NPASS Compound

Structure

NPC289167 OpenBabel07101719152D 36 42 0 0 1 0 0 0 0 0999 V2000 3.6808 3.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8903 2.0932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0714 0.3706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6646 -0.5430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9013 1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4898 -0.8854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2852 -1.7689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9067 1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1807 -2.7635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8717 -0.8854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7634 -2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4836 1.1796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6808 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2634 -1.5610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 2.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4890 1.0751 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6808 0.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6701 -0.6475 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0878 0.0570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -2.0823 0.1615 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.6810 -0.8565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1808 -1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0942 -3.1702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 3 5 1 0 0 0 0 3 20 1 0 0 0 0 4 6 1 0 0 0 0 4 21 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 11 1 0 0 0 0 7 24 1 0 0 0 0 8 12 1 0 0 0 0 8 25 1 0 0 0 0 9 13 2 0 0 0 0 9 22 1 0 0 0 0 10 14 2 0 0 0 0 10 23 1 0 0 0 0 13 34 1 0 0 0 0 14 35 1 0 0 0 0 15 22 2 0 0 0 0 15 34 1 0 0 0 0 16 23 2 0 0 0 0 16 35 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 18 31 1 0 0 0 0 19 29 1 0 0 0 0 19 36 1 0 0 0 0 20 1 1 6 0 0 0 20 24 1 0 0 0 0 21 2 1 1 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 31 1 1 0 0 0 25 32 1 6 0 0 0 26 31 1 1 0 0 0 27 32 1 6 0 0 0 28 30 1 1 0 0 0 28 32 1 0 0 0 0 28 33 1 0 0 0 0 29 11 1 6 0 0 0 30 12 1 1 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.29
Volume:	523.868
LogP:	5.154
LogD:	4.592
LogS:	-4.009
# Rotatable Bonds:	2
TPSA:	52.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.49
Synthetic Accessibility Score:	6.243
Fsp3:	0.733
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.601
MDCK Permeability:	8.115906894090585e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.892
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	97.10108184814453%
Volume Distribution (VD):	1.198
Pgp-substrate:	2.4923558235168457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.99
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	11.895
Half-life (T1/2):	0.024

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.22
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.037
Carcinogencity:	0.942
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC289167

Natural Product ID:	NPC289167
*Common Name:**	GAKRXIIHJWAJNM-PPHJCHBXSA-N
IUPAC Name:	n.a.
Synonyms:	6-Hydroxythiobinupharidine
Standard InCHIKey:	GAKRXIIHJWAJNM-PPHJCHBXSA-N
Standard InCHI:	InChI=1S/C30H42N2O3S/c1-20-3-5-26(22-9-13-34-15-22)31-18-29(11-7-24(20)31)17-30(36-19-29)12-8-25-21(2)4-6-27(32(25)28(30)33)23-10-14-35-16-23/h9-10,13-16,20-21,24-28,33H,3-8,11-12,17-19H2,1-2H3/t20-,21-,24+,25+,26+,27+,28-,29+,30+/m1/s1
SMILES:	C[C@@H]1CC[C@H](N2[C@H]1CC[C@]1(C2)CS[C@]2(C1)CC[C@@H]1N([C@@H]2O)[C@@H](CC[C@H]1C)c1cocc1)c1cocc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL138270
PubChem CID:	9936153
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000222] Quinolizines

*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
NPO33085	nuphar pumilum	Species	Nymphaeaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[14643343]
NPO33085	nuphar pumilum	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16413779]

☑ 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
Others	28

Activity Type	# Activity
Cell Line	28

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	50.9	%	PMID[476566]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	57.5	%	PMID[476566]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	66.5	%	PMID[476566]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	84.8	%	PMID[476566]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	86.8	%	PMID[476566]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	94.0	%	PMID[476566]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	3.6	%	PMID[476567]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	83.2	%	PMID[476567]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	1.3	%	PMID[476567]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	92.5	%	PMID[476567]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	-1.0	%	PMID[476567]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	94.3	%	PMID[476567]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	88.6	%	PMID[476567]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	10.3	%	PMID[476567]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	27.3	%	PMID[476567]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	97.3	%	PMID[476567]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	11.1	%	PMID[476567]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	20.8	%	PMID[476567]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	98.7	%	PMID[476567]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	1.8	%	PMID[476567]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	14.0	%	PMID[476567]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	96.1	%	PMID[476567]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	1.6	%	PMID[476567]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	8.3	%	PMID[476567]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	97.5	%	PMID[476567]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	5.4	%	PMID[476567]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	15.7	%	PMID[476567]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	99.2	%	PMID[476567]

☑ 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 NPC289167 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	271
0.1-0.2	1354
0.2-0.3	4502
0.3-0.4	14302
0.4-0.5	17052
0.5-0.6	4941
0.6-0.7	260
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	3
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC76433
1.0	High Similarity	NPC186957
0.9879	High Similarity	NPC297647
0.9571	High Similarity	NPC176304
0.9571	High Similarity	NPC473245
0.9571	High Similarity	NPC70840
0.9398	High Similarity	NPC472474
0.9398	High Similarity	NPC469964
0.9398	High Similarity	NPC476236
0.7917	Intermediate Similarity	NPC223873
0.7914	Intermediate Similarity	NPC208170
0.7914	Intermediate Similarity	NPC216149
0.756	Intermediate Similarity	NPC473444
0.756	Intermediate Similarity	NPC26589
0.6845	Remote Similarity	NPC471651
0.6685	Remote Similarity	NPC471649
0.6587	Remote Similarity	NPC477967
0.6524	Remote Similarity	NPC133817
0.6524	Remote Similarity	NPC476443
0.6433	Remote Similarity	NPC23086
0.6432	Remote Similarity	NPC128683
0.6429	Remote Similarity	NPC471647
0.6429	Remote Similarity	NPC471646
0.6386	Remote Similarity	NPC144745
0.6386	Remote Similarity	NPC208906
0.6364	Remote Similarity	NPC28054
0.6343	Remote Similarity	NPC89133
0.6337	Remote Similarity	NPC46536
0.6337	Remote Similarity	NPC471650
0.6337	Remote Similarity	NPC138139
0.6316	Remote Similarity	NPC477965
0.6316	Remote Similarity	NPC477038
0.6301	Remote Similarity	NPC83178
0.6294	Remote Similarity	NPC317217
0.6286	Remote Similarity	NPC473005
0.6286	Remote Similarity	NPC243483
0.6286	Remote Similarity	NPC67346
0.6286	Remote Similarity	NPC476925
0.6286	Remote Similarity	NPC43069
0.6286	Remote Similarity	NPC97086
0.6286	Remote Similarity	NPC232533
0.6286	Remote Similarity	NPC140577
0.6281	Remote Similarity	NPC327005
0.6279	Remote Similarity	NPC303010
0.6264	Remote Similarity	NPC327527
0.6264	Remote Similarity	NPC477040
0.6264	Remote Similarity	NPC207294
0.6264	Remote Similarity	NPC477966
0.6264	Remote Similarity	NPC112706
0.6264	Remote Similarity	NPC476917
0.6264	Remote Similarity	NPC477123
0.6264	Remote Similarity	NPC477039
0.625	Remote Similarity	NPC189908
0.625	Remote Similarity	NPC243704
0.625	Remote Similarity	NPC61788
0.6244	Remote Similarity	NPC478075
0.6243	Remote Similarity	NPC74612
0.6239	Remote Similarity	NPC38964
0.6238	Remote Similarity	NPC149571
0.6225	Remote Similarity	NPC45389
0.6221	Remote Similarity	NPC243269
0.6215	Remote Similarity	NPC473982
0.6207	Remote Similarity	NPC4910
0.6207	Remote Similarity	NPC329731
0.6201	Remote Similarity	NPC476947
0.6199	Remote Similarity	NPC471549
0.6199	Remote Similarity	NPC473379
0.618	Remote Similarity	NPC471006
0.618	Remote Similarity	NPC218838
0.6179	Remote Similarity	NPC41216
0.6173	Remote Similarity	NPC471648
0.6169	Remote Similarity	NPC27887
0.6168	Remote Similarity	NPC150895
0.6163	Remote Similarity	NPC16922
0.6163	Remote Similarity	NPC272899
0.6154	Remote Similarity	NPC90953
0.6154	Remote Similarity	NPC477258
0.6154	Remote Similarity	NPC174783
0.615	Remote Similarity	NPC222524
0.6149	Remote Similarity	NPC329922
0.6149	Remote Similarity	NPC81912
0.6149	Remote Similarity	NPC329694
0.6149	Remote Similarity	NPC474260
0.6124	Remote Similarity	NPC24228
0.6117	Remote Similarity	NPC477526
0.6117	Remote Similarity	NPC471007
0.6114	Remote Similarity	NPC476016
0.6114	Remote Similarity	NPC474830
0.6109	Remote Similarity	NPC82056
0.6108	Remote Similarity	NPC473007
0.6106	Remote Similarity	NPC59827
0.6106	Remote Similarity	NPC184933
0.6098	Remote Similarity	NPC177331
0.6098	Remote Similarity	NPC477259
0.6098	Remote Similarity	NPC169387
0.6098	Remote Similarity	NPC230098
0.6093	Remote Similarity	NPC157958
0.6092	Remote Similarity	NPC71274
0.6092	Remote Similarity	NPC75557
0.6092	Remote Similarity	NPC474829
0.6092	Remote Similarity	NPC179354
0.6089	Remote Similarity	NPC266425
0.6087	Remote Similarity	NPC205765
0.6087	Remote Similarity	NPC473004
0.6087	Remote Similarity	NPC226708
0.608	Remote Similarity	NPC474438
0.608	Remote Similarity	NPC474279
0.6073	Remote Similarity	NPC473006
0.6067	Remote Similarity	NPC298190
0.6067	Remote Similarity	NPC17681
0.6064	Remote Similarity	NPC214239
0.6064	Remote Similarity	NPC476938
0.6064	Remote Similarity	NPC250228
0.6064	Remote Similarity	NPC476937
0.6062	Remote Similarity	NPC476436
0.6053	Remote Similarity	NPC196846
0.6047	Remote Similarity	NPC126211
0.6047	Remote Similarity	NPC476500
0.6045	Remote Similarity	NPC120836
0.6045	Remote Similarity	NPC223063
0.6044	Remote Similarity	NPC471316
0.6043	Remote Similarity	NPC75179
0.6043	Remote Similarity	NPC185456
0.6038	Remote Similarity	NPC268170
0.6034	Remote Similarity	NPC118853
0.6034	Remote Similarity	NPC130275
0.6034	Remote Similarity	NPC97740
0.6034	Remote Similarity	NPC45358
0.6033	Remote Similarity	NPC67003
0.6032	Remote Similarity	NPC476942
0.6032	Remote Similarity	NPC476941
0.6029	Remote Similarity	NPC102760
0.6023	Remote Similarity	NPC290955
0.6023	Remote Similarity	NPC473969
0.6022	Remote Similarity	NPC158525
0.6019	Remote Similarity	NPC100863
0.6019	Remote Similarity	NPC477527
0.6019	Remote Similarity	NPC112937
0.6012	Remote Similarity	NPC263870
0.6011	Remote Similarity	NPC346
0.601	Remote Similarity	NPC147091
0.601	Remote Similarity	NPC472358
0.601	Remote Similarity	NPC99723
0.6009	Remote Similarity	NPC311781
0.6009	Remote Similarity	NPC301501
0.6	Remote Similarity	NPC215829
0.6	Remote Similarity	NPC195325
0.6	Remote Similarity	NPC471559
0.6	Remote Similarity	NPC33256
0.6	Remote Similarity	NPC97072
0.599	Remote Similarity	NPC470996
0.599	Remote Similarity	NPC241704
0.599	Remote Similarity	NPC474470
0.599	Remote Similarity	NPC283207
0.599	Remote Similarity	NPC473008
0.5989	Remote Similarity	NPC281104
0.5989	Remote Similarity	NPC476944
0.5989	Remote Similarity	NPC46896
0.5983	Remote Similarity	NPC131258
0.5979	Remote Similarity	NPC471174
0.5979	Remote Similarity	NPC216755
0.5979	Remote Similarity	NPC302987
0.5978	Remote Similarity	NPC477645
0.5978	Remote Similarity	NPC202260
0.5977	Remote Similarity	NPC476351
0.5977	Remote Similarity	NPC475818
0.5971	Remote Similarity	NPC21425
0.5962	Remote Similarity	NPC138830
0.5962	Remote Similarity	NPC314100
0.5962	Remote Similarity	NPC120671
0.5962	Remote Similarity	NPC72788
0.5962	Remote Similarity	NPC226652
0.596	Remote Similarity	NPC268503
0.596	Remote Similarity	NPC256012
0.596	Remote Similarity	NPC317272
0.596	Remote Similarity	NPC42549
0.596	Remote Similarity	NPC240841
0.596	Remote Similarity	NPC250846
0.5959	Remote Similarity	NPC237259
0.5959	Remote Similarity	NPC98206
0.5959	Remote Similarity	NPC34421
0.5956	Remote Similarity	NPC186626
0.5956	Remote Similarity	NPC215109
0.5956	Remote Similarity	NPC170604
0.5954	Remote Similarity	NPC79557
0.5946	Remote Similarity	NPC201370
0.5946	Remote Similarity	NPC473983
0.5946	Remote Similarity	NPC470001
0.5946	Remote Similarity	NPC470002
0.5945	Remote Similarity	NPC198160
0.5944	Remote Similarity	NPC473344
0.5944	Remote Similarity	NPC471544
0.5943	Remote Similarity	NPC65735
0.5943	Remote Similarity	NPC285394
0.5943	Remote Similarity	NPC188377
0.5943	Remote Similarity	NPC83115
0.5939	Remote Similarity	NPC59567
0.5936	Remote Similarity	NPC476946
0.5936	Remote Similarity	NPC267632
0.5934	Remote Similarity	NPC92941

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 NPC289167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	613
0.2-0.3	998
0.3-0.4	2612
0.4-0.5	3384
0.5-0.6	1293
0.6-0.7	59
0.7-0.8	0
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
0.7166	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5262	Discontinued
0.6891	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD8161	Suspended
0.6471	Remote Similarity	NPD7577	Discontinued
0.644	Remote Similarity	NPD3861	Approved
0.644	Remote Similarity	NPD3862	Approved
0.6439	Remote Similarity	NPD5564	Approved
0.6418	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6862	Phase 2
0.6359	Remote Similarity	NPD3446	Phase 1
0.6355	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD6598	Approved
0.6345	Remote Similarity	NPD6597	Approved
0.6313	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7810	Phase 3
0.6298	Remote Similarity	NPD7811	Phase 3
0.6296	Remote Similarity	NPD6844	Discontinued
0.629	Remote Similarity	NPD1670	Discontinued
0.6286	Remote Similarity	NPD3057	Approved
0.6286	Remote Similarity	NPD3533	Approved
0.6286	Remote Similarity	NPD2491	Approved
0.6286	Remote Similarity	NPD3448	Approved
0.6286	Remote Similarity	NPD2972	Approved
0.6284	Remote Similarity	NPD5980	Discovery
0.6279	Remote Similarity	NPD5676	Approved
0.6275	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6274	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD3142	Approved
0.6271	Remote Similarity	NPD3140	Approved
0.6256	Remote Similarity	NPD7291	Discontinued
0.6256	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD4773	Phase 2
0.6243	Remote Similarity	NPD4772	Phase 2
0.6238	Remote Similarity	NPD6990	Approved
0.6238	Remote Similarity	NPD6989	Approved
0.6232	Remote Similarity	NPD3659	Discontinued
0.6216	Remote Similarity	NPD3124	Discontinued
0.6203	Remote Similarity	NPD3641	Approved
0.6203	Remote Similarity	NPD3640	Phase 3
0.6203	Remote Similarity	NPD3639	Approved
0.6198	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5228	Phase 3
0.6188	Remote Similarity	NPD4483	Discontinued
0.6164	Remote Similarity	NPD5025	Approved
0.6164	Remote Similarity	NPD7047	Phase 3
0.6162	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6321	Discontinued
0.6139	Remote Similarity	NPD7280	Phase 3
0.6139	Remote Similarity	NPD7281	Phase 3
0.6135	Remote Similarity	NPD4466	Phase 1
0.6127	Remote Similarity	NPD6891	Phase 2
0.6126	Remote Similarity	NPD5355	Approved
0.6126	Remote Similarity	NPD5356	Approved
0.6122	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD6734	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6997	Phase 2
0.607	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6390	Discontinued
0.6062	Remote Similarity	NPD7318	Phase 3
0.6061	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7627	Approved
0.6056	Remote Similarity	NPD7626	Approved
0.6053	Remote Similarity	NPD6813	Clinical (unspecified phase)
0.605	Remote Similarity	NPD5313	Approved
0.605	Remote Similarity	NPD5312	Approved
0.6038	Remote Similarity	NPD4107	Approved
0.6029	Remote Similarity	NPD6618	Phase 2
0.6028	Remote Similarity	NPD3802	Phase 3
0.602	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.601	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD4482	Phase 3
0.6	Remote Similarity	NPD6834	Approved
0.599	Remote Similarity	NPD4424	Discontinued
0.5989	Remote Similarity	NPD2569	Approved
0.5989	Remote Similarity	NPD743	Approved
0.5989	Remote Similarity	NPD2567	Approved
0.5983	Remote Similarity	NPD8153	Approved
0.5983	Remote Similarity	NPD8152	Approved
0.5981	Remote Similarity	NPD6863	Phase 2
0.5981	Remote Similarity	NPD7316	Discontinued
0.598	Remote Similarity	NPD6894	Phase 1
0.5979	Remote Similarity	NPD5977	Approved
0.5979	Remote Similarity	NPD5978	Approved
0.5979	Remote Similarity	NPD6890	Discontinued
0.5978	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.597	Remote Similarity	NPD4503	Phase 2
0.5966	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6659	Phase 2
0.5961	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5186	Approved
0.596	Remote Similarity	NPD5183	Approved
0.5959	Remote Similarity	NPD7317	Phase 3
0.5956	Remote Similarity	NPD7556	Discontinued
0.5953	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD7427	Discontinued
0.5944	Remote Similarity	NPD7713	Phase 3
0.5943	Remote Similarity	NPD5157	Phase 1
0.5943	Remote Similarity	NPD5159	Phase 2
0.5943	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD7693	Approved
0.5941	Remote Similarity	NPD5485	Approved
0.5941	Remote Similarity	NPD5484	Approved
0.5939	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD2904	Discontinued
0.5939	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD7162	Approved
0.5928	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7020	Approved
0.5926	Remote Similarity	NPD7019	Approved
0.5922	Remote Similarity	NPD6039	Approved
0.5919	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.5919	Remote Similarity	NPD4989	Phase 2
0.5918	Remote Similarity	NPD1307	Phase 2
0.5918	Remote Similarity	NPD1309	Phase 2
0.5915	Remote Similarity	NPD6874	Approved
0.5914	Remote Similarity	NPD44	Approved
0.5914	Remote Similarity	NPD6364	Approved
0.5911	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6107	Approved
0.5909	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD4679	Discontinued
0.59	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD5967	Approved
0.5897	Remote Similarity	NPD7048	Phase 3
0.5894	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD2512	Phase 3
0.5879	Remote Similarity	NPD6071	Discontinued
0.5876	Remote Similarity	NPD4098	Discontinued
0.5876	Remote Similarity	NPD7298	Approved
0.5875	Remote Similarity	NPD8102	Discontinued
0.5869	Remote Similarity	NPD4420	Approved
0.5864	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.586	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.586	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.5853	Remote Similarity	NPD4465	Phase 2
0.5853	Remote Similarity	NPD4467	Phase 2
0.585	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.5848	Remote Similarity	NPD8404	Phase 2
0.5842	Remote Similarity	NPD4662	Approved
0.5842	Remote Similarity	NPD4661	Approved
0.5842	Remote Similarity	NPD2874	Phase 2
0.5842	Remote Similarity	NPD4584	Approved
0.5838	Remote Similarity	NPD7833	Phase 2
0.5838	Remote Similarity	NPD7831	Phase 2
0.5838	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.5837	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5006	Approved
0.5833	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5005	Approved
0.5833	Remote Similarity	NPD3823	Discontinued
0.5829	Remote Similarity	NPD4127	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD6181	Discontinued
0.5825	Remote Similarity	NPD5889	Approved
0.5825	Remote Similarity	NPD8064	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6677	Suspended
0.5825	Remote Similarity	NPD5890	Approved
0.5821	Remote Similarity	NPD2898	Approved
0.582	Remote Similarity	NPD6667	Approved
0.582	Remote Similarity	NPD7440	Discontinued
0.582	Remote Similarity	NPD6666	Approved
0.582	Remote Similarity	NPD160	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD5688	Approved
0.5815	Remote Similarity	NPD7907	Approved
0.5815	Remote Similarity	NPD5689	Approved
0.581	Remote Similarity	NPD2488	Approved
0.581	Remote Similarity	NPD2490	Approved
0.5808	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.5808	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7497	Discontinued
0.5806	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6871	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4166	Phase 2
0.58	Remote Similarity	NPD7608	Discontinued
0.58	Remote Similarity	NPD3051	Approved
0.5798	Remote Similarity	NPD6748	Discontinued
0.5797	Remote Similarity	NPD6851	Approved
0.5797	Remote Similarity	NPD6853	Approved
0.5796	Remote Similarity	NPD4665	Approved
0.5796	Remote Similarity	NPD4111	Phase 1
0.5795	Remote Similarity	NPD7248	Discontinued
0.5789	Remote Similarity	NPD5852	Approved
0.5789	Remote Similarity	NPD5851	Approved
0.5787	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD3869	Phase 3
0.5781	Remote Similarity	NPD3873	Phase 3
0.5781	Remote Similarity	NPD7131	Phase 3

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