NPASS Compound

Structure

CID195675 OpenBabel06191715582D 25 27 0 0 0 0 0 0 0 0999 V2000 -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 4.2459 -0.6235 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 -1.4088 -1.1235 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 2.5139 -1.6235 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 1.6479 -0.1235 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 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 -0.9749 -0.2225 0.0000 C 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 3.3799 -2.1235 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 1.6479 0.8765 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 -2.2470 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 23 1 0 0 0 0 4 6 2 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 14 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 13 2 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 15 2 0 0 0 0 12 24 1 0 0 0 0 13 24 1 0 0 0 0 14 23 1 0 0 0 0 15 25 1 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	421.93
Volume:	345.963
LogP:	6.215
LogD:	3.543
LogS:	-6.475
# Rotatable Bonds:	1
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	3.293
Fsp3:	0.188
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:	-4.86
MDCK Permeability:	2.0111518097110093e-05
Pgp-inhibitor:	0.115
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.181
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	102.07161712646484%
Volume Distribution (VD):	1.114
Pgp-substrate:	1.289188027381897%

ADMET: Metabolism

CYP1A2-inhibitor:	0.354
CYP1A2-substrate:	0.843
CYP2C19-inhibitor:	0.384
CYP2C19-substrate:	0.413
CYP2C9-inhibitor:	0.904
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.382

ADMET: Excretion

Clearance (CL):	7.398
Half-life (T1/2):	0.15

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.395
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.889
Carcinogencity:	0.551
Eye Corrosion:	0.003
Eye Irritation:	0.937
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC195675

Natural Product ID:	NPC195675
*Common Name:**	Diploicin
IUPAC Name:	2,4,8,10-tetrachloro-9-hydroxy-3-methoxy-1,7-dimethylbenzo[b][1,4]benzodioxepin-6-one
Synonyms:	Diploicin
Standard InCHIKey:	AXZCNBVMHHTPKA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H10Cl4O5/c1-4-6-13(9(19)11(21)7(4)17)24-12-5(2)8(18)14(23-3)10(20)15(12)25-16(6)22/h21H,1-3H3
SMILES:	COc1c(Cl)c2OC(=O)c3c(Oc2c(c1Cl)C)c(Cl)c(c(c3C)Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079645
PubChem CID:	68244
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
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678669]
NPO13590	Diploicia canescens	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919064]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24094434]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6208	Trichogoniopsis morii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13590	Diploicia canescens	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8523	Haematoxylon campechianum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5477	Mycosphaerella laricina	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	=	4000.0	nM	PMID[552744]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	>	10000.0	nM	PMID[552744]

☑ 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 NPC195675 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	494
0.1-0.2	2927
0.2-0.3	8412
0.3-0.4	12028
0.4-0.5	4733
0.5-0.6	6593
0.6-0.7	6865
0.7-0.8	607
0.8-0.85	12
0.85-0.9	8
0.9-0.95	6
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9941	High Similarity	NPC471809
0.9941	High Similarity	NPC471811
0.9882	High Similarity	NPC471808
0.9882	High Similarity	NPC471814
0.9702	High Similarity	NPC175804
0.9653	High Similarity	NPC121100
0.9598	High Similarity	NPC471810
0.9598	High Similarity	NPC471806
0.954	High Similarity	NPC471805
0.954	High Similarity	NPC471813
0.9486	High Similarity	NPC471807
0.9371	High Similarity	NPC471803
0.9371	High Similarity	NPC471812
0.9371	High Similarity	NPC471804
0.9318	High Similarity	NPC39409
0.9133	High Similarity	NPC108278
0.9029	High Similarity	NPC471801
0.8971	High Similarity	NPC471802
0.8689	High Similarity	NPC220369
0.8641	High Similarity	NPC214901
0.8548	High Similarity	NPC198163
0.8548	High Similarity	NPC193676
0.8457	Intermediate Similarity	NPC154720
0.8444	Intermediate Similarity	NPC28160
0.8222	Intermediate Similarity	NPC188618
0.8177	Intermediate Similarity	NPC470422
0.8087	Intermediate Similarity	NPC45072
0.8	Intermediate Similarity	NPC471800
0.7966	Intermediate Similarity	NPC238381
0.7838	Intermediate Similarity	NPC477568
0.7814	Intermediate Similarity	NPC148480
0.779	Intermediate Similarity	NPC300984
0.779	Intermediate Similarity	NPC156082
0.7789	Intermediate Similarity	NPC474499
0.7778	Intermediate Similarity	NPC303565
0.7778	Intermediate Similarity	NPC200207
0.776	Intermediate Similarity	NPC472032
0.7747	Intermediate Similarity	NPC112981
0.7747	Intermediate Similarity	NPC267153
0.7735	Intermediate Similarity	NPC93739
0.7722	Intermediate Similarity	NPC200594
0.7708	Intermediate Similarity	NPC470099
0.7705	Intermediate Similarity	NPC20216
0.7692	Intermediate Similarity	NPC284007
0.7667	Intermediate Similarity	NPC168616
0.7667	Intermediate Similarity	NPC83763
0.7663	Intermediate Similarity	NPC292788
0.7663	Intermediate Similarity	NPC272485
0.7656	Intermediate Similarity	NPC136411
0.7654	Intermediate Similarity	NPC54928
0.765	Intermediate Similarity	NPC8070
0.7637	Intermediate Similarity	NPC474096
0.7634	Intermediate Similarity	NPC474857
0.7622	Intermediate Similarity	NPC26568
0.7617	Intermediate Similarity	NPC470100
0.7596	Intermediate Similarity	NPC474350
0.7584	Intermediate Similarity	NPC289968
0.7582	Intermediate Similarity	NPC298401
0.7581	Intermediate Similarity	NPC107283
0.7581	Intermediate Similarity	NPC239440
0.7581	Intermediate Similarity	NPC20543
0.7581	Intermediate Similarity	NPC246716
0.7581	Intermediate Similarity	NPC10576
0.7581	Intermediate Similarity	NPC277865
0.7581	Intermediate Similarity	NPC1827
0.7581	Intermediate Similarity	NPC17219
0.7554	Intermediate Similarity	NPC58653
0.7554	Intermediate Similarity	NPC173352
0.7553	Intermediate Similarity	NPC264922
0.7541	Intermediate Similarity	NPC473696
0.7538	Intermediate Similarity	NPC221185
0.7529	Intermediate Similarity	NPC475423
0.7514	Intermediate Similarity	NPC28669
0.7514	Intermediate Similarity	NPC29160
0.7514	Intermediate Similarity	NPC474061
0.75	Intermediate Similarity	NPC234004
0.75	Intermediate Similarity	NPC20541
0.75	Intermediate Similarity	NPC99937
0.75	Intermediate Similarity	NPC247104
0.75	Intermediate Similarity	NPC470081
0.75	Intermediate Similarity	NPC181523
0.7487	Intermediate Similarity	NPC470565
0.7487	Intermediate Similarity	NPC470562
0.7486	Intermediate Similarity	NPC472405
0.7473	Intermediate Similarity	NPC234331
0.7462	Intermediate Similarity	NPC48822
0.746	Intermediate Similarity	NPC289147
0.746	Intermediate Similarity	NPC139350
0.7459	Intermediate Similarity	NPC472456
0.7447	Intermediate Similarity	NPC470560
0.7446	Intermediate Similarity	NPC8300
0.7433	Intermediate Similarity	NPC99613
0.7433	Intermediate Similarity	NPC165979
0.7433	Intermediate Similarity	NPC49487
0.7433	Intermediate Similarity	NPC163130
0.743	Intermediate Similarity	NPC204350
0.7429	Intermediate Similarity	NPC66404
0.7429	Intermediate Similarity	NPC95123
0.7419	Intermediate Similarity	NPC472452
0.7418	Intermediate Similarity	NPC472404
0.7418	Intermediate Similarity	NPC241904
0.7418	Intermediate Similarity	NPC300727
0.7418	Intermediate Similarity	NPC217677
0.7418	Intermediate Similarity	NPC165977
0.7416	Intermediate Similarity	NPC328119
0.7414	Intermediate Similarity	NPC105648
0.7405	Intermediate Similarity	NPC29055
0.7401	Intermediate Similarity	NPC477569
0.7396	Intermediate Similarity	NPC151292
0.7394	Intermediate Similarity	NPC109827
0.7394	Intermediate Similarity	NPC124470
0.7386	Intermediate Similarity	NPC134621
0.7385	Intermediate Similarity	NPC313386
0.7385	Intermediate Similarity	NPC316091
0.7377	Intermediate Similarity	NPC476242
0.7374	Intermediate Similarity	NPC306821
0.7371	Intermediate Similarity	NPC191606
0.7366	Intermediate Similarity	NPC130920
0.7366	Intermediate Similarity	NPC68850
0.7366	Intermediate Similarity	NPC85057
0.7363	Intermediate Similarity	NPC227062
0.7363	Intermediate Similarity	NPC274730
0.7356	Intermediate Similarity	NPC220106
0.7354	Intermediate Similarity	NPC158226
0.7345	Intermediate Similarity	NPC237208
0.7344	Intermediate Similarity	NPC240887
0.7344	Intermediate Similarity	NPC329161
0.7344	Intermediate Similarity	NPC113446
0.7344	Intermediate Similarity	NPC306240
0.7344	Intermediate Similarity	NPC470091
0.7337	Intermediate Similarity	NPC56085
0.7337	Intermediate Similarity	NPC474287
0.7337	Intermediate Similarity	NPC228785
0.7337	Intermediate Similarity	NPC14353
0.7337	Intermediate Similarity	NPC475886
0.7337	Intermediate Similarity	NPC313541
0.7333	Intermediate Similarity	NPC308451
0.7333	Intermediate Similarity	NPC208043
0.7333	Intermediate Similarity	NPC117579
0.7333	Intermediate Similarity	NPC226973
0.7322	Intermediate Similarity	NPC108456
0.7318	Intermediate Similarity	NPC477566
0.7318	Intermediate Similarity	NPC477567
0.7313	Intermediate Similarity	NPC108744
0.7303	Intermediate Similarity	NPC33265
0.7303	Intermediate Similarity	NPC12200
0.7303	Intermediate Similarity	NPC62536
0.7297	Intermediate Similarity	NPC474186
0.7297	Intermediate Similarity	NPC66288
0.7297	Intermediate Similarity	NPC40491
0.7297	Intermediate Similarity	NPC475883
0.7297	Intermediate Similarity	NPC474351
0.7297	Intermediate Similarity	NPC474187
0.7297	Intermediate Similarity	NPC61010
0.7297	Intermediate Similarity	NPC278052
0.7293	Intermediate Similarity	NPC222830
0.7293	Intermediate Similarity	NPC212678
0.7293	Intermediate Similarity	NPC83508
0.7293	Intermediate Similarity	NPC241498
0.7293	Intermediate Similarity	NPC275836
0.7293	Intermediate Similarity	NPC71334
0.7293	Intermediate Similarity	NPC198826
0.7293	Intermediate Similarity	NPC156222
0.7293	Intermediate Similarity	NPC293183
0.7293	Intermediate Similarity	NPC142540
0.7293	Intermediate Similarity	NPC188203
0.7293	Intermediate Similarity	NPC100887
0.7293	Intermediate Similarity	NPC131624
0.7293	Intermediate Similarity	NPC301123
0.7293	Intermediate Similarity	NPC301323
0.7293	Intermediate Similarity	NPC187498
0.7293	Intermediate Similarity	NPC162313
0.7293	Intermediate Similarity	NPC275722
0.7293	Intermediate Similarity	NPC239128
0.7293	Intermediate Similarity	NPC57030
0.7293	Intermediate Similarity	NPC256283
0.7293	Intermediate Similarity	NPC120163
0.7293	Intermediate Similarity	NPC25270
0.7288	Intermediate Similarity	NPC472917
0.7288	Intermediate Similarity	NPC29577
0.7283	Intermediate Similarity	NPC315157
0.7283	Intermediate Similarity	NPC40702
0.7283	Intermediate Similarity	NPC37502
0.7283	Intermediate Similarity	NPC267627
0.7283	Intermediate Similarity	NPC45846
0.7283	Intermediate Similarity	NPC100123
0.7282	Intermediate Similarity	NPC470103
0.7278	Intermediate Similarity	NPC179183
0.7273	Intermediate Similarity	NPC234053
0.7263	Intermediate Similarity	NPC195202
0.7263	Intermediate Similarity	NPC120464
0.7258	Intermediate Similarity	NPC229632
0.7258	Intermediate Similarity	NPC52204
0.7258	Intermediate Similarity	NPC294965
0.7253	Intermediate Similarity	NPC145379
0.7253	Intermediate Similarity	NPC89474
0.7253	Intermediate Similarity	NPC276409
0.7253	Intermediate Similarity	NPC475895
0.7253	Intermediate Similarity	NPC69394
0.7253	Intermediate Similarity	NPC160951

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 NPC195675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	452
0.1-0.2	1445
0.2-0.3	2721
0.3-0.4	2519
0.4-0.5	1371
0.5-0.6	501
0.6-0.7	134
0.7-0.8	7
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
0.7443	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2403	Approved
0.7263	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD2801	Approved
0.7104	Intermediate Similarity	NPD1934	Approved
0.7074	Intermediate Similarity	NPD6232	Discontinued
0.7068	Intermediate Similarity	NPD5844	Phase 1
0.7065	Intermediate Similarity	NPD1465	Phase 2
0.7045	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3817	Phase 2
0.6963	Remote Similarity	NPD7473	Discontinued
0.6944	Remote Similarity	NPD1511	Approved
0.6906	Remote Similarity	NPD2533	Approved
0.6906	Remote Similarity	NPD2532	Approved
0.6906	Remote Similarity	NPD2534	Approved
0.6898	Remote Similarity	NPD3882	Suspended
0.6882	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD1512	Approved
0.6837	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7819	Suspended
0.6736	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6166	Phase 2
0.6718	Remote Similarity	NPD7054	Approved
0.6702	Remote Similarity	NPD5494	Approved
0.6684	Remote Similarity	NPD958	Approved
0.6684	Remote Similarity	NPD7472	Approved
0.6684	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD6799	Approved
0.663	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2800	Approved
0.6613	Remote Similarity	NPD957	Approved
0.661	Remote Similarity	NPD447	Suspended
0.661	Remote Similarity	NPD1184	Approved
0.6597	Remote Similarity	NPD3749	Approved
0.6597	Remote Similarity	NPD7075	Discontinued
0.6593	Remote Similarity	NPD3750	Approved
0.6583	Remote Similarity	NPD7808	Phase 3
0.658	Remote Similarity	NPD6959	Discontinued
0.6566	Remote Similarity	NPD6797	Phase 2
0.6562	Remote Similarity	NPD919	Approved
0.6556	Remote Similarity	NPD2935	Discontinued
0.6543	Remote Similarity	NPD6599	Discontinued
0.6533	Remote Similarity	NPD7251	Discontinued
0.6526	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD5402	Approved
0.6484	Remote Similarity	NPD1549	Phase 2
0.6482	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6801	Discontinued
0.6467	Remote Similarity	NPD2354	Approved
0.6464	Remote Similarity	NPD1551	Phase 2
0.6462	Remote Similarity	NPD5711	Approved
0.6462	Remote Similarity	NPD5710	Approved
0.6461	Remote Similarity	NPD1240	Approved
0.6425	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4363	Phase 3
0.6425	Remote Similarity	NPD230	Phase 1
0.6425	Remote Similarity	NPD4360	Phase 2
0.6425	Remote Similarity	NPD6312	Discontinued
0.6421	Remote Similarity	NPD7411	Suspended
0.641	Remote Similarity	NPD1247	Approved
0.641	Remote Similarity	NPD7199	Phase 2
0.6409	Remote Similarity	NPD1510	Phase 2
0.6402	Remote Similarity	NPD3226	Approved
0.639	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6651	Approved
0.6389	Remote Similarity	NPD1607	Approved
0.6373	Remote Similarity	NPD7768	Phase 2
0.6368	Remote Similarity	NPD4380	Phase 2
0.6364	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD3926	Phase 2
0.6339	Remote Similarity	NPD2353	Approved
0.6339	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD3748	Approved
0.6316	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4361	Phase 2
0.6313	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6234	Discontinued
0.6302	Remote Similarity	NPD37	Approved
0.6296	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD920	Approved
0.629	Remote Similarity	NPD3887	Approved
0.6289	Remote Similarity	NPD4967	Phase 2
0.6289	Remote Similarity	NPD4966	Approved
0.6289	Remote Similarity	NPD4965	Approved
0.6284	Remote Similarity	NPD2796	Approved
0.6277	Remote Similarity	NPD1578	Phase 2
0.6271	Remote Similarity	NPD454	Approved
0.627	Remote Similarity	NPD1243	Approved
0.625	Remote Similarity	NPD2346	Discontinued
0.625	Remote Similarity	NPD1203	Approved
0.6243	Remote Similarity	NPD1933	Approved
0.6237	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4628	Phase 3
0.623	Remote Similarity	NPD2799	Discontinued
0.623	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5403	Approved
0.6207	Remote Similarity	NPD6559	Discontinued
0.6198	Remote Similarity	NPD4972	Discontinued
0.619	Remote Similarity	NPD5401	Approved
0.6188	Remote Similarity	NPD943	Approved
0.6178	Remote Similarity	NPD1653	Approved
0.6172	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD3751	Discontinued
0.6154	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7286	Phase 2
0.6129	Remote Similarity	NPD4534	Discontinued
0.6127	Remote Similarity	NPD3303	Discontinued
0.6121	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD642	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5242	Approved
0.6096	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD7228	Approved
0.6089	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD643	Clinical (unspecified phase)
0.608	Remote Similarity	NPD9717	Approved
0.6078	Remote Similarity	NPD5953	Discontinued
0.6071	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD6832	Phase 2
0.6056	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.605	Remote Similarity	NPD3787	Discontinued
0.6043	Remote Similarity	NPD5958	Discontinued
0.6023	Remote Similarity	NPD422	Phase 1
0.6022	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6099	Approved
0.6022	Remote Similarity	NPD6100	Approved
0.6011	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD1613	Approved
0.601	Remote Similarity	NPD1163	Approved
0.6	Remote Similarity	NPD4287	Approved
0.5991	Remote Similarity	NPD7783	Phase 2
0.5991	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.599	Remote Similarity	NPD4288	Approved
0.599	Remote Similarity	NPD5353	Approved
0.599	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD2313	Discontinued
0.5989	Remote Similarity	NPD1608	Approved
0.5989	Remote Similarity	NPD2344	Approved
0.5989	Remote Similarity	NPD411	Approved
0.597	Remote Similarity	NPD7229	Phase 3
0.5969	Remote Similarity	NPD7390	Discontinued
0.5947	Remote Similarity	NPD6190	Approved
0.5942	Remote Similarity	NPD7549	Discontinued
0.5934	Remote Similarity	NPD3027	Phase 3
0.5933	Remote Similarity	NPD6785	Approved
0.5933	Remote Similarity	NPD6784	Approved
0.5918	Remote Similarity	NPD6385	Approved
0.5918	Remote Similarity	NPD6386	Approved
0.5914	Remote Similarity	NPD4536	Approved
0.5914	Remote Similarity	NPD4538	Approved
0.5914	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD8312	Approved
0.5913	Remote Similarity	NPD8313	Approved
0.5905	Remote Similarity	NPD8434	Phase 2
0.5902	Remote Similarity	NPD3268	Approved
0.5901	Remote Similarity	NPD8151	Discontinued
0.59	Remote Similarity	NPD1852	Discontinued
0.5899	Remote Similarity	NPD9269	Phase 2
0.5894	Remote Similarity	NPD7685	Pre-registration
0.589	Remote Similarity	NPD7435	Discontinued
0.5889	Remote Similarity	NPD2797	Approved
0.5882	Remote Similarity	NPD4308	Phase 3
0.5871	Remote Similarity	NPD3365	Discontinued
0.5865	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD2309	Approved
0.5855	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD9268	Approved
0.5851	Remote Similarity	NPD5405	Approved
0.5851	Remote Similarity	NPD5404	Approved
0.5851	Remote Similarity	NPD5406	Approved
0.5851	Remote Similarity	NPD5408	Approved
0.5842	Remote Similarity	NPD8127	Discontinued
0.5838	Remote Similarity	NPD4060	Phase 1
0.5833	Remote Similarity	NPD5058	Phase 3
0.5833	Remote Similarity	NPD3225	Approved
0.5829	Remote Similarity	NPD8150	Discontinued
0.5826	Remote Similarity	NPD6776	Approved
0.5826	Remote Similarity	NPD6782	Approved
0.5826	Remote Similarity	NPD6779	Approved
0.5826	Remote Similarity	NPD6781	Approved
0.5826	Remote Similarity	NPD6777	Approved
0.5826	Remote Similarity	NPD6778	Approved
0.5826	Remote Similarity	NPD6780	Approved
0.5824	Remote Similarity	NPD9494	Approved
0.5819	Remote Similarity	NPD17	Approved
0.5817	Remote Similarity	NPD7240	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