NPASS Compound

Structure

CID84181 OpenBabel06191715422D 38 42 0 0 1 0 0 0 0 0999 V2000 -2.6924 -5.1193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1722 3.7221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1878 -1.5480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6676 0.1508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1014 -1.9547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5812 0.5575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4833 -3.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9632 1.7331 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 -1.6641 0.1627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1439 -1.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3788 -2.1358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8586 0.7385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2573 -0.7509 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2059 -2.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6857 1.5520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3969 -3.5370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8767 2.1398 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 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4653 -1.7290 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0549 0.3318 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2628 -0.6463 0.0000 C 0 0 1 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 -5.1194 -3.3560 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5993 1.9587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5014 -4.5315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9812 3.1343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9209 0.8318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5992 -2.2290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 33 1 0 0 0 0 2 34 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 27 1 0 0 0 0 10 14 1 0 0 0 0 10 35 1 0 0 0 0 11 26 1 0 0 0 0 11 36 1 0 0 0 0 13 24 1 0 0 0 0 14 23 1 0 0 0 0 14 26 1 1 0 0 0 15 17 2 0 0 0 0 15 28 1 0 0 0 0 16 18 2 0 0 0 0 16 29 1 0 0 0 0 17 33 1 0 0 0 0 18 34 1 0 0 0 0 19 9 1 6 0 0 0 19 20 1 0 0 0 0 19 37 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 22 1 0 0 0 0 21 31 1 6 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 12 1 6 0 0 0 23 36 1 0 0 0 0 24 26 1 6 0 0 0 24 35 1 0 0 0 0 25 37 1 0 0 0 0 25 38 1 6 0 0 0 26 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.19
Volume:	505.134
LogP:	0.239
LogD:	0.622
LogS:	-4.414
# Rotatable Bonds:	7
TPSA:	176.76
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	4.726
Fsp3:	0.538
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.413
MDCK Permeability:	1.3054287592240144e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.909
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	75.99347686767578%
Volume Distribution (VD):	0.329
Pgp-substrate:	23.009496688842773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.797
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.478
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.238
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.3
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	4.05
Half-life (T1/2):	0.737

ADMET: Toxicity

hERG Blockers:	0.435
Human Hepatotoxicity (H-HT):	0.414
Drug-inuced Liver Injury (DILI):	0.697
AMES Toxicity:	0.59
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.911
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.052
Respiratory Toxicity:	0.531

Download Data

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

Natural Product: NPC84181

Natural Product ID:	NPC84181
*Common Name:**	(+)-1-Hydroxypinoresinol 1-O-Beta-D-Glucopyranoside
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(3R,3aS,6S,6aR)-3,6-bis(4-hydroxy-3-methoxyphenyl)-3,4,6,6a-tetrahydro-1H-furo[3,4-c]furan-3a-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	DRAPQDCEBKBPQE-ACFZRETJSA-N
Standard InCHI:	InChI=1S/C26H32O12/c1-33-17-7-12(3-5-15(17)28)23-14-10-35-24(13-4-6-16(29)18(8-13)34-2)26(14,11-36-23)38-25-22(32)21(31)20(30)19(9-27)37-25/h3-8,14,19-25,27-32H,9-11H2,1-2H3/t14-,19-,20-,21+,22-,23-,24-,25+,26-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@]23CO[C@@H]([C@H]2CO[C@@H]3c2ccc(c(c2)OC)O)c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517863
PubChem CID:	13995449
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

*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
NPO12110	Bauhinia tarapotensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473417]
NPO6021	Scorzonera humilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5422	Othonna quinquedentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12110	Bauhinia tarapotensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3015	Aquilegia alpina	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6021	Scorzonera humilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9059	Vernonia pectoralis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	3

Activity Type	# Activity
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	20300.0	nM	PMID[523401]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.935	n.a.	PMID[523401]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	10.7	n.a.	PMID[523401]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	8.5	n.a.	PMID[523401]

☑ 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 NPC84181 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	1286
0.2-0.3	3346
0.3-0.4	8374
0.4-0.5	10106
0.5-0.6	6857
0.6-0.7	8430
0.7-0.8	3085
0.8-0.85	464
0.85-0.9	268
0.9-0.95	57
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC477898
0.9855	High Similarity	NPC112861
0.9783	High Similarity	NPC18979
0.9783	High Similarity	NPC22150
0.9783	High Similarity	NPC38041
0.9783	High Similarity	NPC279298
0.9779	High Similarity	NPC472711
0.971	High Similarity	NPC470235
0.971	High Similarity	NPC129417
0.971	High Similarity	NPC283995
0.9638	High Similarity	NPC46092
0.9638	High Similarity	NPC470950
0.9638	High Similarity	NPC185307
0.9632	High Similarity	NPC156376
0.9577	High Similarity	NPC475224
0.9577	High Similarity	NPC98624
0.9565	High Similarity	NPC246947
0.9565	High Similarity	NPC476356
0.9507	High Similarity	NPC286235
0.9507	High Similarity	NPC55158
0.9507	High Similarity	NPC51328
0.95	High Similarity	NPC469586
0.9493	High Similarity	NPC471908
0.9485	High Similarity	NPC52277
0.9485	High Similarity	NPC199459
0.9485	High Similarity	NPC177035
0.9437	High Similarity	NPC248132
0.9437	High Similarity	NPC130449
0.9429	High Similarity	NPC472713
0.9429	High Similarity	NPC118385
0.9429	High Similarity	NPC187774
0.9429	High Similarity	NPC472712
0.9429	High Similarity	NPC473046
0.9416	High Similarity	NPC304152
0.9412	High Similarity	NPC135777
0.9412	High Similarity	NPC142547
0.9412	High Similarity	NPC101624
0.9412	High Similarity	NPC184938
0.9366	High Similarity	NPC15956
0.9366	High Similarity	NPC213074
0.9366	High Similarity	NPC39657
0.9366	High Similarity	NPC31325
0.9366	High Similarity	NPC224674
0.9366	High Similarity	NPC114505
0.9366	High Similarity	NPC193473
0.9366	High Similarity	NPC275284
0.9357	High Similarity	NPC278961
0.9357	High Similarity	NPC113680
0.9348	High Similarity	NPC123526
0.9348	High Similarity	NPC193666
0.9348	High Similarity	NPC88640
0.9338	High Similarity	NPC470881
0.9296	High Similarity	NPC205796
0.9296	High Similarity	NPC276753
0.9286	High Similarity	NPC472714
0.9286	High Similarity	NPC5262
0.9286	High Similarity	NPC302506
0.9275	High Similarity	NPC138738
0.9275	High Similarity	NPC470413
0.9265	High Similarity	NPC169973
0.9265	High Similarity	NPC6836
0.9225	High Similarity	NPC286245
0.9225	High Similarity	NPC43508
0.9225	High Similarity	NPC272619
0.9225	High Similarity	NPC476301
0.9197	High Similarity	NPC35731
0.9191	High Similarity	NPC252833
0.9191	High Similarity	NPC219671
0.9191	High Similarity	NPC104077
0.9191	High Similarity	NPC147616
0.9191	High Similarity	NPC259742
0.9191	High Similarity	NPC4940
0.9191	High Similarity	NPC207400
0.9191	High Similarity	NPC106739
0.9191	High Similarity	NPC471505
0.9191	High Similarity	NPC181049
0.9167	High Similarity	NPC226153
0.9167	High Similarity	NPC304048
0.9155	High Similarity	NPC179521
0.9155	High Similarity	NPC253015
0.9155	High Similarity	NPC217635
0.9155	High Similarity	NPC471065
0.9155	High Similarity	NPC79429
0.9155	High Similarity	NPC471667
0.9155	High Similarity	NPC471063
0.9149	High Similarity	NPC48309
0.9143	High Similarity	NPC106944
0.9143	High Similarity	NPC177868
0.913	High Similarity	NPC18576
0.913	High Similarity	NPC174191
0.9118	High Similarity	NPC158079
0.9118	High Similarity	NPC40432
0.9118	High Similarity	NPC277804
0.9118	High Similarity	NPC65942
0.9118	High Similarity	NPC7171
0.9118	High Similarity	NPC27843
0.9118	High Similarity	NPC248307
0.9118	High Similarity	NPC476345
0.9118	High Similarity	NPC161557
0.9118	High Similarity	NPC228346
0.9118	High Similarity	NPC115207
0.9103	High Similarity	NPC44452
0.9085	High Similarity	NPC185071
0.9085	High Similarity	NPC298317
0.9085	High Similarity	NPC265154
0.9085	High Similarity	NPC12728
0.9085	High Similarity	NPC255566
0.906	High Similarity	NPC11411
0.9058	High Similarity	NPC47181
0.9058	High Similarity	NPC476411
0.9058	High Similarity	NPC187194
0.9048	High Similarity	NPC478268
0.9044	High Similarity	NPC174495
0.9044	High Similarity	NPC242807
0.9044	High Similarity	NPC275950
0.9044	High Similarity	NPC181079
0.9044	High Similarity	NPC153739
0.9044	High Similarity	NPC42300
0.9044	High Similarity	NPC145305
0.9044	High Similarity	NPC173308
0.9044	High Similarity	NPC241522
0.9044	High Similarity	NPC92164
0.9044	High Similarity	NPC257582
0.9044	High Similarity	NPC77040
0.9044	High Similarity	NPC64201
0.9044	High Similarity	NPC187998
0.9041	High Similarity	NPC472710
0.9041	High Similarity	NPC472709
0.9028	High Similarity	NPC93610
0.9028	High Similarity	NPC241846
0.9028	High Similarity	NPC212890
0.9021	High Similarity	NPC25292
0.9021	High Similarity	NPC473045
0.9021	High Similarity	NPC110063
0.9014	High Similarity	NPC253878
0.9014	High Similarity	NPC189115
0.9014	High Similarity	NPC469559
0.9007	High Similarity	NPC55793
0.9	High Similarity	NPC283949
0.9	High Similarity	NPC195196
0.9	High Similarity	NPC474039
0.9	High Similarity	NPC101807
0.9	High Similarity	NPC185908
0.9	High Similarity	NPC469981
0.8993	High Similarity	NPC38699
0.8986	High Similarity	NPC25821
0.8986	High Similarity	NPC115466
0.8986	High Similarity	NPC245615
0.8986	High Similarity	NPC299706
0.8986	High Similarity	NPC61604
0.8973	High Similarity	NPC55715
0.8973	High Similarity	NPC35877
0.8973	High Similarity	NPC95392
0.8971	High Similarity	NPC475875
0.8971	High Similarity	NPC307110
0.8958	High Similarity	NPC475096
0.8958	High Similarity	NPC477702
0.8951	High Similarity	NPC473044
0.8944	High Similarity	NPC471414
0.8944	High Similarity	NPC469661
0.8933	High Similarity	NPC163635
0.8933	High Similarity	NPC478055
0.8929	High Similarity	NPC471988
0.8929	High Similarity	NPC77861
0.8913	High Similarity	NPC254275
0.8912	High Similarity	NPC188393
0.8912	High Similarity	NPC470934
0.8904	High Similarity	NPC166584
0.8904	High Similarity	NPC270751
0.8904	High Similarity	NPC301961
0.8897	High Similarity	NPC184733
0.8897	High Similarity	NPC474178
0.8897	High Similarity	NPC11258
0.8897	High Similarity	NPC57119
0.8897	High Similarity	NPC226862
0.8897	High Similarity	NPC282703
0.8897	High Similarity	NPC252307
0.8897	High Similarity	NPC99515
0.8897	High Similarity	NPC45774
0.8897	High Similarity	NPC245826
0.8897	High Similarity	NPC128208
0.8897	High Similarity	NPC129570
0.8897	High Similarity	NPC165128
0.8897	High Similarity	NPC190714
0.8897	High Similarity	NPC470084
0.8897	High Similarity	NPC158471
0.8897	High Similarity	NPC21867
0.8889	High Similarity	NPC470097
0.8889	High Similarity	NPC114119
0.8889	High Similarity	NPC471415
0.8881	High Similarity	NPC140502
0.8881	High Similarity	NPC60249
0.8873	High Similarity	NPC226547
0.8873	High Similarity	NPC56091
0.8873	High Similarity	NPC46591
0.8857	High Similarity	NPC141765
0.8857	High Similarity	NPC236522
0.8857	High Similarity	NPC99572
0.8857	High Similarity	NPC24490
0.8857	High Similarity	NPC150534

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 NPC84181 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	743
0.2-0.3	1756
0.3-0.4	2815
0.4-0.5	1880
0.5-0.6	1102
0.6-0.7	461
0.7-0.8	67
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8429	Intermediate Similarity	NPD3027	Phase 3
0.8428	Intermediate Similarity	NPD7228	Approved
0.8414	Intermediate Similarity	NPD7266	Discontinued
0.8333	Intermediate Similarity	NPD6234	Discontinued
0.8205	Intermediate Similarity	NPD4966	Approved
0.8205	Intermediate Similarity	NPD4967	Phase 2
0.8205	Intermediate Similarity	NPD4965	Approved
0.8176	Intermediate Similarity	NPD6674	Discontinued
0.8125	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1613	Approved
0.8116	Intermediate Similarity	NPD3705	Approved
0.8013	Intermediate Similarity	NPD37	Approved
0.7899	Intermediate Similarity	NPD1357	Approved
0.7892	Intermediate Similarity	NPD7240	Approved
0.7892	Intermediate Similarity	NPD7685	Pre-registration
0.7871	Intermediate Similarity	NPD1653	Approved
0.7847	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5058	Phase 3
0.7778	Intermediate Similarity	NPD7199	Phase 2
0.7778	Intermediate Similarity	NPD2861	Phase 2
0.7778	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7074	Phase 3
0.7758	Intermediate Similarity	NPD3818	Discontinued
0.7755	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD3620	Phase 2
0.773	Intermediate Similarity	NPD1091	Approved
0.7721	Intermediate Similarity	NPD5283	Phase 1
0.7711	Intermediate Similarity	NPD7054	Approved
0.7665	Intermediate Similarity	NPD7472	Approved
0.7625	Intermediate Similarity	NPD2978	Approved
0.7625	Intermediate Similarity	NPD2977	Approved
0.7576	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD228	Approved
0.7528	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7471	Intermediate Similarity	NPD7251	Discontinued
0.7465	Intermediate Similarity	NPD5125	Phase 3
0.7465	Intermediate Similarity	NPD5126	Approved
0.7459	Intermediate Similarity	NPD7680	Approved
0.7442	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7808	Phase 3
0.7426	Intermediate Similarity	NPD3022	Approved
0.7426	Intermediate Similarity	NPD3021	Approved
0.7412	Intermediate Similarity	NPD6797	Phase 2
0.7407	Intermediate Similarity	NPD8455	Phase 2
0.7383	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1610	Phase 2
0.7357	Intermediate Similarity	NPD7157	Approved
0.7355	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5735	Approved
0.7346	Intermediate Similarity	NPD1934	Approved
0.7338	Intermediate Similarity	NPD1375	Discontinued
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5588	Approved
0.732	Intermediate Similarity	NPD4108	Discontinued
0.7285	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6559	Discontinued
0.7267	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD7843	Approved
0.7261	Intermediate Similarity	NPD6190	Approved
0.726	Intermediate Similarity	NPD2983	Phase 2
0.726	Intermediate Similarity	NPD2982	Phase 2
0.7255	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7097	Phase 1
0.7255	Intermediate Similarity	NPD4536	Approved
0.7255	Intermediate Similarity	NPD4538	Approved
0.725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4237	Approved
0.7244	Intermediate Similarity	NPD4236	Phase 3
0.7226	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7028	Phase 2
0.7219	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6166	Phase 2
0.7219	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7095	Approved
0.7195	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2981	Phase 2
0.7181	Intermediate Similarity	NPD3018	Phase 2
0.7171	Intermediate Similarity	NPD1558	Phase 1
0.7152	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4749	Approved
0.7134	Intermediate Similarity	NPD3060	Approved
0.7134	Intermediate Similarity	NPD5177	Phase 3
0.7124	Intermediate Similarity	NPD6355	Discontinued
0.7115	Intermediate Similarity	NPD5762	Approved
0.7115	Intermediate Similarity	NPD5763	Approved
0.7113	Intermediate Similarity	NPD6671	Approved
0.7107	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2684	Approved
0.7097	Intermediate Similarity	NPD5960	Phase 3
0.7095	Intermediate Similarity	NPD8651	Approved
0.7093	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6331	Phase 2
0.7089	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4110	Phase 3
0.7086	Intermediate Similarity	NPD7312	Approved
0.7086	Intermediate Similarity	NPD7313	Approved
0.7086	Intermediate Similarity	NPD4625	Phase 3
0.7086	Intermediate Similarity	NPD7311	Approved
0.7086	Intermediate Similarity	NPD7310	Approved
0.7078	Intermediate Similarity	NPD6653	Approved
0.7059	Intermediate Similarity	NPD2238	Phase 2
0.7048	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3094	Phase 2
0.7045	Intermediate Similarity	NPD7309	Approved
0.7041	Intermediate Similarity	NPD8127	Discontinued
0.703	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7906	Approved
0.7018	Intermediate Similarity	NPD2489	Approved
0.7018	Intermediate Similarity	NPD27	Approved
0.7006	Intermediate Similarity	NPD3882	Suspended
0.6989	Remote Similarity	NPD8313	Approved
0.6989	Remote Similarity	NPD8312	Approved
0.6988	Remote Similarity	NPD5773	Approved
0.6988	Remote Similarity	NPD5772	Approved
0.6988	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2801	Approved
0.6983	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4628	Phase 3
0.6968	Remote Similarity	NPD6353	Approved
0.6966	Remote Similarity	NPD4663	Approved
0.6966	Remote Similarity	NPD1548	Phase 1
0.6964	Remote Similarity	NPD5604	Discontinued
0.6959	Remote Similarity	NPD2970	Approved
0.6959	Remote Similarity	NPD2969	Approved
0.6951	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4140	Approved
0.6943	Remote Similarity	NPD2161	Phase 2
0.6937	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5327	Phase 3
0.6909	Remote Similarity	NPD4380	Phase 2
0.6906	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7296	Approved
0.6903	Remote Similarity	NPD3657	Discovery
0.6901	Remote Similarity	NPD3787	Discontinued
0.6901	Remote Similarity	NPD6071	Discontinued
0.6901	Remote Similarity	NPD3051	Approved
0.6897	Remote Similarity	NPD5844	Phase 1
0.6897	Remote Similarity	NPD5536	Phase 2
0.6893	Remote Similarity	NPD4578	Approved
0.6893	Remote Similarity	NPD4577	Approved
0.6892	Remote Similarity	NPD3092	Approved
0.689	Remote Similarity	NPD4210	Discontinued
0.6887	Remote Similarity	NPD6584	Phase 3
0.6887	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5582	Discontinued
0.6883	Remote Similarity	NPD6233	Phase 2
0.6882	Remote Similarity	NPD5494	Approved
0.6879	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD7473	Discontinued
0.6879	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7526	Approved
0.6871	Remote Similarity	NPD52	Approved
0.6871	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6516	Phase 2
0.6871	Remote Similarity	NPD5846	Approved
0.6867	Remote Similarity	NPD6696	Suspended
0.6848	Remote Similarity	NPD4005	Discontinued
0.6845	Remote Similarity	NPD2563	Approved
0.6845	Remote Similarity	NPD3817	Phase 2
0.6845	Remote Similarity	NPD2560	Approved
0.6833	Remote Similarity	NPD6843	Phase 3
0.6833	Remote Similarity	NPD6842	Approved
0.6833	Remote Similarity	NPD6841	Approved
0.6832	Remote Similarity	NPD5241	Discontinued
0.6832	Remote Similarity	NPD2677	Approved
0.6826	Remote Similarity	NPD3383	Approved
0.6826	Remote Similarity	NPD3382	Approved
0.6826	Remote Similarity	NPD3384	Approved
0.6818	Remote Similarity	NPD6798	Discontinued
0.6818	Remote Similarity	NPD5110	Phase 2
0.6818	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5109	Approved
0.6818	Remote Similarity	NPD5111	Phase 2
0.6813	Remote Similarity	NPD4162	Approved
0.681	Remote Similarity	NPD4123	Phase 3
0.6802	Remote Similarity	NPD6232	Discontinued
0.68	Remote Similarity	NPD3685	Discontinued
0.6797	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5124	Phase 1
0.6792	Remote Similarity	NPD6004	Phase 3
0.6792	Remote Similarity	NPD6005	Phase 3
0.6792	Remote Similarity	NPD6002	Phase 3
0.6792	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7124	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