NPASS Compound

Structure

CID40654 OpenBabel06191715372D 29 33 0 0 1 0 0 0 0 0999 V2000 -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 2.4049 1.0000 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 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 0.5000 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 1.5388 0.5000 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 5.0029 0.5000 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 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 2.4049 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 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 0.5878 -0.8090 0.0000 C 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 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 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 11 1 0 0 0 0 4 13 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 7 18 2 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 10 29 1 0 0 0 0 11 14 1 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 20 22 1 0 0 0 0 21 26 1 0 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.12
Volume:	386.726
LogP:	3.521
LogD:	3.688
LogS:	-5.209
# Rotatable Bonds:	4
TPSA:	79.52
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.562
Synthetic Accessibility Score:	3.353
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.925
MDCK Permeability:	1.839569267758634e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.079
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	99.0660629272461%
Volume Distribution (VD):	0.728
Pgp-substrate:	1.0433379411697388%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.675
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.831
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.369
CYP2D6-substrate:	0.802
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.928

ADMET: Excretion

Clearance (CL):	11.673
Half-life (T1/2):	0.291

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.761
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.176
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.41
Carcinogencity:	0.164
Eye Corrosion:	0.003
Eye Irritation:	0.61
Respiratory Toxicity:	0.791

Download Data

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

Natural Product: NPC40654

Natural Product ID:	NPC40654
*Common Name:**	5-(3,4,5-Trimethoxyphenyl)-8,9-Dihydro-5H-[2]Benzofuro[5,6-F][1,3]Benzodioxol-6-One
IUPAC Name:	5-(3,4,5-trimethoxyphenyl)-8,9-dihydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
Synonyms:
Standard InCHIKey:	OPGVEBTYBAOEHZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H20O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,19H,4,9-10H2,1-3H3
SMILES:	COc1cc(cc(c1OC)OC)C1C2=C(COC2=O)Cc2c1cc1OCOc1c2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL330639
PubChem CID:	10408428
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans [CHEMONTID:0004792] Furanonaphthodioxoles

*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
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	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	2
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	0.00825	ug.mL-1	PMID[459662]
NPT27	Others	Unspecified		IC50	=	27.5	ug.mL-1	PMID[459662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Selectivity index	>	3333.0	n.a.	PMID[459662]

☑ 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 NPC40654 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	380
0.1-0.2	1512
0.2-0.3	3415
0.3-0.4	8899
0.4-0.5	10181
0.5-0.6	3773
0.6-0.7	8989
0.7-0.8	5134
0.8-0.85	273
0.85-0.9	108
0.9-0.95	31
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC262804
0.951	High Similarity	NPC104024
0.951	High Similarity	NPC101755
0.951	High Similarity	NPC304687
0.951	High Similarity	NPC80230
0.951	High Similarity	NPC65574
0.9379	High Similarity	NPC262455
0.9379	High Similarity	NPC177476
0.9315	High Similarity	NPC149505
0.9252	High Similarity	NPC13985
0.9252	High Similarity	NPC210642
0.9167	High Similarity	NPC475000
0.9161	High Similarity	NPC176586
0.9161	High Similarity	NPC210354
0.9161	High Similarity	NPC40237
0.9161	High Similarity	NPC151423
0.9133	High Similarity	NPC234730
0.9067	High Similarity	NPC103197
0.9067	High Similarity	NPC273578
0.9067	High Similarity	NPC30009
0.9041	High Similarity	NPC193779
0.9034	High Similarity	NPC92693
0.9034	High Similarity	NPC191158
0.9034	High Similarity	NPC177644
0.9034	High Similarity	NPC218841
0.8961	High Similarity	NPC209411
0.8961	High Similarity	NPC239890
0.8954	High Similarity	NPC474043
0.8947	High Similarity	NPC32373
0.8947	High Similarity	NPC473900
0.8947	High Similarity	NPC237946
0.894	High Similarity	NPC348849
0.894	High Similarity	NPC178195
0.8889	High Similarity	NPC19947
0.8889	High Similarity	NPC207584
0.8889	High Similarity	NPC115281
0.8889	High Similarity	NPC181168
0.8889	High Similarity	NPC163527
0.8874	High Similarity	NPC245948
0.8873	High Similarity	NPC72796
0.8873	High Similarity	NPC44245
0.8873	High Similarity	NPC211386
0.8867	High Similarity	NPC303519
0.8844	High Similarity	NPC474158
0.8836	High Similarity	NPC474288
0.8811	High Similarity	NPC11453
0.8774	High Similarity	NPC96593
0.8774	High Similarity	NPC150943
0.8774	High Similarity	NPC268718
0.8774	High Similarity	NPC470637
0.8774	High Similarity	NPC91634
0.8774	High Similarity	NPC119910
0.8758	High Similarity	NPC188962
0.8758	High Similarity	NPC42871
0.8758	High Similarity	NPC202249
0.8742	High Similarity	NPC477700
0.8742	High Similarity	NPC32079
0.8733	High Similarity	NPC174512
0.8733	High Similarity	NPC145569
0.8733	High Similarity	NPC216223
0.8733	High Similarity	NPC477698
0.8733	High Similarity	NPC477695
0.8733	High Similarity	NPC85141
0.8733	High Similarity	NPC668
0.8733	High Similarity	NPC474965
0.8733	High Similarity	NPC293757
0.8718	High Similarity	NPC100465
0.8718	High Similarity	NPC115624
0.8718	High Similarity	NPC191352
0.8718	High Similarity	NPC258322
0.8718	High Similarity	NPC288149
0.8718	High Similarity	NPC152424
0.8701	High Similarity	NPC115123
0.8701	High Similarity	NPC477380
0.8701	High Similarity	NPC239113
0.8699	High Similarity	NPC246474
0.8699	High Similarity	NPC218092
0.8699	High Similarity	NPC162851
0.8681	High Similarity	NPC143895
0.8675	High Similarity	NPC316989
0.8667	High Similarity	NPC477375
0.8667	High Similarity	NPC252281
0.8667	High Similarity	NPC198129
0.8667	High Similarity	NPC327352
0.8658	High Similarity	NPC321696
0.8658	High Similarity	NPC321958
0.8649	High Similarity	NPC18211
0.8645	High Similarity	NPC477885
0.8621	High Similarity	NPC196420
0.8618	High Similarity	NPC164082
0.8616	High Similarity	NPC474042
0.8616	High Similarity	NPC174734
0.8609	High Similarity	NPC477374
0.8609	High Similarity	NPC322426
0.8609	High Similarity	NPC477376
0.8608	High Similarity	NPC14294
0.8608	High Similarity	NPC116759
0.8601	High Similarity	NPC205915
0.8599	High Similarity	NPC319749
0.8592	High Similarity	NPC192255
0.8591	High Similarity	NPC327651
0.8591	High Similarity	NPC318286
0.859	High Similarity	NPC125713
0.859	High Similarity	NPC325122
0.8581	High Similarity	NPC301897
0.8581	High Similarity	NPC218510
0.8581	High Similarity	NPC76415
0.8562	High Similarity	NPC104353
0.8562	High Similarity	NPC56184
0.8562	High Similarity	NPC477699
0.8553	High Similarity	NPC24425
0.8553	High Similarity	NPC222531
0.8553	High Similarity	NPC475170
0.8544	High Similarity	NPC280778
0.8544	High Similarity	NPC61141
0.8543	High Similarity	NPC304821
0.8535	High Similarity	NPC78944
0.8533	High Similarity	NPC87295
0.8531	High Similarity	NPC72046
0.8531	High Similarity	NPC261812
0.8531	High Similarity	NPC65183
0.8526	High Similarity	NPC19600
0.8523	High Similarity	NPC143092
0.8523	High Similarity	NPC474036
0.8523	High Similarity	NPC326144
0.8514	High Similarity	NPC287124
0.8509	High Similarity	NPC117911
0.8506	High Similarity	NPC474514
0.8506	High Similarity	NPC65591
0.8506	High Similarity	NPC477377
0.8506	High Similarity	NPC144162
0.8506	High Similarity	NPC178574
0.85	High Similarity	NPC306475
0.8487	Intermediate Similarity	NPC127827
0.8472	Intermediate Similarity	NPC266848
0.8472	Intermediate Similarity	NPC136750
0.8456	Intermediate Similarity	NPC106920
0.8456	Intermediate Similarity	NPC470811
0.8456	Intermediate Similarity	NPC273657
0.8456	Intermediate Similarity	NPC477697
0.8456	Intermediate Similarity	NPC477696
0.8452	Intermediate Similarity	NPC136757
0.8452	Intermediate Similarity	NPC198461
0.8452	Intermediate Similarity	NPC312763
0.8447	Intermediate Similarity	NPC79322
0.8447	Intermediate Similarity	NPC185498
0.8442	Intermediate Similarity	NPC475229
0.8442	Intermediate Similarity	NPC477378
0.8442	Intermediate Similarity	NPC220577
0.8438	Intermediate Similarity	NPC477884
0.8431	Intermediate Similarity	NPC475722
0.8428	Intermediate Similarity	NPC116838
0.8428	Intermediate Similarity	NPC22130
0.8425	Intermediate Similarity	NPC230968
0.8425	Intermediate Similarity	NPC102260
0.8425	Intermediate Similarity	NPC209229
0.8418	Intermediate Similarity	NPC474770
0.8414	Intermediate Similarity	NPC31530
0.8414	Intermediate Similarity	NPC19890
0.8414	Intermediate Similarity	NPC110958
0.8411	Intermediate Similarity	NPC472560
0.84	Intermediate Similarity	NPC166884
0.84	Intermediate Similarity	NPC15743
0.84	Intermediate Similarity	NPC477701
0.84	Intermediate Similarity	NPC141569
0.8397	Intermediate Similarity	NPC238834
0.8389	Intermediate Similarity	NPC46180
0.8387	Intermediate Similarity	NPC16791
0.8387	Intermediate Similarity	NPC53669
0.8387	Intermediate Similarity	NPC217708
0.8387	Intermediate Similarity	NPC126405
0.8387	Intermediate Similarity	NPC77237
0.8387	Intermediate Similarity	NPC297271
0.8387	Intermediate Similarity	NPC308739
0.8387	Intermediate Similarity	NPC24562
0.8385	Intermediate Similarity	NPC83049
0.8385	Intermediate Similarity	NPC118162
0.8385	Intermediate Similarity	NPC320471
0.8378	Intermediate Similarity	NPC103448
0.8378	Intermediate Similarity	NPC216434
0.8377	Intermediate Similarity	NPC224472
0.8377	Intermediate Similarity	NPC474975
0.8367	Intermediate Similarity	NPC166184
0.8366	Intermediate Similarity	NPC472567
0.8365	Intermediate Similarity	NPC15212
0.8356	Intermediate Similarity	NPC189474
0.8356	Intermediate Similarity	NPC148893
0.8356	Intermediate Similarity	NPC25333
0.8356	Intermediate Similarity	NPC49235
0.8355	Intermediate Similarity	NPC25496
0.8354	Intermediate Similarity	NPC68619
0.8354	Intermediate Similarity	NPC474568
0.8344	Intermediate Similarity	NPC477702
0.8344	Intermediate Similarity	NPC179240
0.8333	Intermediate Similarity	NPC54179
0.8333	Intermediate Similarity	NPC137920
0.8333	Intermediate Similarity	NPC125134
0.8333	Intermediate Similarity	NPC311912
0.8333	Intermediate Similarity	NPC86455
0.8323	Intermediate Similarity	NPC476434

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 NPC40654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	931
0.2-0.3	1617
0.3-0.4	2718
0.4-0.5	1903
0.5-0.6	1082
0.6-0.7	489
0.7-0.8	86
0.8-0.85	3
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD4966	Approved
0.8947	High Similarity	NPD4967	Phase 2
0.8947	High Similarity	NPD4965	Approved
0.8874	High Similarity	NPD37	Approved
0.8831	High Similarity	NPD6234	Discontinued
0.8543	High Similarity	NPD6980	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7199	Phase 2
0.8467	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7228	Approved
0.8375	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7240	Approved
0.8095	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD3705	Approved
0.7911	Intermediate Similarity	NPD7028	Phase 2
0.7758	Intermediate Similarity	NPD6232	Discontinued
0.7744	Intermediate Similarity	NPD5494	Approved
0.7738	Intermediate Similarity	NPD5844	Phase 1
0.7733	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7473	Discontinued
0.7697	Intermediate Similarity	NPD3748	Approved
0.7647	Intermediate Similarity	NPD2438	Suspended
0.7607	Intermediate Similarity	NPD3817	Phase 2
0.7574	Intermediate Similarity	NPD3818	Discontinued
0.7564	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2979	Phase 3
0.7546	Intermediate Similarity	NPD7819	Suspended
0.7517	Intermediate Similarity	NPD1281	Approved
0.7484	Intermediate Similarity	NPD2532	Approved
0.7484	Intermediate Similarity	NPD2533	Approved
0.7484	Intermediate Similarity	NPD2534	Approved
0.747	Intermediate Similarity	NPD919	Approved
0.7455	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4110	Phase 3
0.7452	Intermediate Similarity	NPD3750	Approved
0.7436	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6559	Discontinued
0.7396	Intermediate Similarity	NPD5242	Approved
0.7391	Intermediate Similarity	NPD7680	Approved
0.7386	Intermediate Similarity	NPD1933	Approved
0.7384	Intermediate Similarity	NPD7074	Phase 3
0.7381	Intermediate Similarity	NPD8127	Discontinued
0.7378	Intermediate Similarity	NPD1934	Approved
0.7376	Intermediate Similarity	NPD5283	Phase 1
0.7368	Intermediate Similarity	NPD8032	Phase 2
0.7365	Intermediate Similarity	NPD1283	Approved
0.7351	Intermediate Similarity	NPD3027	Phase 3
0.7349	Intermediate Similarity	NPD3882	Suspended
0.7337	Intermediate Similarity	NPD5005	Approved
0.7337	Intermediate Similarity	NPD7229	Phase 3
0.7337	Intermediate Similarity	NPD5006	Approved
0.7333	Intermediate Similarity	NPD1465	Phase 2
0.7333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7054	Approved
0.731	Intermediate Similarity	NPD1651	Approved
0.731	Intermediate Similarity	NPD5691	Approved
0.7308	Intermediate Similarity	NPD2531	Phase 2
0.7292	Intermediate Similarity	NPD5536	Phase 2
0.7289	Intermediate Similarity	NPD5353	Approved
0.7283	Intermediate Similarity	NPD7472	Approved
0.7278	Intermediate Similarity	NPD6674	Discontinued
0.726	Intermediate Similarity	NPD17	Approved
0.7257	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6599	Discontinued
0.7239	Intermediate Similarity	NPD1653	Approved
0.7233	Intermediate Similarity	NPD4628	Phase 3
0.7233	Intermediate Similarity	NPD8166	Discontinued
0.723	Intermediate Similarity	NPD2981	Phase 2
0.7229	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2801	Approved
0.7222	Intermediate Similarity	NPD6273	Approved
0.7213	Intermediate Similarity	NPD4420	Approved
0.7207	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6799	Approved
0.72	Intermediate Similarity	NPD7685	Pre-registration
0.7197	Intermediate Similarity	NPD2796	Approved
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.7193	Intermediate Similarity	NPD3926	Phase 2
0.7181	Intermediate Similarity	NPD2982	Phase 2
0.7181	Intermediate Similarity	NPD2983	Phase 2
0.7161	Intermediate Similarity	NPD230	Phase 1
0.7161	Intermediate Similarity	NPD6355	Discontinued
0.7159	Intermediate Similarity	NPD7808	Phase 3
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7117	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1608	Approved
0.7108	Intermediate Similarity	NPD6386	Approved
0.7108	Intermediate Similarity	NPD6385	Approved
0.7105	Intermediate Similarity	NPD3018	Phase 2
0.7102	Intermediate Similarity	NPD7251	Discontinued
0.7101	Intermediate Similarity	NPD7075	Discontinued
0.7101	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4357	Discontinued
0.7097	Intermediate Similarity	NPD4060	Phase 1
0.7089	Intermediate Similarity	NPD6100	Approved
0.7089	Intermediate Similarity	NPD6099	Approved
0.7086	Intermediate Similarity	NPD3266	Approved
0.7086	Intermediate Similarity	NPD3267	Approved
0.7086	Intermediate Similarity	NPD2797	Approved
0.7083	Intermediate Similarity	NPD7827	Phase 1
0.7081	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3764	Approved
0.7076	Intermediate Similarity	NPD1247	Approved
0.7066	Intermediate Similarity	NPD6801	Discontinued
0.7063	Intermediate Similarity	NPD1243	Approved
0.7055	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6166	Phase 2
0.7052	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3657	Discovery
0.7041	Intermediate Similarity	NPD7768	Phase 2
0.7027	Intermediate Similarity	NPD4626	Approved
0.7024	Intermediate Similarity	NPD8455	Phase 2
0.702	Intermediate Similarity	NPD1876	Approved
0.7013	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6873	Phase 2
0.7006	Intermediate Similarity	NPD7411	Suspended
0.7	Intermediate Similarity	NPD6971	Discontinued
0.6994	Remote Similarity	NPD1511	Approved
0.6993	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4140	Approved
0.6987	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3620	Phase 2
0.6987	Remote Similarity	NPD1613	Approved
0.6987	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2935	Discontinued
0.6977	Remote Similarity	NPD6959	Discontinued
0.6975	Remote Similarity	NPD6190	Approved
0.6975	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3751	Discontinued
0.697	Remote Similarity	NPD920	Approved
0.6968	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3268	Approved
0.6968	Remote Similarity	NPD1296	Phase 2
0.6968	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD5585	Approved
0.6957	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4481	Phase 3
0.6954	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4908	Phase 1
0.6946	Remote Similarity	NPD4380	Phase 2
0.6941	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5763	Approved
0.6937	Remote Similarity	NPD5762	Approved
0.6936	Remote Similarity	NPD3787	Discontinued
0.6936	Remote Similarity	NPD5710	Approved
0.6936	Remote Similarity	NPD5711	Approved
0.6933	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8312	Approved
0.6927	Remote Similarity	NPD8313	Approved
0.6923	Remote Similarity	NPD6233	Phase 2
0.6923	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6663	Approved
0.6923	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4108	Discontinued
0.6918	Remote Similarity	NPD1510	Phase 2
0.6914	Remote Similarity	NPD7003	Approved
0.6914	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1512	Approved
0.6909	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4625	Phase 3
0.6903	Remote Similarity	NPD7095	Approved
0.6901	Remote Similarity	NPD3749	Approved
0.6886	Remote Similarity	NPD4005	Discontinued
0.6882	Remote Similarity	NPD5402	Approved
0.6882	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4288	Approved
0.6875	Remote Similarity	NPD1551	Phase 2
0.6867	Remote Similarity	NPD5403	Approved
0.6859	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7296	Approved
0.6848	Remote Similarity	NPD5401	Approved
0.6848	Remote Similarity	NPD3146	Approved
0.6848	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1357	Approved
0.6842	Remote Similarity	NPD4749	Approved
0.6842	Remote Similarity	NPD5327	Phase 3
0.6839	Remote Similarity	NPD6832	Phase 2
0.6835	Remote Similarity	NPD5124	Phase 1
0.6835	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2346	Discontinued
0.6832	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6004	Phase 3
0.6832	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6005	Phase 3

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