NPASS Compound

Structure

NPC469704 OpenBabel07101719152D 34 36 0 0 1 0 0 0 0 0999 V2000 4.3301 -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 4.3301 -3.5000 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 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 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 2.5981 -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 -1.7321 0.0000 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 3.4641 -3.0000 0.0000 C 0 0 0 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 3.4641 -5.0000 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 -0.5000 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 2 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 2 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 15 2 0 0 0 0 2 8 2 0 0 0 0 2 15 1 0 0 0 0 3 9 1 0 0 0 0 3 16 2 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 11 1 0 0 0 0 5 15 1 0 0 0 0 6 12 1 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 26 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 6 0 0 0 20 12 1 6 0 0 0 20 33 1 0 0 0 0 21 14 1 1 0 0 0 21 22 1 0 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 1 0 0 0 23 24 1 0 0 0 0 23 31 1 6 0 0 0 24 25 1 0 0 0 0 24 32 1 6 0 0 0 25 33 1 1 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.22
Volume:	478.58
LogP:	1.544
LogD:	0.995
LogS:	-2.683
# Rotatable Bonds:	11
TPSA:	160.07
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	4.018
Fsp3:	0.52
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:	-6.211
MDCK Permeability:	7.739024113107007e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.93
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	85.14747619628906%
Volume Distribution (VD):	0.57
Pgp-substrate:	7.9711012840271%

ADMET: Metabolism

CYP1A2-inhibitor:	0.115
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.17
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.098
CYP2D6-substrate:	0.37
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	7.547
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.438
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.468
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.951
Carcinogencity:	0.152
Eye Corrosion:	0.003
Eye Irritation:	0.191
Respiratory Toxicity:	0.11

Download Data

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

Natural Product: NPC469704

Natural Product ID:	NPC469704
*Common Name:**	(2R,3R,4R,5R,6R)-2-[(3S,5R)-5-Hydroxy-1,7-Bis(4-Hydroxyphenyl)Heptan-3-Yl]Oxy-6-(Hydroxymethyl)Oxane-3,4,5-Triol
IUPAC Name:	(2R,3R,4R,5R,6R)-2-[(3S,5R)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	WRUJLWFLDOUUHV-QVQNJILUSA-N
Standard InCHI:	InChI=1S/C25H34O9/c26-14-21-22(30)23(31)24(32)25(34-21)33-20(12-6-16-3-9-18(28)10-4-16)13-19(29)11-5-15-1-7-17(27)8-2-15/h1-4,7-10,19-32H,5-6,11-14H2/t19-,20+,21-,22+,23-,24-,25-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H](C[C@@H](CCc2ccc(cc2)O)O)CCc2ccc(cc2)O)[C@@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1159484
PubChem CID:	46905138
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	floral spikes	n.a.	n.a.	PMID[17346076]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[9873651]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Others	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	16.2	%	PMID[520876]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	14.1	%	PMID[520876]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	27.3	%	PMID[520876]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	74.7	%	PMID[520876]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	1.0	%	PMID[520876]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	56.3	%	PMID[520876]

☑ 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 NPC469704 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	315
0.1-0.2	1243
0.2-0.3	3161
0.3-0.4	9375
0.4-0.5	9969
0.5-0.6	8490
0.6-0.7	7677
0.7-0.8	2164
0.8-0.85	212
0.85-0.9	57
0.9-0.95	29
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC201402
1.0	High Similarity	NPC160854
1.0	High Similarity	NPC469703
0.9912	High Similarity	NPC469686
0.9826	High Similarity	NPC471067
0.9741	High Similarity	NPC178449
0.9741	High Similarity	NPC470907
0.9741	High Similarity	NPC232454
0.9417	High Similarity	NPC264900
0.9417	High Similarity	NPC231607
0.9417	High Similarity	NPC108659
0.9417	High Similarity	NPC79715
0.9417	High Similarity	NPC469687
0.9402	High Similarity	NPC55608
0.9397	High Similarity	NPC282409
0.9397	High Similarity	NPC469702
0.9386	High Similarity	NPC148055
0.9381	High Similarity	NPC157338
0.9333	High Similarity	NPC94179
0.9316	High Similarity	NPC476445
0.9316	High Similarity	NPC469548
0.9316	High Similarity	NPC476448
0.9262	High Similarity	NPC184092
0.9187	High Similarity	NPC17968
0.9187	High Similarity	NPC469705
0.9187	High Similarity	NPC470122
0.9098	High Similarity	NPC288416
0.9052	High Similarity	NPC473556
0.9052	High Similarity	NPC175771
0.9052	High Similarity	NPC301651
0.9043	High Similarity	NPC313193
0.904	High Similarity	NPC471066
0.904	High Similarity	NPC471095
0.904	High Similarity	NPC254275
0.9024	High Similarity	NPC148982
0.9024	High Similarity	NPC158673
0.8968	High Similarity	NPC164172
0.896	High Similarity	NPC235294
0.896	High Similarity	NPC46137
0.896	High Similarity	NPC478255
0.8917	High Similarity	NPC266045
0.8871	High Similarity	NPC225307
0.881	High Similarity	NPC138777
0.881	High Similarity	NPC476407
0.881	High Similarity	NPC246869
0.881	High Similarity	NPC225384
0.878	High Similarity	NPC90318
0.878	High Similarity	NPC83218
0.878	High Similarity	NPC126991
0.876	High Similarity	NPC52277
0.876	High Similarity	NPC177035
0.876	High Similarity	NPC199459
0.871	High Similarity	NPC471157
0.8707	High Similarity	NPC153795
0.8707	High Similarity	NPC290353
0.8707	High Similarity	NPC42911
0.8692	High Similarity	NPC469696
0.8689	High Similarity	NPC52097
0.8689	High Similarity	NPC476142
0.8682	High Similarity	NPC79957
0.8682	High Similarity	NPC263829
0.8651	High Similarity	NPC469549
0.864	High Similarity	NPC106677
0.8618	High Similarity	NPC212176
0.8607	High Similarity	NPC11724
0.8605	High Similarity	NPC34293
0.8605	High Similarity	NPC886
0.8605	High Similarity	NPC476411
0.8605	High Similarity	NPC287597
0.8561	High Similarity	NPC106944
0.856	High Similarity	NPC252114
0.855	High Similarity	NPC470413
0.855	High Similarity	NPC262328
0.855	High Similarity	NPC260425
0.855	High Similarity	NPC138738
0.855	High Similarity	NPC87777
0.8538	High Similarity	NPC123988
0.8538	High Similarity	NPC103398
0.8538	High Similarity	NPC158325
0.8538	High Similarity	NPC180171
0.8527	High Similarity	NPC28637
0.8525	High Similarity	NPC269242
0.8525	High Similarity	NPC476872
0.8525	High Similarity	NPC469412
0.8525	High Similarity	NPC198734
0.8516	High Similarity	NPC475067
0.8496	Intermediate Similarity	NPC472711
0.8492	Intermediate Similarity	NPC471881
0.8492	Intermediate Similarity	NPC471882
0.8492	Intermediate Similarity	NPC156692
0.8492	Intermediate Similarity	NPC45224
0.8492	Intermediate Similarity	NPC173150
0.8492	Intermediate Similarity	NPC35288
0.8485	Intermediate Similarity	NPC476383
0.8485	Intermediate Similarity	NPC328273
0.8485	Intermediate Similarity	NPC472350
0.8485	Intermediate Similarity	NPC64141
0.8485	Intermediate Similarity	NPC81515
0.8485	Intermediate Similarity	NPC205195
0.8485	Intermediate Similarity	NPC68092
0.8485	Intermediate Similarity	NPC171134
0.8485	Intermediate Similarity	NPC321638
0.8485	Intermediate Similarity	NPC197316
0.8485	Intermediate Similarity	NPC321184
0.8485	Intermediate Similarity	NPC89105
0.8473	Intermediate Similarity	NPC471345
0.8462	Intermediate Similarity	NPC187194
0.8462	Intermediate Similarity	NPC169398
0.8462	Intermediate Similarity	NPC35731
0.845	Intermediate Similarity	NPC26080
0.845	Intermediate Similarity	NPC85799
0.845	Intermediate Similarity	NPC165686
0.845	Intermediate Similarity	NPC303422
0.8443	Intermediate Similarity	NPC469708
0.8443	Intermediate Similarity	NPC60589
0.8413	Intermediate Similarity	NPC61181
0.8409	Intermediate Similarity	NPC302583
0.8409	Intermediate Similarity	NPC304152
0.8409	Intermediate Similarity	NPC78363
0.8409	Intermediate Similarity	NPC100558
0.8409	Intermediate Similarity	NPC310252
0.8409	Intermediate Similarity	NPC84789
0.84	Intermediate Similarity	NPC287429
0.8385	Intermediate Similarity	NPC115022
0.8385	Intermediate Similarity	NPC294166
0.8372	Intermediate Similarity	NPC65942
0.8372	Intermediate Similarity	NPC121376
0.8372	Intermediate Similarity	NPC248307
0.8372	Intermediate Similarity	NPC475824
0.837	Intermediate Similarity	NPC185307
0.837	Intermediate Similarity	NPC278961
0.837	Intermediate Similarity	NPC477898
0.837	Intermediate Similarity	NPC46092
0.837	Intermediate Similarity	NPC113680
0.837	Intermediate Similarity	NPC470950
0.8359	Intermediate Similarity	NPC253595
0.8358	Intermediate Similarity	NPC47471
0.8358	Intermediate Similarity	NPC134405
0.8358	Intermediate Similarity	NPC469661
0.8358	Intermediate Similarity	NPC210192
0.8358	Intermediate Similarity	NPC476377
0.8358	Intermediate Similarity	NPC476385
0.8346	Intermediate Similarity	NPC156376
0.8346	Intermediate Similarity	NPC103533
0.8333	Intermediate Similarity	NPC197723
0.8333	Intermediate Similarity	NPC40664
0.8333	Intermediate Similarity	NPC166180
0.8333	Intermediate Similarity	NPC3293
0.8333	Intermediate Similarity	NPC138350
0.8333	Intermediate Similarity	NPC123704
0.8333	Intermediate Similarity	NPC165482
0.8321	Intermediate Similarity	NPC188555
0.8321	Intermediate Similarity	NPC130496
0.8319	Intermediate Similarity	NPC40258
0.8319	Intermediate Similarity	NPC7686
0.8319	Intermediate Similarity	NPC91461
0.8309	Intermediate Similarity	NPC225445
0.8309	Intermediate Similarity	NPC470235
0.8309	Intermediate Similarity	NPC129417
0.8309	Intermediate Similarity	NPC84181
0.8309	Intermediate Similarity	NPC283995
0.8296	Intermediate Similarity	NPC469559
0.8296	Intermediate Similarity	NPC265648
0.8296	Intermediate Similarity	NPC230718
0.8296	Intermediate Similarity	NPC469623
0.8296	Intermediate Similarity	NPC48309
0.8296	Intermediate Similarity	NPC472714
0.8296	Intermediate Similarity	NPC5262
0.8296	Intermediate Similarity	NPC84207
0.8296	Intermediate Similarity	NPC472353
0.8296	Intermediate Similarity	NPC128337
0.8296	Intermediate Similarity	NPC148080
0.8296	Intermediate Similarity	NPC49542
0.8296	Intermediate Similarity	NPC5253
0.8296	Intermediate Similarity	NPC139976
0.8296	Intermediate Similarity	NPC476356
0.8296	Intermediate Similarity	NPC222433
0.8296	Intermediate Similarity	NPC189115
0.8291	Intermediate Similarity	NPC306045
0.8291	Intermediate Similarity	NPC474148
0.8291	Intermediate Similarity	NPC265211
0.8291	Intermediate Similarity	NPC276061
0.8284	Intermediate Similarity	NPC473799
0.8284	Intermediate Similarity	NPC475530
0.8281	Intermediate Similarity	NPC148366
0.8281	Intermediate Similarity	NPC311293
0.8271	Intermediate Similarity	NPC101686
0.8271	Intermediate Similarity	NPC469364
0.8271	Intermediate Similarity	NPC65262
0.8258	Intermediate Similarity	NPC476870
0.8258	Intermediate Similarity	NPC238243
0.825	Intermediate Similarity	NPC473137
0.8248	Intermediate Similarity	NPC279298
0.8248	Intermediate Similarity	NPC38041
0.8248	Intermediate Similarity	NPC272619
0.8248	Intermediate Similarity	NPC18979
0.8248	Intermediate Similarity	NPC475096
0.8248	Intermediate Similarity	NPC22150
0.8248	Intermediate Similarity	NPC286245
0.8235	Intermediate Similarity	NPC478250

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 NPC469704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	745
0.2-0.3	1463
0.3-0.4	3006
0.4-0.5	1967
0.5-0.6	1224
0.6-0.7	438
0.7-0.8	43
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8485	Intermediate Similarity	NPD7266	Discontinued
0.816	Intermediate Similarity	NPD1091	Approved
0.7719	Intermediate Similarity	NPD2859	Approved
0.7719	Intermediate Similarity	NPD2860	Approved
0.7717	Intermediate Similarity	NPD5125	Phase 3
0.7717	Intermediate Similarity	NPD5126	Approved
0.7669	Intermediate Similarity	NPD3027	Phase 3
0.7632	Intermediate Similarity	NPD2934	Approved
0.7632	Intermediate Similarity	NPD2933	Approved
0.763	Intermediate Similarity	NPD1613	Approved
0.763	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD5058	Phase 3
0.7521	Intermediate Similarity	NPD3020	Approved
0.75	Intermediate Similarity	NPD7843	Approved
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7467	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD3022	Approved
0.7398	Intermediate Similarity	NPD3021	Approved
0.7388	Intermediate Similarity	NPD2861	Phase 2
0.7368	Intermediate Similarity	NPD3094	Phase 2
0.7338	Intermediate Similarity	NPD4536	Approved
0.7338	Intermediate Similarity	NPD4538	Approved
0.7338	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4908	Phase 1
0.7333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1610	Phase 2
0.7324	Intermediate Similarity	NPD6674	Discontinued
0.7323	Intermediate Similarity	NPD7157	Approved
0.7317	Intermediate Similarity	NPD2684	Approved
0.7287	Intermediate Similarity	NPD1548	Phase 1
0.7286	Intermediate Similarity	NPD5960	Phase 3
0.7286	Intermediate Similarity	NPD5588	Approved
0.7279	Intermediate Similarity	NPD1653	Approved
0.7259	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD846	Approved
0.725	Intermediate Similarity	NPD940	Approved
0.7226	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6190	Approved
0.7218	Intermediate Similarity	NPD4659	Approved
0.7214	Intermediate Similarity	NPD7097	Phase 1
0.7197	Intermediate Similarity	NPD3092	Approved
0.7176	Intermediate Similarity	NPD6516	Phase 2
0.7176	Intermediate Similarity	NPD5846	Approved
0.7174	Intermediate Similarity	NPD6407	Approved
0.7174	Intermediate Similarity	NPD6405	Approved
0.7167	Intermediate Similarity	NPD1242	Phase 1
0.7152	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4103	Phase 2
0.7107	Intermediate Similarity	NPD7074	Phase 3
0.7089	Intermediate Similarity	NPD7228	Approved
0.7083	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3705	Approved
0.7067	Intermediate Similarity	NPD4380	Phase 2
0.7063	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6233	Phase 2
0.7044	Intermediate Similarity	NPD7054	Approved
0.7037	Intermediate Similarity	NPD8651	Approved
0.7034	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3028	Approved
0.7023	Intermediate Similarity	NPD3091	Approved
0.7016	Intermediate Similarity	NPD968	Approved
0.7	Intermediate Similarity	NPD7472	Approved
0.6984	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3818	Discontinued
0.6978	Remote Similarity	NPD6798	Discontinued
0.6974	Remote Similarity	NPD37	Approved
0.697	Remote Similarity	NPD1357	Approved
0.6968	Remote Similarity	NPD6234	Discontinued
0.696	Remote Similarity	NPD290	Approved
0.695	Remote Similarity	NPD4340	Discontinued
0.6948	Remote Similarity	NPD4965	Approved
0.6948	Remote Similarity	NPD4967	Phase 2
0.6948	Remote Similarity	NPD4966	Approved
0.6923	Remote Similarity	NPD4108	Discontinued
0.6918	Remote Similarity	NPD4628	Phase 3
0.6914	Remote Similarity	NPD7251	Discontinued
0.6914	Remote Similarity	NPD6559	Discontinued
0.6901	Remote Similarity	NPD5314	Approved
0.6892	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2562	Approved
0.6889	Remote Similarity	NPD2561	Approved
0.6884	Remote Similarity	NPD5736	Approved
0.6879	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD3059	Approved
0.6879	Remote Similarity	NPD3062	Approved
0.6879	Remote Similarity	NPD3061	Approved
0.6875	Remote Similarity	NPD969	Suspended
0.6871	Remote Similarity	NPD7808	Phase 3
0.6857	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6797	Phase 2
0.6849	Remote Similarity	NPD1652	Phase 2
0.6842	Remote Similarity	NPD111	Approved
0.6838	Remote Similarity	NPD6582	Phase 2
0.6838	Remote Similarity	NPD3685	Discontinued
0.6838	Remote Similarity	NPD6583	Phase 3
0.6831	Remote Similarity	NPD6355	Discontinued
0.6822	Remote Similarity	NPD5535	Approved
0.6815	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7685	Pre-registration
0.6806	Remote Similarity	NPD7033	Discontinued
0.6803	Remote Similarity	NPD4535	Phase 3
0.6795	Remote Similarity	NPD7075	Discontinued
0.6794	Remote Similarity	NPD6671	Approved
0.6791	Remote Similarity	NPD3095	Discontinued
0.6791	Remote Similarity	NPD9384	Approved
0.6791	Remote Similarity	NPD9381	Approved
0.6786	Remote Similarity	NPD7095	Approved
0.6769	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5283	Phase 1
0.6768	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7741	Discontinued
0.6744	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD228	Approved
0.6738	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3764	Approved
0.6731	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8312	Approved
0.6727	Remote Similarity	NPD8313	Approved
0.6719	Remote Similarity	NPD4750	Phase 3
0.6719	Remote Similarity	NPD5451	Approved
0.6713	Remote Similarity	NPD5124	Phase 1
0.6713	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5735	Approved
0.6712	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.671	Remote Similarity	NPD2977	Approved
0.671	Remote Similarity	NPD2978	Approved
0.6707	Remote Similarity	NPD7240	Approved
0.6694	Remote Similarity	NPD1809	Phase 2
0.6694	Remote Similarity	NPD844	Approved
0.6692	Remote Similarity	NPD856	Approved
0.6692	Remote Similarity	NPD7635	Approved
0.6692	Remote Similarity	NPD16	Approved
0.6691	Remote Similarity	NPD6584	Phase 3
0.669	Remote Similarity	NPD6663	Approved
0.669	Remote Similarity	NPD4062	Phase 3
0.6689	Remote Similarity	NPD3400	Discontinued
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD4625	Phase 3
0.6667	Remote Similarity	NPD7212	Phase 2
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD2568	Approved
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD7213	Phase 3
0.6667	Remote Similarity	NPD7199	Phase 2
0.6645	Remote Similarity	NPD1934	Approved
0.6643	Remote Similarity	NPD3620	Phase 2
0.6643	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD9545	Approved
0.6641	Remote Similarity	NPD2228	Approved
0.6641	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2234	Approved
0.6641	Remote Similarity	NPD2229	Approved
0.6623	Remote Similarity	NPD3536	Discontinued
0.6623	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7447	Phase 1
0.6619	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3847	Discontinued
0.6613	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5763	Approved
0.6599	Remote Similarity	NPD5762	Approved
0.6594	Remote Similarity	NPD7876	Discontinued
0.6594	Remote Similarity	NPD9622	Approved
0.6594	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD2983	Phase 2
0.6594	Remote Similarity	NPD4749	Approved
0.6594	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD2982	Phase 2
0.6591	Remote Similarity	NPD2629	Approved
0.6582	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD422	Phase 1
0.6569	Remote Similarity	NPD1535	Discovery
0.6567	Remote Similarity	NPD317	Approved
0.6567	Remote Similarity	NPD318	Approved
0.6562	Remote Similarity	NPD2342	Discontinued
0.6562	Remote Similarity	NPD1358	Approved
0.6558	Remote Similarity	NPD6056	Approved
0.6558	Remote Similarity	NPD6057	Approved
0.6554	Remote Similarity	NPD2424	Discontinued
0.6552	Remote Similarity	NPD817	Approved
0.6552	Remote Similarity	NPD6653	Approved
0.6552	Remote Similarity	NPD3054	Approved
0.6552	Remote Similarity	NPD3052	Approved
0.6552	Remote Similarity	NPD823	Approved
0.655	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD3179	Approved
0.6549	Remote Similarity	NPD3180	Approved
0.6548	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6168	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