NPASS Compound

Structure

CID83922 OpenBabel06191715422D 30 33 0 0 0 0 0 0 0 0999 V2000 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 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -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 5.1962 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 -0.8660 -1.5000 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 -0.0000 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 0.8660 -1.5000 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 4.3301 -1.5000 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 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 2.5981 -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 3.4641 -2.0000 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 6.0622 -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 6.9282 -2.0000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 28 1 0 0 0 0 6 7 1 0 0 0 0 6 12 2 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 24 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 13 17 1 0 0 0 0 13 20 2 0 0 0 0 14 22 2 0 0 0 0 14 23 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 30 1 0 0 0 0 18 19 2 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 22 29 1 0 0 0 0 23 28 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.16
Volume:	418.447
LogP:	6.071
LogD:	3.669
LogS:	-2.677
# Rotatable Bonds:	3
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	3.279
Fsp3:	0.292
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.816
MDCK Permeability:	1.6515479728695937e-05
Pgp-inhibitor:	0.929
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.195
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	86.37155151367188%
Volume Distribution (VD):	0.781
Pgp-substrate:	14.31423282623291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.564
CYP1A2-substrate:	0.647
CYP2C19-inhibitor:	0.819
CYP2C19-substrate:	0.14
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.63
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.387
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	2.036
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.284
Rat Oral Acute Toxicity:	0.892
Maximum Recommended Daily Dose:	0.796
Skin Sensitization:	0.759
Carcinogencity:	0.752
Eye Corrosion:	0.003
Eye Irritation:	0.101
Respiratory Toxicity:	0.857

Download Data

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

Natural Product: NPC83922

Natural Product ID:	NPC83922
*Common Name:**	Manglexanthone
IUPAC Name:	5,8-dihydroxy-9-methoxy-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
Synonyms:
Standard InCHIKey:	IGOVDGFRUNTYAS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H24O6/c1-12(2)6-7-14-22-15(10-16(25)23(14)28-5)21(27)19-18(29-22)11-17-13(20(19)26)8-9-24(3,4)30-17/h6,8-11,25-26H,7H2,1-5H3
SMILES:	COc1c(O)cc2c(c1CC=C(C)C)oc1c(c2=O)c(O)c2c(c1)OC(C=C2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2437088
PubChem CID:	10001484
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:0003518] 4-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
NPO22497	Picrasma javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26606140]
NPO21218	Salvia aegyptiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22497	Picrasma javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21652	Decarya madagascariensis	Species	Didiereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20963	Sarcopyramis bodinieri	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21218	Salvia aegyptiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22370	Baccharis calvescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20085	Solenopsis xyloni	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5221	Thamnolia subuliformis	Species	Icmadophilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3555	Cavernularia obesa	Species	Veretillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22435	Abies lasiocarpa	Species	Pinaceae	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	=	1900.0	nM	PMID[572746]

☑ 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 NPC83922 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	453
0.1-0.2	1809
0.2-0.3	4584
0.3-0.4	10999
0.4-0.5	6791
0.5-0.6	3629
0.6-0.7	5081
0.7-0.8	4803
0.8-0.85	2284
0.85-0.9	1348
0.9-0.95	802
0.95-1	114

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472448
0.9935	High Similarity	NPC29876
0.9935	High Similarity	NPC167678
0.9869	High Similarity	NPC476980
0.9869	High Similarity	NPC204290
0.9805	High Similarity	NPC259456
0.9804	High Similarity	NPC204879
0.9744	High Similarity	NPC275780
0.9744	High Similarity	NPC472450
0.9744	High Similarity	NPC239752
0.9742	High Similarity	NPC261470
0.9739	High Similarity	NPC262286
0.9739	High Similarity	NPC78225
0.9739	High Similarity	NPC36852
0.9739	High Similarity	NPC476981
0.9739	High Similarity	NPC474681
0.9739	High Similarity	NPC218313
0.9682	High Similarity	NPC39091
0.9679	High Similarity	NPC23298
0.9679	High Similarity	NPC189473
0.9679	High Similarity	NPC303460
0.9679	High Similarity	NPC306321
0.9677	High Similarity	NPC258331
0.9673	High Similarity	NPC68093
0.9673	High Similarity	NPC138243
0.9673	High Similarity	NPC5322
0.9673	High Similarity	NPC6633
0.9673	High Similarity	NPC133970
0.9673	High Similarity	NPC472455
0.9673	High Similarity	NPC191146
0.9618	High Similarity	NPC50960
0.9615	High Similarity	NPC229632
0.9615	High Similarity	NPC474162
0.9615	High Similarity	NPC474150
0.9615	High Similarity	NPC329760
0.9613	High Similarity	NPC119209
0.9613	High Similarity	NPC118256
0.9613	High Similarity	NPC192686
0.961	High Similarity	NPC52889
0.9608	High Similarity	NPC200246
0.9608	High Similarity	NPC230149
0.9608	High Similarity	NPC256612
0.9608	High Similarity	NPC57674
0.9608	High Similarity	NPC234255
0.9608	High Similarity	NPC20830
0.9608	High Similarity	NPC168247
0.9608	High Similarity	NPC472280
0.9608	High Similarity	NPC152951
0.9608	High Similarity	NPC117992
0.9608	High Similarity	NPC256925
0.9608	High Similarity	NPC113906
0.9557	High Similarity	NPC37870
0.9557	High Similarity	NPC472449
0.9554	High Similarity	NPC236521
0.9554	High Similarity	NPC152659
0.9554	High Similarity	NPC248638
0.9551	High Similarity	NPC234644
0.9551	High Similarity	NPC474038
0.9551	High Similarity	NPC266314
0.9551	High Similarity	NPC134783
0.9551	High Similarity	NPC57715
0.9551	High Similarity	NPC61010
0.9548	High Similarity	NPC74178
0.9548	High Similarity	NPC184755
0.9548	High Similarity	NPC250214
0.9548	High Similarity	NPC95936
0.9545	High Similarity	NPC276444
0.9545	High Similarity	NPC471985
0.9545	High Similarity	NPC470600
0.9545	High Similarity	NPC472916
0.9542	High Similarity	NPC176775
0.9542	High Similarity	NPC22519
0.9542	High Similarity	NPC183878
0.9542	High Similarity	NPC227337
0.9542	High Similarity	NPC292214
0.9542	High Similarity	NPC69394
0.9542	High Similarity	NPC33051
0.9542	High Similarity	NPC145379
0.9542	High Similarity	NPC167091
0.9542	High Similarity	NPC274327
0.9542	High Similarity	NPC160951
0.9542	High Similarity	NPC231018
0.9542	High Similarity	NPC47781
0.9542	High Similarity	NPC88645
0.9542	High Similarity	NPC206238
0.9542	High Similarity	NPC271779
0.9542	High Similarity	NPC70433
0.9542	High Similarity	NPC273462
0.9542	High Similarity	NPC255350
0.9542	High Similarity	NPC49402
0.9503	High Similarity	NPC310794
0.95	High Similarity	NPC472276
0.949	High Similarity	NPC474034
0.949	High Similarity	NPC81679
0.949	High Similarity	NPC474033
0.949	High Similarity	NPC25152
0.9487	High Similarity	NPC56085
0.9487	High Similarity	NPC14353
0.9487	High Similarity	NPC471973
0.9487	High Similarity	NPC475784
0.9487	High Similarity	NPC139036
0.9487	High Similarity	NPC246478
0.9487	High Similarity	NPC228785
0.9487	High Similarity	NPC188433
0.9484	High Similarity	NPC472914
0.9484	High Similarity	NPC162869
0.9484	High Similarity	NPC472911
0.9484	High Similarity	NPC284820
0.9484	High Similarity	NPC218871
0.9484	High Similarity	NPC223787
0.9484	High Similarity	NPC27337
0.9484	High Similarity	NPC210084
0.9484	High Similarity	NPC99597
0.9484	High Similarity	NPC245758
0.9484	High Similarity	NPC474208
0.9484	High Similarity	NPC476630
0.9484	High Similarity	NPC475267
0.9484	High Similarity	NPC474836
0.9484	High Similarity	NPC222814
0.9484	High Similarity	NPC156057
0.9484	High Similarity	NPC96167
0.9484	High Similarity	NPC472910
0.9484	High Similarity	NPC291508
0.9484	High Similarity	NPC472913
0.9484	High Similarity	NPC48208
0.9484	High Similarity	NPC473272
0.9481	High Similarity	NPC4455
0.9481	High Similarity	NPC146165
0.9481	High Similarity	NPC2928
0.9481	High Similarity	NPC92659
0.9481	High Similarity	NPC208197
0.9481	High Similarity	NPC213622
0.9481	High Similarity	NPC183597
0.9481	High Similarity	NPC196439
0.9481	High Similarity	NPC2476
0.9481	High Similarity	NPC138360
0.9481	High Similarity	NPC128863
0.9481	High Similarity	NPC280339
0.9481	High Similarity	NPC39184
0.9481	High Similarity	NPC50715
0.9481	High Similarity	NPC227325
0.9481	High Similarity	NPC163780
0.9481	High Similarity	NPC134287
0.9481	High Similarity	NPC167815
0.9481	High Similarity	NPC130589
0.9481	High Similarity	NPC201136
0.9477	High Similarity	NPC120163
0.9477	High Similarity	NPC83508
0.9477	High Similarity	NPC222830
0.9477	High Similarity	NPC275836
0.9477	High Similarity	NPC101996
0.9477	High Similarity	NPC301323
0.9477	High Similarity	NPC471982
0.9477	High Similarity	NPC198826
0.9477	High Similarity	NPC293183
0.9477	High Similarity	NPC162313
0.9477	High Similarity	NPC39732
0.9477	High Similarity	NPC212678
0.9477	High Similarity	NPC57030
0.9477	High Similarity	NPC39007
0.9477	High Similarity	NPC131624
0.9477	High Similarity	NPC120537
0.9477	High Similarity	NPC25270
0.9477	High Similarity	NPC239128
0.9477	High Similarity	NPC156222
0.9477	High Similarity	NPC256283
0.9477	High Similarity	NPC187498
0.9477	High Similarity	NPC166201
0.9477	High Similarity	NPC237994
0.9477	High Similarity	NPC71334
0.9477	High Similarity	NPC161277
0.9477	High Similarity	NPC180234
0.9477	High Similarity	NPC199100
0.9477	High Similarity	NPC60972
0.9477	High Similarity	NPC188203
0.9477	High Similarity	NPC100887
0.9477	High Similarity	NPC275722
0.9477	High Similarity	NPC241498
0.9437	High Similarity	NPC288813
0.9434	High Similarity	NPC120593
0.943	High Similarity	NPC220313
0.943	High Similarity	NPC186686
0.943	High Similarity	NPC207690
0.943	High Similarity	NPC41301
0.943	High Similarity	NPC124038
0.943	High Similarity	NPC472625
0.9427	High Similarity	NPC40491
0.9427	High Similarity	NPC471210
0.9427	High Similarity	NPC26326
0.9427	High Similarity	NPC40037
0.9427	High Similarity	NPC472275
0.9427	High Similarity	NPC198829
0.9427	High Similarity	NPC472632
0.9427	High Similarity	NPC278052
0.9423	High Similarity	NPC476242
0.9423	High Similarity	NPC172770
0.9423	High Similarity	NPC152904
0.9423	High Similarity	NPC474290
0.9423	High Similarity	NPC185258
0.9423	High Similarity	NPC100123

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 NPC83922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	970
0.2-0.3	1800
0.3-0.4	2694
0.4-0.5	1773
0.5-0.6	959
0.6-0.7	374
0.7-0.8	121
0.8-0.85	36
0.85-0.9	15
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9542	High Similarity	NPD2801	Approved
0.929	High Similarity	NPD2393	Clinical (unspecified phase)
0.9226	High Similarity	NPD1934	Approved
0.9	High Similarity	NPD5494	Approved
0.8954	High Similarity	NPD1511	Approved
0.8931	High Similarity	NPD3882	Suspended
0.8896	High Similarity	NPD6167	Clinical (unspecified phase)
0.8896	High Similarity	NPD6166	Phase 2
0.8896	High Similarity	NPD6168	Clinical (unspecified phase)
0.8854	High Similarity	NPD4380	Phase 2
0.8839	High Similarity	NPD1512	Approved
0.8788	High Similarity	NPD3818	Discontinued
0.8774	High Similarity	NPD4378	Clinical (unspecified phase)
0.875	High Similarity	NPD4338	Clinical (unspecified phase)
0.8735	High Similarity	NPD7054	Approved
0.8696	High Similarity	NPD4868	Clinical (unspecified phase)
0.8683	High Similarity	NPD7074	Phase 3
0.8683	High Similarity	NPD7472	Approved
0.8654	High Similarity	NPD7410	Clinical (unspecified phase)
0.8634	High Similarity	NPD3817	Phase 2
0.8528	High Similarity	NPD4381	Clinical (unspecified phase)
0.8528	High Similarity	NPD7075	Discontinued
0.8521	High Similarity	NPD6797	Phase 2
0.8512	High Similarity	NPD5844	Phase 1
0.8471	Intermediate Similarity	NPD7251	Discontinued
0.8457	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD6232	Discontinued
0.8421	Intermediate Similarity	NPD7808	Phase 3
0.8393	Intermediate Similarity	NPD7473	Discontinued
0.8387	Intermediate Similarity	NPD1549	Phase 2
0.8373	Intermediate Similarity	NPD1247	Approved
0.8344	Intermediate Similarity	NPD7819	Suspended
0.8344	Intermediate Similarity	NPD1465	Phase 2
0.8333	Intermediate Similarity	NPD7411	Suspended
0.8323	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1510	Phase 2
0.8294	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5402	Approved
0.8293	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6801	Discontinued
0.8258	Intermediate Similarity	NPD2796	Approved
0.8198	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1240	Approved
0.817	Intermediate Similarity	NPD943	Approved
0.8155	Intermediate Similarity	NPD6959	Discontinued
0.8141	Intermediate Similarity	NPD2935	Discontinued
0.8125	Intermediate Similarity	NPD6799	Approved
0.8065	Intermediate Similarity	NPD1607	Approved
0.8046	Intermediate Similarity	NPD6559	Discontinued
0.8036	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD3749	Approved
0.7953	Intermediate Similarity	NPD3926	Phase 2
0.7939	Intermediate Similarity	NPD6599	Discontinued
0.7937	Intermediate Similarity	NPD3750	Approved
0.7933	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7768	Phase 2
0.7908	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2800	Approved
0.7866	Intermediate Similarity	NPD5403	Approved
0.7845	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1613	Approved
0.7821	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD447	Suspended
0.7771	Intermediate Similarity	NPD230	Phase 1
0.7765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD920	Approved
0.7758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD5401	Approved
0.7744	Intermediate Similarity	NPD2533	Approved
0.7744	Intermediate Similarity	NPD2532	Approved
0.7744	Intermediate Similarity	NPD2534	Approved
0.7742	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD3751	Discontinued
0.7711	Intermediate Similarity	NPD1653	Approved
0.7692	Intermediate Similarity	NPD2313	Discontinued
0.7665	Intermediate Similarity	NPD3226	Approved
0.7654	Intermediate Similarity	NPD1243	Approved
0.764	Intermediate Similarity	NPD2346	Discontinued
0.7636	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3027	Phase 3
0.7625	Intermediate Similarity	NPD2799	Discontinued
0.7625	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3748	Approved
0.7625	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3787	Discontinued
0.7584	Intermediate Similarity	NPD5953	Discontinued
0.7578	Intermediate Similarity	NPD1551	Phase 2
0.7578	Intermediate Similarity	NPD6099	Approved
0.7578	Intermediate Similarity	NPD6100	Approved
0.7571	Intermediate Similarity	NPD7286	Phase 2
0.7561	Intermediate Similarity	NPD6190	Approved
0.7553	Intermediate Similarity	NPD6777	Approved
0.7553	Intermediate Similarity	NPD6776	Approved
0.7553	Intermediate Similarity	NPD6780	Approved
0.7553	Intermediate Similarity	NPD6778	Approved
0.7553	Intermediate Similarity	NPD6779	Approved
0.7553	Intermediate Similarity	NPD6782	Approved
0.7553	Intermediate Similarity	NPD6781	Approved
0.7547	Intermediate Similarity	NPD1933	Approved
0.7542	Intermediate Similarity	NPD7685	Pre-registration
0.7531	Intermediate Similarity	NPD2344	Approved
0.7515	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7390	Discontinued
0.7468	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8313	Approved
0.7459	Intermediate Similarity	NPD8312	Approved
0.7435	Intermediate Similarity	NPD7435	Discontinued
0.7432	Intermediate Similarity	NPD8150	Discontinued
0.7429	Intermediate Similarity	NPD7199	Phase 2
0.7427	Intermediate Similarity	NPD6844	Discontinued
0.7416	Intermediate Similarity	NPD7228	Approved
0.7409	Intermediate Similarity	NPD7584	Approved
0.7394	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD4360	Phase 2
0.738	Intermediate Similarity	NPD4363	Phase 3
0.7349	Intermediate Similarity	NPD2309	Approved
0.7345	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7697	Approved
0.7344	Intermediate Similarity	NPD7698	Approved
0.7344	Intermediate Similarity	NPD7696	Phase 3
0.7342	Intermediate Similarity	NPD4908	Phase 1
0.7337	Intermediate Similarity	NPD8434	Phase 2
0.7326	Intermediate Similarity	NPD37	Approved
0.7321	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7549	Discontinued
0.7306	Intermediate Similarity	NPD7871	Phase 2
0.7306	Intermediate Similarity	NPD7870	Phase 2
0.7299	Intermediate Similarity	NPD4965	Approved
0.7299	Intermediate Similarity	NPD4966	Approved
0.7299	Intermediate Similarity	NPD4967	Phase 2
0.7296	Intermediate Similarity	NPD4625	Phase 3
0.7292	Intermediate Similarity	NPD6823	Phase 2
0.7288	Intermediate Similarity	NPD5710	Approved
0.7288	Intermediate Similarity	NPD5711	Approved
0.7287	Intermediate Similarity	NPD6535	Approved
0.7287	Intermediate Similarity	NPD6534	Approved
0.7282	Intermediate Similarity	NPD7701	Phase 2
0.7261	Intermediate Similarity	NPD1203	Approved
0.7259	Intermediate Similarity	NPD7783	Phase 2
0.7259	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD5242	Approved
0.7245	Intermediate Similarity	NPD8151	Discontinued
0.7226	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5124	Phase 1
0.7215	Intermediate Similarity	NPD2798	Approved
0.7208	Intermediate Similarity	NPD7874	Approved
0.7208	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7033	Discontinued
0.7195	Intermediate Similarity	NPD4308	Phase 3
0.7179	Intermediate Similarity	NPD9269	Phase 2
0.7173	Intermediate Similarity	NPD7700	Phase 2
0.7173	Intermediate Similarity	NPD7699	Phase 2
0.7172	Intermediate Similarity	NPD7801	Approved
0.7169	Intermediate Similarity	NPD2424	Discontinued
0.7168	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7458	Discontinued
0.7151	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD3268	Approved
0.7125	Intermediate Similarity	NPD6832	Phase 2
0.7118	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1610	Phase 2
0.7111	Intermediate Similarity	NPD2403	Approved
0.7095	Intermediate Similarity	NPD7229	Phase 3
0.7094	Intermediate Similarity	NPD2899	Discontinued
0.7078	Intermediate Similarity	NPD1548	Phase 1
0.7074	Intermediate Similarity	NPD4287	Approved
0.707	Intermediate Similarity	NPD9717	Approved
0.7069	Intermediate Similarity	NPD6386	Approved
0.7069	Intermediate Similarity	NPD6385	Approved
0.7068	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4361	Phase 2
0.7063	Intermediate Similarity	NPD2861	Phase 2
0.7059	Intermediate Similarity	NPD4357	Discontinued
0.7048	Intermediate Similarity	NPD5406	Approved
0.7048	Intermediate Similarity	NPD5404	Approved
0.7048	Intermediate Similarity	NPD5405	Approved
0.7048	Intermediate Similarity	NPD5408	Approved
0.7045	Intermediate Similarity	NPD4288	Approved
0.7044	Intermediate Similarity	NPD1470	Approved
0.7044	Intermediate Similarity	NPD2797	Approved
0.7025	Intermediate Similarity	NPD4749	Approved
0.7024	Intermediate Similarity	NPD7907	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