NPASS Compound

Structure

CID315275 OpenBabel06191716132D 21 23 0 0 1 0 0 0 0 0999 V2000 -5.1962 -2.0000 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 -4.3301 -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 -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 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 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 1 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 2 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -1.7321 -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 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 5 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 5 1 0 0 0 0 3 8 2 0 0 0 0 4 7 1 0 0 0 0 4 9 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 1 0 0 0 10 14 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 18 2 0 0 0 0 13 15 1 0 0 0 0 13 19 1 1 0 0 0 14 20 2 0 0 0 0 15 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.08
Volume:	279.249
LogP:	1.356
LogD:	0.466
LogS:	-2.752
# Rotatable Bonds:	0
TPSA:	118.22
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	3.856
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.464
MDCK Permeability:	3.34E-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.913
Human Intestinal Absorption (HIA):	0.457
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.63

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	94.29%
Volume Distribution (VD):	0.687
Pgp-substrate:	6.64%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.353
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.166
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.607
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	4.888
Half-life (T1/2):	0.93

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.795
AMES Toxicity:	0.617
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.818
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.124
Respiratory Toxicity:	0.064

Download Data

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

Natural Product: NPC315275

Natural Product ID:	NPC315275
*Common Name:**	Pleosporone
IUPAC Name:	(1R,2S,3S)-1,2,3,8-tetrahydroxy-6-methyl-1,2,3,4-tetrahydroanthracene-9,10-dione
Synonyms:	Pleosporone
Standard InCHIKey:	YUSJPHSHLVVZRA-DYQSUWPFSA-N
Standard InCHI:	InChI=1S/C15H14O6/c1-5-2-6-10(8(16)3-5)14(20)11-7(12(6)18)4-9(17)13(19)15(11)21/h2-3,9,13,15-17,19,21H,4H2,1H3/t9-,13-,15+/m0/s1
SMILES:	Cc1cc2c(c(c1)O)C(=O)C1=C(C[C@@H]([C@@H]([C@@H]1O)O)O)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492618
PubChem CID:	42636900
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO30531	Pleospora	Genus	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18442914]
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18570471]
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276650]
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	isolated from living stems and leaves of a Sedum sp.	Motilleja, Albacete, Spain	n.a.	PMID[23259972]

☑ 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	5
MIC	11
Others	10

Activity Type	# Activity
Cell Line	1
Organism	25

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	0.23	ug.mL-1	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	6.0	ug.mL-1	PMID[529397]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	21.8	mm	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	19.2	mm	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	9.0	mm	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	31.25	ug ml-1	PMID[529398]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	1.0	ug.mL-1	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	1.3	ug.mL-1	PMID[529398]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	Activity	=	80.0	%	PMID[529398]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	4.0	ug.mL-1	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	80.0	%	PMID[529398]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	8.0	ug.mL-1	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	8.4	ug.mL-1	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	15.4	ug.mL-1	PMID[529398]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	16.0	ug.mL-1	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[529398]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	64.0	ug.mL-1	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	64.0	ug.mL-1	PMID[529398]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64.0	ug.mL-1	PMID[529398]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	64.0	ug.mL-1	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Ratio IC50	=	6.0	n.a.	PMID[529398]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC80	=	4.0	ug.mL-1	PMID[529398]

☑ 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 NPC315275 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	330
0.1-0.2	1246
0.2-0.3	3057
0.3-0.4	7713
0.4-0.5	11618
0.5-0.6	5341
0.6-0.7	8289
0.7-0.8	4476
0.8-0.85	489
0.85-0.9	130
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9137	High Similarity	NPC244691
0.9058	High Similarity	NPC305845
0.9058	High Similarity	NPC204045
0.9007	High Similarity	NPC136878
0.8993	High Similarity	NPC135524
0.8955	High Similarity	NPC70622
0.8913	High Similarity	NPC190457
0.8905	High Similarity	NPC305060
0.8889	High Similarity	NPC52407
0.8889	High Similarity	NPC314048
0.8865	High Similarity	NPC471906
0.8865	High Similarity	NPC29932
0.8841	High Similarity	NPC416
0.8841	High Similarity	NPC61398
0.8832	High Similarity	NPC254847
0.8832	High Similarity	NPC86524
0.8824	High Similarity	NPC50924
0.8815	High Similarity	NPC110609
0.8815	High Similarity	NPC242358
0.8815	High Similarity	NPC246693
0.8815	High Similarity	NPC309430
0.8806	High Similarity	NPC136588
0.8806	High Similarity	NPC31799
0.8806	High Similarity	NPC199253
0.8797	High Similarity	NPC767
0.8797	High Similarity	NPC282923
0.8797	High Similarity	NPC247250
0.8788	High Similarity	NPC231774
0.8788	High Similarity	NPC3224
0.8779	High Similarity	NPC68756
0.8779	High Similarity	NPC152525
0.8769	High Similarity	NPC307174
0.8768	High Similarity	NPC53414
0.8768	High Similarity	NPC471905
0.8768	High Similarity	NPC53206
0.8741	High Similarity	NPC17083
0.8741	High Similarity	NPC93015
0.8732	High Similarity	NPC79627
0.8732	High Similarity	NPC48762
0.8731	High Similarity	NPC146647
0.8731	High Similarity	NPC278928
0.8731	High Similarity	NPC34414
0.8731	High Similarity	NPC99731
0.8723	High Similarity	NPC474961
0.8705	High Similarity	NPC173980
0.8699	High Similarity	NPC46882
0.8699	High Similarity	NPC132990
0.8676	High Similarity	NPC17843
0.8676	High Similarity	NPC58685
0.8671	High Similarity	NPC34482
0.8667	High Similarity	NPC198305
0.8667	High Similarity	NPC117609
0.8643	High Similarity	NPC138099
0.8643	High Similarity	NPC242994
0.8643	High Similarity	NPC143438
0.8633	High Similarity	NPC471452
0.8623	High Similarity	NPC283088
0.8623	High Similarity	NPC258502
0.8613	High Similarity	NPC53896
0.8613	High Similarity	NPC254603
0.8613	High Similarity	NPC267205
0.8611	High Similarity	NPC285122
0.8611	High Similarity	NPC470570
0.8603	High Similarity	NPC244699
0.8603	High Similarity	NPC205992
0.8601	High Similarity	NPC103910
0.8601	High Similarity	NPC193703
0.8601	High Similarity	NPC21599
0.8592	High Similarity	NPC73061
0.8592	High Similarity	NPC469520
0.8591	High Similarity	NPC478027
0.8582	High Similarity	NPC181560
0.8582	High Similarity	NPC156872
0.8582	High Similarity	NPC169452
0.8581	High Similarity	NPC155686
0.8571	High Similarity	NPC13715
0.8571	High Similarity	NPC61590
0.8571	High Similarity	NPC103540
0.8551	High Similarity	NPC474519
0.8551	High Similarity	NPC44437
0.8551	High Similarity	NPC12070
0.8542	High Similarity	NPC474630
0.8542	High Similarity	NPC170055
0.8538	High Similarity	NPC206778
0.8538	High Similarity	NPC285829
0.8531	High Similarity	NPC143898
0.8529	High Similarity	NPC62219
0.8529	High Similarity	NPC55949
0.8529	High Similarity	NPC147757
0.8521	High Similarity	NPC246638
0.8511	High Similarity	NPC26924
0.8511	High Similarity	NPC295339
0.8511	High Similarity	NPC103337
0.8511	High Similarity	NPC114620
0.8503	High Similarity	NPC280295
0.85	High Similarity	NPC53001
0.8496	Intermediate Similarity	NPC142956
0.8496	Intermediate Similarity	NPC74507
0.8496	Intermediate Similarity	NPC173978
0.8496	Intermediate Similarity	NPC310540
0.8496	Intermediate Similarity	NPC234890
0.8493	Intermediate Similarity	NPC94781
0.8493	Intermediate Similarity	NPC112816
0.8489	Intermediate Similarity	NPC80035
0.8489	Intermediate Similarity	NPC249272
0.8485	Intermediate Similarity	NPC282577
0.8478	Intermediate Similarity	NPC115458
0.8478	Intermediate Similarity	NPC114183
0.8478	Intermediate Similarity	NPC225051
0.8478	Intermediate Similarity	NPC294226
0.8472	Intermediate Similarity	NPC48130
0.8472	Intermediate Similarity	NPC218866
0.8472	Intermediate Similarity	NPC84568
0.8472	Intermediate Similarity	NPC300684
0.8467	Intermediate Similarity	NPC41847
0.8462	Intermediate Similarity	NPC248068
0.8462	Intermediate Similarity	NPC193555
0.8451	Intermediate Similarity	NPC471853
0.8451	Intermediate Similarity	NPC315578
0.8451	Intermediate Similarity	NPC203063
0.8446	Intermediate Similarity	NPC470569
0.844	Intermediate Similarity	NPC87723
0.844	Intermediate Similarity	NPC4214
0.8435	Intermediate Similarity	NPC44378
0.8435	Intermediate Similarity	NPC280753
0.8429	Intermediate Similarity	NPC191976
0.8421	Intermediate Similarity	NPC375356
0.8417	Intermediate Similarity	NPC282780
0.8417	Intermediate Similarity	NPC288089
0.8417	Intermediate Similarity	NPC474394
0.8417	Intermediate Similarity	NPC202225
0.8417	Intermediate Similarity	NPC166480
0.8417	Intermediate Similarity	NPC270899
0.8406	Intermediate Similarity	NPC478190
0.8406	Intermediate Similarity	NPC88864
0.8403	Intermediate Similarity	NPC21873
0.8392	Intermediate Similarity	NPC110810
0.8392	Intermediate Similarity	NPC290550
0.8389	Intermediate Similarity	NPC470340
0.8382	Intermediate Similarity	NPC165257
0.8382	Intermediate Similarity	NPC179898
0.8382	Intermediate Similarity	NPC237225
0.8382	Intermediate Similarity	NPC48248
0.838	Intermediate Similarity	NPC162939
0.8378	Intermediate Similarity	NPC255641
0.8378	Intermediate Similarity	NPC290954
0.8378	Intermediate Similarity	NPC147735
0.8378	Intermediate Similarity	NPC470568
0.837	Intermediate Similarity	NPC160499
0.837	Intermediate Similarity	NPC1991
0.837	Intermediate Similarity	NPC254492
0.837	Intermediate Similarity	NPC472047
0.837	Intermediate Similarity	NPC306765
0.8369	Intermediate Similarity	NPC147418
0.8369	Intermediate Similarity	NPC475957
0.8358	Intermediate Similarity	NPC199273
0.8357	Intermediate Similarity	NPC290803
0.8357	Intermediate Similarity	NPC161632
0.8357	Intermediate Similarity	NPC278375
0.8356	Intermediate Similarity	NPC314437
0.8356	Intermediate Similarity	NPC300540
0.8346	Intermediate Similarity	NPC300274
0.8345	Intermediate Similarity	NPC78307
0.8345	Intermediate Similarity	NPC59459
0.8345	Intermediate Similarity	NPC48036
0.8345	Intermediate Similarity	NPC475201
0.8345	Intermediate Similarity	NPC171968
0.8344	Intermediate Similarity	NPC472050
0.8333	Intermediate Similarity	NPC471851
0.8333	Intermediate Similarity	NPC182921
0.8333	Intermediate Similarity	NPC85310
0.8333	Intermediate Similarity	NPC239136
0.8333	Intermediate Similarity	NPC474824
0.8333	Intermediate Similarity	NPC218870
0.8333	Intermediate Similarity	NPC291078
0.8333	Intermediate Similarity	NPC470408
0.8333	Intermediate Similarity	NPC19631
0.8322	Intermediate Similarity	NPC183345
0.8321	Intermediate Similarity	NPC474546
0.8311	Intermediate Similarity	NPC134293
0.8311	Intermediate Similarity	NPC120171
0.8311	Intermediate Similarity	NPC478219
0.831	Intermediate Similarity	NPC141368
0.831	Intermediate Similarity	NPC230811
0.8309	Intermediate Similarity	NPC72667
0.8309	Intermediate Similarity	NPC324209
0.8299	Intermediate Similarity	NPC126767
0.8299	Intermediate Similarity	NPC245584
0.8299	Intermediate Similarity	NPC190648
0.8299	Intermediate Similarity	NPC53362
0.8299	Intermediate Similarity	NPC166583
0.8299	Intermediate Similarity	NPC289042
0.8299	Intermediate Similarity	NPC312929
0.8299	Intermediate Similarity	NPC56433
0.8299	Intermediate Similarity	NPC476821
0.8299	Intermediate Similarity	NPC118027
0.8298	Intermediate Similarity	NPC474311
0.8298	Intermediate Similarity	NPC155211
0.8298	Intermediate Similarity	NPC474813
0.8298	Intermediate Similarity	NPC272268

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 NPC315275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	882
0.2-0.3	1601
0.3-0.4	2731
0.4-0.5	2129
0.5-0.6	1064
0.6-0.7	366
0.7-0.8	87
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8832	High Similarity	NPD1509	Clinical (unspecified phase)
0.8571	High Similarity	NPD1470	Approved
0.8271	Intermediate Similarity	NPD1201	Approved
0.8231	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD943	Approved
0.7973	Intermediate Similarity	NPD7390	Discontinued
0.7919	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5404	Approved
0.7862	Intermediate Similarity	NPD5405	Approved
0.7862	Intermediate Similarity	NPD5406	Approved
0.7862	Intermediate Similarity	NPD5408	Approved
0.7667	Intermediate Similarity	NPD3300	Phase 2
0.7597	Intermediate Similarity	NPD3226	Approved
0.7566	Intermediate Similarity	NPD2532	Approved
0.7566	Intermediate Similarity	NPD2533	Approved
0.7566	Intermediate Similarity	NPD2534	Approved
0.756	Intermediate Similarity	NPD8150	Discontinued
0.7551	Intermediate Similarity	NPD1510	Phase 2
0.7548	Intermediate Similarity	NPD4380	Phase 2
0.7534	Intermediate Similarity	NPD1607	Approved
0.7517	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6232	Discontinued
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7453	Intermediate Similarity	NPD6959	Discontinued
0.745	Intermediate Similarity	NPD2346	Discontinued
0.7405	Intermediate Similarity	NPD7819	Suspended
0.74	Intermediate Similarity	NPD1549	Phase 2
0.7397	Intermediate Similarity	NPD1240	Approved
0.7394	Intermediate Similarity	NPD1164	Approved
0.7391	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1934	Approved
0.7333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7267	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7075	Discontinued
0.7239	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD230	Phase 1
0.7226	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4954	Approved
0.7219	Intermediate Similarity	NPD4955	Approved
0.7219	Intermediate Similarity	NPD36	Approved
0.7219	Intermediate Similarity	NPD5028	Approved
0.7219	Intermediate Similarity	NPD5034	Approved
0.7219	Intermediate Similarity	NPD5026	Approved
0.7214	Intermediate Similarity	NPD2932	Approved
0.72	Intermediate Similarity	NPD6534	Approved
0.72	Intermediate Similarity	NPD6535	Approved
0.719	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4628	Phase 3
0.7188	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD9269	Phase 2
0.7176	Intermediate Similarity	NPD8312	Approved
0.7176	Intermediate Similarity	NPD8313	Approved
0.7174	Intermediate Similarity	NPD9493	Approved
0.7161	Intermediate Similarity	NPD1511	Approved
0.716	Intermediate Similarity	NPD5030	Phase 2
0.7151	Intermediate Similarity	NPD5037	Approved
0.7151	Intermediate Similarity	NPD5038	Approved
0.7143	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6801	Discontinued
0.7124	Intermediate Similarity	NPD2800	Approved
0.7105	Intermediate Similarity	NPD2344	Approved
0.7099	Intermediate Similarity	NPD3882	Suspended
0.7095	Intermediate Similarity	NPD6782	Approved
0.7095	Intermediate Similarity	NPD6776	Approved
0.7095	Intermediate Similarity	NPD6777	Approved
0.7095	Intermediate Similarity	NPD6779	Approved
0.7095	Intermediate Similarity	NPD6781	Approved
0.7095	Intermediate Similarity	NPD6780	Approved
0.7095	Intermediate Similarity	NPD6778	Approved
0.7093	Intermediate Similarity	NPD5036	Approved
0.7092	Intermediate Similarity	NPD3019	Approved
0.709	Intermediate Similarity	NPD9266	Approved
0.709	Intermediate Similarity	NPD74	Approved
0.7086	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5844	Phase 1
0.7081	Intermediate Similarity	NPD2801	Approved
0.7079	Intermediate Similarity	NPD7699	Phase 2
0.7079	Intermediate Similarity	NPD7700	Phase 2
0.7071	Intermediate Similarity	NPD9545	Approved
0.707	Intermediate Similarity	NPD1512	Approved
0.7059	Intermediate Similarity	NPD6559	Discontinued
0.7055	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6213	Phase 3
0.7045	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6212	Phase 3
0.7044	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2796	Approved
0.7027	Intermediate Similarity	NPD3764	Approved
0.7024	Intermediate Similarity	NPD3818	Discontinued
0.7021	Intermediate Similarity	NPD9268	Approved
0.7015	Intermediate Similarity	NPD9267	Approved
0.7015	Intermediate Similarity	NPD9263	Approved
0.7015	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD9264	Approved
0.7013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6166	Phase 2
0.7006	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6599	Discontinued
0.6993	Remote Similarity	NPD1471	Phase 3
0.6988	Remote Similarity	NPD5711	Approved
0.6988	Remote Similarity	NPD5710	Approved
0.6978	Remote Similarity	NPD7435	Discontinued
0.6977	Remote Similarity	NPD5035	Approved
0.6974	Remote Similarity	NPD2799	Discontinued
0.697	Remote Similarity	NPD5494	Approved
0.6968	Remote Similarity	NPD3750	Approved
0.6968	Remote Similarity	NPD8166	Discontinued
0.6957	Remote Similarity	NPD7411	Suspended
0.6954	Remote Similarity	NPD6651	Approved
0.694	Remote Similarity	NPD8320	Phase 1
0.694	Remote Similarity	NPD8319	Approved
0.6939	Remote Similarity	NPD9494	Approved
0.6937	Remote Similarity	NPD7458	Discontinued
0.6928	Remote Similarity	NPD1551	Phase 2
0.6923	Remote Similarity	NPD3751	Discontinued
0.6923	Remote Similarity	NPD2309	Approved
0.6918	Remote Similarity	NPD3094	Phase 2
0.6913	Remote Similarity	NPD2313	Discontinued
0.6912	Remote Similarity	NPD4750	Phase 3
0.689	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7697	Approved
0.6885	Remote Similarity	NPD7696	Phase 3
0.6885	Remote Similarity	NPD7698	Approved
0.6882	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3092	Approved
0.6871	Remote Similarity	NPD2798	Approved
0.686	Remote Similarity	NPD5031	Approved
0.686	Remote Similarity	NPD5027	Approved
0.686	Remote Similarity	NPD5029	Approved
0.6859	Remote Similarity	NPD7003	Approved
0.6859	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8434	Phase 2
0.6849	Remote Similarity	NPD1283	Approved
0.6848	Remote Similarity	NPD3749	Approved
0.6848	Remote Similarity	NPD7870	Phase 2
0.6848	Remote Similarity	NPD7871	Phase 2
0.6842	Remote Similarity	NPD7074	Phase 3
0.6835	Remote Similarity	NPD6799	Approved
0.6829	Remote Similarity	NPD5402	Approved
0.6828	Remote Similarity	NPD7701	Phase 2
0.6818	Remote Similarity	NPD6099	Approved
0.6818	Remote Similarity	NPD6100	Approved
0.6815	Remote Similarity	NPD6190	Approved
0.6812	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.68	Remote Similarity	NPD411	Approved
0.6791	Remote Similarity	NPD1237	Approved
0.6791	Remote Similarity	NPD8151	Discontinued
0.6788	Remote Similarity	NPD7768	Phase 2
0.6786	Remote Similarity	NPD5951	Approved
0.6786	Remote Similarity	NPD9281	Approved
0.6784	Remote Similarity	NPD7054	Approved
0.6783	Remote Similarity	NPD1651	Approved
0.6776	Remote Similarity	NPD447	Suspended
0.6768	Remote Similarity	NPD1465	Phase 2
0.6765	Remote Similarity	NPD2342	Discontinued
0.6755	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6663	Approved
0.6755	Remote Similarity	NPD7874	Approved
0.6744	Remote Similarity	NPD7472	Approved
0.6739	Remote Similarity	NPD6823	Phase 2
0.6736	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4626	Approved
0.6727	Remote Similarity	NPD3817	Phase 2
0.672	Remote Similarity	NPD7801	Approved
0.6718	Remote Similarity	NPD288	Approved
0.6716	Remote Similarity	NPD9261	Approved
0.6713	Remote Similarity	NPD3091	Approved
0.6712	Remote Similarity	NPD3972	Approved
0.6712	Remote Similarity	NPD9717	Approved
0.6711	Remote Similarity	NPD5736	Approved
0.6708	Remote Similarity	NPD920	Approved
0.6708	Remote Similarity	NPD5403	Approved
0.6705	Remote Similarity	NPD6797	Phase 2
0.669	Remote Similarity	NPD3023	Approved
0.669	Remote Similarity	NPD3026	Approved
0.6689	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1203	Approved
0.6688	Remote Similarity	NPD1243	Approved
0.6687	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5401	Approved
0.6686	Remote Similarity	NPD6020	Phase 2
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD7251	Discontinued
0.6646	Remote Similarity	NPD3400	Discontinued
0.6646	Remote Similarity	NPD6273	Approved
0.6645	Remote Similarity	NPD3748	Approved
0.6645	Remote Similarity	NPD520	Approved
0.6644	Remote Similarity	NPD1281	Approved
0.6643	Remote Similarity	NPD7635	Approved
0.6641	Remote Similarity	NPD844	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