NPASS Compound

Structure

NPC471809 OpenBabel07101719242D 29 31 0 0 0 0 0 0 0 0999 V2000 -1.7568 -2.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3017 4.5048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5549 2.4040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -1.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8678 3.6039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 -1.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 3.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 -0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5633 2.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 2.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9944 1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3548 -0.0990 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.1238 3.3797 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 2.9010 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.8650 -0.0747 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.3548 1.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1974 -1.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9916 1.5777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 2.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 27 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 10 20 1 0 0 0 0 11 15 2 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 13 23 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 19 2 0 0 0 0 16 28 1 0 0 0 0 17 28 1 0 0 0 0 18 27 1 0 0 0 0 19 29 1 0 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	477.99
Volume:	415.147
LogP:	7.405
LogD:	4.459
LogS:	-7.177
# Rotatable Bonds:	5
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.361
Synthetic Accessibility Score:	3.368
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.01
MDCK Permeability:	1.6620733731542714e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	102.08687591552734%
Volume Distribution (VD):	3.222
Pgp-substrate:	1.3346295356750488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.295
CYP1A2-substrate:	0.638
CYP2C19-inhibitor:	0.437
CYP2C19-substrate:	0.311
CYP2C9-inhibitor:	0.868
CYP2C9-substrate:	0.977
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.35
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	6.278
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.028
Drug-inuced Liver Injury (DILI):	0.149
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.994
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.882
Carcinogencity:	0.225
Eye Corrosion:	0.003
Eye Irritation:	0.896
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC471809

Natural Product ID:	NPC471809
*Common Name:**	Spiromastixone J
IUPAC Name:	2,4,8,10-tetrachloro-9-hydroxy-3-methoxy-1,7-dipropylbenzo[b][1,4]benzodioxepin-6-one
Synonyms:
Standard InCHIKey:	LGBNCRLLRCTJOP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18Cl4O5/c1-4-6-8-10-17(13(23)15(25)11(8)21)28-16-9(7-5-2)12(22)18(27-3)14(24)19(16)29-20(10)26/h25H,4-7H2,1-3H3
SMILES:	CCCc1c2C(=O)Oc3c(Oc2c(c(c1Cl)O)Cl)c(CCC)c(c(c3Cl)OC)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234400
PubChem CID:	86302535
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO33095	spiromastix sp. mccc 3a00308	Species	n.a.	Eukaryota	n.a.	isolated from the deep-sea sediment that was collected from the South Atlantic Ocean (GPS 13.7501 W, 15.1668 S) at a depth of 2869 m	2011-JUN	PMID[24571273]

☑ 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	24
MIC	4
Others	1

Activity Type	# Activity
Organism	29

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.125	ug.mL-1	PMID[537320]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	=	0.25	ug.mL-1	PMID[537320]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.125	ug.mL-1	PMID[537320]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[537320]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	4000.0	nM	PMID[537320]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	2000.0	nM	PMID[537320]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IC50	=	4000.0	nM	PMID[537320]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IC50	=	2000.0	nM	PMID[537320]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IC50	=	1000.0	nM	PMID[537320]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IC50	=	4000.0	nM	PMID[537320]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IC50	=	4000.0	nM	PMID[537320]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>	256000.0	nM	PMID[537320]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IC50	>	256000.0	nM	PMID[537320]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Ratio IC50	=	2.0	n.a.	PMID[537320]

☑ 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 NPC471809 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	480
0.1-0.2	2757
0.2-0.3	7989
0.3-0.4	12388
0.4-0.5	4799
0.5-0.6	6579
0.6-0.7	7029
0.7-0.8	640
0.8-0.85	11
0.85-0.9	7
0.9-0.95	7
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471811
0.9941	High Similarity	NPC195675
0.9941	High Similarity	NPC471808
0.9941	High Similarity	NPC471814
0.9655	High Similarity	NPC471806
0.9655	High Similarity	NPC471810
0.9645	High Similarity	NPC175804
0.9598	High Similarity	NPC121100
0.9598	High Similarity	NPC471813
0.9598	High Similarity	NPC471805
0.9543	High Similarity	NPC471807
0.9429	High Similarity	NPC471812
0.9429	High Similarity	NPC471804
0.9429	High Similarity	NPC471803
0.9375	High Similarity	NPC39409
0.9086	High Similarity	NPC471801
0.908	High Similarity	NPC108278
0.9029	High Similarity	NPC471802
0.8696	High Similarity	NPC214901
0.8641	High Similarity	NPC220369
0.8602	High Similarity	NPC193676
0.8602	High Similarity	NPC198163
0.8511	High Similarity	NPC154720
0.85	High Similarity	NPC28160
0.8278	Intermediate Similarity	NPC188618
0.8142	Intermediate Similarity	NPC45072
0.8132	Intermediate Similarity	NPC470422
0.8057	Intermediate Similarity	NPC471800
0.8023	Intermediate Similarity	NPC238381
0.7892	Intermediate Similarity	NPC477568
0.7869	Intermediate Similarity	NPC148480
0.7845	Intermediate Similarity	NPC300984
0.7845	Intermediate Similarity	NPC156082
0.7842	Intermediate Similarity	NPC474499
0.7836	Intermediate Similarity	NPC200207
0.7833	Intermediate Similarity	NPC303565
0.7814	Intermediate Similarity	NPC472032
0.7802	Intermediate Similarity	NPC267153
0.7802	Intermediate Similarity	NPC112981
0.779	Intermediate Similarity	NPC93739
0.776	Intermediate Similarity	NPC470099
0.776	Intermediate Similarity	NPC20216
0.7747	Intermediate Similarity	NPC284007
0.7722	Intermediate Similarity	NPC83763
0.7722	Intermediate Similarity	NPC168616
0.7717	Intermediate Similarity	NPC272485
0.7717	Intermediate Similarity	NPC292788
0.7709	Intermediate Similarity	NPC54928
0.7708	Intermediate Similarity	NPC136411
0.7705	Intermediate Similarity	NPC8070
0.7692	Intermediate Similarity	NPC474096
0.768	Intermediate Similarity	NPC200594
0.7668	Intermediate Similarity	NPC470100
0.765	Intermediate Similarity	NPC474350
0.764	Intermediate Similarity	NPC289968
0.7637	Intermediate Similarity	NPC298401
0.7634	Intermediate Similarity	NPC20543
0.7634	Intermediate Similarity	NPC246716
0.7634	Intermediate Similarity	NPC239440
0.7634	Intermediate Similarity	NPC17219
0.7609	Intermediate Similarity	NPC58653
0.7609	Intermediate Similarity	NPC173352
0.7596	Intermediate Similarity	NPC473696
0.7594	Intermediate Similarity	NPC474857
0.759	Intermediate Similarity	NPC221185
0.7581	Intermediate Similarity	NPC26568
0.7568	Intermediate Similarity	NPC28669
0.7568	Intermediate Similarity	NPC474061
0.7554	Intermediate Similarity	NPC470081
0.7554	Intermediate Similarity	NPC234004
0.7553	Intermediate Similarity	NPC181523
0.7552	Intermediate Similarity	NPC99937
0.7551	Intermediate Similarity	NPC247104
0.7541	Intermediate Similarity	NPC472405
0.754	Intermediate Similarity	NPC470565
0.754	Intermediate Similarity	NPC10576
0.754	Intermediate Similarity	NPC1827
0.754	Intermediate Similarity	NPC107283
0.754	Intermediate Similarity	NPC470562
0.754	Intermediate Similarity	NPC277865
0.7514	Intermediate Similarity	NPC472456
0.7513	Intermediate Similarity	NPC139350
0.7513	Intermediate Similarity	NPC264922
0.7513	Intermediate Similarity	NPC48822
0.7513	Intermediate Similarity	NPC289147
0.75	Intermediate Similarity	NPC470560
0.75	Intermediate Similarity	NPC8300
0.7487	Intermediate Similarity	NPC99613
0.7487	Intermediate Similarity	NPC49487
0.7486	Intermediate Similarity	NPC66404
0.7486	Intermediate Similarity	NPC95123
0.7485	Intermediate Similarity	NPC475423
0.7473	Intermediate Similarity	NPC472404
0.7473	Intermediate Similarity	NPC472452
0.7473	Intermediate Similarity	NPC300727
0.7473	Intermediate Similarity	NPC217677
0.7473	Intermediate Similarity	NPC241904
0.7473	Intermediate Similarity	NPC29160
0.7473	Intermediate Similarity	NPC165977
0.7472	Intermediate Similarity	NPC328119
0.7459	Intermediate Similarity	NPC29055
0.7459	Intermediate Similarity	NPC20541
0.7458	Intermediate Similarity	NPC477569
0.7448	Intermediate Similarity	NPC151292
0.7447	Intermediate Similarity	NPC109827
0.7447	Intermediate Similarity	NPC124470
0.7443	Intermediate Similarity	NPC134621
0.7436	Intermediate Similarity	NPC316091
0.7433	Intermediate Similarity	NPC234331
0.7432	Intermediate Similarity	NPC476242
0.7423	Intermediate Similarity	NPC191606
0.7419	Intermediate Similarity	NPC68850
0.7419	Intermediate Similarity	NPC85057
0.7419	Intermediate Similarity	NPC130920
0.7418	Intermediate Similarity	NPC274730
0.7407	Intermediate Similarity	NPC158226
0.7401	Intermediate Similarity	NPC237208
0.7396	Intermediate Similarity	NPC306240
0.7396	Intermediate Similarity	NPC113446
0.7394	Intermediate Similarity	NPC165979
0.7394	Intermediate Similarity	NPC163130
0.7391	Intermediate Similarity	NPC474287
0.7391	Intermediate Similarity	NPC56085
0.7391	Intermediate Similarity	NPC14353
0.7391	Intermediate Similarity	NPC228785
0.7391	Intermediate Similarity	NPC475886
0.7389	Intermediate Similarity	NPC226973
0.7389	Intermediate Similarity	NPC308451
0.7389	Intermediate Similarity	NPC204350
0.7389	Intermediate Similarity	NPC208043
0.7387	Intermediate Similarity	NPC313541
0.7377	Intermediate Similarity	NPC108456
0.7374	Intermediate Similarity	NPC477567
0.7374	Intermediate Similarity	NPC477566
0.7371	Intermediate Similarity	NPC105648
0.7363	Intermediate Similarity	NPC108744
0.736	Intermediate Similarity	NPC33265
0.736	Intermediate Similarity	NPC62536
0.7351	Intermediate Similarity	NPC474186
0.7351	Intermediate Similarity	NPC474187
0.7351	Intermediate Similarity	NPC66288
0.7351	Intermediate Similarity	NPC40491
0.7351	Intermediate Similarity	NPC474351
0.7351	Intermediate Similarity	NPC475883
0.7351	Intermediate Similarity	NPC61010
0.7351	Intermediate Similarity	NPC278052
0.7347	Intermediate Similarity	NPC313386
0.7345	Intermediate Similarity	NPC29577
0.7337	Intermediate Similarity	NPC100123
0.7337	Intermediate Similarity	NPC45846
0.7337	Intermediate Similarity	NPC315157
0.7333	Intermediate Similarity	NPC306821
0.7333	Intermediate Similarity	NPC470103
0.7326	Intermediate Similarity	NPC234053
0.7322	Intermediate Similarity	NPC227062
0.7318	Intermediate Similarity	NPC195202
0.7314	Intermediate Similarity	NPC220106
0.7312	Intermediate Similarity	NPC52204
0.7312	Intermediate Similarity	NPC229632
0.7308	Intermediate Similarity	NPC89474
0.7308	Intermediate Similarity	NPC22519
0.7308	Intermediate Similarity	NPC472915
0.7308	Intermediate Similarity	NPC246204
0.7308	Intermediate Similarity	NPC280937
0.7308	Intermediate Similarity	NPC231018
0.7308	Intermediate Similarity	NPC47781
0.7308	Intermediate Similarity	NPC86485
0.7308	Intermediate Similarity	NPC183878
0.7308	Intermediate Similarity	NPC255350
0.7308	Intermediate Similarity	NPC145379
0.7308	Intermediate Similarity	NPC69394
0.7308	Intermediate Similarity	NPC160951
0.7308	Intermediate Similarity	NPC75279
0.7308	Intermediate Similarity	NPC176775
0.7308	Intermediate Similarity	NPC274327
0.7308	Intermediate Similarity	NPC276409
0.7308	Intermediate Similarity	NPC250822
0.7308	Intermediate Similarity	NPC475895
0.7306	Intermediate Similarity	NPC329161
0.7306	Intermediate Similarity	NPC240887
0.7306	Intermediate Similarity	NPC470091
0.7297	Intermediate Similarity	NPC320359
0.7297	Intermediate Similarity	NPC200746
0.7297	Intermediate Similarity	NPC47623
0.7293	Intermediate Similarity	NPC117579
0.7283	Intermediate Similarity	NPC181960
0.7283	Intermediate Similarity	NPC469584
0.7278	Intermediate Similarity	NPC291049
0.7278	Intermediate Similarity	NPC48479
0.7278	Intermediate Similarity	NPC285527
0.7278	Intermediate Similarity	NPC233267
0.7278	Intermediate Similarity	NPC177298
0.7278	Intermediate Similarity	NPC106334
0.7273	Intermediate Similarity	NPC133065
0.7273	Intermediate Similarity	NPC197168
0.7273	Intermediate Similarity	NPC470563
0.7273	Intermediate Similarity	NPC270837
0.7273	Intermediate Similarity	NPC152659
0.7273	Intermediate Similarity	NPC236132
0.7273	Intermediate Similarity	NPC236521

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 NPC471809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	436
0.1-0.2	1412
0.2-0.3	2679
0.3-0.4	2564
0.4-0.5	1408
0.5-0.6	513
0.6-0.7	132
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7401	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2403	Approved
0.7318	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2801	Approved
0.7128	Intermediate Similarity	NPD6232	Discontinued
0.712	Intermediate Similarity	NPD5844	Phase 1
0.7081	Intermediate Similarity	NPD3817	Phase 2
0.7065	Intermediate Similarity	NPD1934	Approved
0.7027	Intermediate Similarity	NPD1465	Phase 2
0.7016	Intermediate Similarity	NPD7473	Discontinued
0.7006	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2534	Approved
0.6961	Remote Similarity	NPD2533	Approved
0.6961	Remote Similarity	NPD2532	Approved
0.6952	Remote Similarity	NPD3882	Suspended
0.6935	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1511	Approved
0.6888	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7819	Suspended
0.6831	Remote Similarity	NPD1512	Approved
0.6788	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6166	Phase 2
0.6788	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7054	Approved
0.6754	Remote Similarity	NPD5494	Approved
0.6735	Remote Similarity	NPD7074	Phase 3
0.6735	Remote Similarity	NPD7472	Approved
0.6721	Remote Similarity	NPD6799	Approved
0.6718	Remote Similarity	NPD3818	Discontinued
0.6685	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7075	Discontinued
0.6649	Remote Similarity	NPD958	Approved
0.6633	Remote Similarity	NPD7808	Phase 3
0.6632	Remote Similarity	NPD6959	Discontinued
0.6616	Remote Similarity	NPD6797	Phase 2
0.6611	Remote Similarity	NPD2935	Discontinued
0.6596	Remote Similarity	NPD6599	Discontinued
0.6593	Remote Similarity	NPD2800	Approved
0.6583	Remote Similarity	NPD7251	Discontinued
0.6579	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD957	Approved
0.6573	Remote Similarity	NPD1184	Approved
0.6573	Remote Similarity	NPD447	Suspended
0.6562	Remote Similarity	NPD3749	Approved
0.6557	Remote Similarity	NPD3750	Approved
0.6545	Remote Similarity	NPD5402	Approved
0.6533	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD919	Approved
0.6526	Remote Similarity	NPD6801	Discontinued
0.6513	Remote Similarity	NPD5711	Approved
0.6513	Remote Similarity	NPD5710	Approved
0.6484	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7411	Suspended
0.6473	Remote Similarity	NPD6312	Discontinued
0.6473	Remote Similarity	NPD4360	Phase 2
0.6473	Remote Similarity	NPD4363	Phase 3
0.6462	Remote Similarity	NPD7199	Phase 2
0.6448	Remote Similarity	NPD1549	Phase 2
0.6444	Remote Similarity	NPD6651	Approved
0.6439	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD2354	Approved
0.6429	Remote Similarity	NPD1551	Phase 2
0.6425	Remote Similarity	NPD7768	Phase 2
0.6425	Remote Similarity	NPD1240	Approved
0.6421	Remote Similarity	NPD4380	Phase 2
0.6417	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD3926	Phase 2
0.6396	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD230	Phase 1
0.6378	Remote Similarity	NPD1247	Approved
0.6374	Remote Similarity	NPD1510	Phase 2
0.6373	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD3226	Approved
0.6364	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4361	Phase 2
0.6364	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6234	Discontinued
0.6354	Remote Similarity	NPD1607	Approved
0.6354	Remote Similarity	NPD37	Approved
0.6349	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD3887	Approved
0.634	Remote Similarity	NPD4967	Phase 2
0.634	Remote Similarity	NPD4965	Approved
0.634	Remote Similarity	NPD4966	Approved
0.6339	Remote Similarity	NPD2796	Approved
0.6304	Remote Similarity	NPD2353	Approved
0.6304	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4628	Phase 3
0.6284	Remote Similarity	NPD3748	Approved
0.6284	Remote Similarity	NPD2799	Discontinued
0.6277	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD920	Approved
0.6263	Remote Similarity	NPD5403	Approved
0.6256	Remote Similarity	NPD6559	Discontinued
0.625	Remote Similarity	NPD4972	Discontinued
0.6243	Remote Similarity	NPD1578	Phase 2
0.6237	Remote Similarity	NPD1243	Approved
0.6236	Remote Similarity	NPD454	Approved
0.623	Remote Similarity	NPD1653	Approved
0.622	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD2346	Discontinued
0.6215	Remote Similarity	NPD1203	Approved
0.6209	Remote Similarity	NPD1933	Approved
0.6205	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD7286	Phase 2
0.6183	Remote Similarity	NPD4534	Discontinued
0.6176	Remote Similarity	NPD3303	Discontinued
0.6168	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD5401	Approved
0.6154	Remote Similarity	NPD943	Approved
0.615	Remote Similarity	NPD5242	Approved
0.615	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7228	Approved
0.6139	Remote Similarity	NPD3751	Discontinued
0.6135	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD5953	Discontinued
0.6122	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.612	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6832	Phase 2
0.61	Remote Similarity	NPD3787	Discontinued
0.6096	Remote Similarity	NPD5958	Discontinued
0.6075	Remote Similarity	NPD6100	Approved
0.6075	Remote Similarity	NPD6099	Approved
0.6073	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD9717	Approved
0.6041	Remote Similarity	NPD5353	Approved
0.604	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7783	Phase 2
0.6022	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD7390	Discontinued
0.602	Remote Similarity	NPD7229	Phase 3
0.6	Remote Similarity	NPD6190	Approved
0.599	Remote Similarity	NPD7549	Discontinued
0.5989	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD422	Phase 1
0.5989	Remote Similarity	NPD3027	Phase 3
0.5981	Remote Similarity	NPD1163	Approved
0.5981	Remote Similarity	NPD6784	Approved
0.5981	Remote Similarity	NPD6785	Approved
0.5978	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD1613	Approved
0.5972	Remote Similarity	NPD4287	Approved
0.5969	Remote Similarity	NPD6385	Approved
0.5969	Remote Similarity	NPD6386	Approved
0.5968	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD4536	Approved
0.5968	Remote Similarity	NPD4538	Approved
0.5962	Remote Similarity	NPD8312	Approved
0.5962	Remote Similarity	NPD8313	Approved
0.596	Remote Similarity	NPD4288	Approved
0.5957	Remote Similarity	NPD2344	Approved
0.5956	Remote Similarity	NPD2313	Discontinued
0.5956	Remote Similarity	NPD411	Approved
0.5956	Remote Similarity	NPD3268	Approved
0.5955	Remote Similarity	NPD1608	Approved
0.5952	Remote Similarity	NPD8434	Phase 2
0.5946	Remote Similarity	NPD8151	Discontinued
0.5944	Remote Similarity	NPD2797	Approved
0.5942	Remote Similarity	NPD7685	Pre-registration
0.5936	Remote Similarity	NPD7435	Discontinued
0.592	Remote Similarity	NPD3365	Discontinued
0.5913	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD5404	Approved
0.5904	Remote Similarity	NPD5405	Approved
0.5904	Remote Similarity	NPD5406	Approved
0.5904	Remote Similarity	NPD5408	Approved
0.5892	Remote Similarity	NPD4060	Phase 1
0.5891	Remote Similarity	NPD8127	Discontinued
0.5885	Remote Similarity	NPD5058	Phase 3
0.5877	Remote Similarity	NPD8150	Discontinued
0.5875	Remote Similarity	NPD1852	Discontinued
0.5872	Remote Similarity	NPD6780	Approved
0.5872	Remote Similarity	NPD6776	Approved
0.5872	Remote Similarity	NPD6782	Approved
0.5872	Remote Similarity	NPD6779	Approved
0.5872	Remote Similarity	NPD6778	Approved
0.5872	Remote Similarity	NPD6781	Approved
0.5872	Remote Similarity	NPD6777	Approved
0.587	Remote Similarity	NPD7985	Registered
0.5867	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.5866	Remote Similarity	NPD9269	Phase 2
0.5865	Remote Similarity	NPD7039	Approved
0.5865	Remote Similarity	NPD7240	Approved
0.5865	Remote Similarity	NPD7038	Approved
0.586	Remote Similarity	NPD5124	Phase 1
0.586	Remote Similarity	NPD5123	Clinical (unspecified phase)

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