NPASS Compound

Structure

NPC99613 OpenBabel07101719512D 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 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 -5.1962 3.0000 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 -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 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 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 1.7321 -1.0000 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 -5.1962 2.0000 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 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 14 2 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 14 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 16 1 0 0 0 0 13 23 1 0 0 0 0 14 27 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 24 2 0 0 0 0 19 25 2 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.08
Volume:	372.764
LogP:	3.418
LogD:	2.239
LogS:	-6.526
# 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:	2.613
Fsp3:	0.2
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:	-5.063
MDCK Permeability:	3.492961695883423e-05
Pgp-inhibitor:	0.675
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.201
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	90.17071533203125%
Volume Distribution (VD):	0.861
Pgp-substrate:	13.646829605102539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.613
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.172
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.722
CYP2C9-substrate:	0.409
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.188
CYP3A4-inhibitor:	0.487
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	1.794
Half-life (T1/2):	0.341

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.015
Drug-inuced Liver Injury (DILI):	0.841
AMES Toxicity:	0.705
Rat Oral Acute Toxicity:	0.8
Maximum Recommended Daily Dose:	0.769
Skin Sensitization:	0.278
Carcinogencity:	0.241
Eye Corrosion:	0.004
Eye Irritation:	0.761
Respiratory Toxicity:	0.219

Download Data

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

Natural Product: NPC99613

Natural Product ID:	NPC99613
*Common Name:**	3,8-Diacetoxy-5-Hydroxy-7-Methoxy-2-Methylanthracene-9,10-Dione
IUPAC Name:	(5-acetyloxy-8-hydroxy-6-methoxy-3-methyl-9,10-dioxoanthracen-2-yl) acetate
Synonyms:
Standard InCHIKey:	HVCPDVLSJSEEQU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O8/c1-8-5-11-12(6-14(8)27-9(2)21)18(24)16-13(23)7-15(26-4)20(28-10(3)22)17(16)19(11)25/h5-7,23H,1-4H3
SMILES:	Cc1cc2c(cc1OC(=O)C)C(=O)c1c(cc(c(c1C2=O)OC(=O)C)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047324
PubChem CID:	59052033
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	>	200000.0	nM	PMID[516076]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	200000.0	nM	PMID[516076]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	200000.0	nM	PMID[516076]
NPT5776	Organism	Streptomyces albus	Streptomyces albus	MIC	>	200000.0	nM	PMID[516076]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	200000.0	nM	PMID[516076]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	=	200000.0	nM	PMID[516076]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	200000.0	nM	PMID[516076]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	>	200000.0	nM	PMID[516076]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	>	200000.0	nM	PMID[516076]

☑ 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 NPC99613 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	407
0.1-0.2	1818
0.2-0.3	4287
0.3-0.4	9471
0.4-0.5	8511
0.5-0.6	3508
0.6-0.7	5092
0.7-0.8	5572
0.8-0.85	2969
0.85-0.9	971
0.9-0.95	82
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC49487
0.9875	High Similarity	NPC158226
0.9873	High Similarity	NPC29160
0.9811	High Similarity	NPC234331
0.975	High Similarity	NPC163130
0.975	High Similarity	NPC165979
0.9684	High Similarity	NPC108767
0.9623	High Similarity	NPC474350
0.9568	High Similarity	NPC124470
0.9568	High Similarity	NPC109827
0.95	High Similarity	NPC300984
0.9383	High Similarity	NPC20216
0.9379	High Similarity	NPC156082
0.9375	High Similarity	NPC303565
0.9375	High Similarity	NPC66288
0.9333	High Similarity	NPC181523
0.9329	High Similarity	NPC20543
0.9329	High Similarity	NPC10576
0.9329	High Similarity	NPC1827
0.9329	High Similarity	NPC17219
0.9329	High Similarity	NPC246716
0.9329	High Similarity	NPC239440
0.9321	High Similarity	NPC112981
0.9313	High Similarity	NPC84571
0.9308	High Similarity	NPC165977
0.9308	High Similarity	NPC217677
0.9277	High Similarity	NPC139350
0.9277	High Similarity	NPC289147
0.9268	High Similarity	NPC26568
0.9259	High Similarity	NPC270837
0.9259	High Similarity	NPC236132
0.9259	High Similarity	NPC197168
0.9255	High Similarity	NPC311740
0.9245	High Similarity	NPC146211
0.9226	High Similarity	NPC113446
0.9207	High Similarity	NPC272485
0.9207	High Similarity	NPC292788
0.9207	High Similarity	NPC76647
0.9202	High Similarity	NPC267153
0.9202	High Similarity	NPC25361
0.9198	High Similarity	NPC294965
0.9198	High Similarity	NPC93739
0.9193	High Similarity	NPC56085
0.9193	High Similarity	NPC14353
0.9193	High Similarity	NPC474287
0.9193	High Similarity	NPC475886
0.9193	High Similarity	NPC228785
0.9187	High Similarity	NPC199463
0.9187	High Similarity	NPC37543
0.9167	High Similarity	NPC207467
0.9146	High Similarity	NPC30027
0.9141	High Similarity	NPC284007
0.9136	High Similarity	NPC474351
0.9136	High Similarity	NPC474186
0.9136	High Similarity	NPC278052
0.9136	High Similarity	NPC40491
0.9136	High Similarity	NPC475883
0.9136	High Similarity	NPC474187
0.9136	High Similarity	NPC61010
0.913	High Similarity	NPC45846
0.913	High Similarity	NPC100123
0.9125	High Similarity	NPC14561
0.9125	High Similarity	NPC5379
0.9125	High Similarity	NPC54928
0.9125	High Similarity	NPC77807
0.9119	High Similarity	NPC475895
0.9112	High Similarity	NPC473785
0.9085	High Similarity	NPC8070
0.908	High Similarity	NPC470694
0.908	High Similarity	NPC229632
0.9075	High Similarity	NPC295436
0.9074	High Similarity	NPC47623
0.9074	High Similarity	NPC119224
0.9074	High Similarity	NPC320359
0.9074	High Similarity	NPC143050
0.9068	High Similarity	NPC300727
0.9068	High Similarity	NPC241904
0.9068	High Similarity	NPC263483
0.9068	High Similarity	NPC262286
0.9068	High Similarity	NPC476981
0.9068	High Similarity	NPC178976
0.9068	High Similarity	NPC36852
0.9062	High Similarity	NPC471800
0.9059	High Similarity	NPC265795
0.9057	High Similarity	NPC154683
0.9057	High Similarity	NPC40356
0.9051	High Similarity	NPC473466
0.9051	High Similarity	NPC294646
0.9051	High Similarity	NPC474660
0.9048	High Similarity	NPC245975
0.903	High Similarity	NPC37870
0.9024	High Similarity	NPC220313
0.9024	High Similarity	NPC477689
0.9024	High Similarity	NPC7483
0.9024	High Similarity	NPC152659
0.9024	High Similarity	NPC236521
0.9024	High Similarity	NPC248638
0.9012	High Similarity	NPC476242
0.9012	High Similarity	NPC83763
0.9012	High Similarity	NPC238381
0.9012	High Similarity	NPC168616
0.9006	High Similarity	NPC142339
0.9006	High Similarity	NPC274730
0.9006	High Similarity	NPC138243
0.9	High Similarity	NPC212290
0.9	High Similarity	NPC107109
0.9	High Similarity	NPC280937
0.8994	High Similarity	NPC474663
0.8994	High Similarity	NPC133856
0.8987	High Similarity	NPC233267
0.8987	High Similarity	NPC291049
0.8987	High Similarity	NPC106334
0.8987	High Similarity	NPC285527
0.897	High Similarity	NPC472450
0.897	High Similarity	NPC275780
0.897	High Similarity	NPC26386
0.897	High Similarity	NPC326520
0.897	High Similarity	NPC239752
0.8963	High Similarity	NPC52204
0.8963	High Similarity	NPC144843
0.8963	High Similarity	NPC25152
0.896	High Similarity	NPC174486
0.8957	High Similarity	NPC476980
0.8951	High Similarity	NPC78225
0.8951	High Similarity	NPC181960
0.8951	High Similarity	NPC236796
0.8947	High Similarity	NPC208069
0.8944	High Similarity	NPC208197
0.8944	High Similarity	NPC113906
0.8941	High Similarity	NPC297807
0.8938	High Similarity	NPC273483
0.8938	High Similarity	NPC175978
0.8938	High Similarity	NPC289968
0.8935	High Similarity	NPC68381
0.8935	High Similarity	NPC146803
0.8931	High Similarity	NPC179183
0.8931	High Similarity	NPC29056
0.8931	High Similarity	NPC164527
0.8931	High Similarity	NPC213382
0.8924	High Similarity	NPC172329
0.8924	High Similarity	NPC105415
0.8924	High Similarity	NPC2569
0.8922	High Similarity	NPC280493
0.8916	High Similarity	NPC39091
0.8916	High Similarity	NPC472452
0.8916	High Similarity	NPC170245
0.8909	High Similarity	NPC41301
0.8909	High Similarity	NPC23298
0.8909	High Similarity	NPC234004
0.8909	High Similarity	NPC207690
0.8909	High Similarity	NPC189473
0.8902	High Similarity	NPC258331
0.8902	High Similarity	NPC266314
0.8902	High Similarity	NPC32694
0.8896	High Similarity	NPC287458
0.8896	High Similarity	NPC154304
0.8896	High Similarity	NPC190487
0.8896	High Similarity	NPC85121
0.8889	High Similarity	NPC240887
0.8889	High Similarity	NPC191146
0.8889	High Similarity	NPC329161
0.8889	High Similarity	NPC470091
0.8889	High Similarity	NPC68093
0.8882	High Similarity	NPC216307
0.8882	High Similarity	NPC186507
0.8882	High Similarity	NPC276409
0.8882	High Similarity	NPC472915
0.8882	High Similarity	NPC89474
0.8882	High Similarity	NPC250822
0.8882	High Similarity	NPC75279
0.8876	High Similarity	NPC65885
0.8876	High Similarity	NPC37606
0.8876	High Similarity	NPC261471
0.8875	High Similarity	NPC226973
0.8875	High Similarity	NPC117579
0.8875	High Similarity	NPC198615
0.8875	High Similarity	NPC149614
0.8875	High Similarity	NPC208043
0.8875	High Similarity	NPC308451
0.8869	High Similarity	NPC78830
0.8869	High Similarity	NPC72696
0.8869	High Similarity	NPC218533
0.8868	High Similarity	NPC328119
0.8862	High Similarity	NPC117854
0.8862	High Similarity	NPC6588
0.8862	High Similarity	NPC477154
0.8862	High Similarity	NPC107009
0.8862	High Similarity	NPC474024
0.8861	High Similarity	NPC245584
0.8861	High Similarity	NPC126767
0.8861	High Similarity	NPC118027
0.8861	High Similarity	NPC56433
0.8861	High Similarity	NPC312929
0.8861	High Similarity	NPC190648
0.8861	High Similarity	NPC289042
0.8855	High Similarity	NPC303174
0.8851	High Similarity	NPC105591
0.8848	High Similarity	NPC8300
0.8848	High Similarity	NPC329760
0.8848	High Similarity	NPC472448

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 NPC99613 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	1030
0.2-0.3	1880
0.3-0.4	2578
0.4-0.5	1797
0.5-0.6	892
0.6-0.7	402
0.7-0.8	158
0.8-0.85	33
0.85-0.9	8
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9317	High Similarity	NPD6232	Discontinued
0.9264	High Similarity	NPD7473	Discontinued
0.9036	High Similarity	NPD5844	Phase 1
0.8765	High Similarity	NPD2801	Approved
0.865	High Similarity	NPD7819	Suspended
0.8634	High Similarity	NPD3226	Approved
0.8545	High Similarity	NPD4868	Clinical (unspecified phase)
0.8537	High Similarity	NPD2393	Clinical (unspecified phase)
0.8537	High Similarity	NPD1465	Phase 2
0.8503	High Similarity	NPD5494	Approved
0.8485	Intermediate Similarity	NPD3817	Phase 2
0.8476	Intermediate Similarity	NPD1934	Approved
0.8452	Intermediate Similarity	NPD6959	Discontinued
0.8418	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD2532	Approved
0.8385	Intermediate Similarity	NPD2534	Approved
0.8385	Intermediate Similarity	NPD2533	Approved
0.8383	Intermediate Similarity	NPD7075	Discontinued
0.8323	Intermediate Similarity	NPD3882	Suspended
0.8314	Intermediate Similarity	NPD3818	Discontinued
0.8304	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD6166	Phase 2
0.8303	Intermediate Similarity	NPD7411	Suspended
0.8286	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD1511	Approved
0.8204	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD3749	Approved
0.8165	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6801	Discontinued
0.8133	Intermediate Similarity	NPD6599	Discontinued
0.8133	Intermediate Similarity	NPD4380	Phase 2
0.8125	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD7074	Phase 3
0.8113	Intermediate Similarity	NPD2935	Discontinued
0.811	Intermediate Similarity	NPD1512	Approved
0.8092	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD2346	Discontinued
0.8057	Intermediate Similarity	NPD7054	Approved
0.8047	Intermediate Similarity	NPD5402	Approved
0.8047	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD37	Approved
0.8025	Intermediate Similarity	NPD3750	Approved
0.8023	Intermediate Similarity	NPD6559	Discontinued
0.8012	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD6234	Discontinued
0.8011	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD4967	Phase 2
0.8	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD4966	Approved
0.8	Intermediate Similarity	NPD4965	Approved
0.7988	Intermediate Similarity	NPD6799	Approved
0.7953	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3926	Phase 2
0.7925	Intermediate Similarity	NPD1607	Approved
0.7919	Intermediate Similarity	NPD1247	Approved
0.7901	Intermediate Similarity	NPD1549	Phase 2
0.7879	Intermediate Similarity	NPD7390	Discontinued
0.7877	Intermediate Similarity	NPD7808	Phase 3
0.7865	Intermediate Similarity	NPD6797	Phase 2
0.7862	Intermediate Similarity	NPD447	Suspended
0.7853	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD8313	Approved
0.7833	Intermediate Similarity	NPD8312	Approved
0.7826	Intermediate Similarity	NPD1510	Phase 2
0.7821	Intermediate Similarity	NPD7251	Discontinued
0.7816	Intermediate Similarity	NPD7199	Phase 2
0.7799	Intermediate Similarity	NPD1240	Approved
0.7789	Intermediate Similarity	NPD7435	Discontinued
0.7778	Intermediate Similarity	NPD1551	Phase 2
0.7778	Intermediate Similarity	NPD2796	Approved
0.7772	Intermediate Similarity	NPD8151	Discontinued
0.7771	Intermediate Similarity	NPD5710	Approved
0.7771	Intermediate Similarity	NPD5711	Approved
0.7765	Intermediate Similarity	NPD5953	Discontinued
0.7753	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2800	Approved
0.7744	Intermediate Similarity	NPD1243	Approved
0.7738	Intermediate Similarity	NPD920	Approved
0.7727	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6781	Approved
0.7725	Intermediate Similarity	NPD6777	Approved
0.7725	Intermediate Similarity	NPD6779	Approved
0.7725	Intermediate Similarity	NPD6780	Approved
0.7725	Intermediate Similarity	NPD6782	Approved
0.7725	Intermediate Similarity	NPD6778	Approved
0.7725	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6776	Approved
0.7716	Intermediate Similarity	NPD2799	Discontinued
0.7716	Intermediate Similarity	NPD3748	Approved
0.7705	Intermediate Similarity	NPD8150	Discontinued
0.7697	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7228	Approved
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD230	Phase 1
0.7633	Intermediate Similarity	NPD5403	Approved
0.7619	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD8434	Phase 2
0.7604	Intermediate Similarity	NPD7698	Approved
0.7604	Intermediate Similarity	NPD7696	Phase 3
0.7604	Intermediate Similarity	NPD7697	Approved
0.7602	Intermediate Similarity	NPD7783	Phase 2
0.7602	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD3751	Discontinued
0.7578	Intermediate Similarity	NPD943	Approved
0.7565	Intermediate Similarity	NPD7870	Phase 2
0.7565	Intermediate Similarity	NPD7871	Phase 2
0.7562	Intermediate Similarity	NPD2313	Discontinued
0.7561	Intermediate Similarity	NPD5404	Approved
0.7561	Intermediate Similarity	NPD5408	Approved
0.7561	Intermediate Similarity	NPD5406	Approved
0.7561	Intermediate Similarity	NPD5405	Approved
0.7561	Intermediate Similarity	NPD6099	Approved
0.7561	Intermediate Similarity	NPD6100	Approved
0.756	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7286	Phase 2
0.7551	Intermediate Similarity	NPD7874	Approved
0.7551	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1653	Approved
0.7472	Intermediate Similarity	NPD7229	Phase 3
0.746	Intermediate Similarity	NPD6534	Approved
0.746	Intermediate Similarity	NPD6535	Approved
0.7453	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7701	Phase 2
0.7442	Intermediate Similarity	NPD7458	Discontinued
0.744	Intermediate Similarity	NPD6190	Approved
0.7423	Intermediate Similarity	NPD1933	Approved
0.7416	Intermediate Similarity	NPD8127	Discontinued
0.741	Intermediate Similarity	NPD2344	Approved
0.7394	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7003	Approved
0.7378	Intermediate Similarity	NPD6651	Approved
0.7374	Intermediate Similarity	NPD3787	Discontinued
0.7371	Intermediate Similarity	NPD6823	Phase 2
0.7358	Intermediate Similarity	NPD1203	Approved
0.7358	Intermediate Similarity	NPD1470	Approved
0.7346	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7700	Phase 2
0.7344	Intermediate Similarity	NPD7699	Phase 2
0.7337	Intermediate Similarity	NPD7801	Approved
0.7337	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD5242	Approved
0.7329	Intermediate Similarity	NPD6832	Phase 2
0.731	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7177	Discontinued
0.7306	Intermediate Similarity	NPD8285	Discontinued
0.7292	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4308	Phase 3
0.7284	Intermediate Similarity	NPD4625	Phase 3
0.7267	Intermediate Similarity	NPD6273	Approved
0.7267	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD4287	Approved
0.7239	Intermediate Similarity	NPD3268	Approved
0.7239	Intermediate Similarity	NPD411	Approved
0.7239	Intermediate Similarity	NPD3764	Approved
0.7235	Intermediate Similarity	NPD2309	Approved
0.7225	Intermediate Similarity	NPD6213	Phase 3
0.7225	Intermediate Similarity	NPD6212	Phase 3
0.7225	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8320	Phase 1
0.7208	Intermediate Similarity	NPD8319	Approved
0.7204	Intermediate Similarity	NPD7549	Discontinued
0.7204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD9717	Approved
0.7168	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD1613	Approved
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7151	Intermediate Similarity	NPD7038	Approved
0.7151	Intermediate Similarity	NPD7039	Approved
0.7143	Intermediate Similarity	NPD2797	Approved
0.7135	Intermediate Similarity	NPD5353	Approved
0.7135	Intermediate Similarity	NPD4288	Approved
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1201	Approved
0.7101	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1471	Phase 3
0.7085	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1283	Approved
0.7073	Intermediate Similarity	NPD3027	Phase 3
0.7063	Intermediate Similarity	NPD1608	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