NPASS Compound

Structure

CID8070 OpenBabel06191715332D 35 37 0 0 0 0 0 0 0 0999 V2000 -7.2626 -1.0521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0842 6.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6993 -1.8783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0842 5.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7021 -1.8036 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 -5.2682 -0.9026 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 -4.2710 -0.8279 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 -2.8399 0.1478 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 1.6479 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 -3.8371 0.0731 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 -2.5355 2.7760 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 -1.5382 2.8507 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 3.3799 2.1235 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 -4.4004 0.8993 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 -3.0988 3.6022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1044 3.7517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 3.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2459 1.6235 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 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 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 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 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 27 2 0 0 0 0 16 21 2 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 28 1 0 0 0 0 18 22 2 0 0 0 0 18 29 1 0 0 0 0 19 23 2 0 0 0 0 19 34 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 22 24 1 0 0 0 0 22 30 1 0 0 0 0 23 35 1 0 0 0 0 24 35 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.19
Volume:	487.967
LogP:	5.943
LogD:	2.841
LogS:	-3.401
# Rotatable Bonds:	11
TPSA:	150.59
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.144
Synthetic Accessibility Score:	3.205
Fsp3:	0.423
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.687
MDCK Permeability:	2.4807404770399444e-05
Pgp-inhibitor:	0.456
Pgp-substrate:	0.974
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.097

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	99.20931243896484%
Volume Distribution (VD):	0.262
Pgp-substrate:	0.7488862872123718%

ADMET: Metabolism

CYP1A2-inhibitor:	0.299
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.63
CYP2C9-substrate:	0.172
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.024

ADMET: Excretion

Clearance (CL):	1.884
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.62
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.104
Rat Oral Acute Toxicity:	0.739
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.723
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.53
Respiratory Toxicity:	0.746

Download Data

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

Natural Product: NPC8070

Natural Product ID:	NPC8070
*Common Name:**	Oxyphysodic Acid
IUPAC Name:	3,9,10-trihydroxy-6-oxo-7-(2-oxoheptyl)-1-pentylbenzo[b][1,4]benzodioxepine-2-carboxylic acid
Synonyms:
Standard InCHIKey:	BQHHNAPTXQOPBW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H30O9/c1-3-5-7-9-15(27)11-14-12-18(29)22(30)24-20(14)26(33)34-19-13-17(28)21(25(31)32)16(23(19)35-24)10-8-6-4-2/h12-13,28-30H,3-11H2,1-2H3,(H,31,32)
SMILES:	CCCCCC(=O)Cc1cc(O)c(c2c1C(=O)Oc1c(O2)c(CCCCC)c(c(c1)O)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2272212
PubChem CID:	171308
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
NPO9715	Hypericum richeri	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18984	Aster lautureanus	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
ED50	1
Others	4

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	15.0	%	PMID[469452]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	50.0	%	PMID[469452]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	0.33	g	PMID[469452]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	TIME	=	456.0	hr	PMID[469452]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	ED50	=	11.2	uM	PMID[469452]

☑ 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 NPC8070 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	411
0.1-0.2	1874
0.2-0.3	4733
0.3-0.4	10395
0.4-0.5	7318
0.5-0.6	3718
0.6-0.7	5142
0.7-0.8	6050
0.8-0.85	2195
0.85-0.9	788
0.9-0.95	64
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9871	High Similarity	NPC93739
0.9808	High Similarity	NPC284007
0.9745	High Similarity	NPC267153
0.9557	High Similarity	NPC300984
0.9554	High Similarity	NPC303565
0.9551	High Similarity	NPC238381
0.9484	High Similarity	NPC471800
0.9448	High Similarity	NPC139350
0.9423	High Similarity	NPC54928
0.9313	High Similarity	NPC474350
0.9304	High Similarity	NPC168616
0.9304	High Similarity	NPC83763
0.9299	High Similarity	NPC274730
0.9277	High Similarity	NPC113446
0.9264	High Similarity	NPC109827
0.9264	High Similarity	NPC124470
0.9264	High Similarity	NPC246716
0.9264	High Similarity	NPC239440
0.9264	High Similarity	NPC20543
0.9245	High Similarity	NPC200594
0.9241	High Similarity	NPC300727
0.9241	High Similarity	NPC241904
0.9231	High Similarity	NPC289968
0.9207	High Similarity	NPC158226
0.9202	High Similarity	NPC26568
0.9198	High Similarity	NPC20216
0.9193	High Similarity	NPC156082
0.9182	High Similarity	NPC100123
0.9182	High Similarity	NPC476242
0.9172	High Similarity	NPC89474
0.9152	High Similarity	NPC181523
0.9146	High Similarity	NPC17219
0.9146	High Similarity	NPC1827
0.9146	High Similarity	NPC10576
0.9141	High Similarity	NPC292788
0.9141	High Similarity	NPC272485
0.9136	High Similarity	NPC112981
0.913	High Similarity	NPC8300
0.9125	High Similarity	NPC228785
0.9125	High Similarity	NPC56085
0.9125	High Similarity	NPC320359
0.9125	High Similarity	NPC14353
0.9125	High Similarity	NPC200746
0.9114	High Similarity	NPC38898
0.9096	High Similarity	NPC289147
0.9085	High Similarity	NPC99613
0.9085	High Similarity	NPC163130
0.9085	High Similarity	NPC49487
0.9085	High Similarity	NPC165979
0.9074	High Similarity	NPC234004
0.9068	High Similarity	NPC278052
0.9068	High Similarity	NPC40491
0.9068	High Similarity	NPC61010
0.9057	High Similarity	NPC472456
0.9057	High Similarity	NPC142339
0.9051	High Similarity	NPC250822
0.9051	High Similarity	NPC276409
0.9051	High Similarity	NPC75279
0.9045	High Similarity	NPC202157
0.9038	High Similarity	NPC6923
0.9018	High Similarity	NPC85057
0.9018	High Similarity	NPC130920
0.9012	High Similarity	NPC25152
0.9006	High Similarity	NPC139036
0.9	High Similarity	NPC165977
0.9	High Similarity	NPC217677
0.9	High Similarity	NPC236796
0.9	High Similarity	NPC469584
0.8994	High Similarity	NPC183597
0.8994	High Similarity	NPC20541
0.8994	High Similarity	NPC146165
0.8994	High Similarity	NPC163780
0.8994	High Similarity	NPC208197
0.8994	High Similarity	NPC201136
0.8994	High Similarity	NPC128863
0.8994	High Similarity	NPC227325
0.8994	High Similarity	NPC92659
0.8994	High Similarity	NPC167815
0.8994	High Similarity	NPC4455
0.8994	High Similarity	NPC2476
0.8994	High Similarity	NPC138360
0.8994	High Similarity	NPC280339
0.8994	High Similarity	NPC50715
0.8994	High Similarity	NPC196439
0.8981	High Similarity	NPC60413
0.8981	High Similarity	NPC151473
0.8963	High Similarity	NPC29160
0.8957	High Similarity	NPC270837
0.8957	High Similarity	NPC236132
0.8957	High Similarity	NPC189473
0.8957	High Similarity	NPC236521
0.8957	High Similarity	NPC220313
0.8957	High Similarity	NPC152659
0.8957	High Similarity	NPC475985
0.8957	High Similarity	NPC23298
0.8957	High Similarity	NPC7483
0.8957	High Similarity	NPC248638
0.8957	High Similarity	NPC133065
0.8951	High Similarity	NPC258331
0.8944	High Similarity	NPC329091
0.8944	High Similarity	NPC474290
0.8938	High Similarity	NPC138243
0.8938	High Similarity	NPC68093
0.8938	High Similarity	NPC474520
0.8938	High Similarity	NPC191146
0.8931	High Similarity	NPC274327
0.8931	High Similarity	NPC69394
0.8931	High Similarity	NPC145379
0.8931	High Similarity	NPC255350
0.8931	High Similarity	NPC160951
0.8931	High Similarity	NPC176775
0.8931	High Similarity	NPC231018
0.8931	High Similarity	NPC475895
0.8931	High Similarity	NPC47781
0.8931	High Similarity	NPC183878
0.8931	High Similarity	NPC22519
0.8924	High Similarity	NPC204350
0.8924	High Similarity	NPC474663
0.8909	High Similarity	NPC234331
0.8902	High Similarity	NPC239752
0.8902	High Similarity	NPC275780
0.8902	High Similarity	NPC326520
0.8902	High Similarity	NPC39306
0.8902	High Similarity	NPC472450
0.8896	High Similarity	NPC294965
0.8889	High Similarity	NPC119224
0.8889	High Similarity	NPC474287
0.8889	High Similarity	NPC475886
0.8889	High Similarity	NPC45146
0.8889	High Similarity	NPC235018
0.8882	High Similarity	NPC472914
0.8882	High Similarity	NPC474208
0.8882	High Similarity	NPC96167
0.8882	High Similarity	NPC472913
0.8882	High Similarity	NPC474836
0.8882	High Similarity	NPC475267
0.8882	High Similarity	NPC472438
0.8882	High Similarity	NPC472910
0.8882	High Similarity	NPC222814
0.8882	High Similarity	NPC189179
0.8882	High Similarity	NPC7973
0.8882	High Similarity	NPC136674
0.8882	High Similarity	NPC262286
0.8882	High Similarity	NPC472911
0.8882	High Similarity	NPC224137
0.8882	High Similarity	NPC75215
0.8882	High Similarity	NPC36852
0.8882	High Similarity	NPC78302
0.8882	High Similarity	NPC78225
0.8882	High Similarity	NPC29841
0.8882	High Similarity	NPC227192
0.8882	High Similarity	NPC48208
0.8882	High Similarity	NPC235215
0.8882	High Similarity	NPC156057
0.8882	High Similarity	NPC245758
0.8882	High Similarity	NPC93376
0.8882	High Similarity	NPC162869
0.8875	High Similarity	NPC16082
0.8875	High Similarity	NPC472048
0.8875	High Similarity	NPC256612
0.8875	High Similarity	NPC79998
0.8875	High Similarity	NPC82592
0.8875	High Similarity	NPC20830
0.8875	High Similarity	NPC213622
0.8868	High Similarity	NPC275836
0.8868	High Similarity	NPC187498
0.8868	High Similarity	NPC57030
0.8868	High Similarity	NPC71334
0.8868	High Similarity	NPC222830
0.8868	High Similarity	NPC188203
0.8868	High Similarity	NPC275722
0.8868	High Similarity	NPC120163
0.8868	High Similarity	NPC156222
0.8868	High Similarity	NPC142540
0.8868	High Similarity	NPC241498
0.8868	High Similarity	NPC101996
0.8868	High Similarity	NPC83508
0.8868	High Similarity	NPC162313
0.8868	High Similarity	NPC100887
0.8868	High Similarity	NPC198826
0.8868	High Similarity	NPC301323
0.8868	High Similarity	NPC212678
0.8868	High Similarity	NPC180234
0.8868	High Similarity	NPC199100
0.8868	High Similarity	NPC131624
0.8868	High Similarity	NPC120537
0.8868	High Similarity	NPC239128
0.8868	High Similarity	NPC25270
0.8868	High Similarity	NPC293183
0.8868	High Similarity	NPC256283
0.8861	High Similarity	NPC61620
0.8861	High Similarity	NPC29056
0.8855	High Similarity	NPC247136
0.8855	High Similarity	NPC280493
0.8848	High Similarity	NPC37870
0.8848	High Similarity	NPC39091
0.8848	High Similarity	NPC170245
0.8848	High Similarity	NPC472452
0.8848	High Similarity	NPC472449
0.8841	High Similarity	NPC146134

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 NPC8070 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	361
0.1-0.2	1035
0.2-0.3	2016
0.3-0.4	2633
0.4-0.5	1670
0.5-0.6	899
0.6-0.7	372
0.7-0.8	133
0.8-0.85	23
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8931	High Similarity	NPD2801	Approved
0.8696	High Similarity	NPD1465	Phase 2
0.8634	High Similarity	NPD1934	Approved
0.8554	High Similarity	NPD6232	Discontinued
0.8528	High Similarity	NPD3817	Phase 2
0.8512	High Similarity	NPD7473	Discontinued
0.8481	Intermediate Similarity	NPD1511	Approved
0.8476	Intermediate Similarity	NPD3882	Suspended
0.8476	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD1512	Approved
0.8353	Intermediate Similarity	NPD3818	Discontinued
0.8343	Intermediate Similarity	NPD6166	Phase 2
0.8343	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD5844	Phase 1
0.8256	Intermediate Similarity	NPD7074	Phase 3
0.8242	Intermediate Similarity	NPD7819	Suspended
0.8198	Intermediate Similarity	NPD7054	Approved
0.8165	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD7472	Approved
0.811	Intermediate Similarity	NPD3226	Approved
0.8107	Intermediate Similarity	NPD5494	Approved
0.8103	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7075	Discontinued
0.8025	Intermediate Similarity	NPD6799	Approved
0.8012	Intermediate Similarity	NPD7411	Suspended
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7988	Intermediate Similarity	NPD3749	Approved
0.7976	Intermediate Similarity	NPD5402	Approved
0.7975	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7975	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7251	Discontinued
0.7952	Intermediate Similarity	NPD6599	Discontinued
0.795	Intermediate Similarity	NPD3750	Approved
0.7944	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD7808	Phase 3
0.7898	Intermediate Similarity	NPD447	Suspended
0.7882	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6801	Discontinued
0.7849	Intermediate Similarity	NPD1247	Approved
0.7849	Intermediate Similarity	NPD6959	Discontinued
0.7844	Intermediate Similarity	NPD4380	Phase 2
0.7836	Intermediate Similarity	NPD6234	Discontinued
0.7834	Intermediate Similarity	NPD943	Approved
0.7816	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2935	Discontinued
0.7785	Intermediate Similarity	NPD230	Phase 1
0.7764	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3926	Phase 2
0.7758	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2799	Discontinued
0.775	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7199	Phase 2
0.7733	Intermediate Similarity	NPD919	Approved
0.7722	Intermediate Similarity	NPD1240	Approved
0.7716	Intermediate Similarity	NPD1549	Phase 2
0.7669	Intermediate Similarity	NPD2800	Approved
0.7665	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD37	Approved
0.764	Intermediate Similarity	NPD3748	Approved
0.764	Intermediate Similarity	NPD1510	Phase 2
0.7625	Intermediate Similarity	NPD1607	Approved
0.7616	Intermediate Similarity	NPD4967	Phase 2
0.7616	Intermediate Similarity	NPD4965	Approved
0.7616	Intermediate Similarity	NPD4966	Approved
0.7593	Intermediate Similarity	NPD2796	Approved
0.7584	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1243	Approved
0.756	Intermediate Similarity	NPD5403	Approved
0.7556	Intermediate Similarity	NPD6559	Discontinued
0.7546	Intermediate Similarity	NPD2346	Discontinued
0.7528	Intermediate Similarity	NPD7228	Approved
0.7516	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1653	Approved
0.7515	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7484	Intermediate Similarity	NPD3268	Approved
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD920	Approved
0.744	Intermediate Similarity	NPD5401	Approved
0.7423	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5953	Discontinued
0.7401	Intermediate Similarity	NPD5711	Approved
0.7401	Intermediate Similarity	NPD5710	Approved
0.7389	Intermediate Similarity	NPD1203	Approved
0.7381	Intermediate Similarity	NPD7390	Discontinued
0.7381	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6100	Approved
0.7378	Intermediate Similarity	NPD6099	Approved
0.7365	Intermediate Similarity	NPD6190	Approved
0.7351	Intermediate Similarity	NPD8434	Phase 2
0.7337	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2344	Approved
0.7333	Intermediate Similarity	NPD3751	Discontinued
0.7312	Intermediate Similarity	NPD3027	Phase 3
0.7308	Intermediate Similarity	NPD9269	Phase 2
0.7305	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3787	Discontinued
0.7293	Intermediate Similarity	NPD7286	Phase 2
0.7284	Intermediate Similarity	NPD1613	Approved
0.7284	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8312	Approved
0.7283	Intermediate Similarity	NPD8313	Approved
0.7267	Intermediate Similarity	NPD2313	Discontinued
0.7263	Intermediate Similarity	NPD5242	Approved
0.725	Intermediate Similarity	NPD6832	Phase 2
0.7239	Intermediate Similarity	NPD1933	Approved
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD9717	Approved
0.7197	Intermediate Similarity	NPD1608	Approved
0.7195	Intermediate Similarity	NPD6651	Approved
0.7193	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7783	Phase 2
0.7179	Intermediate Similarity	NPD7435	Discontinued
0.7174	Intermediate Similarity	NPD7685	Pre-registration
0.7172	Intermediate Similarity	NPD8151	Discontinued
0.717	Intermediate Similarity	NPD2797	Approved
0.717	Intermediate Similarity	NPD3267	Approved
0.717	Intermediate Similarity	NPD3266	Approved
0.7166	Intermediate Similarity	NPD8150	Discontinued
0.716	Intermediate Similarity	NPD2309	Approved
0.7135	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD422	Phase 1
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2403	Approved
0.7113	Intermediate Similarity	NPD6781	Approved
0.7113	Intermediate Similarity	NPD6777	Approved
0.7113	Intermediate Similarity	NPD6778	Approved
0.7113	Intermediate Similarity	NPD6782	Approved
0.7113	Intermediate Similarity	NPD6780	Approved
0.7113	Intermediate Similarity	NPD6779	Approved
0.7113	Intermediate Similarity	NPD6776	Approved
0.7111	Intermediate Similarity	NPD7229	Phase 3
0.709	Intermediate Similarity	NPD4287	Approved
0.7081	Intermediate Similarity	NPD9494	Approved
0.7081	Intermediate Similarity	NPD7240	Approved
0.7073	Intermediate Similarity	NPD4060	Phase 1
0.7062	Intermediate Similarity	NPD5353	Approved
0.7062	Intermediate Similarity	NPD4288	Approved
0.7055	Intermediate Similarity	NPD3764	Approved
0.7055	Intermediate Similarity	NPD411	Approved
0.7051	Intermediate Similarity	NPD9268	Approved
0.7044	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1471	Phase 3
0.7006	Intermediate Similarity	NPD17	Approved
0.7006	Intermediate Similarity	NPD4308	Phase 3
0.7	Intermediate Similarity	NPD3225	Approved
0.6989	Remote Similarity	NPD6385	Approved
0.6989	Remote Similarity	NPD6386	Approved
0.6968	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7874	Approved
0.6964	Remote Similarity	NPD5408	Approved
0.6964	Remote Similarity	NPD5404	Approved
0.6964	Remote Similarity	NPD5405	Approved
0.6964	Remote Similarity	NPD5406	Approved
0.6961	Remote Similarity	NPD8127	Discontinued
0.6959	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7549	Discontinued
0.6952	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1296	Phase 2
0.6936	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6355	Discontinued
0.6919	Remote Similarity	NPD7696	Phase 3
0.6919	Remote Similarity	NPD7698	Approved
0.6919	Remote Similarity	NPD7697	Approved
0.6914	Remote Similarity	NPD2798	Approved
0.6909	Remote Similarity	NPD6233	Phase 2
0.6905	Remote Similarity	NPD7033	Discontinued
0.689	Remote Similarity	NPD4625	Phase 3
0.6884	Remote Similarity	NPD7870	Phase 2
0.6884	Remote Similarity	NPD7871	Phase 2
0.6875	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1481	Phase 2
0.6869	Remote Similarity	NPD6823	Phase 2
0.6866	Remote Similarity	NPD7701	Phase 2
0.6864	Remote Similarity	NPD4477	Approved
0.6864	Remote Similarity	NPD4476	Approved
0.686	Remote Similarity	NPD2354	Approved
0.6856	Remote Similarity	NPD6534	Approved
0.6856	Remote Similarity	NPD6535	Approved
0.6852	Remote Similarity	NPD1470	Approved
0.6848	Remote Similarity	NPD6798	Discontinued

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