NPASS Compound

Structure

NPC142614 OpenBabel07101719402D 40 44 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 35 1 0 0 0 0 3 36 1 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 22 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 20 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 37 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 16 17 2 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 23 2 0 0 0 0 18 34 1 0 0 0 0 19 23 1 0 0 0 0 19 35 1 0 0 0 0 20 26 2 0 0 0 0 20 36 1 0 0 0 0 21 12 1 6 0 0 0 21 24 1 0 0 0 0 21 38 1 0 0 0 0 22 31 2 0 0 0 0 22 39 1 0 0 0 0 23 32 1 0 0 0 0 24 15 1 1 0 0 0 24 40 1 0 0 0 0 25 27 2 0 0 0 0 25 39 1 0 0 0 0 26 27 1 0 0 0 0 26 40 1 0 0 0 0 27 38 1 0 0 0 0 28 33 2 0 0 0 0 28 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	552.13
Volume:	523.907
LogP:	3.012
LogD:	2.407
LogS:	-4.339
# Rotatable Bonds:	8
TPSA:	163.35
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.173
Synthetic Accessibility Score:	3.709
Fsp3:	0.214
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.174
MDCK Permeability:	3.908563667209819e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.098
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.118

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	86.35900115966797%
Volume Distribution (VD):	0.508
Pgp-substrate:	26.402029037475586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.123
CYP1A2-substrate:	0.898
CYP2C19-inhibitor:	0.306
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.767
CYP2D6-inhibitor:	0.133
CYP2D6-substrate:	0.354
CYP3A4-inhibitor:	0.346
CYP3A4-substrate:	0.499

ADMET: Excretion

Clearance (CL):	9.424
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.268
Human Hepatotoxicity (H-HT):	0.518
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.362
Maximum Recommended Daily Dose:	0.492
Skin Sensitization:	0.884
Carcinogencity:	0.578
Eye Corrosion:	0.003
Eye Irritation:	0.823
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC142614

Natural Product ID:	NPC142614
*Common Name:**	Repenin D
IUPAC Name:	[(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-5-methoxy-9-oxo-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-2-yl]methyl 3,4-dihydroxybenzoate
Synonyms:	Repenin D
Standard InCHIKey:	WQIZCXIRVAHPRD-ZJSXRUAMSA-N
Standard InCHI:	InChI=1S/C28H24O12/c1-34-18-10-15(11-19(35-2)23(18)32)24-21(12-37-28(33)14-4-6-16(29)17(30)8-14)38-27-25-13(5-7-22(31)39-25)9-20(36-3)26(27)40-24/h4-11,21,24,29-30,32H,12H2,1-3H3/t21-,24-/m1/s1
SMILES:	COc1cc(cc(c1O)OC)[C@@H]1[C@@H](COC(=O)c2ccc(c(c2)O)O)Oc2c3c(ccc(=O)o3)cc(c2O1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502250
PubChem CID:	44583461
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0002545] Coumarinolignans

*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
NPO32501	Duranta erecta	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19464173]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	510000.0	nM	PMID[540356]

☑ 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 NPC142614 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	427
0.1-0.2	1892
0.2-0.3	5032
0.3-0.4	10329
0.4-0.5	7323
0.5-0.6	4018
0.6-0.7	5410
0.7-0.8	4903
0.8-0.85	1914
0.85-0.9	1247
0.9-0.95	184
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC53889
0.9551	High Similarity	NPC87317
0.949	High Similarity	NPC24164
0.9487	High Similarity	NPC160512
0.9487	High Similarity	NPC289322
0.9487	High Similarity	NPC68324
0.9487	High Similarity	NPC114179
0.9487	High Similarity	NPC38779
0.9487	High Similarity	NPC156818
0.9423	High Similarity	NPC300845
0.9423	High Similarity	NPC291948
0.9423	High Similarity	NPC318432
0.9423	High Similarity	NPC250436
0.9423	High Similarity	NPC104983
0.9423	High Similarity	NPC88803
0.9379	High Similarity	NPC243877
0.9379	High Similarity	NPC473818
0.9321	High Similarity	NPC280493
0.929	High Similarity	NPC163598
0.929	High Similarity	NPC120774
0.929	High Similarity	NPC264875
0.9273	High Similarity	NPC472992
0.9273	High Similarity	NPC472991
0.9268	High Similarity	NPC163165
0.9259	High Similarity	NPC295082
0.9259	High Similarity	NPC14662
0.925	High Similarity	NPC476371
0.925	High Similarity	NPC476372
0.9231	High Similarity	NPC474656
0.9207	High Similarity	NPC81332
0.9207	High Similarity	NPC262580
0.9207	High Similarity	NPC212038
0.9207	High Similarity	NPC289396
0.9207	High Similarity	NPC271848
0.9193	High Similarity	NPC67959
0.9187	High Similarity	NPC113163
0.9187	High Similarity	NPC66618
0.9187	High Similarity	NPC305987
0.9187	High Similarity	NPC84324
0.9187	High Similarity	NPC288131
0.9187	High Similarity	NPC165970
0.9167	High Similarity	NPC36138
0.9167	High Similarity	NPC75695
0.9152	High Similarity	NPC472993
0.9146	High Similarity	NPC476365
0.913	High Similarity	NPC285108
0.913	High Similarity	NPC4013
0.913	High Similarity	NPC90905
0.913	High Similarity	NPC33298
0.9125	High Similarity	NPC101731
0.9125	High Similarity	NPC476373
0.9112	High Similarity	NPC470416
0.9102	High Similarity	NPC472387
0.9102	High Similarity	NPC476618
0.9102	High Similarity	NPC476619
0.9102	High Similarity	NPC476622
0.9102	High Similarity	NPC476621
0.9102	High Similarity	NPC476620
0.9102	High Similarity	NPC476623
0.9097	High Similarity	NPC176903
0.9097	High Similarity	NPC30688
0.9097	High Similarity	NPC107636
0.9096	High Similarity	NPC169645
0.9096	High Similarity	NPC84482
0.9091	High Similarity	NPC211594
0.9091	High Similarity	NPC254540
0.9091	High Similarity	NPC102851
0.9091	High Similarity	NPC172807
0.9091	High Similarity	NPC5786
0.9085	High Similarity	NPC476279
0.9074	High Similarity	NPC272064
0.9068	High Similarity	NPC472859
0.9068	High Similarity	NPC25389
0.9068	High Similarity	NPC311803
0.9062	High Similarity	NPC284127
0.9062	High Similarity	NPC172202
0.9062	High Similarity	NPC476410
0.9057	High Similarity	NPC472916
0.9038	High Similarity	NPC473091
0.9038	High Similarity	NPC21184
0.9038	High Similarity	NPC294522
0.9038	High Similarity	NPC120426
0.9038	High Similarity	NPC205727
0.9036	High Similarity	NPC172033
0.9036	High Similarity	NPC88560
0.9036	High Similarity	NPC175230
0.9032	High Similarity	NPC139839
0.903	High Similarity	NPC149011
0.903	High Similarity	NPC204937
0.9018	High Similarity	NPC471788
0.9012	High Similarity	NPC219927
0.9006	High Similarity	NPC166277
0.9006	High Similarity	NPC203020
0.9006	High Similarity	NPC289346
0.9006	High Similarity	NPC239966
0.9006	High Similarity	NPC119125
0.9006	High Similarity	NPC24627
0.9	High Similarity	NPC183851
0.9	High Similarity	NPC470402
0.9	High Similarity	NPC210084
0.9	High Similarity	NPC63454
0.9	High Similarity	NPC48208
0.9	High Similarity	NPC156057
0.9	High Similarity	NPC474208
0.9	High Similarity	NPC474836
0.9	High Similarity	NPC99597
0.9	High Similarity	NPC162869
0.9	High Similarity	NPC475267
0.8994	High Similarity	NPC183597
0.8994	High Similarity	NPC145425
0.8994	High Similarity	NPC163780
0.8994	High Similarity	NPC208197
0.8994	High Similarity	NPC227325
0.8994	High Similarity	NPC201136
0.8994	High Similarity	NPC196439
0.8994	High Similarity	NPC128863
0.8994	High Similarity	NPC256612
0.8994	High Similarity	NPC213622
0.8994	High Similarity	NPC222185
0.8994	High Similarity	NPC92659
0.8994	High Similarity	NPC167815
0.8994	High Similarity	NPC20830
0.8994	High Similarity	NPC4455
0.8994	High Similarity	NPC2476
0.8994	High Similarity	NPC146165
0.8994	High Similarity	NPC138360
0.8994	High Similarity	NPC280339
0.8994	High Similarity	NPC50715
0.8994	High Similarity	NPC2928
0.8988	High Similarity	NPC217520
0.8988	High Similarity	NPC139571
0.8988	High Similarity	NPC35167
0.8987	High Similarity	NPC289968
0.8982	High Similarity	NPC477848
0.8976	High Similarity	NPC205076
0.8976	High Similarity	NPC307518
0.8976	High Similarity	NPC48773
0.8976	High Similarity	NPC476370
0.8974	High Similarity	NPC476394
0.8974	High Similarity	NPC98809
0.897	High Similarity	NPC658
0.897	High Similarity	NPC197708
0.897	High Similarity	NPC198125
0.897	High Similarity	NPC475942
0.897	High Similarity	NPC95421
0.897	High Similarity	NPC45638
0.897	High Similarity	NPC58053
0.897	High Similarity	NPC105025
0.897	High Similarity	NPC93337
0.897	High Similarity	NPC226294
0.897	High Similarity	NPC469931
0.897	High Similarity	NPC201292
0.897	High Similarity	NPC186807
0.8963	High Similarity	NPC13481
0.8963	High Similarity	NPC471823
0.8963	High Similarity	NPC207575
0.8957	High Similarity	NPC121290
0.8951	High Similarity	NPC196179
0.8951	High Similarity	NPC124747
0.8951	High Similarity	NPC109061
0.8951	High Similarity	NPC34089
0.8951	High Similarity	NPC158188
0.8951	High Similarity	NPC155754
0.8944	High Similarity	NPC154304
0.8944	High Similarity	NPC289811
0.8944	High Similarity	NPC74319
0.8944	High Similarity	NPC40702
0.8944	High Similarity	NPC267627
0.8944	High Similarity	NPC190487
0.8944	High Similarity	NPC37502
0.8944	High Similarity	NPC287872
0.8944	High Similarity	NPC160780
0.8938	High Similarity	NPC235165
0.8938	High Similarity	NPC255106
0.8935	High Similarity	NPC471030
0.8931	High Similarity	NPC276409
0.8931	High Similarity	NPC472915
0.8931	High Similarity	NPC274327
0.8931	High Similarity	NPC145379
0.8931	High Similarity	NPC255350
0.8931	High Similarity	NPC75279
0.8931	High Similarity	NPC160951
0.8931	High Similarity	NPC176775
0.8931	High Similarity	NPC469888
0.8931	High Similarity	NPC250822
0.8931	High Similarity	NPC231018
0.8931	High Similarity	NPC47781
0.8931	High Similarity	NPC183878
0.8931	High Similarity	NPC69394
0.8931	High Similarity	NPC22519
0.8929	High Similarity	NPC67629
0.8929	High Similarity	NPC79736
0.8929	High Similarity	NPC297574
0.8929	High Similarity	NPC211532
0.8929	High Similarity	NPC472385
0.8929	High Similarity	NPC61904
0.8929	High Similarity	NPC198324
0.8929	High Similarity	NPC233994
0.8929	High Similarity	NPC144097
0.8922	High Similarity	NPC98583

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 NPC142614 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	988
0.2-0.3	2070
0.3-0.4	2610
0.4-0.5	1729
0.5-0.6	900
0.6-0.7	308
0.7-0.8	109
0.8-0.85	28
0.85-0.9	18
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9423	High Similarity	NPD4868	Clinical (unspecified phase)
0.897	High Similarity	NPD5844	Phase 1
0.8931	High Similarity	NPD2801	Approved
0.8902	High Similarity	NPD6168	Clinical (unspecified phase)
0.8902	High Similarity	NPD6167	Clinical (unspecified phase)
0.8902	High Similarity	NPD6166	Phase 2
0.8869	High Similarity	NPD4338	Clinical (unspecified phase)
0.8862	High Similarity	NPD7993	Clinical (unspecified phase)
0.875	High Similarity	NPD1934	Approved
0.8743	High Similarity	NPD7054	Approved
0.8696	High Similarity	NPD1465	Phase 2
0.869	High Similarity	NPD7472	Approved
0.8642	High Similarity	NPD3817	Phase 2
0.858	High Similarity	NPD7074	Phase 3
0.858	High Similarity	NPD2393	Clinical (unspecified phase)
0.8571	High Similarity	NPD3818	Discontinued
0.8529	High Similarity	NPD6797	Phase 2
0.848	Intermediate Similarity	NPD7251	Discontinued
0.8476	Intermediate Similarity	NPD3882	Suspended
0.843	Intermediate Similarity	NPD7808	Phase 3
0.8415	Intermediate Similarity	NPD5402	Approved
0.8385	Intermediate Similarity	NPD1653	Approved
0.8365	Intermediate Similarity	NPD1511	Approved
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD5494	Approved
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD4380	Phase 2
0.8261	Intermediate Similarity	NPD1512	Approved
0.8232	Intermediate Similarity	NPD7411	Suspended
0.8187	Intermediate Similarity	NPD7473	Discontinued
0.8146	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD230	Phase 1
0.8125	Intermediate Similarity	NPD6190	Approved
0.8098	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6801	Discontinued
0.8025	Intermediate Similarity	NPD6799	Approved
0.8024	Intermediate Similarity	NPD7819	Suspended
0.8023	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5403	Approved
0.7978	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7685	Pre-registration
0.7953	Intermediate Similarity	NPD7199	Phase 2
0.7953	Intermediate Similarity	NPD6959	Discontinued
0.795	Intermediate Similarity	NPD3750	Approved
0.7941	Intermediate Similarity	NPD6234	Discontinued
0.7937	Intermediate Similarity	NPD1549	Phase 2
0.7931	Intermediate Similarity	NPD7228	Approved
0.7888	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD5401	Approved
0.7861	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6559	Discontinued
0.784	Intermediate Similarity	NPD4628	Phase 3
0.7834	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1613	Approved
0.7824	Intermediate Similarity	NPD7768	Phase 2
0.7821	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2796	Approved
0.7809	Intermediate Similarity	NPD7549	Discontinued
0.7805	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD447	Suspended
0.776	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD37	Approved
0.775	Intermediate Similarity	NPD1510	Phase 2
0.7738	Intermediate Similarity	NPD6599	Discontinued
0.7733	Intermediate Similarity	NPD919	Approved
0.7727	Intermediate Similarity	NPD3751	Discontinued
0.7719	Intermediate Similarity	NPD4966	Approved
0.7719	Intermediate Similarity	NPD4967	Phase 2
0.7719	Intermediate Similarity	NPD4965	Approved
0.7716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2935	Discontinued
0.7692	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6233	Phase 2
0.7651	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD1247	Approved
0.7643	Intermediate Similarity	NPD3027	Phase 3
0.764	Intermediate Similarity	NPD3748	Approved
0.7628	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3787	Discontinued
0.7593	Intermediate Similarity	NPD1551	Phase 2
0.7569	Intermediate Similarity	NPD8313	Approved
0.7569	Intermediate Similarity	NPD8312	Approved
0.7558	Intermediate Similarity	NPD5353	Approved
0.7557	Intermediate Similarity	NPD3926	Phase 2
0.7546	Intermediate Similarity	NPD7266	Discontinued
0.7516	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7484	Intermediate Similarity	NPD6798	Discontinued
0.7471	Intermediate Similarity	NPD3226	Approved
0.7471	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.7459	Intermediate Similarity	NPD7038	Approved
0.7459	Intermediate Similarity	NPD7240	Approved
0.7459	Intermediate Similarity	NPD7039	Approved
0.7458	Intermediate Similarity	NPD5242	Approved
0.7456	Intermediate Similarity	NPD920	Approved
0.7455	Intermediate Similarity	NPD1652	Phase 2
0.7453	Intermediate Similarity	NPD1933	Approved
0.7449	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7783	Phase 2
0.7443	Intermediate Similarity	NPD8127	Discontinued
0.744	Intermediate Similarity	NPD2534	Approved
0.744	Intermediate Similarity	NPD2532	Approved
0.744	Intermediate Similarity	NPD2533	Approved
0.7419	Intermediate Similarity	NPD9269	Phase 2
0.741	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1607	Approved
0.7384	Intermediate Similarity	NPD6385	Approved
0.7384	Intermediate Similarity	NPD6386	Approved
0.7375	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7435	Discontinued
0.7358	Intermediate Similarity	NPD6832	Phase 2
0.7355	Intermediate Similarity	NPD422	Phase 1
0.7351	Intermediate Similarity	NPD8150	Discontinued
0.7347	Intermediate Similarity	NPD8151	Discontinued
0.7346	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5124	Phase 1
0.7337	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3225	Approved
0.7317	Intermediate Similarity	NPD4308	Phase 3
0.7308	Intermediate Similarity	NPD5953	Discontinued
0.7303	Intermediate Similarity	NPD7229	Phase 3
0.7292	Intermediate Similarity	NPD6776	Approved
0.7292	Intermediate Similarity	NPD6781	Approved
0.7292	Intermediate Similarity	NPD6777	Approved
0.7292	Intermediate Similarity	NPD6782	Approved
0.7292	Intermediate Similarity	NPD6779	Approved
0.7292	Intermediate Similarity	NPD6778	Approved
0.7292	Intermediate Similarity	NPD6780	Approved
0.7283	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2797	Approved
0.7278	Intermediate Similarity	NPD1203	Approved
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD3268	Approved
0.7261	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8434	Phase 2
0.7246	Intermediate Similarity	NPD1243	Approved
0.7239	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7208	Intermediate Similarity	NPD7585	Approved
0.7202	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7286	Phase 2
0.7193	Intermediate Similarity	NPD6273	Approved
0.7179	Intermediate Similarity	NPD7680	Approved
0.7175	Intermediate Similarity	NPD6971	Discontinued
0.7169	Intermediate Similarity	NPD6099	Approved
0.7169	Intermediate Similarity	NPD6100	Approved
0.7161	Intermediate Similarity	NPD9268	Approved
0.716	Intermediate Similarity	NPD3764	Approved
0.716	Intermediate Similarity	NPD2313	Discontinued
0.7159	Intermediate Similarity	NPD4288	Approved
0.7157	Intermediate Similarity	NPD7583	Approved
0.7152	Intermediate Similarity	NPD7097	Phase 1
0.715	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7136	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7874	Approved
0.7134	Intermediate Similarity	NPD6355	Discontinued
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.7108	Intermediate Similarity	NPD2799	Discontinued
0.7108	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7003	Approved
0.7101	Intermediate Similarity	NPD8166	Discontinued
0.7097	Intermediate Similarity	NPD9545	Approved
0.7097	Intermediate Similarity	NPD1548	Phase 1
0.7093	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7698	Approved
0.7092	Intermediate Similarity	NPD7697	Approved
0.7092	Intermediate Similarity	NPD7696	Phase 3
0.7089	Intermediate Similarity	NPD9717	Approved
0.7089	Intermediate Similarity	NPD1608	Approved
0.7081	Intermediate Similarity	NPD2861	Phase 2
0.7076	Intermediate Similarity	NPD7390	Discontinued
0.7073	Intermediate Similarity	NPD4307	Phase 2
0.7069	Intermediate Similarity	NPD3455	Phase 2
0.7049	Intermediate Similarity	NPD7177	Discontinued
0.7041	Intermediate Similarity	NPD6823	Phase 2
0.7041	Intermediate Similarity	NPD2800	Approved
0.7035	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7701	Phase 2
0.7033	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6534	Approved
0.7031	Intermediate Similarity	NPD6535	Approved
0.7025	Intermediate Similarity	NPD1610	Phase 2

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