NPASS Compound

Structure

CID230538 OpenBabel06191716022D 30 33 0 0 1 0 0 0 0 0999 V2000 4.5002 2.7720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6771 1.5950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1393 -3.6415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7822 -2.8250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8967 -2.5372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3679 -2.0084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1965 1.9009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7132 1.7056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6108 -1.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5542 0.7628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1393 1.9009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8060 1.2342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5298 1.2342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1393 -0.3753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1393 -2.0084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8967 1.2342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5298 0.2914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1965 -0.3753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8060 0.2914 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1965 -2.0084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8967 0.2914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7132 -0.1801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7251 -1.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6771 -0.0695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6108 -2.8250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7251 -2.8250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7132 -2.0658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8393 -1.1919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.5256 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 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 29 1 0 0 0 0 10 30 1 0 0 0 0 11 1 1 6 0 0 0 11 12 1 0 0 0 0 12 2 1 6 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 25 1 0 0 0 0 16 21 2 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 23 2 0 0 0 0 19 24 1 1 0 0 0 20 23 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.18
Volume:	417.851
LogP:	3.242
LogD:	3.28
LogS:	-4.389
# Rotatable Bonds:	4
TPSA:	75.61
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.808
Synthetic Accessibility Score:	3.754
Fsp3:	0.478
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:	-4.745
MDCK Permeability:	3.3242686185985804e-05
Pgp-inhibitor:	0.609
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	79.12709045410156%
Volume Distribution (VD):	0.877
Pgp-substrate:	10.756048202514648%

ADMET: Metabolism

CYP1A2-inhibitor:	0.143
CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	0.77
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.889
CYP3A4-substrate:	0.831

ADMET: Excretion

Clearance (CL):	6.231
Half-life (T1/2):	0.115

ADMET: Toxicity

hERG Blockers:	0.277
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.417
AMES Toxicity:	0.109
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.384
Carcinogencity:	0.661
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.493

Download Data

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

Natural Product: NPC230538

Natural Product ID:	NPC230538
*Common Name:**	Gomisin O
IUPAC Name:	n.a.
Synonyms:	Gomisin O
Standard InCHIKey:	GWDFJIBHVSYXQL-SYTFOFBDSA-N
Standard InCHI:	InChI=1S/C23H28O7/c1-11-7-13-8-16-21(30-10-29-16)22(27-5)17(13)18-14(19(24)12(11)2)9-15(25-3)20(26-4)23(18)28-6/h8-9,11-12,19,24H,7,10H2,1-6H3/t11-,12-,19+/m0/s1
SMILES:	COc1cc2[C@H](O)[C@@H](C)[C@@H](C)Cc3c(c2c(c1OC)OC)c(OC)c1c(c3)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522973
PubChem CID:	5317808
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1002/cjoc.20010190319]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/j.tet.2008.10.079]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11395273]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16494492]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17489633]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[18536373]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	aerial parts	Erlang Mountain area of Sichuan Province, China	2007-SEP	PMID[19413342]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[20146529]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20681569]
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota	Stems	Luoji Mountain Village, Xichang County, Sicuan Province, China	2011-Sep	PMID[23738539]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11167	Prunus ssiori	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9834	Veronica austriaca	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6903	Lecanora straminea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7128	Cynthia savignyi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7374	Seseli montanum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7850	Schisandra propinqua	Species	Schisandraceae	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
EC50	1
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	>	60000.0	nM	PMID[530552]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	36000.0	nM	PMID[530552]
NPT27	Others	Unspecified		Ratio IC50/EC50	=	1.7	n.a.	PMID[530552]

☑ 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 NPC230538 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	395
0.1-0.2	1504
0.2-0.3	3961
0.3-0.4	10493
0.4-0.5	8361
0.5-0.6	4292
0.6-0.7	8425
0.7-0.8	3833
0.8-0.85	1021
0.85-0.9	321
0.9-0.95	68
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC103637
1.0	High Similarity	NPC36531
1.0	High Similarity	NPC229172
0.9926	High Similarity	NPC324962
0.9853	High Similarity	NPC239254
0.9853	High Similarity	NPC172171
0.9781	High Similarity	NPC475868
0.9781	High Similarity	NPC110763
0.9781	High Similarity	NPC189239
0.9781	High Similarity	NPC166506
0.9781	High Similarity	NPC197352
0.9708	High Similarity	NPC73467
0.9708	High Similarity	NPC121661
0.963	High Similarity	NPC290714
0.963	High Similarity	NPC201404
0.963	High Similarity	NPC53722
0.9571	High Similarity	NPC316676
0.9571	High Similarity	NPC325720
0.9568	High Similarity	NPC154971
0.9568	High Similarity	NPC252286
0.9562	High Similarity	NPC184641
0.9562	High Similarity	NPC184684
0.9562	High Similarity	NPC133934
0.9478	High Similarity	NPC185680
0.9478	High Similarity	NPC145722
0.9478	High Similarity	NPC256776
0.9437	High Similarity	NPC473989
0.9338	High Similarity	NPC32189
0.927	High Similarity	NPC86605
0.927	High Similarity	NPC301765
0.927	High Similarity	NPC3072
0.927	High Similarity	NPC156948
0.927	High Similarity	NPC474039
0.927	High Similarity	NPC46277
0.9259	High Similarity	NPC196937
0.9259	High Similarity	NPC58585
0.9241	High Similarity	NPC24562
0.9236	High Similarity	NPC475756
0.9214	High Similarity	NPC474808
0.9214	High Similarity	NPC218510
0.9214	High Similarity	NPC76415
0.9197	High Similarity	NPC197166
0.9197	High Similarity	NPC133025
0.9178	High Similarity	NPC473425
0.9178	High Similarity	NPC312763
0.9172	High Similarity	NPC471154
0.9161	High Similarity	NPC304821
0.9149	High Similarity	NPC326144
0.9137	High Similarity	NPC216434
0.9137	High Similarity	NPC103448
0.9124	High Similarity	NPC150534
0.9118	High Similarity	NPC112237
0.911	High Similarity	NPC474606
0.9103	High Similarity	NPC224472
0.9085	High Similarity	NPC327651
0.9085	High Similarity	NPC318286
0.9065	High Similarity	NPC30951
0.9065	High Similarity	NPC471183
0.9065	High Similarity	NPC6369
0.9065	High Similarity	NPC9068
0.9054	High Similarity	NPC473323
0.9051	High Similarity	NPC276026
0.9051	High Similarity	NPC555
0.9051	High Similarity	NPC206737
0.9051	High Similarity	NPC289258
0.9051	High Similarity	NPC469659
0.9051	High Similarity	NPC188378
0.9051	High Similarity	NPC7515
0.9051	High Similarity	NPC56764
0.9044	High Similarity	NPC102256
0.9021	High Similarity	NPC321958
0.9021	High Similarity	NPC321696
0.9007	High Similarity	NPC474295
0.9007	High Similarity	NPC41782
0.9007	High Similarity	NPC191231
0.9	High Similarity	NPC177868
0.9	High Similarity	NPC284464
0.9	High Similarity	NPC46591
0.8993	High Similarity	NPC185908
0.8993	High Similarity	NPC283949
0.8993	High Similarity	NPC196420
0.8986	High Similarity	NPC238834
0.8986	High Similarity	NPC55239
0.8986	High Similarity	NPC236522
0.8986	High Similarity	NPC214853
0.8986	High Similarity	NPC476065
0.8986	High Similarity	NPC240279
0.8986	High Similarity	NPC180602
0.898	High Similarity	NPC53669
0.898	High Similarity	NPC16791
0.898	High Similarity	NPC308739
0.898	High Similarity	NPC217708
0.898	High Similarity	NPC126405
0.898	High Similarity	NPC297271
0.898	High Similarity	NPC77237
0.8971	High Similarity	NPC141493
0.8971	High Similarity	NPC184928
0.8958	High Similarity	NPC116019
0.8951	High Similarity	NPC180953
0.8921	High Similarity	NPC172818
0.8921	High Similarity	NPC25695
0.8919	High Similarity	NPC198461
0.8905	High Similarity	NPC219671
0.8905	High Similarity	NPC65183
0.8905	High Similarity	NPC72046
0.8905	High Similarity	NPC97316
0.8905	High Similarity	NPC259742
0.8905	High Similarity	NPC104077
0.8905	High Similarity	NPC261812
0.8905	High Similarity	NPC147616
0.8905	High Similarity	NPC475856
0.8897	High Similarity	NPC198129
0.8897	High Similarity	NPC252281
0.8897	High Similarity	NPC477375
0.8897	High Similarity	NPC184814
0.8897	High Similarity	NPC63574
0.8897	High Similarity	NPC327352
0.8889	High Similarity	NPC474054
0.8889	High Similarity	NPC283114
0.8889	High Similarity	NPC33832
0.8889	High Similarity	NPC207702
0.8889	High Similarity	NPC149008
0.8881	High Similarity	NPC87883
0.8881	High Similarity	NPC473046
0.8881	High Similarity	NPC118385
0.8881	High Similarity	NPC472713
0.8881	High Similarity	NPC473960
0.8881	High Similarity	NPC472712
0.8881	High Similarity	NPC187774
0.8873	High Similarity	NPC287124
0.8867	High Similarity	NPC475592
0.8865	High Similarity	NPC226547
0.8865	High Similarity	NPC56091
0.8857	High Similarity	NPC477938
0.8841	High Similarity	NPC471390
0.8841	High Similarity	NPC266848
0.8841	High Similarity	NPC136750
0.8841	High Similarity	NPC471391
0.8836	High Similarity	NPC85141
0.8836	High Similarity	NPC477376
0.8836	High Similarity	NPC322426
0.8836	High Similarity	NPC477374
0.8819	High Similarity	NPC307466
0.8815	High Similarity	NPC242032
0.8811	High Similarity	NPC298317
0.8811	High Similarity	NPC185071
0.8811	High Similarity	NPC469630
0.8811	High Similarity	NPC12728
0.8811	High Similarity	NPC255566
0.8811	High Similarity	NPC265154
0.8808	High Similarity	NPC230531
0.8808	High Similarity	NPC215400
0.88	High Similarity	NPC29727
0.8794	High Similarity	NPC292487
0.8777	High Similarity	NPC326095
0.8777	High Similarity	NPC244983
0.8777	High Similarity	NPC287745
0.8777	High Similarity	NPC31530
0.8776	High Similarity	NPC182368
0.8776	High Similarity	NPC218041
0.8776	High Similarity	NPC472710
0.8776	High Similarity	NPC469707
0.8776	High Similarity	NPC24425
0.8776	High Similarity	NPC214326
0.8776	High Similarity	NPC225815
0.8776	High Similarity	NPC472709
0.8776	High Similarity	NPC185955
0.8776	High Similarity	NPC145979
0.8776	High Similarity	NPC9933
0.8776	High Similarity	NPC469706
0.8776	High Similarity	NPC260781
0.8776	High Similarity	NPC316989
0.8768	High Similarity	NPC175067
0.8768	High Similarity	NPC106739
0.8768	High Similarity	NPC7744
0.8768	High Similarity	NPC471505
0.8768	High Similarity	NPC204215
0.8767	High Similarity	NPC477879
0.8767	High Similarity	NPC270751
0.8767	High Similarity	NPC71726
0.8759	High Similarity	NPC99515
0.8759	High Similarity	NPC190714
0.8759	High Similarity	NPC212890
0.875	High Similarity	NPC166884
0.875	High Similarity	NPC477701
0.875	High Similarity	NPC63061
0.875	High Similarity	NPC141569
0.8741	High Similarity	NPC472714
0.8741	High Similarity	NPC470917
0.8741	High Similarity	NPC5262
0.8732	High Similarity	NPC109240
0.8725	High Similarity	NPC245948
0.8723	High Similarity	NPC865
0.8716	High Similarity	NPC303519
0.8714	High Similarity	NPC256262
0.8714	High Similarity	NPC101624
0.8714	High Similarity	NPC184938
0.8714	High Similarity	NPC18576
0.8714	High Similarity	NPC189474
0.8714	High Similarity	NPC49235

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 NPC230538 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	910
0.2-0.3	1885
0.3-0.4	2817
0.4-0.5	1627
0.5-0.6	932
0.6-0.7	556
0.7-0.8	92
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8725	High Similarity	NPD37	Approved
0.8553	High Similarity	NPD4965	Approved
0.8553	High Similarity	NPD4966	Approved
0.8553	High Similarity	NPD4967	Phase 2
0.8551	High Similarity	NPD3027	Phase 3
0.837	Intermediate Similarity	NPD3705	Approved
0.8323	Intermediate Similarity	NPD6234	Discontinued
0.8112	Intermediate Similarity	NPD1613	Approved
0.8112	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7199	Phase 2
0.8075	Intermediate Similarity	NPD7228	Approved
0.8041	Intermediate Similarity	NPD6674	Discontinued
0.7888	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1357	Approved
0.7832	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7240	Approved
0.7762	Intermediate Similarity	NPD3018	Phase 2
0.7708	Intermediate Similarity	NPD4908	Phase 1
0.7704	Intermediate Similarity	NPD5283	Phase 1
0.7692	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD3818	Discontinued
0.7628	Intermediate Similarity	NPD1653	Approved
0.7619	Intermediate Similarity	NPD3620	Phase 2
0.7619	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2982	Phase 2
0.7606	Intermediate Similarity	NPD2983	Phase 2
0.7603	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1091	Approved
0.7589	Intermediate Similarity	NPD1610	Phase 2
0.7535	Intermediate Similarity	NPD2981	Phase 2
0.7534	Intermediate Similarity	NPD4625	Phase 3
0.7517	Intermediate Similarity	NPD2861	Phase 2
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7484	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4005	Discontinued
0.7452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7074	Phase 3
0.7394	Intermediate Similarity	NPD6232	Discontinued
0.7383	Intermediate Similarity	NPD4060	Phase 1
0.7381	Intermediate Similarity	NPD7054	Approved
0.7365	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7473	Discontinued
0.7361	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4749	Approved
0.7338	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7472	Approved
0.7329	Intermediate Similarity	NPD1934	Approved
0.7326	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7266	Discontinued
0.7305	Intermediate Similarity	NPD1548	Phase 1
0.729	Intermediate Similarity	NPD3892	Phase 2
0.7284	Intermediate Similarity	NPD2978	Approved
0.7284	Intermediate Similarity	NPD2977	Approved
0.7278	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2238	Phase 2
0.7251	Intermediate Similarity	NPD6559	Discontinued
0.7244	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5177	Phase 3
0.7222	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7808	Phase 3
0.7208	Intermediate Similarity	NPD5762	Approved
0.7208	Intermediate Similarity	NPD3540	Phase 1
0.7208	Intermediate Similarity	NPD5763	Approved
0.7203	Intermediate Similarity	NPD5125	Phase 3
0.7203	Intermediate Similarity	NPD5126	Approved
0.7197	Intermediate Similarity	NPD5058	Phase 3
0.7195	Intermediate Similarity	NPD3882	Suspended
0.7195	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6797	Phase 2
0.719	Intermediate Similarity	NPD4108	Discontinued
0.7186	Intermediate Similarity	NPD3787	Discontinued
0.7178	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD228	Approved
0.7169	Intermediate Similarity	NPD5494	Approved
0.7152	Intermediate Similarity	NPD4055	Discovery
0.7152	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7251	Discontinued
0.7143	Intermediate Similarity	NPD3539	Phase 1
0.7143	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2560	Approved
0.7134	Intermediate Similarity	NPD2563	Approved
0.7133	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4236	Phase 3
0.7115	Intermediate Similarity	NPD4237	Approved
0.711	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3657	Discovery
0.7102	Intermediate Similarity	NPD6842	Approved
0.7102	Intermediate Similarity	NPD6841	Approved
0.7102	Intermediate Similarity	NPD6843	Phase 3
0.7101	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6166	Phase 2
0.7101	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1375	Discontinued
0.7092	Intermediate Similarity	NPD709	Approved
0.7089	Intermediate Similarity	NPD7124	Phase 2
0.7086	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7229	Phase 3
0.7073	Intermediate Similarity	NPD2801	Approved
0.7073	Intermediate Similarity	NPD1465	Phase 2
0.7065	Intermediate Similarity	NPD7680	Approved
0.7051	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4357	Discontinued
0.703	Intermediate Similarity	NPD3817	Phase 2
0.7029	Intermediate Similarity	NPD4750	Phase 3
0.7029	Intermediate Similarity	NPD3022	Approved
0.7029	Intermediate Similarity	NPD3021	Approved
0.7025	Intermediate Similarity	NPD2677	Approved
0.702	Intermediate Similarity	NPD5110	Phase 2
0.702	Intermediate Similarity	NPD5109	Approved
0.702	Intermediate Similarity	NPD5111	Phase 2
0.7018	Intermediate Similarity	NPD3751	Discontinued
0.7013	Intermediate Similarity	NPD6111	Discontinued
0.7007	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3060	Approved
0.7	Intermediate Similarity	NPD2533	Approved
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD2532	Approved
0.6994	Remote Similarity	NPD4675	Approved
0.6994	Remote Similarity	NPD7028	Phase 2
0.6994	Remote Similarity	NPD4678	Approved
0.6993	Remote Similarity	NPD5124	Phase 1
0.6993	Remote Similarity	NPD5735	Approved
0.6993	Remote Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8455	Phase 2
0.6966	Remote Similarity	NPD4626	Approved
0.6962	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4110	Phase 3
0.6959	Remote Similarity	NPD6696	Suspended
0.6951	Remote Similarity	NPD5089	Approved
0.6951	Remote Similarity	NPD5090	Approved
0.6948	Remote Similarity	NPD4097	Suspended
0.6941	Remote Similarity	NPD2970	Approved
0.6941	Remote Similarity	NPD2969	Approved
0.6928	Remote Similarity	NPD4140	Approved
0.6923	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD6099	Approved
0.6918	Remote Similarity	NPD2219	Phase 1
0.6918	Remote Similarity	NPD5241	Discontinued
0.6914	Remote Similarity	NPD7549	Discontinued
0.6913	Remote Similarity	NPD3094	Phase 2
0.6909	Remote Similarity	NPD3383	Approved
0.6909	Remote Similarity	NPD3384	Approved
0.6909	Remote Similarity	NPD3382	Approved
0.6899	Remote Similarity	NPD1652	Phase 2
0.689	Remote Similarity	NPD4380	Phase 2
0.6882	Remote Similarity	NPD6071	Discontinued
0.6882	Remote Similarity	NPD3051	Approved
0.6879	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5536	Phase 2
0.6871	Remote Similarity	NPD422	Phase 1
0.6867	Remote Similarity	NPD7819	Suspended
0.6867	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5588	Approved
0.6857	Remote Similarity	NPD7685	Pre-registration
0.6855	Remote Similarity	NPD3750	Approved
0.6855	Remote Similarity	NPD6331	Phase 2
0.6853	Remote Similarity	NPD7157	Approved
0.6852	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1283	Approved
0.6846	Remote Similarity	NPD8651	Approved
0.6835	Remote Similarity	NPD2684	Approved
0.6832	Remote Similarity	NPD1511	Approved
0.6824	Remote Similarity	NPD8127	Discontinued
0.6824	Remote Similarity	NPD2230	Approved
0.6824	Remote Similarity	NPD2233	Approved
0.6824	Remote Similarity	NPD6959	Discontinued
0.6824	Remote Similarity	NPD2232	Approved
0.6815	Remote Similarity	NPD2438	Suspended
0.6802	Remote Similarity	NPD2489	Approved
0.6802	Remote Similarity	NPD27	Approved
0.68	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4536	Approved
0.6795	Remote Similarity	NPD4538	Approved
0.6781	Remote Similarity	NPD5691	Approved
0.6779	Remote Similarity	NPD5327	Phase 3
0.6778	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6002	Phase 3
0.6772	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6004	Phase 3
0.6772	Remote Similarity	NPD6005	Phase 3
0.6772	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD846	Approved
0.6765	Remote Similarity	NPD940	Approved
0.6763	Remote Similarity	NPD290	Approved
0.6761	Remote Similarity	NPD7843	Approved
0.676	Remote Similarity	NPD4663	Approved
0.6757	Remote Similarity	NPD3092	Approved
0.6755	Remote Similarity	NPD4624	Approved
0.6752	Remote Similarity	NPD1510	Phase 2
0.6752	Remote Similarity	NPD7033	Discontinued
0.6752	Remote Similarity	NPD6029	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data