NPASS Compound

Structure

NPC52106 OpenBabel07101718192D 28 29 0 0 0 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 -1.7321 1.0000 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 -4.3301 -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 -0.0000 1.0000 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 -3.4641 -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 -0.8660 -0.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 2 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 13 2 0 0 0 0 10 28 1 0 0 0 0 11 24 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 26 1 0 0 0 0 20 23 2 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.25
Volume:	381.86
LogP:	4.516
LogD:	4.231
LogS:	-5.01
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.756
Synthetic Accessibility Score:	4.596
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.772
MDCK Permeability:	3.070660022785887e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.389
30% Bioavailability (F30%):	0.84

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	88.59622955322266%
Volume Distribution (VD):	1.613
Pgp-substrate:	5.3057050704956055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.318
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.492
CYP2C9-substrate:	0.152
CYP2D6-inhibitor:	0.406
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.649

ADMET: Excretion

Clearance (CL):	3.165
Half-life (T1/2):	0.575

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.16
Skin Sensitization:	0.949
Carcinogencity:	0.054
Eye Corrosion:	0.58
Eye Irritation:	0.844
Respiratory Toxicity:	0.87

Download Data

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

Natural Product: NPC52106

Natural Product ID:	NPC52106
*Common Name:**	3-O-Methylfunicone
IUPAC Name:	methyl 3,5-dimethoxy-2-[5-methoxy-4-oxo-6-[(E)-prop-1-enyl]pyran-3-carbonyl]benzoate
Synonyms:
Standard InCHIKey:	WGLRJONCGNNMKL-VOTSOKGWSA-N
Standard InCHI:	InChI=1S/C20H20O8/c1-6-7-14-19(26-4)18(22)13(10-28-14)17(21)16-12(20(23)27-5)8-11(24-2)9-15(16)25-3/h6-10H,1-5H3/b7-6+
SMILES:	C/C=C/c1c(c(=O)c(co1)C(=O)c1c(cc(cc1OC)OC)C(=O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593571
PubChem CID:	10548301
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004297] Aryl-phenylketones

*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
NPO33336	Penicillium sp. HN29-3B1	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26230970]

☑ 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
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	IC50	>	100000.0	nM	PMID[503860]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	IC50	=	12500.0	nM	PMID[503861]
NPT6281	Individual Protein	DNA polymerase iota	Mus musculus	IC50	=	34000.0	nM	PMID[503861]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	IC50	=	50000.0	nM	PMID[503861]

☑ 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 NPC52106 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	460
0.1-0.2	1835
0.2-0.3	4766
0.3-0.4	10261
0.4-0.5	7727
0.5-0.6	3996
0.6-0.7	5714
0.7-0.8	5952
0.8-0.85	1775
0.85-0.9	204
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9236	High Similarity	NPC184702
0.9097	High Similarity	NPC297985
0.8973	High Similarity	NPC470932
0.8912	High Similarity	NPC474446
0.8904	High Similarity	NPC215451
0.8904	High Similarity	NPC277369
0.8882	High Similarity	NPC99381
0.8867	High Similarity	NPC164762
0.8859	High Similarity	NPC172329
0.8859	High Similarity	NPC153417
0.8859	High Similarity	NPC2569
0.8836	High Similarity	NPC471640
0.8836	High Similarity	NPC471644
0.8828	High Similarity	NPC109007
0.8808	High Similarity	NPC91809
0.88	High Similarity	NPC84142
0.8784	High Similarity	NPC49282
0.8776	High Similarity	NPC472006
0.8776	High Similarity	NPC471643
0.8776	High Similarity	NPC471639
0.8758	High Similarity	NPC317585
0.8742	High Similarity	NPC295036
0.8734	High Similarity	NPC472895
0.8733	High Similarity	NPC215711
0.8733	High Similarity	NPC73411
0.8725	High Similarity	NPC472033
0.8725	High Similarity	NPC107625
0.8707	High Similarity	NPC49108
0.8707	High Similarity	NPC250755
0.8707	High Similarity	NPC469579
0.8684	High Similarity	NPC70016
0.8684	High Similarity	NPC215921
0.8679	High Similarity	NPC472894
0.8671	High Similarity	NPC223354
0.8667	High Similarity	NPC210320
0.8667	High Similarity	NPC472036
0.8658	High Similarity	NPC472034
0.8649	High Similarity	NPC51106
0.8649	High Similarity	NPC167663
0.8645	High Similarity	NPC263483
0.8639	High Similarity	NPC1704
0.8639	High Similarity	NPC475730
0.8639	High Similarity	NPC67650
0.8639	High Similarity	NPC474037
0.863	High Similarity	NPC52358
0.8618	High Similarity	NPC469619
0.8618	High Similarity	NPC470107
0.8618	High Similarity	NPC56204
0.8618	High Similarity	NPC469670
0.8618	High Similarity	NPC474660
0.8618	High Similarity	NPC473466
0.8601	High Similarity	NPC182428
0.8591	High Similarity	NPC475201
0.8581	High Similarity	NPC474385
0.8581	High Similarity	NPC474983
0.8571	High Similarity	NPC49242
0.8571	High Similarity	NPC472515
0.8571	High Similarity	NPC136095
0.8562	High Similarity	NPC240768
0.8562	High Similarity	NPC200773
0.8562	High Similarity	NPC253616
0.8562	High Similarity	NPC474170
0.8562	High Similarity	NPC472535
0.8562	High Similarity	NPC474388
0.8553	High Similarity	NPC4423
0.8553	High Similarity	NPC77325
0.8543	High Similarity	NPC474999
0.8543	High Similarity	NPC259632
0.8533	High Similarity	NPC312789
0.8533	High Similarity	NPC28632
0.8526	High Similarity	NPC472889
0.8526	High Similarity	NPC246466
0.8523	High Similarity	NPC478202
0.8523	High Similarity	NPC469542
0.8516	High Similarity	NPC478221
0.8516	High Similarity	NPC276059
0.8516	High Similarity	NPC241774
0.8516	High Similarity	NPC34725
0.8516	High Similarity	NPC122623
0.8516	High Similarity	NPC472890
0.8516	High Similarity	NPC471746
0.8514	High Similarity	NPC244923
0.8514	High Similarity	NPC90411
0.8514	High Similarity	NPC158634
0.8506	High Similarity	NPC475116
0.8503	High Similarity	NPC25427
0.8503	High Similarity	NPC92655
0.8503	High Similarity	NPC36414
0.8497	Intermediate Similarity	NPC177839
0.8493	Intermediate Similarity	NPC254741
0.8493	Intermediate Similarity	NPC284184
0.8493	Intermediate Similarity	NPC72452
0.8493	Intermediate Similarity	NPC268081
0.8493	Intermediate Similarity	NPC61546
0.8493	Intermediate Similarity	NPC301341
0.8493	Intermediate Similarity	NPC135837
0.8487	Intermediate Similarity	NPC240622
0.8487	Intermediate Similarity	NPC471642
0.8487	Intermediate Similarity	NPC471641
0.8487	Intermediate Similarity	NPC240253
0.8483	Intermediate Similarity	NPC180905
0.8483	Intermediate Similarity	NPC182496
0.8483	Intermediate Similarity	NPC470844
0.8481	Intermediate Similarity	NPC317544
0.8477	Intermediate Similarity	NPC120924
0.8477	Intermediate Similarity	NPC473927
0.8477	Intermediate Similarity	NPC216314
0.8477	Intermediate Similarity	NPC163846
0.8477	Intermediate Similarity	NPC225173
0.8477	Intermediate Similarity	NPC195919
0.8467	Intermediate Similarity	NPC280404
0.8467	Intermediate Similarity	NPC86373
0.8467	Intermediate Similarity	NPC277426
0.8467	Intermediate Similarity	NPC210425
0.8467	Intermediate Similarity	NPC27106
0.8462	Intermediate Similarity	NPC472050
0.8462	Intermediate Similarity	NPC257277
0.8456	Intermediate Similarity	NPC185607
0.8452	Intermediate Similarity	NPC478231
0.8452	Intermediate Similarity	NPC155686
0.8452	Intermediate Similarity	NPC137301
0.8452	Intermediate Similarity	NPC186507
0.8451	Intermediate Similarity	NPC211120
0.8447	Intermediate Similarity	NPC283041
0.8442	Intermediate Similarity	NPC189773
0.8442	Intermediate Similarity	NPC473732
0.8438	Intermediate Similarity	NPC191930
0.8435	Intermediate Similarity	NPC191835
0.8435	Intermediate Similarity	NPC103001
0.8435	Intermediate Similarity	NPC33144
0.8435	Intermediate Similarity	NPC478200
0.8431	Intermediate Similarity	NPC198927
0.8431	Intermediate Similarity	NPC476684
0.8429	Intermediate Similarity	NPC65041
0.8428	Intermediate Similarity	NPC475144
0.8421	Intermediate Similarity	NPC299923
0.8421	Intermediate Similarity	NPC125801
0.8421	Intermediate Similarity	NPC14098
0.8421	Intermediate Similarity	NPC137296
0.8418	Intermediate Similarity	NPC313368
0.8418	Intermediate Similarity	NPC243701
0.8414	Intermediate Similarity	NPC311339
0.8411	Intermediate Similarity	NPC171656
0.8411	Intermediate Similarity	NPC213482
0.8411	Intermediate Similarity	NPC134621
0.8408	Intermediate Similarity	NPC478225
0.8397	Intermediate Similarity	NPC170189
0.8397	Intermediate Similarity	NPC69043
0.8397	Intermediate Similarity	NPC208173
0.8397	Intermediate Similarity	NPC478230
0.8392	Intermediate Similarity	NPC473271
0.8389	Intermediate Similarity	NPC478217
0.8389	Intermediate Similarity	NPC470856
0.8389	Intermediate Similarity	NPC313123
0.8389	Intermediate Similarity	NPC478201
0.8389	Intermediate Similarity	NPC472035
0.8387	Intermediate Similarity	NPC478224
0.8387	Intermediate Similarity	NPC184284
0.8387	Intermediate Similarity	NPC76041
0.8387	Intermediate Similarity	NPC115249
0.8387	Intermediate Similarity	NPC271681
0.8385	Intermediate Similarity	NPC20237
0.8378	Intermediate Similarity	NPC279668
0.8378	Intermediate Similarity	NPC55162
0.8378	Intermediate Similarity	NPC90665
0.8378	Intermediate Similarity	NPC278323
0.8378	Intermediate Similarity	NPC472368
0.8378	Intermediate Similarity	NPC32360
0.8378	Intermediate Similarity	NPC12175
0.8378	Intermediate Similarity	NPC309154
0.8378	Intermediate Similarity	NPC268052
0.8377	Intermediate Similarity	NPC158866
0.8377	Intermediate Similarity	NPC191104
0.8377	Intermediate Similarity	NPC255641
0.8377	Intermediate Similarity	NPC216917
0.8377	Intermediate Similarity	NPC472891
0.8377	Intermediate Similarity	NPC475460
0.8377	Intermediate Similarity	NPC85131
0.8377	Intermediate Similarity	NPC201547
0.8377	Intermediate Similarity	NPC290954
0.8377	Intermediate Similarity	NPC147735
0.8377	Intermediate Similarity	NPC60413
0.8377	Intermediate Similarity	NPC259058
0.8377	Intermediate Similarity	NPC470568
0.8375	Intermediate Similarity	NPC249181
0.8367	Intermediate Similarity	NPC472516
0.8367	Intermediate Similarity	NPC70380
0.8367	Intermediate Similarity	NPC476333
0.8367	Intermediate Similarity	NPC472364
0.8367	Intermediate Similarity	NPC473391
0.8367	Intermediate Similarity	NPC472367
0.8366	Intermediate Similarity	NPC37139
0.8366	Intermediate Similarity	NPC472056
0.8355	Intermediate Similarity	NPC310259
0.8355	Intermediate Similarity	NPC153758
0.8355	Intermediate Similarity	NPC237208
0.8355	Intermediate Similarity	NPC202112
0.8355	Intermediate Similarity	NPC51513
0.8354	Intermediate Similarity	NPC477410
0.8354	Intermediate Similarity	NPC324736

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 NPC52106 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	1004
0.2-0.3	1928
0.3-0.4	2654
0.4-0.5	1751
0.5-0.6	915
0.6-0.7	347
0.7-0.8	112
0.8-0.85	36
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7819	Suspended
0.8516	High Similarity	NPD3817	Phase 2
0.8503	High Similarity	NPD970	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD6799	Approved
0.8377	Intermediate Similarity	NPD6599	Discontinued
0.8367	Intermediate Similarity	NPD2796	Approved
0.8289	Intermediate Similarity	NPD2533	Approved
0.8289	Intermediate Similarity	NPD2534	Approved
0.8289	Intermediate Similarity	NPD2532	Approved
0.8269	Intermediate Similarity	NPD6801	Discontinued
0.8217	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6232	Discontinued
0.8182	Intermediate Similarity	NPD920	Approved
0.8176	Intermediate Similarity	NPD7075	Discontinued
0.8176	Intermediate Similarity	NPD3748	Approved
0.8176	Intermediate Similarity	NPD1510	Phase 2
0.817	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5402	Approved
0.816	Intermediate Similarity	NPD7473	Discontinued
0.8146	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD919	Approved
0.8052	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD3926	Phase 2
0.8027	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD3882	Suspended
0.7975	Intermediate Similarity	NPD7411	Suspended
0.7961	Intermediate Similarity	NPD1243	Approved
0.7949	Intermediate Similarity	NPD5403	Approved
0.7935	Intermediate Similarity	NPD5401	Approved
0.7922	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1607	Approved
0.7914	Intermediate Similarity	NPD1247	Approved
0.7911	Intermediate Similarity	NPD4380	Phase 2
0.7908	Intermediate Similarity	NPD3750	Approved
0.7881	Intermediate Similarity	NPD2935	Discontinued
0.7853	Intermediate Similarity	NPD5494	Approved
0.7848	Intermediate Similarity	NPD3226	Approved
0.7834	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.7771	Intermediate Similarity	NPD1512	Approved
0.7765	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2801	Approved
0.7764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6832	Phase 2
0.773	Intermediate Similarity	NPD3749	Approved
0.773	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1471	Phase 3
0.7707	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1934	Approved
0.7697	Intermediate Similarity	NPD6959	Discontinued
0.7679	Intermediate Similarity	NPD3818	Discontinued
0.7669	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6166	Phase 2
0.7665	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5710	Approved
0.7651	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5711	Approved
0.7647	Intermediate Similarity	NPD6797	Phase 2
0.7643	Intermediate Similarity	NPD1511	Approved
0.7633	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2800	Approved
0.7607	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7251	Discontinued
0.7597	Intermediate Similarity	NPD2346	Discontinued
0.7582	Intermediate Similarity	NPD2799	Discontinued
0.7582	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6651	Approved
0.7561	Intermediate Similarity	NPD7768	Phase 2
0.7558	Intermediate Similarity	NPD7808	Phase 3
0.7544	Intermediate Similarity	NPD5953	Discontinued
0.7532	Intermediate Similarity	NPD1551	Phase 2
0.7529	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD230	Phase 1
0.7483	Intermediate Similarity	NPD1876	Approved
0.747	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD3972	Approved
0.7442	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1465	Phase 2
0.7427	Intermediate Similarity	NPD7054	Approved
0.7417	Intermediate Similarity	NPD2313	Discontinued
0.7396	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5242	Approved
0.7384	Intermediate Similarity	NPD7472	Approved
0.7384	Intermediate Similarity	NPD7074	Phase 3
0.7383	Intermediate Similarity	NPD1019	Discontinued
0.7372	Intermediate Similarity	NPD2344	Approved
0.7368	Intermediate Similarity	NPD3751	Discontinued
0.7353	Intermediate Similarity	NPD2403	Approved
0.7353	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4628	Phase 3
0.7326	Intermediate Similarity	NPD7286	Phase 2
0.732	Intermediate Similarity	NPD943	Approved
0.7312	Intermediate Similarity	NPD7390	Discontinued
0.731	Intermediate Similarity	NPD5691	Approved
0.7303	Intermediate Similarity	NPD1296	Phase 2
0.7299	Intermediate Similarity	NPD6559	Discontinued
0.7297	Intermediate Similarity	NPD7435	Discontinued
0.7289	Intermediate Similarity	NPD5353	Approved
0.7273	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD17	Approved
0.7235	Intermediate Similarity	NPD6808	Phase 2
0.7235	Intermediate Similarity	NPD3787	Discontinued
0.7235	Intermediate Similarity	NPD7229	Phase 3
0.7233	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD9717	Approved
0.7208	Intermediate Similarity	NPD2979	Phase 3
0.72	Intermediate Similarity	NPD3267	Approved
0.72	Intermediate Similarity	NPD3266	Approved
0.7191	Intermediate Similarity	NPD8434	Phase 2
0.7188	Intermediate Similarity	NPD2309	Approved
0.7188	Intermediate Similarity	NPD3887	Approved
0.7186	Intermediate Similarity	NPD4288	Approved
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.7162	Intermediate Similarity	NPD1281	Approved
0.7162	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD4626	Approved
0.7135	Intermediate Similarity	NPD6780	Approved
0.7135	Intermediate Similarity	NPD6781	Approved
0.7135	Intermediate Similarity	NPD6777	Approved
0.7135	Intermediate Similarity	NPD6776	Approved
0.7135	Intermediate Similarity	NPD6782	Approved
0.7135	Intermediate Similarity	NPD6779	Approved
0.7135	Intermediate Similarity	NPD6778	Approved
0.7123	Intermediate Similarity	NPD9545	Approved
0.7114	Intermediate Similarity	NPD1608	Approved
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6386	Approved
0.7108	Intermediate Similarity	NPD6385	Approved
0.7103	Intermediate Similarity	NPD9493	Approved
0.7097	Intermediate Similarity	NPD4307	Phase 2
0.7095	Intermediate Similarity	NPD8150	Discontinued
0.7089	Intermediate Similarity	NPD5405	Approved
0.7089	Intermediate Similarity	NPD6100	Approved
0.7089	Intermediate Similarity	NPD2438	Suspended
0.7089	Intermediate Similarity	NPD6099	Approved
0.7089	Intermediate Similarity	NPD5404	Approved
0.7089	Intermediate Similarity	NPD5408	Approved
0.7089	Intermediate Similarity	NPD5406	Approved
0.7086	Intermediate Similarity	NPD1203	Approved
0.7086	Intermediate Similarity	NPD1470	Approved
0.7081	Intermediate Similarity	NPD6190	Approved
0.7078	Intermediate Similarity	NPD411	Approved
0.7078	Intermediate Similarity	NPD3268	Approved
0.7078	Intermediate Similarity	NPD3764	Approved
0.7075	Intermediate Similarity	NPD1651	Approved
0.7068	Intermediate Similarity	NPD7874	Approved
0.7068	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6280	Approved
0.7066	Intermediate Similarity	NPD6279	Approved
0.7065	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6234	Discontinued
0.7051	Intermediate Similarity	NPD6355	Discontinued
0.7051	Intermediate Similarity	NPD1933	Approved
0.7047	Intermediate Similarity	NPD422	Phase 1
0.7044	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2353	Approved
0.7039	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7033	Discontinued
0.7022	Intermediate Similarity	NPD8313	Approved
0.7022	Intermediate Similarity	NPD8312	Approved
0.7021	Intermediate Similarity	NPD7697	Approved
0.7021	Intermediate Similarity	NPD7698	Approved
0.7021	Intermediate Similarity	NPD7696	Phase 3
0.7021	Intermediate Similarity	NPD2182	Approved
0.702	Intermediate Similarity	NPD1283	Approved
0.7019	Intermediate Similarity	NPD7003	Approved
0.7016	Intermediate Similarity	NPD8151	Discontinued
0.7014	Intermediate Similarity	NPD1241	Discontinued
0.6989	Remote Similarity	NPD8285	Discontinued
0.6988	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7458	Discontinued
0.6987	Remote Similarity	NPD4060	Phase 1
0.6986	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7870	Phase 2
0.6984	Remote Similarity	NPD7871	Phase 2
0.6974	Remote Similarity	NPD2797	Approved
0.6968	Remote Similarity	NPD6798	Discontinued
0.6966	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD9268	Approved
0.6951	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4308	Phase 3
0.6909	Remote Similarity	NPD6273	Approved
0.6905	Remote Similarity	NPD5889	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