NPASS Compound

Structure

NPC294972 OpenBabel07101718282D 31 32 0 0 1 0 0 0 0 0999 V2000 -3.4641 0.0000 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 -6.9282 3.0000 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 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 -9.5263 -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 1.0000 0.0000 C 0 0 2 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 -2.5981 1.5000 0.0000 C 0 0 0 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 -10.3923 0.0000 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 15 1 0 0 0 0 9 24 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 18 2 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 13 20 2 0 0 0 0 14 1 1 1 0 0 0 14 21 1 0 0 0 0 14 31 1 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 18 27 1 0 0 0 0 19 22 2 0 0 0 0 19 28 1 0 0 0 0 20 22 1 0 0 0 0 20 29 1 0 0 0 0 21 25 2 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.18
Volume:	438.481
LogP:	2.386
LogD:	2.346
LogS:	-3.982
# Rotatable Bonds:	11
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.54
Synthetic Accessibility Score:	2.897
Fsp3:	0.348
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:	-4.592
MDCK Permeability:	3.2647592888679355e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.491
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.599
Plasma Protein Binding (PPB):	68.12670135498047%
Volume Distribution (VD):	0.466
Pgp-substrate:	24.318838119506836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.899
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.756
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.492
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	6.572
Half-life (T1/2):	0.878

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.125
Drug-inuced Liver Injury (DILI):	0.455
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.639
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC294972

Natural Product ID:	NPC294972
*Common Name:**	(+)-(8R)-3,4,5,3',5'-Pentamethoxy-Delta-7',8'-9'-Hydroxy-7-Oxo-8-O-4'-Neolignan
IUPAC Name:	(2R)-2-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]-1-(3,4,5-trimethoxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	SECJGGUDGJJKDQ-HSBSLETESA-N
Standard InCHI:	InChI=1S/C23H28O8/c1-14(21(25)16-12-19(28-4)22(30-6)20(13-16)29-5)31-23-17(26-2)10-15(8-7-9-24)11-18(23)27-3/h7-8,10-14,24H,9H2,1-6H3/b8-7+/t14-/m1/s1
SMILES:	OC/C=C/c1cc(OC)c(c(c1)OC)O[C@@H](C(=O)c1cc(OC)c(c(c1)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105550
PubChem CID:	76324798
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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	=	2.5	n.a.	PMID[506511]
NPT27	Others	Unspecified		CC50	>	200000.0	nM	PMID[506511]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	80100.0	nM	PMID[506511]

☑ 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 NPC294972 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	394
0.1-0.2	1492
0.2-0.3	4295
0.3-0.4	10226
0.4-0.5	7786
0.5-0.6	3622
0.6-0.7	5536
0.7-0.8	6982
0.8-0.85	2068
0.85-0.9	290
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC28326
0.9315	High Similarity	NPC473091
0.9189	High Similarity	NPC75695
0.8993	High Similarity	NPC62354
0.8947	High Similarity	NPC178854
0.8947	High Similarity	NPC265511
0.8933	High Similarity	NPC236769
0.8933	High Similarity	NPC151425
0.8933	High Similarity	NPC76376
0.8919	High Similarity	NPC299923
0.8919	High Similarity	NPC117463
0.8919	High Similarity	NPC472969
0.8912	High Similarity	NPC9370
0.8912	High Similarity	NPC287495
0.8904	High Similarity	NPC473090
0.8889	High Similarity	NPC52530
0.8889	High Similarity	NPC471515
0.8889	High Similarity	NPC471479
0.8882	High Similarity	NPC189960
0.8882	High Similarity	NPC145425
0.8882	High Similarity	NPC32557
0.8874	High Similarity	NPC304954
0.8874	High Similarity	NPC134677
0.8874	High Similarity	NPC477231
0.8874	High Similarity	NPC257648
0.8867	High Similarity	NPC166753
0.8867	High Similarity	NPC201547
0.8867	High Similarity	NPC50728
0.8867	High Similarity	NPC219330
0.8867	High Similarity	NPC259058
0.8859	High Similarity	NPC261548
0.8859	High Similarity	NPC474903
0.8851	High Similarity	NPC310259
0.8844	High Similarity	NPC293201
0.8844	High Similarity	NPC207732
0.8839	High Similarity	NPC471499
0.8839	High Similarity	NPC308992
0.8836	High Similarity	NPC312256
0.8831	High Similarity	NPC193842
0.8831	High Similarity	NPC195832
0.8831	High Similarity	NPC176300
0.8831	High Similarity	NPC9609
0.8831	High Similarity	NPC18772
0.8831	High Similarity	NPC19687
0.8831	High Similarity	NPC7846
0.8831	High Similarity	NPC25495
0.8831	High Similarity	NPC152166
0.8831	High Similarity	NPC18607
0.8831	High Similarity	NPC143828
0.8831	High Similarity	NPC191459
0.8831	High Similarity	NPC130894
0.8831	High Similarity	NPC253634
0.8831	High Similarity	NPC300943
0.8831	High Similarity	NPC261004
0.8831	High Similarity	NPC105242
0.8831	High Similarity	NPC115798
0.8831	High Similarity	NPC22472
0.8831	High Similarity	NPC4481
0.8831	High Similarity	NPC288669
0.8831	High Similarity	NPC204854
0.8824	High Similarity	NPC320825
0.8824	High Similarity	NPC250922
0.8824	High Similarity	NPC471500
0.8824	High Similarity	NPC13858
0.8824	High Similarity	NPC326037
0.8819	High Similarity	NPC470962
0.8816	High Similarity	NPC86485
0.8816	High Similarity	NPC236223
0.8816	High Similarity	NPC78326
0.8816	High Similarity	NPC162351
0.8816	High Similarity	NPC246204
0.8816	High Similarity	NPC270620
0.8816	High Similarity	NPC58382
0.8816	High Similarity	NPC179126
0.8816	High Similarity	NPC472915
0.8816	High Similarity	NPC287504
0.8816	High Similarity	NPC25127
0.8808	High Similarity	NPC31363
0.88	High Similarity	NPC69752
0.88	High Similarity	NPC181250
0.88	High Similarity	NPC159103
0.879	High Similarity	NPC470457
0.8784	High Similarity	NPC136278
0.8784	High Similarity	NPC213482
0.8784	High Similarity	NPC471590
0.8782	High Similarity	NPC148273
0.8776	High Similarity	NPC119663
0.8774	High Similarity	NPC239966
0.8774	High Similarity	NPC287328
0.8774	High Similarity	NPC282009
0.8774	High Similarity	NPC203020
0.8774	High Similarity	NPC263449
0.8774	High Similarity	NPC470326
0.8767	High Similarity	NPC110419
0.8766	High Similarity	NPC7973
0.8766	High Similarity	NPC93376
0.8766	High Similarity	NPC110070
0.8766	High Similarity	NPC287979
0.8766	High Similarity	NPC305663
0.8766	High Similarity	NPC472438
0.8766	High Similarity	NPC227192
0.8766	High Similarity	NPC470402
0.8766	High Similarity	NPC189179
0.8766	High Similarity	NPC101830
0.8766	High Similarity	NPC78302
0.8766	High Similarity	NPC63454
0.8766	High Similarity	NPC183851
0.8766	High Similarity	NPC176665
0.8766	High Similarity	NPC224137
0.8766	High Similarity	NPC75215
0.8766	High Similarity	NPC29841
0.8766	High Similarity	NPC163524
0.8766	High Similarity	NPC203891
0.8766	High Similarity	NPC235215
0.8766	High Similarity	NPC67876
0.8758	High Similarity	NPC255807
0.8758	High Similarity	NPC31018
0.8758	High Similarity	NPC471746
0.8758	High Similarity	NPC37392
0.875	High Similarity	NPC60972
0.875	High Similarity	NPC123886
0.875	High Similarity	NPC82325
0.875	High Similarity	NPC301123
0.875	High Similarity	NPC55205
0.875	High Similarity	NPC39732
0.875	High Similarity	NPC279989
0.8742	High Similarity	NPC338131
0.8742	High Similarity	NPC260582
0.8734	High Similarity	NPC477517
0.8733	High Similarity	NPC98809
0.8733	High Similarity	NPC195202
0.8733	High Similarity	NPC476394
0.8726	High Similarity	NPC470459
0.8725	High Similarity	NPC165389
0.8718	High Similarity	NPC112418
0.8716	High Similarity	NPC113089
0.871	High Similarity	NPC476410
0.871	High Similarity	NPC187792
0.871	High Similarity	NPC152904
0.871	High Similarity	NPC160780
0.871	High Similarity	NPC22192
0.871	High Similarity	NPC172202
0.871	High Similarity	NPC289811
0.871	High Similarity	NPC55738
0.871	High Similarity	NPC284127
0.8701	High Similarity	NPC292107
0.8701	High Similarity	NPC98661
0.8701	High Similarity	NPC55619
0.8701	High Similarity	NPC245546
0.8701	High Similarity	NPC43243
0.8701	High Similarity	NPC49824
0.8701	High Similarity	NPC268161
0.8701	High Similarity	NPC266960
0.8701	High Similarity	NPC474638
0.8701	High Similarity	NPC200388
0.8701	High Similarity	NPC303255
0.8701	High Similarity	NPC474520
0.8701	High Similarity	NPC472916
0.8701	High Similarity	NPC247017
0.8701	High Similarity	NPC100916
0.8696	High Similarity	NPC476374
0.8693	High Similarity	NPC27532
0.8693	High Similarity	NPC256346
0.8693	High Similarity	NPC18727
0.8693	High Similarity	NPC246328
0.8693	High Similarity	NPC280937
0.8693	High Similarity	NPC325028
0.869	High Similarity	NPC44573
0.8688	High Similarity	NPC72249
0.8688	High Similarity	NPC206123
0.8684	High Similarity	NPC208043
0.8684	High Similarity	NPC50403
0.8684	High Similarity	NPC474388
0.8684	High Similarity	NPC163883
0.8684	High Similarity	NPC260895
0.8684	High Similarity	NPC226973
0.8684	High Similarity	NPC308451
0.8684	High Similarity	NPC93498
0.8684	High Similarity	NPC125062
0.8684	High Similarity	NPC200740
0.8684	High Similarity	NPC472535
0.8684	High Similarity	NPC133953
0.8684	High Similarity	NPC54394
0.8684	High Similarity	NPC252933
0.8684	High Similarity	NPC28274
0.8684	High Similarity	NPC474170
0.8679	High Similarity	NPC158761
0.8679	High Similarity	NPC470456
0.8679	High Similarity	NPC295082
0.8671	High Similarity	NPC72787
0.8671	High Similarity	NPC234052
0.8671	High Similarity	NPC7154
0.8671	High Similarity	NPC36916
0.8671	High Similarity	NPC7688
0.8671	High Similarity	NPC125039
0.8671	High Similarity	NPC36
0.8671	High Similarity	NPC58223
0.8667	High Similarity	NPC119660
0.8667	High Similarity	NPC470511
0.8667	High Similarity	NPC33265

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 NPC294972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	918
0.2-0.3	1743
0.3-0.4	2595
0.4-0.5	1845
0.5-0.6	1036
0.6-0.7	506
0.7-0.8	138
0.8-0.85	25
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9073	High Similarity	NPD3882	Suspended
0.8882	High Similarity	NPD3817	Phase 2
0.8671	High Similarity	NPD6167	Clinical (unspecified phase)
0.8671	High Similarity	NPD6168	Clinical (unspecified phase)
0.8671	High Similarity	NPD6166	Phase 2
0.8627	High Similarity	NPD1934	Approved
0.8591	High Similarity	NPD6799	Approved
0.8571	High Similarity	NPD2801	Approved
0.8506	High Similarity	NPD6801	Discontinued
0.8462	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD3818	Discontinued
0.8415	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7808	Phase 3
0.8408	Intermediate Similarity	NPD7075	Discontinued
0.8405	Intermediate Similarity	NPD6797	Phase 2
0.8397	Intermediate Similarity	NPD5402	Approved
0.8355	Intermediate Similarity	NPD1512	Approved
0.8354	Intermediate Similarity	NPD7251	Discontinued
0.8333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD5494	Approved
0.8301	Intermediate Similarity	NPD5403	Approved
0.8301	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD7054	Approved
0.8261	Intermediate Similarity	NPD3926	Phase 2
0.8258	Intermediate Similarity	NPD6599	Discontinued
0.8243	Intermediate Similarity	NPD2796	Approved
0.8232	Intermediate Similarity	NPD7472	Approved
0.8232	Intermediate Similarity	NPD7074	Phase 3
0.8224	Intermediate Similarity	NPD1511	Approved
0.8171	Intermediate Similarity	NPD5844	Phase 1
0.817	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD5401	Approved
0.8146	Intermediate Similarity	NPD4628	Phase 3
0.8141	Intermediate Similarity	NPD4380	Phase 2
0.8137	Intermediate Similarity	NPD1247	Approved
0.8133	Intermediate Similarity	NPD1549	Phase 2
0.8125	Intermediate Similarity	NPD919	Approved
0.8092	Intermediate Similarity	NPD6190	Approved
0.8067	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7819	Suspended
0.7973	Intermediate Similarity	NPD230	Phase 1
0.7952	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD3027	Phase 3
0.7933	Intermediate Similarity	NPD1510	Phase 2
0.7905	Intermediate Similarity	NPD1240	Approved
0.7891	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1465	Phase 2
0.7866	Intermediate Similarity	NPD6232	Discontinued
0.7862	Intermediate Similarity	NPD7411	Suspended
0.7831	Intermediate Similarity	NPD7473	Discontinued
0.7826	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD9494	Approved
0.78	Intermediate Similarity	NPD1607	Approved
0.7756	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5353	Approved
0.7711	Intermediate Similarity	NPD5242	Approved
0.7702	Intermediate Similarity	NPD37	Approved
0.7697	Intermediate Similarity	NPD7199	Phase 2
0.7679	Intermediate Similarity	NPD3751	Discontinued
0.7677	Intermediate Similarity	NPD3750	Approved
0.7669	Intermediate Similarity	NPD4965	Approved
0.7669	Intermediate Similarity	NPD4967	Phase 2
0.7669	Intermediate Similarity	NPD4966	Approved
0.7667	Intermediate Similarity	NPD943	Approved
0.7667	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1613	Approved
0.766	Intermediate Similarity	NPD5536	Phase 2
0.7655	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6385	Approved
0.764	Intermediate Similarity	NPD6386	Approved
0.7628	Intermediate Similarity	NPD3887	Approved
0.7616	Intermediate Similarity	NPD447	Suspended
0.7602	Intermediate Similarity	NPD6559	Discontinued
0.759	Intermediate Similarity	NPD6959	Discontinued
0.7582	Intermediate Similarity	NPD3748	Approved
0.7574	Intermediate Similarity	NPD2163	Approved
0.7548	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3787	Discontinued
0.7534	Intermediate Similarity	NPD2982	Phase 2
0.7534	Intermediate Similarity	NPD2983	Phase 2
0.7532	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD4357	Discontinued
0.7529	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.7484	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3146	Approved
0.7483	Intermediate Similarity	NPD6233	Phase 2
0.747	Intermediate Similarity	NPD6234	Discontinued
0.7466	Intermediate Similarity	NPD2981	Phase 2
0.7456	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1653	Approved
0.7452	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3018	Phase 2
0.7417	Intermediate Similarity	NPD6798	Discontinued
0.7405	Intermediate Similarity	NPD2354	Approved
0.74	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6832	Phase 2
0.7391	Intermediate Similarity	NPD920	Approved
0.7386	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD8434	Phase 2
0.7386	Intermediate Similarity	NPD6355	Discontinued
0.7376	Intermediate Similarity	NPD1241	Discontinued
0.7372	Intermediate Similarity	NPD2353	Approved
0.7372	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4062	Phase 3
0.7355	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7768	Phase 2
0.7347	Intermediate Similarity	NPD3972	Approved
0.7347	Intermediate Similarity	NPD1608	Approved
0.7341	Intermediate Similarity	NPD5953	Discontinued
0.7333	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD9268	Approved
0.7308	Intermediate Similarity	NPD6100	Approved
0.7308	Intermediate Similarity	NPD2935	Discontinued
0.7308	Intermediate Similarity	NPD6099	Approved
0.7305	Intermediate Similarity	NPD3749	Approved
0.7299	Intermediate Similarity	NPD7038	Approved
0.7299	Intermediate Similarity	NPD7039	Approved
0.7278	Intermediate Similarity	NPD1243	Approved
0.7278	Intermediate Similarity	NPD2800	Approved
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD7228	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2533	Approved
0.7261	Intermediate Similarity	NPD2344	Approved
0.726	Intermediate Similarity	NPD17	Approved
0.7253	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2799	Discontinued
0.7241	Intermediate Similarity	NPD9545	Approved
0.7233	Intermediate Similarity	NPD4110	Phase 3
0.7233	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD9269	Phase 2
0.7195	Intermediate Similarity	NPD3226	Approved
0.7176	Intermediate Similarity	NPD8127	Discontinued
0.7171	Intermediate Similarity	NPD4908	Phase 1
0.7162	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4340	Discontinued
0.7161	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7151	Intermediate Similarity	NPD2403	Approved
0.7134	Intermediate Similarity	NPD7033	Discontinued
0.7133	Intermediate Similarity	NPD5283	Phase 1
0.7126	Intermediate Similarity	NPD7286	Phase 2
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7095	Approved
0.7123	Intermediate Similarity	NPD1548	Phase 1
0.7117	Intermediate Similarity	NPD6273	Approved
0.7115	Intermediate Similarity	NPD6651	Approved
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6971	Discontinued
0.7097	Intermediate Similarity	NPD4060	Phase 1
0.7097	Intermediate Similarity	NPD3142	Approved
0.7097	Intermediate Similarity	NPD3140	Approved
0.7091	Intermediate Similarity	NPD2649	Approved
0.7091	Intermediate Similarity	NPD2651	Approved
0.7091	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1203	Approved
0.7081	Intermediate Similarity	NPD2309	Approved
0.7078	Intermediate Similarity	NPD3268	Approved
0.7078	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1610	Phase 2
0.7047	Intermediate Similarity	NPD422	Phase 1
0.7025	Intermediate Similarity	NPD4308	Phase 3
0.7025	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1876	Approved
0.7012	Intermediate Similarity	NPD5049	Phase 3
0.7006	Intermediate Similarity	NPD7240	Approved
0.7006	Intermediate Similarity	NPD5089	Approved
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5090	Approved
0.7	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD2424	Discontinued
0.7	Intermediate Similarity	NPD4534	Discontinued
0.6988	Remote Similarity	NPD7458	Discontinued
0.6988	Remote Similarity	NPD3455	Phase 2
0.6982	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5977	Approved
0.6982	Remote Similarity	NPD5978	Approved
0.6982	Remote Similarity	NPD4288	Approved
0.6981	Remote Similarity	NPD2438	Suspended
0.6974	Remote Similarity	NPD2797	Approved
0.6968	Remote Similarity	NPD3764	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