NPASS Compound

Structure

NPC236520 OpenBabel07101718232D 25 27 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 -2.5981 3.5000 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 1.7321 -1.0000 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 1.7321 0.0000 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 3.4641 -1.0000 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 -0.8660 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 1 8 2 0 0 0 0 2 5 2 0 0 0 0 2 8 1 0 0 0 0 3 6 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 23 2 0 0 0 0 17 24 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.06
Volume:	329.382
LogP:	2.266
LogD:	1.483
LogS:	-3.807
# Rotatable Bonds:	2
TPSA:	135.29
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	2.59
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.35
MDCK Permeability:	6.022179150022566e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.181

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	96.65470123291016%
Volume Distribution (VD):	0.334
Pgp-substrate:	1.9640803337097168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.649
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.12
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.581
CYP2C9-substrate:	0.655
CYP2D6-inhibitor:	0.38
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	1.078
Half-life (T1/2):	0.63

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.914
Drug-inuced Liver Injury (DILI):	0.992
AMES Toxicity:	0.67
Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.485
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.262

Download Data

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

Natural Product: NPC236520

Natural Product ID:	NPC236520
*Common Name:**	PNLQLFIVEMDDQE-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PNLQLFIVEMDDQE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O7/c19-10-4-1-8(2-5-10)13-15(22)17(24)14(18(25)16(13)23)9-3-6-11(20)12(21)7-9/h1-7,19-22,25H
SMILES:	c1cc(ccc1C1=C(C(=O)C(=C(C1=O)O)c1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3238008
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

*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
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10757716]
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	Eukaryota	n.a.	Tibet, China	n.a.	PMID[24645629]
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
IC50	3
Others	1

Activity Type	# Activity
NON-MOLECULAR	2
Others	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	9000.0	nM	PMID[528147]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	84.0	U	PMID[528147]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	13000.0	nM	PMID[528147]
NPT625	Tissue	Liver	Mus musculus	IC50	=	49000.0	nM	PMID[528147]
NPT2	Others	Unspecified		IC50	=	3530.0	nM	PMID[528147]

☑ 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 NPC236520 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	331
0.1-0.2	1670
0.2-0.3	4353
0.3-0.4	11868
0.4-0.5	6517
0.5-0.6	6315
0.6-0.7	9127
0.7-0.8	2352
0.8-0.85	139
0.85-0.9	18
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC294361
0.9417	High Similarity	NPC156539
0.9217	High Similarity	NPC277394
0.9217	High Similarity	NPC61062
0.9217	High Similarity	NPC299252
0.9027	High Similarity	NPC21162
0.8814	High Similarity	NPC150919
0.8783	High Similarity	NPC297657
0.872	High Similarity	NPC234175
0.8707	High Similarity	NPC51698
0.8689	High Similarity	NPC86900
0.8644	High Similarity	NPC4665
0.864	High Similarity	NPC107672
0.8595	High Similarity	NPC265454
0.8595	High Similarity	NPC34634
0.855	High Similarity	NPC264022
0.8548	High Similarity	NPC85565
0.8548	High Similarity	NPC288945
0.8534	High Similarity	NPC222084
0.8527	High Similarity	NPC4170
0.8525	High Similarity	NPC98305
0.8509	High Similarity	NPC70843
0.8492	Intermediate Similarity	NPC324209
0.8438	Intermediate Similarity	NPC26697
0.8438	Intermediate Similarity	NPC233056
0.8438	Intermediate Similarity	NPC66905
0.8413	Intermediate Similarity	NPC90128
0.8413	Intermediate Similarity	NPC84076
0.8413	Intermediate Similarity	NPC303680
0.8385	Intermediate Similarity	NPC294226
0.8376	Intermediate Similarity	NPC116842
0.8372	Intermediate Similarity	NPC34070
0.8372	Intermediate Similarity	NPC469526
0.8362	Intermediate Similarity	NPC17525
0.8348	Intermediate Similarity	NPC95178
0.8348	Intermediate Similarity	NPC69332
0.8348	Intermediate Similarity	NPC29989
0.8346	Intermediate Similarity	NPC276466
0.8346	Intermediate Similarity	NPC123722
0.8346	Intermediate Similarity	NPC151167
0.8346	Intermediate Similarity	NPC5018
0.8346	Intermediate Similarity	NPC284409
0.8346	Intermediate Similarity	NPC123228
0.8333	Intermediate Similarity	NPC52087
0.8333	Intermediate Similarity	NPC7464
0.8333	Intermediate Similarity	NPC322197
0.8333	Intermediate Similarity	NPC471511
0.8319	Intermediate Similarity	NPC148969
0.8308	Intermediate Similarity	NPC135801
0.8306	Intermediate Similarity	NPC472271
0.8295	Intermediate Similarity	NPC244441
0.8295	Intermediate Similarity	NPC172673
0.8295	Intermediate Similarity	NPC117609
0.8291	Intermediate Similarity	NPC88141
0.8279	Intermediate Similarity	NPC63126
0.8268	Intermediate Similarity	NPC179777
0.8244	Intermediate Similarity	NPC471749
0.824	Intermediate Similarity	NPC91478
0.8231	Intermediate Similarity	NPC198388
0.823	Intermediate Similarity	NPC223393
0.8226	Intermediate Similarity	NPC248363
0.8217	Intermediate Similarity	NPC94810
0.8217	Intermediate Similarity	NPC304622
0.8211	Intermediate Similarity	NPC156654
0.8209	Intermediate Similarity	NPC289358
0.8209	Intermediate Similarity	NPC175552
0.8209	Intermediate Similarity	NPC477849
0.8209	Intermediate Similarity	NPC28592
0.8209	Intermediate Similarity	NPC165191
0.8209	Intermediate Similarity	NPC42384
0.8209	Intermediate Similarity	NPC245760
0.8209	Intermediate Similarity	NPC23667
0.8209	Intermediate Similarity	NPC473479
0.8209	Intermediate Similarity	NPC149773
0.8209	Intermediate Similarity	NPC473779
0.8209	Intermediate Similarity	NPC230811
0.8209	Intermediate Similarity	NPC469857
0.8209	Intermediate Similarity	NPC50615
0.8209	Intermediate Similarity	NPC51531
0.8209	Intermediate Similarity	NPC114333
0.8209	Intermediate Similarity	NPC5014
0.8209	Intermediate Similarity	NPC157284
0.8209	Intermediate Similarity	NPC91887
0.8209	Intermediate Similarity	NPC297797
0.8209	Intermediate Similarity	NPC46242
0.8197	Intermediate Similarity	NPC278652
0.8195	Intermediate Similarity	NPC264112
0.8195	Intermediate Similarity	NPC65005
0.8195	Intermediate Similarity	NPC324929
0.8195	Intermediate Similarity	NPC194764
0.819	Intermediate Similarity	NPC188677
0.8189	Intermediate Similarity	NPC257589
0.8189	Intermediate Similarity	NPC53305
0.8182	Intermediate Similarity	NPC248150
0.8182	Intermediate Similarity	NPC278102
0.8174	Intermediate Similarity	NPC79672
0.8174	Intermediate Similarity	NPC120693
0.8174	Intermediate Similarity	NPC8931
0.8174	Intermediate Similarity	NPC261573
0.8168	Intermediate Similarity	NPC25581
0.8168	Intermediate Similarity	NPC239302
0.8168	Intermediate Similarity	NPC18074
0.8168	Intermediate Similarity	NPC5419
0.8168	Intermediate Similarity	NPC61
0.816	Intermediate Similarity	NPC120545
0.8151	Intermediate Similarity	NPC268388
0.8151	Intermediate Similarity	NPC212718
0.8148	Intermediate Similarity	NPC191280
0.8148	Intermediate Similarity	NPC294330
0.8136	Intermediate Similarity	NPC228343
0.8136	Intermediate Similarity	NPC254833
0.8134	Intermediate Similarity	NPC290030
0.8134	Intermediate Similarity	NPC170742
0.8125	Intermediate Similarity	NPC92207
0.8125	Intermediate Similarity	NPC127937
0.8125	Intermediate Similarity	NPC276014
0.812	Intermediate Similarity	NPC72918
0.812	Intermediate Similarity	NPC153088
0.812	Intermediate Similarity	NPC258502
0.812	Intermediate Similarity	NPC226699
0.8115	Intermediate Similarity	NPC325646
0.8115	Intermediate Similarity	NPC28951
0.811	Intermediate Similarity	NPC474766
0.811	Intermediate Similarity	NPC471927
0.8106	Intermediate Similarity	NPC155209
0.8106	Intermediate Similarity	NPC168799
0.8106	Intermediate Similarity	NPC138472
0.8103	Intermediate Similarity	NPC13495
0.8103	Intermediate Similarity	NPC239291
0.8095	Intermediate Similarity	NPC139171
0.8095	Intermediate Similarity	NPC164947
0.8088	Intermediate Similarity	NPC473527
0.8087	Intermediate Similarity	NPC135784
0.8083	Intermediate Similarity	NPC231717
0.8074	Intermediate Similarity	NPC61398
0.8074	Intermediate Similarity	NPC469680
0.8074	Intermediate Similarity	NPC416
0.8074	Intermediate Similarity	NPC471974
0.8074	Intermediate Similarity	NPC469681
0.8067	Intermediate Similarity	NPC79793
0.8067	Intermediate Similarity	NPC120982
0.8067	Intermediate Similarity	NPC174096
0.8067	Intermediate Similarity	NPC226401
0.8067	Intermediate Similarity	NPC147634
0.8065	Intermediate Similarity	NPC263386
0.8065	Intermediate Similarity	NPC141791
0.8062	Intermediate Similarity	NPC32163
0.8062	Intermediate Similarity	NPC16651
0.8053	Intermediate Similarity	NPC109955
0.8047	Intermediate Similarity	NPC197832
0.8047	Intermediate Similarity	NPC3221
0.8043	Intermediate Similarity	NPC474692
0.8034	Intermediate Similarity	NPC1786
0.8034	Intermediate Similarity	NPC294902
0.8034	Intermediate Similarity	NPC1075
0.8034	Intermediate Similarity	NPC6984
0.8031	Intermediate Similarity	NPC257976
0.8031	Intermediate Similarity	NPC242372
0.8031	Intermediate Similarity	NPC164778
0.8031	Intermediate Similarity	NPC4181
0.8031	Intermediate Similarity	NPC306100
0.8017	Intermediate Similarity	NPC11824
0.8015	Intermediate Similarity	NPC27659
0.8015	Intermediate Similarity	NPC472903
0.8	Intermediate Similarity	NPC277559
0.8	Intermediate Similarity	NPC96024
0.8	Intermediate Similarity	NPC187583
0.8	Intermediate Similarity	NPC167463
0.8	Intermediate Similarity	NPC226661
0.8	Intermediate Similarity	NPC179002
0.8	Intermediate Similarity	NPC476393
0.8	Intermediate Similarity	NPC257430
0.8	Intermediate Similarity	NPC147418
0.7985	Intermediate Similarity	NPC139519
0.7985	Intermediate Similarity	NPC43353
0.7984	Intermediate Similarity	NPC311091
0.7984	Intermediate Similarity	NPC15837
0.7984	Intermediate Similarity	NPC275519
0.7984	Intermediate Similarity	NPC471033
0.7984	Intermediate Similarity	NPC249435
0.7983	Intermediate Similarity	NPC55617
0.7983	Intermediate Similarity	NPC62258
0.7983	Intermediate Similarity	NPC95172
0.7982	Intermediate Similarity	NPC280869
0.7971	Intermediate Similarity	NPC471972
0.7971	Intermediate Similarity	NPC469855
0.7971	Intermediate Similarity	NPC176030
0.7971	Intermediate Similarity	NPC192597
0.7971	Intermediate Similarity	NPC169214
0.7971	Intermediate Similarity	NPC471971
0.7971	Intermediate Similarity	NPC229218
0.7971	Intermediate Similarity	NPC141817
0.7971	Intermediate Similarity	NPC30846
0.797	Intermediate Similarity	NPC474715
0.797	Intermediate Similarity	NPC111845
0.7969	Intermediate Similarity	NPC199273
0.7969	Intermediate Similarity	NPC164014
0.7969	Intermediate Similarity	NPC312404
0.7969	Intermediate Similarity	NPC273686
0.7969	Intermediate Similarity	NPC15127

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 NPC236520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	960
0.2-0.3	1354
0.3-0.4	2825
0.4-0.5	2055
0.5-0.6	1187
0.6-0.7	384
0.7-0.8	62
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8308	Intermediate Similarity	NPD943	Approved
0.8136	Intermediate Similarity	NPD3022	Approved
0.8136	Intermediate Similarity	NPD3021	Approved
0.7926	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1512	Approved
0.7842	Intermediate Similarity	NPD6190	Approved
0.7812	Intermediate Similarity	NPD9269	Phase 2
0.773	Intermediate Similarity	NPD1511	Approved
0.7717	Intermediate Similarity	NPD2932	Approved
0.7652	Intermediate Similarity	NPD9494	Approved
0.7643	Intermediate Similarity	NPD8166	Discontinued
0.7597	Intermediate Similarity	NPD1201	Approved
0.7578	Intermediate Similarity	NPD3019	Approved
0.754	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9268	Approved
0.75	Intermediate Similarity	NPD1470	Approved
0.7478	Intermediate Similarity	NPD2933	Approved
0.7478	Intermediate Similarity	NPD2934	Approved
0.7445	Intermediate Similarity	NPD230	Phase 1
0.7444	Intermediate Similarity	NPD258	Approved
0.7444	Intermediate Similarity	NPD257	Approved
0.7432	Intermediate Similarity	NPD1934	Approved
0.7414	Intermediate Similarity	NPD2860	Approved
0.7414	Intermediate Similarity	NPD2859	Approved
0.7413	Intermediate Similarity	NPD3300	Phase 2
0.74	Intermediate Similarity	NPD3882	Suspended
0.7388	Intermediate Similarity	NPD9569	Approved
0.7383	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2801	Approved
0.7373	Intermediate Similarity	NPD3020	Approved
0.7361	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5536	Phase 2
0.7286	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD228	Approved
0.7273	Intermediate Similarity	NPD1237	Approved
0.7231	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3764	Approved
0.7222	Intermediate Similarity	NPD9379	Approved
0.7222	Intermediate Similarity	NPD9377	Approved
0.7192	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6166	Phase 2
0.7174	Intermediate Similarity	NPD259	Phase 1
0.7167	Intermediate Similarity	NPD1242	Phase 1
0.7163	Intermediate Similarity	NPD1510	Phase 2
0.7154	Intermediate Similarity	NPD9545	Approved
0.7153	Intermediate Similarity	NPD9537	Phase 1
0.7153	Intermediate Similarity	NPD9536	Phase 1
0.7122	Intermediate Similarity	NPD825	Approved
0.7122	Intermediate Similarity	NPD826	Approved
0.7121	Intermediate Similarity	NPD3023	Approved
0.7121	Intermediate Similarity	NPD3026	Approved
0.7114	Intermediate Similarity	NPD3455	Phase 2
0.7111	Intermediate Similarity	NPD1164	Approved
0.7105	Intermediate Similarity	NPD3817	Phase 2
0.7099	Intermediate Similarity	NPD3024	Approved
0.7099	Intermediate Similarity	NPD3025	Approved
0.709	Intermediate Similarity	NPD1755	Approved
0.7075	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD555	Phase 2
0.7071	Intermediate Similarity	NPD274	Approved
0.7071	Intermediate Similarity	NPD275	Approved
0.7063	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7266	Discontinued
0.7059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5310	Approved
0.7037	Intermediate Similarity	NPD5311	Approved
0.7031	Intermediate Similarity	NPD1241	Discontinued
0.7029	Intermediate Similarity	NPD7095	Approved
0.7015	Intermediate Similarity	NPD1608	Approved
0.7015	Intermediate Similarity	NPD3972	Approved
0.7015	Intermediate Similarity	NPD1481	Phase 2
0.7007	Intermediate Similarity	NPD7390	Discontinued
0.7	Intermediate Similarity	NPD1240	Approved
0.7	Intermediate Similarity	NPD9495	Approved
0.6993	Remote Similarity	NPD5404	Approved
0.6993	Remote Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD2935	Discontinued
0.6993	Remote Similarity	NPD5408	Approved
0.6993	Remote Similarity	NPD5405	Approved
0.6986	Remote Similarity	NPD2354	Approved
0.6985	Remote Similarity	NPD3053	Approved
0.6985	Remote Similarity	NPD3055	Approved
0.6978	Remote Similarity	NPD6798	Discontinued
0.6957	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6797	Phase 2
0.6944	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2344	Approved
0.6944	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1535	Discovery
0.6929	Remote Similarity	NPD6233	Phase 2
0.6918	Remote Similarity	NPD3750	Approved
0.6918	Remote Similarity	NPD4628	Phase 3
0.6914	Remote Similarity	NPD7251	Discontinued
0.6912	Remote Similarity	NPD1283	Approved
0.6906	Remote Similarity	NPD3027	Phase 3
0.6905	Remote Similarity	NPD9266	Approved
0.6905	Remote Similarity	NPD74	Approved
0.6901	Remote Similarity	NPD1607	Approved
0.6899	Remote Similarity	NPD5283	Phase 1
0.6897	Remote Similarity	NPD1549	Phase 2
0.6891	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3818	Discontinued
0.6875	Remote Similarity	NPD9570	Approved
0.6871	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3268	Approved
0.6852	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2629	Approved
0.6842	Remote Similarity	NPD4380	Phase 2
0.6842	Remote Similarity	NPD111	Approved
0.6842	Remote Similarity	NPD1651	Approved
0.6833	Remote Similarity	NPD844	Approved
0.6832	Remote Similarity	NPD7054	Approved
0.6831	Remote Similarity	NPD6355	Discontinued
0.6825	Remote Similarity	NPD9264	Approved
0.6825	Remote Similarity	NPD2342	Discontinued
0.6825	Remote Similarity	NPD9267	Approved
0.6825	Remote Similarity	NPD9263	Approved
0.6818	Remote Similarity	NPD1465	Phase 2
0.6812	Remote Similarity	NPD2798	Approved
0.6809	Remote Similarity	NPD6663	Approved
0.6809	Remote Similarity	NPD4062	Phase 3
0.6795	Remote Similarity	NPD7075	Discontinued
0.6794	Remote Similarity	NPD256	Approved
0.6794	Remote Similarity	NPD255	Approved
0.6791	Remote Similarity	NPD17	Approved
0.6791	Remote Similarity	NPD9384	Approved
0.6791	Remote Similarity	NPD9381	Approved
0.679	Remote Similarity	NPD7472	Approved
0.679	Remote Similarity	NPD7074	Phase 3
0.6788	Remote Similarity	NPD1876	Approved
0.6779	Remote Similarity	NPD6799	Approved
0.6777	Remote Similarity	NPD288	Approved
0.6768	Remote Similarity	NPD7808	Phase 3
0.6767	Remote Similarity	NPD1894	Discontinued
0.6763	Remote Similarity	NPD5736	Approved
0.6761	Remote Similarity	NPD3062	Approved
0.6761	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3061	Approved
0.6761	Remote Similarity	NPD1613	Approved
0.6761	Remote Similarity	NPD3059	Approved
0.6761	Remote Similarity	NPD4060	Phase 1
0.6757	Remote Similarity	NPD2309	Approved
0.675	Remote Similarity	NPD1220	Phase 1
0.6748	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3028	Approved
0.6747	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD9568	Approved
0.6742	Remote Similarity	NPD9493	Approved
0.6739	Remote Similarity	NPD2797	Approved
0.6739	Remote Similarity	NPD1203	Approved
0.6738	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2313	Discontinued
0.6732	Remote Similarity	NPD7028	Phase 2
0.673	Remote Similarity	NPD6232	Discontinued
0.6727	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD447	Suspended
0.6712	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2353	Approved
0.671	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7473	Discontinued
0.6691	Remote Similarity	NPD1281	Approved
0.6691	Remote Similarity	NPD3092	Approved
0.669	Remote Similarity	NPD2799	Discontinued
0.6667	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2286	Discontinued
0.6667	Remote Similarity	NPD3225	Approved
0.6667	Remote Similarity	NPD5314	Approved
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD1202	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4878	Approved
0.6642	Remote Similarity	NPD3091	Approved
0.6641	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.664	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.664	Remote Similarity	NPD1930	Approved
0.664	Remote Similarity	NPD1929	Approved
0.6626	Remote Similarity	NPD1221	Approved
0.6623	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD3267	Approved
0.6619	Remote Similarity	NPD3266	Approved
0.6619	Remote Similarity	NPD3094	Phase 2
0.6618	Remote Similarity	NPD3847	Discontinued
0.6599	Remote Similarity	NPD2346	Discontinued
0.6594	Remote Similarity	NPD9622	Approved
0.6593	Remote Similarity	NPD4093	Discontinued
0.6591	Remote Similarity	NPD9281	Approved
0.6591	Remote Similarity	NPD5951	Approved
0.6589	Remote Similarity	NPD4750	Phase 3
0.6582	Remote Similarity	NPD4381	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