NPASS Compound

Structure

NPC475258 OpenBabel07101719152D 42 50 0 0 1 0 0 0 0 0999 V2000 2.8135 -1.4690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9124 -2.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4398 -0.9208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7168 -2.7589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8605 -0.3986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2744 0.3833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8653 -0.5891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2656 -3.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4765 -1.2972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3041 0.2666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2011 -2.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7004 -1.4627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2937 -0.1443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5780 0.0191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1612 -3.1657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4059 -2.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2037 -0.5396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4448 -3.8304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6481 -3.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4821 -3.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8865 -2.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3026 -1.1955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4120 -3.1063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4727 -2.0921 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7370 -0.7295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5062 -1.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9437 -2.2130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4259 -2.0136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8632 -2.6200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9201 -0.6320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9248 -0.3159 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2935 -2.5896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0099 -1.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0237 -1.5810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0383 -2.5582 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5862 -0.7819 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5110 -3.5424 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9953 -0.9478 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9865 -3.4380 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.9102 -1.2930 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -3.6708 -0.4414 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 2 1 0 0 0 0 1 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 26 2 0 0 0 0 10 30 2 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 31 1 0 0 0 0 15 18 2 0 0 0 0 15 27 1 0 0 0 0 16 20 1 0 0 0 0 16 29 1 0 0 0 0 18 37 1 0 0 0 0 19 39 1 0 0 0 0 20 39 1 0 0 0 0 21 24 1 0 0 0 0 22 28 2 0 0 0 0 22 36 1 0 0 0 0 23 35 1 0 0 0 0 23 39 1 0 0 0 0 24 40 1 6 0 0 0 25 41 2 0 0 0 0 26 27 1 0 0 0 0 26 30 1 0 0 0 0 27 33 2 0 0 0 0 28 29 1 0 0 0 0 28 32 1 0 0 0 0 29 35 1 1 0 0 0 30 38 1 0 0 0 0 31 40 1 1 0 0 0 31 42 1 0 0 0 0 32 33 1 0 0 0 0 32 37 2 0 0 0 0 33 38 1 0 0 0 0 34 35 1 1 0 0 0 34 36 1 0 0 0 0 34 40 1 0 0 0 0 35 21 1 1 0 0 0 36 17 1 6 0 0 0 36 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.33
Volume:	592.043
LogP:	3.827
LogD:	3.419
LogS:	-3.807
# Rotatable Bonds:	1
TPSA:	61.46
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	6.823
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.285
MDCK Permeability:	2.1224923330009915e-05
Pgp-inhibitor:	0.451
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.541
Plasma Protein Binding (PPB):	93.64936065673828%
Volume Distribution (VD):	2.398
Pgp-substrate:	6.2162885665893555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.211
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.096
CYP2C9-substrate:	0.23
CYP2D6-inhibitor:	0.983
CYP2D6-substrate:	0.927
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	6.638
Half-life (T1/2):	0.347

ADMET: Toxicity

hERG Blockers:	0.965
Human Hepatotoxicity (H-HT):	0.993
Drug-inuced Liver Injury (DILI):	0.089
AMES Toxicity:	0.749
Rat Oral Acute Toxicity:	0.377
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.944
Carcinogencity:	0.572
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC475258

Natural Product ID:	NPC475258
*Common Name:**	12,28-Oxamanzamine E
IUPAC Name:	n.a.
Synonyms:	12,28-Oxamanzamine E
Standard InCHIKey:	USCAJZIXTMHSJM-QTICBHJOSA-N
Standard InCHI:	InChI=1S/C36H42N4O2/c41-25-12-11-24-21-35-23-39-19-8-4-2-1-3-7-17-36(34(35)40(24)31(42-36)14-13-25)22-28(29(35)16-20-39)32-33-27(15-18-37-32)26-9-5-6-10-30(26)38-33/h1,3,5-6,9-10,15,18,22,24,29,31,34,38H,2,4,7-8,11-14,16-17,19-21,23H2/b3-1-/t24-,29-,31+,34+,35-,36-/m0/s1
SMILES:	O=C1CC[C@H]2C[C@]34[C@H]5N2[C@@H](CC1)O[C@@]15CC/C=CCCCCN(C3)CC[C@H]4C(=C1)c1nccc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502167
PubChem CID:	11844765
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332848]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2004-Mar	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2002-May	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28452477]

☑ 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	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	18.0	ug.mL-1	PMID[533535]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	40.0	ug.mL-1	PMID[533535]

☑ 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 NPC475258 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	442
0.1-0.2	2175
0.2-0.3	13910
0.3-0.4	18646
0.4-0.5	3284
0.5-0.6	2214
0.6-0.7	1763
0.7-0.8	244
0.8-0.85	11
0.85-0.9	3
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC909
0.9851	High Similarity	NPC475338
0.922	High Similarity	NPC473310
0.9216	High Similarity	NPC472027
0.9118	High Similarity	NPC473757
0.8638	High Similarity	NPC471506
0.8551	High Similarity	NPC473362
0.8551	High Similarity	NPC166492
0.8514	High Similarity	NPC41679
0.844	Intermediate Similarity	NPC476491
0.8357	Intermediate Similarity	NPC250835
0.8319	Intermediate Similarity	NPC473312
0.8273	Intermediate Similarity	NPC476492
0.8253	Intermediate Similarity	NPC471891
0.8252	Intermediate Similarity	NPC265576
0.8139	Intermediate Similarity	NPC471564
0.8066	Intermediate Similarity	NPC475288
0.8065	Intermediate Similarity	NPC251936
0.8035	Intermediate Similarity	NPC81175
0.8034	Intermediate Similarity	NPC476493
0.7946	Intermediate Similarity	NPC6215
0.7834	Intermediate Similarity	NPC126066
0.7763	Intermediate Similarity	NPC476451
0.7748	Intermediate Similarity	NPC477714
0.7727	Intermediate Similarity	NPC234078
0.7727	Intermediate Similarity	NPC221100
0.7703	Intermediate Similarity	NPC477715
0.7626	Intermediate Similarity	NPC162860
0.7615	Intermediate Similarity	NPC54420
0.7606	Intermediate Similarity	NPC232130
0.7598	Intermediate Similarity	NPC191382
0.7598	Intermediate Similarity	NPC56109
0.7591	Intermediate Similarity	NPC475422
0.7545	Intermediate Similarity	NPC478158
0.7533	Intermediate Similarity	NPC155444
0.7512	Intermediate Similarity	NPC62749
0.7511	Intermediate Similarity	NPC472762
0.75	Intermediate Similarity	NPC87755
0.7489	Intermediate Similarity	NPC470730
0.7489	Intermediate Similarity	NPC477175
0.7489	Intermediate Similarity	NPC475602
0.7489	Intermediate Similarity	NPC2395
0.7488	Intermediate Similarity	NPC67288
0.7477	Intermediate Similarity	NPC98715
0.7466	Intermediate Similarity	NPC271862
0.7457	Intermediate Similarity	NPC477177
0.7457	Intermediate Similarity	NPC475969
0.7457	Intermediate Similarity	NPC475859
0.7455	Intermediate Similarity	NPC478157
0.7446	Intermediate Similarity	NPC314954
0.7444	Intermediate Similarity	NPC151976
0.7444	Intermediate Similarity	NPC87856
0.7444	Intermediate Similarity	NPC118940
0.7441	Intermediate Similarity	NPC102338
0.7441	Intermediate Similarity	NPC63199
0.7441	Intermediate Similarity	NPC111602
0.7441	Intermediate Similarity	NPC196251
0.7434	Intermediate Similarity	NPC281049
0.7431	Intermediate Similarity	NPC260900
0.743	Intermediate Similarity	NPC195239
0.743	Intermediate Similarity	NPC157828
0.7425	Intermediate Similarity	NPC165743
0.7419	Intermediate Similarity	NPC214428
0.7411	Intermediate Similarity	NPC267965
0.7409	Intermediate Similarity	NPC277350
0.7409	Intermediate Similarity	NPC238457
0.7407	Intermediate Similarity	NPC171317
0.7406	Intermediate Similarity	NPC472112
0.7395	Intermediate Similarity	NPC11445
0.7376	Intermediate Similarity	NPC46225
0.7376	Intermediate Similarity	NPC477065
0.7376	Intermediate Similarity	NPC225821
0.7366	Intermediate Similarity	NPC318299
0.7364	Intermediate Similarity	NPC327592
0.7345	Intermediate Similarity	NPC132211
0.7342	Intermediate Similarity	NPC127677
0.7342	Intermediate Similarity	NPC258062
0.7339	Intermediate Similarity	NPC252338
0.7336	Intermediate Similarity	NPC472113
0.7333	Intermediate Similarity	NPC317752
0.7333	Intermediate Similarity	NPC472119
0.7333	Intermediate Similarity	NPC284678
0.733	Intermediate Similarity	NPC317373
0.7316	Intermediate Similarity	NPC235885
0.7315	Intermediate Similarity	NPC245916
0.7309	Intermediate Similarity	NPC223791
0.7309	Intermediate Similarity	NPC107077
0.7306	Intermediate Similarity	NPC300183
0.7299	Intermediate Similarity	NPC15102
0.7296	Intermediate Similarity	NPC33949
0.7294	Intermediate Similarity	NPC74413
0.7277	Intermediate Similarity	NPC213629
0.7277	Intermediate Similarity	NPC123839
0.7277	Intermediate Similarity	NPC321708
0.7273	Intermediate Similarity	NPC476874
0.7273	Intermediate Similarity	NPC193761
0.7269	Intermediate Similarity	NPC36405
0.7269	Intermediate Similarity	NPC203614
0.7269	Intermediate Similarity	NPC204491
0.7265	Intermediate Similarity	NPC470729
0.7265	Intermediate Similarity	NPC477176
0.7261	Intermediate Similarity	NPC474896
0.726	Intermediate Similarity	NPC254240
0.726	Intermediate Similarity	NPC312870
0.726	Intermediate Similarity	NPC128265
0.726	Intermediate Similarity	NPC199851
0.726	Intermediate Similarity	NPC294909
0.7257	Intermediate Similarity	NPC54744
0.7238	Intermediate Similarity	NPC477861
0.7234	Intermediate Similarity	NPC474877
0.723	Intermediate Similarity	NPC17059
0.7229	Intermediate Similarity	NPC31097
0.7227	Intermediate Similarity	NPC475506
0.7215	Intermediate Similarity	NPC293917
0.7215	Intermediate Similarity	NPC241024
0.7215	Intermediate Similarity	NPC100321
0.7215	Intermediate Similarity	NPC325976
0.7212	Intermediate Similarity	NPC75634
0.7212	Intermediate Similarity	NPC280852
0.7209	Intermediate Similarity	NPC117244
0.7209	Intermediate Similarity	NPC473763
0.7203	Intermediate Similarity	NPC469554
0.7202	Intermediate Similarity	NPC227582
0.7198	Intermediate Similarity	NPC229893
0.7196	Intermediate Similarity	NPC175474
0.7195	Intermediate Similarity	NPC155143
0.7193	Intermediate Similarity	NPC470731
0.7189	Intermediate Similarity	NPC220151
0.7189	Intermediate Similarity	NPC19692
0.7188	Intermediate Similarity	NPC266249
0.7183	Intermediate Similarity	NPC94752
0.7182	Intermediate Similarity	NPC195461
0.7182	Intermediate Similarity	NPC249150
0.7182	Intermediate Similarity	NPC49196
0.7182	Intermediate Similarity	NPC81654
0.7182	Intermediate Similarity	NPC313985
0.7182	Intermediate Similarity	NPC79129
0.7179	Intermediate Similarity	NPC57690
0.7173	Intermediate Similarity	NPC63279
0.7173	Intermediate Similarity	NPC70155
0.7169	Intermediate Similarity	NPC131887
0.7169	Intermediate Similarity	NPC50503
0.7169	Intermediate Similarity	NPC473640
0.7169	Intermediate Similarity	NPC52557
0.7162	Intermediate Similarity	NPC476041
0.7162	Intermediate Similarity	NPC304926
0.7157	Intermediate Similarity	NPC21174
0.7157	Intermediate Similarity	NPC271797
0.7149	Intermediate Similarity	NPC474412
0.7143	Intermediate Similarity	NPC326422
0.7143	Intermediate Similarity	NPC272174
0.7143	Intermediate Similarity	NPC297642
0.7137	Intermediate Similarity	NPC53534
0.7136	Intermediate Similarity	NPC308931
0.7136	Intermediate Similarity	NPC99939
0.7131	Intermediate Similarity	NPC101543
0.713	Intermediate Similarity	NPC472097
0.7124	Intermediate Similarity	NPC266192
0.7123	Intermediate Similarity	NPC143533
0.7117	Intermediate Similarity	NPC162730
0.7117	Intermediate Similarity	NPC328596
0.7117	Intermediate Similarity	NPC476073
0.7117	Intermediate Similarity	NPC328318
0.7114	Intermediate Similarity	NPC14812
0.7111	Intermediate Similarity	NPC314957
0.711	Intermediate Similarity	NPC133366
0.7109	Intermediate Similarity	NPC469896
0.7097	Intermediate Similarity	NPC55493
0.7095	Intermediate Similarity	NPC14113
0.7095	Intermediate Similarity	NPC145885
0.7095	Intermediate Similarity	NPC84827
0.7095	Intermediate Similarity	NPC59269
0.7094	Intermediate Similarity	NPC141428
0.7093	Intermediate Similarity	NPC320968
0.7089	Intermediate Similarity	NPC472294
0.7089	Intermediate Similarity	NPC258480
0.7083	Intermediate Similarity	NPC329858
0.7064	Intermediate Similarity	NPC24370
0.7064	Intermediate Similarity	NPC319232
0.7064	Intermediate Similarity	NPC267926
0.7062	Intermediate Similarity	NPC141377
0.7062	Intermediate Similarity	NPC213468
0.7061	Intermediate Similarity	NPC107836
0.7056	Intermediate Similarity	NPC79062
0.7056	Intermediate Similarity	NPC472107
0.7054	Intermediate Similarity	NPC473376
0.7054	Intermediate Similarity	NPC101350
0.7053	Intermediate Similarity	NPC317430
0.7051	Intermediate Similarity	NPC147446
0.7051	Intermediate Similarity	NPC64216
0.7049	Intermediate Similarity	NPC81939
0.7046	Intermediate Similarity	NPC326363
0.7046	Intermediate Similarity	NPC69843
0.7042	Intermediate Similarity	NPC139291
0.7042	Intermediate Similarity	NPC472108
0.7042	Intermediate Similarity	NPC48938
0.704	Intermediate Similarity	NPC474116
0.7039	Intermediate Similarity	NPC60621
0.7036	Intermediate Similarity	NPC152620
0.7031	Intermediate Similarity	NPC229348

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 NPC475258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	572
0.2-0.3	832
0.3-0.4	2176
0.4-0.5	2565
0.5-0.6	2041
0.6-0.7	685
0.7-0.8	43
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7876	Intermediate Similarity	NPD7824	Approved
0.7851	Intermediate Similarity	NPD7951	Approved
0.7851	Intermediate Similarity	NPD7791	Approved
0.7851	Intermediate Similarity	NPD7950	Approved
0.7851	Intermediate Similarity	NPD7952	Approved
0.7851	Intermediate Similarity	NPD7953	Approved
0.7851	Intermediate Similarity	NPD7789	Approved
0.7851	Intermediate Similarity	NPD7790	Approved
0.7788	Intermediate Similarity	NPD7731	Approved
0.7788	Intermediate Similarity	NPD7730	Approved
0.7699	Intermediate Similarity	NPD7271	Approved
0.7598	Intermediate Similarity	NPD7781	Approved
0.7598	Intermediate Similarity	NPD7780	Approved
0.7477	Intermediate Similarity	NPD7470	Discontinued
0.7444	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD5426	Phase 3
0.7421	Intermediate Similarity	NPD7665	Phase 2
0.7421	Intermediate Similarity	NPD7666	Phase 3
0.7345	Intermediate Similarity	NPD3393	Approved
0.7345	Intermediate Similarity	NPD3394	Approved
0.7345	Intermediate Similarity	NPD3389	Approved
0.7342	Intermediate Similarity	NPD2510	Approved
0.7342	Intermediate Similarity	NPD2509	Approved
0.7318	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4500	Approved
0.726	Intermediate Similarity	NPD4501	Approved
0.7252	Intermediate Similarity	NPD7001	Phase 3
0.722	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4601	Approved
0.7182	Intermediate Similarity	NPD4600	Approved
0.7175	Intermediate Similarity	NPD7957	Phase 1
0.7175	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6999	Discontinued
0.7136	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5003	Discontinued
0.711	Intermediate Similarity	NPD7618	Phase 3
0.711	Intermediate Similarity	NPD7619	Phase 3
0.7105	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD8289	Discontinued
0.7061	Intermediate Similarity	NPD8093	Discontinued
0.7061	Intermediate Similarity	NPD7454	Approved
0.7061	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7455	Approved
0.7054	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6595	Phase 3
0.7026	Intermediate Similarity	NPD3402	Phase 1
0.7025	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6178	Phase 3
0.7009	Intermediate Similarity	NPD2096	Phase 2
0.7009	Intermediate Similarity	NPD2091	Phase 2
0.7005	Intermediate Similarity	NPD4499	Approved
0.7	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD8358	Approved
0.6991	Remote Similarity	NPD8322	Phase 2
0.6987	Remote Similarity	NPD3330	Phase 1
0.6983	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7717	Approved
0.6979	Remote Similarity	NPD7716	Approved
0.6978	Remote Similarity	NPD56	Approved
0.6978	Remote Similarity	NPD8282	Approved
0.6978	Remote Similarity	NPD8283	Approved
0.6972	Remote Similarity	NPD5913	Phase 3
0.6972	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2095	Phase 2
0.6963	Remote Similarity	NPD2094	Phase 2
0.6963	Remote Similarity	NPD2092	Phase 2
0.6962	Remote Similarity	NPD6164	Phase 2
0.6962	Remote Similarity	NPD6978	Phase 2
0.6962	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6165	Phase 2
0.696	Remote Similarity	NPD8247	Approved
0.696	Remote Similarity	NPD8246	Approved
0.6955	Remote Similarity	NPD4602	Approved
0.6955	Remote Similarity	NPD7944	Discontinued
0.6951	Remote Similarity	NPD6479	Discontinued
0.6948	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5482	Discontinued
0.6934	Remote Similarity	NPD2144	Approved
0.6933	Remote Similarity	NPD4886	Phase 2
0.692	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD482	Approved
0.6919	Remote Similarity	NPD5065	Approved
0.6916	Remote Similarity	NPD3038	Discontinued
0.6912	Remote Similarity	NPD8431	Approved
0.6912	Remote Similarity	NPD3961	Discontinued
0.6901	Remote Similarity	NPD5891	Approved
0.6898	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6664	Approved
0.6883	Remote Similarity	NPD8094	Discontinued
0.688	Remote Similarity	NPD7404	Approved
0.687	Remote Similarity	NPD5475	Discontinued
0.6869	Remote Similarity	NPD5473	Discontinued
0.6867	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5559	Phase 2
0.6858	Remote Similarity	NPD8072	Approved
0.6849	Remote Similarity	NPD2564	Approved
0.6849	Remote Similarity	NPD6281	Approved
0.6849	Remote Similarity	NPD2565	Phase 2
0.6849	Remote Similarity	NPD7711	Discontinued
0.6842	Remote Similarity	NPD7921	Approved
0.6835	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8272	Phase 2
0.6828	Remote Similarity	NPD5901	Discontinued
0.6826	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7415	Suspended
0.6815	Remote Similarity	NPD8100	Phase 3
0.6814	Remote Similarity	NPD8073	Approved
0.6814	Remote Similarity	NPD2837	Discontinued
0.6812	Remote Similarity	NPD8423	Phase 2
0.6812	Remote Similarity	NPD8399	Phase 1
0.6812	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD5104	Approved
0.6804	Remote Similarity	NPD7233	Approved
0.6804	Remote Similarity	NPD7234	Approved
0.6795	Remote Similarity	NPD8325	Phase 3
0.6795	Remote Similarity	NPD8326	Phase 3
0.6795	Remote Similarity	NPD8364	Approved
0.6795	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD8363	Approved
0.6793	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8426	Approved
0.6792	Remote Similarity	NPD8425	Approved
0.6781	Remote Similarity	NPD7970	Approved
0.6781	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6242	Discontinued
0.6777	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5017	Discontinued
0.6769	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8428	Approved
0.6768	Remote Similarity	NPD8429	Approved
0.6768	Remote Similarity	NPD8427	Approved
0.6757	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD3947	Discontinued
0.6753	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3323	Discontinued
0.6744	Remote Similarity	NPD4076	Approved
0.6744	Remote Similarity	NPD4079	Approved
0.6743	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD2880	Discontinued
0.6736	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7688	Phase 1
0.6735	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD8101	Phase 3
0.673	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD4075	Phase 2
0.6727	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD750	Phase 2
0.6714	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7603	Discontinued
0.6708	Remote Similarity	NPD8119	Discontinued
0.6705	Remote Similarity	NPD8467	Approved
0.6705	Remote Similarity	NPD8466	Approved
0.6705	Remote Similarity	NPD8465	Approved
0.6698	Remote Similarity	NPD3505	Approved
0.6698	Remote Similarity	NPD4181	Approved
0.6698	Remote Similarity	NPD3506	Approved
0.6697	Remote Similarity	NPD8063	Discontinued
0.6697	Remote Similarity	NPD7564	Discontinued
0.6696	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD2411	Approved
0.6681	Remote Similarity	NPD4051	Discontinued
0.6681	Remote Similarity	NPD8114	Approved
0.6681	Remote Similarity	NPD8115	Approved
0.668	Remote Similarity	NPD6992	Phase 2
0.6667	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6268	Phase 1
0.6667	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7948	Phase 1
0.6654	Remote Similarity	NPD6531	Approved
0.6654	Remote Similarity	NPD6530	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