NPASS Compound

Structure

NPC273798 OpenBabel07101718282D 45 48 0 0 1 0 0 0 0 0999 V2000 2.0906 2.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2246 4.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1896 2.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9359 3.6716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 4.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1055 2.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5539 0.6733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1886 -0.2575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3586 2.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5075 3.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5357 -2.1545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5075 -2.3901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5278 1.9883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5560 2.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3735 1.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9437 -0.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2246 3.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2178 2.7121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 3.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3735 2.7930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2538 -1.1950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5075 1.2930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1975 -1.6662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9156 -0.7067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2819 -0.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1693 -1.9018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6055 0.0171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4080 -1.6833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7709 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 2 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 23 2 0 0 0 0 6 23 1 0 0 0 0 7 35 1 0 0 0 0 8 35 1 0 0 0 0 9 36 1 0 0 0 0 10 36 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 13 14 2 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 22 2 0 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 18 29 1 0 0 0 0 19 27 1 0 0 0 0 19 30 1 0 0 0 0 20 26 1 0 0 0 0 20 37 1 0 0 0 0 23 24 1 0 0 0 0 24 12 1 1 0 0 0 25 31 1 0 0 0 0 26 17 1 6 0 0 0 26 35 1 0 0 0 0 27 32 1 0 0 0 0 27 33 2 0 0 0 0 28 29 2 0 0 0 0 28 39 1 0 0 0 0 29 40 1 0 0 0 0 30 36 1 1 0 0 0 30 45 1 0 0 0 0 31 41 2 0 0 0 0 32 38 1 0 0 0 0 32 42 2 0 0 0 0 33 37 1 0 0 0 0 33 45 1 0 0 0 0 34 37 1 0 0 0 0 34 38 1 0 0 0 0 34 43 2 0 0 0 0 35 38 1 0 0 0 0 36 44 1 0 0 0 0 37 16 1 6 0 0 0 38 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.36
Volume:	666.745
LogP:	7.058
LogD:	4.933
LogS:	-4.774
# Rotatable Bonds:	11
TPSA:	121.13
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.101
Synthetic Accessibility Score:	6.038
Fsp3:	0.553
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.055
MDCK Permeability:	1.1522489330673125e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.323

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	93.65218353271484%
Volume Distribution (VD):	1.652
Pgp-substrate:	4.995388984680176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.25
CYP2C19-inhibitor:	0.413
CYP2C19-substrate:	0.577
CYP2C9-inhibitor:	0.85
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.639
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.858
CYP3A4-substrate:	0.884

ADMET: Excretion

Clearance (CL):	10.63
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.907
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.608
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.106
Carcinogencity:	0.654
Eye Corrosion:	0.003
Eye Irritation:	0.095
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC273798

Natural Product ID:	NPC273798
*Common Name:**	Garcinielliptone Fb
IUPAC Name:	n.a.
Synonyms:	Garcinielliptone Fb
Standard InCHIKey:	VFFHZZBYMYASGN-ITQIFJTGSA-N
Standard InCHI:	InChI=1S/C38H50O7/c1-21(2)11-12-24(23(5)6)17-26-20-37(16-15-22(3)4)33-27(19-30(45-33)36(9,10)44)32(42)38(34(37)43,35(26,7)8)31(41)25-13-14-28(39)29(40)18-25/h13-15,18,24,26,30,39-40,44H,1,5,11-12,16-17,19-20H2,2-4,6-10H3/t24-,26+,30+,37-,38+/m0/s1
SMILES:	C=C(C)CC[C@@H](C[C@@H]1C[C@@]2(CC=C(C)C)C3=C(C[C@H](C(C)(C)O)O3)C(=O)[C@](C(=O)c3ccc(c(c3)O)O)(C2=O)C1(C)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404741
PubChem CID:	11433532
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568764]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	pericarp	n.a.	n.a.	PMID[16038565]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18166016]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20232858]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	Database[Article]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6.8	ug.mL-1	PMID[548151]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	11.2	ug.mL-1	PMID[548151]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.3	ug.mL-1	PMID[548151]

☑ 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 NPC273798 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	347
0.1-0.2	1292
0.2-0.3	2514
0.3-0.4	6028
0.4-0.5	11468
0.5-0.6	6895
0.6-0.7	9871
0.7-0.8	4157
0.8-0.85	68
0.85-0.9	12
0.9-0.95	43
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9858	High Similarity	NPC132810
0.9441	High Similarity	NPC471970
0.931	High Similarity	NPC46549
0.931	High Similarity	NPC264229
0.9301	High Similarity	NPC469854
0.9301	High Similarity	NPC8493
0.9301	High Similarity	NPC469856
0.9301	High Similarity	NPC145301
0.9301	High Similarity	NPC294679
0.9301	High Similarity	NPC144247
0.9301	High Similarity	NPC469375
0.9296	High Similarity	NPC469855
0.9296	High Similarity	NPC471971
0.9296	High Similarity	NPC30846
0.9296	High Similarity	NPC471972
0.9281	High Similarity	NPC7464
0.922	High Similarity	NPC294330
0.9149	High Similarity	NPC157284
0.9149	High Similarity	NPC51531
0.9149	High Similarity	NPC289358
0.9149	High Similarity	NPC469857
0.9149	High Similarity	NPC23667
0.9149	High Similarity	NPC473779
0.9149	High Similarity	NPC165191
0.9149	High Similarity	NPC50615
0.9149	High Similarity	NPC46242
0.9149	High Similarity	NPC245760
0.9149	High Similarity	NPC42384
0.9149	High Similarity	NPC149773
0.9149	High Similarity	NPC477849
0.9149	High Similarity	NPC91887
0.9149	High Similarity	NPC473479
0.9149	High Similarity	NPC28592
0.9149	High Similarity	NPC5014
0.9149	High Similarity	NPC114333
0.9149	High Similarity	NPC297797
0.9021	High Similarity	NPC473527
0.9	High Similarity	NPC305710
0.8986	High Similarity	NPC237441
0.875	High Similarity	NPC471974
0.875	High Similarity	NPC469681
0.875	High Similarity	NPC469680
0.8636	High Similarity	NPC471968
0.8552	High Similarity	NPC118366
0.8511	High Similarity	NPC25736
0.8489	Intermediate Similarity	NPC294050
0.8489	Intermediate Similarity	NPC328997
0.8477	Intermediate Similarity	NPC476821
0.8425	Intermediate Similarity	NPC471152
0.8403	Intermediate Similarity	NPC138472
0.8403	Intermediate Similarity	NPC474715
0.8403	Intermediate Similarity	NPC4170
0.8389	Intermediate Similarity	NPC229218
0.8389	Intermediate Similarity	NPC176030
0.8389	Intermediate Similarity	NPC169214
0.8389	Intermediate Similarity	NPC192597
0.8389	Intermediate Similarity	NPC141817
0.8378	Intermediate Similarity	NPC470035
0.8369	Intermediate Similarity	NPC316553
0.8344	Intermediate Similarity	NPC470038
0.8333	Intermediate Similarity	NPC199936
0.8313	Intermediate Similarity	NPC100420
0.8312	Intermediate Similarity	NPC48949
0.8299	Intermediate Similarity	NPC119542
0.8299	Intermediate Similarity	NPC277559
0.8276	Intermediate Similarity	NPC111845
0.8267	Intermediate Similarity	NPC469447
0.8267	Intermediate Similarity	NPC248068
0.8267	Intermediate Similarity	NPC184935
0.8267	Intermediate Similarity	NPC477873
0.8255	Intermediate Similarity	NPC476534
0.8255	Intermediate Similarity	NPC471853
0.8243	Intermediate Similarity	NPC230811
0.8231	Intermediate Similarity	NPC38158
0.8224	Intermediate Similarity	NPC258856
0.8212	Intermediate Similarity	NPC239608
0.8212	Intermediate Similarity	NPC46161
0.8194	Intermediate Similarity	NPC117609
0.8194	Intermediate Similarity	NPC470037
0.8182	Intermediate Similarity	NPC234175
0.8176	Intermediate Similarity	NPC264022
0.8176	Intermediate Similarity	NPC49911
0.8171	Intermediate Similarity	NPC472803
0.8169	Intermediate Similarity	NPC146239
0.8163	Intermediate Similarity	NPC153088
0.8163	Intermediate Similarity	NPC43353
0.8158	Intermediate Similarity	NPC53520
0.8158	Intermediate Similarity	NPC309169
0.8158	Intermediate Similarity	NPC196941
0.8151	Intermediate Similarity	NPC294226
0.8151	Intermediate Similarity	NPC327410
0.8143	Intermediate Similarity	NPC139171
0.8141	Intermediate Similarity	NPC144283
0.8117	Intermediate Similarity	NPC52692
0.8108	Intermediate Similarity	NPC470733
0.8105	Intermediate Similarity	NPC225351
0.8105	Intermediate Similarity	NPC478160
0.8105	Intermediate Similarity	NPC73416
0.8105	Intermediate Similarity	NPC8102
0.8105	Intermediate Similarity	NPC66894
0.8105	Intermediate Similarity	NPC75295
0.8105	Intermediate Similarity	NPC160777
0.8098	Intermediate Similarity	NPC200726
0.8095	Intermediate Similarity	NPC202225
0.8092	Intermediate Similarity	NPC209085
0.8092	Intermediate Similarity	NPC25491
0.8092	Intermediate Similarity	NPC224884
0.8089	Intermediate Similarity	NPC164912
0.8082	Intermediate Similarity	NPC477407
0.8079	Intermediate Similarity	NPC472904
0.8079	Intermediate Similarity	NPC84273
0.8079	Intermediate Similarity	NPC472410
0.8077	Intermediate Similarity	NPC118033
0.8077	Intermediate Similarity	NPC475311
0.8077	Intermediate Similarity	NPC473680
0.8077	Intermediate Similarity	NPC473579
0.8077	Intermediate Similarity	NPC475454
0.8072	Intermediate Similarity	NPC471969
0.8065	Intermediate Similarity	NPC94781
0.805	Intermediate Similarity	NPC478223
0.8049	Intermediate Similarity	NPC177362
0.8041	Intermediate Similarity	NPC258502
0.8038	Intermediate Similarity	NPC25127
0.8038	Intermediate Similarity	NPC62051
0.8026	Intermediate Similarity	NPC11314
0.8025	Intermediate Similarity	NPC124842
0.8025	Intermediate Similarity	NPC118427
0.8025	Intermediate Similarity	NPC473773
0.8025	Intermediate Similarity	NPC221249
0.8025	Intermediate Similarity	NPC475579
0.8014	Intermediate Similarity	NPC86900
0.8013	Intermediate Similarity	NPC478219
0.8013	Intermediate Similarity	NPC327962
0.8013	Intermediate Similarity	NPC280753
0.8013	Intermediate Similarity	NPC78987
0.8013	Intermediate Similarity	NPC44378
0.8013	Intermediate Similarity	NPC27518
0.8013	Intermediate Similarity	NPC82336
0.8013	Intermediate Similarity	NPC304110
0.8013	Intermediate Similarity	NPC474310
0.8	Intermediate Similarity	NPC61398
0.8	Intermediate Similarity	NPC475757
0.8	Intermediate Similarity	NPC262819
0.8	Intermediate Similarity	NPC202428
0.8	Intermediate Similarity	NPC10842
0.8	Intermediate Similarity	NPC266545
0.8	Intermediate Similarity	NPC474640
0.8	Intermediate Similarity	NPC416
0.8	Intermediate Similarity	NPC470747
0.8	Intermediate Similarity	NPC98305
0.7988	Intermediate Similarity	NPC263212
0.7987	Intermediate Similarity	NPC30890
0.7987	Intermediate Similarity	NPC472807
0.7986	Intermediate Similarity	NPC72667
0.7975	Intermediate Similarity	NPC105942
0.7975	Intermediate Similarity	NPC476822
0.7975	Intermediate Similarity	NPC205392
0.7974	Intermediate Similarity	NPC469615
0.7974	Intermediate Similarity	NPC474692
0.7974	Intermediate Similarity	NPC46880
0.7974	Intermediate Similarity	NPC478164
0.7973	Intermediate Similarity	NPC194970
0.7963	Intermediate Similarity	NPC266365
0.7963	Intermediate Similarity	NPC477627
0.7959	Intermediate Similarity	NPC144257
0.7959	Intermediate Similarity	NPC50763
0.7959	Intermediate Similarity	NPC477406
0.7958	Intermediate Similarity	NPC325740
0.7949	Intermediate Similarity	NPC474903
0.7947	Intermediate Similarity	NPC472903
0.7947	Intermediate Similarity	NPC474784
0.7945	Intermediate Similarity	NPC108129
0.7939	Intermediate Similarity	NPC478059
0.7939	Intermediate Similarity	NPC471975
0.7939	Intermediate Similarity	NPC478060
0.7939	Intermediate Similarity	NPC470377
0.7939	Intermediate Similarity	NPC470374
0.7935	Intermediate Similarity	NPC136878
0.7935	Intermediate Similarity	NPC470330
0.7935	Intermediate Similarity	NPC477208
0.7933	Intermediate Similarity	NPC475957
0.7929	Intermediate Similarity	NPC469418
0.7927	Intermediate Similarity	NPC472277
0.7925	Intermediate Similarity	NPC475770
0.7925	Intermediate Similarity	NPC474000
0.7925	Intermediate Similarity	NPC287504
0.7922	Intermediate Similarity	NPC280717
0.7922	Intermediate Similarity	NPC271607
0.7922	Intermediate Similarity	NPC29932
0.7922	Intermediate Similarity	NPC469683
0.7922	Intermediate Similarity	NPC126707
0.7919	Intermediate Similarity	NPC89504
0.7919	Intermediate Similarity	NPC95485
0.7919	Intermediate Similarity	NPC88065
0.7917	Intermediate Similarity	NPC254492
0.7917	Intermediate Similarity	NPC15837
0.7917	Intermediate Similarity	NPC71610
0.7911	Intermediate Similarity	NPC151425
0.7911	Intermediate Similarity	NPC473201
0.7911	Intermediate Similarity	NPC302783

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 NPC273798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	845
0.2-0.3	1470
0.3-0.4	2664
0.4-0.5	2190
0.5-0.6	1194
0.6-0.7	448
0.7-0.8	44
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
0.8322	Intermediate Similarity	NPD8166	Discontinued
0.7676	Intermediate Similarity	NPD2932	Approved
0.76	Intermediate Similarity	NPD943	Approved
0.7593	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3019	Approved
0.7533	Intermediate Similarity	NPD6663	Approved
0.7532	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD5736	Approved
0.7471	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8434	Phase 2
0.7378	Intermediate Similarity	NPD2801	Approved
0.7365	Intermediate Similarity	NPD1470	Approved
0.7353	Intermediate Similarity	NPD7473	Discontinued
0.7347	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7458	Discontinued
0.7342	Intermediate Similarity	NPD6190	Approved
0.731	Intermediate Similarity	NPD3818	Discontinued
0.731	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7028	Phase 2
0.7296	Intermediate Similarity	NPD3300	Phase 2
0.729	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3972	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.7262	Intermediate Similarity	NPD5494	Approved
0.7255	Intermediate Similarity	NPD3620	Phase 2
0.7255	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7685	Pre-registration
0.7232	Intermediate Similarity	NPD8150	Discontinued
0.7219	Intermediate Similarity	NPD8127	Discontinued
0.7211	Intermediate Similarity	NPD1201	Approved
0.7208	Intermediate Similarity	NPD230	Phase 1
0.7197	Intermediate Similarity	NPD2344	Approved
0.7195	Intermediate Similarity	NPD4380	Phase 2
0.7193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6166	Phase 2
0.7186	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6232	Discontinued
0.717	Intermediate Similarity	NPD4110	Phase 3
0.717	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7819	Suspended
0.7153	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD3023	Approved
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3026	Approved
0.7143	Intermediate Similarity	NPD3021	Approved
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD1511	Approved
0.7126	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7074	Phase 3
0.7124	Intermediate Similarity	NPD3764	Approved
0.7123	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3025	Approved
0.7123	Intermediate Similarity	NPD3024	Approved
0.7095	Intermediate Similarity	NPD3092	Approved
0.7081	Intermediate Similarity	NPD7236	Approved
0.707	Intermediate Similarity	NPD2799	Discontinued
0.7069	Intermediate Similarity	NPD7054	Approved
0.7066	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1512	Approved
0.7055	Intermediate Similarity	NPD3091	Approved
0.703	Intermediate Similarity	NPD3455	Phase 2
0.7029	Intermediate Similarity	NPD7472	Approved
0.7025	Intermediate Similarity	NPD2935	Discontinued
0.702	Intermediate Similarity	NPD3094	Phase 2
0.7019	Intermediate Similarity	NPD2309	Approved
0.7	Intermediate Similarity	NPD6234	Discontinued
0.6988	Remote Similarity	NPD6599	Discontinued
0.6981	Remote Similarity	NPD2346	Discontinued
0.6978	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5844	Phase 1
0.6968	Remote Similarity	NPD8032	Phase 2
0.6966	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5761	Phase 2
0.6964	Remote Similarity	NPD5760	Phase 2
0.6962	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1510	Phase 2
0.6957	Remote Similarity	NPD7003	Approved
0.6954	Remote Similarity	NPD1876	Approved
0.6949	Remote Similarity	NPD7251	Discontinued
0.6948	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1549	Phase 2
0.6933	Remote Similarity	NPD7390	Discontinued
0.6933	Remote Similarity	NPD9269	Phase 2
0.6923	Remote Similarity	NPD3817	Phase 2
0.6918	Remote Similarity	NPD5406	Approved
0.6918	Remote Similarity	NPD6100	Approved
0.6918	Remote Similarity	NPD5405	Approved
0.6918	Remote Similarity	NPD6099	Approved
0.6918	Remote Similarity	NPD5408	Approved
0.6918	Remote Similarity	NPD5404	Approved
0.6914	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7808	Phase 3
0.6897	Remote Similarity	NPD2629	Approved
0.6894	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2800	Approved
0.6893	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6797	Phase 2
0.689	Remote Similarity	NPD2533	Approved
0.689	Remote Similarity	NPD2534	Approved
0.689	Remote Similarity	NPD2532	Approved
0.689	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6355	Discontinued
0.6875	Remote Similarity	NPD7266	Discontinued
0.6875	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1471	Phase 3
0.6875	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8313	Approved
0.6872	Remote Similarity	NPD8312	Approved
0.6871	Remote Similarity	NPD5536	Phase 2
0.6867	Remote Similarity	NPD7239	Suspended
0.6863	Remote Similarity	NPD2798	Approved
0.6853	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3095	Discontinued
0.6842	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7095	Approved
0.6835	Remote Similarity	NPD1607	Approved
0.6835	Remote Similarity	NPD6651	Approved
0.6832	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3226	Approved
0.6824	Remote Similarity	NPD5977	Approved
0.6824	Remote Similarity	NPD9545	Approved
0.6824	Remote Similarity	NPD5978	Approved
0.6821	Remote Similarity	NPD6959	Discontinued
0.6818	Remote Similarity	NPD7228	Approved
0.6816	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1240	Approved
0.6813	Remote Similarity	NPD2796	Approved
0.6807	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD37	Approved
0.6805	Remote Similarity	NPD6801	Discontinued
0.6788	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4967	Phase 2
0.6784	Remote Similarity	NPD4965	Approved
0.6784	Remote Similarity	NPD4966	Approved
0.678	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD447	Suspended
0.6772	Remote Similarity	NPD5735	Approved
0.6765	Remote Similarity	NPD1465	Phase 2
0.676	Remote Similarity	NPD6559	Discontinued
0.676	Remote Similarity	NPD8368	Discontinued
0.6752	Remote Similarity	NPD7961	Discontinued
0.6746	Remote Similarity	NPD6873	Phase 2
0.6743	Remote Similarity	NPD3926	Phase 2
0.674	Remote Similarity	NPD8407	Phase 2
0.6733	Remote Similarity	NPD4059	Approved
0.6732	Remote Similarity	NPD1283	Approved
0.6727	Remote Similarity	NPD6799	Approved
0.6726	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7799	Discontinued
0.6722	Remote Similarity	NPD4954	Approved
0.6722	Remote Similarity	NPD4955	Approved
0.6722	Remote Similarity	NPD5026	Approved
0.6722	Remote Similarity	NPD5028	Approved
0.6722	Remote Similarity	NPD5034	Approved
0.6722	Remote Similarity	NPD36	Approved
0.6713	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD826	Approved
0.6709	Remote Similarity	NPD4140	Approved
0.6709	Remote Similarity	NPD4060	Phase 1
0.6709	Remote Similarity	NPD825	Approved
0.6708	Remote Similarity	NPD2438	Suspended
0.6689	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1164	Approved
0.6688	Remote Similarity	NPD2313	Discontinued
0.6687	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD5030	Phase 2
0.6667	Remote Similarity	NPD5951	Approved
0.6667	Remote Similarity	NPD7907	Approved
0.6667	Remote Similarity	NPD9268	Approved
0.6667	Remote Similarity	NPD5327	Phase 3
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD6765	Approved
0.6649	Remote Similarity	NPD2488	Approved
0.6649	Remote Similarity	NPD2490	Approved
0.6649	Remote Similarity	NPD2491	Approved
0.6647	Remote Similarity	NPD6386	Approved
0.6647	Remote Similarity	NPD7411	Suspended
0.6647	Remote Similarity	NPD6385	Approved
0.6647	Remote Similarity	NPD3749	Approved
0.6646	Remote Similarity	NPD3750	Approved
0.6645	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5647	Approved
0.6644	Remote Similarity	NPD7610	Discontinued
0.6632	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3751	Discontinued
0.6625	Remote Similarity	NPD6353	Approved
0.6624	Remote Similarity	NPD3027	Phase 3
0.6614	Remote Similarity	NPD7700	Phase 2

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