NPASS Compound

Structure

CID14950 OpenBabel06191715342D 21 22 0 0 1 0 0 0 0 0999 V2000 -1.7321 1.0000 0.0000 C 0 5 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 N 0 3 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 2.5981 0.5000 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 0.8660 -2.5000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 3 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 8 2 0 0 0 0 6 8 1 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 9 7 1 6 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 1 0 0 0 11 12 1 0 0 0 0 11 18 1 6 0 0 0 12 14 1 0 0 0 0 12 19 1 1 0 0 0 13 15 1 6 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 6 0 0 0 M CHG 2 1 -1 15 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	295.11
Volume:	284.143
LogP:	-0.418
LogD:	-0.122
LogS:	-0.881
# Rotatable Bonds:	4
TPSA:	103.74
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	4.163
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.401
MDCK Permeability:	5.5830678320489824e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.18
Human Intestinal Absorption (HIA):	0.912
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.277
Plasma Protein Binding (PPB):	30.366268157958984%
Volume Distribution (VD):	0.711
Pgp-substrate:	62.57823181152344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.063

ADMET: Excretion

Clearance (CL):	2.068
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.515
Rat Oral Acute Toxicity:	0.504
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.511
Carcinogencity:	0.114
Eye Corrosion:	0.004
Eye Irritation:	0.294
Respiratory Toxicity:	0.137

Download Data

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

Natural Product: NPC14950

Natural Product ID:	NPC14950
*Common Name:**	(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-[(R)-Isocyano(Phenyl)Methoxy]Oxane-3,4,5-Triol
IUPAC Name:	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(R)-isocyano(phenyl)methoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	BCXGVHRDMLVEHQ-WNWFYDSVSA-N
Standard InCHI:	InChI=1S/C14H17NO6/c1-15-13(8-5-3-2-4-6-8)21-14-12(19)11(18)10(17)9(7-16)20-14/h2-6,9-14,16-19H,7H2/t9-,10-,11+,12-,13-,14+/m1/s1
SMILES:	[C-]#[N+][C@@H](c1ccccc1)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1871737
PubChem CID:	23641103
Chemical Classification:**	CHEMONTID:0000000 [Organic 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
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[10670815]
NPO6473.1	Perilla frutescens var. acuta	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757731]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	Malatya Fruit Research Institute	between the first and third weeks of 2005-Jul.	PMID[18038980]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6473.1	Perilla frutescens var. acuta	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30133	Cystopteris sp	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4784	Semen armeniacae amarum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO10853	Cystopteris sp.	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6473.1	Perilla frutescens var. acuta	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4795	Prunus armeniaca	Species	Rosaceae	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
Potency	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[489956]

☑ 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 NPC14950 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	160
0.1-0.2	1017
0.2-0.3	3348
0.3-0.4	11160
0.4-0.5	14005
0.5-0.6	11102
0.6-0.7	1776
0.7-0.8	112
0.8-0.85	13
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8783	High Similarity	NPC120217
0.8739	High Similarity	NPC37714
0.8739	High Similarity	NPC152384
0.8487	Intermediate Similarity	NPC216605
0.8487	Intermediate Similarity	NPC266389
0.8487	Intermediate Similarity	NPC122245
0.8435	Intermediate Similarity	NPC474148
0.8435	Intermediate Similarity	NPC276061
0.8362	Intermediate Similarity	NPC30563
0.8362	Intermediate Similarity	NPC264784
0.8319	Intermediate Similarity	NPC148060
0.812	Intermediate Similarity	NPC36434
0.806	Intermediate Similarity	NPC298821
0.8036	Intermediate Similarity	NPC262826
0.8016	Intermediate Similarity	NPC212176
0.8	Intermediate Similarity	NPC123761
0.7951	Intermediate Similarity	NPC175771
0.7913	Intermediate Similarity	NPC469527
0.7826	Intermediate Similarity	NPC136951
0.7826	Intermediate Similarity	NPC161155
0.7826	Intermediate Similarity	NPC97004
0.7787	Intermediate Similarity	NPC313193
0.777	Intermediate Similarity	NPC97282
0.7692	Intermediate Similarity	NPC47286
0.7642	Intermediate Similarity	NPC157338
0.7638	Intermediate Similarity	NPC198734
0.7638	Intermediate Similarity	NPC469412
0.7638	Intermediate Similarity	NPC229600
0.7638	Intermediate Similarity	NPC269242
0.7634	Intermediate Similarity	NPC198798
0.7626	Intermediate Similarity	NPC178466
0.7626	Intermediate Similarity	NPC63628
0.7583	Intermediate Similarity	NPC184633
0.7578	Intermediate Similarity	NPC226712
0.7559	Intermediate Similarity	NPC60589
0.7559	Intermediate Similarity	NPC469708
0.752	Intermediate Similarity	NPC148055
0.7519	Intermediate Similarity	NPC476142
0.7405	Intermediate Similarity	NPC57607
0.7398	Intermediate Similarity	NPC470825
0.7348	Intermediate Similarity	NPC470510
0.7317	Intermediate Similarity	NPC43584
0.7308	Intermediate Similarity	NPC11724
0.7293	Intermediate Similarity	NPC114096
0.7287	Intermediate Similarity	NPC282409
0.7287	Intermediate Similarity	NPC469702
0.728	Intermediate Similarity	NPC474641
0.7273	Intermediate Similarity	NPC287429
0.7252	Intermediate Similarity	NPC52097
0.7239	Intermediate Similarity	NPC148026
0.7234	Intermediate Similarity	NPC195814
0.7231	Intermediate Similarity	NPC476872
0.7231	Intermediate Similarity	NPC469704
0.7231	Intermediate Similarity	NPC160854
0.7231	Intermediate Similarity	NPC476448
0.7231	Intermediate Similarity	NPC469703
0.7231	Intermediate Similarity	NPC476445
0.7231	Intermediate Similarity	NPC469548
0.7231	Intermediate Similarity	NPC201402
0.7222	Intermediate Similarity	NPC29607
0.72	Intermediate Similarity	NPC320064
0.7192	Intermediate Similarity	NPC139699
0.7192	Intermediate Similarity	NPC114659
0.7185	Intermediate Similarity	NPC146540
0.7185	Intermediate Similarity	NPC40377
0.7185	Intermediate Similarity	NPC301857
0.7176	Intermediate Similarity	NPC266045
0.7176	Intermediate Similarity	NPC469686
0.7176	Intermediate Similarity	NPC55608
0.7132	Intermediate Similarity	NPC26653
0.7132	Intermediate Similarity	NPC27712
0.7132	Intermediate Similarity	NPC97326
0.7132	Intermediate Similarity	NPC270849
0.7132	Intermediate Similarity	NPC166040
0.7131	Intermediate Similarity	NPC475203
0.7131	Intermediate Similarity	NPC474376
0.7131	Intermediate Similarity	NPC472315
0.7131	Intermediate Similarity	NPC472316
0.7121	Intermediate Similarity	NPC471067
0.712	Intermediate Similarity	NPC185840
0.7111	Intermediate Similarity	NPC288416
0.7109	Intermediate Similarity	NPC301651
0.7109	Intermediate Similarity	NPC473556
0.709	Intermediate Similarity	NPC83218
0.709	Intermediate Similarity	NPC12308
0.709	Intermediate Similarity	NPC126991
0.708	Intermediate Similarity	NPC472024
0.708	Intermediate Similarity	NPC80600
0.7068	Intermediate Similarity	NPC138798
0.7068	Intermediate Similarity	NPC178449
0.7068	Intermediate Similarity	NPC470907
0.7068	Intermediate Similarity	NPC232454
0.7059	Intermediate Similarity	NPC302378
0.7055	Intermediate Similarity	NPC476743
0.7037	Intermediate Similarity	NPC252114
0.7037	Intermediate Similarity	NPC471157
0.7029	Intermediate Similarity	NPC246869
0.7029	Intermediate Similarity	NPC475067
0.7029	Intermediate Similarity	NPC225384
0.7029	Intermediate Similarity	NPC138777
0.7029	Intermediate Similarity	NPC65942
0.7029	Intermediate Similarity	NPC9912
0.7029	Intermediate Similarity	NPC248307
0.7029	Intermediate Similarity	NPC166168
0.7023	Intermediate Similarity	NPC146673
0.7023	Intermediate Similarity	NPC233923
0.7008	Intermediate Similarity	NPC474544
0.7008	Intermediate Similarity	NPC1986
0.7007	Intermediate Similarity	NPC476744
0.7007	Intermediate Similarity	NPC218003
0.7007	Intermediate Similarity	NPC307110
0.7007	Intermediate Similarity	NPC295970
0.7007	Intermediate Similarity	NPC248355
0.7	Intermediate Similarity	NPC10221
0.7	Intermediate Similarity	NPC187028
0.7	Intermediate Similarity	NPC140915
0.7	Intermediate Similarity	NPC18249
0.7	Intermediate Similarity	NPC197741
0.7	Intermediate Similarity	NPC305700
0.6992	Remote Similarity	NPC136962
0.6992	Remote Similarity	NPC37115
0.6985	Remote Similarity	NPC173150
0.6985	Remote Similarity	NPC35288
0.6985	Remote Similarity	NPC471882
0.6985	Remote Similarity	NPC156692
0.6985	Remote Similarity	NPC45224
0.6985	Remote Similarity	NPC471881
0.6985	Remote Similarity	NPC106677
0.6978	Remote Similarity	NPC269421
0.6978	Remote Similarity	NPC254275
0.6968	Remote Similarity	NPC470971
0.6967	Remote Similarity	NPC280616
0.6967	Remote Similarity	NPC242913
0.6967	Remote Similarity	NPC171831
0.6963	Remote Similarity	NPC90318
0.6963	Remote Similarity	NPC123704
0.6957	Remote Similarity	NPC474491
0.6957	Remote Similarity	NPC262606
0.6953	Remote Similarity	NPC142319
0.6947	Remote Similarity	NPC477803
0.6947	Remote Similarity	NPC238582
0.6942	Remote Similarity	NPC60373
0.6942	Remote Similarity	NPC154905
0.6935	Remote Similarity	NPC277788
0.6934	Remote Similarity	NPC225307
0.6934	Remote Similarity	NPC232880
0.6929	Remote Similarity	NPC6836
0.6929	Remote Similarity	NPC114116
0.6929	Remote Similarity	NPC265002
0.6929	Remote Similarity	NPC25821
0.6913	Remote Similarity	NPC476742
0.6912	Remote Similarity	NPC61181
0.6906	Remote Similarity	NPC46137
0.6906	Remote Similarity	NPC478255
0.6906	Remote Similarity	NPC121376
0.6906	Remote Similarity	NPC235294
0.6889	Remote Similarity	NPC145287
0.6884	Remote Similarity	NPC477293
0.6884	Remote Similarity	NPC229784
0.6884	Remote Similarity	NPC477294
0.6884	Remote Similarity	NPC253595
0.6879	Remote Similarity	NPC87696
0.6879	Remote Similarity	NPC470881
0.6879	Remote Similarity	NPC34456
0.6879	Remote Similarity	NPC187194
0.6879	Remote Similarity	NPC471029
0.6879	Remote Similarity	NPC476411
0.6879	Remote Similarity	NPC35731
0.6875	Remote Similarity	NPC172525
0.6867	Remote Similarity	NPC476741
0.6866	Remote Similarity	NPC140561
0.6866	Remote Similarity	NPC141970
0.6866	Remote Similarity	NPC476278
0.6864	Remote Similarity	NPC20142
0.6864	Remote Similarity	NPC215351
0.6861	Remote Similarity	NPC103533
0.6861	Remote Similarity	NPC264900
0.6861	Remote Similarity	NPC476873
0.6861	Remote Similarity	NPC108659
0.6861	Remote Similarity	NPC469687
0.6861	Remote Similarity	NPC231607
0.6861	Remote Similarity	NPC79715
0.686	Remote Similarity	NPC228400
0.686	Remote Similarity	NPC214200
0.6857	Remote Similarity	NPC165686
0.6857	Remote Similarity	NPC303422
0.6857	Remote Similarity	NPC26080
0.6857	Remote Similarity	NPC299144
0.6857	Remote Similarity	NPC252833
0.6857	Remote Similarity	NPC162093
0.6857	Remote Similarity	NPC470270
0.6857	Remote Similarity	NPC85799
0.685	Remote Similarity	NPC234376
0.6833	Remote Similarity	NPC475954
0.6831	Remote Similarity	NPC79957
0.6821	Remote Similarity	NPC471073
0.6821	Remote Similarity	NPC270811
0.6812	Remote Similarity	NPC148982
0.6809	Remote Similarity	NPC69513
0.6809	Remote Similarity	NPC132895

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 NPC14950 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	128
0.1-0.2	610
0.2-0.3	893
0.3-0.4	2659
0.4-0.5	2920
0.5-0.6	1648
0.6-0.7	285
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7578	Intermediate Similarity	NPD1091	Approved
0.7422	Intermediate Similarity	NPD5126	Approved
0.7422	Intermediate Similarity	NPD5125	Phase 3
0.7258	Intermediate Similarity	NPD969	Suspended
0.7172	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5723	Approved
0.7037	Intermediate Similarity	NPD7247	Discontinued
0.6992	Remote Similarity	NPD811	Approved
0.6992	Remote Similarity	NPD812	Approved
0.6992	Remote Similarity	NPD810	Approved
0.6855	Remote Similarity	NPD3526	Approved
0.6855	Remote Similarity	NPD3524	Approved
0.6818	Remote Similarity	NPD770	Discontinued
0.6803	Remote Similarity	NPD854	Approved
0.6803	Remote Similarity	NPD855	Approved
0.68	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD794	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2555	Approved
0.6721	Remote Similarity	NPD2552	Approved
0.6721	Remote Similarity	NPD2558	Approved
0.6721	Remote Similarity	NPD2549	Approved
0.6721	Remote Similarity	NPD2553	Approved
0.6721	Remote Similarity	NPD2550	Approved
0.6694	Remote Similarity	NPD9609	Approved
0.6694	Remote Similarity	NPD9612	Approved
0.6694	Remote Similarity	NPD9611	Approved
0.6693	Remote Similarity	NPD550	Approved
0.6693	Remote Similarity	NPD551	Approved
0.6693	Remote Similarity	NPD9713	Approved
0.6667	Remote Similarity	NPD2485	Approved
0.6667	Remote Similarity	NPD4189	Approved
0.6667	Remote Similarity	NPD4188	Approved
0.6667	Remote Similarity	NPD2484	Approved
0.6641	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD2625	Approved
0.6594	Remote Similarity	NPD2160	Approved
0.6594	Remote Similarity	NPD2159	Approved
0.6594	Remote Similarity	NPD2626	Approved
0.6594	Remote Similarity	NPD2628	Approved
0.6594	Remote Similarity	NPD2627	Approved
0.6589	Remote Similarity	NPD4572	Approved
0.6589	Remote Similarity	NPD4573	Approved
0.6589	Remote Similarity	NPD4571	Approved
0.6575	Remote Similarity	NPD7266	Discontinued
0.6575	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD1375	Discontinued
0.6569	Remote Similarity	NPD3685	Discontinued
0.6562	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.656	Remote Similarity	NPD3048	Approved
0.656	Remote Similarity	NPD3047	Approved
0.656	Remote Similarity	NPD314	Approved
0.656	Remote Similarity	NPD311	Approved
0.656	Remote Similarity	NPD315	Approved
0.656	Remote Similarity	NPD310	Approved
0.656	Remote Similarity	NPD10	Approved
0.656	Remote Similarity	NPD309	Approved
0.656	Remote Similarity	NPD3046	Approved
0.6554	Remote Similarity	NPD2575	Approved
0.6547	Remote Similarity	NPD558	Phase 2
0.6535	Remote Similarity	NPD290	Approved
0.6535	Remote Similarity	NPD9532	Phase 3
0.6525	Remote Similarity	NPD3180	Approved
0.6525	Remote Similarity	NPD3179	Approved
0.6512	Remote Similarity	NPD2201	Approved
0.6496	Remote Similarity	NPD2235	Phase 2
0.6496	Remote Similarity	NPD2231	Phase 2
0.649	Remote Similarity	NPD4123	Phase 3
0.6474	Remote Similarity	NPD2977	Approved
0.6474	Remote Similarity	NPD2978	Approved
0.6467	Remote Similarity	NPD3122	Phase 3
0.6466	Remote Similarity	NPD5291	Approved
0.6466	Remote Similarity	NPD5292	Approved
0.6463	Remote Similarity	NPD3656	Approved
0.6463	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD2551	Approved
0.6457	Remote Similarity	NPD2559	Approved
0.6438	Remote Similarity	NPD4108	Discontinued
0.6434	Remote Similarity	NPD5237	Approved
0.6434	Remote Similarity	NPD7477	Discontinued
0.6434	Remote Similarity	NPD5239	Approved
0.6434	Remote Similarity	NPD5236	Approved
0.6434	Remote Similarity	NPD5235	Approved
0.6434	Remote Similarity	NPD5240	Approved
0.6418	Remote Similarity	NPD16	Approved
0.6418	Remote Similarity	NPD856	Approved
0.641	Remote Similarity	NPD4433	Discontinued
0.6408	Remote Similarity	NPD4738	Phase 2
0.6403	Remote Similarity	NPD5667	Approved
0.64	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD9384	Approved
0.6397	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD9381	Approved
0.6389	Remote Similarity	NPD2238	Phase 2
0.6387	Remote Similarity	NPD4678	Approved
0.6387	Remote Similarity	NPD4675	Approved
0.6382	Remote Similarity	NPD3536	Discontinued
0.6377	Remote Similarity	NPD7249	Approved
0.6377	Remote Similarity	NPD7250	Approved
0.6376	Remote Similarity	NPD4236	Phase 3
0.6376	Remote Similarity	NPD4237	Approved
0.637	Remote Similarity	NPD7741	Discontinued
0.6364	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD3826	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD5604	Discontinued
0.6349	Remote Similarity	NPD3683	Approved
0.6349	Remote Similarity	NPD3681	Approved
0.6349	Remote Similarity	NPD4658	Approved
0.6349	Remote Similarity	NPD4656	Approved
0.6349	Remote Similarity	NPD4229	Approved
0.6349	Remote Similarity	NPD4231	Approved
0.6343	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5500	Discontinued
0.6338	Remote Similarity	NPD5201	Approved
0.6338	Remote Similarity	NPD4620	Approved
0.6338	Remote Similarity	NPD2613	Approved
0.6338	Remote Similarity	NPD5203	Approved
0.6338	Remote Similarity	NPD4617	Approved
0.6331	Remote Similarity	NPD4659	Approved
0.6324	Remote Similarity	NPD6382	Discontinued
0.6324	Remote Similarity	NPD2595	Approved
0.6324	Remote Similarity	NPD2594	Approved
0.6319	Remote Similarity	NPD2674	Phase 3
0.6319	Remote Similarity	NPD6405	Approved
0.6319	Remote Similarity	NPD6407	Approved
0.6319	Remote Similarity	NPD840	Approved
0.6319	Remote Similarity	NPD839	Approved
0.6303	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD3052	Approved
0.6301	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD3054	Approved
0.6296	Remote Similarity	NPD317	Approved
0.6296	Remote Similarity	NPD318	Approved
0.6291	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD2677	Approved
0.6291	Remote Similarity	NPD5160	Discontinued
0.6279	Remote Similarity	NPD6406	Approved
0.6277	Remote Similarity	NPD5305	Approved
0.6277	Remote Similarity	NPD2668	Approved
0.6277	Remote Similarity	NPD2667	Approved
0.6277	Remote Similarity	NPD5306	Approved
0.6276	Remote Similarity	NPD3062	Approved
0.6276	Remote Similarity	NPD3061	Approved
0.6276	Remote Similarity	NPD3059	Approved
0.6275	Remote Similarity	NPD681	Clinical (unspecified phase)
0.627	Remote Similarity	NPD4719	Phase 2
0.627	Remote Similarity	NPD4817	Approved
0.627	Remote Similarity	NPD4818	Approved
0.6269	Remote Similarity	NPD4198	Discontinued
0.6269	Remote Similarity	NPD7508	Discontinued
0.6267	Remote Similarity	NPD3060	Approved
0.6267	Remote Similarity	NPD5177	Phase 3
0.6267	Remote Similarity	NPD5061	Approved
0.6267	Remote Similarity	NPD5062	Approved
0.6266	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD2562	Approved
0.6259	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD2561	Approved
0.6258	Remote Similarity	NPD3687	Approved
0.6258	Remote Similarity	NPD1653	Approved
0.6258	Remote Similarity	NPD3686	Approved
0.625	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3145	Approved
0.625	Remote Similarity	NPD4016	Approved
0.625	Remote Similarity	NPD7042	Phase 3
0.625	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5058	Phase 3
0.625	Remote Similarity	NPD1048	Approved
0.625	Remote Similarity	NPD5295	Discontinued
0.625	Remote Similarity	NPD9294	Approved
0.625	Remote Similarity	NPD3144	Approved
0.6242	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD1794	Approved
0.6241	Remote Similarity	NPD1820	Approved
0.6241	Remote Similarity	NPD1819	Approved
0.6241	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD1818	Approved
0.6241	Remote Similarity	NPD4103	Phase 2
0.6241	Remote Similarity	NPD1817	Approved
0.6232	Remote Similarity	NPD4135	Approved
0.6232	Remote Similarity	NPD4106	Approved
0.6232	Remote Similarity	NPD4136	Approved
0.6231	Remote Similarity	NPD2684	Approved
0.623	Remote Similarity	NPD1080	Approved
0.6228	Remote Similarity	NPD7007	Discovery
0.6226	Remote Similarity	NPD2560	Approved
0.6226	Remote Similarity	NPD2563	Approved
0.6225	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD600	Approved
0.6224	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD596	Approved
0.6222	Remote Similarity	NPD694	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3682	Approved
0.622	Remote Similarity	NPD3680	Approved
0.6218	Remote Similarity	NPD531	Approved
0.6214	Remote Similarity	NPD7876	Discontinued
0.6214	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD9622	Approved
0.6209	Remote Similarity	NPD1774	Approved
0.6207	Remote Similarity	NPD2571	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