NPASS Compound

Structure

CID77310 OpenBabel06191715412D 43 48 0 0 1 0 0 0 0 0999 V2000 1.0286 3.1688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5178 3.5544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7926 2.3037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0544 -1.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2027 -1.6674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0541 -0.1908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0893 1.2832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0896 0.2996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4977 1.2842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6452 1.7761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3845 2.0657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6460 -1.1760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8511 -1.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8289 1.3726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0065 3.0663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9401 2.7588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4066 2.1682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4980 0.3006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3508 -1.1755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6457 -0.1918 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9404 1.7756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7932 0.3001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2022 0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4985 -1.6679 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9622 2.8613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8514 -0.4919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3505 -0.1913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7030 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7033 0.9827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8519 1.4746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5842 3.8619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9832 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7929 1.2837 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0006 -1.9664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2019 1.3011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4988 -2.6679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5544 -0.4923 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5549 1.4741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8522 2.4578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1840 4.7600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8511 1.4751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5620 3.7594 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 15 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 19 1 0 0 0 0 6 23 2 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 10 33 1 0 0 0 0 11 17 1 0 0 0 0 11 25 1 0 0 0 0 12 24 1 0 0 0 0 13 34 1 0 0 0 0 14 17 1 0 0 0 0 14 41 1 0 0 0 0 15 17 2 0 0 0 0 15 31 1 0 0 0 0 16 2 1 1 0 0 0 16 21 1 0 0 0 0 18 9 1 6 0 0 0 18 20 1 0 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 19 27 2 0 0 0 0 20 12 1 1 0 0 0 20 22 1 0 0 0 0 21 33 1 6 0 0 0 22 33 1 6 0 0 0 23 27 1 0 0 0 0 23 35 1 0 0 0 0 24 36 1 1 0 0 0 25 16 1 1 0 0 0 25 42 1 0 0 0 0 26 13 1 6 0 0 0 26 28 1 0 0 0 0 26 43 1 0 0 0 0 28 29 1 0 0 0 0 28 37 1 1 0 0 0 29 30 1 0 0 0 0 29 38 1 6 0 0 0 30 32 1 0 0 0 0 30 39 1 1 0 0 0 31 40 2 0 0 0 0 31 42 1 0 0 0 0 32 41 1 6 0 0 0 32 43 1 0 0 0 0 33 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.31
Volume:	602.705
LogP:	2.514
LogD:	2.928
LogS:	-4.152
# Rotatable Bonds:	6
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	5.343
Fsp3:	0.727
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.924
MDCK Permeability:	1.4690111129311845e-05
Pgp-inhibitor:	0.306
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.94
20% Bioavailability (F20%):	0.104
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	92.66681671142578%
Volume Distribution (VD):	0.619
Pgp-substrate:	5.734673023223877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.624
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.101
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.247
CYP3A4-substrate:	0.432

ADMET: Excretion

Clearance (CL):	4.122
Half-life (T1/2):	0.702

ADMET: Toxicity

hERG Blockers:	0.64
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.3
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.284
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.82
Carcinogencity:	0.558
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC77310

Natural Product ID:	NPC77310
*Common Name:**	Withalongolidesaponin
IUPAC Name:	(2R)-2-[(1S)-1-[(6S,8S,9S,13S,14S,17R)-1,6-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-methyl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one
Synonyms:	Withalongolidesaponin
Standard InCHIKey:	QYYMGJGFQVRKJA-RMHZGSCISA-N
Standard InCHI:	InChI=1S/C33H46O10/c1-15-17(14-41-32-30(39)29(38)28(37)26(13-34)43-32)11-25(42-31(15)40)16(2)21-7-8-22-20-12-24(36)19-5-4-6-23(35)27(19)18(20)9-10-33(21,22)3/h4-6,16,18,20-22,24-26,28-30,32,34-39H,7-14H2,1-3H3/t16-,18-,20+,21+,22-,24-,25+,26+,28+,29-,30+,32+,33+/m0/s1
SMILES:	CC1=C(C[C@H]([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@@H](c5cccc(c5[C@H]4CC[C@]23C)O)O)OC1=O)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1934463
PubChem CID:	56926207
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[531426]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10000.0	nM	PMID[531426]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[531426]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[531426]

☑ 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 NPC77310 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	317
0.1-0.2	1186
0.2-0.3	2663
0.3-0.4	4804
0.4-0.5	8783
0.5-0.6	11718
0.6-0.7	10375
0.7-0.8	2680
0.8-0.85	156
0.85-0.9	14
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.898	High Similarity	NPC96447
0.8912	High Similarity	NPC204644
0.8859	High Similarity	NPC320734
0.8846	High Similarity	NPC269668
0.8742	High Similarity	NPC95990
0.8707	High Similarity	NPC164743
0.8634	High Similarity	NPC286809
0.8581	High Similarity	NPC470617
0.8581	High Similarity	NPC470616
0.8514	High Similarity	NPC116742
0.8514	High Similarity	NPC139243
0.8477	Intermediate Similarity	NPC26045
0.8477	Intermediate Similarity	NPC296659
0.8477	Intermediate Similarity	NPC251062
0.8477	Intermediate Similarity	NPC202391
0.8477	Intermediate Similarity	NPC184464
0.8462	Intermediate Similarity	NPC471874
0.8462	Intermediate Similarity	NPC469699
0.8462	Intermediate Similarity	NPC257847
0.8418	Intermediate Similarity	NPC10945
0.8411	Intermediate Similarity	NPC252133
0.8411	Intermediate Similarity	NPC235557
0.8411	Intermediate Similarity	NPC310621
0.8367	Intermediate Similarity	NPC11266
0.8344	Intermediate Similarity	NPC35212
0.8333	Intermediate Similarity	NPC471861
0.8323	Intermediate Similarity	NPC475613
0.8312	Intermediate Similarity	NPC472938
0.8312	Intermediate Similarity	NPC472937
0.8312	Intermediate Similarity	NPC470330
0.8312	Intermediate Similarity	NPC472936
0.8302	Intermediate Similarity	NPC148323
0.8302	Intermediate Similarity	NPC283480
0.8289	Intermediate Similarity	NPC186296
0.8278	Intermediate Similarity	NPC154262
0.8278	Intermediate Similarity	NPC473612
0.8278	Intermediate Similarity	NPC7518
0.8278	Intermediate Similarity	NPC159387
0.8278	Intermediate Similarity	NPC137501
0.8269	Intermediate Similarity	NPC472939
0.8253	Intermediate Similarity	NPC13989
0.8242	Intermediate Similarity	NPC471870
0.8239	Intermediate Similarity	NPC82190
0.8239	Intermediate Similarity	NPC192219
0.8239	Intermediate Similarity	NPC174599
0.8221	Intermediate Similarity	NPC25889
0.8205	Intermediate Similarity	NPC96599
0.8204	Intermediate Similarity	NPC471871
0.8199	Intermediate Similarity	NPC478269
0.8199	Intermediate Similarity	NPC53139
0.8194	Intermediate Similarity	NPC97240
0.8188	Intermediate Similarity	NPC263829
0.8182	Intermediate Similarity	NPC208818
0.8176	Intermediate Similarity	NPC205172
0.8176	Intermediate Similarity	NPC209393
0.817	Intermediate Similarity	NPC247032
0.817	Intermediate Similarity	NPC476397
0.817	Intermediate Similarity	NPC112
0.817	Intermediate Similarity	NPC298257
0.817	Intermediate Similarity	NPC175214
0.817	Intermediate Similarity	NPC476378
0.817	Intermediate Similarity	NPC476384
0.817	Intermediate Similarity	NPC269141
0.817	Intermediate Similarity	NPC264632
0.817	Intermediate Similarity	NPC76406
0.817	Intermediate Similarity	NPC96795
0.817	Intermediate Similarity	NPC205864
0.817	Intermediate Similarity	NPC476380
0.817	Intermediate Similarity	NPC476375
0.817	Intermediate Similarity	NPC476381
0.817	Intermediate Similarity	NPC119537
0.817	Intermediate Similarity	NPC293154
0.8165	Intermediate Similarity	NPC478268
0.8163	Intermediate Similarity	NPC473047
0.8163	Intermediate Similarity	NPC46137
0.8163	Intermediate Similarity	NPC254819
0.8163	Intermediate Similarity	NPC235294
0.816	Intermediate Similarity	NPC145847
0.816	Intermediate Similarity	NPC187934
0.816	Intermediate Similarity	NPC97637
0.8158	Intermediate Similarity	NPC475513
0.8158	Intermediate Similarity	NPC476377
0.8158	Intermediate Similarity	NPC473755
0.8158	Intermediate Similarity	NPC47471
0.8153	Intermediate Similarity	NPC470618
0.8153	Intermediate Similarity	NPC35160
0.8153	Intermediate Similarity	NPC267469
0.8153	Intermediate Similarity	NPC247219
0.8153	Intermediate Similarity	NPC117346
0.8153	Intermediate Similarity	NPC145527
0.8153	Intermediate Similarity	NPC69367
0.8153	Intermediate Similarity	NPC208785
0.8153	Intermediate Similarity	NPC116292
0.8153	Intermediate Similarity	NPC87630
0.8153	Intermediate Similarity	NPC179128
0.8153	Intermediate Similarity	NPC162569
0.8153	Intermediate Similarity	NPC470619
0.8153	Intermediate Similarity	NPC240592
0.8148	Intermediate Similarity	NPC208676
0.8148	Intermediate Similarity	NPC130489
0.8146	Intermediate Similarity	NPC64141
0.8146	Intermediate Similarity	NPC49597
0.8146	Intermediate Similarity	NPC197316
0.8146	Intermediate Similarity	NPC68092
0.8146	Intermediate Similarity	NPC248287
0.8146	Intermediate Similarity	NPC234548
0.8146	Intermediate Similarity	NPC89105
0.8146	Intermediate Similarity	NPC472350
0.8146	Intermediate Similarity	NPC476383
0.8146	Intermediate Similarity	NPC81515
0.8144	Intermediate Similarity	NPC469774
0.8144	Intermediate Similarity	NPC32723
0.8144	Intermediate Similarity	NPC295941
0.8144	Intermediate Similarity	NPC469777
0.8144	Intermediate Similarity	NPC469776
0.8144	Intermediate Similarity	NPC469773
0.8144	Intermediate Similarity	NPC469775
0.8144	Intermediate Similarity	NPC100925
0.8144	Intermediate Similarity	NPC477617
0.8144	Intermediate Similarity	NPC469778
0.8144	Intermediate Similarity	NPC135334
0.8144	Intermediate Similarity	NPC469772
0.8137	Intermediate Similarity	NPC208651
0.8137	Intermediate Similarity	NPC206641
0.8137	Intermediate Similarity	NPC471878
0.8133	Intermediate Similarity	NPC154485
0.8133	Intermediate Similarity	NPC471872
0.8129	Intermediate Similarity	NPC229505
0.8129	Intermediate Similarity	NPC8102
0.8129	Intermediate Similarity	NPC66894
0.8125	Intermediate Similarity	NPC474501
0.8125	Intermediate Similarity	NPC476784
0.8125	Intermediate Similarity	NPC475484
0.8121	Intermediate Similarity	NPC469419
0.8121	Intermediate Similarity	NPC469458
0.8121	Intermediate Similarity	NPC88176
0.8121	Intermediate Similarity	NPC469396
0.8121	Intermediate Similarity	NPC149002
0.8117	Intermediate Similarity	NPC300894
0.8117	Intermediate Similarity	NPC477207
0.8117	Intermediate Similarity	NPC141455
0.8117	Intermediate Similarity	NPC196063
0.8117	Intermediate Similarity	NPC64195
0.8117	Intermediate Similarity	NPC296954
0.8113	Intermediate Similarity	NPC475227
0.8113	Intermediate Similarity	NPC106669
0.8113	Intermediate Similarity	NPC200645
0.811	Intermediate Similarity	NPC327694
0.811	Intermediate Similarity	NPC109990
0.8108	Intermediate Similarity	NPC321086
0.8105	Intermediate Similarity	NPC265648
0.8105	Intermediate Similarity	NPC222433
0.8101	Intermediate Similarity	NPC472658
0.8101	Intermediate Similarity	NPC472657
0.8098	Intermediate Similarity	NPC478267
0.8095	Intermediate Similarity	NPC472793
0.8095	Intermediate Similarity	NPC473467
0.8095	Intermediate Similarity	NPC475197
0.8092	Intermediate Similarity	NPC475530
0.8092	Intermediate Similarity	NPC473591
0.8092	Intermediate Similarity	NPC271494
0.8092	Intermediate Similarity	NPC155192
0.8092	Intermediate Similarity	NPC473799
0.8089	Intermediate Similarity	NPC477206
0.8089	Intermediate Similarity	NPC279442
0.8079	Intermediate Similarity	NPC260425
0.8077	Intermediate Similarity	NPC474564
0.8065	Intermediate Similarity	NPC272619
0.8065	Intermediate Similarity	NPC286245
0.8065	Intermediate Similarity	NPC138915
0.8061	Intermediate Similarity	NPC318472
0.8054	Intermediate Similarity	NPC28637
0.8052	Intermediate Similarity	NPC105005
0.805	Intermediate Similarity	NPC476452
0.8049	Intermediate Similarity	NPC471850
0.8049	Intermediate Similarity	NPC326278
0.8049	Intermediate Similarity	NPC471873
0.8041	Intermediate Similarity	NPC225384
0.8041	Intermediate Similarity	NPC138777
0.8041	Intermediate Similarity	NPC246869
0.8041	Intermediate Similarity	NPC478255
0.8039	Intermediate Similarity	NPC3218
0.8039	Intermediate Similarity	NPC27518
0.8039	Intermediate Similarity	NPC476385
0.8039	Intermediate Similarity	NPC134405
0.8039	Intermediate Similarity	NPC46644
0.8039	Intermediate Similarity	NPC304110
0.8038	Intermediate Similarity	NPC183380
0.8038	Intermediate Similarity	NPC12006
0.8038	Intermediate Similarity	NPC35097
0.8026	Intermediate Similarity	NPC182249
0.8026	Intermediate Similarity	NPC171134
0.8026	Intermediate Similarity	NPC328273
0.8026	Intermediate Similarity	NPC324262
0.8026	Intermediate Similarity	NPC31745
0.8026	Intermediate Similarity	NPC62800
0.8026	Intermediate Similarity	NPC220936
0.8026	Intermediate Similarity	NPC321638
0.8026	Intermediate Similarity	NPC321184
0.8026	Intermediate Similarity	NPC205195

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 NPC77310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	735
0.2-0.3	1564
0.3-0.4	2780
0.4-0.5	2173
0.5-0.6	1230
0.6-0.7	355
0.7-0.8	50
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8146	Intermediate Similarity	NPD7266	Discontinued
0.7857	Intermediate Similarity	NPD7228	Approved
0.7791	Intermediate Similarity	NPD8312	Approved
0.7791	Intermediate Similarity	NPD8313	Approved
0.777	Intermediate Similarity	NPD5736	Approved
0.7677	Intermediate Similarity	NPD5763	Approved
0.7677	Intermediate Similarity	NPD5762	Approved
0.7665	Intermediate Similarity	NPD8127	Discontinued
0.7643	Intermediate Similarity	NPD8166	Discontinued
0.7635	Intermediate Similarity	NPD3094	Phase 2
0.7622	Intermediate Similarity	NPD8455	Phase 2
0.7584	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6674	Discontinued
0.7572	Intermediate Similarity	NPD7685	Pre-registration
0.7566	Intermediate Similarity	NPD6663	Approved
0.7561	Intermediate Similarity	NPD37	Approved
0.7545	Intermediate Similarity	NPD6234	Discontinued
0.753	Intermediate Similarity	NPD4967	Phase 2
0.753	Intermediate Similarity	NPD4966	Approved
0.753	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3092	Approved
0.7471	Intermediate Similarity	NPD7240	Approved
0.7456	Intermediate Similarity	NPD7199	Phase 2
0.7403	Intermediate Similarity	NPD4140	Approved
0.7346	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7799	Discontinued
0.7329	Intermediate Similarity	NPD3091	Approved
0.7317	Intermediate Similarity	NPD1653	Approved
0.7299	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7261	Intermediate Similarity	NPD7097	Phase 1
0.7244	Intermediate Similarity	NPD5735	Approved
0.7234	Intermediate Similarity	NPD8320	Phase 1
0.7234	Intermediate Similarity	NPD8319	Approved
0.723	Intermediate Similarity	NPD5126	Approved
0.723	Intermediate Similarity	NPD5125	Phase 3
0.7211	Intermediate Similarity	NPD7741	Discontinued
0.72	Intermediate Similarity	NPD7054	Approved
0.7195	Intermediate Similarity	NPD6273	Approved
0.7182	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4060	Phase 1
0.7179	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3620	Phase 2
0.7176	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6559	Discontinued
0.7159	Intermediate Similarity	NPD7074	Phase 3
0.7159	Intermediate Similarity	NPD7472	Approved
0.7152	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7808	Phase 3
0.7114	Intermediate Similarity	NPD3019	Approved
0.7114	Intermediate Similarity	NPD3095	Discontinued
0.7099	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7699	Phase 2
0.7097	Intermediate Similarity	NPD7700	Phase 2
0.709	Intermediate Similarity	NPD7435	Discontinued
0.709	Intermediate Similarity	NPD7680	Approved
0.7079	Intermediate Similarity	NPD7251	Discontinued
0.7078	Intermediate Similarity	NPD2861	Phase 2
0.7059	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6190	Approved
0.7047	Intermediate Similarity	NPD7503	Approved
0.703	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6535	Approved
0.7027	Intermediate Similarity	NPD6534	Approved
0.7024	Intermediate Similarity	NPD7028	Phase 2
0.7022	Intermediate Similarity	NPD6797	Phase 2
0.702	Intermediate Similarity	NPD1091	Approved
0.7012	Intermediate Similarity	NPD7236	Approved
0.7006	Intermediate Similarity	NPD5844	Phase 1
0.7006	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8032	Phase 2
0.7	Intermediate Similarity	NPD2932	Approved
0.6994	Remote Similarity	NPD4628	Phase 3
0.6987	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6653	Approved
0.697	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7874	Approved
0.6959	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3818	Discontinued
0.6947	Remote Similarity	NPD6823	Phase 2
0.6944	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD8033	Approved
0.6933	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6782	Approved
0.6931	Remote Similarity	NPD6780	Approved
0.6931	Remote Similarity	NPD6778	Approved
0.6931	Remote Similarity	NPD6781	Approved
0.6931	Remote Similarity	NPD6777	Approved
0.6931	Remote Similarity	NPD6779	Approved
0.6931	Remote Similarity	NPD6776	Approved
0.6928	Remote Similarity	NPD5327	Phase 3
0.6923	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4380	Phase 2
0.6923	Remote Similarity	NPD7783	Phase 2
0.6919	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6355	Discontinued
0.6918	Remote Similarity	NPD5124	Phase 1
0.6918	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7698	Approved
0.6911	Remote Similarity	NPD7696	Phase 3
0.6911	Remote Similarity	NPD7697	Approved
0.6907	Remote Similarity	NPD8151	Discontinued
0.6905	Remote Similarity	NPD7239	Suspended
0.6901	Remote Similarity	NPD7819	Suspended
0.6893	Remote Similarity	NPD7473	Discontinued
0.689	Remote Similarity	NPD7003	Approved
0.689	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4059	Approved
0.6887	Remote Similarity	NPD4626	Approved
0.6882	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6212	Phase 3
0.6882	Remote Similarity	NPD6213	Phase 3
0.6879	Remote Similarity	NPD7095	Approved
0.6875	Remote Similarity	NPD7871	Phase 2
0.6875	Remote Similarity	NPD6353	Approved
0.6875	Remote Similarity	NPD7870	Phase 2
0.6867	Remote Similarity	NPD8294	Approved
0.6867	Remote Similarity	NPD8377	Approved
0.6856	Remote Similarity	NPD7701	Phase 2
0.6854	Remote Similarity	NPD3751	Discontinued
0.6837	Remote Similarity	NPD7801	Approved
0.6835	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3764	Approved
0.6826	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8296	Approved
0.6821	Remote Similarity	NPD8380	Approved
0.6821	Remote Similarity	NPD8379	Approved
0.6821	Remote Similarity	NPD8335	Approved
0.6821	Remote Similarity	NPD5691	Approved
0.6821	Remote Similarity	NPD8378	Approved
0.6818	Remote Similarity	NPD6232	Discontinued
0.6818	Remote Similarity	NPD3787	Discontinued
0.6815	Remote Similarity	NPD4908	Phase 1
0.681	Remote Similarity	NPD6002	Phase 3
0.681	Remote Similarity	NPD6005	Phase 3
0.681	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6004	Phase 3
0.6795	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4624	Approved
0.6793	Remote Similarity	NPD8434	Phase 2
0.679	Remote Similarity	NPD7033	Discontinued
0.6782	Remote Similarity	NPD7075	Discontinued
0.6779	Remote Similarity	NPD4198	Discontinued
0.6774	Remote Similarity	NPD8651	Approved
0.6763	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6959	Discontinued
0.675	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1613	Approved
0.6748	Remote Similarity	NPD6100	Approved
0.6748	Remote Similarity	NPD5405	Approved
0.6748	Remote Similarity	NPD5408	Approved
0.6748	Remote Similarity	NPD5406	Approved
0.6748	Remote Similarity	NPD6099	Approved
0.6748	Remote Similarity	NPD5404	Approved
0.6747	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6166	Phase 2
0.6742	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7930	Approved
0.6733	Remote Similarity	NPD7327	Approved
0.6733	Remote Similarity	NPD7328	Approved
0.6732	Remote Similarity	NPD3023	Approved
0.6732	Remote Similarity	NPD3026	Approved
0.673	Remote Similarity	NPD7985	Registered
0.6727	Remote Similarity	NPD1652	Phase 2
0.6726	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3024	Approved
0.6711	Remote Similarity	NPD3025	Approved
0.6689	Remote Similarity	NPD7516	Approved
0.6688	Remote Similarity	NPD3705	Approved
0.6687	Remote Similarity	NPD3750	Approved
0.6687	Remote Similarity	NPD7743	Approved
0.6687	Remote Similarity	NPD7742	Approved
0.6687	Remote Similarity	NPD4110	Phase 3
0.6687	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4625	Phase 3
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD6696	Suspended
0.6667	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7497	Discontinued
0.6646	Remote Similarity	NPD2438	Suspended
0.6629	Remote Similarity	NPD7768	Phase 2
0.6627	Remote Similarity	NPD2534	Approved
0.6627	Remote Similarity	NPD2533	Approved
0.6627	Remote Similarity	NPD2532	Approved
0.6625	Remote Similarity	NPD6798	Discontinued
0.6624	Remote Similarity	NPD2797	Approved
0.6623	Remote Similarity	NPD3496	Discontinued
0.6618	Remote Similarity	NPD8155	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