NPASS Compound

Structure

CID225049 OpenBabel06191716022D 30 35 0 0 1 0 0 0 0 0999 V2000 2.4939 -3.7856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3311 -3.4126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5489 -2.2900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0264 -1.8486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1280 -2.1323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3819 -0.4579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3819 -1.3747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1757 -0.9163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5877 -0.9165 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1754 0.0004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3817 0.4585 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9697 -1.3745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9693 0.4590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3815 1.3753 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7635 -0.9160 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7633 0.0008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5875 1.8337 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7938 1.3753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5894 -2.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7940 -1.3749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5879 0.0002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7937 0.4584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9699 -2.3391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9691 1.4236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1970 1.8463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -2.7785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0220 0.9290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5574 -0.4574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7937 2.2919 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 6 2 0 0 0 0 5 19 1 0 0 0 0 6 21 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 12 1 0 0 0 0 9 20 1 0 0 0 0 9 21 1 6 0 0 0 10 8 1 6 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 1 0 0 0 12 23 2 0 0 0 0 13 16 1 0 0 0 0 13 24 1 1 0 0 0 14 17 1 0 0 0 0 14 25 1 6 0 0 0 15 12 1 6 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 28 1 6 0 0 0 17 18 1 0 0 0 0 17 29 1 1 0 0 0 18 22 1 1 0 0 0 18 29 1 0 0 0 0 19 26 1 0 0 0 0 20 30 1 0 0 0 0 21 22 1 6 0 0 0 22 27 1 6 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	400.142
LogP:	0.93
LogD:	0.399
LogS:	-2.169
# Rotatable Bonds:	2
TPSA:	132.28
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.345
Synthetic Accessibility Score:	6.056
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.563
MDCK Permeability:	0.00015787174925208092
Pgp-inhibitor:	0.0
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.163
20% Bioavailability (F20%):	0.06
30% Bioavailability (F30%):	0.55

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206
Plasma Protein Binding (PPB):	70.76590728759766%
Volume Distribution (VD):	0.544
Pgp-substrate:	29.533710479736328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.728
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.523
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.099

ADMET: Excretion

Clearance (CL):	2.424
Half-life (T1/2):	0.215

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.861
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.697
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.075
Carcinogencity:	0.369
Eye Corrosion:	0.123
Eye Irritation:	0.012
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC225049

Natural Product ID:	NPC225049
*Common Name:**	Panepophenanthrine
IUPAC Name:	n.a.
Synonyms:	Panepophenanthrine
Standard InCHIKey:	WQBRQZUREPTGLI-ODDMXWQNSA-N
Standard InCHI:	InChI=1S/C22H28O8/c1-19(2,26)5-6-21-9-7-8-10(13(24)16-15(28-16)12(8)23)11(21)14(25)17-18(29-17)22(21,27)30-20(9,3)4/h5-7,9-11,13-18,24-27H,1-4H3/b6-5+/t9-,10-,11-,13-,14-,15-,16+,17+,18+,21-,22+/m1/s1
SMILES:	O[C@H]1[C@@H]2O[C@@H]2[C@]2([C@]3([C@@H]1[C@@H]1[C@@H](O)[C@@H]4O[C@@H]4C(=O)C1=C[C@@H]3C(O2)(C)C)/C=C/C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2046774
PubChem CID:	10432257
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593285]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[20000782]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2095371]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22695182]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2809606]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623037]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868162]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO11186	Duranta erecta	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11186	Duranta erecta	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1904	Anaxeton arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2838	Verbena officinalis	Species	Verbenaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5282	Individual Protein	Ubiquitin-like modifier-activating enzyme 1	Homo sapiens	IC50	=	40000.0	nM	PMID[566527]

☑ 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 NPC225049 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	273
0.1-0.2	1541
0.2-0.3	4424
0.3-0.4	7725
0.4-0.5	12511
0.5-0.6	9176
0.6-0.7	5412
0.7-0.8	1487
0.8-0.85	137
0.85-0.9	7
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9304	High Similarity	NPC477116
0.9304	High Similarity	NPC27999
0.8992	High Similarity	NPC102822
0.8992	High Similarity	NPC477046
0.8908	High Similarity	NPC112038
0.8824	High Similarity	NPC268958
0.8824	High Similarity	NPC469488
0.877	High Similarity	NPC470922
0.8739	High Similarity	NPC188667
0.8739	High Similarity	NPC251310
0.8739	High Similarity	NPC204552
0.8729	High Similarity	NPC179626
0.8718	High Similarity	NPC477266
0.8655	High Similarity	NPC470775
0.8655	High Similarity	NPC474654
0.8655	High Similarity	NPC176513
0.8655	High Similarity	NPC97908
0.8655	High Similarity	NPC470854
0.8655	High Similarity	NPC122033
0.8655	High Similarity	NPC287343
0.8618	High Similarity	NPC24651
0.8583	High Similarity	NPC240509
0.8583	High Similarity	NPC17772
0.8583	High Similarity	NPC297179
0.8583	High Similarity	NPC470776
0.8537	High Similarity	NPC67251
0.8534	High Similarity	NPC87335
0.8512	High Similarity	NPC470777
0.8504	High Similarity	NPC102316
0.85	High Similarity	NPC469684
0.85	High Similarity	NPC58662
0.8487	Intermediate Similarity	NPC80650
0.8475	Intermediate Similarity	NPC472002
0.8468	Intermediate Similarity	NPC476729
0.8455	Intermediate Similarity	NPC312833
0.8443	Intermediate Similarity	NPC107338
0.8443	Intermediate Similarity	NPC109607
0.8438	Intermediate Similarity	NPC168879
0.8425	Intermediate Similarity	NPC476862
0.8425	Intermediate Similarity	NPC476863
0.8425	Intermediate Similarity	NPC476852
0.8417	Intermediate Similarity	NPC474734
0.8417	Intermediate Similarity	NPC259306
0.8417	Intermediate Similarity	NPC152199
0.8417	Intermediate Similarity	NPC474046
0.8417	Intermediate Similarity	NPC96312
0.8417	Intermediate Similarity	NPC251236
0.8417	Intermediate Similarity	NPC40632
0.8417	Intermediate Similarity	NPC134869
0.8417	Intermediate Similarity	NPC235539
0.8417	Intermediate Similarity	NPC328374
0.8417	Intermediate Similarity	NPC470628
0.8417	Intermediate Similarity	NPC207217
0.8413	Intermediate Similarity	NPC476859
0.8403	Intermediate Similarity	NPC49451
0.8403	Intermediate Similarity	NPC7921
0.8403	Intermediate Similarity	NPC208998
0.8403	Intermediate Similarity	NPC51978
0.84	Intermediate Similarity	NPC293112
0.839	Intermediate Similarity	NPC474229
0.8387	Intermediate Similarity	NPC91693
0.8387	Intermediate Similarity	NPC105926
0.8387	Intermediate Similarity	NPC265557
0.8387	Intermediate Similarity	NPC18945
0.8385	Intermediate Similarity	NPC243014
0.8361	Intermediate Similarity	NPC475775
0.8361	Intermediate Similarity	NPC476529
0.8359	Intermediate Similarity	NPC254146
0.8359	Intermediate Similarity	NPC33378
0.8359	Intermediate Similarity	NPC6274
0.8346	Intermediate Similarity	NPC162495
0.8346	Intermediate Similarity	NPC476851
0.8333	Intermediate Similarity	NPC474906
0.8333	Intermediate Similarity	NPC305496
0.8333	Intermediate Similarity	NPC117712
0.8333	Intermediate Similarity	NPC473798
0.8333	Intermediate Similarity	NPC470919
0.8333	Intermediate Similarity	NPC469877
0.8333	Intermediate Similarity	NPC18547
0.832	Intermediate Similarity	NPC81736
0.832	Intermediate Similarity	NPC172154
0.8319	Intermediate Similarity	NPC289312
0.8319	Intermediate Similarity	NPC474516
0.8319	Intermediate Similarity	NPC11252
0.8319	Intermediate Similarity	NPC302146
0.8306	Intermediate Similarity	NPC222688
0.8305	Intermediate Similarity	NPC474567
0.8293	Intermediate Similarity	NPC478051
0.8281	Intermediate Similarity	NPC251564
0.8281	Intermediate Similarity	NPC477189
0.8281	Intermediate Similarity	NPC475314
0.8281	Intermediate Similarity	NPC476855
0.8281	Intermediate Similarity	NPC475606
0.8279	Intermediate Similarity	NPC284707
0.8279	Intermediate Similarity	NPC21326
0.8264	Intermediate Similarity	NPC270478
0.8264	Intermediate Similarity	NPC477509
0.8254	Intermediate Similarity	NPC473635
0.8254	Intermediate Similarity	NPC217901
0.825	Intermediate Similarity	NPC198539
0.825	Intermediate Similarity	NPC33360
0.825	Intermediate Similarity	NPC477126
0.8244	Intermediate Similarity	NPC68282
0.824	Intermediate Similarity	NPC11895
0.824	Intermediate Similarity	NPC469789
0.8235	Intermediate Similarity	NPC146945
0.8235	Intermediate Similarity	NPC471243
0.8235	Intermediate Similarity	NPC201992
0.8235	Intermediate Similarity	NPC171888
0.8235	Intermediate Similarity	NPC476023
0.8226	Intermediate Similarity	NPC472401
0.8226	Intermediate Similarity	NPC470779
0.822	Intermediate Similarity	NPC141350
0.8217	Intermediate Similarity	NPC180902
0.8217	Intermediate Similarity	NPC473485
0.8217	Intermediate Similarity	NPC475139
0.8217	Intermediate Similarity	NPC474508
0.8217	Intermediate Similarity	NPC254614
0.8217	Intermediate Similarity	NPC100390
0.8217	Intermediate Similarity	NPC476193
0.8205	Intermediate Similarity	NPC144854
0.8205	Intermediate Similarity	NPC3316
0.8203	Intermediate Similarity	NPC476854
0.8203	Intermediate Similarity	NPC470880
0.8197	Intermediate Similarity	NPC13713
0.8197	Intermediate Similarity	NPC473590
0.8197	Intermediate Similarity	NPC218970
0.8197	Intermediate Similarity	NPC473968
0.8197	Intermediate Similarity	NPC53396
0.8197	Intermediate Similarity	NPC98249
0.8197	Intermediate Similarity	NPC296822
0.8189	Intermediate Similarity	NPC470780
0.8189	Intermediate Similarity	NPC475273
0.8189	Intermediate Similarity	NPC473253
0.8189	Intermediate Similarity	NPC470882
0.8189	Intermediate Similarity	NPC168849
0.8182	Intermediate Similarity	NPC143268
0.8182	Intermediate Similarity	NPC247069
0.8182	Intermediate Similarity	NPC261330
0.8182	Intermediate Similarity	NPC596
0.8182	Intermediate Similarity	NPC45218
0.8182	Intermediate Similarity	NPC268238
0.8182	Intermediate Similarity	NPC323821
0.8182	Intermediate Similarity	NPC295885
0.8182	Intermediate Similarity	NPC140045
0.8175	Intermediate Similarity	NPC8369
0.8175	Intermediate Similarity	NPC473709
0.8175	Intermediate Similarity	NPC473919
0.8174	Intermediate Similarity	NPC478176
0.8167	Intermediate Similarity	NPC317687
0.8167	Intermediate Similarity	NPC90769
0.8167	Intermediate Similarity	NPC269530
0.8167	Intermediate Similarity	NPC42658
0.816	Intermediate Similarity	NPC170538
0.816	Intermediate Similarity	NPC23786
0.816	Intermediate Similarity	NPC19464
0.816	Intermediate Similarity	NPC470265
0.8151	Intermediate Similarity	NPC5103
0.8151	Intermediate Similarity	NPC253906
0.8136	Intermediate Similarity	NPC154608
0.8136	Intermediate Similarity	NPC192813
0.8136	Intermediate Similarity	NPC277017
0.8125	Intermediate Similarity	NPC477713
0.8125	Intermediate Similarity	NPC473620
0.8125	Intermediate Similarity	NPC477712
0.8115	Intermediate Similarity	NPC16081
0.8115	Intermediate Similarity	NPC474333
0.8115	Intermediate Similarity	NPC173686
0.8106	Intermediate Similarity	NPC141215
0.8106	Intermediate Similarity	NPC190065
0.8106	Intermediate Similarity	NPC471089
0.8106	Intermediate Similarity	NPC251998
0.8103	Intermediate Similarity	NPC131366
0.8099	Intermediate Similarity	NPC73300
0.8099	Intermediate Similarity	NPC108721
0.8099	Intermediate Similarity	NPC317210
0.8095	Intermediate Similarity	NPC120724
0.8095	Intermediate Similarity	NPC472399
0.8095	Intermediate Similarity	NPC473802
0.8092	Intermediate Similarity	NPC15215
0.8092	Intermediate Similarity	NPC475500
0.8092	Intermediate Similarity	NPC471136
0.8092	Intermediate Similarity	NPC100017
0.8092	Intermediate Similarity	NPC475154
0.8092	Intermediate Similarity	NPC182266
0.8092	Intermediate Similarity	NPC242486
0.8092	Intermediate Similarity	NPC471137
0.8092	Intermediate Similarity	NPC223356
0.8092	Intermediate Similarity	NPC473548
0.8083	Intermediate Similarity	NPC469656
0.8083	Intermediate Similarity	NPC157476
0.8083	Intermediate Similarity	NPC469655
0.8083	Intermediate Similarity	NPC317107
0.8083	Intermediate Similarity	NPC474846
0.808	Intermediate Similarity	NPC67569
0.8067	Intermediate Similarity	NPC472534
0.8067	Intermediate Similarity	NPC220705
0.8067	Intermediate Similarity	NPC143706
0.8067	Intermediate Similarity	NPC20192
0.8062	Intermediate Similarity	NPC264192

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 NPC225049 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	1722
0.2-0.3	3865
0.3-0.4	2177
0.4-0.5	657
0.5-0.6	285
0.6-0.7	146
0.7-0.8	55
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
0.8145	Intermediate Similarity	NPD6054	Approved
0.808	Intermediate Similarity	NPD6016	Approved
0.808	Intermediate Similarity	NPD6015	Approved
0.8016	Intermediate Similarity	NPD6370	Approved
0.8016	Intermediate Similarity	NPD5988	Approved
0.8	Intermediate Similarity	NPD6319	Approved
0.7917	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD7492	Approved
0.7857	Intermediate Similarity	NPD6059	Approved
0.7851	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6616	Approved
0.7769	Intermediate Similarity	NPD7078	Approved
0.776	Intermediate Similarity	NPD7115	Discovery
0.771	Intermediate Similarity	NPD7736	Approved
0.7686	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD8328	Phase 3
0.7619	Intermediate Similarity	NPD6009	Approved
0.7603	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD8297	Approved
0.7581	Intermediate Similarity	NPD6882	Approved
0.7561	Intermediate Similarity	NPD4634	Approved
0.752	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7459	Intermediate Similarity	NPD5697	Approved
0.7417	Intermediate Similarity	NPD5211	Phase 2
0.7398	Intermediate Similarity	NPD6881	Approved
0.7398	Intermediate Similarity	NPD6899	Approved
0.7344	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6013	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6012	Approved
0.7333	Intermediate Similarity	NPD5344	Discontinued
0.7313	Intermediate Similarity	NPD6033	Approved
0.7311	Intermediate Similarity	NPD4225	Approved
0.7295	Intermediate Similarity	NPD5141	Approved
0.728	Intermediate Similarity	NPD7290	Approved
0.728	Intermediate Similarity	NPD7102	Approved
0.728	Intermediate Similarity	NPD6883	Approved
0.7273	Intermediate Similarity	NPD7604	Phase 2
0.7259	Intermediate Similarity	NPD7319	Approved
0.7258	Intermediate Similarity	NPD6011	Approved
0.7252	Intermediate Similarity	NPD5983	Phase 2
0.725	Intermediate Similarity	NPD5286	Approved
0.725	Intermediate Similarity	NPD5285	Approved
0.725	Intermediate Similarity	NPD4696	Approved
0.7236	Intermediate Similarity	NPD5739	Approved
0.7236	Intermediate Similarity	NPD6402	Approved
0.7236	Intermediate Similarity	NPD6008	Approved
0.7236	Intermediate Similarity	NPD7128	Approved
0.7236	Intermediate Similarity	NPD6675	Approved
0.7222	Intermediate Similarity	NPD6847	Approved
0.7222	Intermediate Similarity	NPD6617	Approved
0.7222	Intermediate Similarity	NPD6869	Approved
0.7222	Intermediate Similarity	NPD8130	Phase 1
0.7177	Intermediate Similarity	NPD5701	Approved
0.7131	Intermediate Similarity	NPD5224	Approved
0.7131	Intermediate Similarity	NPD5226	Approved
0.7131	Intermediate Similarity	NPD4633	Approved
0.7131	Intermediate Similarity	NPD5225	Approved
0.7121	Intermediate Similarity	NPD8516	Approved
0.7121	Intermediate Similarity	NPD6921	Approved
0.7121	Intermediate Similarity	NPD8517	Approved
0.7121	Intermediate Similarity	NPD8513	Phase 3
0.7121	Intermediate Similarity	NPD8515	Approved
0.712	Intermediate Similarity	NPD7320	Approved
0.712	Intermediate Similarity	NPD6686	Approved
0.7083	Intermediate Similarity	NPD4755	Approved
0.7073	Intermediate Similarity	NPD5174	Approved
0.7073	Intermediate Similarity	NPD5175	Approved
0.7049	Intermediate Similarity	NPD5223	Approved
0.704	Intermediate Similarity	NPD6412	Phase 2
0.7037	Intermediate Similarity	NPD6336	Discontinued
0.7037	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5221	Approved
0.6984	Remote Similarity	NPD4730	Approved
0.6984	Remote Similarity	NPD4729	Approved
0.6967	Remote Similarity	NPD4700	Approved
0.6967	Remote Similarity	NPD6648	Approved
0.6957	Remote Similarity	NPD5956	Approved
0.6942	Remote Similarity	NPD5173	Approved
0.6929	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5250	Approved
0.6875	Remote Similarity	NPD5247	Approved
0.6875	Remote Similarity	NPD5249	Phase 3
0.6875	Remote Similarity	NPD5251	Approved
0.6875	Remote Similarity	NPD5248	Approved
0.687	Remote Similarity	NPD6274	Approved
0.6861	Remote Similarity	NPD8074	Phase 3
0.686	Remote Similarity	NPD4697	Phase 3
0.6842	Remote Similarity	NPD7101	Approved
0.6842	Remote Similarity	NPD7516	Approved
0.6842	Remote Similarity	NPD7100	Approved
0.6833	Remote Similarity	NPD5282	Discontinued
0.6825	Remote Similarity	NPD4768	Approved
0.6825	Remote Similarity	NPD4767	Approved
0.6822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6317	Approved
0.6807	Remote Similarity	NPD6079	Approved
0.6767	Remote Similarity	NPD6313	Approved
0.6767	Remote Similarity	NPD7328	Approved
0.6767	Remote Similarity	NPD6335	Approved
0.6767	Remote Similarity	NPD6314	Approved
0.6767	Remote Similarity	NPD7327	Approved
0.6744	Remote Similarity	NPD6371	Approved
0.6741	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5128	Approved
0.6694	Remote Similarity	NPD7640	Approved
0.6694	Remote Similarity	NPD7639	Approved
0.6692	Remote Similarity	NPD5217	Approved
0.6692	Remote Similarity	NPD5216	Approved
0.6692	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD4754	Approved
0.6641	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4629	Approved
0.6639	Remote Similarity	NPD5210	Approved
0.6639	Remote Similarity	NPD5328	Approved
0.6618	Remote Similarity	NPD7503	Approved
0.6617	Remote Similarity	NPD6868	Approved
0.6615	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5135	Approved
0.6615	Remote Similarity	NPD5169	Approved
0.6613	Remote Similarity	NPD7638	Approved
0.6613	Remote Similarity	NPD5696	Approved
0.6612	Remote Similarity	NPD5778	Approved
0.6612	Remote Similarity	NPD5779	Approved
0.6565	Remote Similarity	NPD5127	Approved
0.6549	Remote Similarity	NPD7260	Phase 2
0.6532	Remote Similarity	NPD7902	Approved
0.6529	Remote Similarity	NPD7983	Approved
0.6525	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6067	Discontinued
0.6509	Remote Similarity	NPD8407	Phase 2
0.6508	Remote Similarity	NPD1700	Approved
0.6504	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD4753	Phase 2
0.6496	Remote Similarity	NPD8335	Approved
0.6496	Remote Similarity	NPD8379	Approved
0.6496	Remote Similarity	NPD6909	Approved
0.6496	Remote Similarity	NPD8378	Approved
0.6496	Remote Similarity	NPD8380	Approved
0.6496	Remote Similarity	NPD6908	Approved
0.6496	Remote Similarity	NPD8296	Approved
0.6496	Remote Similarity	NPD8033	Approved
0.6475	Remote Similarity	NPD4202	Approved
0.6475	Remote Similarity	NPD6399	Phase 3
0.6471	Remote Similarity	NPD3573	Approved
0.6471	Remote Similarity	NPD4522	Approved
0.6462	Remote Similarity	NPD5168	Approved
0.6446	Remote Similarity	NPD46	Approved
0.6446	Remote Similarity	NPD6698	Approved
0.6446	Remote Similarity	NPD3168	Discontinued
0.6438	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8368	Discontinued
0.6423	Remote Similarity	NPD8294	Approved
0.6423	Remote Similarity	NPD7748	Approved
0.6423	Remote Similarity	NPD8377	Approved
0.6418	Remote Similarity	NPD5167	Approved
0.6395	Remote Similarity	NPD6333	Approved
0.6395	Remote Similarity	NPD6334	Approved
0.6393	Remote Similarity	NPD7515	Phase 2
0.6393	Remote Similarity	NPD6411	Approved
0.6343	Remote Similarity	NPD8133	Approved
0.6325	Remote Similarity	NPD3667	Approved
0.6303	Remote Similarity	NPD1696	Phase 3
0.6303	Remote Similarity	NPD1694	Approved
0.6293	Remote Similarity	NPD4695	Discontinued
0.629	Remote Similarity	NPD7900	Approved
0.629	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7799	Discontinued
0.6281	Remote Similarity	NPD6672	Approved
0.6281	Remote Similarity	NPD5737	Approved
0.6276	Remote Similarity	NPD6845	Suspended
0.6271	Remote Similarity	NPD6110	Phase 1
0.6269	Remote Similarity	NPD6053	Discontinued
0.626	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD4519	Discontinued
0.625	Remote Similarity	NPD4623	Approved
0.6243	Remote Similarity	NPD8434	Phase 2
0.624	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6101	Approved
0.623	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4786	Approved
0.6218	Remote Similarity	NPD3666	Approved
0.6218	Remote Similarity	NPD3133	Approved
0.6218	Remote Similarity	NPD3665	Phase 1
0.6202	Remote Similarity	NPD7632	Discontinued
0.6198	Remote Similarity	NPD7524	Approved
0.619	Remote Similarity	NPD3751	Discontinued

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