NPASS Compound

Structure

NPC471806 OpenBabel07101719242D 28 30 0 0 0 0 0 0 0 0999 V2000 2.7105 1.5794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -4.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2459 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2766 0.6784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8399 -0.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 -3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 -0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4060 -1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 -2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4088 -1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9693 -1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5382 -2.8507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 -2.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -2.0245 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 -3.3799 -2.1235 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.9665 -1.8003 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.1044 -3.7517 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.0988 -3.6022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5984 0.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 -0.1235 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 0.0000 -2.2470 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 26 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 26 1 0 0 0 0 12 18 2 0 0 0 0 12 27 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 28 1 0 0 0 0 19 28 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.03
Volume:	399.936
LogP:	7.081
LogD:	4.637
LogS:	-7.169
# Rotatable Bonds:	5
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	3.23
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:	-5.142
MDCK Permeability:	1.8425285816192627e-05
Pgp-inhibitor:	0.931
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	101.43412017822266%
Volume Distribution (VD):	2.449
Pgp-substrate:	1.199461817741394%

ADMET: Metabolism

CYP1A2-inhibitor:	0.39
CYP1A2-substrate:	0.74
CYP2C19-inhibitor:	0.58
CYP2C19-substrate:	0.296
CYP2C9-inhibitor:	0.849
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.632
CYP3A4-inhibitor:	0.104
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	6.791
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.018
Drug-inuced Liver Injury (DILI):	0.194
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.855
Carcinogencity:	0.282
Eye Corrosion:	0.003
Eye Irritation:	0.833
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC471806

Natural Product ID:	NPC471806
*Common Name:**	Spiromastixone G
IUPAC Name:	2,8,10-trichloro-9-hydroxy-3-methoxy-1,7-dipropylbenzo[b][1,4]benzodioxepin-6-one
Synonyms:
Standard InCHIKey:	WJAVVCUQFJTSCE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19Cl3O5/c1-4-6-9-13-19(16(23)17(24)15(9)22)28-18-10(7-5-2)14(21)11(26-3)8-12(18)27-20(13)25/h8,24H,4-7H2,1-3H3
SMILES:	CCCc1c2Oc3c(C(=O)Oc2cc(c1Cl)OC)c(CCC)c(c(c3Cl)O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234397
PubChem CID:	90670412
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	=	0.5	ug.mL-1	PMID[483620]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	=	0.5	ug.mL-1	PMID[483620]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.25	ug.mL-1	PMID[483620]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[483620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	8000.0	nM	PMID[483620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	4000.0	nM	PMID[483620]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IC50	=	4000.0	nM	PMID[483620]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IC50	=	2000.0	nM	PMID[483620]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IC50	=	128000.0	nM	PMID[483620]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IC50	>	256000.0	nM	PMID[483620]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IC50	=	256000.0	nM	PMID[483620]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IC50	=	256000.0	nM	PMID[483620]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IC50	=	16000.0	nM	PMID[483620]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>	256000.0	nM	PMID[483620]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IC50	>	256000.0	nM	PMID[483620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Ratio IC50	=	2.0	n.a.	PMID[483620]

☑ 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 NPC471806 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	497
0.1-0.2	2503
0.2-0.3	7429
0.3-0.4	12410
0.4-0.5	4096
0.5-0.6	6139
0.6-0.7	7594
0.7-0.8	1961
0.8-0.85	38
0.85-0.9	11
0.9-0.95	4
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471810
0.9942	High Similarity	NPC471805
0.9942	High Similarity	NPC471813
0.9942	High Similarity	NPC121100
0.9885	High Similarity	NPC471807
0.977	High Similarity	NPC471803
0.977	High Similarity	NPC471812
0.977	High Similarity	NPC471804
0.9714	High Similarity	NPC39409
0.9655	High Similarity	NPC471809
0.9655	High Similarity	NPC471811
0.9598	High Similarity	NPC195675
0.9598	High Similarity	NPC471814
0.9598	High Similarity	NPC471808
0.9425	High Similarity	NPC471801
0.9422	High Similarity	NPC108278
0.9368	High Similarity	NPC471802
0.931	High Similarity	NPC175804
0.9016	High Similarity	NPC214901
0.8962	High Similarity	NPC220369
0.8827	High Similarity	NPC28160
0.8824	High Similarity	NPC154720
0.8617	High Similarity	NPC198163
0.8603	High Similarity	NPC188618
0.8462	Intermediate Similarity	NPC45072
0.8453	Intermediate Similarity	NPC470422
0.8421	Intermediate Similarity	NPC193676
0.8391	Intermediate Similarity	NPC471800
0.8352	Intermediate Similarity	NPC238381
0.8167	Intermediate Similarity	NPC156082
0.8167	Intermediate Similarity	NPC300984
0.8156	Intermediate Similarity	NPC303565
0.8148	Intermediate Similarity	NPC474499
0.8132	Intermediate Similarity	NPC472032
0.8122	Intermediate Similarity	NPC112981
0.8122	Intermediate Similarity	NPC267153
0.8111	Intermediate Similarity	NPC93739
0.8077	Intermediate Similarity	NPC20216
0.8066	Intermediate Similarity	NPC284007
0.8063	Intermediate Similarity	NPC470099
0.8045	Intermediate Similarity	NPC83763
0.8045	Intermediate Similarity	NPC168616
0.8034	Intermediate Similarity	NPC54928
0.8033	Intermediate Similarity	NPC272485
0.8033	Intermediate Similarity	NPC292788
0.8022	Intermediate Similarity	NPC8070
0.8011	Intermediate Similarity	NPC474096
0.8	Intermediate Similarity	NPC200594
0.7969	Intermediate Similarity	NPC470100
0.7967	Intermediate Similarity	NPC474350
0.7966	Intermediate Similarity	NPC289968
0.7956	Intermediate Similarity	NPC298401
0.7946	Intermediate Similarity	NPC246716
0.7946	Intermediate Similarity	NPC239440
0.7946	Intermediate Similarity	NPC20543
0.7946	Intermediate Similarity	NPC17219
0.7923	Intermediate Similarity	NPC173352
0.7923	Intermediate Similarity	NPC58653
0.7914	Intermediate Similarity	NPC477568
0.7912	Intermediate Similarity	NPC473696
0.7903	Intermediate Similarity	NPC474857
0.7892	Intermediate Similarity	NPC26568
0.7887	Intermediate Similarity	NPC221185
0.788	Intermediate Similarity	NPC28669
0.788	Intermediate Similarity	NPC474061
0.7869	Intermediate Similarity	NPC234004
0.7869	Intermediate Similarity	NPC470081
0.7861	Intermediate Similarity	NPC181523
0.7857	Intermediate Similarity	NPC472405
0.7853	Intermediate Similarity	NPC99937
0.7849	Intermediate Similarity	NPC470562
0.7849	Intermediate Similarity	NPC1827
0.7849	Intermediate Similarity	NPC277865
0.7849	Intermediate Similarity	NPC470565
0.7849	Intermediate Similarity	NPC10576
0.7849	Intermediate Similarity	NPC107283
0.7846	Intermediate Similarity	NPC247104
0.7833	Intermediate Similarity	NPC472456
0.7819	Intermediate Similarity	NPC264922
0.7819	Intermediate Similarity	NPC289147
0.7819	Intermediate Similarity	NPC139350
0.7816	Intermediate Similarity	NPC95123
0.7816	Intermediate Similarity	NPC66404
0.7814	Intermediate Similarity	NPC8300
0.7807	Intermediate Similarity	NPC470560
0.7806	Intermediate Similarity	NPC48822
0.7797	Intermediate Similarity	NPC328119
0.7796	Intermediate Similarity	NPC99613
0.7796	Intermediate Similarity	NPC49487
0.779	Intermediate Similarity	NPC217677
0.779	Intermediate Similarity	NPC472404
0.779	Intermediate Similarity	NPC165977
0.779	Intermediate Similarity	NPC300727
0.779	Intermediate Similarity	NPC241904
0.7784	Intermediate Similarity	NPC472452
0.7784	Intermediate Similarity	NPC29160
0.7778	Intermediate Similarity	NPC20541
0.7771	Intermediate Similarity	NPC134621
0.7754	Intermediate Similarity	NPC124470
0.7754	Intermediate Similarity	NPC109827
0.7749	Intermediate Similarity	NPC151292
0.7747	Intermediate Similarity	NPC476242
0.7742	Intermediate Similarity	NPC234331
0.7735	Intermediate Similarity	NPC274730
0.7732	Intermediate Similarity	NPC316091
0.7732	Intermediate Similarity	NPC136411
0.773	Intermediate Similarity	NPC130920
0.773	Intermediate Similarity	NPC68850
0.773	Intermediate Similarity	NPC85057
0.7727	Intermediate Similarity	NPC237208
0.772	Intermediate Similarity	NPC191606
0.7713	Intermediate Similarity	NPC158226
0.7709	Intermediate Similarity	NPC208043
0.7709	Intermediate Similarity	NPC308451
0.7709	Intermediate Similarity	NPC226973
0.7709	Intermediate Similarity	NPC204350
0.7705	Intermediate Similarity	NPC228785
0.7705	Intermediate Similarity	NPC56085
0.7705	Intermediate Similarity	NPC475886
0.7705	Intermediate Similarity	NPC14353
0.7705	Intermediate Similarity	NPC474287
0.7701	Intermediate Similarity	NPC165979
0.7701	Intermediate Similarity	NPC148480
0.7701	Intermediate Similarity	NPC105648
0.7701	Intermediate Similarity	NPC163130
0.7696	Intermediate Similarity	NPC306240
0.7696	Intermediate Similarity	NPC113446
0.7692	Intermediate Similarity	NPC108456
0.7684	Intermediate Similarity	NPC62536
0.7684	Intermediate Similarity	NPC33265
0.7677	Intermediate Similarity	NPC313541
0.767	Intermediate Similarity	NPC29577
0.7663	Intermediate Similarity	NPC40491
0.7663	Intermediate Similarity	NPC474186
0.7663	Intermediate Similarity	NPC66288
0.7663	Intermediate Similarity	NPC474351
0.7663	Intermediate Similarity	NPC475883
0.7663	Intermediate Similarity	NPC474187
0.7663	Intermediate Similarity	NPC278052
0.7663	Intermediate Similarity	NPC61010
0.7657	Intermediate Similarity	NPC200207
0.7654	Intermediate Similarity	NPC306821
0.765	Intermediate Similarity	NPC108744
0.765	Intermediate Similarity	NPC45846
0.765	Intermediate Similarity	NPC100123
0.7644	Intermediate Similarity	NPC220106
0.7641	Intermediate Similarity	NPC313386
0.764	Intermediate Similarity	NPC195202
0.7637	Intermediate Similarity	NPC227062
0.7634	Intermediate Similarity	NPC234053
0.7629	Intermediate Similarity	NPC470103
0.7624	Intermediate Similarity	NPC176775
0.7624	Intermediate Similarity	NPC47781
0.7624	Intermediate Similarity	NPC183878
0.7624	Intermediate Similarity	NPC250822
0.7624	Intermediate Similarity	NPC280937
0.7624	Intermediate Similarity	NPC75279
0.7624	Intermediate Similarity	NPC276409
0.7624	Intermediate Similarity	NPC145379
0.7624	Intermediate Similarity	NPC255350
0.7624	Intermediate Similarity	NPC475895
0.7624	Intermediate Similarity	NPC274327
0.7624	Intermediate Similarity	NPC89474
0.7624	Intermediate Similarity	NPC86485
0.7624	Intermediate Similarity	NPC472915
0.7624	Intermediate Similarity	NPC246204
0.7624	Intermediate Similarity	NPC231018
0.7624	Intermediate Similarity	NPC22519
0.7624	Intermediate Similarity	NPC160951
0.7624	Intermediate Similarity	NPC69394
0.7622	Intermediate Similarity	NPC229632
0.7622	Intermediate Similarity	NPC52204
0.7611	Intermediate Similarity	NPC117579
0.7609	Intermediate Similarity	NPC47623
0.7609	Intermediate Similarity	NPC320359
0.7609	Intermediate Similarity	NPC200746
0.7604	Intermediate Similarity	NPC329161
0.7604	Intermediate Similarity	NPC470091
0.7604	Intermediate Similarity	NPC240887
0.7598	Intermediate Similarity	NPC106334
0.7598	Intermediate Similarity	NPC291049
0.7598	Intermediate Similarity	NPC233267
0.7598	Intermediate Similarity	NPC48479
0.7598	Intermediate Similarity	NPC177298
0.7598	Intermediate Similarity	NPC285527
0.7596	Intermediate Similarity	NPC181960
0.7596	Intermediate Similarity	NPC469584
0.7584	Intermediate Similarity	NPC12305
0.7584	Intermediate Similarity	NPC119660
0.7584	Intermediate Similarity	NPC12200
0.7584	Intermediate Similarity	NPC93034
0.7582	Intermediate Similarity	NPC4455
0.7582	Intermediate Similarity	NPC37392
0.7582	Intermediate Similarity	NPC201136
0.7582	Intermediate Similarity	NPC213622
0.7582	Intermediate Similarity	NPC20830
0.7582	Intermediate Similarity	NPC183597
0.7582	Intermediate Similarity	NPC138360
0.7582	Intermediate Similarity	NPC280339
0.7582	Intermediate Similarity	NPC146165

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 NPC471806 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	1229
0.2-0.3	2367
0.3-0.4	2690
0.4-0.5	1522
0.5-0.6	686
0.6-0.7	199
0.7-0.8	21
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
0.764	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD2403	Approved
0.7627	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD2801	Approved
0.7433	Intermediate Similarity	NPD6232	Discontinued
0.7421	Intermediate Similarity	NPD5844	Phase 1
0.7391	Intermediate Similarity	NPD3817	Phase 2
0.7377	Intermediate Similarity	NPD1934	Approved
0.7337	Intermediate Similarity	NPD1465	Phase 2
0.733	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7473	Discontinued
0.7258	Intermediate Similarity	NPD3882	Suspended
0.7243	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1511	Approved
0.7179	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD1512	Approved
0.7083	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6166	Phase 2
0.7062	Intermediate Similarity	NPD7054	Approved
0.7053	Intermediate Similarity	NPD5494	Approved
0.7033	Intermediate Similarity	NPD6799	Approved
0.7026	Intermediate Similarity	NPD7074	Phase 3
0.7026	Intermediate Similarity	NPD7472	Approved
0.701	Intermediate Similarity	NPD3818	Discontinued
0.6995	Remote Similarity	NPD2533	Approved
0.6995	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2532	Approved
0.6995	Remote Similarity	NPD2534	Approved
0.6952	Remote Similarity	NPD958	Approved
0.6947	Remote Similarity	NPD7075	Discontinued
0.6927	Remote Similarity	NPD6959	Discontinued
0.6927	Remote Similarity	NPD2935	Discontinued
0.6919	Remote Similarity	NPD7808	Phase 3
0.6904	Remote Similarity	NPD6797	Phase 2
0.6898	Remote Similarity	NPD6599	Discontinued
0.6893	Remote Similarity	NPD1184	Approved
0.6893	Remote Similarity	NPD447	Suspended
0.6882	Remote Similarity	NPD957	Approved
0.6878	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7251	Discontinued
0.6868	Remote Similarity	NPD3750	Approved
0.6859	Remote Similarity	NPD3749	Approved
0.6842	Remote Similarity	NPD5402	Approved
0.6825	Remote Similarity	NPD6801	Discontinued
0.6823	Remote Similarity	NPD919	Approved
0.6818	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7411	Suspended
0.6771	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD1549	Phase 2
0.6753	Remote Similarity	NPD7199	Phase 2
0.6748	Remote Similarity	NPD4363	Phase 3
0.6748	Remote Similarity	NPD4360	Phase 2
0.6742	Remote Similarity	NPD1240	Approved
0.674	Remote Similarity	NPD1551	Phase 2
0.6739	Remote Similarity	NPD2354	Approved
0.6723	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4380	Phase 2
0.6719	Remote Similarity	NPD7768	Phase 2
0.6716	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD230	Phase 1
0.6685	Remote Similarity	NPD1510	Phase 2
0.6684	Remote Similarity	NPD3926	Phase 2
0.6684	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD6312	Discontinued
0.665	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6234	Discontinued
0.6649	Remote Similarity	NPD37	Approved
0.6649	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3887	Approved
0.6648	Remote Similarity	NPD2796	Approved
0.6635	Remote Similarity	NPD4361	Phase 2
0.6635	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4967	Phase 2
0.6632	Remote Similarity	NPD4965	Approved
0.6632	Remote Similarity	NPD4966	Approved
0.6631	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2800	Approved
0.6612	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD2353	Approved
0.6595	Remote Similarity	NPD4628	Phase 3
0.6593	Remote Similarity	NPD2799	Discontinued
0.6593	Remote Similarity	NPD3748	Approved
0.6578	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5403	Approved
0.6561	Remote Similarity	NPD920	Approved
0.6554	Remote Similarity	NPD454	Approved
0.655	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5711	Approved
0.6548	Remote Similarity	NPD5710	Approved
0.6545	Remote Similarity	NPD4972	Discontinued
0.6543	Remote Similarity	NPD1578	Phase 2
0.6541	Remote Similarity	NPD1243	Approved
0.6535	Remote Similarity	NPD6559	Discontinued
0.6534	Remote Similarity	NPD1203	Approved
0.6526	Remote Similarity	NPD1653	Approved
0.6519	Remote Similarity	NPD1933	Approved
0.6505	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD651	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4534	Discontinued
0.6468	Remote Similarity	NPD7286	Phase 2
0.6464	Remote Similarity	NPD943	Approved
0.6455	Remote Similarity	NPD5401	Approved
0.6453	Remote Similarity	NPD3303	Discontinued
0.6452	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5242	Approved
0.6432	Remote Similarity	NPD2346	Discontinued
0.6429	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6832	Phase 2
0.6418	Remote Similarity	NPD7228	Approved
0.6418	Remote Similarity	NPD3751	Discontinued
0.6417	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5953	Discontinued
0.6398	Remote Similarity	NPD5958	Discontinued
0.6382	Remote Similarity	NPD3787	Discontinued
0.6378	Remote Similarity	NPD6099	Approved
0.6378	Remote Similarity	NPD6100	Approved
0.6369	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9717	Approved
0.6349	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5353	Approved
0.6324	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7390	Discontinued
0.6307	Remote Similarity	NPD422	Phase 1
0.6304	Remote Similarity	NPD6651	Approved
0.63	Remote Similarity	NPD7229	Phase 3
0.6298	Remote Similarity	NPD3027	Phase 3
0.6296	Remote Similarity	NPD6190	Approved
0.629	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7783	Phase 2
0.6284	Remote Similarity	NPD1613	Approved
0.6284	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD1608	Approved
0.627	Remote Similarity	NPD4538	Approved
0.627	Remote Similarity	NPD4536	Approved
0.627	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD411	Approved
0.6264	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD3268	Approved
0.6262	Remote Similarity	NPD7549	Discontinued
0.6257	Remote Similarity	NPD2797	Approved
0.6257	Remote Similarity	NPD2344	Approved
0.6256	Remote Similarity	NPD6386	Approved
0.6256	Remote Similarity	NPD6385	Approved
0.625	Remote Similarity	NPD6784	Approved
0.625	Remote Similarity	NPD6785	Approved
0.625	Remote Similarity	NPD1163	Approved
0.6244	Remote Similarity	NPD4288	Approved
0.6232	Remote Similarity	NPD8312	Approved
0.6232	Remote Similarity	NPD8313	Approved
0.622	Remote Similarity	NPD8434	Phase 2
0.6214	Remote Similarity	NPD7685	Pre-registration
0.62	Remote Similarity	NPD3365	Discontinued
0.6199	Remote Similarity	NPD8151	Discontinued
0.6198	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4060	Phase 1
0.6193	Remote Similarity	NPD7435	Discontinued
0.6184	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.618	Remote Similarity	NPD9269	Phase 2
0.6178	Remote Similarity	NPD5058	Phase 3
0.6175	Remote Similarity	NPD2313	Discontinued
0.6169	Remote Similarity	NPD8127	Discontinued
0.6161	Remote Similarity	NPD4287	Approved
0.6154	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.615	Remote Similarity	NPD4308	Phase 3
0.615	Remote Similarity	NPD5588	Approved
0.615	Remote Similarity	NPD5960	Phase 3
0.615	Remote Similarity	NPD7033	Discontinued
0.6143	Remote Similarity	NPD8150	Discontinued
0.6141	Remote Similarity	NPD6233	Phase 2
0.6136	Remote Similarity	NPD9268	Approved
0.6135	Remote Similarity	NPD7039	Approved
0.6135	Remote Similarity	NPD7240	Approved
0.6135	Remote Similarity	NPD7038	Approved
0.6129	Remote Similarity	NPD6781	Approved
0.6129	Remote Similarity	NPD6778	Approved
0.6129	Remote Similarity	NPD6780	Approved
0.6129	Remote Similarity	NPD6782	Approved
0.6129	Remote Similarity	NPD6777	Approved
0.6129	Remote Similarity	NPD6779	Approved
0.6129	Remote Similarity	NPD6776	Approved
0.6126	Remote Similarity	NPD2309	Approved
0.6117	Remote Similarity	NPD5405	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