NPASS Compound

Structure

NPC158226 OpenBabel07101719242D 28 30 0 0 0 0 0 0 0 0999 V2000 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 -1.7321 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 0.8660 -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 1.7321 0.0000 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 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 1.7321 1.0000 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 -1.7321 -0.0000 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 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 26 1 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 9 21 2 0 0 0 0 9 27 1 0 0 0 0 10 22 2 0 0 0 0 10 28 1 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 15 20 2 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 23 2 0 0 0 0 19 24 2 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.08
Volume:	372.764
LogP:	3.255
LogD:	2.169
LogS:	-5.49
# Rotatable Bonds:	5
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.54
Synthetic Accessibility Score:	2.568
Fsp3:	0.2
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:	-5.051
MDCK Permeability:	4.341425665188581e-05
Pgp-inhibitor:	0.809
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.172
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.081

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	90.80167388916016%
Volume Distribution (VD):	0.979
Pgp-substrate:	12.974574089050293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.509
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.11
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.688
CYP2C9-substrate:	0.306
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.362
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	1.943
Half-life (T1/2):	0.413

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.016
Drug-inuced Liver Injury (DILI):	0.881
AMES Toxicity:	0.714
Rat Oral Acute Toxicity:	0.679
Maximum Recommended Daily Dose:	0.635
Skin Sensitization:	0.203
Carcinogencity:	0.344
Eye Corrosion:	0.004
Eye Irritation:	0.81
Respiratory Toxicity:	0.167

Download Data

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

Natural Product: NPC158226

Natural Product ID:	NPC158226
*Common Name:**	3,5-Diacetoxy-8-Hydroxy-7-Methoxy-2-Methylanthracene-9,10-Dione
IUPAC Name:	(8-acetyloxy-5-hydroxy-6-methoxy-3-methyl-9,10-dioxoanthracen-2-yl) acetate
Synonyms:
Standard InCHIKey:	ILZLWCFVHZUCLY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O8/c1-8-5-11-12(6-13(8)27-9(2)21)18(23)16-14(28-10(3)22)7-15(26-4)20(25)17(16)19(11)24/h5-7,25H,1-4H3
SMILES:	Cc1cc2c(cc1OC(=O)C)C(=O)c1c(cc(c(c1C2=O)O)OC)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047325
PubChem CID:	59052034
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO33050	nigrospora sp.	Species	Trichosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22545792]

☑ 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
MIC	9

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50000.0	nM	PMID[564193]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	200000.0	nM	PMID[564193]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	200000.0	nM	PMID[564193]
NPT5776	Organism	Streptomyces albus	Streptomyces albus	MIC	=	50000.0	nM	PMID[564193]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	200000.0	nM	PMID[564193]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	>	200000.0	nM	PMID[564193]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	200000.0	nM	PMID[564193]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	>	200000.0	nM	PMID[564193]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	>	200000.0	nM	PMID[564193]

☑ 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 NPC158226 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	411
0.1-0.2	1828
0.2-0.3	4347
0.3-0.4	9563
0.4-0.5	8353
0.5-0.6	3559
0.6-0.7	5026
0.7-0.8	5786
0.8-0.85	2529
0.85-0.9	1168
0.9-0.95	114
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC99613
0.9875	High Similarity	NPC49487
0.9875	High Similarity	NPC163130
0.9875	High Similarity	NPC165979
0.975	High Similarity	NPC29160
0.9691	High Similarity	NPC109827
0.9691	High Similarity	NPC124470
0.9689	High Similarity	NPC234331
0.9563	High Similarity	NPC108767
0.9503	High Similarity	NPC474350
0.9437	High Similarity	NPC84571
0.9398	High Similarity	NPC139350
0.9383	High Similarity	NPC270837
0.9383	High Similarity	NPC236132
0.9383	High Similarity	NPC300984
0.9379	High Similarity	NPC311740
0.9345	High Similarity	NPC113446
0.9321	High Similarity	NPC294965
0.9317	High Similarity	NPC14353
0.9317	High Similarity	NPC56085
0.9317	High Similarity	NPC228785
0.9313	High Similarity	NPC199463
0.9313	High Similarity	NPC37543
0.9286	High Similarity	NPC207467
0.9268	High Similarity	NPC20216
0.9264	High Similarity	NPC156082
0.9259	High Similarity	NPC61010
0.9259	High Similarity	NPC278052
0.9259	High Similarity	NPC40491
0.9259	High Similarity	NPC303565
0.9259	High Similarity	NPC66288
0.9255	High Similarity	NPC100123
0.9255	High Similarity	NPC45846
0.925	High Similarity	NPC77807
0.925	High Similarity	NPC54928
0.925	High Similarity	NPC14561
0.925	High Similarity	NPC5379
0.9231	High Similarity	NPC473785
0.9222	High Similarity	NPC181523
0.9217	High Similarity	NPC1827
0.9217	High Similarity	NPC246716
0.9217	High Similarity	NPC239440
0.9217	High Similarity	NPC20543
0.9217	High Similarity	NPC10576
0.9217	High Similarity	NPC17219
0.9207	High Similarity	NPC8070
0.9207	High Similarity	NPC112981
0.9202	High Similarity	NPC470694
0.9198	High Similarity	NPC320359
0.9198	High Similarity	NPC119224
0.9193	High Similarity	NPC241904
0.9193	High Similarity	NPC165977
0.9193	High Similarity	NPC262286
0.9193	High Similarity	NPC300727
0.9193	High Similarity	NPC36852
0.9193	High Similarity	NPC178976
0.9193	High Similarity	NPC217677
0.9191	High Similarity	NPC295436
0.9176	High Similarity	NPC265795
0.9167	High Similarity	NPC289147
0.9167	High Similarity	NPC245975
0.9157	High Similarity	NPC26568
0.9152	High Similarity	NPC37870
0.9146	High Similarity	NPC220313
0.9146	High Similarity	NPC477689
0.9146	High Similarity	NPC236521
0.9146	High Similarity	NPC152659
0.9146	High Similarity	NPC248638
0.9146	High Similarity	NPC197168
0.9146	High Similarity	NPC7483
0.9136	High Similarity	NPC83763
0.9136	High Similarity	NPC476242
0.9136	High Similarity	NPC168616
0.9136	High Similarity	NPC238381
0.913	High Similarity	NPC274730
0.913	High Similarity	NPC146211
0.913	High Similarity	NPC142339
0.913	High Similarity	NPC138243
0.9125	High Similarity	NPC107109
0.9118	High Similarity	NPC212290
0.9096	High Similarity	NPC272485
0.9096	High Similarity	NPC292788
0.9096	High Similarity	NPC76647
0.9091	High Similarity	NPC326520
0.9091	High Similarity	NPC267153
0.9091	High Similarity	NPC25361
0.9091	High Similarity	NPC472450
0.9091	High Similarity	NPC275780
0.9091	High Similarity	NPC239752
0.9091	High Similarity	NPC26386
0.9085	High Similarity	NPC93739
0.9085	High Similarity	NPC25152
0.9085	High Similarity	NPC144843
0.908	High Similarity	NPC476980
0.908	High Similarity	NPC474287
0.908	High Similarity	NPC475886
0.9075	High Similarity	NPC174486
0.9074	High Similarity	NPC78225
0.9074	High Similarity	NPC236796
0.9068	High Similarity	NPC113906
0.9068	High Similarity	NPC208197
0.9062	High Similarity	NPC289968
0.9059	High Similarity	NPC297807
0.9042	High Similarity	NPC280493
0.9036	High Similarity	NPC30027
0.9036	High Similarity	NPC39091
0.9036	High Similarity	NPC472452
0.9036	High Similarity	NPC170245
0.903	High Similarity	NPC284007
0.903	High Similarity	NPC234004
0.903	High Similarity	NPC189473
0.903	High Similarity	NPC207690
0.903	High Similarity	NPC41301
0.903	High Similarity	NPC23298
0.9024	High Similarity	NPC266314
0.9024	High Similarity	NPC474187
0.9024	High Similarity	NPC474186
0.9024	High Similarity	NPC474351
0.9024	High Similarity	NPC475883
0.9024	High Similarity	NPC258331
0.9024	High Similarity	NPC32694
0.9018	High Similarity	NPC85121
0.9012	High Similarity	NPC191146
0.9012	High Similarity	NPC68093
0.9006	High Similarity	NPC75279
0.9006	High Similarity	NPC89474
0.9006	High Similarity	NPC250822
0.9006	High Similarity	NPC276409
0.9006	High Similarity	NPC475895
0.9	High Similarity	NPC216307
0.8994	High Similarity	NPC37606
0.8994	High Similarity	NPC261471
0.8988	High Similarity	NPC218533
0.8988	High Similarity	NPC78830
0.8982	High Similarity	NPC107009
0.8982	High Similarity	NPC477154
0.8982	High Similarity	NPC117854
0.8982	High Similarity	NPC474024
0.8982	High Similarity	NPC6588
0.8976	High Similarity	NPC303174
0.897	High Similarity	NPC81679
0.897	High Similarity	NPC8300
0.897	High Similarity	NPC472448
0.897	High Similarity	NPC329760
0.897	High Similarity	NPC229632
0.897	High Similarity	NPC83922
0.8966	High Similarity	NPC105591
0.8963	High Similarity	NPC143050
0.8963	High Similarity	NPC235018
0.8963	High Similarity	NPC130955
0.8963	High Similarity	NPC45146
0.8963	High Similarity	NPC246478
0.8963	High Similarity	NPC200746
0.8963	High Similarity	NPC47623
0.8963	High Similarity	NPC36217
0.8957	High Similarity	NPC469584
0.8957	High Similarity	NPC136674
0.8957	High Similarity	NPC35598
0.8957	High Similarity	NPC78103
0.8957	High Similarity	NPC476981
0.8957	High Similarity	NPC223787
0.8957	High Similarity	NPC263483
0.8957	High Similarity	NPC222689
0.8953	High Similarity	NPC208069
0.8951	High Similarity	NPC168247
0.8951	High Similarity	NPC50715
0.8951	High Similarity	NPC183597
0.8951	High Similarity	NPC20541
0.8951	High Similarity	NPC2476
0.8951	High Similarity	NPC128863
0.8951	High Similarity	NPC152951
0.8951	High Similarity	NPC227325
0.8951	High Similarity	NPC163780
0.8951	High Similarity	NPC117992
0.8951	High Similarity	NPC201136
0.8951	High Similarity	NPC134287
0.8951	High Similarity	NPC471800
0.8951	High Similarity	NPC196439
0.8951	High Similarity	NPC92659
0.8951	High Similarity	NPC167815
0.8951	High Similarity	NPC146165
0.8951	High Similarity	NPC4455
0.8951	High Similarity	NPC130589
0.8951	High Similarity	NPC256612
0.8951	High Similarity	NPC20830
0.8951	High Similarity	NPC57674
0.8951	High Similarity	NPC138360
0.8951	High Similarity	NPC280339
0.8951	High Similarity	NPC230149
0.8947	High Similarity	NPC98546
0.8944	High Similarity	NPC149889
0.8944	High Similarity	NPC101996
0.8944	High Similarity	NPC40356
0.8944	High Similarity	NPC312338
0.8944	High Similarity	NPC154683
0.8944	High Similarity	NPC471982
0.8941	High Similarity	NPC68381
0.8941	High Similarity	NPC146803
0.8938	High Similarity	NPC294646
0.8938	High Similarity	NPC473466

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 NPC158226 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	1012
0.2-0.3	1948
0.3-0.4	2597
0.4-0.5	1743
0.5-0.6	890
0.6-0.7	389
0.7-0.8	156
0.8-0.85	27
0.85-0.9	11
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9202	High Similarity	NPD6232	Discontinued
0.9152	High Similarity	NPD7473	Discontinued
0.8929	High Similarity	NPD5844	Phase 1
0.8889	High Similarity	NPD2801	Approved
0.8667	High Similarity	NPD4868	Clinical (unspecified phase)
0.8659	High Similarity	NPD2393	Clinical (unspecified phase)
0.8659	High Similarity	NPD1465	Phase 2
0.8598	High Similarity	NPD1934	Approved
0.8545	High Similarity	NPD7819	Suspended
0.8531	High Similarity	NPD8397	Clinical (unspecified phase)
0.8528	High Similarity	NPD3226	Approved
0.8494	Intermediate Similarity	NPD3817	Phase 2
0.8443	Intermediate Similarity	NPD3882	Suspended
0.843	Intermediate Similarity	NPD3818	Discontinued
0.8421	Intermediate Similarity	NPD6166	Phase 2
0.8421	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD5494	Approved
0.84	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD7075	Discontinued
0.8353	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD1511	Approved
0.8282	Intermediate Similarity	NPD2533	Approved
0.8282	Intermediate Similarity	NPD2534	Approved
0.8282	Intermediate Similarity	NPD2532	Approved
0.8232	Intermediate Similarity	NPD1512	Approved
0.8232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD7074	Phase 3
0.8214	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7411	Suspended
0.8182	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7054	Approved
0.8171	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6801	Discontinued
0.8144	Intermediate Similarity	NPD4380	Phase 2
0.8144	Intermediate Similarity	NPD6599	Discontinued
0.8129	Intermediate Similarity	NPD6234	Discontinued
0.8125	Intermediate Similarity	NPD7472	Approved
0.807	Intermediate Similarity	NPD3749	Approved
0.8063	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD5402	Approved
0.8034	Intermediate Similarity	NPD6559	Discontinued
0.8025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6799	Approved
0.7978	Intermediate Similarity	NPD6797	Phase 2
0.7965	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD2346	Discontinued
0.7953	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD37	Approved
0.7933	Intermediate Similarity	NPD7251	Discontinued
0.7927	Intermediate Similarity	NPD3750	Approved
0.7919	Intermediate Similarity	NPD919	Approved
0.7907	Intermediate Similarity	NPD4967	Phase 2
0.7907	Intermediate Similarity	NPD4966	Approved
0.7907	Intermediate Similarity	NPD7768	Phase 2
0.7907	Intermediate Similarity	NPD4965	Approved
0.7889	Intermediate Similarity	NPD7808	Phase 3
0.7857	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD8313	Approved
0.7845	Intermediate Similarity	NPD8312	Approved
0.7841	Intermediate Similarity	NPD3926	Phase 2
0.7829	Intermediate Similarity	NPD1247	Approved
0.7829	Intermediate Similarity	NPD7199	Phase 2
0.7826	Intermediate Similarity	NPD1607	Approved
0.7809	Intermediate Similarity	NPD7228	Approved
0.7805	Intermediate Similarity	NPD1549	Phase 2
0.7801	Intermediate Similarity	NPD7435	Discontinued
0.7784	Intermediate Similarity	NPD7390	Discontinued
0.7784	Intermediate Similarity	NPD8151	Discontinued
0.7765	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD230	Phase 1
0.7764	Intermediate Similarity	NPD447	Suspended
0.7758	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD6777	Approved
0.7737	Intermediate Similarity	NPD6778	Approved
0.7737	Intermediate Similarity	NPD6779	Approved
0.7737	Intermediate Similarity	NPD6780	Approved
0.7737	Intermediate Similarity	NPD6782	Approved
0.7737	Intermediate Similarity	NPD6781	Approved
0.7737	Intermediate Similarity	NPD6776	Approved
0.773	Intermediate Similarity	NPD1510	Phase 2
0.7717	Intermediate Similarity	NPD8150	Discontinued
0.7711	Intermediate Similarity	NPD4628	Phase 3
0.7702	Intermediate Similarity	NPD943	Approved
0.7702	Intermediate Similarity	NPD1240	Approved
0.7684	Intermediate Similarity	NPD5710	Approved
0.7684	Intermediate Similarity	NPD5711	Approved
0.7683	Intermediate Similarity	NPD2796	Approved
0.7683	Intermediate Similarity	NPD1551	Phase 2
0.768	Intermediate Similarity	NPD5953	Discontinued
0.7651	Intermediate Similarity	NPD2800	Approved
0.7651	Intermediate Similarity	NPD1243	Approved
0.7647	Intermediate Similarity	NPD5403	Approved
0.7647	Intermediate Similarity	NPD920	Approved
0.7644	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3748	Approved
0.7622	Intermediate Similarity	NPD2799	Discontinued
0.7622	Intermediate Similarity	NPD8434	Phase 2
0.7614	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7783	Phase 2
0.7611	Intermediate Similarity	NPD3751	Discontinued
0.7605	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD1653	Approved
0.7563	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7874	Approved
0.756	Intermediate Similarity	NPD6190	Approved
0.7529	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5401	Approved
0.7526	Intermediate Similarity	NPD7696	Phase 3
0.7526	Intermediate Similarity	NPD7697	Approved
0.7526	Intermediate Similarity	NPD7698	Approved
0.7515	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD6535	Approved
0.7474	Intermediate Similarity	NPD6534	Approved
0.7473	Intermediate Similarity	NPD7286	Phase 2
0.7471	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5405	Approved
0.747	Intermediate Similarity	NPD5404	Approved
0.747	Intermediate Similarity	NPD5406	Approved
0.747	Intermediate Similarity	NPD6100	Approved
0.747	Intermediate Similarity	NPD5408	Approved
0.747	Intermediate Similarity	NPD6099	Approved
0.7469	Intermediate Similarity	NPD2313	Discontinued
0.7462	Intermediate Similarity	NPD7701	Phase 2
0.7457	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7229	Phase 3
0.7389	Intermediate Similarity	NPD3787	Discontinued
0.7385	Intermediate Similarity	NPD6823	Phase 2
0.7362	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7700	Phase 2
0.7358	Intermediate Similarity	NPD7699	Phase 2
0.7356	Intermediate Similarity	NPD7458	Discontinued
0.7351	Intermediate Similarity	NPD7240	Approved
0.735	Intermediate Similarity	NPD7801	Approved
0.7346	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1933	Approved
0.7333	Intermediate Similarity	NPD8127	Discontinued
0.7321	Intermediate Similarity	NPD2344	Approved
0.7306	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7003	Approved
0.7289	Intermediate Similarity	NPD6651	Approved
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD1203	Approved
0.7267	Intermediate Similarity	NPD1470	Approved
0.7258	Intermediate Similarity	NPD7685	Pre-registration
0.7256	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5242	Approved
0.724	Intermediate Similarity	NPD6212	Phase 3
0.724	Intermediate Similarity	NPD6213	Phase 3
0.724	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6832	Phase 2
0.7234	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD8285	Discontinued
0.7228	Intermediate Similarity	NPD7177	Discontinued
0.7225	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8319	Approved
0.7222	Intermediate Similarity	NPD8320	Phase 1
0.7202	Intermediate Similarity	NPD4308	Phase 3
0.7198	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3027	Phase 3
0.7195	Intermediate Similarity	NPD4625	Phase 3
0.7188	Intermediate Similarity	NPD9269	Phase 2
0.7184	Intermediate Similarity	NPD6273	Approved
0.7173	Intermediate Similarity	NPD4287	Approved
0.7169	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD3764	Approved
0.7152	Intermediate Similarity	NPD411	Approved
0.7151	Intermediate Similarity	NPD2309	Approved
0.7128	Intermediate Similarity	NPD7549	Discontinued
0.7128	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8166	Discontinued
0.7086	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD9717	Approved
0.7074	Intermediate Similarity	NPD7038	Approved
0.7074	Intermediate Similarity	NPD7039	Approved
0.7073	Intermediate Similarity	NPD9494	Approved
0.7056	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4288	Approved
0.7056	Intermediate Similarity	NPD5353	Approved
0.7055	Intermediate Similarity	NPD2797	Approved
0.7048	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6674	Discontinued

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