NPASS Compound

Structure

NPC273578 OpenBabel07101718182D 35 39 0 0 1 0 0 0 0 0999 V2000 -4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1932 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5418 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4049 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6728 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 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 -5.9540 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9540 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 28 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 12 2 0 0 0 0 6 15 1 0 0 0 0 7 12 1 0 0 0 0 7 16 2 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 32 1 0 0 0 0 10 33 1 0 0 0 0 10 34 1 0 0 0 0 11 26 2 0 0 0 0 11 35 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 9 1 6 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 15 28 1 0 0 0 0 16 22 1 0 0 0 0 16 29 1 0 0 0 0 17 23 2 0 0 0 0 17 33 1 0 0 0 0 18 12 1 1 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 24 2 0 0 0 0 20 25 1 6 0 0 0 21 35 1 1 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 23 34 1 0 0 0 0 24 31 1 0 0 0 0 25 27 2 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.15
Volume:	464.984
LogP:	1.954
LogD:	2.291
LogS:	-3.61
# Rotatable Bonds:	7
TPSA:	107.98
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.566
Synthetic Accessibility Score:	4.019
Fsp3:	0.44
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:	-4.852
MDCK Permeability:	3.484469561954029e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204
Plasma Protein Binding (PPB):	89.86519622802734%
Volume Distribution (VD):	1.115
Pgp-substrate:	9.024368286132812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.784
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.724
CYP2C9-substrate:	0.561
CYP2D6-inhibitor:	0.099
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.926

ADMET: Excretion

Clearance (CL):	2.846
Half-life (T1/2):	0.197

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.841
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.135
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.039
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.065
Respiratory Toxicity:	0.665

Download Data

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

Natural Product: NPC273578

Natural Product ID:	NPC273578
*Common Name:**	(7R,8S,7'r,8'r)-(+)-7'-Acetyl-5'-Methoxypicropodophyllin
IUPAC Name:	[(5R,5aS,8aR,9R)-4-methoxy-6-oxo-5-(3,4,5-trimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl] acetate
Synonyms:
Standard InCHIKey:	YYMZKKXIDKRNCK-XVPDYNCKSA-N
Standard InCHI:	InChI=1S/C25H26O10/c1-11(26)35-21-13-8-17-23(34-10-33-17)24(31-5)19(13)18(20-14(21)9-32-25(20)27)12-6-15(28-2)22(30-4)16(7-12)29-3/h6-8,14,18,20-21H,9-10H2,1-5H3/t14-,18+,20+,21-/m0/s1
SMILES:	COc1c2[C@@H](c3cc(OC)c(c(c3)OC)OC)[C@@H]3C(=O)OC[C@@H]3[C@H](c2cc2c1OCO2)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453819
PubChem CID:	636677
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones [CHEMONTID:0000047] Podophyllotoxins

*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
NPO29147	Hernandia ovigera	Species	Hernandiaceae	Eukaryota	n.a.	trunk bark	n.a.	DOI[10.1016/S0040-4039(01)98402-3]
NPO29147	Hernandia ovigera	Species	Hernandiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[12141878]
NPO29147	Hernandia ovigera	Species	Hernandiaceae	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	4.0	ug.mL-1	PMID[454344]

☑ 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 NPC273578 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	398
0.1-0.2	1566
0.2-0.3	3327
0.3-0.4	7639
0.4-0.5	10942
0.5-0.6	4462
0.6-0.7	8308
0.7-0.8	5584
0.8-0.85	320
0.85-0.9	107
0.9-0.95	30
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC13985
0.9795	High Similarity	NPC210642
0.9726	High Similarity	NPC149505
0.9536	High Similarity	NPC19947
0.9536	High Similarity	NPC207584
0.9521	High Similarity	NPC101755
0.9521	High Similarity	NPC304687
0.9521	High Similarity	NPC80230
0.9521	High Similarity	NPC65574
0.9521	High Similarity	NPC104024
0.947	High Similarity	NPC32373
0.947	High Similarity	NPC237946
0.9412	High Similarity	NPC96593
0.9396	High Similarity	NPC303519
0.9392	High Similarity	NPC177476
0.9392	High Similarity	NPC262455
0.9351	High Similarity	NPC288149
0.9286	High Similarity	NPC91634
0.9286	High Similarity	NPC268718
0.9286	High Similarity	NPC119910
0.9286	High Similarity	NPC150943
0.9281	High Similarity	NPC115281
0.9281	High Similarity	NPC181168
0.9281	High Similarity	NPC163527
0.9272	High Similarity	NPC245948
0.9226	High Similarity	NPC152424
0.9226	High Similarity	NPC100465
0.9211	High Similarity	NPC348849
0.9211	High Similarity	NPC178195
0.9178	High Similarity	NPC151423
0.9178	High Similarity	NPC40237
0.9172	High Similarity	NPC222531
0.9108	High Similarity	NPC14294
0.9108	High Similarity	NPC116759
0.9103	High Similarity	NPC209411
0.9103	High Similarity	NPC115624
0.9103	High Similarity	NPC239890
0.9097	High Similarity	NPC474043
0.9085	High Similarity	NPC103197
0.9085	High Similarity	NPC30009
0.9067	High Similarity	NPC40654
0.9067	High Similarity	NPC262804
0.906	High Similarity	NPC87295
0.9054	High Similarity	NPC475000
0.9054	High Similarity	NPC92693
0.9054	High Similarity	NPC218841
0.9048	High Similarity	NPC210354
0.9048	High Similarity	NPC176586
0.9038	High Similarity	NPC470637
0.902	High Similarity	NPC474514
0.8994	High Similarity	NPC306475
0.8986	High Similarity	NPC474288
0.8981	High Similarity	NPC191352
0.8981	High Similarity	NPC258322
0.8974	High Similarity	NPC325122
0.8968	High Similarity	NPC477380
0.8954	High Similarity	NPC104353
0.8938	High Similarity	NPC185498
0.8933	High Similarity	NPC321958
0.8933	High Similarity	NPC193779
0.8933	High Similarity	NPC321696
0.8926	High Similarity	NPC177644
0.8926	High Similarity	NPC143092
0.8926	High Similarity	NPC191158
0.8926	High Similarity	NPC18211
0.891	High Similarity	NPC477885
0.8903	High Similarity	NPC234730
0.8896	High Similarity	NPC65591
0.8896	High Similarity	NPC178574
0.8889	High Similarity	NPC474975
0.8882	High Similarity	NPC85141
0.8882	High Similarity	NPC477698
0.8875	High Similarity	NPC174734
0.8875	High Similarity	NPC474042
0.8867	High Similarity	NPC318286
0.8867	High Similarity	NPC327651
0.8859	High Similarity	NPC218510
0.8859	High Similarity	NPC76415
0.8854	High Similarity	NPC125713
0.8846	High Similarity	NPC115123
0.8846	High Similarity	NPC239113
0.8846	High Similarity	NPC301897
0.8836	High Similarity	NPC11453
0.8831	High Similarity	NPC56184
0.8827	High Similarity	NPC179240
0.8824	High Similarity	NPC24425
0.8812	High Similarity	NPC477884
0.8805	High Similarity	NPC61141
0.88	High Similarity	NPC326144
0.8797	High Similarity	NPC474770
0.8782	High Similarity	NPC202249
0.8782	High Similarity	NPC188962
0.8782	High Similarity	NPC42871
0.8776	High Similarity	NPC196420
0.8767	High Similarity	NPC44245
0.8767	High Similarity	NPC72796
0.8766	High Similarity	NPC164082
0.8765	High Similarity	NPC117911
0.8758	High Similarity	NPC477695
0.8758	High Similarity	NPC668
0.8758	High Similarity	NPC474965
0.8758	High Similarity	NPC293757
0.8758	High Similarity	NPC174512
0.8742	High Similarity	NPC319749
0.8742	High Similarity	NPC474158
0.8727	High Similarity	NPC196771
0.8726	High Similarity	NPC473900
0.8725	High Similarity	NPC218092
0.8725	High Similarity	NPC162851
0.8725	High Similarity	NPC246474
0.872	High Similarity	NPC474568
0.8718	High Similarity	NPC136757
0.871	High Similarity	NPC477699
0.8704	High Similarity	NPC79322
0.8701	High Similarity	NPC316989
0.8701	High Similarity	NPC473989
0.8693	High Similarity	NPC304821
0.8693	High Similarity	NPC252281
0.8693	High Similarity	NPC477375
0.8693	High Similarity	NPC327352
0.8693	High Similarity	NPC198129
0.8688	High Similarity	NPC280778
0.8679	High Similarity	NPC78944
0.8671	High Similarity	NPC19600
0.8667	High Similarity	NPC287124
0.8662	High Similarity	NPC238834
0.8658	High Similarity	NPC216434
0.8658	High Similarity	NPC103448
0.8654	High Similarity	NPC477377
0.8645	High Similarity	NPC477700
0.8642	High Similarity	NPC471923
0.8639	High Similarity	NPC211386
0.8636	High Similarity	NPC477376
0.8636	High Similarity	NPC322426
0.8636	High Similarity	NPC145569
0.8636	High Similarity	NPC216223
0.8636	High Similarity	NPC477374
0.8634	High Similarity	NPC475865
0.8599	High Similarity	NPC312763
0.8599	High Similarity	NPC198461
0.8598	High Similarity	NPC477883
0.859	High Similarity	NPC477378
0.859	High Similarity	NPC475229
0.859	High Similarity	NPC220577
0.8589	High Similarity	NPC471180
0.8589	High Similarity	NPC473531
0.8589	High Similarity	NPC475453
0.8589	High Similarity	NPC474948
0.8589	High Similarity	NPC42230
0.8581	High Similarity	NPC143895
0.8581	High Similarity	NPC209229
0.858	High Similarity	NPC475953
0.858	High Similarity	NPC474647
0.8571	High Similarity	NPC22130
0.8571	High Similarity	NPC116838
0.8571	High Similarity	NPC316676
0.8571	High Similarity	NPC325720
0.8562	High Similarity	NPC72046
0.8562	High Similarity	NPC65183
0.8562	High Similarity	NPC261812
0.8554	High Similarity	NPC107739
0.8553	High Similarity	NPC474036
0.8553	High Similarity	NPC477701
0.8553	High Similarity	NPC166884
0.8553	High Similarity	NPC141569
0.8543	High Similarity	NPC474295
0.8535	High Similarity	NPC308555
0.8535	High Similarity	NPC474606
0.8529	High Similarity	NPC470642
0.8528	High Similarity	NPC320471
0.8528	High Similarity	NPC83049
0.8528	High Similarity	NPC118162
0.8526	High Similarity	NPC475756
0.8526	High Similarity	NPC32079
0.8516	High Similarity	NPC125570
0.8514	High Similarity	NPC49235
0.8514	High Similarity	NPC148893
0.8514	High Similarity	NPC25333
0.8509	High Similarity	NPC15212
0.8503	High Similarity	NPC136750
0.8503	High Similarity	NPC266848
0.8503	High Similarity	NPC263955
0.8503	High Similarity	NPC23593
0.8503	High Similarity	NPC205915
0.8497	Intermediate Similarity	NPC477702
0.8494	Intermediate Similarity	NPC477881
0.8491	Intermediate Similarity	NPC29727
0.8481	Intermediate Similarity	NPC473425
0.8477	Intermediate Similarity	NPC312199
0.8476	Intermediate Similarity	NPC311912
0.8471	Intermediate Similarity	NPC118332
0.8471	Intermediate Similarity	NPC471154
0.8456	Intermediate Similarity	NPC471182
0.8456	Intermediate Similarity	NPC32189
0.8456	Intermediate Similarity	NPC121651
0.8452	Intermediate Similarity	NPC29587
0.8446	Intermediate Similarity	NPC31530
0.8442	Intermediate Similarity	NPC212890
0.8442	Intermediate Similarity	NPC33832
0.8442	Intermediate Similarity	NPC3982

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 NPC273578 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	888
0.2-0.3	1791
0.3-0.4	2716
0.4-0.5	1959
0.5-0.6	930
0.6-0.7	454
0.7-0.8	77
0.8-0.85	6
0.85-0.9	2
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.947	High Similarity	NPD4967	Phase 2
0.947	High Similarity	NPD4965	Approved
0.947	High Similarity	NPD4966	Approved
0.9346	High Similarity	NPD6234	Discontinued
0.9272	High Similarity	NPD37	Approved
0.8938	High Similarity	NPD7228	Approved
0.8861	High Similarity	NPD7199	Phase 2
0.875	High Similarity	NPD7184	Clinical (unspecified phase)
0.872	High Similarity	NPD7240	Approved
0.8452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6232	Discontinued
0.8084	Intermediate Similarity	NPD7473	Discontinued
0.8081	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5494	Approved
0.7989	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7929	Intermediate Similarity	NPD3818	Discontinued
0.7927	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7680	Approved
0.7808	Intermediate Similarity	NPD3705	Approved
0.7798	Intermediate Similarity	NPD7229	Phase 3
0.7758	Intermediate Similarity	NPD3817	Phase 2
0.764	Intermediate Similarity	NPD2533	Approved
0.764	Intermediate Similarity	NPD2532	Approved
0.764	Intermediate Similarity	NPD2534	Approved
0.763	Intermediate Similarity	NPD7074	Phase 3
0.76	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7819	Suspended
0.759	Intermediate Similarity	NPD1465	Phase 2
0.7582	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2438	Suspended
0.7572	Intermediate Similarity	NPD7054	Approved
0.7547	Intermediate Similarity	NPD6674	Discontinued
0.753	Intermediate Similarity	NPD1934	Approved
0.7529	Intermediate Similarity	NPD7472	Approved
0.7485	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7473	Intermediate Similarity	NPD5005	Approved
0.7473	Intermediate Similarity	NPD5006	Approved
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6559	Discontinued
0.7427	Intermediate Similarity	NPD8127	Discontinued
0.7423	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD919	Approved
0.7401	Intermediate Similarity	NPD7808	Phase 3
0.7399	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6166	Phase 2
0.7396	Intermediate Similarity	NPD3882	Suspended
0.7386	Intermediate Similarity	NPD6797	Phase 2
0.7386	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2801	Approved
0.7381	Intermediate Similarity	NPD8455	Phase 2
0.7375	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2979	Phase 3
0.7363	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4420	Approved
0.7345	Intermediate Similarity	NPD7685	Pre-registration
0.7345	Intermediate Similarity	NPD7251	Discontinued
0.7341	Intermediate Similarity	NPD3926	Phase 2
0.7341	Intermediate Similarity	NPD5242	Approved
0.7337	Intermediate Similarity	NPD5353	Approved
0.7326	Intermediate Similarity	NPD6959	Discontinued
0.7305	Intermediate Similarity	NPD7028	Phase 2
0.7296	Intermediate Similarity	NPD3748	Approved
0.729	Intermediate Similarity	NPD3027	Phase 3
0.7289	Intermediate Similarity	NPD1653	Approved
0.7284	Intermediate Similarity	NPD4110	Phase 3
0.7284	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7075	Discontinued
0.725	Intermediate Similarity	NPD6100	Approved
0.725	Intermediate Similarity	NPD6099	Approved
0.725	Intermediate Similarity	NPD2796	Approved
0.7246	Intermediate Similarity	NPD7458	Discontinued
0.7239	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6190	Approved
0.7225	Intermediate Similarity	NPD1247	Approved
0.7219	Intermediate Similarity	NPD6801	Discontinued
0.7219	Intermediate Similarity	NPD1281	Approved
0.7216	Intermediate Similarity	NPD3751	Discontinued
0.7216	Intermediate Similarity	NPD7827	Phase 1
0.7215	Intermediate Similarity	NPD6355	Discontinued
0.7202	Intermediate Similarity	NPD4380	Phase 2
0.7202	Intermediate Similarity	NPD6599	Discontinued
0.72	Intermediate Similarity	NPD17	Approved
0.7197	Intermediate Similarity	NPD8032	Phase 2
0.7178	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8313	Approved
0.7167	Intermediate Similarity	NPD8312	Approved
0.7161	Intermediate Similarity	NPD3018	Phase 2
0.716	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7411	Suspended
0.7152	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.715	Intermediate Similarity	NPD8151	Discontinued
0.7135	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6798	Discontinued
0.7126	Intermediate Similarity	NPD920	Approved
0.7125	Intermediate Similarity	NPD7097	Phase 1
0.7107	Intermediate Similarity	NPD1933	Approved
0.7107	Intermediate Similarity	NPD230	Phase 1
0.7086	Intermediate Similarity	NPD5710	Approved
0.7086	Intermediate Similarity	NPD5711	Approved
0.7081	Intermediate Similarity	NPD7296	Approved
0.7078	Intermediate Similarity	NPD1283	Approved
0.7075	Intermediate Similarity	NPD5283	Phase 1
0.7073	Intermediate Similarity	NPD4628	Phase 3
0.7073	Intermediate Similarity	NPD3750	Approved
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7059	Intermediate Similarity	NPD6385	Approved
0.7059	Intermediate Similarity	NPD6386	Approved
0.7059	Intermediate Similarity	NPD1608	Approved
0.7052	Intermediate Similarity	NPD3749	Approved
0.7051	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1511	Approved
0.7044	Intermediate Similarity	NPD4060	Phase 1
0.7041	Intermediate Similarity	NPD3226	Approved
0.7037	Intermediate Similarity	NPD2531	Phase 2
0.7035	Intermediate Similarity	NPD5402	Approved
0.7025	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5691	Approved
0.702	Intermediate Similarity	NPD1651	Approved
0.7013	Intermediate Similarity	NPD2982	Phase 2
0.7013	Intermediate Similarity	NPD2983	Phase 2
0.7012	Intermediate Similarity	NPD1243	Approved
0.7012	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4908	Phase 1
0.7006	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3657	Discovery
0.6994	Remote Similarity	NPD5762	Approved
0.6994	Remote Similarity	NPD5763	Approved
0.6994	Remote Similarity	NPD7266	Discontinued
0.6994	Remote Similarity	NPD6005	Phase 3
0.6994	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6002	Phase 3
0.6994	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6004	Phase 3
0.6981	Remote Similarity	NPD6233	Phase 2
0.6979	Remote Similarity	NPD7435	Discontinued
0.6978	Remote Similarity	NPD2971	Approved
0.6978	Remote Similarity	NPD2968	Approved
0.6975	Remote Similarity	NPD7033	Discontinued
0.6973	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6273	Approved
0.6964	Remote Similarity	NPD1512	Approved
0.6957	Remote Similarity	NPD8434	Phase 2
0.6941	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3620	Phase 2
0.6937	Remote Similarity	NPD4140	Approved
0.6931	Remote Similarity	NPD2975	Approved
0.6931	Remote Similarity	NPD2974	Approved
0.6931	Remote Similarity	NPD2973	Approved
0.6923	Remote Similarity	NPD3266	Approved
0.6923	Remote Similarity	NPD3267	Approved
0.6911	Remote Similarity	NPD6776	Approved
0.6911	Remote Similarity	NPD6782	Approved
0.6911	Remote Similarity	NPD6780	Approved
0.6911	Remote Similarity	NPD4580	Approved
0.6911	Remote Similarity	NPD6777	Approved
0.6911	Remote Similarity	NPD6781	Approved
0.6911	Remote Similarity	NPD6779	Approved
0.6911	Remote Similarity	NPD6778	Approved
0.691	Remote Similarity	NPD4481	Phase 3
0.691	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7768	Phase 2
0.689	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6663	Approved
0.6875	Remote Similarity	NPD6746	Phase 2
0.6871	Remote Similarity	NPD1510	Phase 2
0.6857	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4625	Phase 3
0.6848	Remote Similarity	NPD1549	Phase 2
0.6842	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2935	Discontinued
0.6826	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5403	Approved
0.6818	Remote Similarity	NPD7783	Phase 2
0.6818	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2797	Approved
0.6813	Remote Similarity	NPD3764	Approved
0.6813	Remote Similarity	NPD3268	Approved
0.6807	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5401	Approved
0.6805	Remote Similarity	NPD3146	Approved
0.6805	Remote Similarity	NPD3688	Clinical (unspecified phase)

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