NPASS Compound

Structure

NPC470600 OpenBabel07101718312D 24 27 0 0 0 0 0 0 0 0999 V2000 -0.2588 -1.9659 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 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 1.7321 -1.0000 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 0.8660 1.5000 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 4.3301 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 1.7321 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 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 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 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 3.4641 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 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 18 1 0 0 0 0 2 18 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 18 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 17 2 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 14 21 2 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	319.945
LogP:	3.836
LogD:	2.806
LogS:	-3.99
# Rotatable Bonds:	0
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	2.911
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936
MDCK Permeability:	1.694617276370991e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.05
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	95.41527557373047%
Volume Distribution (VD):	0.589
Pgp-substrate:	8.016416549682617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.898
CYP1A2-substrate:	0.744
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.661
CYP2C9-substrate:	0.783
CYP2D6-inhibitor:	0.128
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	4.99
Half-life (T1/2):	0.707

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.774
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.71
Rat Oral Acute Toxicity:	0.345
Maximum Recommended Daily Dose:	0.3
Skin Sensitization:	0.87
Carcinogencity:	0.746
Eye Corrosion:	0.003
Eye Irritation:	0.602
Respiratory Toxicity:	0.232

Download Data

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

Natural Product: NPC470600

Natural Product ID:	NPC470600
*Common Name:**	Isojacareubin
IUPAC Name:	6,10,11-trihydroxy-3,3-dimethyl-1,2-dihydropyrano[2,3-c]xanthen-7-one
Synonyms:	Isojacareubin
Standard InCHIKey:	NNWFEKLCJFLWGN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-18(2)6-5-8-12(24-18)7-11(20)13-14(21)9-3-4-10(19)15(22)17(9)23-16(8)13/h3-4,7,19-20,22H,5-6H2,1-2H3
SMILES:	Oc1ccc2c(c1O)oc1c(c2=O)c(O)cc2c1CCC(O2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087608
PubChem CID:	70697351
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
NPO32443	garcinia nujiangensis	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22871217]

☑ 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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	2500.0	nM	PMID[478436]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3800.0	nM	PMID[478436]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	5900.0	nM	PMID[478436]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9500.0	nM	PMID[478436]

☑ 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 NPC470600 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	445
0.1-0.2	2083
0.2-0.3	5195
0.3-0.4	11571
0.4-0.5	5633
0.5-0.6	4043
0.6-0.7	5099
0.7-0.8	4621
0.8-0.85	2133
0.85-0.9	1261
0.9-0.95	547
0.95-1	66

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC218313
0.98	High Similarity	NPC474681
0.9799	High Similarity	NPC256925
0.9799	High Similarity	NPC200246
0.9735	High Similarity	NPC204879
0.9733	High Similarity	NPC5322
0.9733	High Similarity	NPC133970
0.9733	High Similarity	NPC6633
0.9732	High Similarity	NPC273462
0.9732	High Similarity	NPC33051
0.9732	High Similarity	NPC227337
0.9732	High Similarity	NPC49402
0.9732	High Similarity	NPC70433
0.9671	High Similarity	NPC188433
0.9667	High Similarity	NPC152951
0.9667	High Similarity	NPC230149
0.9667	High Similarity	NPC57674
0.9667	High Similarity	NPC168247
0.9667	High Similarity	NPC472280
0.9667	High Similarity	NPC117992
0.9608	High Similarity	NPC29876
0.9608	High Similarity	NPC234644
0.9608	High Similarity	NPC57715
0.9608	High Similarity	NPC134783
0.9608	High Similarity	NPC167678
0.9603	High Similarity	NPC472455
0.9603	High Similarity	NPC115853
0.9545	High Similarity	NPC474034
0.9545	High Similarity	NPC472448
0.9545	High Similarity	NPC474033
0.9545	High Similarity	NPC83922
0.9542	High Similarity	NPC471973
0.9542	High Similarity	NPC204290
0.9539	High Similarity	NPC136674
0.9539	High Similarity	NPC219867
0.9539	High Similarity	NPC161960
0.9539	High Similarity	NPC304008
0.9539	High Similarity	NPC180011
0.9539	High Similarity	NPC187745
0.9539	High Similarity	NPC52889
0.9536	High Similarity	NPC234255
0.9533	High Similarity	NPC237994
0.9484	High Similarity	NPC303460
0.9484	High Similarity	NPC306321
0.9481	High Similarity	NPC471210
0.9481	High Similarity	NPC259456
0.9481	High Similarity	NPC472632
0.9477	High Similarity	NPC184755
0.9477	High Similarity	NPC74178
0.9474	High Similarity	NPC471985
0.9474	High Similarity	NPC138243
0.9474	High Similarity	NPC191146
0.9474	High Similarity	NPC68093
0.9467	High Similarity	NPC154345
0.9459	High Similarity	NPC77378
0.9423	High Similarity	NPC62261
0.9419	High Similarity	NPC474162
0.9419	High Similarity	NPC261470
0.9419	High Similarity	NPC474150
0.9419	High Similarity	NPC25152
0.9416	High Similarity	NPC192686
0.9416	High Similarity	NPC119209
0.9416	High Similarity	NPC118256
0.9416	High Similarity	NPC476980
0.9416	High Similarity	NPC174953
0.9412	High Similarity	NPC78225
0.9412	High Similarity	NPC262286
0.9412	High Similarity	NPC291508
0.9412	High Similarity	NPC471209
0.9412	High Similarity	NPC27337
0.9412	High Similarity	NPC36852
0.9404	High Similarity	NPC257648
0.9404	High Similarity	NPC477231
0.94	High Similarity	NPC29231
0.9396	High Similarity	NPC196277
0.9396	High Similarity	NPC272721
0.9396	High Similarity	NPC43669
0.9363	High Similarity	NPC472449
0.9359	High Similarity	NPC248638
0.9359	High Similarity	NPC236521
0.9359	High Similarity	NPC152659
0.9359	High Similarity	NPC146134
0.9359	High Similarity	NPC124038
0.9359	High Similarity	NPC189473
0.9359	High Similarity	NPC23298
0.9355	High Similarity	NPC471212
0.9355	High Similarity	NPC471211
0.9355	High Similarity	NPC474038
0.9351	High Similarity	NPC473990
0.9351	High Similarity	NPC235448
0.9346	High Similarity	NPC195796
0.9346	High Similarity	NPC35038
0.9346	High Similarity	NPC282307
0.9346	High Similarity	NPC170026
0.9346	High Similarity	NPC472907
0.9346	High Similarity	NPC291878
0.9346	High Similarity	NPC278778
0.9342	High Similarity	NPC472905
0.9342	High Similarity	NPC170492
0.9338	High Similarity	NPC31363
0.9299	High Similarity	NPC472450
0.9299	High Similarity	NPC239752
0.9299	High Similarity	NPC108433
0.9299	High Similarity	NPC275780
0.9299	High Similarity	NPC300053
0.9299	High Similarity	NPC293319
0.9299	High Similarity	NPC50960
0.9295	High Similarity	NPC329760
0.9295	High Similarity	NPC476247
0.9295	High Similarity	NPC220912
0.929	High Similarity	NPC474960
0.929	High Similarity	NPC472624
0.929	High Similarity	NPC475784
0.929	High Similarity	NPC200746
0.9286	High Similarity	NPC129684
0.9286	High Similarity	NPC284820
0.9286	High Similarity	NPC473272
0.9286	High Similarity	NPC79053
0.9286	High Similarity	NPC476981
0.9286	High Similarity	NPC472598
0.9286	High Similarity	NPC299520
0.9286	High Similarity	NPC472963
0.9286	High Similarity	NPC474055
0.9286	High Similarity	NPC67876
0.9281	High Similarity	NPC477503
0.9281	High Similarity	NPC113906
0.9281	High Similarity	NPC45849
0.9281	High Similarity	NPC200761
0.9281	High Similarity	NPC470327
0.9276	High Similarity	NPC471982
0.9276	High Similarity	NPC39732
0.9276	High Similarity	NPC39007
0.9276	High Similarity	NPC472912
0.9276	High Similarity	NPC161277
0.9276	High Similarity	NPC60972
0.9272	High Similarity	NPC3825
0.9272	High Similarity	NPC248102
0.9272	High Similarity	NPC88804
0.9272	High Similarity	NPC472279
0.9245	High Similarity	NPC288813
0.9241	High Similarity	NPC471213
0.9241	High Similarity	NPC37870
0.9241	High Similarity	NPC235610
0.9241	High Similarity	NPC39091
0.9236	High Similarity	NPC472281
0.9236	High Similarity	NPC472625
0.9236	High Similarity	NPC319200
0.9236	High Similarity	NPC205265
0.9236	High Similarity	NPC187491
0.9236	High Similarity	NPC186686
0.9231	High Similarity	NPC266314
0.9231	High Similarity	NPC472634
0.9231	High Similarity	NPC472906
0.9231	High Similarity	NPC258331
0.9231	High Similarity	NPC61010
0.9231	High Similarity	NPC173137
0.9231	High Similarity	NPC26326
0.9231	High Similarity	NPC228383
0.9226	High Similarity	NPC55738
0.9226	High Similarity	NPC185258
0.9226	High Similarity	NPC100123
0.9226	High Similarity	NPC250214
0.9226	High Similarity	NPC172770
0.9226	High Similarity	NPC95936
0.9221	High Similarity	NPC472626
0.9221	High Similarity	NPC209614
0.9221	High Similarity	NPC472916
0.9221	High Similarity	NPC470328
0.9221	High Similarity	NPC276444
0.9221	High Similarity	NPC474638
0.9216	High Similarity	NPC18727
0.9216	High Similarity	NPC213896
0.9216	High Similarity	NPC88645
0.9216	High Similarity	NPC192083
0.9216	High Similarity	NPC292214
0.9216	High Similarity	NPC74924
0.9216	High Similarity	NPC469550
0.9216	High Similarity	NPC271779
0.9216	High Similarity	NPC206238
0.9216	High Similarity	NPC167091
0.9211	High Similarity	NPC251110
0.9211	High Similarity	NPC256406
0.9211	High Similarity	NPC171010
0.92	High Similarity	NPC168803
0.9187	High Similarity	NPC472276
0.9182	High Similarity	NPC477154
0.9182	High Similarity	NPC6588
0.9182	High Similarity	NPC117854
0.9182	High Similarity	NPC8965
0.9177	High Similarity	NPC303174
0.9177	High Similarity	NPC472277
0.9177	High Similarity	NPC234052
0.9177	High Similarity	NPC224280
0.9172	High Similarity	NPC52204
0.9172	High Similarity	NPC472635
0.9172	High Similarity	NPC78332
0.9172	High Similarity	NPC229632
0.9167	High Similarity	NPC471976
0.9167	High Similarity	NPC282009
0.9167	High Similarity	NPC228785

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 NPC470600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	1045
0.2-0.3	1852
0.3-0.4	2720
0.4-0.5	1663
0.5-0.6	977
0.6-0.7	311
0.7-0.8	99
0.8-0.85	39
0.85-0.9	12
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9216	High Similarity	NPD2393	Clinical (unspecified phase)
0.915	High Similarity	NPD1934	Approved
0.9091	High Similarity	NPD2801	Approved
0.8974	High Similarity	NPD3882	Suspended
0.8938	High Similarity	NPD6167	Clinical (unspecified phase)
0.8938	High Similarity	NPD6168	Clinical (unspecified phase)
0.8938	High Similarity	NPD6166	Phase 2
0.8874	High Similarity	NPD1511	Approved
0.8805	High Similarity	NPD5494	Approved
0.8758	High Similarity	NPD1512	Approved
0.872	High Similarity	NPD7074	Phase 3
0.8693	High Similarity	NPD7410	Clinical (unspecified phase)
0.8659	High Similarity	NPD7054	Approved
0.8654	High Similarity	NPD4380	Phase 2
0.8616	High Similarity	NPD4868	Clinical (unspecified phase)
0.8608	High Similarity	NPD1465	Phase 2
0.8606	High Similarity	NPD7472	Approved
0.8598	High Similarity	NPD3818	Discontinued
0.8571	High Similarity	NPD4378	Clinical (unspecified phase)
0.8562	High Similarity	NPD7075	Discontinued
0.8491	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6797	Phase 2
0.8438	Intermediate Similarity	NPD3817	Phase 2
0.8421	Intermediate Similarity	NPD1549	Phase 2
0.8393	Intermediate Similarity	NPD7251	Discontinued
0.8375	Intermediate Similarity	NPD7819	Suspended
0.8365	Intermediate Similarity	NPD7411	Suspended
0.8355	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6232	Discontinued
0.8343	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7808	Phase 3
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD943	Approved
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8293	Intermediate Similarity	NPD6959	Discontinued
0.8225	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1510	Phase 2
0.8214	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD5844	Phase 1
0.82	Intermediate Similarity	NPD1240	Approved
0.817	Intermediate Similarity	NPD2796	Approved
0.8153	Intermediate Similarity	NPD6799	Approved
0.811	Intermediate Similarity	NPD3749	Approved
0.8092	Intermediate Similarity	NPD1607	Approved
0.8036	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2800	Approved
0.7976	Intermediate Similarity	NPD3926	Phase 2
0.7965	Intermediate Similarity	NPD6559	Discontinued
0.7964	Intermediate Similarity	NPD1247	Approved
0.7963	Intermediate Similarity	NPD6599	Discontinued
0.7962	Intermediate Similarity	NPD3750	Approved
0.7952	Intermediate Similarity	NPD919	Approved
0.7939	Intermediate Similarity	NPD7768	Phase 2
0.7933	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5402	Approved
0.7867	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2935	Discontinued
0.7792	Intermediate Similarity	NPD447	Suspended
0.7785	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5403	Approved
0.776	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2799	Discontinued
0.7727	Intermediate Similarity	NPD1613	Approved
0.7727	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6100	Approved
0.7707	Intermediate Similarity	NPD6099	Approved
0.7683	Intermediate Similarity	NPD3226	Approved
0.7677	Intermediate Similarity	NPD230	Phase 1
0.7673	Intermediate Similarity	NPD1243	Approved
0.7669	Intermediate Similarity	NPD920	Approved
0.7658	Intermediate Similarity	NPD2346	Discontinued
0.7658	Intermediate Similarity	NPD2344	Approved
0.7654	Intermediate Similarity	NPD2534	Approved
0.7654	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD5401	Approved
0.7654	Intermediate Similarity	NPD2533	Approved
0.7643	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3748	Approved
0.7628	Intermediate Similarity	NPD6651	Approved
0.7625	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5953	Discontinued
0.7597	Intermediate Similarity	NPD2313	Discontinued
0.7595	Intermediate Similarity	NPD1551	Phase 2
0.7586	Intermediate Similarity	NPD7286	Phase 2
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1933	Approved
0.7532	Intermediate Similarity	NPD3027	Phase 3
0.7529	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD9494	Approved
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7390	Discontinued
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8312	Approved
0.7472	Intermediate Similarity	NPD8313	Approved
0.7469	Intermediate Similarity	NPD2309	Approved
0.7442	Intermediate Similarity	NPD7199	Phase 2
0.7439	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7228	Approved
0.7427	Intermediate Similarity	NPD6234	Discontinued
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4625	Phase 3
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD3787	Discontinued
0.7386	Intermediate Similarity	NPD1203	Approved
0.7362	Intermediate Similarity	NPD6190	Approved
0.736	Intermediate Similarity	NPD7685	Pre-registration
0.7356	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4908	Phase 1
0.7312	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1653	Approved
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7254	Intermediate Similarity	NPD8151	Discontinued
0.7253	Intermediate Similarity	NPD8150	Discontinued
0.724	Intermediate Similarity	NPD7584	Approved
0.7237	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD37	Approved
0.7229	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2798	Approved
0.7209	Intermediate Similarity	NPD4967	Phase 2
0.7209	Intermediate Similarity	NPD4966	Approved
0.7209	Intermediate Similarity	NPD4965	Approved
0.7205	Intermediate Similarity	NPD4308	Phase 3
0.7204	Intermediate Similarity	NPD4363	Phase 3
0.7204	Intermediate Similarity	NPD4360	Phase 2
0.72	Intermediate Similarity	NPD5710	Approved
0.72	Intermediate Similarity	NPD5711	Approved
0.719	Intermediate Similarity	NPD9269	Phase 2
0.719	Intermediate Similarity	NPD9717	Approved
0.7174	Intermediate Similarity	NPD4287	Approved
0.7173	Intermediate Similarity	NPD7435	Discontinued
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7698	Approved
0.7161	Intermediate Similarity	NPD1470	Approved
0.716	Intermediate Similarity	NPD7458	Discontinued
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5404	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.7159	Intermediate Similarity	NPD5242	Approved
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5124	Phase 1
0.7124	Intermediate Similarity	NPD1610	Phase 2
0.7119	Intermediate Similarity	NPD2403	Approved
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7099	Intermediate Similarity	NPD7033	Discontinued
0.7092	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7783	Phase 2
0.7083	Intermediate Similarity	NPD5049	Phase 3
0.7078	Intermediate Similarity	NPD1608	Approved
0.7076	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2424	Discontinued
0.7066	Intermediate Similarity	NPD4357	Discontinued
0.7056	Intermediate Similarity	NPD1729	Discontinued
0.7052	Intermediate Similarity	NPD4288	Approved
0.7052	Intermediate Similarity	NPD5353	Approved
0.7051	Intermediate Similarity	NPD2797	Approved
0.7048	Intermediate Similarity	NPD2354	Approved
0.7047	Intermediate Similarity	NPD7871	Phase 2
0.7047	Intermediate Similarity	NPD7870	Phase 2
0.7044	Intermediate Similarity	NPD411	Approved
0.7044	Intermediate Similarity	NPD3764	Approved
0.7035	Intermediate Similarity	NPD6844	Discontinued
0.7031	Intermediate Similarity	NPD6823	Phase 2
0.7021	Intermediate Similarity	NPD6534	Approved
0.7021	Intermediate Similarity	NPD6535	Approved
0.702	Intermediate Similarity	NPD5536	Phase 2
0.7019	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6585	Discontinued
0.7013	Intermediate Similarity	NPD1201	Approved
0.7013	Intermediate Similarity	NPD422	Phase 1
0.7012	Intermediate Similarity	NPD7266	Discontinued
0.7012	Intermediate Similarity	NPD1471	Phase 3
0.7006	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD7700	Phase 2
0.7	Intermediate Similarity	NPD7699	Phase 2

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