NPASS Compound

Structure

NPC469702 OpenBabel07101719152D 32 34 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 -2.5981 -1.5000 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 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0875 3.6160 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 -2.5981 -0.5000 0.0000 C 0 0 2 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 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 4.1808 1.8364 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 3.5116 1.0933 0.0000 C 0 0 1 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 2.5981 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 5.0820 3.7205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1753 1.7319 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 3.7195 0.1151 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 1.0000 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 2.7026 2.4945 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 2 3 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 6 1 0 0 0 0 4 11 2 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 22 1 0 0 0 0 9 29 1 0 0 0 0 10 1 1 1 0 0 0 10 30 1 0 0 0 0 12 23 1 0 0 0 0 13 8 1 6 0 0 0 13 15 1 0 0 0 0 13 31 1 0 0 0 0 14 9 1 6 0 0 0 14 16 1 0 0 0 0 14 32 1 0 0 0 0 15 18 1 0 0 0 0 15 24 1 1 0 0 0 16 17 1 0 0 0 0 16 25 1 6 0 0 0 17 19 1 0 0 0 0 17 26 1 1 0 0 0 18 20 1 0 0 0 0 18 27 1 6 0 0 0 19 21 1 0 0 0 0 19 28 1 1 0 0 0 20 29 1 6 0 0 0 20 31 1 0 0 0 0 21 30 1 6 0 0 0 21 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.19
Volume:	434.886
LogP:	-0.537
LogD:	-0.794
LogS:	-1.791
# Rotatable Bonds:	9
TPSA:	178.53
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	4.341
Fsp3:	0.714
Lipinski Rule-of-5:	Rejected
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:	-6.274
MDCK Permeability:	5.095778396935202e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.846
Human Intestinal Absorption (HIA):	0.929
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128
Plasma Protein Binding (PPB):	60.73296356201172%
Volume Distribution (VD):	0.289
Pgp-substrate:	27.145217895507812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.294
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.05

ADMET: Excretion

Clearance (CL):	1.145
Half-life (T1/2):	0.774

ADMET: Toxicity

hERG Blockers:	0.209
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.527
Rat Oral Acute Toxicity:	0.235
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.908
Carcinogencity:	0.071
Eye Corrosion:	0.003
Eye Irritation:	0.128
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC469702

Natural Product ID:	NPC469702
*Common Name:**	2-(3,4-Dihydroxy-5-Hydroxymethyl-Tetrahydro-Furan-2-Yloxymethyl)-6-[3-(4-Hydroxy-Phenyl)-1-Methyl-Propoxy]-Tetrahydro-Pyran-3,4,5-Triol
IUPAC Name:	(2R,3R,4R,5R,6R)-2-[[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]oxyoxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	DJDISCKFJXDADJ-LCIFOZHJSA-N
Standard InCHI:	InChI=1S/C21H32O11/c1-10(2-3-11-4-6-12(23)7-5-11)30-21-19(28)17(26)16(25)14(32-21)9-29-20-18(27)15(24)13(8-22)31-20/h4-7,10,13-28H,2-3,8-9H2,1H3/t10-,13-,14-,15-,16+,17-,18+,19-,20-,21-/m1/s1
SMILES:	CC(CCC1=CC=C(C=C1)O)OC2C(C(C(C(O2)COC3C(C(C(O3)CO)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1159482
PubChem CID:	46905136
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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	=	3.4	%	PMID[557078]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	6.2	%	PMID[557078]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	7.5	%	PMID[557078]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	6.8	%	PMID[557078]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	5.1	%	PMID[557078]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	98.2	%	PMID[557078]

☑ 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 NPC469702 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	239
0.1-0.2	1097
0.2-0.3	2873
0.3-0.4	8361
0.4-0.5	10913
0.5-0.6	10249
0.6-0.7	7188
0.7-0.8	1562
0.8-0.85	157
0.85-0.9	38
0.9-0.95	15
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC282409
0.9912	High Similarity	NPC476448
0.9912	High Similarity	NPC469548
0.9912	High Similarity	NPC476445
0.9643	High Similarity	NPC148055
0.9569	High Similarity	NPC471067
0.9487	High Similarity	NPC178449
0.9487	High Similarity	NPC470907
0.9487	High Similarity	NPC232454
0.9483	High Similarity	NPC55608
0.9464	High Similarity	NPC157338
0.9397	High Similarity	NPC469704
0.9397	High Similarity	NPC201402
0.9397	High Similarity	NPC160854
0.9397	High Similarity	NPC469703
0.9316	High Similarity	NPC469686
0.9174	High Similarity	NPC469687
0.9167	High Similarity	NPC90318
0.913	High Similarity	NPC175771
0.9123	High Similarity	NPC313193
0.9016	High Similarity	NPC35288
0.9016	High Similarity	NPC471881
0.9016	High Similarity	NPC45224
0.9016	High Similarity	NPC156692
0.9016	High Similarity	NPC173150
0.9016	High Similarity	NPC471882
0.8992	High Similarity	NPC266045
0.8934	High Similarity	NPC61181
0.888	High Similarity	NPC478255
0.8871	High Similarity	NPC469549
0.8862	High Similarity	NPC264900
0.8862	High Similarity	NPC108659
0.8862	High Similarity	NPC79715
0.8862	High Similarity	NPC231607
0.8862	High Similarity	NPC103533
0.881	High Similarity	NPC471095
0.881	High Similarity	NPC471066
0.879	High Similarity	NPC225307
0.878	High Similarity	NPC94179
0.877	High Similarity	NPC287429
0.876	High Similarity	NPC476142
0.876	High Similarity	NPC52097
0.874	High Similarity	NPC164172
0.873	High Similarity	NPC235294
0.873	High Similarity	NPC46137
0.872	High Similarity	NPC184092
0.871	High Similarity	NPC106677
0.871	High Similarity	NPC288416
0.8689	High Similarity	NPC212176
0.8678	High Similarity	NPC11724
0.8672	High Similarity	NPC470881
0.8651	High Similarity	NPC17968
0.8651	High Similarity	NPC469705
0.8651	High Similarity	NPC470122
0.864	High Similarity	NPC148982
0.8629	High Similarity	NPC471157
0.8595	High Similarity	NPC198734
0.8595	High Similarity	NPC476872
0.8595	High Similarity	NPC269242
0.8595	High Similarity	NPC469412
0.8594	High Similarity	NPC6836
0.8583	High Similarity	NPC138777
0.8583	High Similarity	NPC65942
0.8583	High Similarity	NPC246869
0.8583	High Similarity	NPC281798
0.8583	High Similarity	NPC225384
0.8583	High Similarity	NPC248307
0.8548	High Similarity	NPC126991
0.8548	High Similarity	NPC470510
0.8548	High Similarity	NPC83218
0.8527	High Similarity	NPC471883
0.8527	High Similarity	NPC169398
0.8527	High Similarity	NPC35731
0.8516	High Similarity	NPC252833
0.8516	High Similarity	NPC254275
0.8512	High Similarity	NPC60589
0.8512	High Similarity	NPC469708
0.8492	Intermediate Similarity	NPC158673
0.8487	Intermediate Similarity	NPC301651
0.8487	Intermediate Similarity	NPC473556
0.848	Intermediate Similarity	NPC252114
0.8473	Intermediate Similarity	NPC469696
0.8462	Intermediate Similarity	NPC263829
0.845	Intermediate Similarity	NPC254398
0.845	Intermediate Similarity	NPC25821
0.845	Intermediate Similarity	NPC28637
0.8448	Intermediate Similarity	NPC264784
0.8438	Intermediate Similarity	NPC475824
0.8438	Intermediate Similarity	NPC219677
0.8425	Intermediate Similarity	NPC307110
0.8421	Intermediate Similarity	NPC472711
0.8409	Intermediate Similarity	NPC328273
0.8409	Intermediate Similarity	NPC321184
0.8409	Intermediate Similarity	NPC321638
0.8409	Intermediate Similarity	NPC171134
0.8407	Intermediate Similarity	NPC47286
0.84	Intermediate Similarity	NPC123704
0.8397	Intermediate Similarity	NPC52277
0.8397	Intermediate Similarity	NPC177035
0.8397	Intermediate Similarity	NPC199459
0.8372	Intermediate Similarity	NPC473924
0.8359	Intermediate Similarity	NPC472024
0.8359	Intermediate Similarity	NPC80600
0.8333	Intermediate Similarity	NPC469364
0.8333	Intermediate Similarity	NPC470413
0.8333	Intermediate Similarity	NPC101686
0.8333	Intermediate Similarity	NPC304152
0.8333	Intermediate Similarity	NPC138738
0.8333	Intermediate Similarity	NPC65262
0.8333	Intermediate Similarity	NPC195196
0.8296	Intermediate Similarity	NPC477898
0.8296	Intermediate Similarity	NPC185307
0.8296	Intermediate Similarity	NPC46092
0.8296	Intermediate Similarity	NPC470950
0.8295	Intermediate Similarity	NPC254819
0.8295	Intermediate Similarity	NPC476407
0.8291	Intermediate Similarity	NPC30563
0.8281	Intermediate Similarity	NPC248355
0.8281	Intermediate Similarity	NPC26653
0.8281	Intermediate Similarity	NPC166040
0.8281	Intermediate Similarity	NPC270849
0.8281	Intermediate Similarity	NPC229784
0.8281	Intermediate Similarity	NPC253595
0.8281	Intermediate Similarity	NPC97326
0.8281	Intermediate Similarity	NPC477293
0.8281	Intermediate Similarity	NPC477294
0.8279	Intermediate Similarity	NPC477803
0.8271	Intermediate Similarity	NPC472350
0.8271	Intermediate Similarity	NPC197316
0.8271	Intermediate Similarity	NPC81515
0.8271	Intermediate Similarity	NPC476383
0.8271	Intermediate Similarity	NPC89105
0.8271	Intermediate Similarity	NPC64141
0.8271	Intermediate Similarity	NPC68092
0.8264	Intermediate Similarity	NPC476266
0.8244	Intermediate Similarity	NPC886
0.8244	Intermediate Similarity	NPC187194
0.8244	Intermediate Similarity	NPC107478
0.8244	Intermediate Similarity	NPC287597
0.8244	Intermediate Similarity	NPC34293
0.8235	Intermediate Similarity	NPC296954
0.8235	Intermediate Similarity	NPC141455
0.8235	Intermediate Similarity	NPC129417
0.8235	Intermediate Similarity	NPC84181
0.8235	Intermediate Similarity	NPC470235
0.8235	Intermediate Similarity	NPC283995
0.8235	Intermediate Similarity	NPC300894
0.8235	Intermediate Similarity	NPC196063
0.8231	Intermediate Similarity	NPC473285
0.8226	Intermediate Similarity	NPC226712
0.8222	Intermediate Similarity	NPC476356
0.8217	Intermediate Similarity	NPC262606
0.8217	Intermediate Similarity	NPC474491
0.8205	Intermediate Similarity	NPC474148
0.8205	Intermediate Similarity	NPC276061
0.8203	Intermediate Similarity	NPC302378
0.8203	Intermediate Similarity	NPC232880
0.8195	Intermediate Similarity	NPC476376
0.8195	Intermediate Similarity	NPC260425
0.8195	Intermediate Similarity	NPC87777
0.8195	Intermediate Similarity	NPC262328
0.8182	Intermediate Similarity	NPC184938
0.8182	Intermediate Similarity	NPC101624
0.8182	Intermediate Similarity	NPC79957
0.8182	Intermediate Similarity	NPC123988
0.8175	Intermediate Similarity	NPC22150
0.8175	Intermediate Similarity	NPC38041
0.8175	Intermediate Similarity	NPC279298
0.8175	Intermediate Similarity	NPC18979
0.8174	Intermediate Similarity	NPC152384
0.8174	Intermediate Similarity	NPC37714
0.8168	Intermediate Similarity	NPC294166
0.8168	Intermediate Similarity	NPC132895
0.8168	Intermediate Similarity	NPC115022
0.8162	Intermediate Similarity	NPC105005
0.8162	Intermediate Similarity	NPC40305
0.8162	Intermediate Similarity	NPC478250
0.8154	Intermediate Similarity	NPC9912
0.8154	Intermediate Similarity	NPC475067
0.8151	Intermediate Similarity	NPC290353
0.8151	Intermediate Similarity	NPC153795
0.8151	Intermediate Similarity	NPC42911
0.8148	Intermediate Similarity	NPC476377
0.8148	Intermediate Similarity	NPC47471
0.8148	Intermediate Similarity	NPC134405
0.8148	Intermediate Similarity	NPC476385
0.814	Intermediate Similarity	NPC295970
0.8134	Intermediate Similarity	NPC205195
0.8134	Intermediate Similarity	NPC49597
0.8134	Intermediate Similarity	NPC220942
0.8134	Intermediate Similarity	NPC226005
0.8134	Intermediate Similarity	NPC156376
0.8125	Intermediate Similarity	NPC262826
0.8125	Intermediate Similarity	NPC198798
0.8125	Intermediate Similarity	NPC476873
0.812	Intermediate Similarity	NPC470572
0.812	Intermediate Similarity	NPC471345
0.812	Intermediate Similarity	NPC165482
0.812	Intermediate Similarity	NPC138350
0.812	Intermediate Similarity	NPC3293

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 NPC469702 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	693
0.2-0.3	1474
0.3-0.4	3051
0.4-0.5	2054
0.5-0.6	1268
0.6-0.7	370
0.7-0.8	26
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8271	Intermediate Similarity	NPD7266	Discontinued
0.8226	Intermediate Similarity	NPD1091	Approved
0.7638	Intermediate Similarity	NPD5126	Approved
0.7638	Intermediate Similarity	NPD5125	Phase 3
0.7561	Intermediate Similarity	NPD7843	Approved
0.7544	Intermediate Similarity	NPD2934	Approved
0.7544	Intermediate Similarity	NPD2933	Approved
0.7519	Intermediate Similarity	NPD3705	Approved
0.7478	Intermediate Similarity	NPD2859	Approved
0.7478	Intermediate Similarity	NPD2860	Approved
0.7465	Intermediate Similarity	NPD5058	Phase 3
0.7463	Intermediate Similarity	NPD3027	Phase 3
0.7422	Intermediate Similarity	NPD1357	Approved
0.7381	Intermediate Similarity	NPD7157	Approved
0.7377	Intermediate Similarity	NPD2684	Approved
0.7311	Intermediate Similarity	NPD846	Approved
0.7311	Intermediate Similarity	NPD940	Approved
0.7293	Intermediate Similarity	NPD3094	Phase 2
0.7288	Intermediate Similarity	NPD3020	Approved
0.7211	Intermediate Similarity	NPD1653	Approved
0.72	Intermediate Similarity	NPD969	Suspended
0.7177	Intermediate Similarity	NPD3022	Approved
0.7177	Intermediate Similarity	NPD3021	Approved
0.7174	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1613	Approved
0.7154	Intermediate Similarity	NPD290	Approved
0.7143	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6674	Discontinued
0.7121	Intermediate Similarity	NPD3092	Approved
0.7099	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5588	Approved
0.7086	Intermediate Similarity	NPD8455	Phase 2
0.7059	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2861	Phase 2
0.7054	Intermediate Similarity	NPD111	Approved
0.704	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7228	Approved
0.7021	Intermediate Similarity	NPD4536	Approved
0.7021	Intermediate Similarity	NPD4538	Approved
0.7021	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7097	Phase 1
0.7007	Intermediate Similarity	NPD4908	Phase 1
0.6963	Remote Similarity	NPD8651	Approved
0.6947	Remote Similarity	NPD3091	Approved
0.6947	Remote Similarity	NPD1548	Phase 1
0.6942	Remote Similarity	NPD3028	Approved
0.6942	Remote Similarity	NPD1242	Phase 1
0.6929	Remote Similarity	NPD228	Approved
0.6918	Remote Similarity	NPD6190	Approved
0.6908	Remote Similarity	NPD37	Approved
0.6906	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6234	Discontinued
0.6897	Remote Similarity	NPD1652	Phase 2
0.6889	Remote Similarity	NPD3685	Discontinued
0.6889	Remote Similarity	NPD4659	Approved
0.6884	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4967	Phase 2
0.6883	Remote Similarity	NPD4965	Approved
0.6883	Remote Similarity	NPD4966	Approved
0.6875	Remote Similarity	NPD7054	Approved
0.6875	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.687	Remote Similarity	NPD856	Approved
0.687	Remote Similarity	NPD16	Approved
0.6866	Remote Similarity	NPD1610	Phase 2
0.6863	Remote Similarity	NPD2978	Approved
0.6863	Remote Similarity	NPD2977	Approved
0.6857	Remote Similarity	NPD6405	Approved
0.6857	Remote Similarity	NPD6233	Phase 2
0.6857	Remote Similarity	NPD6407	Approved
0.6853	Remote Similarity	NPD5960	Phase 3
0.6852	Remote Similarity	NPD6559	Discontinued
0.6846	Remote Similarity	NPD6671	Approved
0.6842	Remote Similarity	NPD9381	Approved
0.6842	Remote Similarity	NPD9384	Approved
0.6832	Remote Similarity	NPD7074	Phase 3
0.6832	Remote Similarity	NPD7472	Approved
0.6831	Remote Similarity	NPD6653	Approved
0.6824	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD9545	Approved
0.6815	Remote Similarity	NPD2561	Approved
0.6815	Remote Similarity	NPD2562	Approved
0.6813	Remote Similarity	NPD3818	Discontinued
0.6812	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD5736	Approved
0.68	Remote Similarity	NPD968	Approved
0.6797	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4103	Phase 2
0.6788	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4750	Phase 3
0.6765	Remote Similarity	NPD9622	Approved
0.6761	Remote Similarity	NPD6355	Discontinued
0.675	Remote Similarity	NPD1809	Phase 2
0.675	Remote Similarity	NPD844	Approved
0.6748	Remote Similarity	NPD7685	Pre-registration
0.6748	Remote Similarity	NPD7251	Discontinued
0.6746	Remote Similarity	NPD1358	Approved
0.6742	Remote Similarity	NPD318	Approved
0.6742	Remote Similarity	NPD317	Approved
0.6741	Remote Similarity	NPD422	Phase 1
0.6735	Remote Similarity	NPD4628	Phase 3
0.6723	Remote Similarity	NPD845	Approved
0.6716	Remote Similarity	NPD3095	Discontinued
0.6716	Remote Similarity	NPD5846	Approved
0.6716	Remote Similarity	NPD6516	Phase 2
0.6714	Remote Similarity	NPD3180	Approved
0.6714	Remote Similarity	NPD3179	Approved
0.6713	Remote Similarity	NPD5314	Approved
0.6712	Remote Similarity	NPD2424	Discontinued
0.6707	Remote Similarity	NPD7808	Phase 3
0.6692	Remote Similarity	NPD7741	Discontinued
0.669	Remote Similarity	NPD3062	Approved
0.669	Remote Similarity	NPD4060	Phase 1
0.669	Remote Similarity	NPD3059	Approved
0.669	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3061	Approved
0.6687	Remote Similarity	NPD6797	Phase 2
0.6667	Remote Similarity	NPD4236	Phase 3
0.6667	Remote Similarity	NPD4237	Approved
0.6667	Remote Similarity	NPD4380	Phase 2
0.6667	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6798	Discontinued
0.6646	Remote Similarity	NPD7240	Approved
0.6644	Remote Similarity	NPD5762	Approved
0.6644	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5763	Approved
0.6643	Remote Similarity	NPD4340	Discontinued
0.6643	Remote Similarity	NPD5124	Phase 1
0.6643	Remote Similarity	NPD5735	Approved
0.6643	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4108	Discontinued
0.6621	Remote Similarity	NPD7033	Discontinued
0.662	Remote Similarity	NPD6663	Approved
0.662	Remote Similarity	NPD4062	Phase 3
0.6619	Remote Similarity	NPD9619	Approved
0.6619	Remote Similarity	NPD9621	Approved
0.6619	Remote Similarity	NPD9620	Approved
0.6618	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD821	Approved
0.6604	Remote Similarity	NPD7199	Phase 2
0.6597	Remote Similarity	NPD2568	Approved
0.6589	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3620	Phase 2
0.6573	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD2229	Approved
0.6565	Remote Similarity	NPD2228	Approved
0.6565	Remote Similarity	NPD2234	Approved
0.6565	Remote Similarity	NPD5283	Phase 1
0.6557	Remote Similarity	NPD288	Approved
0.6556	Remote Similarity	NPD3536	Discontinued
0.6556	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD598	Approved
0.6549	Remote Similarity	NPD3764	Approved
0.6549	Remote Similarity	NPD597	Approved
0.6549	Remote Similarity	NPD601	Approved
0.6547	Remote Similarity	NPD1134	Approved
0.6547	Remote Similarity	NPD1131	Approved
0.6547	Remote Similarity	NPD1129	Approved
0.6547	Remote Similarity	NPD1133	Approved
0.6547	Remote Similarity	NPD1135	Approved
0.6547	Remote Similarity	NPD6362	Approved
0.6547	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5773	Approved
0.6538	Remote Similarity	NPD5772	Approved
0.6535	Remote Similarity	NPD3134	Approved
0.6531	Remote Similarity	NPD1375	Discontinued
0.6531	Remote Similarity	NPD6002	Phase 3
0.6531	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6005	Phase 3
0.6531	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6004	Phase 3
0.6528	Remote Similarity	NPD230	Phase 1
0.6522	Remote Similarity	NPD6583	Phase 3
0.6522	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6582	Phase 2
0.6522	Remote Similarity	NPD2983	Phase 2
0.6522	Remote Similarity	NPD2982	Phase 2
0.6522	Remote Similarity	NPD4749	Approved
0.6519	Remote Similarity	NPD7075	Discontinued
0.6515	Remote Similarity	NPD9614	Approved
0.6515	Remote Similarity	NPD9618	Approved
0.6515	Remote Similarity	NPD2629	Approved
0.651	Remote Similarity	NPD4535	Phase 3
0.6508	Remote Similarity	NPD9608	Approved
0.6508	Remote Similarity	NPD9610	Approved
0.6506	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1130	Approved
0.6503	Remote Similarity	NPD1132	Approved
0.6503	Remote Similarity	NPD1136	Approved
0.65	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5647	Approved
0.6489	Remote Similarity	NPD7635	Approved
0.6489	Remote Similarity	NPD5535	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