NPASS Compound

Structure

CID108278 OpenBabel06191715462D 24 26 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 -4.0960 3.5275 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 -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 -2.4060 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 -0.9749 2.0245 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 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 -2.9693 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 0.7818 1.6235 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 -1.5984 -0.5593 0.0000 O 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 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 7 1 0 0 0 0 2 8 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 16 2 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 23 1 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.02
Volume:	332.837
LogP:	5.468
LogD:	4.199
LogS:	-7.677
# Rotatable Bonds:	2
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	2.935
Fsp3:	0.235
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:	-4.969
MDCK Permeability:	2.2339203496812843e-05
Pgp-inhibitor:	0.043
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	100.5281753540039%
Volume Distribution (VD):	0.581
Pgp-substrate:	1.6303952932357788%

ADMET: Metabolism

CYP1A2-inhibitor:	0.465
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.885
CYP2C19-substrate:	0.661
CYP2C9-inhibitor:	0.902
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.372
CYP3A4-substrate:	0.529

ADMET: Excretion

Clearance (CL):	9.761
Half-life (T1/2):	0.199

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.017
Drug-inuced Liver Injury (DILI):	0.795
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.87
Maximum Recommended Daily Dose:	0.879
Skin Sensitization:	0.846
Carcinogencity:	0.512
Eye Corrosion:	0.023
Eye Irritation:	0.953
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC108278

Natural Product ID:	NPC108278
*Common Name:**	Scensidin
IUPAC Name:	2,8-dichloro-3,9-dimethoxy-1,7-dimethylbenzo[b][1,4]benzodioxepin-6-one
Synonyms:	Scensidin
Standard InCHIKey:	AYDBBWJGHVYDQE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14Cl2O5/c1-7-13-9(5-10(21-3)14(7)18)23-16-8(2)15(19)11(22-4)6-12(16)24-17(13)20/h5-6H,1-4H3
SMILES:	COc1cc2OC(=O)c3c(Oc2c(c1Cl)C)cc(c(c3C)Cl)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081411
PubChem CID:	14805248
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]
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]
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]

☑ 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	=	400.0	nM	PMID[570030]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	=	6100.0	nM	PMID[570030]

☑ 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 NPC108278 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	581
0.1-0.2	2698
0.2-0.3	8183
0.3-0.4	11733
0.4-0.5	4037
0.5-0.6	6450
0.6-0.7	7400
0.7-0.8	1569
0.8-0.85	17
0.85-0.9	10
0.9-0.95	18
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9477	High Similarity	NPC121100
0.9422	High Similarity	NPC471806
0.9422	High Similarity	NPC471810
0.9419	High Similarity	NPC471803
0.9405	High Similarity	NPC175804
0.9364	High Similarity	NPC471805
0.9364	High Similarity	NPC471813
0.931	High Similarity	NPC471807
0.9294	High Similarity	NPC471801
0.9195	High Similarity	NPC471812
0.9195	High Similarity	NPC471804
0.9143	High Similarity	NPC39409
0.9133	High Similarity	NPC195675
0.908	High Similarity	NPC471809
0.908	High Similarity	NPC471811
0.9023	High Similarity	NPC471814
0.9023	High Similarity	NPC471808
0.9012	High Similarity	NPC471802
0.8933	High Similarity	NPC220369
0.8883	High Similarity	NPC214901
0.8689	High Similarity	NPC154720
0.8478	Intermediate Similarity	NPC198163
0.8475	Intermediate Similarity	NPC28160
0.8457	Intermediate Similarity	NPC188618
0.828	Intermediate Similarity	NPC193676
0.8235	Intermediate Similarity	NPC471800
0.8202	Intermediate Similarity	NPC470422
0.8198	Intermediate Similarity	NPC238381
0.8111	Intermediate Similarity	NPC45072
0.8011	Intermediate Similarity	NPC156082
0.8011	Intermediate Similarity	NPC300984
0.8	Intermediate Similarity	NPC303565
0.7978	Intermediate Similarity	NPC472032
0.7966	Intermediate Similarity	NPC112981
0.7966	Intermediate Similarity	NPC234053
0.7966	Intermediate Similarity	NPC267153
0.7955	Intermediate Similarity	NPC93739
0.7943	Intermediate Similarity	NPC200594
0.7921	Intermediate Similarity	NPC20216
0.7914	Intermediate Similarity	NPC470099
0.791	Intermediate Similarity	NPC284007
0.7895	Intermediate Similarity	NPC29056
0.7886	Intermediate Similarity	NPC83763
0.7886	Intermediate Similarity	NPC168616
0.7877	Intermediate Similarity	NPC292788
0.7877	Intermediate Similarity	NPC272485
0.7874	Intermediate Similarity	NPC54928
0.7865	Intermediate Similarity	NPC8070
0.7861	Intermediate Similarity	NPC186507
0.7853	Intermediate Similarity	NPC474096
0.7853	Intermediate Similarity	NPC108767
0.7849	Intermediate Similarity	NPC473732
0.7849	Intermediate Similarity	NPC474663
0.7849	Intermediate Similarity	NPC198615
0.7845	Intermediate Similarity	NPC474857
0.7833	Intermediate Similarity	NPC26568
0.7819	Intermediate Similarity	NPC470100
0.7816	Intermediate Similarity	NPC34725
0.7816	Intermediate Similarity	NPC276059
0.7816	Intermediate Similarity	NPC122623
0.7816	Intermediate Similarity	NPC241774
0.7811	Intermediate Similarity	NPC165512
0.7809	Intermediate Similarity	NPC474350
0.7807	Intermediate Similarity	NPC474499
0.7803	Intermediate Similarity	NPC475116
0.7803	Intermediate Similarity	NPC289968
0.7797	Intermediate Similarity	NPC298401
0.779	Intermediate Similarity	NPC20543
0.779	Intermediate Similarity	NPC239440
0.779	Intermediate Similarity	NPC1827
0.779	Intermediate Similarity	NPC10576
0.779	Intermediate Similarity	NPC107283
0.779	Intermediate Similarity	NPC17219
0.779	Intermediate Similarity	NPC277865
0.779	Intermediate Similarity	NPC246716
0.7771	Intermediate Similarity	NPC474983
0.7771	Intermediate Similarity	NPC257277
0.7765	Intermediate Similarity	NPC58653
0.7765	Intermediate Similarity	NPC106461
0.7765	Intermediate Similarity	NPC283002
0.7765	Intermediate Similarity	NPC302408
0.7765	Intermediate Similarity	NPC40818
0.7765	Intermediate Similarity	NPC215932
0.7765	Intermediate Similarity	NPC14958
0.7765	Intermediate Similarity	NPC173352
0.7765	Intermediate Similarity	NPC110639
0.776	Intermediate Similarity	NPC477568
0.776	Intermediate Similarity	NPC264922
0.7753	Intermediate Similarity	NPC473696
0.7746	Intermediate Similarity	NPC474170
0.7746	Intermediate Similarity	NPC472535
0.7746	Intermediate Similarity	NPC474388
0.7738	Intermediate Similarity	NPC29536
0.7737	Intermediate Similarity	NPC221185
0.7725	Intermediate Similarity	NPC207418
0.7722	Intermediate Similarity	NPC29160
0.7722	Intermediate Similarity	NPC28669
0.7722	Intermediate Similarity	NPC474061
0.7719	Intermediate Similarity	NPC85233
0.7719	Intermediate Similarity	NPC205522
0.7714	Intermediate Similarity	NPC20541
0.7709	Intermediate Similarity	NPC470081
0.7709	Intermediate Similarity	NPC234004
0.7705	Intermediate Similarity	NPC181523
0.7701	Intermediate Similarity	NPC99937
0.7697	Intermediate Similarity	NPC472405
0.7696	Intermediate Similarity	NPC247104
0.7692	Intermediate Similarity	NPC9966
0.7692	Intermediate Similarity	NPC70853
0.7688	Intermediate Similarity	NPC177839
0.768	Intermediate Similarity	NPC234331
0.7676	Intermediate Similarity	NPC472606
0.7674	Intermediate Similarity	NPC476058
0.7674	Intermediate Similarity	NPC183236
0.7674	Intermediate Similarity	NPC63256
0.7674	Intermediate Similarity	NPC10304
0.767	Intermediate Similarity	NPC472456
0.7663	Intermediate Similarity	NPC139350
0.7663	Intermediate Similarity	NPC289147
0.7661	Intermediate Similarity	NPC231013
0.7656	Intermediate Similarity	NPC48822
0.7654	Intermediate Similarity	NPC8300
0.7647	Intermediate Similarity	NPC23955
0.7647	Intermediate Similarity	NPC95123
0.7647	Intermediate Similarity	NPC27106
0.7647	Intermediate Similarity	NPC113089
0.7647	Intermediate Similarity	NPC66404
0.7644	Intermediate Similarity	NPC204350
0.7637	Intermediate Similarity	NPC163130
0.7637	Intermediate Similarity	NPC49487
0.7637	Intermediate Similarity	NPC99613
0.7637	Intermediate Similarity	NPC165979
0.7633	Intermediate Similarity	NPC105648
0.763	Intermediate Similarity	NPC181250
0.763	Intermediate Similarity	NPC474648
0.763	Intermediate Similarity	NPC69752
0.763	Intermediate Similarity	NPC328119
0.763	Intermediate Similarity	NPC238366
0.7627	Intermediate Similarity	NPC300727
0.7627	Intermediate Similarity	NPC472404
0.7627	Intermediate Similarity	NPC165977
0.7627	Intermediate Similarity	NPC241904
0.7627	Intermediate Similarity	NPC217677
0.7624	Intermediate Similarity	NPC472452
0.7614	Intermediate Similarity	NPC471746
0.7602	Intermediate Similarity	NPC136278
0.7602	Intermediate Similarity	NPC134621
0.76	Intermediate Similarity	NPC292460
0.7596	Intermediate Similarity	NPC109827
0.7596	Intermediate Similarity	NPC124470
0.7594	Intermediate Similarity	NPC151292
0.7586	Intermediate Similarity	NPC201547
0.7586	Intermediate Similarity	NPC259058
0.7586	Intermediate Similarity	NPC306821
0.7584	Intermediate Similarity	NPC476242
0.7574	Intermediate Similarity	NPC220106
0.7574	Intermediate Similarity	NPC58229
0.7571	Intermediate Similarity	NPC274730
0.7571	Intermediate Similarity	NPC301897
0.7571	Intermediate Similarity	NPC227062
0.7569	Intermediate Similarity	NPC130920
0.7569	Intermediate Similarity	NPC68850
0.7569	Intermediate Similarity	NPC85057
0.7566	Intermediate Similarity	NPC191606
0.7558	Intermediate Similarity	NPC237208
0.7558	Intermediate Similarity	NPC310259
0.7558	Intermediate Similarity	NPC473927
0.7557	Intermediate Similarity	NPC473664
0.7554	Intermediate Similarity	NPC158226
0.7544	Intermediate Similarity	NPC182842
0.7544	Intermediate Similarity	NPC293201
0.7543	Intermediate Similarity	NPC308451
0.7543	Intermediate Similarity	NPC208043
0.7543	Intermediate Similarity	NPC226973
0.7543	Intermediate Similarity	NPC117579
0.7542	Intermediate Similarity	NPC475886
0.7542	Intermediate Similarity	NPC228785
0.7542	Intermediate Similarity	NPC474287
0.7542	Intermediate Similarity	NPC56085
0.7542	Intermediate Similarity	NPC14353
0.754	Intermediate Similarity	NPC470091
0.754	Intermediate Similarity	NPC240887
0.754	Intermediate Similarity	NPC329161
0.754	Intermediate Similarity	NPC113446
0.753	Intermediate Similarity	NPC143649
0.7529	Intermediate Similarity	NPC214919
0.7529	Intermediate Similarity	NPC124467
0.7528	Intermediate Similarity	NPC108456
0.7514	Intermediate Similarity	NPC62536
0.7514	Intermediate Similarity	NPC299923
0.7514	Intermediate Similarity	NPC33265
0.7514	Intermediate Similarity	NPC117463
0.7514	Intermediate Similarity	NPC12200
0.7514	Intermediate Similarity	NPC470511
0.75	Intermediate Similarity	NPC134677
0.75	Intermediate Similarity	NPC474186
0.75	Intermediate Similarity	NPC241498
0.75	Intermediate Similarity	NPC166201
0.75	Intermediate Similarity	NPC474187
0.75	Intermediate Similarity	NPC278052

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 NPC108278 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	478
0.1-0.2	1230
0.2-0.3	2436
0.3-0.4	2617
0.4-0.5	1505
0.5-0.6	682
0.6-0.7	179
0.7-0.8	23
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
0.7966	Intermediate Similarity	NPD2403	Approved
0.787	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD3817	Phase 2
0.7458	Intermediate Similarity	NPD2801	Approved
0.7351	Intermediate Similarity	NPD5844	Phase 1
0.7348	Intermediate Similarity	NPD5494	Approved
0.7303	Intermediate Similarity	NPD1934	Approved
0.7273	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD957	Approved
0.7268	Intermediate Similarity	NPD6232	Discontinued
0.7263	Intermediate Similarity	NPD1465	Phase 2
0.7251	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD919	Approved
0.7167	Intermediate Similarity	NPD7819	Suspended
0.7151	Intermediate Similarity	NPD7473	Discontinued
0.7151	Intermediate Similarity	NPD958	Approved
0.7143	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7088	Intermediate Similarity	NPD3882	Suspended
0.7072	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1512	Approved
0.7027	Intermediate Similarity	NPD1247	Approved
0.7016	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6599	Discontinued
0.6995	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3748	Approved
0.6952	Remote Similarity	NPD3926	Phase 2
0.6936	Remote Similarity	NPD2796	Approved
0.6927	Remote Similarity	NPD920	Approved
0.6927	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6166	Phase 2
0.6915	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1243	Approved
0.6901	Remote Similarity	NPD1933	Approved
0.6901	Remote Similarity	NPD447	Suspended
0.6895	Remote Similarity	NPD7054	Approved
0.6885	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7472	Approved
0.6859	Remote Similarity	NPD7074	Phase 3
0.6848	Remote Similarity	NPD5402	Approved
0.6842	Remote Similarity	NPD3818	Discontinued
0.6831	Remote Similarity	NPD6801	Discontinued
0.6816	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2533	Approved
0.6816	Remote Similarity	NPD2532	Approved
0.6816	Remote Similarity	NPD2534	Approved
0.6813	Remote Similarity	NPD4972	Discontinued
0.6802	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD1184	Approved
0.68	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2353	Approved
0.678	Remote Similarity	NPD3750	Approved
0.6774	Remote Similarity	NPD3749	Approved
0.6774	Remote Similarity	NPD7075	Discontinued
0.6755	Remote Similarity	NPD6959	Discontinued
0.6755	Remote Similarity	NPD7199	Phase 2
0.6753	Remote Similarity	NPD7808	Phase 3
0.6743	Remote Similarity	NPD2935	Discontinued
0.6742	Remote Similarity	NPD3887	Approved
0.6736	Remote Similarity	NPD6797	Phase 2
0.6725	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6832	Phase 2
0.6705	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7251	Discontinued
0.6685	Remote Similarity	NPD7411	Suspended
0.6684	Remote Similarity	NPD5242	Approved
0.6684	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6649	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2354	Approved
0.6648	Remote Similarity	NPD1551	Phase 2
0.6647	Remote Similarity	NPD1240	Approved
0.6647	Remote Similarity	NPD454	Approved
0.663	Remote Similarity	NPD5401	Approved
0.6609	Remote Similarity	NPD230	Phase 1
0.6596	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1510	Phase 2
0.6591	Remote Similarity	NPD2799	Discontinued
0.6584	Remote Similarity	NPD4363	Phase 3
0.6584	Remote Similarity	NPD4360	Phase 2
0.6578	Remote Similarity	NPD5353	Approved
0.6571	Remote Similarity	NPD1607	Approved
0.6559	Remote Similarity	NPD37	Approved
0.6557	Remote Similarity	NPD5403	Approved
0.655	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4965	Approved
0.6543	Remote Similarity	NPD4966	Approved
0.6543	Remote Similarity	NPD7768	Phase 2
0.6543	Remote Similarity	NPD4967	Phase 2
0.6541	Remote Similarity	NPD4380	Phase 2
0.6538	Remote Similarity	NPD1578	Phase 2
0.6536	Remote Similarity	NPD2800	Approved
0.6517	Remote Similarity	NPD2346	Discontinued
0.6505	Remote Similarity	NPD6386	Approved
0.6505	Remote Similarity	NPD6385	Approved
0.65	Remote Similarity	NPD4628	Phase 3
0.6489	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6234	Discontinued
0.6471	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4361	Phase 2
0.6467	Remote Similarity	NPD17	Approved
0.6448	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1296	Phase 2
0.6433	Remote Similarity	NPD1203	Approved
0.641	Remote Similarity	NPD3751	Discontinued
0.6409	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD651	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1163	Approved
0.6395	Remote Similarity	NPD1019	Discontinued
0.6378	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3787	Discontinued
0.6373	Remote Similarity	NPD5711	Approved
0.6373	Remote Similarity	NPD5710	Approved
0.6364	Remote Similarity	NPD943	Approved
0.6364	Remote Similarity	NPD6559	Discontinued
0.6354	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD9717	Approved
0.6353	Remote Similarity	NPD1608	Approved
0.6344	Remote Similarity	NPD1653	Approved
0.6341	Remote Similarity	NPD6312	Discontinued
0.6337	Remote Similarity	NPD3267	Approved
0.6337	Remote Similarity	NPD3266	Approved
0.6324	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4288	Approved
0.6316	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD4534	Discontinued
0.6294	Remote Similarity	NPD7286	Phase 2
0.6289	Remote Similarity	NPD7229	Phase 3
0.6286	Remote Similarity	NPD5006	Approved
0.6286	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5005	Approved
0.6271	Remote Similarity	NPD4307	Phase 2
0.6268	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD2654	Approved
0.6264	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2313	Discontinued
0.625	Remote Similarity	NPD411	Approved
0.625	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7228	Approved
0.6238	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5953	Discontinued
0.623	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.623	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD5958	Discontinued
0.6199	Remote Similarity	NPD1611	Approved
0.6199	Remote Similarity	NPD422	Phase 1
0.6188	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6100	Approved
0.6188	Remote Similarity	NPD6099	Approved
0.6183	Remote Similarity	NPD3146	Approved
0.6183	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.618	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.618	Remote Similarity	NPD1613	Approved
0.6172	Remote Similarity	NPD4420	Approved
0.6171	Remote Similarity	NPD3018	Phase 2
0.6169	Remote Similarity	NPD7549	Discontinued
0.6158	Remote Similarity	NPD3268	Approved
0.6158	Remote Similarity	NPD6785	Approved
0.6158	Remote Similarity	NPD6784	Approved
0.6154	Remote Similarity	NPD2344	Approved
0.6154	Remote Similarity	NPD1471	Phase 3
0.6154	Remote Similarity	NPD8127	Discontinued
0.6149	Remote Similarity	NPD2797	Approved
0.6142	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD4308	Phase 3
0.6129	Remote Similarity	NPD7783	Phase 2
0.6129	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7390	Discontinued
0.6127	Remote Similarity	NPD8434	Phase 2
0.6127	Remote Similarity	NPD4359	Approved
0.6124	Remote Similarity	NPD6233	Phase 2
0.612	Remote Similarity	NPD2808	Discontinued
0.6119	Remote Similarity	NPD7240	Approved
0.6119	Remote Similarity	NPD3303	Discontinued
0.6118	Remote Similarity	NPD9268	Approved
0.6111	Remote Similarity	NPD6651	Approved
0.6108	Remote Similarity	NPD6190	Approved
0.6105	Remote Similarity	NPD3705	Approved
0.6105	Remote Similarity	NPD1281	Approved
0.6105	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD3027	Phase 3
0.6099	Remote Similarity	NPD4476	Approved
0.6099	Remote Similarity	NPD2438	Suspended
0.6099	Remote Similarity	NPD4477	Approved
0.6096	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5536	Phase 2
0.6094	Remote Similarity	NPD1852	Discontinued
0.6092	Remote Similarity	NPD3225	Approved
0.6089	Remote Similarity	NPD2979	Phase 3
0.6077	Remote Similarity	NPD4536	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