NPASS Compound

Structure

NPC471719 OpenBabel07101718312D 34 35 0 0 1 0 0 0 0 0999 V2000 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 15 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 9 1 0 0 0 0 9 16 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 19 2 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 21 2 0 0 0 0 14 33 1 0 0 0 0 15 26 2 0 0 0 0 15 33 1 0 0 0 0 17 23 1 0 0 0 0 18 25 2 0 0 0 0 18 28 1 0 0 0 0 19 25 1 0 0 0 0 19 29 1 0 0 0 0 20 24 2 0 0 0 0 20 30 1 0 0 0 0 21 24 1 0 0 0 0 21 31 1 0 0 0 0 22 14 1 6 0 0 0 22 23 1 0 0 0 0 22 34 1 0 0 0 0 23 27 1 1 0 0 0 24 32 1 0 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.2
Volume:	481.864
LogP:	2.478
LogD:	2.614
LogS:	-3.865
# Rotatable Bonds:	14
TPSA:	101.91
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	3.399
Fsp3:	0.4
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:	-4.643
MDCK Permeability:	2.4996632419060916e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.652
Plasma Protein Binding (PPB):	75.46554565429688%
Volume Distribution (VD):	0.914
Pgp-substrate:	22.46989631652832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.474
CYP2C19-inhibitor:	0.265
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.292
CYP2C9-substrate:	0.818
CYP2D6-inhibitor:	0.466
CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.932
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	5.813
Half-life (T1/2):	0.8

ADMET: Toxicity

hERG Blockers:	0.25
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.343
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.163
Skin Sensitization:	0.512
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC471719

Natural Product ID:	NPC471719
*Common Name:**	Saurucinol D
IUPAC Name:	[(2R,3R)-2-(2,6-dimethoxy-4-prop-2-enylphenoxy)-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl] acetate
Synonyms:
Standard InCHIKey:	QQKYKRFSZPVBDT-DHIUTWEWSA-N
Standard InCHI:	InChI=1S/C25H32O9/c1-8-9-16-10-18(28-3)25(19(11-16)29-4)34-22(14-33-15(2)26)23(27)17-12-20(30-5)24(32-7)21(13-17)31-6/h8,10-13,22-23,27H,1,9,14H2,2-7H3/t22-,23-/m1/s1
SMILES:	C=CCc1cc(OC)c(c(c1)OC)O[C@@H]([C@@H](c1cc(OC)c(c(c1)OC)OC)O)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105551
PubChem CID:	76317428
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	=	3.7	n.a.	PMID[463767]
NPT27	Others	Unspecified		CC50	=	194500.0	nM	PMID[463767]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	53300.0	nM	PMID[463767]

☑ 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 NPC471719 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	296
0.1-0.2	1314
0.2-0.3	3923
0.3-0.4	10263
0.4-0.5	8346
0.5-0.6	4015
0.6-0.7	6743
0.7-0.8	6122
0.8-0.85	1155
0.85-0.9	437
0.9-0.95	62
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9845	High Similarity	NPC309744
0.9612	High Similarity	NPC30043
0.9612	High Similarity	NPC469625
0.9612	High Similarity	NPC469613
0.9535	High Similarity	NPC79184
0.9535	High Similarity	NPC469612
0.9535	High Similarity	NPC469614
0.9535	High Similarity	NPC307042
0.9457	High Similarity	NPC3439
0.9457	High Similarity	NPC470258
0.9457	High Similarity	NPC285339
0.9457	High Similarity	NPC218856
0.9457	High Similarity	NPC202582
0.9457	High Similarity	NPC222004
0.9457	High Similarity	NPC226788
0.9457	High Similarity	NPC190629
0.9457	High Similarity	NPC210623
0.9457	High Similarity	NPC273295
0.9389	High Similarity	NPC16208
0.9389	High Similarity	NPC184447
0.9389	High Similarity	NPC35932
0.9389	High Similarity	NPC160991
0.9389	High Similarity	NPC7903
0.938	High Similarity	NPC210674
0.9313	High Similarity	NPC470096
0.9313	High Similarity	NPC470095
0.9313	High Similarity	NPC472597
0.9302	High Similarity	NPC474119
0.9248	High Similarity	NPC310854
0.9248	High Similarity	NPC170694
0.9242	High Similarity	NPC470752
0.9237	High Similarity	NPC472338
0.9237	High Similarity	NPC476399
0.9191	High Similarity	NPC267291
0.9167	High Similarity	NPC309787
0.9149	High Similarity	NPC475250
0.9149	High Similarity	NPC106138
0.9111	High Similarity	NPC172818
0.9111	High Similarity	NPC25695
0.9104	High Similarity	NPC135127
0.9098	High Similarity	NPC5423
0.9078	High Similarity	NPC187398
0.9078	High Similarity	NPC476348
0.907	High Similarity	NPC109822
0.907	High Similarity	NPC94276
0.9058	High Similarity	NPC278469
0.9058	High Similarity	NPC469559
0.9058	High Similarity	NPC193722
0.9051	High Similarity	NPC266197
0.9051	High Similarity	NPC291101
0.9044	High Similarity	NPC126206
0.9037	High Similarity	NPC472337
0.9037	High Similarity	NPC61946
0.9037	High Similarity	NPC311430
0.9037	High Similarity	NPC224941
0.903	High Similarity	NPC263064
0.903	High Similarity	NPC475840
0.9015	High Similarity	NPC170844
0.9015	High Similarity	NPC476968
0.9008	High Similarity	NPC111247
0.9008	High Similarity	NPC147821
0.9008	High Similarity	NPC41706
0.9008	High Similarity	NPC163332
0.9008	High Similarity	NPC292056
0.9008	High Similarity	NPC210355
0.9008	High Similarity	NPC183181
0.9008	High Similarity	NPC319625
0.9008	High Similarity	NPC118787
0.9007	High Similarity	NPC15577
0.9007	High Similarity	NPC476347
0.8992	High Similarity	NPC279379
0.8986	High Similarity	NPC224876
0.8986	High Similarity	NPC83375
0.8978	High Similarity	NPC22517
0.8971	High Similarity	NPC471665
0.8971	High Similarity	NPC472336
0.8971	High Similarity	NPC471664
0.8971	High Similarity	NPC472334
0.8971	High Similarity	NPC306441
0.8971	High Similarity	NPC16435
0.8963	High Similarity	NPC48863
0.8963	High Similarity	NPC111635
0.8963	High Similarity	NPC251981
0.8963	High Similarity	NPC13745
0.8955	High Similarity	NPC201587
0.8955	High Similarity	NPC253105
0.8955	High Similarity	NPC245120
0.8951	High Similarity	NPC205727
0.8951	High Similarity	NPC294522
0.8951	High Similarity	NPC120426
0.8951	High Similarity	NPC21184
0.8951	High Similarity	NPC473091
0.8944	High Similarity	NPC93924
0.8944	High Similarity	NPC477879
0.8939	High Similarity	NPC474651
0.8939	High Similarity	NPC98631
0.8939	High Similarity	NPC206615
0.8939	High Similarity	NPC474623
0.8939	High Similarity	NPC186843
0.8939	High Similarity	NPC470213
0.8936	High Similarity	NPC474054
0.8931	High Similarity	NPC191037
0.8931	High Similarity	NPC58607
0.8931	High Similarity	NPC178284
0.8923	High Similarity	NPC293701
0.8923	High Similarity	NPC48990
0.8923	High Similarity	NPC114901
0.8921	High Similarity	NPC189115
0.8915	High Similarity	NPC261661
0.8915	High Similarity	NPC71090
0.8905	High Similarity	NPC124149
0.8897	High Similarity	NPC470356
0.8897	High Similarity	NPC234333
0.8897	High Similarity	NPC94750
0.8897	High Similarity	NPC260898
0.8897	High Similarity	NPC47398
0.8897	High Similarity	NPC474206
0.8897	High Similarity	NPC121812
0.8897	High Similarity	NPC112939
0.8897	High Similarity	NPC112246
0.8889	High Similarity	NPC69513
0.8889	High Similarity	NPC215833
0.8889	High Similarity	NPC168059
0.8889	High Similarity	NPC49074
0.8889	High Similarity	NPC229442
0.8881	High Similarity	NPC30688
0.8881	High Similarity	NPC474017
0.8881	High Similarity	NPC176903
0.8872	High Similarity	NPC5851
0.8872	High Similarity	NPC86030
0.8865	High Similarity	NPC274960
0.8865	High Similarity	NPC475096
0.8865	High Similarity	NPC143120
0.8865	High Similarity	NPC473909
0.8864	High Similarity	NPC470699
0.8864	High Similarity	NPC242032
0.8855	High Similarity	NPC194519
0.8849	High Similarity	NPC469661
0.8849	High Similarity	NPC300611
0.8841	High Similarity	NPC164148
0.8841	High Similarity	NPC43500
0.8841	High Similarity	NPC212770
0.8841	High Similarity	NPC98777
0.8832	High Similarity	NPC227503
0.8832	High Similarity	NPC302701
0.8832	High Similarity	NPC164857
0.8832	High Similarity	NPC474639
0.8832	High Similarity	NPC471988
0.8832	High Similarity	NPC230734
0.8832	High Similarity	NPC269091
0.8828	High Similarity	NPC302610
0.8828	High Similarity	NPC75695
0.8824	High Similarity	NPC244983
0.8824	High Similarity	NPC187194
0.8824	High Similarity	NPC476387
0.8824	High Similarity	NPC119060
0.8824	High Similarity	NPC474600
0.8824	High Similarity	NPC287745
0.8824	High Similarity	NPC67247
0.8824	High Similarity	NPC237594
0.8824	High Similarity	NPC326095
0.8824	High Similarity	NPC249791
0.8819	High Similarity	NPC477381
0.8815	High Similarity	NPC162093
0.8815	High Similarity	NPC299144
0.8811	High Similarity	NPC102934
0.8811	High Similarity	NPC252402
0.8811	High Similarity	NPC478237
0.8803	High Similarity	NPC205361
0.8803	High Similarity	NPC40222
0.8803	High Similarity	NPC212890
0.8803	High Similarity	NPC268515
0.8797	High Similarity	NPC72529
0.8794	High Similarity	NPC114119
0.8794	High Similarity	NPC87883
0.8794	High Similarity	NPC470097
0.8794	High Similarity	NPC25292
0.8794	High Similarity	NPC471415
0.8794	High Similarity	NPC473045
0.8788	High Similarity	NPC181361
0.8786	High Similarity	NPC475084
0.8786	High Similarity	NPC131971
0.8786	High Similarity	NPC287124
0.8779	High Similarity	NPC122792
0.8779	High Similarity	NPC228972
0.8768	High Similarity	NPC59324
0.8768	High Similarity	NPC65530
0.8768	High Similarity	NPC211549
0.8768	High Similarity	NPC138738
0.8768	High Similarity	NPC474282
0.8768	High Similarity	NPC176051
0.8768	High Similarity	NPC107551
0.8768	High Similarity	NPC474390
0.8768	High Similarity	NPC281780
0.8768	High Similarity	NPC102904
0.8768	High Similarity	NPC326797
0.8768	High Similarity	NPC470413
0.8768	High Similarity	NPC103976
0.8768	High Similarity	NPC477938
0.8767	High Similarity	NPC473236

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 NPC471719 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	821
0.2-0.3	1861
0.3-0.4	2667
0.4-0.5	1705
0.5-0.6	983
0.6-0.7	646
0.7-0.8	200
0.8-0.85	8
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)
0.8382	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1653	Approved
0.8309	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7266	Discontinued
0.8158	Intermediate Similarity	NPD3817	Phase 2
0.8148	Intermediate Similarity	NPD2982	Phase 2
0.8148	Intermediate Similarity	NPD2983	Phase 2
0.8146	Intermediate Similarity	NPD37	Approved
0.8105	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD4967	Phase 2
0.8105	Intermediate Similarity	NPD4966	Approved
0.8105	Intermediate Similarity	NPD4965	Approved
0.8074	Intermediate Similarity	NPD2981	Phase 2
0.8043	Intermediate Similarity	NPD3018	Phase 2
0.8026	Intermediate Similarity	NPD1934	Approved
0.8013	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD6234	Discontinued
0.7945	Intermediate Similarity	NPD1652	Phase 2
0.7937	Intermediate Similarity	NPD7054	Approved
0.7888	Intermediate Similarity	NPD7472	Approved
0.7888	Intermediate Similarity	NPD7074	Phase 3
0.7887	Intermediate Similarity	NPD4060	Phase 1
0.7875	Intermediate Similarity	NPD7228	Approved
0.7868	Intermediate Similarity	NPD422	Phase 1
0.7862	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6166	Phase 2
0.7857	Intermediate Similarity	NPD4908	Phase 1
0.7857	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2801	Approved
0.7836	Intermediate Similarity	NPD1548	Phase 1
0.7826	Intermediate Similarity	NPD5844	Phase 1
0.7817	Intermediate Similarity	NPD6233	Phase 2
0.7801	Intermediate Similarity	NPD7095	Approved
0.7799	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD7843	Approved
0.7778	Intermediate Similarity	NPD6653	Approved
0.777	Intermediate Similarity	NPD4628	Phase 3
0.7764	Intermediate Similarity	NPD3818	Discontinued
0.7763	Intermediate Similarity	NPD3686	Approved
0.7763	Intermediate Similarity	NPD3687	Approved
0.7756	Intermediate Similarity	NPD3882	Suspended
0.7754	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7157	Approved
0.7744	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7808	Phase 3
0.7737	Intermediate Similarity	NPD1091	Approved
0.7737	Intermediate Similarity	NPD1610	Phase 2
0.7727	Intermediate Similarity	NPD5283	Phase 1
0.7718	Intermediate Similarity	NPD6190	Approved
0.771	Intermediate Similarity	NPD228	Approved
0.7708	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5124	Phase 1
0.7708	Intermediate Similarity	NPD6355	Discontinued
0.7707	Intermediate Similarity	NPD7075	Discontinued
0.7692	Intermediate Similarity	NPD5402	Approved
0.7692	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD5762	Approved
0.7687	Intermediate Similarity	NPD5763	Approved
0.7683	Intermediate Similarity	NPD7251	Discontinued
0.7662	Intermediate Similarity	NPD4675	Approved
0.7662	Intermediate Similarity	NPD4678	Approved
0.7651	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4110	Phase 3
0.7628	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6797	Phase 2
0.7622	Intermediate Similarity	NPD6798	Discontinued
0.7622	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1511	Approved
0.7616	Intermediate Similarity	NPD6799	Approved
0.7616	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD2684	Approved
0.7609	Intermediate Similarity	NPD3705	Approved
0.7597	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4340	Discontinued
0.7586	Intermediate Similarity	NPD230	Phase 1
0.7584	Intermediate Similarity	NPD6674	Discontinued
0.7582	Intermediate Similarity	NPD5403	Approved
0.7582	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7240	Approved
0.7569	Intermediate Similarity	NPD4062	Phase 3
0.7564	Intermediate Similarity	NPD6801	Discontinued
0.7536	Intermediate Similarity	NPD3496	Discontinued
0.7535	Intermediate Similarity	NPD2861	Phase 2
0.7519	Intermediate Similarity	NPD5535	Approved
0.7518	Intermediate Similarity	NPD1357	Approved
0.7517	Intermediate Similarity	NPD1558	Phase 1
0.7516	Intermediate Similarity	NPD1512	Approved
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.7516	Intermediate Similarity	NPD7819	Suspended
0.7516	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5536	Phase 2
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4357	Discontinued
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7484	Intermediate Similarity	NPD4381	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	NPD7097	Phase 1
0.7483	Intermediate Similarity	NPD4538	Approved
0.7467	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD8127	Discontinued
0.7451	Intermediate Similarity	NPD5401	Approved
0.745	Intermediate Similarity	NPD3540	Phase 1
0.7436	Intermediate Similarity	NPD4380	Phase 2
0.7432	Intermediate Similarity	NPD7033	Discontinued
0.7431	Intermediate Similarity	NPD4625	Phase 3
0.7429	Intermediate Similarity	NPD1608	Approved
0.7425	Intermediate Similarity	NPD7549	Discontinued
0.7405	Intermediate Similarity	NPD8455	Phase 2
0.7405	Intermediate Similarity	NPD290	Approved
0.7403	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4140	Approved
0.7391	Intermediate Similarity	NPD5585	Approved
0.7383	Intermediate Similarity	NPD6032	Approved
0.7383	Intermediate Similarity	NPD3539	Phase 1
0.7376	Intermediate Similarity	NPD4749	Approved
0.7368	Intermediate Similarity	NPD2219	Phase 1
0.7365	Intermediate Similarity	NPD6559	Discontinued
0.7361	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4162	Approved
0.7351	Intermediate Similarity	NPD3060	Approved
0.7351	Intermediate Similarity	NPD4236	Phase 3
0.7351	Intermediate Similarity	NPD4237	Approved
0.7347	Intermediate Similarity	NPD447	Suspended
0.7343	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3536	Discontinued
0.7338	Intermediate Similarity	NPD4123	Phase 3
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1778	Approved
0.7325	Intermediate Similarity	NPD6599	Discontinued
0.7324	Intermediate Similarity	NPD8651	Approved
0.732	Intermediate Similarity	NPD5058	Phase 3
0.7319	Intermediate Similarity	NPD1894	Discontinued
0.7315	Intermediate Similarity	NPD5588	Approved
0.7315	Intermediate Similarity	NPD5960	Phase 3
0.7303	Intermediate Similarity	NPD3750	Approved
0.7303	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD291	Approved
0.7284	Intermediate Similarity	NPD5494	Approved
0.7279	Intermediate Similarity	NPD3620	Phase 2
0.7279	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7411	Suspended
0.7273	Intermediate Similarity	NPD1358	Approved
0.7267	Intermediate Similarity	NPD1551	Phase 2
0.7262	Intermediate Similarity	NPD7685	Pre-registration
0.7261	Intermediate Similarity	NPD4005	Discontinued
0.7255	Intermediate Similarity	NPD2677	Approved
0.725	Intermediate Similarity	NPD5353	Approved
0.7234	Intermediate Similarity	NPD1535	Discovery
0.723	Intermediate Similarity	NPD5735	Approved
0.7226	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6671	Approved
0.7219	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1375	Discontinued
0.7219	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5846	Approved
0.7214	Intermediate Similarity	NPD6516	Phase 2
0.7214	Intermediate Similarity	NPD17	Approved
0.7211	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7124	Phase 2
0.7208	Intermediate Similarity	NPD6667	Approved
0.7208	Intermediate Similarity	NPD6666	Approved
0.7205	Intermediate Similarity	NPD7768	Phase 2
0.7203	Intermediate Similarity	NPD3225	Approved
0.7197	Intermediate Similarity	NPD968	Approved
0.7195	Intermediate Similarity	NPD3787	Discontinued
0.7195	Intermediate Similarity	NPD7229	Phase 3
0.7193	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5773	Approved
0.7188	Intermediate Similarity	NPD5772	Approved
0.7183	Intermediate Similarity	NPD2231	Phase 2
0.7183	Intermediate Similarity	NPD2235	Phase 2
0.7183	Intermediate Similarity	NPD1481	Phase 2
0.7178	Intermediate Similarity	NPD5677	Discontinued
0.7171	Intermediate Similarity	NPD2424	Discontinued
0.7171	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1549	Phase 2
0.7171	Intermediate Similarity	NPD4534	Discontinued
0.717	Intermediate Similarity	NPD6386	Approved
0.717	Intermediate Similarity	NPD6385	Approved
0.7164	Intermediate Similarity	NPD3021	Approved
0.7164	Intermediate Similarity	NPD3022	Approved
0.7163	Intermediate Similarity	NPD3847	Discontinued
0.716	Intermediate Similarity	NPD7038	Approved
0.716	Intermediate Similarity	NPD7039	Approved
0.7153	Intermediate Similarity	NPD2797	Approved
0.7153	Intermediate Similarity	NPD6362	Approved
0.7152	Intermediate Similarity	NPD2438	Suspended
0.7152	Intermediate Similarity	NPD6100	Approved

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