NPASS Compound

Structure

CID50221 OpenBabel06191715382D 24 25 0 0 1 0 0 0 0 0999 V2000 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -2.5981 -1.5000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -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 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 1.8660 0.0000 C 0 0 0 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 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -5.1962 -0.0000 0.0000 O 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 1.0000 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 5 2 0 0 0 0 1 6 1 0 0 0 0 2 5 1 0 0 0 0 2 7 2 0 0 0 0 3 8 1 0 0 0 0 3 14 1 0 0 0 0 4 9 1 0 0 0 0 4 14 1 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 1 0 0 0 9 11 1 0 0 0 0 9 24 1 6 0 0 0 10 18 1 0 0 0 0 11 19 1 1 0 0 0 12 20 2 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 21 2 0 0 0 0 13 22 1 0 0 0 0 14 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.07
Volume:	308.307
LogP:	-0.193
LogD:	-0.226
LogS:	-0.88
# Rotatable Bonds:	4
TPSA:	184.98
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.256
Synthetic Accessibility Score:	3.902
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.509
MDCK Permeability:	6.642672815360129e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.485
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.266
Plasma Protein Binding (PPB):	67.60139465332031%
Volume Distribution (VD):	0.7
Pgp-substrate:	36.667118072509766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.098
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	2.61
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.459
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.141
Carcinogencity:	0.008
Eye Corrosion:	0.005
Eye Irritation:	0.322
Respiratory Toxicity:	0.042

Download Data

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

Natural Product: NPC50221

Natural Product ID:	NPC50221
*Common Name:**	3-O-Galloyl-Quinic Acid
IUPAC Name:	(1S,3R,4R,5R)-1,3,4-trihydroxy-5-(3,4,5-trihydroxybenzoyl)oxycyclohexane-1-carboxylic acid
Synonyms:
Standard InCHIKey:	LDPLFHGGZNSKDS-FTBFGRRBSA-N
Standard InCHI:	InChI=1S/C14H16O10/c15-6-1-5(2-7(16)10(6)18)12(20)24-9-4-14(23,13(21)22)3-8(17)11(9)19/h1-2,8-9,11,15-19,23H,3-4H2,(H,21,22)/t8-,9-,11-,14+/m1/s1
SMILES:	O[C@@H]1C[C@](O)(C[C@H]([C@@H]1O)OC(=O)c1cc(O)c(c(c1)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3233512
PubChem CID:	442988
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives [CHEMONTID:0002509] Cyclitols and derivatives [CHEMONTID:0002512] Quinic acids and derivatives

*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
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Gansu province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Henan province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shandong province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19721258]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19772486]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20806783]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21782011]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22190295]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO33051	mango tree	n.a.	n.a.	n.a.	stem bark	n.a.	n.a.	PMID[24613627]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[26838074]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27313650]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27429639]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29741372]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	HeZe, ShanDong, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32951423]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Xinjiang,China		PMID[33063333]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7690	Nyssa sinensis	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7690	Nyssa sinensis	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22543	Cleome chrysantha	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7690	Nyssa sinensis	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9757	Cladonia macilenta	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7292	Excoecaria kawakamii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8313	Rhipocephalus phoenix	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2461	Perilla acuta	Species	Araneidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8848	Colubrina elliptica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7862	Faramea cyanea	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1496	Stevia porphyrea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21977	Psora corallina	Species	Psoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20026	Senecio callosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	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
Others	2

Activity Type	# Activity
Individual Protein	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3084	Individual Protein	Neuraminidase	Influenza A virus	Inhibition	=	33.2	%	PMID[550752]
NPT24971	SINGLE PROTEIN	Genome polyprotein	Coxsackievirus B3 (strain Nancy)	Inhibition	=	29.8	%	PMID[550752]

☑ 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 NPC50221 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	339
0.1-0.2	1435
0.2-0.3	3732
0.3-0.4	8228
0.4-0.5	9887
0.5-0.6	4600
0.6-0.7	6894
0.7-0.8	6970
0.8-0.85	440
0.85-0.9	98
0.9-0.95	65
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC114242
0.9714	High Similarity	NPC43123
0.9645	High Similarity	NPC42464
0.9577	High Similarity	NPC306343
0.9562	High Similarity	NPC105525
0.9562	High Similarity	NPC75763
0.9562	High Similarity	NPC12218
0.9562	High Similarity	NPC225036
0.9489	High Similarity	NPC239943
0.9429	High Similarity	NPC121573
0.9429	High Similarity	NPC226738
0.9429	High Similarity	NPC190587
0.9429	High Similarity	NPC22176
0.9375	High Similarity	NPC252979
0.9348	High Similarity	NPC37250
0.9348	High Similarity	NPC278068
0.9348	High Similarity	NPC142703
0.9348	High Similarity	NPC219428
0.9348	High Similarity	NPC302857
0.9348	High Similarity	NPC152942
0.9291	High Similarity	NPC229036
0.9281	High Similarity	NPC303683
0.9281	High Similarity	NPC476820
0.9281	High Similarity	NPC274891
0.9281	High Similarity	NPC295492
0.9281	High Similarity	NPC205751
0.9281	High Similarity	NPC476819
0.9281	High Similarity	NPC26241
0.9281	High Similarity	NPC474875
0.9252	High Similarity	NPC145425
0.9236	High Similarity	NPC75945
0.9225	High Similarity	NPC108455
0.9167	High Similarity	NPC248257
0.9167	High Similarity	NPC142528
0.9167	High Similarity	NPC120621
0.9149	High Similarity	NPC35702
0.9149	High Similarity	NPC471027
0.9149	High Similarity	NPC477335
0.9149	High Similarity	NPC13818
0.9149	High Similarity	NPC297517
0.9149	High Similarity	NPC206095
0.9149	High Similarity	NPC224389
0.913	High Similarity	NPC18646
0.9124	High Similarity	NPC156124
0.9124	High Similarity	NPC1321
0.9124	High Similarity	NPC304929
0.9103	High Similarity	NPC92117
0.9085	High Similarity	NPC303090
0.9085	High Similarity	NPC258469
0.9085	High Similarity	NPC284948
0.9085	High Similarity	NPC277315
0.9085	High Similarity	NPC472016
0.9085	High Similarity	NPC319628
0.9085	High Similarity	NPC220664
0.9085	High Similarity	NPC192831
0.9085	High Similarity	NPC37331
0.9085	High Similarity	NPC43158
0.9065	High Similarity	NPC156892
0.906	High Similarity	NPC134925
0.9058	High Similarity	NPC68517
0.9048	High Similarity	NPC93498
0.9048	High Similarity	NPC163883
0.9028	High Similarity	NPC98356
0.8993	High Similarity	NPC70680
0.8993	High Similarity	NPC233350
0.8993	High Similarity	NPC182217
0.8986	High Similarity	NPC146277
0.8986	High Similarity	NPC19380
0.898	High Similarity	NPC140151
0.8978	High Similarity	NPC264145
0.8966	High Similarity	NPC229264
0.8919	High Similarity	NPC75695
0.8904	High Similarity	NPC471076
0.8904	High Similarity	NPC192568
0.8867	High Similarity	NPC203757
0.8859	High Similarity	NPC61152
0.8859	High Similarity	NPC44260
0.8859	High Similarity	NPC16024
0.8859	High Similarity	NPC205037
0.8859	High Similarity	NPC3746
0.8836	High Similarity	NPC268366
0.8828	High Similarity	NPC477333
0.8803	High Similarity	NPC283560
0.8803	High Similarity	NPC24295
0.8784	High Similarity	NPC473091
0.8767	High Similarity	NPC473867
0.8759	High Similarity	NPC134975
0.8742	High Similarity	NPC156624
0.8742	High Similarity	NPC172920
0.8733	High Similarity	NPC105827
0.8733	High Similarity	NPC310661
0.8732	High Similarity	NPC25305
0.8732	High Similarity	NPC125417
0.8732	High Similarity	NPC112068
0.8732	High Similarity	NPC95679
0.8732	High Similarity	NPC110899
0.8707	High Similarity	NPC322660
0.8696	High Similarity	NPC226855
0.8696	High Similarity	NPC94810
0.8693	High Similarity	NPC74319
0.8693	High Similarity	NPC287872
0.8684	High Similarity	NPC247629
0.8684	High Similarity	NPC239019
0.8652	High Similarity	NPC474895
0.8649	High Similarity	NPC472969
0.8636	High Similarity	NPC119125
0.8636	High Similarity	NPC166277
0.8627	High Similarity	NPC4747
0.8627	High Similarity	NPC472860
0.8627	High Similarity	NPC172419
0.8627	High Similarity	NPC104275
0.8627	High Similarity	NPC238419
0.8627	High Similarity	NPC1913
0.8581	High Similarity	NPC472859
0.8581	High Similarity	NPC25389
0.8581	High Similarity	NPC311803
0.8571	High Similarity	NPC289811
0.8571	High Similarity	NPC160780
0.8562	High Similarity	NPC104983
0.8562	High Similarity	NPC300845
0.8562	High Similarity	NPC250436
0.8562	High Similarity	NPC291948
0.8562	High Similarity	NPC88803
0.8553	High Similarity	NPC197188
0.8553	High Similarity	NPC125487
0.8553	High Similarity	NPC291510
0.8553	High Similarity	NPC238672
0.8553	High Similarity	NPC116850
0.8553	High Similarity	NPC475058
0.8553	High Similarity	NPC144801
0.8553	High Similarity	NPC43872
0.8553	High Similarity	NPC281703
0.8551	High Similarity	NPC158654
0.8543	High Similarity	NPC221249
0.8543	High Similarity	NPC246566
0.8543	High Similarity	NPC227485
0.8543	High Similarity	NPC95498
0.8531	High Similarity	NPC475111
0.8526	High Similarity	NPC90905
0.8526	High Similarity	NPC4013
0.8521	High Similarity	NPC155098
0.8521	High Similarity	NPC248150
0.8516	High Similarity	NPC289346
0.8516	High Similarity	NPC239966
0.8516	High Similarity	NPC24164
0.8516	High Similarity	NPC24627
0.8516	High Similarity	NPC203020
0.8514	High Similarity	NPC262282
0.8511	High Similarity	NPC18074
0.8511	High Similarity	NPC61
0.8511	High Similarity	NPC25581
0.8511	High Similarity	NPC5419
0.8506	High Similarity	NPC68324
0.8506	High Similarity	NPC49173
0.8506	High Similarity	NPC160512
0.8506	High Similarity	NPC156818
0.8506	High Similarity	NPC289322
0.8506	High Similarity	NPC135222
0.8506	High Similarity	NPC38779
0.8506	High Similarity	NPC474010
0.8506	High Similarity	NPC114179
0.8503	High Similarity	NPC474692
0.8491	Intermediate Similarity	NPC476017
0.8483	Intermediate Similarity	NPC156709
0.8483	Intermediate Similarity	NPC179505
0.8477	Intermediate Similarity	NPC477334
0.8467	Intermediate Similarity	NPC107636
0.8467	Intermediate Similarity	NPC476394
0.8467	Intermediate Similarity	NPC98809
0.8456	Intermediate Similarity	NPC225710
0.8452	Intermediate Similarity	NPC87317
0.8452	Intermediate Similarity	NPC318826
0.8452	Intermediate Similarity	NPC210501
0.8452	Intermediate Similarity	NPC114791
0.8452	Intermediate Similarity	NPC104222
0.8452	Intermediate Similarity	NPC141331
0.8451	Intermediate Similarity	NPC155209
0.8451	Intermediate Similarity	NPC168799
0.8451	Intermediate Similarity	NPC288743
0.8442	Intermediate Similarity	NPC318432
0.8442	Intermediate Similarity	NPC470896
0.8442	Intermediate Similarity	NPC473275
0.844	Intermediate Similarity	NPC198388
0.8431	Intermediate Similarity	NPC287504
0.8431	Intermediate Similarity	NPC281477
0.8414	Intermediate Similarity	NPC207516
0.8408	Intermediate Similarity	NPC33298
0.8408	Intermediate Similarity	NPC291957
0.8408	Intermediate Similarity	NPC285108
0.8408	Intermediate Similarity	NPC14030
0.8408	Intermediate Similarity	NPC41009
0.84	Intermediate Similarity	NPC294972
0.84	Intermediate Similarity	NPC476463
0.84	Intermediate Similarity	NPC81835
0.8397	Intermediate Similarity	NPC53889
0.8397	Intermediate Similarity	NPC476373
0.8392	Intermediate Similarity	NPC106406
0.8389	Intermediate Similarity	NPC474465
0.8378	Intermediate Similarity	NPC473090
0.8377	Intermediate Similarity	NPC82592

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 NPC50221 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	849
0.2-0.3	1929
0.3-0.4	2725
0.4-0.5	1902
0.5-0.6	956
0.6-0.7	400
0.7-0.8	90
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9124	High Similarity	NPD230	Phase 1
0.9085	High Similarity	NPD6190	Approved
0.8562	High Similarity	NPD4868	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD9269	Phase 2
0.8272	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD9268	Approved
0.8089	Intermediate Similarity	NPD3882	Suspended
0.8025	Intermediate Similarity	NPD3817	Phase 2
0.7975	Intermediate Similarity	NPD3818	Discontinued
0.7974	Intermediate Similarity	NPD1512	Approved
0.7963	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6166	Phase 2
0.7963	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1465	Phase 2
0.7962	Intermediate Similarity	NPD2801	Approved
0.7911	Intermediate Similarity	NPD5402	Approved
0.7898	Intermediate Similarity	NPD1934	Approved
0.7877	Intermediate Similarity	NPD943	Approved
0.7848	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1511	Approved
0.7831	Intermediate Similarity	NPD6797	Phase 2
0.7826	Intermediate Similarity	NPD9545	Approved
0.7812	Intermediate Similarity	NPD7075	Discontinued
0.7785	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7251	Discontinued
0.7771	Intermediate Similarity	NPD4380	Phase 2
0.7756	Intermediate Similarity	NPD1653	Approved
0.7727	Intermediate Similarity	NPD6799	Approved
0.7711	Intermediate Similarity	NPD5844	Phase 1
0.7711	Intermediate Similarity	NPD7054	Approved
0.7682	Intermediate Similarity	NPD7266	Discontinued
0.7679	Intermediate Similarity	NPD7685	Pre-registration
0.7673	Intermediate Similarity	NPD6801	Discontinued
0.7665	Intermediate Similarity	NPD7472	Approved
0.7665	Intermediate Similarity	NPD7074	Phase 3
0.7655	Intermediate Similarity	NPD9494	Approved
0.7647	Intermediate Similarity	NPD4628	Phase 3
0.7633	Intermediate Similarity	NPD7808	Phase 3
0.7632	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6232	Discontinued
0.7602	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD5403	Approved
0.7578	Intermediate Similarity	NPD5353	Approved
0.7551	Intermediate Similarity	NPD3027	Phase 3
0.7546	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7453	Intermediate Similarity	NPD37	Approved
0.7452	Intermediate Similarity	NPD5401	Approved
0.7438	Intermediate Similarity	NPD6599	Discontinued
0.7434	Intermediate Similarity	NPD1510	Phase 2
0.7423	Intermediate Similarity	NPD4965	Approved
0.7423	Intermediate Similarity	NPD4967	Phase 2
0.7423	Intermediate Similarity	NPD4966	Approved
0.7403	Intermediate Similarity	NPD1549	Phase 2
0.74	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1613	Approved
0.7386	Intermediate Similarity	NPD1551	Phase 2
0.7383	Intermediate Similarity	NPD3764	Approved
0.7375	Intermediate Similarity	NPD3455	Phase 2
0.7356	Intermediate Similarity	NPD8150	Discontinued
0.7351	Intermediate Similarity	NPD447	Suspended
0.7342	Intermediate Similarity	NPD2532	Approved
0.7342	Intermediate Similarity	NPD2534	Approved
0.7342	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2533	Approved
0.7338	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7228	Approved
0.7301	Intermediate Similarity	NPD7819	Suspended
0.7294	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5494	Approved
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1240	Approved
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2935	Discontinued
0.7267	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5242	Approved
0.7235	Intermediate Similarity	NPD3751	Discontinued
0.7229	Intermediate Similarity	NPD919	Approved
0.7197	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3750	Approved
0.719	Intermediate Similarity	NPD1607	Approved
0.7181	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6386	Approved
0.7178	Intermediate Similarity	NPD7411	Suspended
0.7178	Intermediate Similarity	NPD6385	Approved
0.7168	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7153	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD1247	Approved
0.7133	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7089	Intermediate Similarity	NPD8166	Discontinued
0.7079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9493	Approved
0.7059	Intermediate Similarity	NPD3926	Phase 2
0.7051	Intermediate Similarity	NPD2796	Approved
0.7025	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3749	Approved
0.6946	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6959	Discontinued
0.6933	Remote Similarity	NPD1203	Approved
0.6923	Remote Similarity	NPD6535	Approved
0.6923	Remote Similarity	NPD6534	Approved
0.6919	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7768	Phase 2
0.6898	Remote Similarity	NPD7435	Discontinued
0.6879	Remote Similarity	NPD3748	Approved
0.6875	Remote Similarity	NPD7240	Approved
0.6852	Remote Similarity	NPD4357	Discontinued
0.6846	Remote Similarity	NPD1608	Approved
0.6835	Remote Similarity	NPD9570	Approved
0.6832	Remote Similarity	NPD3887	Approved
0.6832	Remote Similarity	NPD2354	Approved
0.6829	Remote Similarity	NPD920	Approved
0.6828	Remote Similarity	NPD6782	Approved
0.6828	Remote Similarity	NPD6781	Approved
0.6828	Remote Similarity	NPD6777	Approved
0.6828	Remote Similarity	NPD6780	Approved
0.6828	Remote Similarity	NPD6778	Approved
0.6828	Remote Similarity	NPD6776	Approved
0.6828	Remote Similarity	NPD6779	Approved
0.6818	Remote Similarity	NPD6798	Discontinued
0.6818	Remote Similarity	NPD5953	Discontinued
0.6813	Remote Similarity	NPD1652	Phase 2
0.6811	Remote Similarity	NPD7700	Phase 2
0.6811	Remote Similarity	NPD7699	Phase 2
0.681	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.681	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5711	Approved
0.6802	Remote Similarity	NPD5710	Approved
0.6795	Remote Similarity	NPD6355	Discontinued
0.678	Remote Similarity	NPD7039	Approved
0.678	Remote Similarity	NPD7038	Approved
0.6779	Remote Similarity	NPD422	Phase 1
0.6774	Remote Similarity	NPD4062	Phase 3
0.6772	Remote Similarity	NPD8320	Phase 1
0.6772	Remote Similarity	NPD8319	Approved
0.6757	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7390	Discontinued
0.6744	Remote Similarity	NPD8127	Discontinued
0.6733	Remote Similarity	NPD1481	Phase 2
0.6733	Remote Similarity	NPD9717	Approved
0.6731	Remote Similarity	NPD825	Approved
0.6731	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD826	Approved
0.673	Remote Similarity	NPD6099	Approved
0.673	Remote Similarity	NPD6100	Approved
0.6719	Remote Similarity	NPD8151	Discontinued
0.6708	Remote Similarity	NPD1243	Approved
0.6708	Remote Similarity	NPD2800	Approved
0.6707	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3146	Approved
0.6705	Remote Similarity	NPD7286	Phase 2
0.6704	Remote Similarity	NPD8312	Approved
0.6704	Remote Similarity	NPD8313	Approved
0.669	Remote Similarity	NPD2629	Approved
0.6689	Remote Similarity	NPD2983	Phase 2
0.6689	Remote Similarity	NPD2982	Phase 2
0.6688	Remote Similarity	NPD1933	Approved
0.6688	Remote Similarity	NPD6832	Phase 2
0.6688	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD8368	Discontinued
0.6684	Remote Similarity	NPD7874	Approved
0.6684	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD5536	Phase 2
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD1535	Discovery
0.6649	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD824	Approved
0.6647	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3226	Approved
0.6646	Remote Similarity	NPD6651	Approved
0.6645	Remote Similarity	NPD7095	Approved
0.6644	Remote Similarity	NPD17	Approved
0.6632	Remote Similarity	NPD7698	Approved
0.6632	Remote Similarity	NPD7697	Approved
0.6632	Remote Similarity	NPD7696	Phase 3
0.6625	Remote Similarity	NPD5406	Approved
0.6625	Remote Similarity	NPD5408	Approved
0.6625	Remote Similarity	NPD5404	Approved
0.6625	Remote Similarity	NPD5405	Approved
0.6624	Remote Similarity	NPD4060	Phase 1

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