NPASS Compound

Structure

NPC147810 OpenBabel07101718272D 23 27 0 0 0 0 0 0 0 0999 V2000 5.4456 1.1849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3880 0.4163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8087 1.6192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6935 0.0818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1142 1.2847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0566 0.5160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 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 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -1.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4197 0.0818 0.0000 N 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 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 10 2 0 0 0 0 4 13 2 0 0 0 0 5 7 1 0 0 0 0 5 12 1 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 21 2 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 18 2 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.09
Volume:	315.87
LogP:	3.005
LogD:	2.484
LogS:	-3.493
# Rotatable Bonds:	2
TPSA:	64.16
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	3.392
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.002
MDCK Permeability:	4.450696360436268e-05
Pgp-inhibitor:	0.061
Pgp-substrate:	0.517
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.888
Plasma Protein Binding (PPB):	94.71620178222656%
Volume Distribution (VD):	1.101
Pgp-substrate:	2.6444342136383057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.881
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.131
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.685
CYP2D6-inhibitor:	0.293
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.22
CYP3A4-substrate:	0.32

ADMET: Excretion

Clearance (CL):	3.289
Half-life (T1/2):	0.262

ADMET: Toxicity

hERG Blockers:	0.456
Human Hepatotoxicity (H-HT):	0.79
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.931
Rat Oral Acute Toxicity:	0.487
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.744
Carcinogencity:	0.786
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC147810

Natural Product ID:	NPC147810
*Common Name:**	XQGLKIJVEQNZIJ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	N-Deacetylkuanoniamine D
Standard InCHIKey:	XQGLKIJVEQNZIJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14N4S/c19-7-5-12-15-14-11(10-3-1-2-4-13(10)22-15)6-8-20-16(14)17-18(12)23-9-21-17/h1-4,6,8-9,22H,5,7,19H2
SMILES:	c1ccc2c(-c3ccnc4c3c(c(CCN)c3c4ncs3)N2)c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464309
PubChem CID:	10403598
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0002827] Pyrido[2,3,4-kl]acridines

*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
NPO33149	oceanapia sp.	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843591]
NPO33149	oceanapia sp.	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921437]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812214]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20491501]
NPO33149	oceanapia sp.	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7769396]
NPO33149	oceanapia sp.	Species	Phloeodictyidae	Eukaryota	n.a.	micronesian	n.a.	PMID[9514015]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	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
ED50	1
IC50	2
MIC	2
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	2
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1.2	ug.mL-1	PMID[528312]
NPT2103	Cell Line	MONO-MAC-6	Homo sapiens	IC50	=	2.0	ug.mL-1	PMID[528312]
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	Activity	=	36.0	%	PMID[528312]
NPT1316	Individual Protein	Adenosine A2a receptor	Rattus norvegicus	Activity	=	46.0	%	PMID[528312]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	ED50	=	141.0	ppm	PMID[528312]
NPT2	Others	Unspecified		Activity	=	30.0	%	PMID[528312]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2500.0	nM	PMID[528313]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	2500.0	nM	PMID[528313]

☑ 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 NPC147810 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	1997
0.1-0.2	16628
0.2-0.3	17039
0.3-0.4	3104
0.4-0.5	2267
0.5-0.6	1354
0.6-0.7	290
0.7-0.8	9
0.8-0.85	3
0.85-0.9	1
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9585	High Similarity	NPC173344
0.9536	High Similarity	NPC149014
0.9439	High Similarity	NPC77022
0.9391	High Similarity	NPC216221
0.8731	High Similarity	NPC175916
0.8593	High Similarity	NPC66699
0.8465	Intermediate Similarity	NPC124636
0.8424	Intermediate Similarity	NPC193370
0.7653	Intermediate Similarity	NPC164228
0.7449	Intermediate Similarity	NPC297034
0.7358	Intermediate Similarity	NPC317105
0.7354	Intermediate Similarity	NPC325903
0.7263	Intermediate Similarity	NPC161108
0.7165	Intermediate Similarity	NPC215584
0.7165	Intermediate Similarity	NPC44773
0.7143	Intermediate Similarity	NPC469811
0.7105	Intermediate Similarity	NPC321911
0.71	Intermediate Similarity	NPC471579
0.709	Intermediate Similarity	NPC63545
0.7065	Intermediate Similarity	NPC280852
0.7053	Intermediate Similarity	NPC179787
0.7053	Intermediate Similarity	NPC201380
0.699	Remote Similarity	NPC122141
0.6954	Remote Similarity	NPC470203
0.6915	Remote Similarity	NPC201634
0.6904	Remote Similarity	NPC470204
0.689	Remote Similarity	NPC103119
0.6872	Remote Similarity	NPC476219
0.6869	Remote Similarity	NPC225018
0.6867	Remote Similarity	NPC24802
0.6866	Remote Similarity	NPC91895
0.6856	Remote Similarity	NPC470823
0.6856	Remote Similarity	NPC216713
0.6853	Remote Similarity	NPC56765
0.6853	Remote Similarity	NPC474791
0.6825	Remote Similarity	NPC284635
0.6823	Remote Similarity	NPC288838
0.6809	Remote Similarity	NPC169433
0.6804	Remote Similarity	NPC40070
0.6802	Remote Similarity	NPC236711
0.6792	Remote Similarity	NPC272458
0.6779	Remote Similarity	NPC467063
0.6777	Remote Similarity	NPC231536
0.675	Remote Similarity	NPC90723
0.6737	Remote Similarity	NPC115611
0.6718	Remote Similarity	NPC53947
0.6718	Remote Similarity	NPC148592
0.6701	Remote Similarity	NPC470111
0.6701	Remote Similarity	NPC471957
0.6697	Remote Similarity	NPC469308
0.6684	Remote Similarity	NPC470233
0.6683	Remote Similarity	NPC318065
0.6683	Remote Similarity	NPC206819
0.6667	Remote Similarity	NPC251722
0.6667	Remote Similarity	NPC478184
0.6667	Remote Similarity	NPC320863
0.6667	Remote Similarity	NPC105127
0.6667	Remote Similarity	NPC314102
0.665	Remote Similarity	NPC474958
0.6636	Remote Similarity	NPC265576
0.6634	Remote Similarity	NPC274229
0.6633	Remote Similarity	NPC216643
0.6633	Remote Similarity	NPC286427
0.6616	Remote Similarity	NPC476297
0.6615	Remote Similarity	NPC88121
0.6614	Remote Similarity	NPC96102
0.66	Remote Similarity	NPC41257
0.6598	Remote Similarity	NPC86288
0.6597	Remote Similarity	NPC110126
0.6585	Remote Similarity	NPC82331
0.6579	Remote Similarity	NPC84911
0.6573	Remote Similarity	NPC255909
0.6567	Remote Similarity	NPC229173
0.6566	Remote Similarity	NPC200214
0.6562	Remote Similarity	NPC469780
0.6562	Remote Similarity	NPC469768
0.6562	Remote Similarity	NPC469767
0.6562	Remote Similarity	NPC469761
0.6562	Remote Similarity	NPC469784
0.6562	Remote Similarity	NPC469783
0.6562	Remote Similarity	NPC469779
0.6537	Remote Similarity	NPC97343
0.6528	Remote Similarity	NPC469766
0.6526	Remote Similarity	NPC29886
0.6526	Remote Similarity	NPC261195
0.6524	Remote Similarity	NPC307191
0.652	Remote Similarity	NPC56233
0.6517	Remote Similarity	NPC293487
0.6517	Remote Similarity	NPC221786
0.6517	Remote Similarity	NPC135141
0.6517	Remote Similarity	NPC475990
0.6517	Remote Similarity	NPC92796
0.6517	Remote Similarity	NPC474880
0.651	Remote Similarity	NPC88097
0.651	Remote Similarity	NPC73767
0.6502	Remote Similarity	NPC478182
0.648	Remote Similarity	NPC143872
0.6477	Remote Similarity	NPC279081
0.6468	Remote Similarity	NPC128244
0.6462	Remote Similarity	NPC108011
0.6459	Remote Similarity	NPC248454
0.6456	Remote Similarity	NPC194411
0.6447	Remote Similarity	NPC21605
0.644	Remote Similarity	NPC325252
0.6439	Remote Similarity	NPC478183
0.6438	Remote Similarity	NPC167710
0.6438	Remote Similarity	NPC272483
0.6436	Remote Similarity	NPC477591
0.6436	Remote Similarity	NPC282398
0.6429	Remote Similarity	NPC475288
0.6429	Remote Similarity	NPC285731
0.641	Remote Similarity	NPC190296
0.641	Remote Similarity	NPC20144
0.6406	Remote Similarity	NPC324149
0.6406	Remote Similarity	NPC216550
0.6402	Remote Similarity	NPC82295
0.64	Remote Similarity	NPC138842
0.6394	Remote Similarity	NPC477611
0.6392	Remote Similarity	NPC230002
0.6387	Remote Similarity	NPC198988
0.6386	Remote Similarity	NPC167635
0.6386	Remote Similarity	NPC469897
0.6386	Remote Similarity	NPC193740
0.6382	Remote Similarity	NPC33421
0.6377	Remote Similarity	NPC474897
0.6376	Remote Similarity	NPC326422
0.6373	Remote Similarity	NPC478185
0.6368	Remote Similarity	NPC473930
0.6364	Remote Similarity	NPC37423
0.6364	Remote Similarity	NPC275305
0.6356	Remote Similarity	NPC153467
0.6355	Remote Similarity	NPC99939
0.6355	Remote Similarity	NPC308931
0.6355	Remote Similarity	NPC15102
0.6345	Remote Similarity	NPC159856
0.6345	Remote Similarity	NPC314372
0.634	Remote Similarity	NPC312092
0.6338	Remote Similarity	NPC163055
0.6337	Remote Similarity	NPC51054
0.633	Remote Similarity	NPC315617
0.633	Remote Similarity	NPC287895
0.633	Remote Similarity	NPC316359
0.6327	Remote Similarity	NPC473362
0.6327	Remote Similarity	NPC166492
0.632	Remote Similarity	NPC251936
0.6316	Remote Similarity	NPC179365
0.6303	Remote Similarity	NPC68354
0.6303	Remote Similarity	NPC59269
0.6303	Remote Similarity	NPC237188
0.63	Remote Similarity	NPC24678
0.63	Remote Similarity	NPC105818
0.6298	Remote Similarity	NPC32534
0.6291	Remote Similarity	NPC191415
0.6274	Remote Similarity	NPC176199
0.6274	Remote Similarity	NPC215795
0.6263	Remote Similarity	NPC204141
0.6262	Remote Similarity	NPC48938
0.6262	Remote Similarity	NPC102755
0.6261	Remote Similarity	NPC34837
0.6257	Remote Similarity	NPC146373
0.6257	Remote Similarity	NPC166424
0.6257	Remote Similarity	NPC245244
0.6256	Remote Similarity	NPC316018
0.6256	Remote Similarity	NPC314058
0.6256	Remote Similarity	NPC476464
0.625	Remote Similarity	NPC63751
0.6243	Remote Similarity	NPC473762
0.6239	Remote Similarity	NPC88115
0.6238	Remote Similarity	NPC259644
0.6238	Remote Similarity	NPC469763
0.6238	Remote Similarity	NPC469765
0.6238	Remote Similarity	NPC25008
0.6238	Remote Similarity	NPC73952
0.6238	Remote Similarity	NPC469786
0.6238	Remote Similarity	NPC469760
0.6237	Remote Similarity	NPC46358
0.6237	Remote Similarity	NPC150259
0.6233	Remote Similarity	NPC284678
0.623	Remote Similarity	NPC475450
0.6226	Remote Similarity	NPC157583
0.6224	Remote Similarity	NPC59084
0.6222	Remote Similarity	NPC106757
0.6221	Remote Similarity	NPC317030
0.622	Remote Similarity	NPC39092
0.6211	Remote Similarity	NPC477113
0.6211	Remote Similarity	NPC473587
0.6209	Remote Similarity	NPC317054
0.6207	Remote Similarity	NPC80597
0.6207	Remote Similarity	NPC70922
0.6207	Remote Similarity	NPC75540
0.6207	Remote Similarity	NPC211572
0.6207	Remote Similarity	NPC212376
0.6204	Remote Similarity	NPC49051
0.6203	Remote Similarity	NPC122718
0.6203	Remote Similarity	NPC27740
0.6199	Remote Similarity	NPC294693
0.6195	Remote Similarity	NPC317701
0.6193	Remote Similarity	NPC473868
0.6193	Remote Similarity	NPC63157
0.6186	Remote Similarity	NPC218268

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 NPC147810 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	586
0.1-0.2	1045
0.2-0.3	1513
0.3-0.4	2417
0.4-0.5	2156
0.5-0.6	1230
0.6-0.7	197
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7571	Intermediate Similarity	NPD2815	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3348	Phase 2
0.724	Intermediate Similarity	NPD1648	Phase 1
0.724	Intermediate Similarity	NPD1647	Phase 1
0.7198	Intermediate Similarity	NPD7127	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3610	Approved
0.7172	Intermediate Similarity	NPD3609	Approved
0.7136	Intermediate Similarity	NPD3015	Discontinued
0.7135	Intermediate Similarity	NPD1597	Phase 1
0.7135	Intermediate Similarity	NPD976	Approved
0.7135	Intermediate Similarity	NPD977	Approved
0.7135	Intermediate Similarity	NPD975	Approved
0.7129	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD3859	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4547	Phase 3
0.7	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5106	Approved
0.6976	Remote Similarity	NPD5105	Approved
0.6961	Remote Similarity	NPD4050	Phase 1
0.6954	Remote Similarity	NPD5315	Discontinued
0.6927	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7394	Phase 2
0.6919	Remote Similarity	NPD2717	Phase 2
0.6919	Remote Similarity	NPD3323	Discontinued
0.6911	Remote Similarity	NPD1683	Approved
0.6909	Remote Similarity	NPD3843	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD2837	Discontinued
0.69	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2720	Phase 1
0.6857	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4865	Approved
0.6823	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5462	Discontinued
0.6816	Remote Similarity	NPD2640	Approved
0.6816	Remote Similarity	NPD2641	Approved
0.6814	Remote Similarity	NPD2771	Approved
0.6806	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD2409	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD2735	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5828	Phase 2
0.6754	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3100	Discontinued
0.6746	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6816	Phase 3
0.6719	Remote Similarity	NPD649	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4509	Discontinued
0.6712	Remote Similarity	NPD4471	Approved
0.6712	Remote Similarity	NPD4472	Approved
0.6702	Remote Similarity	NPD1722	Approved
0.67	Remote Similarity	NPD5436	Phase 1
0.67	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4181	Approved
0.6697	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5438	Approved
0.6667	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5439	Approved
0.6667	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1403	Approved
0.665	Remote Similarity	NPD1404	Approved
0.6636	Remote Similarity	NPD4470	Phase 2
0.6633	Remote Similarity	NPD2172	Phase 1
0.6618	Remote Similarity	NPD5412	Discontinued
0.6618	Remote Similarity	NPD7111	Discontinued
0.6614	Remote Similarity	NPD1255	Approved
0.6614	Remote Similarity	NPD1254	Approved
0.6614	Remote Similarity	NPD1256	Approved
0.6614	Remote Similarity	NPD1253	Approved
0.6614	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD1895	Discontinued
0.6602	Remote Similarity	NPD4128	Approved
0.6601	Remote Similarity	NPD2639	Approved
0.6601	Remote Similarity	NPD2642	Approved
0.659	Remote Similarity	NPD6224	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2430	Phase 2
0.658	Remote Similarity	NPD2006	Phase 2
0.657	Remote Similarity	NPD6044	Discontinued
0.6569	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4886	Phase 2
0.6559	Remote Similarity	NPD947	Approved
0.6557	Remote Similarity	NPD4902	Discontinued
0.6557	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD1928	Discontinued
0.6555	Remote Similarity	NPD1873	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6133	Discontinued
0.6542	Remote Similarity	NPD2818	Discontinued
0.6535	Remote Similarity	NPD1556	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD715	Phase 3
0.6517	Remote Similarity	NPD5418	Discontinued
0.651	Remote Similarity	NPD786	Approved
0.6509	Remote Similarity	NPD1227	Phase 2
0.6498	Remote Similarity	NPD5904	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD45	Approved
0.6492	Remote Similarity	NPD6554	Approved
0.649	Remote Similarity	NPD2406	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD6968	Phase 2
0.6483	Remote Similarity	NPD6969	Phase 2
0.6481	Remote Similarity	NPD3404	Approved
0.6477	Remote Similarity	NPD7135	Phase 2
0.6468	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7027	Phase 3
0.6458	Remote Similarity	NPD2057	Approved
0.6458	Remote Similarity	NPD2058	Phase 2
0.6458	Remote Similarity	NPD2059	Approved
0.645	Remote Similarity	NPD6285	Phase 2
0.6449	Remote Similarity	NPD3961	Discontinued
0.6429	Remote Similarity	NPD2736	Phase 1
0.6429	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD3385	Approved
0.6419	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD4075	Phase 2
0.641	Remote Similarity	NPD4510	Discontinued
0.6407	Remote Similarity	NPD6171	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD2793	Discontinued
0.6394	Remote Similarity	NPD7217	Approved
0.6394	Remote Similarity	NPD7216	Approved
0.6386	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7564	Discontinued
0.6381	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5270	Discontinued
0.6378	Remote Similarity	NPD5254	Discontinued
0.6372	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD412	Approved
0.6364	Remote Similarity	NPD1661	Suspended
0.6364	Remote Similarity	NPD991	Phase 2
0.6364	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5065	Approved
0.6364	Remote Similarity	NPD7423	Phase 2
0.6359	Remote Similarity	NPD1235	Phase 3
0.6356	Remote Similarity	NPD6156	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD754	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD3829	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4615	Phase 2
0.6329	Remote Similarity	NPD4320	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD5021	Discontinued
0.6327	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5864	Phase 2
0.6326	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6958	Approved
0.632	Remote Similarity	NPD6957	Approved
0.6318	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7264	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD3505	Approved
0.6303	Remote Similarity	NPD3506	Approved
0.6301	Remote Similarity	NPD6265	Discontinued
0.6301	Remote Similarity	NPD5428	Discontinued
0.6301	Remote Similarity	NPD5615	Phase 2
0.6295	Remote Similarity	NPD6129	Phase 2
0.6295	Remote Similarity	NPD6132	Phase 1
0.6294	Remote Similarity	NPD5503	Approved
0.6294	Remote Similarity	NPD5502	Approved
0.6293	Remote Similarity	NPD6771	Discontinued
0.6287	Remote Similarity	NPD2165	Phase 1
0.6286	Remote Similarity	NPD3799	Suspended
0.6283	Remote Similarity	NPD2849	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD6149	Phase 2
0.6274	Remote Similarity	NPD4076	Approved
0.6274	Remote Similarity	NPD4079	Approved
0.6268	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD3469	Phase 3
0.6261	Remote Similarity	NPD6749	Phase 1
0.6261	Remote Similarity	NPD6170	Phase 2
0.6256	Remote Similarity	NPD2580	Discontinued
0.6256	Remote Similarity	NPD3114	Approved
0.6256	Remote Similarity	NPD3113	Approved
0.6256	Remote Similarity	NPD3115	Approved
0.6256	Remote Similarity	NPD2927	Phase 3
0.6256	Remote Similarity	NPD2150	Discontinued
0.6256	Remote Similarity	NPD3112	Approved
0.625	Remote Similarity	NPD6711	Approved
0.625	Remote Similarity	NPD917	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2963	Phase 1
0.6245	Remote Similarity	NPD4051	Discontinued
0.6244	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD2316	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD4957	Phase 2
0.6233	Remote Similarity	NPD6178	Phase 3
0.6233	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD1313	Approved
0.6232	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7469	Discontinued
0.6227	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6268	Phase 1
0.6222	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD8431	Approved
0.6217	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5446	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