NPASS Compound

Structure

CID226738 OpenBabel06191716022D 33 35 0 0 1 0 0 0 0 0999 V2000 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 -3.4641 -2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 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 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 1 9 1 0 0 0 0 2 7 1 0 0 0 0 2 10 2 0 0 0 0 3 8 2 0 0 0 0 3 11 1 0 0 0 0 4 8 1 0 0 0 0 4 12 2 0 0 0 0 5 32 1 0 0 0 0 6 14 1 0 0 0 0 6 31 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 15 2 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 22 1 0 0 0 0 11 16 2 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 24 1 0 0 0 0 13 5 1 1 0 0 0 13 17 1 0 0 0 0 13 31 1 0 0 0 0 14 18 1 0 0 0 0 14 33 1 6 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 6 0 0 0 18 28 1 1 0 0 0 19 29 2 0 0 0 0 19 32 1 0 0 0 0 20 30 2 0 0 0 0 20 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.09
Volume:	421.988
LogP:	0.483
LogD:	0.232
LogS:	-2.481
# Rotatable Bonds:	7
TPSA:	223.67
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	3.971
Fsp3:	0.3
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.514
MDCK Permeability:	1.145411079050973e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.834
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	89.9246826171875%
Volume Distribution (VD):	0.432
Pgp-substrate:	12.904256820678711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.193
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.298
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	13.018
Half-life (T1/2):	0.969

ADMET: Toxicity

hERG Blockers:	0.387
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.877
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.959
Carcinogencity:	0.049
Eye Corrosion:	0.004
Eye Irritation:	0.916
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC226738

Natural Product ID:	NPC226738
*Common Name:**	Ginnalin A
IUPAC Name:	[(2R,3S,4S,5S)-3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms:	Ginnalin A
Standard InCHIKey:	IGKWMHUOBKCUQU-LTCOOKNTSA-N
Standard InCHI:	InChI=1S/C20H20O13/c21-9-1-7(2-10(22)15(9)25)19(29)32-5-13-17(27)18(28)14(6-31-13)33-20(30)8-3-11(23)16(26)12(24)4-8/h1-4,13-14,17-18,21-28H,5-6H2/t13-,14+,17-,18-/m1/s1
SMILES:	O[C@@H]1[C@H](OC[C@@H]([C@H]1O)OC(=O)c1cc(O)c(c(c1)O)O)COC(=O)c1cc(O)c(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1933684
PubChem CID:	5318457
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0001251] Gallic acid and derivatives [CHEMONTID:0003539] Galloyl esters

*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
NPO28946	Acer rubrum	Species	Sapindaceae	Eukaryota	Stems	n.a.	n.a.	PMID[22079755]
NPO28946	Acer rubrum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26209.1	Acer tataricum subsp. ginnala	Subspecies	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28946	Acer rubrum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28946	Acer rubrum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26209.1	Acer tataricum subsp. ginnala	Subspecies	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28946	Acer rubrum	Species	Sapindaceae	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	95380.0	nM	PMID[480781]
NPT1	Others	Radical scavenging activity		IC50	=	17740.0	nM	PMID[480781]

☑ 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 NPC226738 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	338
0.1-0.2	1411
0.2-0.3	3400
0.3-0.4	8034
0.4-0.5	10285
0.5-0.6	4482
0.6-0.7	5882
0.7-0.8	7853
0.8-0.85	758
0.85-0.9	181
0.9-0.95	56
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC121573
1.0	High Similarity	NPC190587
1.0	High Similarity	NPC22176
0.9714	High Similarity	NPC120621
0.9714	High Similarity	NPC142528
0.9714	High Similarity	NPC248257
0.9706	High Similarity	NPC225036
0.9706	High Similarity	NPC105525
0.9706	High Similarity	NPC75763
0.9706	High Similarity	NPC12218
0.9645	High Similarity	NPC92117
0.9574	High Similarity	NPC43123
0.951	High Similarity	NPC140151
0.9507	High Similarity	NPC42464
0.9489	High Similarity	NPC239943
0.9441	High Similarity	NPC306343
0.9429	High Similarity	NPC229036
0.9429	High Similarity	NPC114242
0.9429	High Similarity	NPC50221
0.9379	High Similarity	NPC3746
0.9379	High Similarity	NPC205037
0.9379	High Similarity	NPC44260
0.9379	High Similarity	NPC16024
0.9379	High Similarity	NPC61152
0.9371	High Similarity	NPC75945
0.9362	High Similarity	NPC108455
0.927	High Similarity	NPC18646
0.9252	High Similarity	NPC203757
0.9241	High Similarity	NPC252979
0.9203	High Similarity	NPC156892
0.9189	High Similarity	NPC247629
0.9189	High Similarity	NPC239019
0.9178	High Similarity	NPC75695
0.9128	High Similarity	NPC1913
0.9128	High Similarity	NPC238419
0.9128	High Similarity	NPC472860
0.9128	High Similarity	NPC172419
0.9124	High Similarity	NPC156124
0.9124	High Similarity	NPC1321
0.9124	High Similarity	NPC304929
0.9122	High Similarity	NPC145425
0.9097	High Similarity	NPC268366
0.9067	High Similarity	NPC287872
0.9067	High Similarity	NPC74319
0.9067	High Similarity	NPC289811
0.9067	High Similarity	NPC160780
0.906	High Similarity	NPC250436
0.906	High Similarity	NPC291948
0.906	High Similarity	NPC300845
0.906	High Similarity	NPC104983
0.906	High Similarity	NPC88803
0.9048	High Similarity	NPC227485
0.9041	High Similarity	NPC473091
0.9014	High Similarity	NPC35702
0.9014	High Similarity	NPC206095
0.9014	High Similarity	NPC471027
0.9014	High Similarity	NPC297517
0.9014	High Similarity	NPC224389
0.9014	High Similarity	NPC13818
0.9014	High Similarity	NPC477335
0.9007	High Similarity	NPC119125
0.9007	High Similarity	NPC24164
0.9007	High Similarity	NPC166277
0.9007	High Similarity	NPC203020
0.9007	High Similarity	NPC289346
0.9007	High Similarity	NPC239966
0.9007	High Similarity	NPC24627
0.9	High Similarity	NPC68324
0.9	High Similarity	NPC160512
0.9	High Similarity	NPC156818
0.9	High Similarity	NPC114179
0.9	High Similarity	NPC474010
0.9	High Similarity	NPC135222
0.9	High Similarity	NPC289322
0.9	High Similarity	NPC38779
0.8993	High Similarity	NPC156624
0.8993	High Similarity	NPC172920
0.8978	High Similarity	NPC264145
0.8973	High Similarity	NPC476394
0.8973	High Similarity	NPC98809
0.8951	High Similarity	NPC284948
0.8951	High Similarity	NPC220664
0.8951	High Similarity	NPC43158
0.8951	High Similarity	NPC277315
0.8951	High Similarity	NPC37331
0.8951	High Similarity	NPC319628
0.8951	High Similarity	NPC303090
0.8951	High Similarity	NPC258469
0.8951	High Similarity	NPC472016
0.8951	High Similarity	NPC192831
0.8947	High Similarity	NPC472859
0.8947	High Similarity	NPC25389
0.8947	High Similarity	NPC311803
0.894	High Similarity	NPC210501
0.894	High Similarity	NPC318826
0.894	High Similarity	NPC104222
0.894	High Similarity	NPC87317
0.894	High Similarity	NPC114791
0.894	High Similarity	NPC141331
0.8936	High Similarity	NPC152942
0.8936	High Similarity	NPC302857
0.8936	High Similarity	NPC37250
0.8936	High Similarity	NPC219428
0.8936	High Similarity	NPC142703
0.8936	High Similarity	NPC278068
0.8933	High Similarity	NPC318432
0.8933	High Similarity	NPC134925
0.8919	High Similarity	NPC163883
0.8919	High Similarity	NPC93498
0.8904	High Similarity	NPC81835
0.8904	High Similarity	NPC472969
0.8897	High Similarity	NPC473867
0.8889	High Similarity	NPC33298
0.8889	High Similarity	NPC285108
0.8889	High Similarity	NPC134975
0.8889	High Similarity	NPC14030
0.8889	High Similarity	NPC90905
0.8889	High Similarity	NPC291957
0.8889	High Similarity	NPC4013
0.8882	High Similarity	NPC53889
0.8874	High Similarity	NPC4747
0.8874	High Similarity	NPC104275
0.8873	High Similarity	NPC295492
0.8873	High Similarity	NPC476820
0.8873	High Similarity	NPC274891
0.8873	High Similarity	NPC474875
0.8873	High Similarity	NPC205751
0.8873	High Similarity	NPC476819
0.8873	High Similarity	NPC26241
0.8873	High Similarity	NPC303683
0.8859	High Similarity	NPC310661
0.8859	High Similarity	NPC19380
0.8859	High Similarity	NPC105827
0.8859	High Similarity	NPC146277
0.8836	High Similarity	NPC229264
0.8832	High Similarity	NPC94810
0.8831	High Similarity	NPC470898
0.88	High Similarity	NPC125487
0.88	High Similarity	NPC144801
0.88	High Similarity	NPC191046
0.88	High Similarity	NPC291510
0.88	High Similarity	NPC281703
0.88	High Similarity	NPC116850
0.88	High Similarity	NPC327032
0.88	High Similarity	NPC43872
0.88	High Similarity	NPC197188
0.88	High Similarity	NPC238672
0.88	High Similarity	NPC194095
0.8786	High Similarity	NPC248150
0.8776	High Similarity	NPC476463
0.8776	High Similarity	NPC471076
0.8776	High Similarity	NPC192568
0.8774	High Similarity	NPC471788
0.8767	High Similarity	NPC474465
0.8758	High Similarity	NPC476373
0.875	High Similarity	NPC49173
0.8733	High Similarity	NPC474656
0.8732	High Similarity	NPC25305
0.8732	High Similarity	NPC125417
0.8732	High Similarity	NPC112068
0.8732	High Similarity	NPC95679
0.8732	High Similarity	NPC110899
0.8718	High Similarity	NPC13481
0.8718	High Similarity	NPC207575
0.8718	High Similarity	NPC175793
0.8716	High Similarity	NPC107636
0.8699	High Similarity	NPC477333
0.8696	High Similarity	NPC226855
0.8684	High Similarity	NPC471405
0.8675	High Similarity	NPC287504
0.8671	High Similarity	NPC283560
0.8671	High Similarity	NPC24295
0.8667	High Similarity	NPC228662
0.8667	High Similarity	NPC134905
0.8667	High Similarity	NPC36130
0.8662	High Similarity	NPC217781
0.8662	High Similarity	NPC470271
0.8662	High Similarity	NPC311389
0.8662	High Similarity	NPC116745
0.8654	High Similarity	NPC162169
0.8654	High Similarity	NPC142614
0.8654	High Similarity	NPC166851
0.8652	High Similarity	NPC68517
0.8652	High Similarity	NPC106406
0.8645	High Similarity	NPC476372
0.8645	High Similarity	NPC41009
0.8645	High Similarity	NPC476371
0.8639	High Similarity	NPC98356
0.8639	High Similarity	NPC262282
0.863	High Similarity	NPC473090
0.8627	High Similarity	NPC226759
0.8627	High Similarity	NPC133984
0.8618	High Similarity	NPC10205
0.8618	High Similarity	NPC82592
0.8618	High Similarity	NPC16082
0.8611	High Similarity	NPC86744
0.8609	High Similarity	NPC157898
0.8608	High Similarity	NPC95421
0.8608	High Similarity	NPC198125
0.8608	High Similarity	NPC658

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 NPC226738 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	816
0.2-0.3	1763
0.3-0.4	2698
0.4-0.5	2009
0.5-0.6	1039
0.6-0.7	424
0.7-0.8	102
0.8-0.85	11
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9124	High Similarity	NPD230	Phase 1
0.906	High Similarity	NPD4868	Clinical (unspecified phase)
0.8951	High Similarity	NPD6190	Approved
0.85	High Similarity	NPD7993	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD9269	Phase 2
0.8366	Intermediate Similarity	NPD1934	Approved
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8312	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1465	Phase 2
0.8282	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD4380	Phase 2
0.8194	Intermediate Similarity	NPD2801	Approved
0.8187	Intermediate Similarity	NPD6166	Phase 2
0.8187	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD7266	Discontinued
0.8162	Intermediate Similarity	NPD9268	Approved
0.8148	Intermediate Similarity	NPD7054	Approved
0.8141	Intermediate Similarity	NPD3817	Phase 2
0.8098	Intermediate Similarity	NPD7074	Phase 3
0.8098	Intermediate Similarity	NPD7472	Approved
0.8089	Intermediate Similarity	NPD3882	Suspended
0.8079	Intermediate Similarity	NPD1511	Approved
0.8049	Intermediate Similarity	NPD6797	Phase 2
0.8038	Intermediate Similarity	NPD7075	Discontinued
0.8038	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD7685	Pre-registration
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7974	Intermediate Similarity	NPD1512	Approved
0.795	Intermediate Similarity	NPD6232	Discontinued
0.7922	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD5402	Approved
0.7881	Intermediate Similarity	NPD4628	Phase 3
0.7875	Intermediate Similarity	NPD6234	Discontinued
0.7871	Intermediate Similarity	NPD1653	Approved
0.7848	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7808	Phase 3
0.7826	Intermediate Similarity	NPD9545	Approved
0.7805	Intermediate Similarity	NPD7473	Discontinued
0.7799	Intermediate Similarity	NPD5353	Approved
0.7793	Intermediate Similarity	NPD3027	Phase 3
0.7785	Intermediate Similarity	NPD37	Approved
0.7785	Intermediate Similarity	NPD6801	Discontinued
0.7758	Intermediate Similarity	NPD7228	Approved
0.7755	Intermediate Similarity	NPD1613	Approved
0.7755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD4966	Approved
0.775	Intermediate Similarity	NPD4967	Phase 2
0.775	Intermediate Similarity	NPD4965	Approved
0.7748	Intermediate Similarity	NPD1549	Phase 2
0.7736	Intermediate Similarity	NPD7819	Suspended
0.7727	Intermediate Similarity	NPD6799	Approved
0.7692	Intermediate Similarity	NPD5403	Approved
0.7682	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1510	Phase 2
0.7655	Intermediate Similarity	NPD9494	Approved
0.7632	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3764	Approved
0.7613	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7411	Suspended
0.7607	Intermediate Similarity	NPD5494	Approved
0.7602	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3455	Phase 2
0.7574	Intermediate Similarity	NPD6559	Discontinued
0.7564	Intermediate Similarity	NPD5401	Approved
0.755	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5242	Approved
0.7455	Intermediate Similarity	NPD7199	Phase 2
0.7452	Intermediate Similarity	NPD2533	Approved
0.7452	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2534	Approved
0.7452	Intermediate Similarity	NPD2532	Approved
0.7438	Intermediate Similarity	NPD6599	Discontinued
0.74	Intermediate Similarity	NPD1240	Approved
0.7391	Intermediate Similarity	NPD6386	Approved
0.7391	Intermediate Similarity	NPD6385	Approved
0.7386	Intermediate Similarity	NPD2935	Discontinued
0.7386	Intermediate Similarity	NPD2796	Approved
0.7379	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8150	Discontinued
0.7355	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD447	Suspended
0.7349	Intermediate Similarity	NPD6959	Discontinued
0.7321	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8166	Discontinued
0.7303	Intermediate Similarity	NPD1607	Approved
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3749	Approved
0.7267	Intermediate Similarity	NPD7240	Approved
0.7262	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3751	Discontinued
0.7233	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7768	Phase 2
0.7208	Intermediate Similarity	NPD3748	Approved
0.7208	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD919	Approved
0.7125	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1933	Approved
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD8313	Approved
0.7074	Intermediate Similarity	NPD8151	Discontinued
0.7069	Intermediate Similarity	NPD7039	Approved
0.7069	Intermediate Similarity	NPD7038	Approved
0.7063	Intermediate Similarity	NPD4357	Discontinued
0.7063	Intermediate Similarity	NPD7390	Discontinued
0.7063	Intermediate Similarity	NPD9493	Approved
0.7062	Intermediate Similarity	NPD8434	Phase 2
0.7059	Intermediate Similarity	NPD3926	Phase 2
0.7055	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1203	Approved
0.7025	Intermediate Similarity	NPD1652	Phase 2
0.7011	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD5710	Approved
0.7	Intermediate Similarity	NPD5711	Approved
0.6988	Remote Similarity	NPD8455	Phase 2
0.697	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1608	Approved
0.6957	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3226	Approved
0.6949	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5404	Approved
0.6943	Remote Similarity	NPD5405	Approved
0.6943	Remote Similarity	NPD5406	Approved
0.6943	Remote Similarity	NPD6099	Approved
0.6943	Remote Similarity	NPD6100	Approved
0.6943	Remote Similarity	NPD5408	Approved
0.6941	Remote Similarity	NPD8127	Discontinued
0.6941	Remote Similarity	NPD1247	Approved
0.6933	Remote Similarity	NPD920	Approved
0.6928	Remote Similarity	NPD6798	Discontinued
0.6923	Remote Similarity	NPD6534	Approved
0.6923	Remote Similarity	NPD6535	Approved
0.6914	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2983	Phase 2
0.6913	Remote Similarity	NPD2982	Phase 2
0.6908	Remote Similarity	NPD6832	Phase 2
0.6903	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7435	Discontinued
0.6897	Remote Similarity	NPD5536	Phase 2
0.6897	Remote Similarity	NPD7286	Phase 2
0.6879	Remote Similarity	NPD7033	Discontinued
0.6871	Remote Similarity	NPD6273	Approved
0.6867	Remote Similarity	NPD3225	Approved
0.6864	Remote Similarity	NPD6971	Discontinued
0.6862	Remote Similarity	NPD8320	Phase 1
0.6862	Remote Similarity	NPD8319	Approved
0.6848	Remote Similarity	NPD7458	Discontinued
0.6848	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2981	Phase 2
0.6842	Remote Similarity	NPD3018	Phase 2
0.6835	Remote Similarity	NPD9570	Approved
0.6828	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6782	Approved
0.6828	Remote Similarity	NPD6781	Approved
0.6828	Remote Similarity	NPD6777	Approved
0.6828	Remote Similarity	NPD6778	Approved
0.6828	Remote Similarity	NPD6779	Approved
0.6828	Remote Similarity	NPD6776	Approved
0.6828	Remote Similarity	NPD6780	Approved
0.6818	Remote Similarity	NPD2313	Discontinued
0.6813	Remote Similarity	NPD2800	Approved
0.6813	Remote Similarity	NPD1243	Approved
0.6811	Remote Similarity	NPD7700	Phase 2
0.6811	Remote Similarity	NPD7699	Phase 2
0.6809	Remote Similarity	NPD7680	Approved
0.6802	Remote Similarity	NPD7229	Phase 3
0.6797	Remote Similarity	NPD4908	Phase 1
0.6795	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6355	Discontinued
0.6795	Remote Similarity	NPD5124	Phase 1
0.6792	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2346	Discontinued
0.679	Remote Similarity	NPD7440	Discontinued
0.679	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1610	Phase 2
0.6779	Remote Similarity	NPD422	Phase 1
0.6776	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4062	Phase 3
0.6772	Remote Similarity	NPD2799	Discontinued
0.6772	Remote Similarity	NPD4308	Phase 3
0.677	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4110	Phase 3
0.6757	Remote Similarity	NPD17	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