NPASS Compound

Structure

NPC25695 OpenBabel07101718292D 29 31 0 0 1 0 0 0 0 0999 V2000 10.4773 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 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 4.4152 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8793 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 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 5.2812 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 7 14 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 17 2 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 27 1 0 0 0 0 12 28 1 0 0 0 0 13 2 1 6 0 0 0 13 20 1 0 0 0 0 13 29 1 0 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 22 1 0 0 0 0 17 25 1 0 0 0 0 18 21 2 0 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 19 27 1 0 0 0 0 20 23 1 1 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.17
Volume:	406.475
LogP:	3.469
LogD:	3.374
LogS:	-4.7
# Rotatable Bonds:	9
TPSA:	75.61
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.642
Synthetic Accessibility Score:	3.404
Fsp3:	0.364
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:	-4.632
MDCK Permeability:	2.0305640646256506e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	91.3045883178711%
Volume Distribution (VD):	1.053
Pgp-substrate:	9.045122146606445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.663
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.876
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.75
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.952
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.966
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	9.274
Half-life (T1/2):	0.455

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.266
Skin Sensitization:	0.834
Carcinogencity:	0.719
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC25695

Natural Product ID:	NPC25695
*Common Name:**	(-)-(7R,8R)-4,5-Methylenedioxy-3,3',5'-Trimethoxy-7-Hydroxy-1'-Allyl-8-O-4'-Neolignan
IUPAC Name:	(1R,2R)-2-(2,6-dimethoxy-4-prop-2-enylphenoxy)-1-(7-methoxy-1,3-benzodioxol-5-yl)propan-1-ol
Synonyms:
Standard InCHIKey:	BKBJBGBNWACESC-XCLFUZPHSA-N
Standard InCHI:	InChI=1S/C22H26O7/c1-6-7-14-8-16(24-3)22(17(9-14)25-4)29-13(2)20(23)15-10-18(26-5)21-19(11-15)27-12-28-21/h6,8-11,13,20,23H,1,7,12H2,2-5H3/t13-,20+/m1/s1
SMILES:	C=CCc1cc(OC)c(c(c1)OC)O[C@@H]([C@@H](c1cc(OC)c2c(c1)OCO2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105534
PubChem CID:	76324797
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	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
EC50	1
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio CC50/EC50	=	4.0	n.a.	PMID[522971]
NPT27	Others	Unspecified		CC50	=	50600.0	nM	PMID[522971]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	12800.0	nM	PMID[522971]

☑ 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 NPC25695 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	368
0.1-0.2	1492
0.2-0.3	4455
0.3-0.4	11207
0.4-0.5	7193
0.5-0.6	4633
0.6-0.7	7077
0.7-0.8	4628
0.8-0.85	978
0.85-0.9	546
0.9-0.95	105
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC172818
0.9457	High Similarity	NPC3439
0.9457	High Similarity	NPC470258
0.9457	High Similarity	NPC285339
0.9457	High Similarity	NPC273295
0.9457	High Similarity	NPC218856
0.9457	High Similarity	NPC202582
0.9457	High Similarity	NPC190629
0.9457	High Similarity	NPC222004
0.9457	High Similarity	NPC226788
0.9457	High Similarity	NPC210623
0.9394	High Similarity	NPC48863
0.9394	High Similarity	NPC251981
0.9394	High Similarity	NPC13745
0.9338	High Similarity	NPC189115
0.9338	High Similarity	NPC469559
0.9328	High Similarity	NPC474039
0.9318	High Similarity	NPC196937
0.9318	High Similarity	NPC58585
0.9318	High Similarity	NPC49074
0.9318	High Similarity	NPC69513
0.9318	High Similarity	NPC215833
0.9313	High Similarity	NPC469613
0.9313	High Similarity	NPC469625
0.9313	High Similarity	NPC472597
0.9313	High Similarity	NPC30043
0.9302	High Similarity	NPC474119
0.9281	High Similarity	NPC39657
0.927	High Similarity	NPC81638
0.9265	High Similarity	NPC469661
0.9259	High Similarity	NPC98777
0.9259	High Similarity	NPC212770
0.9259	High Similarity	NPC292487
0.9242	High Similarity	NPC184447
0.9242	High Similarity	NPC16208
0.9242	High Similarity	NPC35932
0.9242	High Similarity	NPC162093
0.9242	High Similarity	NPC7903
0.9242	High Similarity	NPC299144
0.9242	High Similarity	NPC160991
0.9237	High Similarity	NPC63574
0.9237	High Similarity	NPC469614
0.9237	High Similarity	NPC472338
0.9237	High Similarity	NPC469612
0.9225	High Similarity	NPC473960
0.9203	High Similarity	NPC473045
0.9203	High Similarity	NPC25292
0.9197	High Similarity	NPC475084
0.9191	High Similarity	NPC177868
0.9191	High Similarity	NPC226547
0.9185	High Similarity	NPC185908
0.9185	High Similarity	NPC65530
0.9185	High Similarity	NPC59324
0.9173	High Similarity	NPC471391
0.9173	High Similarity	NPC112237
0.9173	High Similarity	NPC25821
0.9173	High Similarity	NPC471390
0.916	High Similarity	NPC270849
0.916	High Similarity	NPC228769
0.916	High Similarity	NPC470633
0.916	High Similarity	NPC26653
0.9149	High Similarity	NPC55158
0.9149	High Similarity	NPC286235
0.9149	High Similarity	NPC51328
0.9137	High Similarity	NPC180953
0.9137	High Similarity	NPC475096
0.913	High Similarity	NPC298317
0.913	High Similarity	NPC255566
0.913	High Similarity	NPC473044
0.9111	High Similarity	NPC164857
0.9111	High Similarity	NPC242028
0.9111	High Similarity	NPC471719
0.9111	High Similarity	NPC203230
0.9104	High Similarity	NPC107478
0.9104	High Similarity	NPC310854
0.9104	High Similarity	NPC287745
0.9104	High Similarity	NPC187194
0.9104	High Similarity	NPC170694
0.9098	High Similarity	NPC470752
0.9091	High Similarity	NPC472024
0.9091	High Similarity	NPC80600
0.9078	High Similarity	NPC270751
0.9078	High Similarity	NPC248132
0.9078	High Similarity	NPC130449
0.9071	High Similarity	NPC125755
0.9071	High Similarity	NPC190714
0.9071	High Similarity	NPC162193
0.9071	High Similarity	NPC99515
0.907	High Similarity	NPC109822
0.907	High Similarity	NPC94276
0.9065	High Similarity	NPC187774
0.9065	High Similarity	NPC472713
0.9065	High Similarity	NPC473046
0.9065	High Similarity	NPC118385
0.9065	High Similarity	NPC472712
0.9058	High Similarity	NPC41782
0.9051	High Similarity	NPC46591
0.9044	High Similarity	NPC470413
0.9044	High Similarity	NPC283949
0.9044	High Similarity	NPC195196
0.9044	High Similarity	NPC138738
0.9044	High Similarity	NPC477938
0.9037	High Similarity	NPC472337
0.9037	High Similarity	NPC236522
0.9037	High Similarity	NPC101624
0.9037	High Similarity	NPC61946
0.9037	High Similarity	NPC150534
0.9037	High Similarity	NPC470236
0.9037	High Similarity	NPC184938
0.903	High Similarity	NPC132895
0.903	High Similarity	NPC263064
0.903	High Similarity	NPC115022
0.903	High Similarity	NPC294166
0.903	High Similarity	NPC266848
0.903	High Similarity	NPC475840
0.903	High Similarity	NPC158331
0.903	High Similarity	NPC136750
0.9023	High Similarity	NPC309787
0.9023	High Similarity	NPC121376
0.9023	High Similarity	NPC470096
0.9023	High Similarity	NPC470095
0.9015	High Similarity	NPC166040
0.9015	High Similarity	NPC170844
0.9015	High Similarity	NPC476968
0.9015	High Similarity	NPC248355
0.9008	High Similarity	NPC163332
0.9008	High Similarity	NPC147821
0.9008	High Similarity	NPC41706
0.9008	High Similarity	NPC292056
0.9008	High Similarity	NPC111247
0.9008	High Similarity	NPC210355
0.9008	High Similarity	NPC183181
0.9008	High Similarity	NPC319625
0.9008	High Similarity	NPC118787
0.9007	High Similarity	NPC227902
0.9	High Similarity	NPC307466
0.9	High Similarity	NPC277867
0.9	High Similarity	NPC161700
0.8993	High Similarity	NPC185307
0.8993	High Similarity	NPC470950
0.8993	High Similarity	NPC185071
0.8993	High Similarity	NPC46092
0.8993	High Similarity	NPC474808
0.8993	High Similarity	NPC12728
0.8993	High Similarity	NPC252169
0.8986	High Similarity	NPC263261
0.8986	High Similarity	NPC87725
0.8971	High Similarity	NPC104167
0.8971	High Similarity	NPC472336
0.8971	High Similarity	NPC16435
0.8971	High Similarity	NPC472334
0.8971	High Similarity	NPC306441
0.8963	High Similarity	NPC470881
0.8963	High Similarity	NPC309744
0.8963	High Similarity	NPC244983
0.8963	High Similarity	NPC476411
0.8963	High Similarity	NPC326095
0.8955	High Similarity	NPC261812
0.8955	High Similarity	NPC165686
0.8955	High Similarity	NPC175067
0.8955	High Similarity	NPC471505
0.8955	High Similarity	NPC201587
0.8955	High Similarity	NPC253105
0.8955	High Similarity	NPC72046
0.8955	High Similarity	NPC470270
0.8955	High Similarity	NPC65183
0.8955	High Similarity	NPC106739
0.8955	High Similarity	NPC219671
0.8955	High Similarity	NPC85799
0.8955	High Similarity	NPC26080
0.8955	High Similarity	NPC303422
0.8955	High Similarity	NPC259742
0.8955	High Similarity	NPC204215
0.8955	High Similarity	NPC147616
0.8955	High Similarity	NPC104077
0.8951	High Similarity	NPC472710
0.8951	High Similarity	NPC472709
0.8947	High Similarity	NPC184814
0.8944	High Similarity	NPC301961
0.8944	High Similarity	NPC175976
0.8944	High Similarity	NPC166584
0.8939	High Similarity	NPC470084
0.8939	High Similarity	NPC98631
0.8939	High Similarity	NPC206615
0.8939	High Similarity	NPC302378
0.8939	High Similarity	NPC186843
0.8939	High Similarity	NPC470213
0.8936	High Similarity	NPC212890
0.8931	High Similarity	NPC191037
0.8931	High Similarity	NPC178284
0.8931	High Similarity	NPC58607
0.8929	High Similarity	NPC138227
0.8929	High Similarity	NPC168579
0.8929	High Similarity	NPC76176
0.8929	High Similarity	NPC129417
0.8929	High Similarity	NPC469313
0.8929	High Similarity	NPC283995
0.8929	High Similarity	NPC470235
0.8923	High Similarity	NPC48990
0.8923	High Similarity	NPC293701

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 NPC25695 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	868
0.2-0.3	1920
0.3-0.4	2750
0.4-0.5	1641
0.5-0.6	920
0.6-0.7	595
0.7-0.8	138
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9015	High Similarity	NPD3027	Phase 3
0.8676	High Similarity	NPD1613	Approved
0.8676	High Similarity	NPD1612	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD3705	Approved
0.8382	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1357	Approved
0.8309	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD1091	Approved
0.8267	Intermediate Similarity	NPD37	Approved
0.8243	Intermediate Similarity	NPD1653	Approved
0.8224	Intermediate Similarity	NPD4966	Approved
0.8224	Intermediate Similarity	NPD4965	Approved
0.8224	Intermediate Similarity	NPD4967	Phase 2
0.8129	Intermediate Similarity	NPD7199	Phase 2
0.8117	Intermediate Similarity	NPD6234	Discontinued
0.8101	Intermediate Similarity	NPD3818	Discontinued
0.8015	Intermediate Similarity	NPD2982	Phase 2
0.8015	Intermediate Similarity	NPD2983	Phase 2
0.7945	Intermediate Similarity	NPD6674	Discontinued
0.7941	Intermediate Similarity	NPD2981	Phase 2
0.7937	Intermediate Similarity	NPD7054	Approved
0.7931	Intermediate Similarity	NPD7266	Discontinued
0.7914	Intermediate Similarity	NPD3018	Phase 2
0.7911	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5058	Phase 3
0.7888	Intermediate Similarity	NPD7472	Approved
0.7888	Intermediate Similarity	NPD7074	Phase 3
0.7875	Intermediate Similarity	NPD7228	Approved
0.7857	Intermediate Similarity	NPD4908	Phase 1
0.7852	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1548	Phase 1
0.7792	Intermediate Similarity	NPD1934	Approved
0.7756	Intermediate Similarity	NPD3882	Suspended
0.7746	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7808	Phase 3
0.7742	Intermediate Similarity	NPD2977	Approved
0.7742	Intermediate Similarity	NPD2978	Approved
0.7737	Intermediate Similarity	NPD1610	Phase 2
0.773	Intermediate Similarity	NPD6797	Phase 2
0.7727	Intermediate Similarity	NPD5283	Phase 1
0.771	Intermediate Similarity	NPD228	Approved
0.7697	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7251	Discontinued
0.7662	Intermediate Similarity	NPD4675	Approved
0.7662	Intermediate Similarity	NPD4678	Approved
0.766	Intermediate Similarity	NPD2861	Phase 2
0.7636	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2801	Approved
0.7622	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD2684	Approved
0.7597	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4236	Phase 3
0.7584	Intermediate Similarity	NPD4237	Approved
0.758	Intermediate Similarity	NPD3817	Phase 2
0.7576	Intermediate Similarity	NPD6559	Discontinued
0.7576	Intermediate Similarity	NPD7240	Approved
0.7568	Intermediate Similarity	NPD1375	Discontinued
0.7551	Intermediate Similarity	NPD5588	Approved
0.7532	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6166	Phase 2
0.7531	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD7843	Approved
0.7517	Intermediate Similarity	NPD1558	Phase 1
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4536	Approved
0.7483	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4538	Approved
0.7481	Intermediate Similarity	NPD7157	Approved
0.7467	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1652	Phase 2
0.7431	Intermediate Similarity	NPD4625	Phase 3
0.7405	Intermediate Similarity	NPD290	Approved
0.7397	Intermediate Similarity	NPD3620	Phase 2
0.7397	Intermediate Similarity	NPD4060	Phase 1
0.7397	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5844	Phase 1
0.7386	Intermediate Similarity	NPD1511	Approved
0.7386	Intermediate Similarity	NPD4357	Discontinued
0.7379	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4749	Approved
0.7357	Intermediate Similarity	NPD422	Phase 1
0.7351	Intermediate Similarity	NPD3060	Approved
0.7351	Intermediate Similarity	NPD4162	Approved
0.7338	Intermediate Similarity	NPD5126	Approved
0.7338	Intermediate Similarity	NPD5125	Phase 3
0.7338	Intermediate Similarity	NPD4123	Phase 3
0.7333	Intermediate Similarity	NPD3540	Phase 1
0.7329	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6233	Phase 2
0.7315	Intermediate Similarity	NPD5960	Phase 3
0.7308	Intermediate Similarity	NPD3687	Approved
0.7308	Intermediate Similarity	NPD3686	Approved
0.7303	Intermediate Similarity	NPD4628	Phase 3
0.7303	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4110	Phase 3
0.7301	Intermediate Similarity	NPD3787	Discontinued
0.7297	Intermediate Similarity	NPD6653	Approved
0.7296	Intermediate Similarity	NPD5772	Approved
0.7296	Intermediate Similarity	NPD5773	Approved
0.729	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1512	Approved
0.7289	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD291	Approved
0.7284	Intermediate Similarity	NPD5494	Approved
0.7267	Intermediate Similarity	NPD3539	Phase 1
0.7261	Intermediate Similarity	NPD4005	Discontinued
0.7255	Intermediate Similarity	NPD2677	Approved
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7241	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3382	Approved
0.7233	Intermediate Similarity	NPD3384	Approved
0.7233	Intermediate Similarity	NPD3383	Approved
0.723	Intermediate Similarity	NPD5735	Approved
0.723	Intermediate Similarity	NPD6355	Discontinued
0.723	Intermediate Similarity	NPD5124	Phase 1
0.723	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5763	Approved
0.7219	Intermediate Similarity	NPD5762	Approved
0.7214	Intermediate Similarity	NPD6516	Phase 2
0.7214	Intermediate Similarity	NPD5846	Approved
0.7203	Intermediate Similarity	NPD8651	Approved
0.7197	Intermediate Similarity	NPD968	Approved
0.7192	Intermediate Similarity	NPD7095	Approved
0.719	Intermediate Similarity	NPD6331	Phase 2
0.719	Intermediate Similarity	NPD3892	Phase 2
0.7188	Intermediate Similarity	NPD8455	Phase 2
0.7183	Intermediate Similarity	NPD2231	Phase 2
0.7183	Intermediate Similarity	NPD2235	Phase 2
0.7164	Intermediate Similarity	NPD3021	Approved
0.7164	Intermediate Similarity	NPD3022	Approved
0.7164	Intermediate Similarity	NPD556	Approved
0.7161	Intermediate Similarity	NPD6799	Approved
0.716	Intermediate Similarity	NPD7685	Pre-registration
0.7152	Intermediate Similarity	NPD3454	Phase 3
0.7143	Intermediate Similarity	NPD2563	Approved
0.7143	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD2219	Phase 1
0.7143	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD2560	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD3685	Discontinued
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.7124	Intermediate Similarity	NPD5177	Phase 3
0.7114	Intermediate Similarity	NPD230	Phase 1
0.7114	Intermediate Similarity	NPD4340	Discontinued
0.711	Intermediate Similarity	NPD6841	Approved
0.711	Intermediate Similarity	NPD6843	Phase 3
0.711	Intermediate Similarity	NPD6842	Approved
0.7107	Intermediate Similarity	NPD4380	Phase 2
0.7103	Intermediate Similarity	NPD6584	Phase 3
0.7101	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6671	Approved
0.7101	Intermediate Similarity	NPD7007	Discovery
0.7097	Intermediate Similarity	NPD7124	Phase 2
0.7097	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4062	Phase 3
0.7093	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7033	Discontinued
0.7081	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1242	Phase 1
0.7071	Intermediate Similarity	NPD1182	Approved
0.707	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2424	Discontinued
0.7055	Intermediate Similarity	NPD7075	Discontinued
0.7051	Intermediate Similarity	NPD7213	Phase 3
0.7051	Intermediate Similarity	NPD1774	Approved
0.7051	Intermediate Similarity	NPD7212	Phase 2
0.7047	Intermediate Similarity	NPD4140	Approved
0.7047	Intermediate Similarity	NPD2238	Phase 2
0.7042	Intermediate Similarity	NPD3496	Discontinued
0.7039	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2161	Phase 2
0.7025	Intermediate Similarity	NPD5403	Approved
0.702	Intermediate Similarity	NPD7097	Phase 1
0.7019	Intermediate Similarity	NPD6801	Discontinued
0.7018	Intermediate Similarity	NPD7549	Discontinued
0.7007	Intermediate Similarity	NPD5535	Approved
0.7006	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7447	Phase 1
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6232	Discontinued
0.6986	Remote Similarity	NPD558	Phase 2
0.6978	Remote Similarity	NPD7680	Approved
0.6975	Remote Similarity	NPD1465	Phase 2
0.6974	Remote Similarity	NPD4108	Discontinued
0.6968	Remote Similarity	NPD4535	Phase 3
0.6962	Remote Similarity	NPD7526	Approved
0.6962	Remote Similarity	NPD52	Approved
0.6962	Remote Similarity	NPD7527	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