NPASS Compound

Structure

CID25821 OpenBabel06191715352D 31 33 0 0 1 0 0 0 0 0999 V2000 7.0327 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -3.9945 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 7.8988 -4.4945 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 -3.9945 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 6.1667 -2.4945 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 7.8988 -5.4945 0.0000 O 0 0 0 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 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 6.1667 -1.4945 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 4.4347 -2.4945 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 27 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 9 1 0 0 0 0 5 20 1 0 0 0 0 6 28 1 0 0 0 0 7 19 1 0 0 0 0 7 21 1 0 0 0 0 8 19 1 0 0 0 0 8 29 1 0 0 0 0 10 11 2 0 0 0 0 10 30 1 0 0 0 0 11 27 1 0 0 0 0 12 6 1 1 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 22 1 6 0 0 0 14 15 1 0 0 0 0 14 23 1 1 0 0 0 15 17 1 0 0 0 0 15 24 1 6 0 0 0 16 18 1 0 0 0 0 16 19 1 6 0 0 0 16 25 1 0 0 0 0 17 30 1 1 0 0 0 17 31 1 0 0 0 0 18 28 1 1 0 0 0 18 29 1 0 0 0 0 19 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.16
Volume:	409.084
LogP:	-1.169
LogD:	-1.263
LogS:	-1.649
# Rotatable Bonds:	8
TPSA:	187.76
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.212
Synthetic Accessibility Score:	4.345
Fsp3:	0.684
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.39
MDCK Permeability:	4.6944540372351184e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.937
20% Bioavailability (F20%):	0.514
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.231
Plasma Protein Binding (PPB):	25.3529109954834%
Volume Distribution (VD):	0.392
Pgp-substrate:	49.49628829956055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.368
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.03

ADMET: Excretion

Clearance (CL):	1.281
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.276
Human Hepatotoxicity (H-HT):	0.074
Drug-inuced Liver Injury (DILI):	0.142
AMES Toxicity:	0.24
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.615
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.018
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: NPC25821

Natural Product ID:	NPC25821
*Common Name:**	4-Hydroxymethyl-2-Methoxyphenyl-1-O-Beta-D-Apiofuranosyl-(1-6)-O-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3S,4S,5R,6S)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	CROSCHPQOAEYSN-OTCFHACESA-N
Standard InCHI:	InChI=1S/C19H28O12/c1-27-11-4-9(5-20)2-3-10(11)30-17-15(24)14(23)13(22)12(31-17)6-28-18-16(25)19(26,7-21)8-29-18/h2-4,12-18,20-26H,5-8H2,1H3/t12-,13-,14+,15-,16+,17-,18-,19-/m1/s1
SMILES:	COc1cc(ccc1O[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)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923076
PubChem CID:	21580495
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:0004165] Phenolic glycosides

*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
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	bark	n.a.	n.a.	PMID[22032697]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	bark	n.a.	PMID[22032697]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15954	Pyrenula japonica	Species	Pyrenulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16326	Scopolia parviflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15594	Aplidiopsis confluata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14001	Ceroplastes pseudoceriferus	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16326	Scopolia parviflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5016	Glossogyne tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17444	Gleichenia japonica	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15954	Pyrenula japonica	Species	Pyrenulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15740	Garcinia purpurea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12630	Senecio oxyodontus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14507.1	Quercus ithaburensis subsp. macrolepis	Subspecies	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17757	Plectranthus saccatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16049	Cryptocarya pleurosperma	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10751	Bothriocline laxa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16210	Androcymbium palaestinum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11280	Aphanoascus terreus	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO619	Ankistrodesmus braunii	Species	Selenastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18071	Euryops pedunculatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17141	Lonchocarpus longistylus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17917	Thamnophis sirtalis	Species	Colubridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11755	Banisteriopsis caapi	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17600	Gnathotrichus sulcatus	Species	Curculionidae	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	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[485837]
NPT492	Cell Line	Caco-2	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[485837]
NPT27	Others	Unspecified		IC50	<	5.0	ug.mL-1	PMID[485837]

☑ 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 NPC25821 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	353
0.1-0.2	1393
0.2-0.3	3790
0.3-0.4	9621
0.4-0.5	9162
0.5-0.6	6074
0.6-0.7	8413
0.7-0.8	3061
0.8-0.85	550
0.85-0.9	237
0.9-0.95	38
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC6836
0.9683	High Similarity	NPC248355
0.9683	High Similarity	NPC166040
0.9612	High Similarity	NPC470881
0.9609	High Similarity	NPC252833
0.9606	High Similarity	NPC80600
0.9606	High Similarity	NPC472024
0.9603	High Similarity	NPC302378
0.9528	High Similarity	NPC26653
0.9528	High Similarity	NPC270849
0.9385	High Similarity	NPC49074
0.938	High Similarity	NPC248307
0.938	High Similarity	NPC9912
0.938	High Similarity	NPC65942
0.9375	High Similarity	NPC307110
0.9333	High Similarity	NPC46092
0.9313	High Similarity	NPC48863
0.9313	High Similarity	NPC187194
0.9313	High Similarity	NPC13745
0.9313	High Similarity	NPC251981
0.9308	High Similarity	NPC299144
0.9308	High Similarity	NPC162093
0.9265	High Similarity	NPC470235
0.9265	High Similarity	NPC129417
0.9265	High Similarity	NPC283995
0.9248	High Similarity	NPC138738
0.9248	High Similarity	NPC470413
0.9248	High Similarity	NPC195196
0.9237	High Similarity	NPC69513
0.9237	High Similarity	NPC215833
0.9197	High Similarity	NPC18979
0.9191	High Similarity	NPC185307
0.9191	High Similarity	NPC470950
0.9173	High Similarity	NPC164857
0.9173	High Similarity	NPC25695
0.9173	High Similarity	NPC37468
0.9173	High Similarity	NPC172818
0.9167	High Similarity	NPC476411
0.9167	High Similarity	NPC35731
0.9134	High Similarity	NPC287429
0.913	High Similarity	NPC112861
0.9118	High Similarity	NPC476356
0.9118	High Similarity	NPC246947
0.9104	High Similarity	NPC304152
0.9098	High Similarity	NPC55040
0.9098	High Similarity	NPC470236
0.9091	High Similarity	NPC132895
0.9084	High Similarity	NPC166168
0.9062	High Similarity	NPC470510
0.9058	High Similarity	NPC279298
0.9058	High Similarity	NPC43508
0.9058	High Similarity	NPC22150
0.9058	High Similarity	NPC476301
0.9058	High Similarity	NPC469586
0.9058	High Similarity	NPC38041
0.9044	High Similarity	NPC472711
0.9037	High Similarity	NPC98777
0.9037	High Similarity	NPC226005
0.9037	High Similarity	NPC212770
0.9037	High Similarity	NPC100389
0.903	High Similarity	NPC177035
0.903	High Similarity	NPC52277
0.903	High Similarity	NPC199459
0.903	High Similarity	NPC104167
0.9023	High Similarity	NPC107478
0.9023	High Similarity	NPC87696
0.9015	High Similarity	NPC470270
0.8986	High Similarity	NPC471667
0.8986	High Similarity	NPC471063
0.8986	High Similarity	NPC217635
0.8986	High Similarity	NPC84181
0.8986	High Similarity	NPC79429
0.8978	High Similarity	NPC189115
0.8978	High Similarity	NPC60249
0.8978	High Similarity	NPC469559
0.8978	High Similarity	NPC475084
0.8971	High Similarity	NPC106944
0.8968	High Similarity	NPC198734
0.8968	High Similarity	NPC269242
0.8968	High Similarity	NPC469412
0.8963	High Similarity	NPC477798
0.8963	High Similarity	NPC65530
0.8963	High Similarity	NPC59324
0.8963	High Similarity	NPC477797
0.8955	High Similarity	NPC184938
0.8955	High Similarity	NPC101624
0.8955	High Similarity	NPC174191
0.8929	High Similarity	NPC193473
0.8929	High Similarity	NPC114505
0.8929	High Similarity	NPC39657
0.8929	High Similarity	NPC275284
0.8929	High Similarity	NPC213074
0.8929	High Similarity	NPC31325
0.8929	High Similarity	NPC224674
0.8929	High Similarity	NPC15956
0.8915	High Similarity	NPC90318
0.8913	High Similarity	NPC477898
0.8913	High Similarity	NPC478239
0.8905	High Similarity	NPC76871
0.8905	High Similarity	NPC469661
0.8897	High Similarity	NPC156376
0.8889	High Similarity	NPC203230
0.8889	High Similarity	NPC186418
0.8889	High Similarity	NPC157554
0.8889	High Similarity	NPC242028
0.8873	High Similarity	NPC475224
0.8873	High Similarity	NPC98624
0.8857	High Similarity	NPC205796
0.8857	High Similarity	NPC276753
0.8849	High Similarity	NPC25292
0.8849	High Similarity	NPC110063
0.8849	High Similarity	NPC473045
0.8841	High Similarity	NPC157816
0.8841	High Similarity	NPC302506
0.8841	High Similarity	NPC253878
0.8837	High Similarity	NPC94276
0.8837	High Similarity	NPC109822
0.8832	High Similarity	NPC210478
0.8832	High Similarity	NPC202700
0.8806	High Similarity	NPC115022
0.8806	High Similarity	NPC294166
0.8803	High Similarity	NPC55158
0.8803	High Similarity	NPC286235
0.8803	High Similarity	NPC51328
0.8788	High Similarity	NPC86030
0.8788	High Similarity	NPC97326
0.8788	High Similarity	NPC5851
0.8786	High Similarity	NPC475096
0.8779	High Similarity	NPC118787
0.8779	High Similarity	NPC183181
0.8779	High Similarity	NPC147821
0.8779	High Similarity	NPC111247
0.8779	High Similarity	NPC319625
0.8779	High Similarity	NPC163332
0.8779	High Similarity	NPC41706
0.8779	High Similarity	NPC292056
0.8777	High Similarity	NPC473044
0.8777	High Similarity	NPC81638
0.8777	High Similarity	NPC252169
0.8768	High Similarity	NPC186406
0.8768	High Similarity	NPC471908
0.8768	High Similarity	NPC471414
0.874	High Similarity	NPC469708
0.874	High Similarity	NPC60589
0.8732	High Similarity	NPC270751
0.8732	High Similarity	NPC248132
0.8732	High Similarity	NPC130449
0.8731	High Similarity	NPC219671
0.8731	High Similarity	NPC85799
0.8731	High Similarity	NPC26080
0.8731	High Similarity	NPC303422
0.8731	High Similarity	NPC104077
0.8731	High Similarity	NPC259742
0.8731	High Similarity	NPC165686
0.8731	High Similarity	NPC147616
0.8731	High Similarity	NPC106739
0.8731	High Similarity	NPC471505
0.8723	High Similarity	NPC474234
0.8723	High Similarity	NPC125755
0.8723	High Similarity	NPC99515
0.8723	High Similarity	NPC199928
0.8723	High Similarity	NPC190714
0.8722	High Similarity	NPC474491
0.8714	High Similarity	NPC187774
0.8714	High Similarity	NPC473046
0.8714	High Similarity	NPC472713
0.8714	High Similarity	NPC232228
0.8714	High Similarity	NPC179521
0.8714	High Similarity	NPC297342
0.8714	High Similarity	NPC472712
0.8714	High Similarity	NPC118385
0.8712	High Similarity	NPC470084
0.8712	High Similarity	NPC72529
0.8712	High Similarity	NPC40377
0.8705	High Similarity	NPC48309
0.8705	High Similarity	NPC140502
0.8702	High Similarity	NPC178284
0.8702	High Similarity	NPC473960
0.8702	High Similarity	NPC191037
0.8702	High Similarity	NPC58607
0.8696	High Similarity	NPC226547
0.8692	High Similarity	NPC114901
0.8692	High Similarity	NPC293701
0.8692	High Similarity	NPC48990
0.8682	High Similarity	NPC476142
0.8682	High Similarity	NPC71090
0.8676	High Similarity	NPC18576
0.8676	High Similarity	NPC135777
0.8676	High Similarity	NPC238243
0.8676	High Similarity	NPC142547
0.8671	High Similarity	NPC44452
0.8667	High Similarity	NPC254398
0.8662	High Similarity	NPC99183
0.8662	High Similarity	NPC227902
0.8661	High Similarity	NPC135961
0.8657	High Similarity	NPC469613
0.8657	High Similarity	NPC30043
0.8657	High Similarity	NPC121376
0.8657	High Similarity	NPC469625
0.8657	High Similarity	NPC469698

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 NPC25821 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	798
0.2-0.3	1876
0.3-0.4	2838
0.4-0.5	1728
0.5-0.6	1043
0.6-0.7	516
0.7-0.8	78
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD1091	Approved
0.8516	High Similarity	NPD1357	Approved
0.8462	Intermediate Similarity	NPD3705	Approved
0.8288	Intermediate Similarity	NPD1653	Approved
0.8235	Intermediate Similarity	NPD3027	Phase 3
0.8112	Intermediate Similarity	NPD6674	Discontinued
0.8099	Intermediate Similarity	NPD7266	Discontinued
0.8058	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD1613	Approved
0.7945	Intermediate Similarity	NPD5058	Phase 3
0.777	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD228	Approved
0.7724	Intermediate Similarity	NPD1375	Discontinued
0.7712	Intermediate Similarity	NPD37	Approved
0.7698	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7843	Approved
0.7688	Intermediate Similarity	NPD3818	Discontinued
0.7677	Intermediate Similarity	NPD4966	Approved
0.7677	Intermediate Similarity	NPD4967	Phase 2
0.7677	Intermediate Similarity	NPD4965	Approved
0.7656	Intermediate Similarity	NPD2684	Approved
0.7652	Intermediate Similarity	NPD7157	Approved
0.7651	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7054	Approved
0.7595	Intermediate Similarity	NPD7199	Phase 2
0.7593	Intermediate Similarity	NPD7074	Phase 3
0.7593	Intermediate Similarity	NPD7472	Approved
0.758	Intermediate Similarity	NPD6234	Discontinued
0.7578	Intermediate Similarity	NPD290	Approved
0.7578	Intermediate Similarity	NPD7228	Approved
0.7571	Intermediate Similarity	NPD2861	Phase 2
0.7548	Intermediate Similarity	NPD2977	Approved
0.7548	Intermediate Similarity	NPD2978	Approved
0.7536	Intermediate Similarity	NPD2982	Phase 2
0.7536	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD4237	Approved
0.75	Intermediate Similarity	NPD5283	Phase 1
0.75	Intermediate Similarity	NPD4236	Phase 3
0.7466	Intermediate Similarity	NPD5588	Approved
0.7464	Intermediate Similarity	NPD2981	Phase 2
0.746	Intermediate Similarity	NPD291	Approved
0.7455	Intermediate Similarity	NPD7808	Phase 3
0.7447	Intermediate Similarity	NPD3018	Phase 2
0.7439	Intermediate Similarity	NPD6797	Phase 2
0.7436	Intermediate Similarity	NPD5773	Approved
0.7436	Intermediate Similarity	NPD5772	Approved
0.741	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4536	Approved
0.7397	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4538	Approved
0.7394	Intermediate Similarity	NPD7251	Discontinued
0.7391	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD6671	Approved
0.7383	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3687	Approved
0.7338	Intermediate Similarity	NPD3686	Approved
0.7329	Intermediate Similarity	NPD6653	Approved
0.7328	Intermediate Similarity	NPD556	Approved
0.7325	Intermediate Similarity	NPD8455	Phase 2
0.731	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1558	Phase 1
0.731	Intermediate Similarity	NPD3620	Phase 2
0.7296	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6559	Discontinued
0.7289	Intermediate Similarity	NPD7240	Approved
0.7279	Intermediate Similarity	NPD7097	Phase 1
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7261	Intermediate Similarity	NPD1934	Approved
0.7255	Intermediate Similarity	NPD4123	Phase 3
0.7246	Intermediate Similarity	NPD5126	Approved
0.7246	Intermediate Similarity	NPD5125	Phase 3
0.7234	Intermediate Similarity	NPD8651	Approved
0.723	Intermediate Similarity	NPD5960	Phase 3
0.7219	Intermediate Similarity	NPD4110	Phase 3
0.7219	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2424	Discontinued
0.7192	Intermediate Similarity	NPD4060	Phase 1
0.719	Intermediate Similarity	NPD1774	Approved
0.7188	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2677	Approved
0.7171	Intermediate Similarity	NPD6190	Approved
0.717	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2560	Approved
0.717	Intermediate Similarity	NPD2563	Approved
0.7163	Intermediate Similarity	NPD3685	Discontinued
0.7163	Intermediate Similarity	NPD4749	Approved
0.7161	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5536	Phase 2
0.7152	Intermediate Similarity	NPD3060	Approved
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.7152	Intermediate Similarity	NPD4162	Approved
0.7143	Intermediate Similarity	NPD5735	Approved
0.7143	Intermediate Similarity	NPD1610	Phase 2
0.7134	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6166	Phase 2
0.7134	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4678	Approved
0.7134	Intermediate Similarity	NPD4675	Approved
0.7133	Intermediate Similarity	NPD5762	Approved
0.7133	Intermediate Similarity	NPD5763	Approved
0.7125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3882	Suspended
0.7123	Intermediate Similarity	NPD6233	Phase 2
0.7118	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4628	Phase 3
0.7103	Intermediate Similarity	NPD3179	Approved
0.7103	Intermediate Similarity	NPD7095	Approved
0.7103	Intermediate Similarity	NPD3180	Approved
0.7101	Intermediate Similarity	NPD1548	Phase 1
0.7099	Intermediate Similarity	NPD968	Approved
0.7092	Intermediate Similarity	NPD2235	Phase 2
0.7092	Intermediate Similarity	NPD2231	Phase 2
0.7071	Intermediate Similarity	NPD3496	Discontinued
0.707	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2161	Phase 2
0.7063	Intermediate Similarity	NPD3817	Phase 2
0.7051	Intermediate Similarity	NPD2122	Discontinued
0.7035	Intermediate Similarity	NPD6841	Approved
0.7035	Intermediate Similarity	NPD6842	Approved
0.7035	Intermediate Similarity	NPD6843	Phase 3
0.7034	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5124	Phase 1
0.7027	Intermediate Similarity	NPD6355	Discontinued
0.7027	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD558	Phase 2
0.7013	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6071	Discontinued
0.7012	Intermediate Similarity	NPD3787	Discontinued
0.7006	Intermediate Similarity	NPD4210	Discontinued
0.7006	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD1778	Approved
0.7	Intermediate Similarity	NPD4108	Discontinued
0.7	Intermediate Similarity	NPD6516	Phase 2
0.7	Intermediate Similarity	NPD5846	Approved
0.7	Intermediate Similarity	NPD2801	Approved
0.6993	Remote Similarity	NPD6331	Phase 2
0.6993	Remote Similarity	NPD6696	Suspended
0.6987	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD52	Approved
0.6987	Remote Similarity	NPD7526	Approved
0.6986	Remote Similarity	NPD4625	Phase 3
0.698	Remote Similarity	NPD2492	Phase 1
0.6978	Remote Similarity	NPD1182	Approved
0.6975	Remote Similarity	NPD5604	Discontinued
0.697	Remote Similarity	NPD2969	Approved
0.697	Remote Similarity	NPD2970	Approved
0.6959	Remote Similarity	NPD4140	Approved
0.6959	Remote Similarity	NPD2238	Phase 2
0.6951	Remote Similarity	NPD8127	Discontinued
0.694	Remote Similarity	NPD3021	Approved
0.694	Remote Similarity	NPD3022	Approved
0.6939	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6798	Discontinued
0.6928	Remote Similarity	NPD5177	Phase 3
0.6918	Remote Similarity	NPD7028	Phase 2
0.6917	Remote Similarity	NPD1358	Approved
0.6913	Remote Similarity	NPD447	Suspended
0.6913	Remote Similarity	NPD4340	Discontinued
0.6912	Remote Similarity	NPD821	Approved
0.6909	Remote Similarity	NPD3051	Approved
0.6908	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6004	Phase 3
0.6908	Remote Similarity	NPD3540	Phase 1
0.6908	Remote Similarity	NPD6002	Phase 3
0.6908	Remote Similarity	NPD6005	Phase 3
0.6905	Remote Similarity	NPD5844	Phase 1
0.6901	Remote Similarity	NPD422	Phase 1
0.6901	Remote Similarity	NPD776	Approved
0.6897	Remote Similarity	NPD6584	Phase 3
0.6894	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4062	Phase 3
0.6892	Remote Similarity	NPD2674	Phase 3
0.6883	Remote Similarity	NPD4535	Phase 3
0.6879	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4357	Discontinued
0.6855	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD9494	Approved
0.6845	Remote Similarity	NPD3751	Discontinued
0.6842	Remote Similarity	NPD3539	Phase 1
0.6839	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2219	Phase 1
0.6839	Remote Similarity	NPD7906	Approved
0.6838	Remote Similarity	NPD969	Suspended
0.6832	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD27	Approved
0.6826	Remote Similarity	NPD2489	Approved
0.6824	Remote Similarity	NPD3144	Approved
0.6824	Remote Similarity	NPD7007	Discovery
0.6824	Remote Similarity	NPD3145	Approved
0.6815	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4739	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