NPASS Compound

Structure

CID90318 OpenBabel06191715432D 31 33 0 0 1 0 0 0 0 0999 V2000 7.8988 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 1.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8366 3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7026 4.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5686 3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5686 2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2007 0.8392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6308 4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3917 0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 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 2.7026 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 4 1 0 0 0 0 3 9 1 0 0 0 0 4 28 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 29 1 0 0 0 0 7 19 1 0 0 0 0 7 20 1 0 0 0 0 8 19 1 0 0 0 0 8 30 1 0 0 0 0 10 11 2 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 6 1 6 0 0 0 12 13 1 0 0 0 0 12 31 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 1 0 0 0 14 15 1 0 0 0 0 14 24 1 6 0 0 0 15 17 1 0 0 0 0 15 25 1 1 0 0 0 16 18 1 0 0 0 0 16 19 1 1 0 0 0 16 26 1 0 0 0 0 17 28 1 6 0 0 0 17 31 1 0 0 0 0 18 29 1 6 0 0 0 18 30 1 0 0 0 0 19 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.16
Volume:	409.084
LogP:	-1.449
LogD:	-1.041
LogS:	-1.271
# Rotatable Bonds:	8
TPSA:	198.76
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.187
Synthetic Accessibility Score:	4.46
Fsp3:	0.684
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.463
MDCK Permeability:	1.6461332052131183e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.818
Human Intestinal Absorption (HIA):	0.992
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	45.48816680908203%
Volume Distribution (VD):	0.325
Pgp-substrate:	54.106170654296875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.024

ADMET: Excretion

Clearance (CL):	1.255
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.227
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.374
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.944
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.085
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC90318

Natural Product ID:	NPC90318
*Common Name:**	2-(3,4-Dihydroxyphenyl)Ethanol 1-O-[Beta-D-Apiofuranosyl-(1-6)-Beta-D-Glucopyranoside]
IUPAC Name:	(2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	LBHKVQMODMELAS-OTCFHACESA-N
Standard InCHI:	InChI=1S/C19H28O12/c20-7-19(27)8-30-18(16(19)26)29-6-12-13(23)14(24)15(25)17(31-12)28-4-3-9-1-2-10(21)11(22)5-9/h1-2,5,12-18,20-27H,3-4,6-8H2/t12-,13-,14+,15-,16+,17-,18-,19-/m1/s1
SMILES:	c1cc(c(cc1CCO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@@](CO)(CO2)O)O)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376387
PubChem CID:	11503277
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17461599]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	stem	n.a.	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	Stem bark	Lu Mountain, Jiangxi Province, China	2004-AUG	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26697686]
NPO10994	Sargentodoxa cuneata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10994	Sargentodoxa cuneata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10994	Sargentodoxa cuneata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10994	Sargentodoxa cuneata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10994	Sargentodoxa cuneata	Species	Lardizabalaceae	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	6
Others	1

Activity Type	# Activity
Cell Line	3
Others	3
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	5000.0	nM	PMID[570229]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	5000.0	nM	PMID[570229]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5000.0	nM	PMID[570229]
NPT2	Others	Unspecified		Inhibition	=	28.8	%	PMID[570229]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	900.0	nM	PMID[570229]
NPT27	Others	Unspecified		IC50	>	5000.0	nM	PMID[570229]

☑ 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 NPC90318 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	1260
0.2-0.3	3322
0.3-0.4	9037
0.4-0.5	10318
0.5-0.6	9143
0.6-0.7	6759
0.7-0.8	2122
0.8-0.85	312
0.85-0.9	68
0.9-0.95	17
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9661	High Similarity	NPC266045
0.935	High Similarity	NPC264900
0.935	High Similarity	NPC108659
0.935	High Similarity	NPC231607
0.935	High Similarity	NPC79715
0.9291	High Similarity	NPC470881
0.9274	High Similarity	NPC148982
0.9268	High Similarity	NPC94179
0.925	High Similarity	NPC469548
0.925	High Similarity	NPC476445
0.925	High Similarity	NPC476448
0.9213	High Similarity	NPC6836
0.92	High Similarity	NPC184092
0.9167	High Similarity	NPC469702
0.9167	High Similarity	NPC282409
0.9134	High Similarity	NPC252833
0.9134	High Similarity	NPC473924
0.9062	High Similarity	NPC254398
0.9055	High Similarity	NPC219677
0.9055	High Similarity	NPC65942
0.9055	High Similarity	NPC248307
0.9024	High Similarity	NPC232454
0.9024	High Similarity	NPC178449
0.9024	High Similarity	NPC470907
0.9008	High Similarity	NPC321184
0.9008	High Similarity	NPC171134
0.9008	High Similarity	NPC321638
0.9008	High Similarity	NPC328273
0.8992	High Similarity	NPC148055
0.8984	High Similarity	NPC254275
0.8983	High Similarity	NPC157338
0.8943	High Similarity	NPC471067
0.8915	High Similarity	NPC25821
0.8898	High Similarity	NPC477293
0.8898	High Similarity	NPC477294
0.8898	High Similarity	NPC229784
0.8898	High Similarity	NPC307110
0.8846	High Similarity	NPC886
0.8846	High Similarity	NPC287597
0.8846	High Similarity	NPC35731
0.8846	High Similarity	NPC471883
0.8846	High Similarity	NPC34293
0.8819	High Similarity	NPC232880
0.8788	High Similarity	NPC304152
0.8788	High Similarity	NPC195196
0.878	High Similarity	NPC160854
0.878	High Similarity	NPC201402
0.878	High Similarity	NPC469703
0.878	High Similarity	NPC469704
0.8779	High Similarity	NPC123988
0.877	High Similarity	NPC477803
0.8741	High Similarity	NPC105005
0.8741	High Similarity	NPC46092
0.8741	High Similarity	NPC40305
0.874	High Similarity	NPC469687
0.874	High Similarity	NPC476873
0.8731	High Similarity	NPC472711
0.8712	High Similarity	NPC52277
0.8712	High Similarity	NPC199459
0.8712	High Similarity	NPC177035
0.8712	High Similarity	NPC470572
0.871	High Similarity	NPC469686
0.871	High Similarity	NPC55608
0.8702	High Similarity	NPC107478
0.8692	High Similarity	NPC473285
0.8682	High Similarity	NPC472024
0.8682	High Similarity	NPC80600
0.8678	High Similarity	NPC175771
0.8676	High Similarity	NPC283995
0.8676	High Similarity	NPC84181
0.8676	High Similarity	NPC129417
0.8676	High Similarity	NPC300894
0.8676	High Similarity	NPC141455
0.8676	High Similarity	NPC196063
0.8676	High Similarity	NPC470235
0.8676	High Similarity	NPC296954
0.8667	High Similarity	NPC313193
0.8647	High Similarity	NPC302583
0.8647	High Similarity	NPC470413
0.8647	High Similarity	NPC78363
0.8647	High Similarity	NPC100558
0.8647	High Similarity	NPC260425
0.8647	High Similarity	NPC84789
0.8647	High Similarity	NPC138738
0.8647	High Similarity	NPC310252
0.8636	High Similarity	NPC103398
0.8636	High Similarity	NPC184938
0.8636	High Similarity	NPC158325
0.8636	High Similarity	NPC101624
0.8636	High Similarity	NPC180171
0.8626	High Similarity	NPC132895
0.8615	High Similarity	NPC9912
0.8613	High Similarity	NPC469586
0.8613	High Similarity	NPC18979
0.8605	High Similarity	NPC248355
0.8605	High Similarity	NPC26653
0.8605	High Similarity	NPC166040
0.8605	High Similarity	NPC270849
0.8603	High Similarity	NPC477898
0.8603	High Similarity	NPC185307
0.8603	High Similarity	NPC470950
0.8582	High Similarity	NPC64141
0.8582	High Similarity	NPC476383
0.8582	High Similarity	NPC81515
0.8582	High Similarity	NPC197316
0.8582	High Similarity	NPC226005
0.8582	High Similarity	NPC89105
0.8582	High Similarity	NPC472350
0.8582	High Similarity	NPC205195
0.8582	High Similarity	NPC220942
0.8582	High Similarity	NPC68092
0.8571	High Similarity	NPC473451
0.8551	High Similarity	NPC112861
0.8551	High Similarity	NPC229505
0.855	High Similarity	NPC470270
0.8529	High Similarity	NPC476356
0.8527	High Similarity	NPC302378
0.8519	High Similarity	NPC106944
0.8507	High Similarity	NPC477798
0.8507	High Similarity	NPC477797
0.8507	High Similarity	NPC476376
0.8504	High Similarity	NPC287429
0.8496	Intermediate Similarity	NPC476870
0.8478	Intermediate Similarity	NPC22150
0.8478	Intermediate Similarity	NPC38041
0.8478	Intermediate Similarity	NPC279298
0.8473	Intermediate Similarity	NPC478255
0.8473	Intermediate Similarity	NPC166168
0.8456	Intermediate Similarity	NPC476385
0.8456	Intermediate Similarity	NPC134405
0.8456	Intermediate Similarity	NPC47471
0.8456	Intermediate Similarity	NPC476377
0.8456	Intermediate Similarity	NPC469661
0.8444	Intermediate Similarity	NPC156376
0.8433	Intermediate Similarity	NPC203230
0.8433	Intermediate Similarity	NPC242028
0.8433	Intermediate Similarity	NPC157554
0.8421	Intermediate Similarity	NPC87696
0.8421	Intermediate Similarity	NPC187194
0.8421	Intermediate Similarity	NPC476411
0.8421	Intermediate Similarity	NPC48863
0.8421	Intermediate Similarity	NPC251981
0.8421	Intermediate Similarity	NPC13745
0.8417	Intermediate Similarity	NPC473867
0.8409	Intermediate Similarity	NPC106739
0.8409	Intermediate Similarity	NPC471505
0.8406	Intermediate Similarity	NPC472713
0.8406	Intermediate Similarity	NPC110063
0.8406	Intermediate Similarity	NPC187774
0.8406	Intermediate Similarity	NPC472712
0.8406	Intermediate Similarity	NPC473046
0.8406	Intermediate Similarity	NPC118385
0.8394	Intermediate Similarity	NPC222433
0.8394	Intermediate Similarity	NPC265648
0.8394	Intermediate Similarity	NPC140502
0.8394	Intermediate Similarity	NPC469559
0.8394	Intermediate Similarity	NPC296643
0.8394	Intermediate Similarity	NPC189115
0.8394	Intermediate Similarity	NPC48309
0.8382	Intermediate Similarity	NPC475530
0.8382	Intermediate Similarity	NPC473799
0.837	Intermediate Similarity	NPC59324
0.837	Intermediate Similarity	NPC65530
0.8359	Intermediate Similarity	NPC131747
0.8359	Intermediate Similarity	NPC257682
0.8359	Intermediate Similarity	NPC146355
0.8358	Intermediate Similarity	NPC142547
0.8358	Intermediate Similarity	NPC135777
0.8358	Intermediate Similarity	NPC174191
0.8357	Intermediate Similarity	NPC15956
0.8357	Intermediate Similarity	NPC31325
0.8357	Intermediate Similarity	NPC224674
0.8357	Intermediate Similarity	NPC193473
0.8357	Intermediate Similarity	NPC275284
0.8357	Intermediate Similarity	NPC39657
0.8357	Intermediate Similarity	NPC213074
0.8357	Intermediate Similarity	NPC114505
0.8346	Intermediate Similarity	NPC52097
0.8346	Intermediate Similarity	NPC164172
0.8346	Intermediate Similarity	NPC215833
0.8346	Intermediate Similarity	NPC49074
0.8346	Intermediate Similarity	NPC69513
0.8333	Intermediate Similarity	NPC247032
0.8333	Intermediate Similarity	NPC476397
0.8333	Intermediate Similarity	NPC476375
0.8333	Intermediate Similarity	NPC175214
0.8333	Intermediate Similarity	NPC96795
0.8333	Intermediate Similarity	NPC277804
0.8333	Intermediate Similarity	NPC264632
0.8333	Intermediate Similarity	NPC475824
0.8333	Intermediate Similarity	NPC476380
0.8333	Intermediate Similarity	NPC205864
0.8333	Intermediate Similarity	NPC119537
0.8333	Intermediate Similarity	NPC76406
0.8333	Intermediate Similarity	NPC473044
0.8333	Intermediate Similarity	NPC113680
0.8333	Intermediate Similarity	NPC112
0.8333	Intermediate Similarity	NPC476381
0.8333	Intermediate Similarity	NPC269141
0.8333	Intermediate Similarity	NPC476407

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 NPC90318 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	747
0.2-0.3	1724
0.3-0.4	3113
0.4-0.5	1839
0.5-0.6	1110
0.6-0.7	326
0.7-0.8	30
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
0.8582	High Similarity	NPD7266	Discontinued
0.791	Intermediate Similarity	NPD3027	Phase 3
0.7846	Intermediate Similarity	NPD1091	Approved
0.7846	Intermediate Similarity	NPD3705	Approved
0.7752	Intermediate Similarity	NPD1357	Approved
0.774	Intermediate Similarity	NPD1653	Approved
0.7737	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1613	Approved
0.7661	Intermediate Similarity	NPD3022	Approved
0.7661	Intermediate Similarity	NPD3021	Approved
0.7569	Intermediate Similarity	NPD6190	Approved
0.7445	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD9384	Approved
0.7424	Intermediate Similarity	NPD9381	Approved
0.7402	Intermediate Similarity	NPD228	Approved
0.7372	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6674	Discontinued
0.7296	Intermediate Similarity	NPD7228	Approved
0.7296	Intermediate Similarity	NPD3818	Discontinued
0.7293	Intermediate Similarity	NPD5125	Phase 3
0.7293	Intermediate Similarity	NPD5126	Approved
0.729	Intermediate Similarity	NPD6234	Discontinued
0.7279	Intermediate Similarity	NPD5058	Phase 3
0.7255	Intermediate Similarity	NPD2978	Approved
0.7255	Intermediate Similarity	NPD2977	Approved
0.7234	Intermediate Similarity	NPD3061	Approved
0.7234	Intermediate Similarity	NPD3062	Approved
0.7234	Intermediate Similarity	NPD3059	Approved
0.7226	Intermediate Similarity	NPD3094	Phase 2
0.7206	Intermediate Similarity	NPD9622	Approved
0.719	Intermediate Similarity	NPD37	Approved
0.7188	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4965	Approved
0.7161	Intermediate Similarity	NPD4967	Phase 2
0.7161	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD7054	Approved
0.7133	Intermediate Similarity	NPD5314	Approved
0.7122	Intermediate Similarity	NPD2861	Phase 2
0.7117	Intermediate Similarity	NPD7685	Pre-registration
0.7114	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7472	Approved
0.7099	Intermediate Similarity	NPD7074	Phase 3
0.7059	Intermediate Similarity	NPD3092	Approved
0.7055	Intermediate Similarity	NPD6797	Phase 2
0.705	Intermediate Similarity	NPD9620	Approved
0.705	Intermediate Similarity	NPD9619	Approved
0.705	Intermediate Similarity	NPD9621	Approved
0.7025	Intermediate Similarity	NPD2934	Approved
0.7025	Intermediate Similarity	NPD2933	Approved
0.7016	Intermediate Similarity	NPD1242	Phase 1
0.7014	Intermediate Similarity	NPD817	Approved
0.7014	Intermediate Similarity	NPD823	Approved
0.7012	Intermediate Similarity	NPD7251	Discontinued
0.6993	Remote Similarity	NPD3620	Phase 2
0.6993	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD598	Approved
0.6972	Remote Similarity	NPD597	Approved
0.6972	Remote Similarity	NPD601	Approved
0.697	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2860	Approved
0.6967	Remote Similarity	NPD2859	Approved
0.6959	Remote Similarity	NPD4236	Phase 3
0.6959	Remote Similarity	NPD4237	Approved
0.6957	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7843	Approved
0.6947	Remote Similarity	NPD9377	Approved
0.6947	Remote Similarity	NPD9379	Approved
0.6944	Remote Similarity	NPD230	Phase 1
0.6939	Remote Similarity	NPD1375	Discontinued
0.6935	Remote Similarity	NPD3020	Approved
0.6923	Remote Similarity	NPD1136	Approved
0.6923	Remote Similarity	NPD1132	Approved
0.6923	Remote Similarity	NPD1130	Approved
0.6918	Remote Similarity	NPD5588	Approved
0.6917	Remote Similarity	NPD7157	Approved
0.6899	Remote Similarity	NPD2684	Approved
0.6899	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5283	Phase 1
0.6889	Remote Similarity	NPD3091	Approved
0.6875	Remote Similarity	NPD7199	Phase 2
0.6871	Remote Similarity	NPD9570	Approved
0.687	Remote Similarity	NPD969	Suspended
0.6867	Remote Similarity	NPD7808	Phase 3
0.6849	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2982	Phase 2
0.6835	Remote Similarity	NPD2983	Phase 2
0.6825	Remote Similarity	NPD846	Approved
0.6825	Remote Similarity	NPD940	Approved
0.6815	Remote Similarity	NPD8455	Phase 2
0.6807	Remote Similarity	NPD7240	Approved
0.6807	Remote Similarity	NPD6559	Discontinued
0.6791	Remote Similarity	NPD6671	Approved
0.6763	Remote Similarity	NPD2981	Phase 2
0.6761	Remote Similarity	NPD3018	Phase 2
0.6759	Remote Similarity	NPD1558	Phase 1
0.6759	Remote Similarity	NPD825	Approved
0.6759	Remote Similarity	NPD826	Approved
0.6752	Remote Similarity	NPD1934	Approved
0.6748	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4538	Approved
0.6735	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4536	Approved
0.6733	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3060	Approved
0.6718	Remote Similarity	NPD4750	Phase 3
0.6718	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4908	Phase 1
0.6709	Remote Similarity	NPD5773	Approved
0.6709	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5772	Approved
0.6694	Remote Similarity	NPD844	Approved
0.6692	Remote Similarity	NPD290	Approved
0.6691	Remote Similarity	NPD1610	Phase 2
0.6689	Remote Similarity	NPD5960	Phase 3
0.6687	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3095	Discontinued
0.6667	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5310	Approved
0.6667	Remote Similarity	NPD5311	Approved
0.6667	Remote Similarity	NPD6653	Approved
0.6646	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6166	Phase 2
0.6645	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4060	Phase 1
0.6643	Remote Similarity	NPD9269	Phase 2
0.6643	Remote Similarity	NPD5736	Approved
0.6642	Remote Similarity	NPD1548	Phase 1
0.6625	Remote Similarity	NPD3882	Suspended
0.6622	Remote Similarity	NPD7097	Phase 1
0.6621	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3053	Approved
0.662	Remote Similarity	NPD3055	Approved
0.662	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD3687	Approved
0.6603	Remote Similarity	NPD3686	Approved
0.6601	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD555	Phase 2
0.6596	Remote Similarity	NPD4749	Approved
0.6579	Remote Similarity	NPD8166	Discontinued
0.6577	Remote Similarity	NPD4108	Discontinued
0.6575	Remote Similarity	NPD6407	Approved
0.6575	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2674	Phase 3
0.6575	Remote Similarity	NPD6405	Approved
0.6556	Remote Similarity	NPD2424	Discontinued
0.6555	Remote Similarity	NPD111	Approved
0.6554	Remote Similarity	NPD2568	Approved
0.6549	Remote Similarity	NPD8651	Approved
0.6536	Remote Similarity	NPD2677	Approved
0.6531	Remote Similarity	NPD943	Approved
0.6531	Remote Similarity	NPD2238	Phase 2
0.6527	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD2231	Phase 2
0.6525	Remote Similarity	NPD2235	Phase 2
0.6524	Remote Similarity	NPD3787	Discontinued
0.6519	Remote Similarity	NPD4380	Phase 2
0.6517	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD1652	Phase 2
0.6508	Remote Similarity	NPD288	Approved
0.6507	Remote Similarity	NPD3764	Approved
0.6503	Remote Similarity	NPD4103	Phase 2
0.6503	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2801	Approved
0.649	Remote Similarity	NPD5763	Approved
0.649	Remote Similarity	NPD5762	Approved
0.6489	Remote Similarity	NPD968	Approved
0.6486	Remote Similarity	NPD5735	Approved
0.6484	Remote Similarity	NPD3028	Approved
0.6481	Remote Similarity	NPD5604	Discontinued
0.6479	Remote Similarity	NPD3685	Discontinued
0.6479	Remote Similarity	NPD4659	Approved
0.6471	Remote Similarity	NPD4628	Phase 3
0.6471	Remote Similarity	NPD9618	Approved
0.6471	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4110	Phase 3
0.6471	Remote Similarity	NPD9614	Approved
0.6464	Remote Similarity	NPD7680	Approved
0.6463	Remote Similarity	NPD6233	Phase 2
0.6463	Remote Similarity	NPD6663	Approved
0.6463	Remote Similarity	NPD259	Phase 1
0.646	Remote Similarity	NPD2563	Approved
0.646	Remote Similarity	NPD2560	Approved
0.646	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD558	Phase 2
0.6458	Remote Similarity	NPD258	Approved
0.6458	Remote Similarity	NPD257	Approved
0.6456	Remote Similarity	NPD3455	Phase 2
0.6454	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1511	Approved
0.6452	Remote Similarity	NPD1774	Approved
0.645	Remote Similarity	NPD7993	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