	High Similarity	NPC23298
0.974	High Similarity	NPC189473
0.9677	High Similarity	NPC472450
0.9677	High Similarity	NPC239752
0.9677	High Similarity	NPC275780
0.9673	High Similarity	NPC200746
0.9615	High Similarity	NPC37870
0.9615	High Similarity	NPC472449
0.9615	High Similarity	NPC39091
0.9608	High Similarity	NPC476242
0.9605	High Similarity	NPC274730
0.9548	High Similarity	NPC25152
0.9548	High Similarity	NPC229632
0.9548	High Similarity	NPC329760
0.9545	High Similarity	NPC471973
0.9545	High Similarity	NPC204290
0.9542	High Similarity	NPC300727
0.9542	High Similarity	NPC241904
0.9487	High Similarity	NPC152659
0.9487	High Similarity	NPC236521
0.9487	High Similarity	NPC207690
0.9487	High Similarity	NPC248638
0.9484	High Similarity	NPC61010
0.9484	High Similarity	NPC167678
0.9484	High Similarity	NPC29876
0.9481	High Similarity	NPC100123
0.9474	High Similarity	NPC89474
0.9423	High Similarity	NPC83922
0.9423	High Similarity	NPC472448
0.9419	High Similarity	NPC228785
0.9419	High Similarity	NPC14353
0.9419	High Similarity	NPC56085
0.9419	High Similarity	NPC474960
0.9419	High Similarity	NPC320359
0.9416	High Similarity	NPC136674
0.9363	High Similarity	NPC220313
0.9363	High Similarity	NPC475985
0.9363	High Similarity	NPC186686
0.9363	High Similarity	NPC146134
0.9363	High Similarity	NPC303460
0.9363	High Similarity	NPC306321
0.9359	High Similarity	NPC259456
0.9359	High Similarity	NPC278052
0.9359	High Similarity	NPC40491
0.9355	High Similarity	NPC280680
0.9351	High Similarity	NPC472907
0.9351	High Similarity	NPC191146
0.9351	High Similarity	NPC68093
0.9351	High Similarity	NPC142339
0.9346	High Similarity	NPC472905
0.9346	High Similarity	NPC176775
0.9346	High Similarity	NPC47781
0.9346	High Similarity	NPC22519
0.9346	High Similarity	NPC160951
0.9346	High Similarity	NPC255350
0.9346	High Similarity	NPC69394
0.9346	High Similarity	NPC145379
0.9346	High Similarity	NPC274327
0.9346	High Similarity	NPC183878
0.9346	High Similarity	NPC231018
0.9342	High Similarity	NPC202157
0.9308	High Similarity	NPC477154
0.9308	High Similarity	NPC6588
0.9308	High Similarity	NPC117854
0.9304	High Similarity	NPC224280
0.9299	High Similarity	NPC474162
0.9299	High Similarity	NPC474150
0.9295	High Similarity	NPC476980
0.9295	High Similarity	NPC45146
0.9295	High Similarity	NPC80375
0.9295	High Similarity	NPC235018
0.929	High Similarity	NPC474681
0.929	High Similarity	NPC217677
0.929	High Similarity	NPC475267
0.929	High Similarity	NPC472911
0.929	High Similarity	NPC165977
0.929	High Similarity	NPC156057
0.929	High Similarity	NPC472963
0.929	High Similarity	NPC469584
0.929	High Similarity	NPC472913
0.929	High Similarity	NPC472914
0.929	High Similarity	NPC474208
0.929	High Similarity	NPC236796
0.929	High Similarity	NPC474836
0.929	High Similarity	NPC48208
0.929	High Similarity	NPC96167
0.929	High Similarity	NPC245758
0.929	High Similarity	NPC78225
0.929	High Similarity	NPC162869
0.929	High Similarity	NPC218313
0.929	High Similarity	NPC222814
0.929	High Similarity	NPC472910
0.9286	High Similarity	NPC4455
0.9286	High Similarity	NPC163780
0.9286	High Similarity	NPC2476
0.9286	High Similarity	NPC128863
0.9286	High Similarity	NPC138360
0.9286	High Similarity	NPC280339
0.9286	High Similarity	NPC213622
0.9286	High Similarity	NPC256612
0.9286	High Similarity	NPC201136
0.9286	High Similarity	NPC146165
0.9286	High Similarity	NPC92659
0.9286	High Similarity	NPC167815
0.9286	High Similarity	NPC196439
0.9286	High Similarity	NPC50715
0.9286	High Similarity	NPC183597
0.9286	High Similarity	NPC20830
0.9286	High Similarity	NPC227325
0.9281	High Similarity	NPC293183
0.9281	High Similarity	NPC222830
0.9281	High Similarity	NPC198826
0.9281	High Similarity	NPC241498
0.9281	High Similarity	NPC75069
0.9281	High Similarity	NPC131624
0.9281	High Similarity	NPC275722
0.9281	High Similarity	NPC212678
0.9281	High Similarity	NPC301323
0.9281	High Similarity	NPC25270
0.9281	High Similarity	NPC120163
0.9281	High Similarity	NPC199100
0.9281	High Similarity	NPC275836
0.9281	High Similarity	NPC180234
0.9281	High Similarity	NPC100887
0.9281	High Similarity	NPC120537
0.9281	High Similarity	NPC256283
0.9281	High Similarity	NPC57030
0.9281	High Similarity	NPC83508
0.9281	High Similarity	NPC71334
0.9281	High Similarity	NPC156222
0.9281	High Similarity	NPC187498
0.9281	High Similarity	NPC239128
0.9281	High Similarity	NPC188203
0.9281	High Similarity	NPC162313
0.9276	High Similarity	NPC151473
0.9276	High Similarity	NPC61620
0.925	High Similarity	NPC476637
0.9245	High Similarity	NPC43319
0.9245	High Similarity	NPC170245
0.9241	High Similarity	NPC270837
0.9241	High Similarity	NPC7483
0.9241	High Similarity	NPC236132
0.9236	High Similarity	NPC234644
0.9236	High Similarity	NPC32694
0.9236	High Similarity	NPC474187
0.9231	High Similarity	NPC152904
0.9231	High Similarity	NPC204879
0.9231	High Similarity	NPC329091
0.9231	High Similarity	NPC235448
0.9226	High Similarity	NPC255106
0.9226	High Similarity	NPC49824
0.9226	High Similarity	NPC235165
0.9226	High Similarity	NPC133970
0.9226	High Similarity	NPC6633
0.9226	High Similarity	NPC138243
0.9226	High Similarity	NPC24640
0.9226	High Similarity	NPC472916
0.9226	High Similarity	NPC5322
0.9226	High Similarity	NPC471985
0.9226	High Similarity	NPC276444
0.9221	High Similarity	NPC75279
0.9221	High Similarity	NPC292214
0.9221	High Similarity	NPC88645
0.9221	High Similarity	NPC206238
0.9221	High Similarity	NPC271779
0.9221	High Similarity	NPC280530
0.9221	High Similarity	NPC167091
0.9221	High Similarity	NPC178964
0.9221	High Similarity	NPC276409
0.9221	High Similarity	NPC95842
0.9221	High Similarity	NPC250822
0.9216	High Similarity	NPC117579
0.9216	High Similarity	NPC208043
0.9216	High Similarity	NPC226973
0.9216	High Similarity	NPC251110
0.9211	High Similarity	NPC259713
0.9211	High Similarity	NPC294502
0.9211	High Similarity	NPC216318
0.9211	High Similarity	NPC296197
0.9211	High Similarity	NPC200221
0.9211	High Similarity	NPC17286
0.9193	High Similarity	NPC101107
0.9187	High Similarity	NPC218226
0.9187	High Similarity	NPC126204
0.9187	High Similarity	NPC476306
0.9182	High Similarity	NPC293319
0.9182	High Similarity	NPC234052
0.9182	High Similarity	NPC156432
0.9182	High Similarity	NPC326520
0.9177	High Similarity	NPC52204
0.9177	High Similarity	NPC261470
0.9177	High Similarity	NPC294965
0.9177	High Similarity	NPC472964
0.9172	High Similarity	NPC472902
0.9172	High Similarity	NPC118256
0.9172	High Similarity	NPC119224
0.9172	High Similarity	NPC474287
0.9172	High Similarity	NPC192686
0.9172	High Similarity	NPC36217

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 NPC474290 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	1017
0.2-0.3	1807
0.3-0.4	2672
0.4-0.5	1772
0.5-0.6	935
0.6-0.7	357
0.7-0.8	129
0.8-0.85	29
0.85-0.9	11
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9346	High Similarity	NPD2801	Approved
0.9032	High Similarity	NPD1934	Approved
0.8882	High Similarity	NPD1511	Approved
0.8854	High Similarity	NPD2393	Clinical (unspecified phase)
0.8766	High Similarity	NPD1512	Approved
0.8712	High Similarity	NPD6167	Clinical (unspecified phase)
0.8712	High Similarity	NPD6168	Clinical (unspecified phase)
0.8712	High Similarity	NPD6166	Phase 2
0.8625	High Similarity	NPD3882	Suspended
0.858	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD4338	Clinical (unspecified phase)
0.8554	High Similarity	NPD7054	Approved
0.8503	High Similarity	NPD7472	Approved
0.8503	High Similarity	NPD7074	Phase 3
0.85	High Similarity	NPD1465	Phase 2
0.8494	Intermediate Similarity	NPD3818	Discontinued
0.8447	Intermediate Similarity	NPD3817	Phase 2
0.8395	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6797	Phase 2
0.8333	Intermediate Similarity	NPD5844	Phase 1
0.8323	Intermediate Similarity	NPD3750	Approved
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD4380	Phase 2
0.8294	Intermediate Similarity	NPD7251	Discontinued
0.8246	Intermediate Similarity	NPD7808	Phase 3
0.8232	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD5402	Approved
0.816	Intermediate Similarity	NPD7819	Suspended
0.8129	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3749	Approved
0.8084	Intermediate Similarity	NPD6959	Discontinued
0.8077	Intermediate Similarity	NPD1549	Phase 2
0.8067	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3748	Approved
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7974	Intermediate Similarity	NPD943	Approved
0.7962	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD2796	Approved
0.7939	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD1247	Approved
0.7865	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1613	Approved
0.7857	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1240	Approved
0.7834	Intermediate Similarity	NPD2935	Discontinued
0.7826	Intermediate Similarity	NPD6799	Approved
0.7818	Intermediate Similarity	NPD7411	Suspended
0.7806	Intermediate Similarity	NPD447	Suspended
0.7791	Intermediate Similarity	NPD5403	Approved
0.7785	Intermediate Similarity	NPD2346	Discontinued
0.7778	Intermediate Similarity	NPD3926	Phase 2
0.7771	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7771	Intermediate Similarity	NPD6801	Discontinued
0.7758	Intermediate Similarity	NPD6599	Discontinued
0.7756	Intermediate Similarity	NPD1607	Approved
0.7751	Intermediate Similarity	NPD6234	Discontinued
0.7746	Intermediate Similarity	NPD3751	Discontinued
0.7738	Intermediate Similarity	NPD7768	Phase 2
0.7722	Intermediate Similarity	NPD6100	Approved
0.7722	Intermediate Similarity	NPD6099	Approved
0.7719	Intermediate Similarity	NPD3787	Discontinued
0.7697	Intermediate Similarity	NPD3226	Approved
0.7688	Intermediate Similarity	NPD2800	Approved
0.768	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5401	Approved
0.7669	Intermediate Similarity	NPD2534	Approved
0.7669	Intermediate Similarity	NPD2532	Approved
0.7669	Intermediate Similarity	NPD2533	Approved
0.7662	Intermediate Similarity	NPD3027	Phase 3
0.7644	Intermediate Similarity	NPD7228	Approved
0.7636	Intermediate Similarity	NPD1653	Approved
0.763	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD37	Approved
0.7558	Intermediate Similarity	NPD7199	Phase 2
0.7548	Intermediate Similarity	NPD4625	Phase 3
0.7547	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2799	Discontinued
0.7544	Intermediate Similarity	NPD919	Approved
0.7531	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD7390	Discontinued
0.7486	Intermediate Similarity	NPD8312	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.7471	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1933	Approved
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7455	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2344	Approved
0.7423	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6776	Approved
0.7394	Intermediate Similarity	NPD6779	Approved
0.7394	Intermediate Similarity	NPD6777	Approved
0.7394	Intermediate Similarity	NPD6780	Approved
0.7394	Intermediate Similarity	NPD6781	Approved
0.7394	Intermediate Similarity	NPD6778	Approved
0.7394	Intermediate Similarity	NPD6782	Approved
0.7389	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7685	Pre-registration
0.7368	Intermediate Similarity	NPD4288	Approved
0.7355	Intermediate Similarity	NPD2798	Approved
0.7353	Intermediate Similarity	NPD6844	Discontinued
0.7333	Intermediate Similarity	NPD7549	Discontinued
0.7317	Intermediate Similarity	NPD4628	Phase 3
0.7316	Intermediate Similarity	NPD6823	Phase 2
0.729	Intermediate Similarity	NPD1470	Approved
0.729	Intermediate Similarity	NPD1203	Approved
0.729	Intermediate Similarity	NPD2797	Approved
0.7289	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3764	Approved
0.7277	Intermediate Similarity	NPD7435	Discontinued
0.7273	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD4749	Approved
0.7273	Intermediate Similarity	NPD2309	Approved
0.7268	Intermediate Similarity	NPD8150	Discontinued
0.7262	Intermediate Similarity	NPD920	Approved
0.7256	Intermediate Similarity	NPD1243	Approved
0.7256	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1610	Phase 2
0.7255	Intermediate Similarity	NPD1201	Approved
0.7238	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4308	Phase 3
0.7216	Intermediate Similarity	NPD5711	Approved
0.7216	Intermediate Similarity	NPD5710	Approved
0.7197	Intermediate Similarity	NPD2861	Phase 2
0.7197	Intermediate Similarity	NPD9494	Approved
0.7194	Intermediate Similarity	NPD7783	Phase 2
0.7194	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4287	Approved
0.7188	Intermediate Similarity	NPD7697	Approved
0.7188	Intermediate Similarity	NPD7696	Phase 3
0.7188	Intermediate Similarity	NPD7698	Approved
0.7182	Intermediate Similarity	NPD7240	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)
0.7174	Intermediate Similarity	NPD8434	Phase 2
0.715	Intermediate Similarity	NPD7871	Phase 2
0.715	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7128	Intermediate Similarity	NPD7701	Phase 2
0.7128	Intermediate Similarity	NPD4363	Phase 3
0.7128	Intermediate Similarity	NPD6535	Approved
0.7128	Intermediate Similarity	NPD4360	Phase 2
0.7128	Intermediate Similarity	NPD6534	Approved
0.7127	Intermediate Similarity	NPD5953	Discontinued
0.7126	Intermediate Similarity	NPD3300	Phase 2
0.7111	Intermediate Similarity	NPD7286	Phase 2
0.7105	Intermediate Similarity	NPD1548	Phase 1
0.7101	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6651	Approved
0.7097	Intermediate Similarity	NPD9717	Approved
0.7092	Intermediate Similarity	NPD8151	Discontinued
0.7081	Intermediate Similarity	NPD4060	Phase 1
0.7079	Intermediate Similarity	NPD5242	Approved
0.7056	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7874	Approved
0.7044	Intermediate Similarity	NPD6832	Phase 2
0.7041	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2403	Approved
0.7037	Intermediate Similarity	NPD5124	Phase 1
0.7037	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7229	Phase 3
0.702	Intermediate Similarity	NPD7801	Approved
0.702	Intermediate Similarity	NPD6671	Approved
0.7019	Intermediate Similarity	NPD6233	Phase 2
0.7016	Intermediate Similarity	NPD7700	Phase 2
0.7016	Intermediate Similarity	NPD7699	Phase 2
0.7012	Intermediate Similarity	NPD7033	Discontinued
0.7006	Intermediate Similarity	NPD3225	Approved
0.7	Intermediate Similarity	NPD7095	Approved
0.6995	Remote Similarity	NPD2493	Approved
0.6995	Remote Similarity	NPD2494	Approved
0.6994	Remote Similarity	NPD7615	Clinical (unspecified phase)

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