NPASS Compound

Structure

NPC29160 OpenBabel07101719242D 25 27 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 -0.8660 2.5000 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 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 -0.8660 1.5000 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 -1.7321 1.0000 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 1.7321 -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 -1.7321 -0.0000 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 7 1 0 0 0 0 2 8 1 0 0 0 0 3 24 1 0 0 0 0 4 7 2 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 5 11 2 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 8 19 2 0 0 0 0 8 25 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.07
Volume:	332.018
LogP:	3.287
LogD:	2.302
LogS:	-5.968
# Rotatable Bonds:	3
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	2.578
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.05
MDCK Permeability:	2.0232624592608772e-05
Pgp-inhibitor:	0.135
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.115
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.306

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	96.84696197509766%
Volume Distribution (VD):	0.64
Pgp-substrate:	3.522787570953369%

ADMET: Metabolism

CYP1A2-inhibitor:	0.816
CYP1A2-substrate:	0.58
CYP2C19-inhibitor:	0.119
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.34
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.505
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	5.441
Half-life (T1/2):	0.432

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.771
Rat Oral Acute Toxicity:	0.534
Maximum Recommended Daily Dose:	0.878
Skin Sensitization:	0.12
Carcinogencity:	0.27
Eye Corrosion:	0.004
Eye Irritation:	0.918
Respiratory Toxicity:	0.121

Download Data

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

Natural Product: NPC29160

Natural Product ID:	NPC29160
*Common Name:**	8-Acetoxy-3,5-Dihydroxy-7-Methoxy-2-Methylanthracene-9,10-Dione
IUPAC Name:	(4,6-dihydroxy-2-methoxy-7-methyl-9,10-dioxoanthracen-1-yl) acetate
Synonyms:
Standard InCHIKey:	SLRWHAFJOXBJHC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O7/c1-7-4-9-10(5-11(7)20)16(22)14-12(21)6-13(24-3)18(25-8(2)19)15(14)17(9)23/h4-6,20-21H,1-3H3
SMILES:	Cc1cc2c(cc1O)C(=O)c1c(cc(c(c1C2=O)OC(=O)C)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047320
PubChem CID:	59052029
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
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	>	200000.0	nM	PMID[534508]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	200000.0	nM	PMID[534508]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	200000.0	nM	PMID[534508]
NPT5776	Organism	Streptomyces albus	Streptomyces albus	MIC	=	100000.0	nM	PMID[534508]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100000.0	nM	PMID[534508]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	>	200000.0	nM	PMID[534508]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	200000.0	nM	PMID[534508]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	>	200000.0	nM	PMID[534508]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	>	200000.0	nM	PMID[534508]

☑ 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 NPC29160 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	405
0.1-0.2	1940
0.2-0.3	4468
0.3-0.4	9798
0.4-0.5	7986
0.5-0.6	3509
0.6-0.7	5069
0.7-0.8	5597
0.8-0.85	2721
0.85-0.9	1109
0.9-0.95	86
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC234331
0.9873	High Similarity	NPC99613
0.9873	High Similarity	NPC49487
0.9873	High Similarity	NPC163130
0.9873	High Similarity	NPC165979
0.975	High Similarity	NPC158226
0.9557	High Similarity	NPC108767
0.9497	High Similarity	NPC474350
0.9444	High Similarity	NPC124470
0.9444	High Similarity	NPC109827
0.943	High Similarity	NPC84571
0.9375	High Similarity	NPC156082
0.9375	High Similarity	NPC300984
0.9371	High Similarity	NPC311740
0.9371	High Similarity	NPC303565
0.9371	High Similarity	NPC66288
0.9325	High Similarity	NPC20543
0.9325	High Similarity	NPC1827
0.9325	High Similarity	NPC10576
0.9325	High Similarity	NPC239440
0.9317	High Similarity	NPC112981
0.9313	High Similarity	NPC294965
0.9304	High Similarity	NPC165977
0.9304	High Similarity	NPC217677
0.9273	High Similarity	NPC289147
0.9264	High Similarity	NPC26568
0.9259	High Similarity	NPC20216
0.9255	High Similarity	NPC270837
0.9255	High Similarity	NPC236132
0.9255	High Similarity	NPC197168
0.9241	High Similarity	NPC14561
0.9241	High Similarity	NPC77807
0.9241	High Similarity	NPC5379
0.9212	High Similarity	NPC181523
0.9207	High Similarity	NPC246716
0.9207	High Similarity	NPC17219
0.9202	High Similarity	NPC272485
0.9202	High Similarity	NPC292788
0.9198	High Similarity	NPC25361
0.9187	High Similarity	NPC228785
0.9187	High Similarity	NPC475886
0.9187	High Similarity	NPC56085
0.9187	High Similarity	NPC14353
0.9187	High Similarity	NPC474287
0.9182	High Similarity	NPC178976
0.9182	High Similarity	NPC199463
0.9182	High Similarity	NPC37543
0.9167	High Similarity	NPC294646
0.9157	High Similarity	NPC139350
0.913	High Similarity	NPC40491
0.913	High Similarity	NPC61010
0.913	High Similarity	NPC278052
0.913	High Similarity	NPC474187
0.913	High Similarity	NPC474186
0.913	High Similarity	NPC474351
0.913	High Similarity	NPC475883
0.9125	High Similarity	NPC100123
0.9125	High Similarity	NPC45846
0.9119	High Similarity	NPC146211
0.9114	High Similarity	NPC107109
0.9107	High Similarity	NPC113446
0.9085	High Similarity	NPC76647
0.908	High Similarity	NPC267153
0.9074	High Similarity	NPC470694
0.9074	High Similarity	NPC229632
0.9074	High Similarity	NPC93739
0.9068	High Similarity	NPC320359
0.9068	High Similarity	NPC47623
0.9068	High Similarity	NPC119224
0.9062	High Similarity	NPC300727
0.9062	High Similarity	NPC241904
0.9062	High Similarity	NPC262286
0.9062	High Similarity	NPC476981
0.9062	High Similarity	NPC36852
0.9057	High Similarity	NPC471800
0.9051	High Similarity	NPC154683
0.9051	High Similarity	NPC40356
0.9051	High Similarity	NPC175978
0.9048	High Similarity	NPC207467
0.9045	High Similarity	NPC474660
0.9045	High Similarity	NPC179183
0.9042	High Similarity	NPC245975
0.9024	High Similarity	NPC37870
0.9024	High Similarity	NPC30027
0.9018	High Similarity	NPC477689
0.9018	High Similarity	NPC7483
0.9018	High Similarity	NPC152659
0.9018	High Similarity	NPC236521
0.9018	High Similarity	NPC248638
0.9018	High Similarity	NPC284007
0.9018	High Similarity	NPC220313
0.9006	High Similarity	NPC238381
0.9006	High Similarity	NPC168616
0.9006	High Similarity	NPC476242
0.9006	High Similarity	NPC83763
0.9	High Similarity	NPC142339
0.9	High Similarity	NPC54928
0.9	High Similarity	NPC138243
0.9	High Similarity	NPC274730
0.8994	High Similarity	NPC475895
0.8994	High Similarity	NPC280937
0.8994	High Similarity	NPC473785
0.8987	High Similarity	NPC149614
0.8987	High Similarity	NPC117579
0.8981	High Similarity	NPC291049
0.8981	High Similarity	NPC233267
0.8974	High Similarity	NPC312929
0.8974	High Similarity	NPC190648
0.8974	High Similarity	NPC118027
0.8974	High Similarity	NPC126767
0.8974	High Similarity	NPC289042
0.8974	High Similarity	NPC245584
0.8974	High Similarity	NPC56433
0.8963	High Similarity	NPC326520
0.8963	High Similarity	NPC26386
0.8963	High Similarity	NPC472450
0.8963	High Similarity	NPC8070
0.8963	High Similarity	NPC239752
0.8963	High Similarity	NPC275780
0.896	High Similarity	NPC295436
0.8957	High Similarity	NPC52204
0.8957	High Similarity	NPC144843
0.8957	High Similarity	NPC25152
0.8951	High Similarity	NPC476980
0.8951	High Similarity	NPC143050
0.8944	High Similarity	NPC236796
0.8944	High Similarity	NPC78225
0.8944	High Similarity	NPC263483
0.8944	High Similarity	NPC181960
0.8941	High Similarity	NPC265795
0.8938	High Similarity	NPC113906
0.8938	High Similarity	NPC20541
0.8931	High Similarity	NPC101996
0.8931	High Similarity	NPC149889
0.8931	High Similarity	NPC273483
0.8931	High Similarity	NPC312338
0.8924	High Similarity	NPC306821
0.8924	High Similarity	NPC147735
0.8924	High Similarity	NPC470107
0.8924	High Similarity	NPC295036
0.8924	High Similarity	NPC473466
0.8922	High Similarity	NPC260263
0.8917	High Similarity	NPC2569
0.8917	High Similarity	NPC172329
0.8917	High Similarity	NPC105415
0.8909	High Similarity	NPC472452
0.8909	High Similarity	NPC39091
0.8909	High Similarity	NPC170245
0.8902	High Similarity	NPC234004
0.8902	High Similarity	NPC23298
0.8902	High Similarity	NPC101769
0.8902	High Similarity	NPC207690
0.8902	High Similarity	NPC189473
0.8896	High Similarity	NPC32694
0.8896	High Similarity	NPC258331
0.8889	High Similarity	NPC85121
0.8882	High Similarity	NPC191146
0.8882	High Similarity	NPC240887
0.8882	High Similarity	NPC470091
0.8882	High Similarity	NPC212290
0.8882	High Similarity	NPC68093
0.8882	High Similarity	NPC329161
0.8875	High Similarity	NPC89474
0.8875	High Similarity	NPC167091
0.8875	High Similarity	NPC186507
0.8875	High Similarity	NPC292214
0.8875	High Similarity	NPC472915
0.8875	High Similarity	NPC214632
0.8875	High Similarity	NPC206238
0.8875	High Similarity	NPC88645
0.8875	High Similarity	NPC271779
0.8869	High Similarity	NPC261471
0.8869	High Similarity	NPC65885
0.8868	High Similarity	NPC202157
0.8868	High Similarity	NPC208043
0.8868	High Similarity	NPC171010
0.8868	High Similarity	NPC473201
0.8868	High Similarity	NPC308451
0.8868	High Similarity	NPC226973
0.8868	High Similarity	NPC302783
0.8868	High Similarity	NPC474663
0.8868	High Similarity	NPC133856
0.8862	High Similarity	NPC78830
0.8862	High Similarity	NPC218533
0.8861	High Similarity	NPC106334
0.8861	High Similarity	NPC328119
0.8861	High Similarity	NPC70764
0.8861	High Similarity	NPC285527
0.8855	High Similarity	NPC6588
0.8855	High Similarity	NPC477154
0.8855	High Similarity	NPC117854
0.8855	High Similarity	NPC86477
0.8848	High Similarity	NPC303174
0.8844	High Similarity	NPC174486
0.8841	High Similarity	NPC8300
0.8841	High Similarity	NPC329760
0.8841	High Similarity	NPC472448
0.8841	High Similarity	NPC83922
0.8841	High Similarity	NPC81679
0.8834	High Similarity	NPC235018

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 NPC29160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	389
0.1-0.2	1032
0.2-0.3	1904
0.3-0.4	2589
0.4-0.5	1732
0.5-0.6	919
0.6-0.7	384
0.7-0.8	158
0.8-0.85	33
0.85-0.9	7
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9193	High Similarity	NPD6232	Discontinued
0.9141	High Similarity	NPD7473	Discontinued
0.903	High Similarity	NPD5844	Phase 1
0.8758	High Similarity	NPD2801	Approved
0.8625	High Similarity	NPD3226	Approved
0.858	High Similarity	NPD1934	Approved
0.8528	High Similarity	NPD1465	Phase 2
0.8528	High Similarity	NPD2393	Clinical (unspecified phase)
0.8528	High Similarity	NPD7819	Suspended
0.8494	Intermediate Similarity	NPD5494	Approved
0.8424	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD2532	Approved
0.8375	Intermediate Similarity	NPD2533	Approved
0.8375	Intermediate Similarity	NPD2534	Approved
0.8364	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8313	Intermediate Similarity	NPD1511	Approved
0.8313	Intermediate Similarity	NPD3882	Suspended
0.8305	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7075	Discontinued
0.8263	Intermediate Similarity	NPD3749	Approved
0.8261	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD1512	Approved
0.8198	Intermediate Similarity	NPD3818	Discontinued
0.8193	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD7411	Suspended
0.8171	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD2346	Discontinued
0.8125	Intermediate Similarity	NPD3750	Approved
0.8121	Intermediate Similarity	NPD6599	Discontinued
0.8111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD919	Approved
0.8101	Intermediate Similarity	NPD2935	Discontinued
0.8037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1607	Approved
0.8024	Intermediate Similarity	NPD6801	Discontinued
0.8012	Intermediate Similarity	NPD4380	Phase 2
0.8012	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD1549	Phase 2
0.8	Intermediate Similarity	NPD7074	Phase 3
0.7988	Intermediate Similarity	NPD7768	Phase 2
0.7977	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6799	Approved
0.7962	Intermediate Similarity	NPD447	Suspended
0.7955	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7054	Approved
0.7937	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD5402	Approved
0.7925	Intermediate Similarity	NPD1510	Phase 2
0.7917	Intermediate Similarity	NPD37	Approved
0.791	Intermediate Similarity	NPD6559	Discontinued
0.7898	Intermediate Similarity	NPD1240	Approved
0.7898	Intermediate Similarity	NPD7472	Approved
0.7895	Intermediate Similarity	NPD6234	Discontinued
0.7882	Intermediate Similarity	NPD4967	Phase 2
0.7882	Intermediate Similarity	NPD4966	Approved
0.7882	Intermediate Similarity	NPD4965	Approved
0.7875	Intermediate Similarity	NPD1551	Phase 2
0.784	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1243	Approved
0.784	Intermediate Similarity	NPD2800	Approved
0.7836	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD920	Approved
0.7816	Intermediate Similarity	NPD3926	Phase 2
0.7812	Intermediate Similarity	NPD3748	Approved
0.7765	Intermediate Similarity	NPD7808	Phase 3
0.7764	Intermediate Similarity	NPD2796	Approved
0.7759	Intermediate Similarity	NPD5710	Approved
0.7759	Intermediate Similarity	NPD5711	Approved
0.7758	Intermediate Similarity	NPD7390	Discontinued
0.7753	Intermediate Similarity	NPD6797	Phase 2
0.7736	Intermediate Similarity	NPD230	Phase 1
0.7722	Intermediate Similarity	NPD8313	Approved
0.7722	Intermediate Similarity	NPD8312	Approved
0.7711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7251	Discontinued
0.7702	Intermediate Similarity	NPD2799	Discontinued
0.7701	Intermediate Similarity	NPD7199	Phase 2
0.7684	Intermediate Similarity	NPD7435	Discontinued
0.7684	Intermediate Similarity	NPD3751	Discontinued
0.7683	Intermediate Similarity	NPD4628	Phase 3
0.7683	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD943	Approved
0.7668	Intermediate Similarity	NPD8151	Discontinued
0.7658	Intermediate Similarity	NPD2313	Discontinued
0.7654	Intermediate Similarity	NPD5953	Discontinued
0.764	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6776	Approved
0.7619	Intermediate Similarity	NPD6781	Approved
0.7619	Intermediate Similarity	NPD6779	Approved
0.7619	Intermediate Similarity	NPD6777	Approved
0.7619	Intermediate Similarity	NPD6780	Approved
0.7619	Intermediate Similarity	NPD6782	Approved
0.7619	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6778	Approved
0.7614	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8150	Discontinued
0.759	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7228	Approved
0.7576	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5405	Approved
0.7546	Intermediate Similarity	NPD6099	Approved
0.7546	Intermediate Similarity	NPD6100	Approved
0.7546	Intermediate Similarity	NPD5404	Approved
0.7546	Intermediate Similarity	NPD5408	Approved
0.7546	Intermediate Similarity	NPD5406	Approved
0.7545	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7286	Phase 2
0.7529	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1933	Approved
0.7515	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD7698	Approved
0.75	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7783	Phase 2
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD7696	Phase 3
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD7697	Approved
0.7485	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7870	Phase 2
0.7461	Intermediate Similarity	NPD7871	Phase 2
0.7458	Intermediate Similarity	NPD7229	Phase 3
0.7452	Intermediate Similarity	NPD1470	Approved
0.7452	Intermediate Similarity	NPD1203	Approved
0.7449	Intermediate Similarity	NPD7874	Approved
0.7449	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7458	Discontinued
0.7396	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4308	Phase 3
0.7368	Intermediate Similarity	NPD1653	Approved
0.7365	Intermediate Similarity	NPD7003	Approved
0.736	Intermediate Similarity	NPD3787	Discontinued
0.7358	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6535	Approved
0.7354	Intermediate Similarity	NPD6534	Approved
0.7347	Intermediate Similarity	NPD7701	Phase 2
0.7329	Intermediate Similarity	NPD411	Approved
0.7329	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3764	Approved
0.7326	Intermediate Similarity	NPD4287	Approved
0.7321	Intermediate Similarity	NPD2309	Approved
0.7321	Intermediate Similarity	NPD6190	Approved
0.7318	Intermediate Similarity	NPD5242	Approved
0.7312	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8127	Discontinued
0.7301	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7177	Discontinued
0.7268	Intermediate Similarity	NPD6823	Phase 2
0.7267	Intermediate Similarity	NPD4625	Phase 3
0.7261	Intermediate Similarity	NPD9717	Approved
0.7256	Intermediate Similarity	NPD6651	Approved
0.7251	Intermediate Similarity	NPD6273	Approved
0.7251	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7700	Phase 2
0.724	Intermediate Similarity	NPD7699	Phase 2
0.7239	Intermediate Similarity	NPD1613	Approved
0.7239	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7801	Approved
0.7228	Intermediate Similarity	NPD7240	Approved
0.7222	Intermediate Similarity	NPD3268	Approved
0.7216	Intermediate Similarity	NPD4288	Approved
0.7205	Intermediate Similarity	NPD6832	Phase 2
0.7202	Intermediate Similarity	NPD8285	Discontinued
0.7197	Intermediate Similarity	NPD1201	Approved
0.7189	Intermediate Similarity	NPD7549	Discontinued
0.7189	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1471	Phase 3
0.7186	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1283	Approved
0.7152	Intermediate Similarity	NPD9269	Phase 2
0.7152	Intermediate Similarity	NPD1608	Approved
0.7135	Intermediate Similarity	NPD7038	Approved
0.7135	Intermediate Similarity	NPD7039	Approved
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7134	Intermediate Similarity	NPD4307	Phase 2
0.7125	Intermediate Similarity	NPD2797	Approved
0.712	Intermediate Similarity	NPD6213	Phase 3
0.712	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6212	Phase 3
0.7119	Intermediate Similarity	NPD5353	Approved
0.7117	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD9268	Approved
0.7112	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8320	Phase 1
0.7107	Intermediate Similarity	NPD8319	Approved
0.7104	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1611	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