NPASS Compound

Structure

NPC114119 OpenBabel07101719142D 42 46 0 0 1 0 0 0 0 0999 V2000 -10.1859 2.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8558 2.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3199 -0.9351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2577 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1859 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1237 -0.9351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4539 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1237 1.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7218 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 2.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4539 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2577 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1859 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9898 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3199 1.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9898 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7218 -0.4351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5878 -0.9351 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3917 1.0649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5878 1.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0519 1.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5878 -1.9351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3199 2.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8558 1.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 3.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 2.0594 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 -5.8558 -0.9351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 36 1 0 0 0 0 2 37 1 0 0 0 0 3 38 1 0 0 0 0 4 39 1 0 0 0 0 5 7 2 0 0 0 0 5 16 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 16 2 0 0 0 0 9 23 1 0 0 0 0 10 17 2 0 0 0 0 10 24 1 0 0 0 0 11 18 2 0 0 0 0 11 25 1 0 0 0 0 12 18 1 0 0 0 0 12 26 2 0 0 0 0 13 32 1 0 0 0 0 14 41 1 0 0 0 0 15 40 1 0 0 0 0 16 28 1 0 0 0 0 19 14 1 1 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 15 1 1 0 0 0 20 31 1 0 0 0 0 21 23 2 0 0 0 0 21 33 1 0 0 0 0 22 24 2 0 0 0 0 22 42 1 0 0 0 0 23 36 1 0 0 0 0 24 37 1 0 0 0 0 25 29 2 0 0 0 0 25 38 1 0 0 0 0 26 29 1 0 0 0 0 26 39 1 0 0 0 0 27 13 1 6 0 0 0 27 28 1 0 0 0 0 27 42 1 0 0 0 0 28 34 1 6 0 0 0 29 35 1 0 0 0 0 30 17 1 6 0 0 0 30 40 1 0 0 0 0 31 18 1 6 0 0 0 31 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.23
Volume:	574.914
LogP:	1.952
LogD:	2.344
LogS:	-4.457
# Rotatable Bonds:	11
TPSA:	145.53
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.262
Synthetic Accessibility Score:	4.362
Fsp3:	0.419
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:	-5.661
MDCK Permeability:	2.242881055281032e-05
Pgp-inhibitor:	0.725
Pgp-substrate:	0.622
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	75.5647201538086%
Volume Distribution (VD):	0.504
Pgp-substrate:	18.535415649414062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.538
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.773
CYP2C9-inhibitor:	0.345
CYP2C9-substrate:	0.774
CYP2D6-inhibitor:	0.106
CYP2D6-substrate:	0.493
CYP3A4-inhibitor:	0.494
CYP3A4-substrate:	0.77

ADMET: Excretion

Clearance (CL):	6.082
Half-life (T1/2):	0.645

ADMET: Toxicity

hERG Blockers:	0.349
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.672
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.17
Skin Sensitization:	0.878
Carcinogencity:	0.09
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.051

Download Data

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

Natural Product: NPC114119

Natural Product ID:	NPC114119
*Common Name:**	Ficusesquilignan A
IUPAC Name:	(1R,2S)-2-[4-[(3R,3aS,6R,6aS)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenoxy]-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol
Synonyms:	Ficusesquilignan A
Standard InCHIKey:	PFZFCRCFYYFTPE-RWMYVIIASA-N
Standard InCHI:	InChI=1S/C31H36O11/c1-36-23-9-16(5-7-21(23)33)28(34)27(13-32)42-22-8-6-17(10-24(22)37-2)30-19-14-41-31(20(19)15-40-30)18-11-25(38-3)29(35)26(12-18)39-4/h5-12,19-20,27-28,30-35H,13-15H2,1-4H3/t19-,20-,27+,28-,30+,31+/m1/s1
SMILES:	COc1cc(ccc1O)[C@H]([C@H](CO)Oc1ccc(cc1OC)[C@H]1[C@@H]2CO[C@@H](c3cc(c(c(c3)OC)O)OC)[C@@H]2CO1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1760589
PubChem CID:	54580061
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19813743]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	trunk	Jeju island, Korea	2005-Dec	PMID[21420296]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21420296]
NPO4001	Berberis koreana	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	>	500000.0	nM	PMID[490713]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[490713]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	11520.0	nM	PMID[490713]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	9470.0	nM	PMID[490713]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[490713]

☑ 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 NPC114119 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	457
0.1-0.2	1354
0.2-0.3	3934
0.3-0.4	10775
0.4-0.5	8208
0.5-0.6	4854
0.6-0.7	7911
0.7-0.8	3825
0.8-0.85	890
0.85-0.9	420
0.9-0.95	54
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471415
1.0	High Similarity	NPC470097
0.9855	High Similarity	NPC324492
0.9855	High Similarity	NPC317053
0.9784	High Similarity	NPC320671
0.9784	High Similarity	NPC327412
0.9784	High Similarity	NPC328567
0.9784	High Similarity	NPC320970
0.9706	High Similarity	NPC291101
0.9706	High Similarity	NPC266197
0.9645	High Similarity	NPC473266
0.9645	High Similarity	NPC470098
0.9645	High Similarity	NPC470826
0.9571	High Similarity	NPC260397
0.951	High Similarity	NPC324517
0.951	High Similarity	NPC321972
0.951	High Similarity	NPC329343
0.9489	High Similarity	NPC22517
0.9485	High Similarity	NPC77861
0.942	High Similarity	NPC55793
0.9412	High Similarity	NPC141765
0.9412	High Similarity	NPC99572
0.9412	High Similarity	NPC165155
0.9412	High Similarity	NPC24490
0.9412	High Similarity	NPC126409
0.9412	High Similarity	NPC34103
0.9371	High Similarity	NPC51328
0.9371	High Similarity	NPC286235
0.9371	High Similarity	NPC55158
0.9362	High Similarity	NPC181615
0.9338	High Similarity	NPC244983
0.9338	High Similarity	NPC287745
0.9338	High Similarity	NPC326095
0.9301	High Similarity	NPC248132
0.9301	High Similarity	NPC130449
0.9281	High Similarity	NPC184797
0.9281	High Similarity	NPC309124
0.927	High Similarity	NPC93783
0.9265	High Similarity	NPC158331
0.9231	High Similarity	NPC39657
0.9214	High Similarity	NPC263261
0.9214	High Similarity	NPC311530
0.9214	High Similarity	NPC178054
0.9214	High Similarity	NPC470372
0.9214	High Similarity	NPC87725
0.9209	High Similarity	NPC236306
0.9209	High Similarity	NPC473739
0.9209	High Similarity	NPC232164
0.9197	High Similarity	NPC170694
0.9191	High Similarity	NPC470752
0.9191	High Similarity	NPC160991
0.9191	High Similarity	NPC184447
0.9191	High Similarity	NPC16208
0.9191	High Similarity	NPC7903
0.9191	High Similarity	NPC175067
0.9191	High Similarity	NPC204215
0.9191	High Similarity	NPC35932
0.9149	High Similarity	NPC302506
0.9149	High Similarity	NPC107161
0.9143	High Similarity	NPC254759
0.9143	High Similarity	NPC160283
0.9137	High Similarity	NPC474390
0.9118	High Similarity	NPC158079
0.9118	High Similarity	NPC470095
0.9118	High Similarity	NPC469625
0.9118	High Similarity	NPC309787
0.9118	High Similarity	NPC7171
0.9118	High Similarity	NPC40432
0.9118	High Similarity	NPC470096
0.9118	High Similarity	NPC472597
0.9118	High Similarity	NPC469613
0.9118	High Similarity	NPC161557
0.9118	High Similarity	NPC228346
0.9118	High Similarity	NPC30043
0.9118	High Similarity	NPC474017
0.9118	High Similarity	NPC115207
0.9118	High Similarity	NPC27843
0.9116	High Similarity	NPC470769
0.9091	High Similarity	NPC279298
0.9091	High Similarity	NPC22150
0.9091	High Similarity	NPC38041
0.9085	High Similarity	NPC477616
0.9078	High Similarity	NPC471389
0.9078	High Similarity	NPC247291
0.9071	High Similarity	NPC292882
0.9071	High Similarity	NPC260842
0.9065	High Similarity	NPC265433
0.9065	High Similarity	NPC306441
0.9065	High Similarity	NPC16435
0.9065	High Similarity	NPC270456
0.9065	High Similarity	NPC162659
0.9065	High Similarity	NPC248727
0.9058	High Similarity	NPC310854
0.9054	High Similarity	NPC157333
0.9051	High Similarity	NPC201587
0.9051	High Similarity	NPC181049
0.9051	High Similarity	NPC253105
0.9051	High Similarity	NPC207400
0.9051	High Similarity	NPC4940
0.9044	High Similarity	NPC174495
0.9044	High Similarity	NPC242807
0.9044	High Similarity	NPC469612
0.9044	High Similarity	NPC153739
0.9044	High Similarity	NPC469614
0.9044	High Similarity	NPC145305
0.9044	High Similarity	NPC241522
0.9044	High Similarity	NPC472338
0.9044	High Similarity	NPC42300
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	NPC477612
0.9034	High Similarity	NPC102934
0.9034	High Similarity	NPC226153
0.9034	High Similarity	NPC304048
0.9034	High Similarity	NPC252402
0.9034	High Similarity	NPC20757
0.9034	High Similarity	NPC329836
0.9034	High Similarity	NPC227516
0.9028	High Similarity	NPC112861
0.9021	High Similarity	NPC187774
0.9021	High Similarity	NPC280092
0.9021	High Similarity	NPC472712
0.9021	High Similarity	NPC472713
0.9021	High Similarity	NPC45257
0.9021	High Similarity	NPC473046
0.9021	High Similarity	NPC63879
0.9021	High Similarity	NPC179521
0.9021	High Similarity	NPC15659
0.9021	High Similarity	NPC12641
0.9021	High Similarity	NPC118385
0.9021	High Similarity	NPC304894
0.9021	High Similarity	NPC93323
0.9014	High Similarity	NPC476356
0.9007	High Similarity	NPC27495
0.9007	High Similarity	NPC177868
0.9007	High Similarity	NPC262189
0.9007	High Similarity	NPC22317
0.9	High Similarity	NPC477938
0.8993	High Similarity	NPC94750
0.8993	High Similarity	NPC121812
0.8993	High Similarity	NPC112939
0.8993	High Similarity	NPC474206
0.8993	High Similarity	NPC61946
0.8993	High Similarity	NPC260898
0.8993	High Similarity	NPC112246
0.8993	High Similarity	NPC47398
0.8993	High Similarity	NPC234333
0.8993	High Similarity	NPC470356
0.8986	High Similarity	NPC475840
0.8978	High Similarity	NPC277804
0.8973	High Similarity	NPC211561
0.8971	High Similarity	NPC285339
0.8971	High Similarity	NPC190629
0.8971	High Similarity	NPC273295
0.8971	High Similarity	NPC3439
0.8971	High Similarity	NPC210623
0.8971	High Similarity	NPC218856
0.8971	High Similarity	NPC226788
0.8971	High Similarity	NPC202582
0.8971	High Similarity	NPC476968
0.8971	High Similarity	NPC475875
0.8971	High Similarity	NPC470258
0.8971	High Similarity	NPC170844
0.8971	High Similarity	NPC222004
0.8958	High Similarity	NPC18979
0.8951	High Similarity	NPC102044
0.8951	High Similarity	NPC255566
0.8951	High Similarity	NPC298317
0.8951	High Similarity	NPC185071
0.8951	High Similarity	NPC477898
0.8951	High Similarity	NPC470950
0.8951	High Similarity	NPC12728
0.8951	High Similarity	NPC47633
0.8951	High Similarity	NPC163508
0.8951	High Similarity	NPC173203
0.8951	High Similarity	NPC469630
0.8951	High Similarity	NPC185307
0.8951	High Similarity	NPC85264
0.8936	High Similarity	NPC25966
0.8936	High Similarity	NPC260741
0.8936	High Similarity	NPC245207
0.8936	High Similarity	NPC471388
0.8936	High Similarity	NPC127218
0.8936	High Similarity	NPC70682
0.8936	High Similarity	NPC319647
0.8929	High Similarity	NPC302701
0.8929	High Similarity	NPC29799
0.8929	High Similarity	NPC474639
0.8929	High Similarity	NPC477939
0.8929	High Similarity	NPC209985
0.8929	High Similarity	NPC230734
0.8929	High Similarity	NPC177160
0.8929	High Similarity	NPC54743
0.8929	High Similarity	NPC472336
0.8929	High Similarity	NPC156502
0.8929	High Similarity	NPC263367
0.8929	High Similarity	NPC269091

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 NPC114119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	802
0.2-0.3	1840
0.3-0.4	2797
0.4-0.5	1731
0.5-0.6	1008
0.6-0.7	514
0.7-0.8	101
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8971	High Similarity	NPD3027	Phase 3
0.8777	High Similarity	NPD1613	Approved
0.8777	High Similarity	NPD1612	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD4908	Phase 1
0.8333	Intermediate Similarity	NPD6234	Discontinued
0.8239	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD4966	Approved
0.8205	Intermediate Similarity	NPD4967	Phase 2
0.8205	Intermediate Similarity	NPD4965	Approved
0.8199	Intermediate Similarity	NPD7228	Approved
0.8113	Intermediate Similarity	NPD7199	Phase 2
0.8013	Intermediate Similarity	NPD37	Approved
0.7986	Intermediate Similarity	NPD1610	Phase 2
0.7963	Intermediate Similarity	NPD6166	Phase 2
0.7963	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD2861	Phase 2
0.7901	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1934	Approved
0.7877	Intermediate Similarity	NPD3620	Phase 2
0.7877	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD3818	Discontinued
0.7756	Intermediate Similarity	NPD1653	Approved
0.7746	Intermediate Similarity	NPD2983	Phase 2
0.7746	Intermediate Similarity	NPD2982	Phase 2
0.774	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD5283	Phase 1
0.7703	Intermediate Similarity	NPD5735	Approved
0.7698	Intermediate Similarity	NPD1548	Phase 1
0.7697	Intermediate Similarity	NPD6674	Discontinued
0.7688	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7240	Approved
0.7676	Intermediate Similarity	NPD2981	Phase 2
0.7665	Intermediate Similarity	NPD7074	Phase 3
0.7655	Intermediate Similarity	NPD3018	Phase 2
0.764	Intermediate Similarity	NPD3882	Suspended
0.7625	Intermediate Similarity	NPD2801	Approved
0.7622	Intermediate Similarity	NPD4749	Approved
0.7609	Intermediate Similarity	NPD7157	Approved
0.7605	Intermediate Similarity	NPD7054	Approved
0.7595	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD228	Approved
0.7566	Intermediate Similarity	NPD7266	Discontinued
0.756	Intermediate Similarity	NPD7472	Approved
0.7551	Intermediate Similarity	NPD4625	Phase 3
0.7518	Intermediate Similarity	NPD7843	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5844	Phase 1
0.7483	Intermediate Similarity	NPD3705	Approved
0.7468	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD5588	Approved
0.7426	Intermediate Similarity	NPD3022	Approved
0.7426	Intermediate Similarity	NPD3021	Approved
0.7412	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4060	Phase 1
0.74	Intermediate Similarity	NPD1558	Phase 1
0.7399	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5494	Approved
0.7389	Intermediate Similarity	NPD1511	Approved
0.7381	Intermediate Similarity	NPD7473	Discontinued
0.7379	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4538	Approved
0.7368	Intermediate Similarity	NPD7251	Discontinued
0.7368	Intermediate Similarity	NPD4536	Approved
0.7363	Intermediate Similarity	NPD7680	Approved
0.7362	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3817	Phase 2
0.7358	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2684	Approved
0.7347	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6584	Phase 3
0.7343	Intermediate Similarity	NPD6516	Phase 2
0.7343	Intermediate Similarity	NPD5846	Approved
0.7342	Intermediate Similarity	NPD7447	Phase 1
0.7333	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD8651	Approved
0.7329	Intermediate Similarity	NPD4675	Approved
0.7329	Intermediate Similarity	NPD4678	Approved
0.7326	Intermediate Similarity	NPD7808	Phase 3
0.7325	Intermediate Similarity	NPD5058	Phase 3
0.7315	Intermediate Similarity	NPD7095	Approved
0.731	Intermediate Similarity	NPD6797	Phase 2
0.7308	Intermediate Similarity	NPD6331	Phase 2
0.7308	Intermediate Similarity	NPD7466	Approved
0.7305	Intermediate Similarity	NPD6232	Discontinued
0.7296	Intermediate Similarity	NPD1512	Approved
0.7278	Intermediate Similarity	NPD7213	Phase 3
0.7278	Intermediate Similarity	NPD7212	Phase 2
0.7273	Intermediate Similarity	NPD1357	Approved
0.7267	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4005	Discontinued
0.7267	Intermediate Similarity	NPD6559	Discontinued
0.7261	Intermediate Similarity	NPD6190	Approved
0.726	Intermediate Similarity	NPD5327	Phase 3
0.7246	Intermediate Similarity	NPD8127	Discontinued
0.7244	Intermediate Similarity	NPD4237	Approved
0.7244	Intermediate Similarity	NPD4236	Phase 3
0.7241	Intermediate Similarity	NPD1091	Approved
0.7241	Intermediate Similarity	NPD8054	Approved
0.7241	Intermediate Similarity	NPD8053	Approved
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5762	Approved
0.7226	Intermediate Similarity	NPD5763	Approved
0.7225	Intermediate Similarity	NPD7549	Discontinued
0.7225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4380	Phase 2
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7216	Intermediate Similarity	NPD7906	Approved
0.7215	Intermediate Similarity	NPD7124	Phase 2
0.7208	Intermediate Similarity	NPD5960	Phase 3
0.7202	Intermediate Similarity	NPD7229	Phase 3
0.7197	Intermediate Similarity	NPD3892	Phase 2
0.7197	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4110	Phase 3
0.7195	Intermediate Similarity	NPD1465	Phase 2
0.719	Intermediate Similarity	NPD6653	Approved
0.719	Intermediate Similarity	NPD6353	Approved
0.7171	Intermediate Similarity	NPD4140	Approved
0.7171	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7075	Discontinued
0.7162	Intermediate Similarity	NPD3094	Phase 2
0.7161	Intermediate Similarity	NPD6099	Approved
0.7161	Intermediate Similarity	NPD2161	Phase 2
0.7161	Intermediate Similarity	NPD6100	Approved
0.7159	Intermediate Similarity	NPD4663	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD6582	Phase 2
0.7134	Intermediate Similarity	NPD3060	Approved
0.7134	Intermediate Similarity	NPD5177	Phase 3
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7124	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5124	Phase 1
0.7118	Intermediate Similarity	NPD2489	Approved
0.7118	Intermediate Similarity	NPD27	Approved
0.7115	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1375	Discontinued
0.7115	Intermediate Similarity	NPD3540	Phase 1
0.7113	Intermediate Similarity	NPD6671	Approved
0.7101	Intermediate Similarity	NPD3051	Approved
0.7091	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2977	Approved
0.7091	Intermediate Similarity	NPD5772	Approved
0.7091	Intermediate Similarity	NPD2978	Approved
0.7091	Intermediate Similarity	NPD5773	Approved
0.7091	Intermediate Similarity	NPD8455	Phase 2
0.7089	Intermediate Similarity	NPD4628	Phase 3
0.7086	Intermediate Similarity	NPD7312	Approved
0.7086	Intermediate Similarity	NPD7311	Approved
0.7086	Intermediate Similarity	NPD7313	Approved
0.7086	Intermediate Similarity	NPD4578	Approved
0.7086	Intermediate Similarity	NPD4577	Approved
0.7086	Intermediate Similarity	NPD7310	Approved
0.7081	Intermediate Similarity	NPD52	Approved
0.7081	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7526	Approved
0.707	Intermediate Similarity	NPD7037	Approved
0.7069	Intermediate Similarity	NPD7685	Pre-registration
0.7063	Intermediate Similarity	NPD4357	Discontinued
0.7059	Intermediate Similarity	NPD2969	Approved
0.7059	Intermediate Similarity	NPD2970	Approved
0.7059	Intermediate Similarity	NPD2238	Phase 2
0.7055	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3539	Phase 1
0.7048	Intermediate Similarity	NPD2563	Approved
0.7048	Intermediate Similarity	NPD2560	Approved
0.7045	Intermediate Similarity	NPD7309	Approved
0.7044	Intermediate Similarity	NPD2677	Approved
0.7041	Intermediate Similarity	NPD6959	Discontinued
0.7032	Intermediate Similarity	NPD7097	Phase 1
0.7032	Intermediate Similarity	NPD6111	Discontinued
0.7029	Intermediate Similarity	NPD290	Approved
0.7027	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4162	Approved
0.702	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4123	Phase 3
0.7019	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3657	Discovery
0.7007	Intermediate Similarity	NPD3092	Approved
0.7007	Intermediate Similarity	NPD422	Phase 1
0.7006	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7768	Phase 2
0.7006	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6071	Discontinued
0.6994	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7819	Suspended
0.6988	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6658	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