NPASS Compound

Structure

NPC163846 OpenBabel07101719242D 25 26 0 0 0 0 0 0 0 0999 V2000 -2.5981 2.5000 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 1.7321 3.0000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 1.7321 1.0000 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 4.3301 -0.5000 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 -0.0000 1.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 9 14 2 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 16 19 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 25 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.17
Volume:	368.728
LogP:	5.704
LogD:	3.852
LogS:	-4.181
# Rotatable Bonds:	7
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.734
Synthetic Accessibility Score:	2.356
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.934
MDCK Permeability:	2.160499570891261e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.074
30% Bioavailability (F30%):	0.206

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	99.5198974609375%
Volume Distribution (VD):	0.291
Pgp-substrate:	1.0718774795532227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.206
CYP1A2-substrate:	0.699
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.764
CYP2C9-substrate:	0.373
CYP2D6-inhibitor:	0.611
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	4.278
Half-life (T1/2):	0.688

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.735
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.13
Carcinogencity:	0.074
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.818

Download Data

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

Natural Product: NPC163846

Natural Product ID:	NPC163846
*Common Name:**	Amorfrutin A
IUPAC Name:	2-hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-6-(2-phenylethyl)benzoic acid
Synonyms:
Standard InCHIKey:	CTNFTPUIYFUXBE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H24O4/c1-14(2)9-12-17-18(25-3)13-16(19(20(17)22)21(23)24)11-10-15-7-5-4-6-8-15/h4-9,13,22H,10-12H2,1-3H3,(H,23,24)
SMILES:	COc1cc(CCc2ccccc2)c(c(c1CC=C(C)C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491820
PubChem CID:	17950432
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18841906]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28075580]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326318]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350086]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16886	Amorpha fruticosa	Species	Fabaceae	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
EC50	4
IC50	6
Kd	3
MIC	8
Others	5
Potency	17

Activity Type	# Activity
Cell Line	3
Individual Protein	20
Organism	9
Others	9
PROTEIN COMPLEX	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[483534]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[483534]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[483534]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	10322.5	nM	PMID[483534]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	25118.9	nM	PMID[483534]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[483534]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	63095.7	nM	PMID[483534]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Kd	=	27000.0	nM	PMID[483535]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[483534]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[483534]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[483534]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[483534]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[483534]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	50800.0	nM	PMID[483536]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	50000.0	nM	PMID[483538]
NPT2	Others	Unspecified		IC50	=	840.0	nM	PMID[483533]
NPT2	Others	Unspecified		IC50	=	4170.0	nM	PMID[483533]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[483534]
NPT25197	PROTEIN COMPLEX	Corticotropin-releasing factor receptor 2/Corticotropin-releasing factor-binding protein	Homo sapiens	EC50	=	35200.0	nM	PMID[483534]
NPT25197	PROTEIN COMPLEX	Corticotropin-releasing factor receptor 2/Corticotropin-releasing factor-binding protein	Homo sapiens	IC50	=	7930.0	nM	PMID[483534]
NPT2	Others	Unspecified		IC50	n.a.	12100.0	nM	PMID[483534]
NPT2	Others	Unspecified		Potency	n.a.	50118.7	nM	PMID[483534]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Activity	=	39.0	%	PMID[483535]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	EC50	=	458.0	nM	PMID[483535]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Kd	=	236.0	nM	PMID[483535]
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	Kd	=	27000.0	nM	PMID[483535]
NPT2	Others	Unspecified		Potency	n.a.	39810.7	nM	PMID[483534]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	26679.5	nM	PMID[483534]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[483534]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	%max	=	39.0	%	PMID[483537]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	EC50	=	458.0	nM	PMID[483537]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50000.0	nM	PMID[483538]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6300.0	nM	PMID[483538]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	100000.0	nM	PMID[483538]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	25000.0	nM	PMID[483538]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	50000.0	nM	PMID[483538]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	25000.0	nM	PMID[483538]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	50000.0	nM	PMID[483538]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	50000.0	nM	PMID[483538]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	-31.3	%	PMID[483539]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	35.0	n.a.	PMID[483540]
NPT2	Others	Unspecified		EC50	=	1680.0	nM	PMID[483540]
NPT2	Others	Unspecified		CC50	=	59350.0	nM	PMID[483540]

☑ 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 NPC163846 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	349
0.1-0.2	1572
0.2-0.3	3654
0.3-0.4	8756
0.4-0.5	9666
0.5-0.6	3307
0.6-0.7	5730
0.7-0.8	6465
0.8-0.85	2179
0.85-0.9	861
0.9-0.95	146
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC225173
0.9929	High Similarity	NPC125801
0.9712	High Similarity	NPC250755
0.965	High Similarity	NPC291049
0.965	High Similarity	NPC233267
0.958	High Similarity	NPC105415
0.9568	High Similarity	NPC165172
0.9517	High Similarity	NPC133856
0.9504	High Similarity	NPC84266
0.9452	High Similarity	NPC273483
0.9444	High Similarity	NPC37139
0.9444	High Similarity	NPC2569
0.9444	High Similarity	NPC172329
0.9433	High Similarity	NPC94076
0.9433	High Similarity	NPC182255
0.9379	High Similarity	NPC329933
0.9375	High Similarity	NPC34802
0.9371	High Similarity	NPC134621
0.9324	High Similarity	NPC89625
0.9324	High Similarity	NPC149618
0.932	High Similarity	NPC217447
0.932	High Similarity	NPC175978
0.9315	High Similarity	NPC158866
0.9315	High Similarity	NPC119929
0.9306	High Similarity	NPC237208
0.9301	High Similarity	NPC95123
0.9301	High Similarity	NPC42540
0.9301	High Similarity	NPC151607
0.9301	High Similarity	NPC66404
0.9296	High Similarity	NPC49108
0.9291	High Similarity	NPC168471
0.9291	High Similarity	NPC472366
0.9281	High Similarity	NPC118919
0.9281	High Similarity	NPC158481
0.9262	High Similarity	NPC146211
0.9247	High Similarity	NPC288036
0.9247	High Similarity	NPC97029
0.9247	High Similarity	NPC65589
0.9247	High Similarity	NPC158338
0.9247	High Similarity	NPC100985
0.9247	High Similarity	NPC97028
0.9241	High Similarity	NPC190648
0.9241	High Similarity	NPC56433
0.9241	High Similarity	NPC312929
0.9241	High Similarity	NPC118027
0.9241	High Similarity	NPC289042
0.9241	High Similarity	NPC245584
0.9241	High Similarity	NPC126767
0.9236	High Similarity	NPC29577
0.9231	High Similarity	NPC159721
0.9225	High Similarity	NPC1704
0.9225	High Similarity	NPC67650
0.9225	High Similarity	NPC475730
0.9214	High Similarity	NPC194579
0.9209	High Similarity	NPC180905
0.9209	High Similarity	NPC182496
0.92	High Similarity	NPC263483
0.9184	High Similarity	NPC470568
0.9184	High Similarity	NPC255641
0.9184	High Similarity	NPC150928
0.9184	High Similarity	NPC290954
0.9178	High Similarity	NPC7025
0.9178	High Similarity	NPC27221
0.9178	High Similarity	NPC256672
0.9172	High Similarity	NPC25844
0.9172	High Similarity	NPC473927
0.9161	High Similarity	NPC126534
0.9161	High Similarity	NPC105648
0.9161	High Similarity	NPC40118
0.9161	High Similarity	NPC474385
0.9161	High Similarity	NPC232021
0.9155	High Similarity	NPC109232
0.9143	High Similarity	NPC13575
0.9139	High Similarity	NPC474373
0.9128	High Similarity	NPC169990
0.9128	High Similarity	NPC210942
0.9128	High Similarity	NPC472799
0.9128	High Similarity	NPC329844
0.9122	High Similarity	NPC474417
0.9122	High Similarity	NPC470569
0.9122	High Similarity	NPC478148
0.9122	High Similarity	NPC232645
0.9122	High Similarity	NPC149526
0.9122	High Similarity	NPC72958
0.9116	High Similarity	NPC476684
0.911	High Similarity	NPC137296
0.911	High Similarity	NPC22005
0.911	High Similarity	NPC7943
0.911	High Similarity	NPC123202
0.9103	High Similarity	NPC75694
0.9097	High Similarity	NPC51106
0.9097	High Similarity	NPC469542
0.9097	High Similarity	NPC471731
0.9097	High Similarity	NPC472006
0.9097	High Similarity	NPC297600
0.9091	High Similarity	NPC265178
0.9091	High Similarity	NPC220106
0.9091	High Similarity	NPC11056
0.9085	High Similarity	NPC21350
0.9085	High Similarity	NPC472368
0.9079	High Similarity	NPC143050
0.9078	High Similarity	NPC150399
0.9078	High Similarity	NPC98115
0.9078	High Similarity	NPC25287
0.9078	High Similarity	NPC477243
0.9078	High Similarity	NPC477242
0.9078	High Similarity	NPC477244
0.9078	High Similarity	NPC135837
0.9078	High Similarity	NPC168105
0.9078	High Similarity	NPC1486
0.9078	High Similarity	NPC186838
0.9078	High Similarity	NPC249606
0.9078	High Similarity	NPC12165
0.9078	High Similarity	NPC472364
0.9078	High Similarity	NPC274109
0.9078	High Similarity	NPC473391
0.9078	High Similarity	NPC472367
0.9078	High Similarity	NPC66349
0.9078	High Similarity	NPC476333
0.9078	High Similarity	NPC41461
0.9071	High Similarity	NPC103842
0.9067	High Similarity	NPC226656
0.9067	High Similarity	NPC66508
0.906	High Similarity	NPC87708
0.906	High Similarity	NPC271681
0.906	High Similarity	NPC40356
0.906	High Similarity	NPC154683
0.9054	High Similarity	NPC60413
0.9054	High Similarity	NPC294646
0.9054	High Similarity	NPC325983
0.9054	High Similarity	NPC147735
0.9041	High Similarity	NPC138978
0.9041	High Similarity	NPC267509
0.9034	High Similarity	NPC86373
0.9034	High Similarity	NPC280404
0.9034	High Similarity	NPC210425
0.9034	High Similarity	NPC19896
0.9034	High Similarity	NPC277426
0.9028	High Similarity	NPC469579
0.9028	High Similarity	NPC471733
0.9021	High Similarity	NPC99441
0.9021	High Similarity	NPC472600
0.9021	High Similarity	NPC477956
0.9021	High Similarity	NPC472601
0.9014	High Similarity	NPC317119
0.9014	High Similarity	NPC472419
0.9014	High Similarity	NPC153979
0.9007	High Similarity	NPC156092
0.9007	High Similarity	NPC50455
0.9007	High Similarity	NPC131039
0.9007	High Similarity	NPC4547
0.9	High Similarity	NPC204960
0.9	High Similarity	NPC294593
0.9	High Similarity	NPC159623
0.9	High Similarity	NPC208806
0.9	High Similarity	NPC18877
0.9	High Similarity	NPC28753
0.9	High Similarity	NPC20560
0.9	High Similarity	NPC82225
0.9	High Similarity	NPC144051
0.9	High Similarity	NPC93552
0.8993	High Similarity	NPC258249
0.8986	High Similarity	NPC10027
0.8986	High Similarity	NPC6923
0.8986	High Similarity	NPC65775
0.898	High Similarity	NPC12305
0.898	High Similarity	NPC8817
0.8973	High Similarity	NPC49282
0.8973	High Similarity	NPC472034
0.8973	High Similarity	NPC312789
0.8973	High Similarity	NPC32470
0.8973	High Similarity	NPC473692
0.8966	High Similarity	NPC167663
0.8966	High Similarity	NPC310340
0.8958	High Similarity	NPC37530
0.8958	High Similarity	NPC172250
0.8958	High Similarity	NPC215311
0.8958	High Similarity	NPC144118
0.8958	High Similarity	NPC472605
0.8958	High Similarity	NPC213659
0.8958	High Similarity	NPC259166
0.8958	High Similarity	NPC80962
0.8958	High Similarity	NPC158634
0.8958	High Similarity	NPC48624
0.8958	High Similarity	NPC326109
0.8958	High Similarity	NPC472604
0.8958	High Similarity	NPC472603
0.8958	High Similarity	NPC219917
0.8958	High Similarity	NPC204985
0.8951	High Similarity	NPC251681
0.8951	High Similarity	NPC243528
0.8947	High Similarity	NPC246647
0.8947	High Similarity	NPC212967
0.8947	High Similarity	NPC96342
0.8947	High Similarity	NPC164110
0.8944	High Similarity	NPC70380
0.8944	High Similarity	NPC213603
0.8944	High Similarity	NPC24394
0.8936	High Similarity	NPC290803
0.8936	High Similarity	NPC286336

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 NPC163846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	980
0.2-0.3	1497
0.3-0.4	2538
0.4-0.5	1946
0.5-0.6	1167
0.6-0.7	485
0.7-0.8	176
0.8-0.85	34
0.85-0.9	8
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9103	High Similarity	NPD2534	Approved
0.9103	High Similarity	NPD2533	Approved
0.9103	High Similarity	NPD2532	Approved
0.9085	High Similarity	NPD6232	Discontinued
0.9085	High Similarity	NPD970	Clinical (unspecified phase)
0.9	High Similarity	NPD7819	Suspended
0.891	High Similarity	NPD7473	Discontinued
0.8865	High Similarity	NPD1607	Approved
0.8811	High Similarity	NPD2935	Discontinued
0.8723	High Similarity	NPD1240	Approved
0.8716	High Similarity	NPD4378	Clinical (unspecified phase)
0.8611	High Similarity	NPD1510	Phase 2
0.8535	High Similarity	NPD6959	Discontinued
0.8506	High Similarity	NPD2393	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD7411	Suspended
0.8483	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7075	Discontinued
0.8446	Intermediate Similarity	NPD3750	Approved
0.8431	Intermediate Similarity	NPD6599	Discontinued
0.8425	Intermediate Similarity	NPD1551	Phase 2
0.8397	Intermediate Similarity	NPD7768	Phase 2
0.8387	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD3226	Approved
0.8365	Intermediate Similarity	NPD5711	Approved
0.8365	Intermediate Similarity	NPD5710	Approved
0.8344	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5844	Phase 1
0.8333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD4380	Phase 2
0.8311	Intermediate Similarity	NPD1549	Phase 2
0.8299	Intermediate Similarity	NPD5406	Approved
0.8299	Intermediate Similarity	NPD5405	Approved
0.8299	Intermediate Similarity	NPD5408	Approved
0.8299	Intermediate Similarity	NPD5404	Approved
0.8278	Intermediate Similarity	NPD6799	Approved
0.8278	Intermediate Similarity	NPD7390	Discontinued
0.8261	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD2346	Discontinued
0.8228	Intermediate Similarity	NPD3749	Approved
0.8205	Intermediate Similarity	NPD6801	Discontinued
0.8205	Intermediate Similarity	NPD1934	Approved
0.8194	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD2796	Approved
0.8158	Intermediate Similarity	NPD1511	Approved
0.8156	Intermediate Similarity	NPD1283	Approved
0.8153	Intermediate Similarity	NPD2801	Approved
0.8133	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD2799	Discontinued
0.8108	Intermediate Similarity	NPD3748	Approved
0.8101	Intermediate Similarity	NPD3817	Phase 2
0.8095	Intermediate Similarity	NPD6651	Approved
0.8079	Intermediate Similarity	NPD7003	Approved
0.8079	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD4628	Phase 3
0.8058	Intermediate Similarity	NPD4626	Approved
0.8052	Intermediate Similarity	NPD1512	Approved
0.805	Intermediate Similarity	NPD3882	Suspended
0.8013	Intermediate Similarity	NPD2800	Approved
0.8013	Intermediate Similarity	NPD1243	Approved
0.7964	Intermediate Similarity	NPD6559	Discontinued
0.7943	Intermediate Similarity	NPD1281	Approved
0.7937	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6099	Approved
0.7933	Intermediate Similarity	NPD6100	Approved
0.7904	Intermediate Similarity	NPD5953	Discontinued
0.7898	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD920	Approved
0.7877	Intermediate Similarity	NPD4625	Phase 3
0.7861	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1203	Approved
0.7838	Intermediate Similarity	NPD943	Approved
0.7818	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6166	Phase 2
0.7818	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD1201	Approved
0.7812	Intermediate Similarity	NPD1465	Phase 2
0.7791	Intermediate Similarity	NPD5494	Approved
0.7785	Intermediate Similarity	NPD7458	Discontinued
0.7784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7286	Phase 2
0.7771	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1608	Approved
0.7756	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD37	Approved
0.7738	Intermediate Similarity	NPD7074	Phase 3
0.773	Intermediate Similarity	NPD1651	Approved
0.773	Intermediate Similarity	NPD5691	Approved
0.773	Intermediate Similarity	NPD919	Approved
0.7725	Intermediate Similarity	NPD3818	Discontinued
0.7724	Intermediate Similarity	NPD1164	Approved
0.7724	Intermediate Similarity	NPD1470	Approved
0.7718	Intermediate Similarity	NPD2979	Phase 3
0.7703	Intermediate Similarity	NPD3764	Approved
0.7703	Intermediate Similarity	NPD2313	Discontinued
0.7703	Intermediate Similarity	NPD411	Approved
0.7697	Intermediate Similarity	NPD7229	Phase 3
0.7687	Intermediate Similarity	NPD6832	Phase 2
0.7679	Intermediate Similarity	NPD7054	Approved
0.7671	Intermediate Similarity	NPD2798	Approved
0.7667	Intermediate Similarity	NPD230	Phase 1
0.7658	Intermediate Similarity	NPD5403	Approved
0.7654	Intermediate Similarity	NPD5402	Approved
0.7647	Intermediate Similarity	NPD2344	Approved
0.7644	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD9493	Approved
0.7639	Intermediate Similarity	NPD9717	Approved
0.7639	Intermediate Similarity	NPD3972	Approved
0.7633	Intermediate Similarity	NPD7472	Approved
0.7632	Intermediate Similarity	NPD4308	Phase 3
0.7622	Intermediate Similarity	NPD6234	Discontinued
0.7619	Intermediate Similarity	NPD7177	Discontinued
0.7607	Intermediate Similarity	NPD4967	Phase 2
0.7607	Intermediate Similarity	NPD4965	Approved
0.7607	Intermediate Similarity	NPD4966	Approved
0.7603	Intermediate Similarity	NPD2797	Approved
0.7602	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4060	Phase 1
0.7588	Intermediate Similarity	NPD6797	Phase 2
0.7584	Intermediate Similarity	NPD3268	Approved
0.7584	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2438	Suspended
0.758	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD422	Phase 1
0.7558	Intermediate Similarity	NPD8312	Approved
0.7558	Intermediate Similarity	NPD8313	Approved
0.7552	Intermediate Similarity	NPD17	Approved
0.755	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4288	Approved
0.7544	Intermediate Similarity	NPD7251	Discontinued
0.7535	Intermediate Similarity	NPD9545	Approved
0.7532	Intermediate Similarity	NPD5401	Approved
0.753	Intermediate Similarity	NPD7199	Phase 2
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7808	Phase 3
0.7484	Intermediate Similarity	NPD6273	Approved
0.7468	Intermediate Similarity	NPD2531	Phase 2
0.7468	Intermediate Similarity	NPD4476	Approved
0.7468	Intermediate Similarity	NPD4477	Approved
0.7467	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2309	Approved
0.745	Intermediate Similarity	NPD4908	Phase 1
0.744	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3926	Phase 2
0.7436	Intermediate Similarity	NPD2654	Approved
0.7434	Intermediate Similarity	NPD447	Suspended
0.7432	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7435	Discontinued
0.7429	Intermediate Similarity	NPD8150	Discontinued
0.7421	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8151	Discontinued
0.7384	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4307	Phase 2
0.7363	Intermediate Similarity	NPD6777	Approved
0.7363	Intermediate Similarity	NPD6780	Approved
0.7363	Intermediate Similarity	NPD6778	Approved
0.7363	Intermediate Similarity	NPD6779	Approved
0.7363	Intermediate Similarity	NPD6781	Approved
0.7363	Intermediate Similarity	NPD6782	Approved
0.7363	Intermediate Similarity	NPD6776	Approved
0.7362	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4749	Approved
0.7329	Intermediate Similarity	NPD1610	Phase 2
0.7321	Intermediate Similarity	NPD1247	Approved
0.732	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5124	Phase 1
0.731	Intermediate Similarity	NPD1778	Approved
0.731	Intermediate Similarity	NPD7228	Approved
0.731	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1471	Phase 3
0.7297	Intermediate Similarity	NPD1876	Approved
0.7297	Intermediate Similarity	NPD3225	Approved
0.7285	Intermediate Similarity	NPD3027	Phase 3
0.7268	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6746	Phase 2
0.7249	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7783	Phase 2
0.7248	Intermediate Similarity	NPD3267	Approved
0.7248	Intermediate Similarity	NPD3266	Approved
0.7247	Intermediate Similarity	NPD4287	Approved
0.7243	Intermediate Similarity	NPD7696	Phase 3
0.7243	Intermediate Similarity	NPD7698	Approved
0.7243	Intermediate Similarity	NPD7697	Approved
0.7237	Intermediate Similarity	NPD1296	Phase 2
0.7237	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5242	Approved
0.7211	Intermediate Similarity	NPD1611	Approved
0.7208	Intermediate Similarity	NPD1933	Approved
0.7208	Intermediate Similarity	NPD6355	Discontinued
0.7204	Intermediate Similarity	NPD7870	Phase 2
0.7204	Intermediate Similarity	NPD7871	Phase 2
0.7198	Intermediate Similarity	NPD8090	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