NPASS Compound

Structure

CID319995 OpenBabel06191716152D 37 40 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 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 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 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 7.7942 -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 -0.0000 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 6.9282 -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 2 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 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 6.0622 0.5000 0.0000 C 0 0 1 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 6.9282 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 2 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 7.7942 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 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 6.0622 1.5000 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 15 1 0 0 0 0 9 26 1 0 0 0 0 10 14 2 0 0 0 0 10 34 1 0 0 0 0 11 17 1 0 0 0 0 12 2 1 1 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 8 1 6 0 0 0 13 14 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 6 0 0 0 15 35 1 0 0 0 0 16 9 1 6 0 0 0 16 18 1 0 0 0 0 16 36 1 0 0 0 0 17 19 2 0 0 0 0 18 20 1 0 0 0 0 18 27 1 1 0 0 0 19 22 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 6 0 0 0 21 25 1 0 0 0 0 21 30 1 1 0 0 0 22 31 2 0 0 0 0 22 32 1 0 0 0 0 23 33 2 0 0 0 0 23 35 1 0 0 0 0 24 34 1 0 0 0 0 24 37 1 6 0 0 0 25 36 1 0 0 0 0 25 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.16
Volume:	491.121
LogP:	0.668
LogD:	0.163
LogS:	-1.917
# Rotatable Bonds:	8
TPSA:	189.28
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	4.996
Fsp3:	0.48
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.127
MDCK Permeability:	6.762870179954916e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.936
20% Bioavailability (F20%):	0.045
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	74.42342376708984%
Volume Distribution (VD):	0.316
Pgp-substrate:	13.281782150268555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.203
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	1.267
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.251
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.037
Carcinogencity:	0.648
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC319995

Natural Product ID:	NPC319995
*Common Name:**	Loniphenyruviridoside C
IUPAC Name:	(E)-3-[(3S,4aR,5R,6S)-5-ethenyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]-2-hydroxy-3-phenylprop-2-enoic acid
Synonyms:	Loniphenyruviridoside C
Standard InCHIKey:	JANONPLUBJJWRY-VOEIRARSSA-N
Standard InCHI:	InChI=1S/C25H28O12/c1-2-12-13-8-15(17(19(28)22(31)32)11-6-4-3-5-7-11)35-23(33)14(13)10-34-24(12)37-25-21(30)20(29)18(27)16(9-26)36-25/h2-7,10,12-13,15-16,18,20-21,24-30H,1,8-9H2,(H,31,32)/b19-17+/t12-,13-,15+,16-,18-,20+,21-,24+,25+/m1/s1
SMILES:	C=C[C@H]1[C@@H](OC=C2[C@@H]1C[C@H](OC2=O)/C(=C(C(=O)O)/O)/c1ccccc1)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928040
PubChem CID:	57398873
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001276] Phenylpyruvic acid 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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	Inhibition	=	30.9	%	PMID[538508]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	30.0	%	PMID[538508]

☑ 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 NPC319995 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	298
0.1-0.2	999
0.2-0.3	2173
0.3-0.4	5352
0.4-0.5	9760
0.5-0.6	14398
0.6-0.7	8102
0.7-0.8	1541
0.8-0.85	57
0.85-0.9	13
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC289415
0.968	High Similarity	NPC17567
0.8864	High Similarity	NPC470143
0.8864	High Similarity	NPC322503
0.8692	High Similarity	NPC231627
0.8636	High Similarity	NPC305162
0.8626	High Similarity	NPC226101
0.8626	High Similarity	NPC237182
0.8623	High Similarity	NPC284957
0.8511	High Similarity	NPC212808
0.8485	Intermediate Similarity	NPC301857
0.8473	Intermediate Similarity	NPC63404
0.8473	Intermediate Similarity	NPC114096
0.8473	Intermediate Similarity	NPC92283
0.8473	Intermediate Similarity	NPC290276
0.8473	Intermediate Similarity	NPC10883
0.8473	Intermediate Similarity	NPC231888
0.8473	Intermediate Similarity	NPC204214
0.8473	Intermediate Similarity	NPC35338
0.8473	Intermediate Similarity	NPC124878
0.8473	Intermediate Similarity	NPC10121
0.8473	Intermediate Similarity	NPC198918
0.8462	Intermediate Similarity	NPC244454
0.8462	Intermediate Similarity	NPC87153
0.8462	Intermediate Similarity	NPC162925
0.8462	Intermediate Similarity	NPC57607
0.845	Intermediate Similarity	NPC140561
0.845	Intermediate Similarity	NPC141970
0.8444	Intermediate Similarity	NPC136608
0.8444	Intermediate Similarity	NPC38420
0.8409	Intermediate Similarity	NPC148026
0.8397	Intermediate Similarity	NPC28069
0.8397	Intermediate Similarity	NPC77651
0.8394	Intermediate Similarity	NPC472132
0.8369	Intermediate Similarity	NPC296659
0.8369	Intermediate Similarity	NPC202391
0.8346	Intermediate Similarity	NPC471024
0.8333	Intermediate Similarity	NPC469364
0.8333	Intermediate Similarity	NPC101686
0.8333	Intermediate Similarity	NPC65262
0.8333	Intermediate Similarity	NPC475195
0.8321	Intermediate Similarity	NPC317163
0.831	Intermediate Similarity	NPC475528
0.8271	Intermediate Similarity	NPC471025
0.8252	Intermediate Similarity	NPC143246
0.8252	Intermediate Similarity	NPC475539
0.8252	Intermediate Similarity	NPC119773
0.8252	Intermediate Similarity	NPC474268
0.8248	Intermediate Similarity	NPC169398
0.8244	Intermediate Similarity	NPC473881
0.8239	Intermediate Similarity	NPC77922
0.8239	Intermediate Similarity	NPC473281
0.8226	Intermediate Similarity	NPC470825
0.8207	Intermediate Similarity	NPC96599
0.8195	Intermediate Similarity	NPC276047
0.8195	Intermediate Similarity	NPC471026
0.8195	Intermediate Similarity	NPC147032
0.8195	Intermediate Similarity	NPC267733
0.8182	Intermediate Similarity	NPC145287
0.8169	Intermediate Similarity	NPC293154
0.8151	Intermediate Similarity	NPC117346
0.8151	Intermediate Similarity	NPC240592
0.8148	Intermediate Similarity	NPC11025
0.8143	Intermediate Similarity	NPC31745
0.8143	Intermediate Similarity	NPC220936
0.813	Intermediate Similarity	NPC184633
0.8106	Intermediate Similarity	NPC138798
0.8095	Intermediate Similarity	NPC158546
0.8095	Intermediate Similarity	NPC289021
0.8095	Intermediate Similarity	NPC474641
0.8069	Intermediate Similarity	NPC473149
0.8028	Intermediate Similarity	NPC80098
0.8015	Intermediate Similarity	NPC253595
0.8	Intermediate Similarity	NPC476096
0.8	Intermediate Similarity	NPC471345
0.8	Intermediate Similarity	NPC175333
0.7986	Intermediate Similarity	NPC63304
0.7985	Intermediate Similarity	NPC123704
0.7973	Intermediate Similarity	NPC475379
0.7973	Intermediate Similarity	NPC474620
0.7959	Intermediate Similarity	NPC478236
0.7959	Intermediate Similarity	NPC329657
0.7959	Intermediate Similarity	NPC478234
0.7956	Intermediate Similarity	NPC475478
0.7919	Intermediate Similarity	NPC478235
0.7917	Intermediate Similarity	NPC475213
0.7917	Intermediate Similarity	NPC152796
0.7917	Intermediate Similarity	NPC478250
0.7917	Intermediate Similarity	NPC469367
0.7914	Intermediate Similarity	NPC114116
0.7899	Intermediate Similarity	NPC254819
0.7899	Intermediate Similarity	NPC235294
0.7899	Intermediate Similarity	NPC475569
0.7899	Intermediate Similarity	NPC46137
0.7891	Intermediate Similarity	NPC29607
0.7883	Intermediate Similarity	NPC27712
0.7881	Intermediate Similarity	NPC475484
0.7879	Intermediate Similarity	NPC229600
0.7868	Intermediate Similarity	NPC288416
0.7867	Intermediate Similarity	NPC229354
0.7862	Intermediate Similarity	NPC184464
0.7862	Intermediate Similarity	NPC251062
0.7857	Intermediate Similarity	NPC34456
0.7857	Intermediate Similarity	NPC43584
0.7852	Intermediate Similarity	NPC69425
0.7852	Intermediate Similarity	NPC79608
0.7847	Intermediate Similarity	NPC296643
0.7842	Intermediate Similarity	NPC269421
0.7829	Intermediate Similarity	NPC475378
0.7815	Intermediate Similarity	NPC477735
0.7815	Intermediate Similarity	NPC472128
0.7815	Intermediate Similarity	NPC472127
0.7812	Intermediate Similarity	NPC172525
0.7808	Intermediate Similarity	NPC477737
0.7808	Intermediate Similarity	NPC210330
0.78	Intermediate Similarity	NPC194705
0.7793	Intermediate Similarity	NPC111466
0.7793	Intermediate Similarity	NPC186296
0.7786	Intermediate Similarity	NPC19719
0.7786	Intermediate Similarity	NPC477281
0.7786	Intermediate Similarity	NPC477280
0.7785	Intermediate Similarity	NPC182350
0.7785	Intermediate Similarity	NPC69367
0.7778	Intermediate Similarity	NPC159387
0.7778	Intermediate Similarity	NPC7518
0.7778	Intermediate Similarity	NPC137501
0.7778	Intermediate Similarity	NPC187205
0.7778	Intermediate Similarity	NPC276061
0.7778	Intermediate Similarity	NPC79908
0.7778	Intermediate Similarity	NPC474148
0.7778	Intermediate Similarity	NPC154262
0.777	Intermediate Similarity	NPC246869
0.777	Intermediate Similarity	NPC138777
0.777	Intermediate Similarity	NPC23677
0.777	Intermediate Similarity	NPC225384
0.7763	Intermediate Similarity	NPC477736
0.7762	Intermediate Similarity	NPC476643
0.7761	Intermediate Similarity	NPC52097
0.7755	Intermediate Similarity	NPC291153
0.7755	Intermediate Similarity	NPC473147
0.774	Intermediate Similarity	NPC40085
0.774	Intermediate Similarity	NPC264270
0.774	Intermediate Similarity	NPC194938
0.774	Intermediate Similarity	NPC471028
0.7737	Intermediate Similarity	NPC106677
0.7727	Intermediate Similarity	NPC179914
0.7724	Intermediate Similarity	NPC31081
0.7724	Intermediate Similarity	NPC65833
0.7724	Intermediate Similarity	NPC245219
0.7724	Intermediate Similarity	NPC469527
0.7721	Intermediate Similarity	NPC126991
0.7721	Intermediate Similarity	NPC83218
0.7721	Intermediate Similarity	NPC476033
0.7718	Intermediate Similarity	NPC22137
0.7717	Intermediate Similarity	NPC30563
0.7714	Intermediate Similarity	NPC327204
0.7714	Intermediate Similarity	NPC323379
0.7708	Intermediate Similarity	NPC77493
0.7707	Intermediate Similarity	NPC102465
0.7704	Intermediate Similarity	NPC471466
0.7703	Intermediate Similarity	NPC470330
0.7698	Intermediate Similarity	NPC469519
0.7692	Intermediate Similarity	NPC145847
0.7687	Intermediate Similarity	NPC475328
0.7687	Intermediate Similarity	NPC11724
0.7682	Intermediate Similarity	NPC5115
0.7677	Intermediate Similarity	NPC150893
0.7677	Intermediate Similarity	NPC295408
0.7677	Intermediate Similarity	NPC329960
0.7676	Intermediate Similarity	NPC263829
0.7669	Intermediate Similarity	NPC280827
0.7669	Intermediate Similarity	NPC243059
0.7667	Intermediate Similarity	NPC107197
0.7664	Intermediate Similarity	NPC252114
0.7664	Intermediate Similarity	NPC471157
0.7662	Intermediate Similarity	NPC286919
0.7662	Intermediate Similarity	NPC475663
0.766	Intermediate Similarity	NPC88255
0.766	Intermediate Similarity	NPC136994
0.7656	Intermediate Similarity	NPC234376
0.7655	Intermediate Similarity	NPC475513
0.7655	Intermediate Similarity	NPC473755
0.7651	Intermediate Similarity	NPC469448
0.7651	Intermediate Similarity	NPC303429
0.7651	Intermediate Similarity	NPC120728
0.7651	Intermediate Similarity	NPC472339
0.7651	Intermediate Similarity	NPC222102
0.7647	Intermediate Similarity	NPC477467
0.7643	Intermediate Similarity	NPC478255
0.7643	Intermediate Similarity	NPC109990
0.7643	Intermediate Similarity	NPC281798
0.7639	Intermediate Similarity	NPC49597
0.7639	Intermediate Similarity	NPC324262
0.7639	Intermediate Similarity	NPC62800
0.7628	Intermediate Similarity	NPC471493
0.7622	Intermediate Similarity	NPC64230
0.7622	Intermediate Similarity	NPC71638
0.7619	Intermediate Similarity	NPC20485
0.7616	Intermediate Similarity	NPC133430
0.7616	Intermediate Similarity	NPC473966

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 NPC319995 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	674
0.2-0.3	1485
0.3-0.4	2896
0.4-0.5	2368
0.5-0.6	1162
0.6-0.7	301
0.7-0.8	17
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD2067	Discontinued
0.7436	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD969	Suspended
0.7381	Intermediate Similarity	NPD5909	Discontinued
0.7315	Intermediate Similarity	NPD6190	Approved
0.7244	Intermediate Similarity	NPD8455	Phase 2
0.7239	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD2629	Approved
0.7188	Intermediate Similarity	NPD5048	Discontinued
0.7133	Intermediate Similarity	NPD4628	Phase 3
0.7108	Intermediate Similarity	NPD7685	Pre-registration
0.7078	Intermediate Similarity	NPD5403	Approved
0.7073	Intermediate Similarity	NPD7799	Discontinued
0.7066	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4380	Phase 2
0.7048	Intermediate Similarity	NPD6797	Phase 2
0.7031	Intermediate Similarity	NPD6647	Phase 2
0.703	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5126	Approved
0.7029	Intermediate Similarity	NPD5125	Phase 3
0.7024	Intermediate Similarity	NPD8313	Approved
0.7024	Intermediate Similarity	NPD8312	Approved
0.7014	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7251	Discontinued
0.6984	Remote Similarity	NPD9495	Approved
0.6964	Remote Similarity	NPD7808	Phase 3
0.6962	Remote Similarity	NPD6801	Discontinued
0.6948	Remote Similarity	NPD5401	Approved
0.6941	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1091	Approved
0.6928	Remote Similarity	NPD7054	Approved
0.6894	Remote Similarity	NPD7075	Discontinued
0.6886	Remote Similarity	NPD7074	Phase 3
0.6886	Remote Similarity	NPD7472	Approved
0.6883	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5402	Approved
0.6867	Remote Similarity	NPD7228	Approved
0.6867	Remote Similarity	NPD3818	Discontinued
0.6846	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8513	Phase 3
0.6832	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7236	Approved
0.6815	Remote Similarity	NPD1653	Approved
0.6813	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6233	Phase 2
0.68	Remote Similarity	NPD7033	Discontinued
0.6788	Remote Similarity	NPD4198	Discontinued
0.6786	Remote Similarity	NPD5306	Approved
0.6786	Remote Similarity	NPD5305	Approved
0.6772	Remote Similarity	NPD7458	Discontinued
0.6769	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3751	Discontinued
0.6765	Remote Similarity	NPD6010	Discontinued
0.6763	Remote Similarity	NPD9545	Approved
0.6757	Remote Similarity	NPD5121	Approved
0.6757	Remote Similarity	NPD5119	Approved
0.6757	Remote Similarity	NPD5120	Approved
0.675	Remote Similarity	NPD37	Approved
0.6746	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6685	Approved
0.6736	Remote Similarity	NPD2797	Approved
0.6735	Remote Similarity	NPD6798	Discontinued
0.6735	Remote Similarity	NPD3268	Approved
0.6728	Remote Similarity	NPD4966	Approved
0.6728	Remote Similarity	NPD4965	Approved
0.6728	Remote Similarity	NPD4967	Phase 2
0.6718	Remote Similarity	NPD1237	Approved
0.6714	Remote Similarity	NPD8516	Approved
0.6714	Remote Similarity	NPD8515	Approved
0.6714	Remote Similarity	NPD8517	Approved
0.6711	Remote Similarity	NPD6355	Discontinued
0.6709	Remote Similarity	NPD7239	Suspended
0.6706	Remote Similarity	NPD8368	Discontinued
0.6692	Remote Similarity	NPD6686	Approved
0.669	Remote Similarity	NPD4806	Approved
0.669	Remote Similarity	NPD4807	Approved
0.6688	Remote Similarity	NPD2575	Approved
0.6687	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6799	Approved
0.6667	Remote Similarity	NPD2066	Phase 3
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7199	Phase 2
0.6647	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6166	Phase 2
0.6646	Remote Similarity	NPD6234	Discontinued
0.6642	Remote Similarity	NPD2182	Approved
0.6641	Remote Similarity	NPD5765	Approved
0.6627	Remote Similarity	NPD3787	Discontinued
0.6625	Remote Similarity	NPD6599	Discontinued
0.6623	Remote Similarity	NPD7097	Phase 1
0.6623	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4136	Approved
0.662	Remote Similarity	NPD4135	Approved
0.662	Remote Similarity	NPD4106	Approved
0.6619	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6912	Phase 3
0.6612	Remote Similarity	NPD8320	Phase 1
0.6612	Remote Similarity	NPD8319	Approved
0.6609	Remote Similarity	NPD8150	Discontinued
0.6608	Remote Similarity	NPD7240	Approved
0.6608	Remote Similarity	NPD6559	Discontinued
0.6601	Remote Similarity	NPD6005	Phase 3
0.6601	Remote Similarity	NPD6004	Phase 3
0.6601	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6002	Phase 3
0.6601	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5124	Phase 1
0.66	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD4620	Approved
0.6599	Remote Similarity	NPD4617	Approved
0.6599	Remote Similarity	NPD5201	Approved
0.6599	Remote Similarity	NPD5203	Approved
0.659	Remote Similarity	NPD8407	Phase 2
0.6589	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7411	Suspended
0.6581	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6535	Approved
0.6573	Remote Similarity	NPD6534	Approved
0.6564	Remote Similarity	NPD3817	Phase 2
0.6557	Remote Similarity	NPD7435	Discontinued
0.6556	Remote Similarity	NPD7699	Phase 2
0.6556	Remote Similarity	NPD7700	Phase 2
0.6552	Remote Similarity	NPD3225	Approved
0.6541	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7798	Approved
0.6534	Remote Similarity	NPD8361	Approved
0.6534	Remote Similarity	NPD8360	Approved
0.6529	Remote Similarity	NPD5844	Phase 1
0.6528	Remote Similarity	NPD1608	Approved
0.6528	Remote Similarity	NPD6637	Approved
0.6514	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD8434	Phase 2
0.651	Remote Similarity	NPD3764	Approved
0.651	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2625	Approved
0.6507	Remote Similarity	NPD2626	Approved
0.6507	Remote Similarity	NPD2160	Approved
0.6507	Remote Similarity	NPD2627	Approved
0.6507	Remote Similarity	NPD2159	Approved
0.6507	Remote Similarity	NPD2628	Approved
0.6496	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4340	Discontinued
0.649	Remote Similarity	NPD230	Phase 1
0.6486	Remote Similarity	NPD2613	Approved
0.6486	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6779	Approved
0.6484	Remote Similarity	NPD6782	Approved
0.6484	Remote Similarity	NPD6778	Approved
0.6484	Remote Similarity	NPD6780	Approved
0.6484	Remote Similarity	NPD6781	Approved
0.6484	Remote Similarity	NPD6776	Approved
0.6484	Remote Similarity	NPD6777	Approved
0.648	Remote Similarity	NPD689	Discontinued
0.6479	Remote Similarity	NPD4105	Approved
0.6479	Remote Similarity	NPD4102	Approved
0.6474	Remote Similarity	NPD8166	Discontinued
0.6474	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3750	Approved
0.6467	Remote Similarity	NPD4062	Phase 3
0.6463	Remote Similarity	NPD5647	Approved
0.646	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1282	Approved
0.6452	Remote Similarity	NPD1549	Phase 2
0.6447	Remote Similarity	NPD6653	Approved
0.6443	Remote Similarity	NPD7008	Discontinued
0.6441	Remote Similarity	NPD8435	Approved
0.6438	Remote Similarity	NPD5667	Approved
0.6424	Remote Similarity	NPD7058	Phase 2
0.6424	Remote Similarity	NPD6310	Approved
0.6424	Remote Similarity	NPD6311	Approved
0.6424	Remote Similarity	NPD7057	Phase 3
0.6424	Remote Similarity	NPD6309	Approved
0.6423	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD3663	Approved
0.6419	Remote Similarity	NPD5204	Approved
0.6419	Remote Similarity	NPD3664	Approved
0.6419	Remote Similarity	NPD3662	Phase 3
0.6419	Remote Similarity	NPD3661	Approved
0.6415	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD1238	Approved
0.641	Remote Similarity	NPD1652	Phase 2
0.6402	Remote Similarity	NPD7819	Suspended
0.6402	Remote Similarity	NPD1465	Phase 2
0.6397	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3266	Approved
0.6395	Remote Similarity	NPD3267	Approved
0.6392	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD1929	Approved
0.6391	Remote Similarity	NPD1930	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