NPASS Compound

Structure

CID326877 OpenBabel06191716192D 34 38 0 0 1 0 0 0 0 0999 V2000 0.2588 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7934 0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 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 -5.1962 -3.0000 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 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 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 -1.7321 0.0000 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 -1.7321 1.0000 0.0000 C 0 0 3 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 1.5000 0.0000 C 0 0 3 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 -4.3301 -1.5000 0.0000 C 0 0 1 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 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 23 1 0 0 0 0 2 23 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 31 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 9 32 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 17 1 0 0 0 0 11 25 1 0 0 0 0 12 32 1 0 0 0 0 13 14 2 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 18 2 0 0 0 0 15 34 1 0 0 0 0 16 24 1 1 0 0 0 16 33 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 33 1 0 0 0 0 20 22 1 0 0 0 0 20 31 1 0 0 0 0 21 24 1 0 0 0 0 21 26 2 0 0 0 0 22 23 1 0 0 0 0 22 27 1 0 0 0 0 23 34 1 0 0 0 0 24 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.15
Volume:	450.325
LogP:	2.876
LogD:	2.707
LogS:	-3.343
# Rotatable Bonds:	3
TPSA:	133.14
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.605
Synthetic Accessibility Score:	4.393
Fsp3:	0.458
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.087
MDCK Permeability:	1.2541639989649411e-05
Pgp-inhibitor:	0.485
Pgp-substrate:	0.922
Human Intestinal Absorption (HIA):	0.084
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.243
Plasma Protein Binding (PPB):	82.25252532958984%
Volume Distribution (VD):	0.804
Pgp-substrate:	14.549131393432617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.654
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.566
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.294
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.782

ADMET: Excretion

Clearance (CL):	4.402
Half-life (T1/2):	0.165

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.896
Drug-inuced Liver Injury (DILI):	0.594
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.455
Maximum Recommended Daily Dose:	0.575
Skin Sensitization:	0.167
Carcinogencity:	0.177
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.079

Download Data

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

Natural Product: NPC326877

Natural Product ID:	NPC326877
*Common Name:**	RTUABMSWXKMPKI-JIEJDMOWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RTUABMSWXKMPKI-JIEJDMOWSA-N
Standard InCHI:	InChI=1S/C24H26O10/c1-23(2)22(27)20(31-5)18-15(34-23)7-11(25)17-19(18)33-16-9-32-12-8-14(30-4)13(29-3)6-10(12)24(16,28)21(17)26/h6-8,16,20,22,25,27-28H,9H2,1-5H3/t16-,20?,22?,24-/m1/s1
SMILES:	CC1(C(C(C2=C(O1)C=C(C3=C2OC4COC5=CC(=C(C=C5C4(C3=O)O)OC)OC)O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510838
PubChem CID:	11762505
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO17729	Tephrosia toxicaria	Species	Geometridae	Eukaryota	n.a.	stem	n.a.	PMID[14510590]
NPO17729	Tephrosia toxicaria	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17729	Tephrosia toxicaria	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17729	Tephrosia toxicaria	Species	Geometridae	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	1
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	6.7	uM	PMID[566599]
NPT27	Others	Unspecified		IC50	=	9100.0	nM	PMID[566599]
NPT2	Others	Unspecified		Ratio	=	1.4	n.a.	PMID[566599]

☑ 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 NPC326877 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	434
0.1-0.2	1744
0.2-0.3	4013
0.3-0.4	10021
0.4-0.5	8283
0.5-0.6	3820
0.6-0.7	4892
0.7-0.8	5332
0.8-0.85	2693
0.85-0.9	1260
0.9-0.95	197
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9812	High Similarity	NPC74559
0.975	High Similarity	NPC177480
0.9568	High Similarity	NPC103307
0.9565	High Similarity	NPC8965
0.9509	High Similarity	NPC121333
0.9506	High Similarity	NPC242395
0.95	High Similarity	NPC41301
0.9444	High Similarity	NPC6588
0.9444	High Similarity	NPC117854
0.9444	High Similarity	NPC477154
0.9441	High Similarity	NPC62261
0.9441	High Similarity	NPC224280
0.9441	High Similarity	NPC234052
0.9437	High Similarity	NPC52204
0.9437	High Similarity	NPC220912
0.9387	High Similarity	NPC152477
0.9383	High Similarity	NPC471213
0.9383	High Similarity	NPC120593
0.9379	High Similarity	NPC146134
0.9375	High Similarity	NPC228383
0.9371	High Similarity	NPC473990
0.9325	High Similarity	NPC158761
0.9321	High Similarity	NPC470457
0.9313	High Similarity	NPC470326
0.9313	High Similarity	NPC174953
0.9259	High Similarity	NPC236521
0.9259	High Similarity	NPC472625
0.9259	High Similarity	NPC273959
0.9259	High Similarity	NPC470459
0.9259	High Similarity	NPC248638
0.9259	High Similarity	NPC152659
0.9255	High Similarity	NPC472632
0.9255	High Similarity	NPC471212
0.9255	High Similarity	NPC173137
0.9255	High Similarity	NPC471499
0.9255	High Similarity	NPC471211
0.9255	High Similarity	NPC134783
0.925	High Similarity	NPC152904
0.9245	High Similarity	NPC146636
0.9226	High Similarity	NPC185275
0.9207	High Similarity	NPC470456
0.9207	High Similarity	NPC295082
0.9207	High Similarity	NPC14662
0.9207	High Similarity	NPC474024
0.9202	High Similarity	NPC7154
0.9202	High Similarity	NPC36916
0.9202	High Similarity	NPC50960
0.9202	High Similarity	NPC36
0.9202	High Similarity	NPC125039
0.9202	High Similarity	NPC7688
0.9202	High Similarity	NPC58223
0.9202	High Similarity	NPC72787
0.9198	High Similarity	NPC474034
0.9198	High Similarity	NPC474033
0.9198	High Similarity	NPC25152
0.9193	High Similarity	NPC263449
0.9193	High Similarity	NPC472630
0.9193	High Similarity	NPC472631
0.9193	High Similarity	NPC287328
0.9193	High Similarity	NPC282009
0.9193	High Similarity	NPC475784
0.9193	High Similarity	NPC471976
0.9187	High Similarity	NPC223787
0.9167	High Similarity	NPC67302
0.9167	High Similarity	NPC265380
0.9162	High Similarity	NPC108202
0.9157	High Similarity	NPC267254
0.9157	High Similarity	NPC186847
0.9157	High Similarity	NPC472454
0.9157	High Similarity	NPC257667
0.9157	High Similarity	NPC156977
0.9146	High Similarity	NPC173292
0.9146	High Similarity	NPC170245
0.9146	High Similarity	NPC472449
0.9146	High Similarity	NPC470462
0.9146	High Similarity	NPC128293
0.9141	High Similarity	NPC474240
0.9141	High Similarity	NPC7483
0.9136	High Similarity	NPC471210
0.9136	High Similarity	NPC474186
0.9136	High Similarity	NPC26326
0.9136	High Similarity	NPC308992
0.9136	High Similarity	NPC474038
0.9136	High Similarity	NPC289771
0.9136	High Similarity	NPC266314
0.9136	High Similarity	NPC472634
0.9136	High Similarity	NPC40037
0.9136	High Similarity	NPC3629
0.9136	High Similarity	NPC61010
0.913	High Similarity	NPC95936
0.913	High Similarity	NPC22192
0.913	High Similarity	NPC250214
0.9125	High Similarity	NPC303255
0.9125	High Similarity	NPC250922
0.9112	High Similarity	NPC324742
0.9107	High Similarity	NPC156635
0.9102	High Similarity	NPC239549
0.9102	High Similarity	NPC236191
0.9102	High Similarity	NPC51774
0.9096	High Similarity	NPC102277
0.9096	High Similarity	NPC472276
0.9096	High Similarity	NPC279209
0.9091	High Similarity	NPC93099
0.9091	High Similarity	NPC260266
0.9091	High Similarity	NPC243877
0.9085	High Similarity	NPC275780
0.9085	High Similarity	NPC239752
0.9085	High Similarity	NPC472450
0.9085	High Similarity	NPC293319
0.9085	High Similarity	NPC326520
0.9085	High Similarity	NPC475888
0.908	High Similarity	NPC261470
0.908	High Similarity	NPC474162
0.908	High Similarity	NPC211107
0.908	High Similarity	NPC474150
0.908	High Similarity	NPC83922
0.908	High Similarity	NPC472448
0.908	High Similarity	NPC229632
0.908	High Similarity	NPC472635
0.9074	High Similarity	NPC474287
0.9074	High Similarity	NPC119209
0.9074	High Similarity	NPC200746
0.9074	High Similarity	NPC118256
0.9074	High Similarity	NPC228785
0.9074	High Similarity	NPC14353
0.9074	High Similarity	NPC246478
0.9074	High Similarity	NPC470183
0.9074	High Similarity	NPC475886
0.9074	High Similarity	NPC192686
0.9074	High Similarity	NPC56085
0.9074	High Similarity	NPC204290
0.9068	High Similarity	NPC284820
0.9068	High Similarity	NPC474836
0.9068	High Similarity	NPC471209
0.9068	High Similarity	NPC469584
0.9068	High Similarity	NPC475267
0.9068	High Similarity	NPC156057
0.9068	High Similarity	NPC472598
0.9068	High Similarity	NPC48208
0.9068	High Similarity	NPC474208
0.9068	High Similarity	NPC162869
0.9068	High Similarity	NPC27337
0.9068	High Similarity	NPC473272
0.9068	High Similarity	NPC165977
0.9068	High Similarity	NPC474055
0.9068	High Similarity	NPC262286
0.9068	High Similarity	NPC78225
0.9068	High Similarity	NPC217677
0.9068	High Similarity	NPC36852
0.9064	High Similarity	NPC148710
0.9062	High Similarity	NPC45849
0.9062	High Similarity	NPC200761
0.9062	High Similarity	NPC37392
0.9062	High Similarity	NPC477503
0.9062	High Similarity	NPC470327
0.9053	High Similarity	NPC471789
0.9053	High Similarity	NPC168584
0.9048	High Similarity	NPC102028
0.9048	High Similarity	NPC142996
0.9042	High Similarity	NPC212038
0.9042	High Similarity	NPC301683
0.9042	High Similarity	NPC81332
0.9042	High Similarity	NPC262580
0.9042	High Similarity	NPC271848
0.9042	High Similarity	NPC289396
0.9036	High Similarity	NPC472381
0.9036	High Similarity	NPC210042
0.9036	High Similarity	NPC95855
0.9036	High Similarity	NPC183036
0.9036	High Similarity	NPC472383
0.903	High Similarity	NPC477517
0.903	High Similarity	NPC39091
0.903	High Similarity	NPC119589
0.9024	High Similarity	NPC306321
0.9024	High Similarity	NPC475985
0.9024	High Similarity	NPC124038
0.9024	High Similarity	NPC186686
0.9024	High Similarity	NPC197168
0.9024	High Similarity	NPC303460
0.9024	High Similarity	NPC189473
0.9024	High Similarity	NPC23298
0.9018	High Similarity	NPC142252
0.9018	High Similarity	NPC474187
0.9018	High Similarity	NPC29876
0.9018	High Similarity	NPC167678
0.9018	High Similarity	NPC40491
0.9018	High Similarity	NPC474239
0.9018	High Similarity	NPC278052
0.9018	High Similarity	NPC198829
0.9018	High Similarity	NPC474351
0.9018	High Similarity	NPC165549
0.9018	High Similarity	NPC475883
0.9012	High Similarity	NPC53545
0.9012	High Similarity	NPC329091
0.9012	High Similarity	NPC476242
0.9012	High Similarity	NPC55738
0.9012	High Similarity	NPC117418
0.9012	High Similarity	NPC100123
0.9006	High Similarity	NPC470600
0.9006	High Similarity	NPC35038

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 NPC326877 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	987
0.2-0.3	2017
0.3-0.4	2577
0.4-0.5	1707
0.5-0.6	913
0.6-0.7	395
0.7-0.8	122
0.8-0.85	35
0.85-0.9	9
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9202	High Similarity	NPD6166	Phase 2
0.9202	High Similarity	NPD6167	Clinical (unspecified phase)
0.9202	High Similarity	NPD6168	Clinical (unspecified phase)
0.8882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8869	High Similarity	NPD7074	Phase 3
0.8841	High Similarity	NPD5494	Approved
0.882	High Similarity	NPD1934	Approved
0.8765	High Similarity	NPD2801	Approved
0.8713	High Similarity	NPD7808	Phase 3
0.8713	High Similarity	NPD4338	Clinical (unspecified phase)
0.8706	High Similarity	NPD6797	Phase 2
0.8698	High Similarity	NPD7054	Approved
0.8655	High Similarity	NPD7251	Discontinued
0.8647	High Similarity	NPD7472	Approved
0.8588	High Similarity	NPD7804	Clinical (unspecified phase)
0.858	High Similarity	NPD4380	Phase 2
0.8563	High Similarity	NPD6959	Discontinued
0.8545	High Similarity	NPD3882	Suspended
0.8494	Intermediate Similarity	NPD7075	Discontinued
0.8488	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD3817	Phase 2
0.8434	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD3818	Discontinued
0.8385	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD5844	Phase 1
0.8364	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD1512	Approved
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD5402	Approved
0.821	Intermediate Similarity	NPD1511	Approved
0.8204	Intermediate Similarity	NPD1465	Phase 2
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.815	Intermediate Similarity	NPD7473	Discontinued
0.8122	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7819	Suspended
0.8063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD1247	Approved
0.8012	Intermediate Similarity	NPD1549	Phase 2
0.7976	Intermediate Similarity	NPD7411	Suspended
0.7921	Intermediate Similarity	NPD6559	Discontinued
0.7898	Intermediate Similarity	NPD3751	Discontinued
0.7886	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6799	Approved
0.7874	Intermediate Similarity	NPD3787	Discontinued
0.7844	Intermediate Similarity	NPD5403	Approved
0.7829	Intermediate Similarity	NPD3926	Phase 2
0.7819	Intermediate Similarity	NPD6780	Approved
0.7819	Intermediate Similarity	NPD6777	Approved
0.7819	Intermediate Similarity	NPD6779	Approved
0.7819	Intermediate Similarity	NPD6781	Approved
0.7819	Intermediate Similarity	NPD6778	Approved
0.7819	Intermediate Similarity	NPD6776	Approved
0.7819	Intermediate Similarity	NPD6782	Approved
0.7814	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD2796	Approved
0.7747	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2800	Approved
0.7725	Intermediate Similarity	NPD5401	Approved
0.7716	Intermediate Similarity	NPD1510	Phase 2
0.7705	Intermediate Similarity	NPD8150	Discontinued
0.7701	Intermediate Similarity	NPD919	Approved
0.7697	Intermediate Similarity	NPD7228	Approved
0.7696	Intermediate Similarity	NPD7698	Approved
0.7696	Intermediate Similarity	NPD7696	Phase 3
0.7696	Intermediate Similarity	NPD7435	Discontinued
0.7696	Intermediate Similarity	NPD7697	Approved
0.7637	Intermediate Similarity	NPD8312	Approved
0.7637	Intermediate Similarity	NPD8313	Approved
0.7629	Intermediate Similarity	NPD7701	Phase 2
0.7619	Intermediate Similarity	NPD2534	Approved
0.7619	Intermediate Similarity	NPD2532	Approved
0.7619	Intermediate Similarity	NPD2533	Approved
0.7602	Intermediate Similarity	NPD7783	Phase 2
0.7602	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7768	Phase 2
0.7578	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1613	Approved
0.7578	Intermediate Similarity	NPD1240	Approved
0.7565	Intermediate Similarity	NPD7870	Phase 2
0.7565	Intermediate Similarity	NPD7871	Phase 2
0.7561	Intermediate Similarity	NPD2935	Discontinued
0.7553	Intermediate Similarity	NPD6535	Approved
0.7553	Intermediate Similarity	NPD6534	Approved
0.7545	Intermediate Similarity	NPD6190	Approved
0.7543	Intermediate Similarity	NPD3749	Approved
0.7539	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7699	Phase 2
0.7526	Intermediate Similarity	NPD7700	Phase 2
0.7514	Intermediate Similarity	NPD37	Approved
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7486	Intermediate Similarity	NPD4965	Approved
0.7486	Intermediate Similarity	NPD4966	Approved
0.7486	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD1607	Approved
0.747	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD943	Approved
0.7462	Intermediate Similarity	NPD7874	Approved
0.7462	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7390	Discontinued
0.743	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7801	Approved
0.7416	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD3027	Phase 3
0.7384	Intermediate Similarity	NPD1653	Approved
0.7382	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3750	Approved
0.7381	Intermediate Similarity	NPD4628	Phase 3
0.7378	Intermediate Similarity	NPD6651	Approved
0.7375	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6823	Phase 2
0.7349	Intermediate Similarity	NPD6099	Approved
0.7349	Intermediate Similarity	NPD6100	Approved
0.7341	Intermediate Similarity	NPD3226	Approved
0.7337	Intermediate Similarity	NPD7685	Pre-registration
0.7337	Intermediate Similarity	NPD7240	Approved
0.7329	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD920	Approved
0.7326	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD230	Phase 1
0.7297	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8319	Approved
0.7296	Intermediate Similarity	NPD8320	Phase 1
0.7289	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7277	Intermediate Similarity	NPD4360	Phase 2
0.7277	Intermediate Similarity	NPD4363	Phase 3
0.7273	Intermediate Similarity	NPD8455	Phase 2
0.7268	Intermediate Similarity	NPD7286	Phase 2
0.7239	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7584	Approved
0.7212	Intermediate Similarity	NPD447	Suspended
0.7209	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2346	Discontinued
0.7198	Intermediate Similarity	NPD2403	Approved
0.7186	Intermediate Similarity	NPD2799	Discontinued
0.7182	Intermediate Similarity	NPD5711	Approved
0.7182	Intermediate Similarity	NPD5710	Approved
0.7176	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7134	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6844	Discontinued
0.7118	Intermediate Similarity	NPD1243	Approved
0.7117	Intermediate Similarity	NPD4908	Phase 1
0.711	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2344	Approved
0.7083	Intermediate Similarity	NPD3748	Approved
0.7076	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2424	Discontinued
0.7052	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6213	Phase 3
0.7047	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6212	Phase 3
0.7045	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2313	Discontinued
0.7021	Intermediate Similarity	NPD7549	Discontinued
0.7019	Intermediate Similarity	NPD7907	Approved
0.7006	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5124	Phase 1
0.7006	Intermediate Similarity	NPD1933	Approved
0.7005	Intermediate Similarity	NPD4111	Phase 1
0.7005	Intermediate Similarity	NPD4665	Approved
0.7	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6233	Phase 2
0.6982	Remote Similarity	NPD7033	Discontinued
0.697	Remote Similarity	NPD2494	Approved
0.697	Remote Similarity	NPD4625	Phase 3
0.697	Remote Similarity	NPD2493	Approved
0.6966	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5242	Approved
0.6954	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2861	Phase 2
0.6951	Remote Similarity	NPD9494	Approved
0.6949	Remote Similarity	NPD7458	Discontinued
0.6946	Remote Similarity	NPD4060	Phase 1
0.6944	Remote Similarity	NPD5353	Approved
0.694	Remote Similarity	NPD8127	Discontinued
0.6936	Remote Similarity	NPD2309	Approved
0.6928	Remote Similarity	NPD6798	Discontinued
0.6928	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6674	Discontinued
0.6905	Remote Similarity	NPD6355	Discontinued
0.6902	Remote Similarity	NPD7229	Phase 3
0.6901	Remote Similarity	NPD7266	Discontinued
0.6894	Remote Similarity	NPD1610	Phase 2
0.6894	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD4361	Phase 2
0.6884	Remote Similarity	NPD3452	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