NPASS Compound

Structure

CID166201 OpenBabel06191715542D 29 32 0 0 0 0 0 0 0 0999 V2000 -1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 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 0.8660 -3.5000 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 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 6.0622 -1.5000 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 4.3301 -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 6.0622 -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 3.4641 -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 4.3301 -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 5.1962 -0.0000 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 -0.8660 -0.5000 0.0000 C 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 1.7321 -3.0000 0.0000 O 0 0 0 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 1.0000 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 22 1 0 0 0 0 2 22 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 13 1 0 0 0 0 9 10 2 0 0 0 0 9 12 1 0 0 0 0 10 22 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 15 23 2 0 0 0 0 16 25 1 0 0 0 0 17 19 1 0 0 0 0 17 28 1 0 0 0 0 18 21 2 0 0 0 0 18 29 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.14
Volume:	395.282
LogP:	4.012
LogD:	3.326
LogS:	-4.538
# Rotatable Bonds:	4
TPSA:	76.36
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	2.996
Fsp3:	0.318
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:	-4.561
MDCK Permeability:	3.046514575544279e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	74.86945343017578%
Volume Distribution (VD):	0.936
Pgp-substrate:	26.797550201416016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.24
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.62
CYP2C19-substrate:	0.886
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.63
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.835

ADMET: Excretion

Clearance (CL):	2.458
Half-life (T1/2):	0.166

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.647
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.251
Rat Oral Acute Toxicity:	0.988
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.376
Carcinogencity:	0.662
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.672

Download Data

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

Natural Product: NPC166201

Natural Product ID:	NPC166201
*Common Name:**	Dulxanthone E
IUPAC Name:	5,9,10,12-tetramethoxy-2,2-dimethylpyrano[3,2-b]xanthen-6-one
Synonyms:
Standard InCHIKey:	DLIXREHRECIYQJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H22O7/c1-22(2)10-9-12-16(25-4)14-15(23)11-7-8-13(24-3)19(26-5)17(11)28-20(14)21(27-6)18(12)29-22/h7-10H,1-6H3
SMILES:	CC1(C)C=Cc2c(c3c(=O)c4ccc(c(c4oc3c(c2O1)OC)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2437087
PubChem CID:	11795135
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
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22337	Garcinia dulcis	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
NPT137	Cell Line	L1210	Mus musculus	IC50	=	4.23	ug.mL-1	PMID[558311]

☑ 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 NPC166201 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	553
0.1-0.2	2040
0.2-0.3	5420
0.3-0.4	11685
0.4-0.5	5634
0.5-0.6	4166
0.6-0.7	5805
0.7-0.8	4483
0.8-0.85	1857
0.85-0.9	786
0.9-0.95	253
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9796	High Similarity	NPC128961
0.9796	High Similarity	NPC472408
0.9664	High Similarity	NPC180340
0.9595	High Similarity	NPC40033
0.9589	High Similarity	NPC63256
0.9589	High Similarity	NPC10304
0.9539	High Similarity	NPC165549
0.9521	High Similarity	NPC205522
0.9477	High Similarity	NPC83922
0.9477	High Similarity	NPC472448
0.947	High Similarity	NPC476981
0.947	High Similarity	NPC19097
0.9459	High Similarity	NPC189270
0.9459	High Similarity	NPC5840
0.9452	High Similarity	NPC110639
0.9452	High Similarity	NPC14958
0.9452	High Similarity	NPC231013
0.9452	High Similarity	NPC40818
0.9452	High Similarity	NPC106461
0.9452	High Similarity	NPC215932
0.9412	High Similarity	NPC29876
0.9412	High Similarity	NPC167678
0.9392	High Similarity	NPC238366
0.9388	High Similarity	NPC85233
0.9384	High Similarity	NPC136278
0.9384	High Similarity	NPC165512
0.9351	High Similarity	NPC261470
0.9351	High Similarity	NPC18284
0.9351	High Similarity	NPC273021
0.9351	High Similarity	NPC229632
0.9346	High Similarity	NPC204290
0.9346	High Similarity	NPC298093
0.9346	High Similarity	NPC476980
0.9324	High Similarity	NPC476342
0.932	High Similarity	NPC302408
0.932	High Similarity	NPC283002
0.932	High Similarity	NPC216314
0.932	High Similarity	NPC120924
0.932	High Similarity	NPC195919
0.9315	High Similarity	NPC182842
0.9315	High Similarity	NPC23955
0.9315	High Similarity	NPC113089
0.929	High Similarity	NPC306321
0.929	High Similarity	NPC303460
0.9286	High Similarity	NPC40037
0.9286	High Similarity	NPC259456
0.9281	High Similarity	NPC204879
0.9276	High Similarity	NPC248299
0.9272	High Similarity	NPC186507
0.9267	High Similarity	NPC198615
0.9262	High Similarity	NPC69752
0.9252	High Similarity	NPC471590
0.9247	High Similarity	NPC70853
0.9247	High Similarity	NPC9966
0.9236	High Similarity	NPC8965
0.9231	High Similarity	NPC275780
0.9231	High Similarity	NPC472450
0.9231	High Similarity	NPC239752
0.9231	High Similarity	NPC50960
0.9216	High Similarity	NPC262286
0.9216	High Similarity	NPC36852
0.9216	High Similarity	NPC473272
0.9216	High Similarity	NPC284820
0.9216	High Similarity	NPC78225
0.9216	High Similarity	NPC218313
0.9216	High Similarity	NPC474681
0.9211	High Similarity	NPC256925
0.9211	High Similarity	NPC200246
0.92	High Similarity	NPC29056
0.92	High Similarity	NPC259058
0.92	High Similarity	NPC201547
0.9184	High Similarity	NPC293201
0.9178	High Similarity	NPC124467
0.9178	High Similarity	NPC214919
0.9178	High Similarity	NPC29536
0.9172	High Similarity	NPC173292
0.9172	High Similarity	NPC39091
0.9172	High Similarity	NPC120593
0.9167	High Similarity	NPC189473
0.9167	High Similarity	NPC23298
0.9161	High Similarity	NPC34376
0.9161	High Similarity	NPC258331
0.9161	High Similarity	NPC57715
0.915	High Similarity	NPC133970
0.915	High Similarity	NPC6633
0.915	High Similarity	NPC5322
0.915	High Similarity	NPC68093
0.915	High Similarity	NPC191146
0.915	High Similarity	NPC303255
0.915	High Similarity	NPC138243
0.915	High Similarity	NPC472455
0.915	High Similarity	NPC470600
0.9145	High Similarity	NPC280937
0.9145	High Similarity	NPC472915
0.9139	High Similarity	NPC208043
0.9139	High Similarity	NPC226973
0.9139	High Similarity	NPC149614
0.9139	High Similarity	NPC117579
0.9139	High Similarity	NPC308451
0.9139	High Similarity	NPC474663
0.9133	High Similarity	NPC181250
0.9128	High Similarity	NPC470511
0.9128	High Similarity	NPC299923
0.9119	High Similarity	NPC472276
0.9116	High Similarity	NPC476054
0.911	High Similarity	NPC58229
0.9103	High Similarity	NPC329760
0.9103	High Similarity	NPC52204
0.9103	High Similarity	NPC474162
0.9103	High Similarity	NPC474150
0.9097	High Similarity	NPC118256
0.9097	High Similarity	NPC475784
0.9097	High Similarity	NPC119209
0.9097	High Similarity	NPC192686
0.9097	High Similarity	NPC188433
0.9091	High Similarity	NPC165977
0.9091	High Similarity	NPC217677
0.9091	High Similarity	NPC78071
0.9091	High Similarity	NPC310206
0.9091	High Similarity	NPC181960
0.9091	High Similarity	NPC52889
0.9085	High Similarity	NPC20830
0.9085	High Similarity	NPC168247
0.9085	High Similarity	NPC256612
0.9085	High Similarity	NPC117992
0.9085	High Similarity	NPC234255
0.9085	High Similarity	NPC230149
0.9085	High Similarity	NPC472280
0.9085	High Similarity	NPC472909
0.9085	High Similarity	NPC152951
0.9085	High Similarity	NPC113906
0.9085	High Similarity	NPC57674
0.9085	High Similarity	NPC37392
0.9079	High Similarity	NPC39007
0.9079	High Similarity	NPC161277
0.9079	High Similarity	NPC134677
0.9073	High Similarity	NPC306821
0.9073	High Similarity	NPC120105
0.9073	High Similarity	NPC179183
0.9073	High Similarity	NPC101957
0.9067	High Similarity	NPC183236
0.906	High Similarity	NPC310259
0.9057	High Similarity	NPC177480
0.9057	High Similarity	NPC242395
0.9057	High Similarity	NPC152477
0.9051	High Similarity	NPC128293
0.9051	High Similarity	NPC472449
0.9051	High Similarity	NPC37870
0.9048	High Similarity	NPC185607
0.9045	High Similarity	NPC236521
0.9045	High Similarity	NPC65846
0.9045	High Similarity	NPC152659
0.9045	High Similarity	NPC248638
0.9038	High Similarity	NPC474187
0.9038	High Similarity	NPC134783
0.9038	High Similarity	NPC474038
0.9038	High Similarity	NPC266314
0.9038	High Similarity	NPC234644
0.9038	High Similarity	NPC61010
0.9032	High Similarity	NPC152904
0.9032	High Similarity	NPC250214
0.9032	High Similarity	NPC113055
0.9032	High Similarity	NPC95936
0.9032	High Similarity	NPC74178
0.9032	High Similarity	NPC184755
0.9032	High Similarity	NPC187792
0.9026	High Similarity	NPC471985
0.9026	High Similarity	NPC472916
0.9026	High Similarity	NPC276444
0.902	High Similarity	NPC183878
0.902	High Similarity	NPC86485
0.902	High Similarity	NPC167091
0.902	High Similarity	NPC47781
0.902	High Similarity	NPC160951
0.902	High Similarity	NPC22519
0.902	High Similarity	NPC231018
0.902	High Similarity	NPC206238
0.902	High Similarity	NPC33051
0.902	High Similarity	NPC49402
0.902	High Similarity	NPC292214
0.902	High Similarity	NPC273462
0.902	High Similarity	NPC255350
0.902	High Similarity	NPC244371
0.902	High Similarity	NPC145379
0.902	High Similarity	NPC271779
0.902	High Similarity	NPC274327
0.902	High Similarity	NPC88645
0.902	High Similarity	NPC69394
0.902	High Similarity	NPC227337
0.902	High Similarity	NPC176775
0.902	High Similarity	NPC70433
0.9013	High Similarity	NPC262623
0.9013	High Similarity	NPC171010
0.9007	High Similarity	NPC328119
0.9007	High Similarity	NPC474648
0.9007	High Similarity	NPC266499
0.9006	High Similarity	NPC310794
0.9	High Similarity	NPC74559
0.9	High Similarity	NPC103307
0.8987	High Similarity	NPC475369

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 NPC166201 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	463
0.1-0.2	1025
0.2-0.3	1936
0.3-0.4	2714
0.4-0.5	1699
0.5-0.6	864
0.6-0.7	309
0.7-0.8	104
0.8-0.85	26
0.85-0.9	7
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9346	High Similarity	NPD5494	Approved
0.902	High Similarity	NPD2801	Approved
0.8774	High Similarity	NPD2393	Clinical (unspecified phase)
0.871	High Similarity	NPD1934	Approved
0.8679	High Similarity	NPD1247	Approved
0.8599	High Similarity	NPD3817	Phase 2
0.8581	High Similarity	NPD2796	Approved
0.8497	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4380	Phase 2
0.8431	Intermediate Similarity	NPD1511	Approved
0.8428	Intermediate Similarity	NPD3882	Suspended
0.8405	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD6166	Phase 2
0.8377	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD5844	Phase 1
0.8323	Intermediate Similarity	NPD919	Approved
0.8323	Intermediate Similarity	NPD1512	Approved
0.8303	Intermediate Similarity	NPD3818	Discontinued
0.8302	Intermediate Similarity	NPD7819	Suspended
0.8302	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7054	Approved
0.8239	Intermediate Similarity	NPD6801	Discontinued
0.8232	Intermediate Similarity	NPD3926	Phase 2
0.8204	Intermediate Similarity	NPD7074	Phase 3
0.8204	Intermediate Similarity	NPD7472	Approved
0.8199	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7411	Suspended
0.8171	Intermediate Similarity	NPD6232	Discontinued
0.8153	Intermediate Similarity	NPD920	Approved
0.8148	Intermediate Similarity	NPD7075	Discontinued
0.8148	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5402	Approved
0.8133	Intermediate Similarity	NPD7473	Discontinued
0.8105	Intermediate Similarity	NPD1549	Phase 2
0.8077	Intermediate Similarity	NPD6799	Approved
0.8059	Intermediate Similarity	NPD7808	Phase 3
0.8047	Intermediate Similarity	NPD6797	Phase 2
0.8039	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1510	Phase 2
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7963	Intermediate Similarity	NPD1465	Phase 2
0.7935	Intermediate Similarity	NPD1243	Approved
0.7929	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD3748	Approved
0.7888	Intermediate Similarity	NPD6599	Discontinued
0.7881	Intermediate Similarity	NPD1240	Approved
0.7857	Intermediate Similarity	NPD2935	Discontinued
0.7829	Intermediate Similarity	NPD1933	Approved
0.7785	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1607	Approved
0.7751	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3749	Approved
0.7707	Intermediate Similarity	NPD2800	Approved
0.7702	Intermediate Similarity	NPD5403	Approved
0.7688	Intermediate Similarity	NPD5401	Approved
0.7688	Intermediate Similarity	NPD6559	Discontinued
0.7658	Intermediate Similarity	NPD3750	Approved
0.7651	Intermediate Similarity	NPD7768	Phase 2
0.7647	Intermediate Similarity	NPD943	Approved
0.7632	Intermediate Similarity	NPD2313	Discontinued
0.7597	Intermediate Similarity	NPD447	Suspended
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2346	Discontinued
0.7564	Intermediate Similarity	NPD2799	Discontinued
0.7532	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5242	Approved
0.7469	Intermediate Similarity	NPD2532	Approved
0.7469	Intermediate Similarity	NPD2534	Approved
0.7469	Intermediate Similarity	NPD2533	Approved
0.7457	Intermediate Similarity	NPD3751	Discontinued
0.7442	Intermediate Similarity	NPD2403	Approved
0.7427	Intermediate Similarity	NPD3787	Discontinued
0.7414	Intermediate Similarity	NPD7286	Phase 2
0.7403	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6832	Phase 2
0.7381	Intermediate Similarity	NPD5353	Approved
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6844	Discontinued
0.7342	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5953	Discontinued
0.7325	Intermediate Similarity	NPD6651	Approved
0.732	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1613	Approved
0.7305	Intermediate Similarity	NPD6386	Approved
0.7305	Intermediate Similarity	NPD6385	Approved
0.7301	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6100	Approved
0.7296	Intermediate Similarity	NPD6099	Approved
0.7296	Intermediate Similarity	NPD1551	Phase 2
0.7279	Intermediate Similarity	NPD5536	Phase 2
0.7267	Intermediate Similarity	NPD7199	Phase 2
0.7261	Intermediate Similarity	NPD230	Phase 1
0.7255	Intermediate Similarity	NPD2798	Approved
0.725	Intermediate Similarity	NPD2344	Approved
0.7247	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6585	Discontinued
0.7229	Intermediate Similarity	NPD1653	Approved
0.7222	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4628	Phase 3
0.7219	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6776	Approved
0.7219	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD6778	Approved
0.7219	Intermediate Similarity	NPD6779	Approved
0.7219	Intermediate Similarity	NPD6782	Approved
0.7202	Intermediate Similarity	NPD5889	Approved
0.7202	Intermediate Similarity	NPD5890	Approved
0.7197	Intermediate Similarity	NPD4307	Phase 2
0.7195	Intermediate Similarity	NPD7390	Discontinued
0.7184	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2654	Approved
0.716	Intermediate Similarity	NPD37	Approved
0.7151	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4966	Approved
0.7135	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4965	Approved
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7135	Intermediate Similarity	NPD4967	Phase 2
0.7125	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3027	Phase 3
0.7111	Intermediate Similarity	NPD8312	Approved
0.7111	Intermediate Similarity	NPD8313	Approved
0.7105	Intermediate Similarity	NPD3972	Approved
0.7105	Intermediate Similarity	NPD7696	Phase 3
0.7105	Intermediate Similarity	NPD7698	Approved
0.7105	Intermediate Similarity	NPD7697	Approved
0.7105	Intermediate Similarity	NPD7435	Discontinued
0.7097	Intermediate Similarity	NPD3018	Phase 2
0.7095	Intermediate Similarity	NPD7685	Pre-registration
0.7088	Intermediate Similarity	NPD8434	Phase 2
0.7088	Intermediate Similarity	NPD8150	Discontinued
0.7083	Intermediate Similarity	NPD7584	Approved
0.7078	Intermediate Similarity	NPD3266	Approved
0.7078	Intermediate Similarity	NPD3267	Approved
0.7074	Intermediate Similarity	NPD8285	Discontinued
0.7073	Intermediate Similarity	NPD2309	Approved
0.7073	Intermediate Similarity	NPD6190	Approved
0.7068	Intermediate Similarity	NPD7871	Phase 2
0.7068	Intermediate Similarity	NPD7870	Phase 2
0.7059	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6234	Discontinued
0.7051	Intermediate Similarity	NPD4908	Phase 1
0.7044	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5124	Phase 1
0.7029	Intermediate Similarity	NPD7229	Phase 3
0.7029	Intermediate Similarity	NPD5710	Approved
0.7029	Intermediate Similarity	NPD5711	Approved
0.702	Intermediate Similarity	NPD17	Approved
0.7019	Intermediate Similarity	NPD4308	Phase 3
0.7019	Intermediate Similarity	NPD7033	Discontinued
0.7006	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4625	Phase 3
0.7	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2424	Discontinued
0.6993	Remote Similarity	NPD2981	Phase 2
0.6987	Remote Similarity	NPD9494	Approved
0.6982	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7458	Discontinued
0.6977	Remote Similarity	NPD5978	Approved
0.6977	Remote Similarity	NPD4288	Approved
0.6977	Remote Similarity	NPD5977	Approved
0.697	Remote Similarity	NPD3887	Approved
0.6968	Remote Similarity	NPD1203	Approved
0.6966	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7228	Approved
0.6963	Remote Similarity	NPD6823	Phase 2
0.6962	Remote Similarity	NPD1296	Phase 2
0.6962	Remote Similarity	NPD3268	Approved
0.6959	Remote Similarity	NPD7701	Phase 2
0.6952	Remote Similarity	NPD6535	Approved
0.6952	Remote Similarity	NPD6534	Approved
0.6948	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2983	Phase 2
0.6948	Remote Similarity	NPD2982	Phase 2
0.6946	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7783	Phase 2
0.6933	Remote Similarity	NPD2355	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