NPASS Compound

Structure

CID270837 OpenBabel06191716072D 24 26 0 0 0 0 0 0 0 0999 V2000 0.8660 -1.5000 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 -3.4641 3.0000 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 -0.0000 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 -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 -3.4641 -1.0000 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 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 -1.7321 -1.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 -4.3301 -1.5000 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 3.0000 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 -3.4641 2.0000 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 4 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 19 1 0 0 0 0 10 24 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 20 2 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 16 17 2 0 0 0 0 16 21 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:	330.11
Volume:	328.501
LogP:	3.757
LogD:	2.972
LogS:	-4.119
# Rotatable Bonds:	4
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.713
Synthetic Accessibility Score:	2.791
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:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.831
MDCK Permeability:	1.1645836821116973e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.079
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.052

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	90.52650451660156%
Volume Distribution (VD):	0.866
Pgp-substrate:	13.036796569824219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.953
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.655
CYP2C19-substrate:	0.379
CYP2C9-inhibitor:	0.773
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.598
CYP2D6-substrate:	0.816
CYP3A4-inhibitor:	0.341
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	5.467
Half-life (T1/2):	0.719

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.395
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.618
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.291
Skin Sensitization:	0.592
Carcinogencity:	0.037
Eye Corrosion:	0.004
Eye Irritation:	0.639
Respiratory Toxicity:	0.284

Download Data

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

Natural Product: NPC270837

Natural Product ID:	NPC270837
*Common Name:**	6-Methoxycomaparvin
IUPAC Name:	5,8-dihydroxy-6,10-dimethoxy-2-propylbenzo[h]chromen-4-one
Synonyms:	6-Methoxycomaparvin
Standard InCHIKey:	IUFQFEBTSUUHDT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O6/c1-4-5-10-8-12(20)15-16(21)17(23-3)11-6-9(19)7-13(22-2)14(11)18(15)24-10/h6-8,19,21H,4-5H2,1-3H3
SMILES:	CCCc1cc(=O)c2c(c(c3cc(cc(c3c2o1)OC)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401565
PubChem CID:	13917259
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11087592]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15730242]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1593281]
NPO40837	Echinoderm comanthus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18088098]
NPO32950	crinoids	Class	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20627559]
NPO24269	Comatula rotalaria	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27063022]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30028612]
NPO24269	Comatula rotalaria	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32478519]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8676130]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8946743]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9113	Blainvillea acmella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5128	Auxarthron umbrinum	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9894	Brachyclados megalanthus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9003	Metarhizium flavoviride	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9113	Blainvillea acmella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24269	Comatula rotalaria	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9761	Pilocarpus riedelianus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8851	Cetraria canadensis	Species	Parmeliaceae	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	1
MIC	1
Others	3

Activity Type	# Activity
Individual Protein	2
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	Inhibition	=	27.5	%	PMID[528594]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	>	20000.0	nM	PMID[528594]
NPT2	Others	Unspecified		Activity	=	53.0	%	PMID[528593]
NPT2	Others	Unspecified		Activity	=	75.0	%	PMID[528593]
NPT2	Others	Unspecified		MIC	=	300000.0	nM	PMID[528593]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	100000.0	nM	PMID[528595]

☑ 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 NPC270837 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	457
0.1-0.2	2003
0.2-0.3	4591
0.3-0.4	11270
0.4-0.5	6575
0.5-0.6	3628
0.6-0.7	4989
0.7-0.8	5237
0.8-0.85	2215
0.85-0.9	1086
0.9-0.95	585
0.95-1	61

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC294965
0.987	High Similarity	NPC66288
0.9744	High Similarity	NPC236132
0.9677	High Similarity	NPC14353
0.9677	High Similarity	NPC228785
0.9677	High Similarity	NPC56085
0.962	High Similarity	NPC37870
0.9618	High Similarity	NPC197168
0.9615	High Similarity	NPC278052
0.9615	High Similarity	NPC61010
0.9615	High Similarity	NPC40491
0.9613	High Similarity	NPC100123
0.9557	High Similarity	NPC275780
0.9557	High Similarity	NPC472450
0.9557	High Similarity	NPC239752
0.9557	High Similarity	NPC25361
0.9551	High Similarity	NPC320359
0.9551	High Similarity	NPC119224
0.9548	High Similarity	NPC241904
0.9548	High Similarity	NPC165977
0.9548	High Similarity	NPC300727
0.9548	High Similarity	NPC217677
0.9497	High Similarity	NPC39091
0.9494	High Similarity	NPC220313
0.9494	High Similarity	NPC189473
0.9494	High Similarity	NPC236521
0.9494	High Similarity	NPC152659
0.9494	High Similarity	NPC248638
0.9494	High Similarity	NPC23298
0.9494	High Similarity	NPC7483
0.9494	High Similarity	NPC207690
0.9487	High Similarity	NPC476242
0.9484	High Similarity	NPC142339
0.9484	High Similarity	NPC274730
0.9441	High Similarity	NPC124470
0.9441	High Similarity	NPC109827
0.9434	High Similarity	NPC326520
0.943	High Similarity	NPC229632
0.943	High Similarity	NPC470694
0.943	High Similarity	NPC25152
0.9427	High Similarity	NPC84571
0.9427	High Similarity	NPC246478
0.9427	High Similarity	NPC476980
0.9427	High Similarity	NPC475886
0.9427	High Similarity	NPC474287
0.9423	High Similarity	NPC236796
0.9423	High Similarity	NPC36852
0.9423	High Similarity	NPC78225
0.9423	High Similarity	NPC262286
0.9416	High Similarity	NPC471982
0.9387	High Similarity	NPC227906
0.9383	High Similarity	NPC158226
0.9379	High Similarity	NPC476637
0.9379	High Similarity	NPC163130
0.9379	High Similarity	NPC165979
0.9375	High Similarity	NPC170245
0.9375	High Similarity	NPC43319
0.9375	High Similarity	NPC472449
0.9367	High Similarity	NPC474351
0.9367	High Similarity	NPC278427
0.9367	High Similarity	NPC474186
0.9367	High Similarity	NPC311740
0.9367	High Similarity	NPC32694
0.9367	High Similarity	NPC474187
0.9367	High Similarity	NPC475883
0.9367	High Similarity	NPC258331
0.9363	High Similarity	NPC85121
0.9359	High Similarity	NPC191146
0.9359	High Similarity	NPC138243
0.9359	High Similarity	NPC68093
0.9355	High Similarity	NPC176775
0.9355	High Similarity	NPC276409
0.9355	High Similarity	NPC183878
0.9355	High Similarity	NPC250822
0.9355	High Similarity	NPC231018
0.9355	High Similarity	NPC69394
0.9355	High Similarity	NPC75279
0.9355	High Similarity	NPC47781
0.9355	High Similarity	NPC160951
0.9355	High Similarity	NPC22519
0.9355	High Similarity	NPC255350
0.9355	High Similarity	NPC145379
0.9355	High Similarity	NPC89474
0.9355	High Similarity	NPC274327
0.9329	High Similarity	NPC216307
0.9317	High Similarity	NPC126204
0.9317	High Similarity	NPC477154
0.9317	High Similarity	NPC6588
0.9317	High Similarity	NPC117854
0.9317	High Similarity	NPC218226
0.9313	High Similarity	NPC303174
0.9308	High Similarity	NPC81679
0.9308	High Similarity	NPC329760
0.9308	High Similarity	NPC472448
0.9308	High Similarity	NPC83922
0.9304	High Similarity	NPC235018
0.9304	High Similarity	NPC139036
0.9304	High Similarity	NPC471973
0.9304	High Similarity	NPC200746
0.9304	High Similarity	NPC204290
0.9304	High Similarity	NPC45146
0.9304	High Similarity	NPC36217
0.9299	High Similarity	NPC136674
0.9299	High Similarity	NPC469584
0.9299	High Similarity	NPC476981
0.9299	High Similarity	NPC199463
0.9299	High Similarity	NPC223787
0.9299	High Similarity	NPC37543
0.9295	High Similarity	NPC113906
0.9295	High Similarity	NPC227325
0.9295	High Similarity	NPC134287
0.9295	High Similarity	NPC167815
0.9295	High Similarity	NPC128863
0.9295	High Similarity	NPC4455
0.9295	High Similarity	NPC50715
0.9295	High Similarity	NPC92659
0.9295	High Similarity	NPC20830
0.9295	High Similarity	NPC183597
0.9295	High Similarity	NPC163780
0.9295	High Similarity	NPC2476
0.9295	High Similarity	NPC201136
0.9295	High Similarity	NPC138360
0.9295	High Similarity	NPC280339
0.9295	High Similarity	NPC130589
0.9295	High Similarity	NPC208197
0.9295	High Similarity	NPC196439
0.9295	High Similarity	NPC213622
0.9295	High Similarity	NPC256612
0.9295	High Similarity	NPC146165
0.929	High Similarity	NPC188203
0.929	High Similarity	NPC156222
0.929	High Similarity	NPC83508
0.929	High Similarity	NPC162313
0.929	High Similarity	NPC293183
0.929	High Similarity	NPC256283
0.929	High Similarity	NPC275836
0.929	High Similarity	NPC131624
0.929	High Similarity	NPC57030
0.929	High Similarity	NPC249570
0.929	High Similarity	NPC100887
0.929	High Similarity	NPC25270
0.929	High Similarity	NPC198826
0.929	High Similarity	NPC187498
0.929	High Similarity	NPC239128
0.929	High Similarity	NPC241498
0.929	High Similarity	NPC71334
0.929	High Similarity	NPC120163
0.929	High Similarity	NPC222830
0.929	High Similarity	NPC212678
0.929	High Similarity	NPC301323
0.929	High Similarity	NPC275722
0.9259	High Similarity	NPC49487
0.9259	High Similarity	NPC99613
0.9255	High Similarity	NPC29160
0.925	High Similarity	NPC475985
0.925	High Similarity	NPC186686
0.925	High Similarity	NPC41301
0.925	High Similarity	NPC474350
0.925	High Similarity	NPC146134
0.925	High Similarity	NPC477689
0.925	High Similarity	NPC470459
0.925	High Similarity	NPC133065
0.9245	High Similarity	NPC259456
0.9245	High Similarity	NPC266314
0.9245	High Similarity	NPC167678
0.9245	High Similarity	NPC29876
0.9241	High Similarity	NPC45846
0.9241	High Similarity	NPC329091
0.9241	High Similarity	NPC235448
0.9241	High Similarity	NPC474290
0.9241	High Similarity	NPC95936
0.9241	High Similarity	NPC250214
0.9236	High Similarity	NPC472455
0.9236	High Similarity	NPC474520
0.9236	High Similarity	NPC14561
0.9236	High Similarity	NPC77807
0.9236	High Similarity	NPC5379
0.9236	High Similarity	NPC49824
0.9236	High Similarity	NPC475799
0.9236	High Similarity	NPC13779
0.9231	High Similarity	NPC93552
0.9231	High Similarity	NPC280937
0.9231	High Similarity	NPC476631
0.9226	High Similarity	NPC208043
0.9226	High Similarity	NPC226973
0.9226	High Similarity	NPC202157
0.9221	High Similarity	NPC328119
0.9221	High Similarity	NPC177298
0.9221	High Similarity	NPC48479
0.9221	High Similarity	NPC158338
0.9221	High Similarity	NPC65589
0.9221	High Similarity	NPC100985
0.9221	High Similarity	NPC97029
0.9221	High Similarity	NPC97028
0.9221	High Similarity	NPC288036
0.9202	High Similarity	NPC101107
0.9198	High Similarity	NPC234331
0.9198	High Similarity	NPC474024
0.9193	High Similarity	NPC156432
0.9193	High Similarity	NPC473286

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 NPC270837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	428
0.1-0.2	1017
0.2-0.3	1856
0.3-0.4	2713
0.4-0.5	1703
0.5-0.6	902
0.6-0.7	357
0.7-0.8	136
0.8-0.85	21
0.85-0.9	15
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9355	High Similarity	NPD2801	Approved
0.8987	High Similarity	NPD2393	Clinical (unspecified phase)
0.8951	High Similarity	NPD6232	Discontinued
0.8924	High Similarity	NPD1934	Approved
0.8902	High Similarity	NPD7473	Discontinued
0.8774	High Similarity	NPD1511	Approved
0.8683	High Similarity	NPD5844	Phase 1
0.8662	High Similarity	NPD1512	Approved
0.8642	High Similarity	NPD3882	Suspended
0.8599	High Similarity	NPD4378	Clinical (unspecified phase)
0.8598	High Similarity	NPD5494	Approved
0.8545	High Similarity	NPD6959	Discontinued
0.8512	High Similarity	NPD3818	Discontinued
0.8503	High Similarity	NPD6167	Clinical (unspecified phase)
0.8503	High Similarity	NPD6168	Clinical (unspecified phase)
0.8503	High Similarity	NPD6166	Phase 2
0.8466	Intermediate Similarity	NPD3817	Phase 2
0.8405	Intermediate Similarity	NPD1465	Phase 2
0.8372	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD7054	Approved
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8304	Intermediate Similarity	NPD7472	Approved
0.8304	Intermediate Similarity	NPD7074	Phase 3
0.8303	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7819	Suspended
0.825	Intermediate Similarity	NPD2532	Approved
0.825	Intermediate Similarity	NPD2534	Approved
0.825	Intermediate Similarity	NPD2533	Approved
0.8214	Intermediate Similarity	NPD1247	Approved
0.8192	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6797	Phase 2
0.8144	Intermediate Similarity	NPD7075	Discontinued
0.8137	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7808	Phase 3
0.8038	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1510	Phase 2
0.8024	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1607	Approved
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD1549	Phase 2
0.7975	Intermediate Similarity	NPD2796	Approved
0.7963	Intermediate Similarity	NPD7390	Discontinued
0.7939	Intermediate Similarity	NPD3226	Approved
0.7937	Intermediate Similarity	NPD2800	Approved
0.7931	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5402	Approved
0.7907	Intermediate Similarity	NPD3926	Phase 2
0.7888	Intermediate Similarity	NPD3750	Approved
0.7885	Intermediate Similarity	NPD943	Approved
0.7885	Intermediate Similarity	NPD1240	Approved
0.7882	Intermediate Similarity	NPD6234	Discontinued
0.7882	Intermediate Similarity	NPD919	Approved
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7853	Intermediate Similarity	NPD6799	Approved
0.7844	Intermediate Similarity	NPD7411	Suspended
0.7841	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3749	Approved
0.7812	Intermediate Similarity	NPD2346	Discontinued
0.7805	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7768	Phase 2
0.7759	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6099	Approved
0.775	Intermediate Similarity	NPD6100	Approved
0.7701	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD37	Approved
0.7688	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4967	Phase 2
0.7661	Intermediate Similarity	NPD4966	Approved
0.7661	Intermediate Similarity	NPD4965	Approved
0.7644	Intermediate Similarity	NPD5710	Approved
0.7644	Intermediate Similarity	NPD5711	Approved
0.7628	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD230	Phase 1
0.7607	Intermediate Similarity	NPD1243	Approved
0.7605	Intermediate Similarity	NPD920	Approved
0.7586	Intermediate Similarity	NPD7199	Phase 2
0.758	Intermediate Similarity	NPD4625	Phase 3
0.7578	Intermediate Similarity	NPD3748	Approved
0.7571	Intermediate Similarity	NPD7228	Approved
0.7571	Intermediate Similarity	NPD3751	Discontinued
0.7561	Intermediate Similarity	NPD4628	Phase 3
0.7547	Intermediate Similarity	NPD1613	Approved
0.7547	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD3787	Discontinued
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.7527	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.7513	Intermediate Similarity	NPD6782	Approved
0.7513	Intermediate Similarity	NPD6777	Approved
0.7513	Intermediate Similarity	NPD6776	Approved
0.7513	Intermediate Similarity	NPD6779	Approved
0.7513	Intermediate Similarity	NPD6778	Approved
0.7513	Intermediate Similarity	NPD6780	Approved
0.7513	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.7485	Intermediate Similarity	NPD2344	Approved
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8151	Discontinued
0.7469	Intermediate Similarity	NPD2799	Discontinued
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7459	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6651	Approved
0.7421	Intermediate Similarity	NPD2313	Discontinued
0.7398	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7783	Phase 2
0.7396	Intermediate Similarity	NPD7435	Discontinued
0.7391	Intermediate Similarity	NPD8150	Discontinued
0.7381	Intermediate Similarity	NPD5401	Approved
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1653	Approved
0.7348	Intermediate Similarity	NPD5953	Discontinued
0.7345	Intermediate Similarity	NPD7229	Phase 3
0.7333	Intermediate Similarity	NPD7286	Phase 2
0.7321	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5404	Approved
0.7317	Intermediate Similarity	NPD5406	Approved
0.7317	Intermediate Similarity	NPD5405	Approved
0.7317	Intermediate Similarity	NPD5408	Approved
0.7312	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7697	Approved
0.7306	Intermediate Similarity	NPD7698	Approved
0.7306	Intermediate Similarity	NPD7696	Phase 3
0.7305	Intermediate Similarity	NPD2309	Approved
0.7297	Intermediate Similarity	NPD8434	Phase 2
0.7268	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD7871	Phase 2
0.7254	Intermediate Similarity	NPD6823	Phase 2
0.7249	Intermediate Similarity	NPD6534	Approved
0.7249	Intermediate Similarity	NPD6535	Approved
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7701	Phase 2
0.7233	Intermediate Similarity	NPD9494	Approved
0.7215	Intermediate Similarity	NPD1470	Approved
0.7205	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6190	Approved
0.7197	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1201	Approved
0.7178	Intermediate Similarity	NPD1933	Approved
0.7176	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7874	Approved
0.7172	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4360	Phase 2
0.7158	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD7003	Approved
0.7136	Intermediate Similarity	NPD7801	Approved
0.7135	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7685	Pre-registration
0.712	Intermediate Similarity	NPD7240	Approved
0.7117	Intermediate Similarity	NPD4060	Phase 1
0.7111	Intermediate Similarity	NPD5242	Approved
0.711	Intermediate Similarity	NPD7458	Discontinued
0.7099	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3268	Approved
0.7097	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1651	Approved
0.7089	Intermediate Similarity	NPD4749	Approved
0.7088	Intermediate Similarity	NPD7177	Discontinued
0.7083	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6674	Discontinued
0.7081	Intermediate Similarity	NPD4908	Phase 1
0.7072	Intermediate Similarity	NPD2403	Approved
0.7066	Intermediate Similarity	NPD1471	Phase 3
0.7063	Intermediate Similarity	NPD2798	Approved
0.7048	Intermediate Similarity	NPD4308	Phase 3
0.7044	Intermediate Similarity	NPD1283	Approved
0.7035	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4361	Phase 2
0.7031	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9269	Phase 2
0.7016	Intermediate Similarity	NPD6213	Phase 3
0.7016	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6212	Phase 3
0.7006	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD1203	Approved
0.7	Intermediate Similarity	NPD2797	Approved
0.6994	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7907	Approved
0.6989	Remote Similarity	NPD6844	Discontinued
0.6976	Remote Similarity	NPD4665	Approved
0.6976	Remote Similarity	NPD4111	Phase 1
0.6962	Remote Similarity	NPD1610	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