NPASS Compound

Structure

CID293347 OpenBabel06191716102D 49 54 0 0 1 0 0 0 0 0999 V2000 -5.5887 -3.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6324 -3.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9157 1.0960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8124 5.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5841 -0.5851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2247 -2.3718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2797 -3.0053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8312 2.6482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1402 1.6971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8531 2.8561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7053 0.9307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4711 0.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1839 2.1130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2931 0.1217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9613 2.0644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2313 1.9785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9117 3.0632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1817 2.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7543 0.6217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5410 -1.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7084 -0.5756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3015 -2.7974 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.2247 0.1450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4929 1.1619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1211 1.5221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0219 3.5196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9815 -1.2419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8274 -1.7149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9948 -0.4790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7053 -0.6873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1762 0.4188 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5543 -1.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0317 -0.5594 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9925 -1.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9453 -0.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5774 -0.3902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8343 -1.0594 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1707 0.5233 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0144 -1.6384 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7543 -0.3783 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2029 -0.0629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6616 -1.1032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0498 -1.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3827 -1.9516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9723 4.5184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9724 -1.3762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2157 -2.5060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5556 -0.5982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8241 0.2206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 45 1 0 0 0 0 5 46 1 0 0 0 0 6 47 1 0 0 0 0 7 22 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 24 2 0 0 0 0 13 24 1 0 0 0 0 14 30 1 0 0 0 0 15 17 1 0 0 0 0 15 25 2 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 26 2 0 0 0 0 18 26 1 0 0 0 0 19 40 1 0 0 0 0 20 27 2 0 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 21 29 2 0 0 0 0 22 34 1 0 0 0 0 23 41 2 0 0 0 0 23 48 1 0 0 0 0 24 31 1 0 0 0 0 26 45 1 0 0 0 0 27 46 1 0 0 0 0 28 32 2 0 0 0 0 28 47 1 0 0 0 0 29 32 1 0 0 0 0 29 49 1 0 0 0 0 30 39 1 6 0 0 0 30 40 1 0 0 0 0 31 33 1 0 0 0 0 31 38 1 1 0 0 0 32 37 1 0 0 0 0 33 35 1 0 0 0 0 33 37 1 6 0 0 0 34 39 2 3 0 0 0 34 42 1 0 0 0 0 35 40 1 0 0 0 0 35 43 2 0 0 0 0 36 37 1 1 0 0 0 36 38 1 0 0 0 0 36 48 1 0 0 0 0 37 44 1 1 0 0 0 38 25 1 1 0 0 0 38 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	672.3
Volume:	683.933
LogP:	4.176
LogD:	3.751
LogS:	-5.367
# Rotatable Bonds:	13
TPSA:	132.86
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.296
Synthetic Accessibility Score:	5.385
Fsp3:	0.447
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:	-5.196
MDCK Permeability:	5.368030906538479e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.774

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	89.74982452392578%
Volume Distribution (VD):	1.022
Pgp-substrate:	2.0535361766815186%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.243
CYP2C19-inhibitor:	0.793
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.914
CYP2C9-substrate:	0.347
CYP2D6-inhibitor:	0.257
CYP2D6-substrate:	0.671
CYP3A4-inhibitor:	0.978
CYP3A4-substrate:	0.822

ADMET: Excretion

Clearance (CL):	4.458
Half-life (T1/2):	0.049

ADMET: Toxicity

hERG Blockers:	0.399
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.875
AMES Toxicity:	0.856
Rat Oral Acute Toxicity:	0.703
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.269
Carcinogencity:	0.123
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC293347

Natural Product ID:	NPC293347
*Common Name:**	4-Epiaglain A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HCNJABPCRMQADU-OIDMKLBVSA-N
Standard InCHI:	InChI=1S/C38H44N2O9/c1-7-22(2)34(42)39-30-14-11-19-40(30)35(43)33-31(24-12-9-8-10-13-24)38(25-15-17-26(45-4)18-16-25)36(48-23(3)41)37(33,44)32-28(47-6)20-27(46-5)21-29(32)49-38/h8-10,12-13,15-18,20-22,30-31,33,36,44H,7,11,14,19H2,1-6H3,(H,39,42)/t22?,30-,31+,33-,36-,37-,38-/m0/s1
SMILES:	COc1cc(OC)c2c(c1)O[C@@]1([C@H]([C@@]2(O)[C@@H]([C@H]1c1ccccc1)C(=O)N1CCC[C@H]1N=C(C(CC)C)O)OC(=O)C)c1ccc(cc1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL390233
PubChem CID:	44430534
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17055270]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO292	Aglaia elliptica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO292	Aglaia elliptica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10872	Aglaia ponapensis	Species	Meliaceae	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	5000.0	nM	PMID[524861]
NPT2	Others	Unspecified		IC50	>	5000.0	nM	PMID[524862]

☑ 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 NPC293347 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	277
0.1-0.2	1304
0.2-0.3	3594
0.3-0.4	10615
0.4-0.5	8899
0.5-0.6	10684
0.6-0.7	7242
0.7-0.8	66
0.8-0.85	6
0.85-0.9	3
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9679	High Similarity	NPC79130
0.9296	High Similarity	NPC475624
0.9247	High Similarity	NPC308709
0.915	High Similarity	NPC475292
0.915	High Similarity	NPC475349
0.915	High Similarity	NPC475565
0.9055	High Similarity	NPC475442
0.9005	High Similarity	NPC470846
0.8763	High Similarity	NPC206061
0.8492	Intermediate Similarity	NPC258128
0.8392	Intermediate Similarity	NPC169605
0.825	Intermediate Similarity	NPC235698
0.8186	Intermediate Similarity	NPC14390
0.8108	Intermediate Similarity	NPC329743
0.8065	Intermediate Similarity	NPC73422
0.8065	Intermediate Similarity	NPC310399
0.8063	Intermediate Similarity	NPC271755
0.8063	Intermediate Similarity	NPC254071
0.8063	Intermediate Similarity	NPC149502
0.8063	Intermediate Similarity	NPC222665
0.8021	Intermediate Similarity	NPC90336
0.8021	Intermediate Similarity	NPC470936
0.8011	Intermediate Similarity	NPC209473
0.801	Intermediate Similarity	NPC197125
0.8	Intermediate Similarity	NPC470847
0.787	Intermediate Similarity	NPC5674
0.7742	Intermediate Similarity	NPC87363
0.7659	Intermediate Similarity	NPC476661
0.7621	Intermediate Similarity	NPC476662
0.7576	Intermediate Similarity	NPC263955
0.7576	Intermediate Similarity	NPC23593
0.7538	Intermediate Similarity	NPC29587
0.7525	Intermediate Similarity	NPC107739
0.7514	Intermediate Similarity	NPC20360
0.75	Intermediate Similarity	NPC51543
0.75	Intermediate Similarity	NPC236089
0.745	Intermediate Similarity	NPC229234
0.7415	Intermediate Similarity	NPC471563
0.7391	Intermediate Similarity	NPC83019
0.7379	Intermediate Similarity	NPC470646
0.7356	Intermediate Similarity	NPC123859
0.7343	Intermediate Similarity	NPC204580
0.731	Intermediate Similarity	NPC475621
0.7304	Intermediate Similarity	NPC283207
0.7304	Intermediate Similarity	NPC29531
0.7304	Intermediate Similarity	NPC469437
0.729	Intermediate Similarity	NPC476496
0.7277	Intermediate Similarity	NPC326895
0.726	Intermediate Similarity	NPC144314
0.726	Intermediate Similarity	NPC281629
0.7243	Intermediate Similarity	NPC94687
0.7243	Intermediate Similarity	NPC476495
0.7243	Intermediate Similarity	NPC106840
0.7238	Intermediate Similarity	NPC242728
0.7225	Intermediate Similarity	NPC50548
0.7214	Intermediate Similarity	NPC309692
0.7212	Intermediate Similarity	NPC149962
0.7204	Intermediate Similarity	NPC184607
0.7194	Intermediate Similarity	NPC92589
0.7184	Intermediate Similarity	NPC473378
0.7184	Intermediate Similarity	NPC473407
0.7156	Intermediate Similarity	NPC471031
0.7156	Intermediate Similarity	NPC469689
0.7151	Intermediate Similarity	NPC470937
0.7129	Intermediate Similarity	NPC329816
0.7108	Intermediate Similarity	NPC315542
0.7107	Intermediate Similarity	NPC186228
0.7104	Intermediate Similarity	NPC82056
0.7101	Intermediate Similarity	NPC470642
0.71	Intermediate Similarity	NPC129578
0.71	Intermediate Similarity	NPC88378
0.71	Intermediate Similarity	NPC211713
0.7077	Intermediate Similarity	NPC165483
0.7075	Intermediate Similarity	NPC477551
0.7073	Intermediate Similarity	NPC276120
0.707	Intermediate Similarity	NPC80472
0.7062	Intermediate Similarity	NPC477552
0.7062	Intermediate Similarity	NPC477550
0.7059	Intermediate Similarity	NPC473562
0.7059	Intermediate Similarity	NPC307287
0.7053	Intermediate Similarity	NPC174122
0.7053	Intermediate Similarity	NPC64140
0.703	Intermediate Similarity	NPC91043
0.7014	Intermediate Similarity	NPC38964
0.7009	Intermediate Similarity	NPC286135
0.7005	Intermediate Similarity	NPC469479
0.7005	Intermediate Similarity	NPC234069
0.7005	Intermediate Similarity	NPC471395
0.7	Intermediate Similarity	NPC212697
0.6995	Remote Similarity	NPC475654
0.6991	Remote Similarity	NPC314946
0.6985	Remote Similarity	NPC90984
0.6984	Remote Similarity	NPC313414
0.6976	Remote Similarity	NPC477816
0.6976	Remote Similarity	NPC324220
0.6976	Remote Similarity	NPC312630
0.6965	Remote Similarity	NPC471165
0.6965	Remote Similarity	NPC26108
0.6965	Remote Similarity	NPC155506
0.6965	Remote Similarity	NPC159767
0.6959	Remote Similarity	NPC257266
0.6959	Remote Similarity	NPC56635
0.6957	Remote Similarity	NPC18306
0.695	Remote Similarity	NPC473009
0.6946	Remote Similarity	NPC120220
0.6946	Remote Similarity	NPC475421
0.6946	Remote Similarity	NPC180768
0.6942	Remote Similarity	NPC138083
0.6935	Remote Similarity	NPC97812
0.6935	Remote Similarity	NPC124747
0.6935	Remote Similarity	NPC109061
0.6935	Remote Similarity	NPC155754
0.6931	Remote Similarity	NPC215802
0.6931	Remote Similarity	NPC167231
0.6927	Remote Similarity	NPC470903
0.6927	Remote Similarity	NPC167763
0.6927	Remote Similarity	NPC257728
0.6927	Remote Similarity	NPC470112
0.6923	Remote Similarity	NPC315253
0.6923	Remote Similarity	NPC473236
0.6919	Remote Similarity	NPC94220
0.6919	Remote Similarity	NPC24339
0.6919	Remote Similarity	NPC179250
0.6919	Remote Similarity	NPC7543
0.6919	Remote Similarity	NPC50380
0.6919	Remote Similarity	NPC254700
0.6919	Remote Similarity	NPC98083
0.6919	Remote Similarity	NPC264938
0.6919	Remote Similarity	NPC166456
0.6915	Remote Similarity	NPC473010
0.6915	Remote Similarity	NPC137627
0.6912	Remote Similarity	NPC472584
0.6912	Remote Similarity	NPC477529
0.6912	Remote Similarity	NPC32064
0.6904	Remote Similarity	NPC129053
0.6904	Remote Similarity	NPC109967
0.6904	Remote Similarity	NPC475797
0.6904	Remote Similarity	NPC321372
0.6904	Remote Similarity	NPC78554
0.6904	Remote Similarity	NPC474738
0.6904	Remote Similarity	NPC55463
0.6904	Remote Similarity	NPC474609
0.6904	Remote Similarity	NPC67080
0.6904	Remote Similarity	NPC469936
0.6904	Remote Similarity	NPC471787
0.6904	Remote Similarity	NPC166116
0.69	Remote Similarity	NPC196091
0.69	Remote Similarity	NPC473012
0.6897	Remote Similarity	NPC217378
0.6897	Remote Similarity	NPC329992
0.6897	Remote Similarity	NPC102810
0.6895	Remote Similarity	NPC153365
0.6893	Remote Similarity	NPC294951
0.689	Remote Similarity	NPC106700
0.6884	Remote Similarity	NPC53889
0.6884	Remote Similarity	NPC316164
0.6881	Remote Similarity	NPC9309
0.6881	Remote Similarity	NPC82330
0.6881	Remote Similarity	NPC476227
0.6881	Remote Similarity	NPC473354
0.6881	Remote Similarity	NPC473402
0.6881	Remote Similarity	NPC164608
0.6872	Remote Similarity	NPC316960
0.6872	Remote Similarity	NPC78835
0.6872	Remote Similarity	NPC178484
0.6872	Remote Similarity	NPC309512
0.6872	Remote Similarity	NPC148945
0.6872	Remote Similarity	NPC317715
0.6872	Remote Similarity	NPC472636
0.6872	Remote Similarity	NPC204561
0.6869	Remote Similarity	NPC322459
0.6869	Remote Similarity	NPC271741
0.6869	Remote Similarity	NPC293164
0.6869	Remote Similarity	NPC318527
0.6869	Remote Similarity	NPC160512
0.6869	Remote Similarity	NPC38779
0.6869	Remote Similarity	NPC289322
0.6869	Remote Similarity	NPC471394
0.6869	Remote Similarity	NPC156818
0.6869	Remote Similarity	NPC114179
0.6869	Remote Similarity	NPC324358
0.6869	Remote Similarity	NPC68324
0.6869	Remote Similarity	NPC287789
0.6869	Remote Similarity	NPC323627
0.6866	Remote Similarity	NPC230611
0.6866	Remote Similarity	NPC328494
0.6866	Remote Similarity	NPC89831
0.6866	Remote Similarity	NPC214279
0.6863	Remote Similarity	NPC8704
0.6863	Remote Similarity	NPC476365
0.6863	Remote Similarity	NPC76047
0.6863	Remote Similarity	NPC287884
0.6863	Remote Similarity	NPC45037
0.6863	Remote Similarity	NPC472159
0.6856	Remote Similarity	NPC314987
0.6854	Remote Similarity	NPC234318
0.6853	Remote Similarity	NPC469934
0.6853	Remote Similarity	NPC279218
0.6853	Remote Similarity	NPC108937
0.6852	Remote Similarity	NPC311357

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 NPC293347 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	545
0.2-0.3	1063
0.3-0.4	2477
0.4-0.5	2726
0.5-0.6	1698
0.6-0.7	465
0.7-0.8	6
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
0.7225	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7497	Discontinued
0.7208	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7811	Phase 3
0.719	Intermediate Similarity	NPD7810	Phase 3
0.7178	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7608	Discontinued
0.7108	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7584	Approved
0.702	Intermediate Similarity	NPD7199	Phase 2
0.701	Intermediate Similarity	NPD7549	Discontinued
0.6985	Remote Similarity	NPD7315	Approved
0.6971	Remote Similarity	NPD7861	Discontinued
0.6968	Remote Similarity	NPD7466	Approved
0.6959	Remote Similarity	NPD7583	Approved
0.695	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8059	Phase 3
0.693	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7585	Approved
0.6919	Remote Similarity	NPD4360	Phase 2
0.6919	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4363	Phase 3
0.6888	Remote Similarity	NPD7972	Discontinued
0.6856	Remote Similarity	NPD8469	Approved
0.6853	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7177	Discontinued
0.6825	Remote Similarity	NPD7296	Approved
0.6823	Remote Similarity	NPD7447	Phase 1
0.6818	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7930	Approved
0.6808	Remote Similarity	NPD4361	Phase 2
0.6808	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2494	Approved
0.6806	Remote Similarity	NPD6666	Approved
0.6806	Remote Similarity	NPD6667	Approved
0.6806	Remote Similarity	NPD2493	Approved
0.6802	Remote Similarity	NPD7827	Phase 1
0.68	Remote Similarity	NPD6746	Phase 2
0.6791	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4582	Approved
0.6789	Remote Similarity	NPD4583	Approved
0.6784	Remote Similarity	NPD7075	Discontinued
0.6776	Remote Similarity	NPD2973	Approved
0.6776	Remote Similarity	NPD2974	Approved
0.6776	Remote Similarity	NPD2975	Approved
0.6774	Remote Similarity	NPD6863	Phase 2
0.6772	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7213	Phase 3
0.6771	Remote Similarity	NPD7212	Phase 2
0.6765	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4580	Approved
0.6757	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7801	Approved
0.6757	Remote Similarity	NPD7783	Phase 2
0.6753	Remote Similarity	NPD7427	Discontinued
0.6751	Remote Similarity	NPD7577	Discontinued
0.6743	Remote Similarity	NPD4002	Approved
0.6743	Remote Similarity	NPD4004	Approved
0.6742	Remote Similarity	NPD8151	Discontinued
0.6736	Remote Similarity	NPD7020	Approved
0.6736	Remote Similarity	NPD7019	Approved
0.6735	Remote Similarity	NPD6502	Phase 2
0.6728	Remote Similarity	NPD3452	Approved
0.6728	Remote Similarity	NPD3450	Approved
0.6718	Remote Similarity	NPD4210	Discontinued
0.6717	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD4466	Phase 1
0.6713	Remote Similarity	NPD7565	Approved
0.6701	Remote Similarity	NPD6072	Discontinued
0.6701	Remote Similarity	NPD7411	Suspended
0.67	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD8053	Approved
0.6699	Remote Similarity	NPD8054	Approved
0.6698	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5006	Approved
0.6697	Remote Similarity	NPD5005	Approved
0.6684	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8161	Suspended
0.6667	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7874	Approved
0.6637	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7047	Phase 3
0.6636	Remote Similarity	NPD8285	Discontinued
0.6635	Remote Similarity	NPD7685	Pre-registration
0.6633	Remote Similarity	NPD7819	Suspended
0.6633	Remote Similarity	NPD5773	Approved
0.6633	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5772	Approved
0.6622	Remote Similarity	NPD7701	Phase 2
0.662	Remote Similarity	NPD2490	Approved
0.662	Remote Similarity	NPD6504	Approved
0.662	Remote Similarity	NPD2488	Approved
0.662	Remote Similarity	NPD6505	Approved
0.6619	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD3749	Approved
0.6609	Remote Similarity	NPD6997	Phase 2
0.6604	Remote Similarity	NPD7906	Approved
0.6602	Remote Similarity	NPD6620	Discovery
0.6602	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7228	Approved
0.6595	Remote Similarity	NPD8491	Approved
0.6585	Remote Similarity	NPD6166	Phase 2
0.6585	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6234	Discontinued
0.6583	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7131	Phase 3
0.6573	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7280	Phase 3
0.6571	Remote Similarity	NPD7281	Phase 3
0.657	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6020	Phase 2
0.657	Remote Similarity	NPD8156	Discontinued
0.6569	Remote Similarity	NPD7229	Phase 3
0.6569	Remote Similarity	NPD5711	Approved
0.6569	Remote Similarity	NPD5710	Approved
0.6567	Remote Similarity	NPD7768	Phase 2
0.6567	Remote Similarity	NPD4967	Phase 2
0.6567	Remote Similarity	NPD4966	Approved
0.6567	Remote Similarity	NPD4965	Approved
0.6566	Remote Similarity	NPD4380	Phase 2
0.6561	Remote Similarity	NPD8319	Approved
0.6561	Remote Similarity	NPD8320	Phase 1
0.6552	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8455	Phase 2
0.6545	Remote Similarity	NPD6004	Phase 3
0.6545	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6002	Phase 3
0.6545	Remote Similarity	NPD6005	Phase 3
0.6543	Remote Similarity	NPD6355	Discontinued
0.6538	Remote Similarity	NPD5557	Phase 1
0.6535	Remote Similarity	NPD6971	Discontinued
0.6535	Remote Similarity	NPD8070	Approved
0.6526	Remote Similarity	NPD7033	Discontinued
0.6524	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8251	Approved
0.6522	Remote Similarity	NPD8099	Discontinued
0.6522	Remote Similarity	NPD8252	Approved
0.6517	Remote Similarity	NPD5353	Approved
0.6516	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4420	Approved
0.6507	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6315	Phase 2
0.65	Remote Similarity	NPD37	Approved
0.65	Remote Similarity	NPD6801	Discontinued
0.65	Remote Similarity	NPD6844	Discontinued
0.65	Remote Similarity	NPD1934	Approved
0.6495	Remote Similarity	NPD6836	Approved
0.6494	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD8366	Approved
0.6494	Remote Similarity	NPD7907	Approved
0.6493	Remote Similarity	NPD2968	Approved
0.6493	Remote Similarity	NPD2971	Approved
0.6492	Remote Similarity	NPD6032	Approved
0.649	Remote Similarity	NPD5313	Approved
0.649	Remote Similarity	NPD5312	Approved
0.649	Remote Similarity	NPD5844	Phase 1
0.6489	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7048	Phase 3
0.6484	Remote Similarity	NPD6874	Approved
0.648	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD8150	Discontinued
0.6477	Remote Similarity	NPD2654	Approved
0.6476	Remote Similarity	NPD4377	Discontinued
0.6473	Remote Similarity	NPD7473	Discontinued
0.6471	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6823	Phase 2
0.6471	Remote Similarity	NPD8162	Phase 2
0.6471	Remote Similarity	NPD5494	Approved
0.6468	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD8404	Phase 2
0.6459	Remote Similarity	NPD5484	Approved
0.6459	Remote Similarity	NPD7074	Phase 3
0.6459	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD5485	Approved
0.6457	Remote Similarity	NPD7999	Approved
0.6455	Remote Similarity	NPD4622	Approved
0.6455	Remote Similarity	NPD4618	Approved
0.6452	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4908	Phase 1
0.645	Remote Similarity	NPD7110	Phase 1
0.645	Remote Similarity	NPD6385	Approved
0.645	Remote Similarity	NPD6677	Suspended
0.645	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6386	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