NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	427.27
Volume:	457.002
LogP:	1.181
LogD:	1.145
LogS:	-3.182
# Rotatable Bonds:	5
TPSA:	81.31
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.732
Synthetic Accessibility Score:	4.704
Fsp3:	0.731
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.428
MDCK Permeability:	2.6006904590758495e-05
Pgp-inhibitor:	0.175
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.079
20% Bioavailability (F20%):	0.708
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	93.30608367919922%
Volume Distribution (VD):	0.254
Pgp-substrate:	4.761666297912598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.266
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.347
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.155
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	1.018
Half-life (T1/2):	0.514

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.103
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.776

Download Data

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

Natural Product: NPC477976

Natural Product ID:	NPC477976
*Common Name:**	3-[(4bR,10aS)-2-(carboxymethyl)-4b,7,7,10a-tetramethyl-6,6a,8,9,10,10b,11,12-octahydro-5H-naphtho[2,1-f]isoquinolin-2-ium-3-yl]propanoic acid;chloride
IUPAC Name:	3-[(4bR,10aS)-2-(carboxymethyl)-4b,7,7,10a-tetramethyl-6,6a,8,9,10,10b,11,12-octahydro-5H-naphtho[2,1-f]isoquinolin-2-ium-3-yl]propanoic acid;chloride
Synonyms:	spongidine C
Standard InCHIKey:	GTWNLPWPDZPVIM-ZANDYSAHSA-N
Standard InCHI:	InChI=1S/C26H37NO4.ClH/c1-24(2)11-5-12-26(4)20(24)10-13-25(3)19-14-18(7-9-22(28)29)27(16-23(30)31)15-17(19)6-8-21(25)26;/h14-15,20-21H,5-13,16H2,1-4H3,(H-,28,29,30,31);1H/t20?,21?,25-,26-;/m0./s1
SMILES:	C[C@]12CCCC(C1CC[C@@]3(C2CCC4=C3C=C([N+](=C4)CC(=O)O)CCC(=O)O)C)(C)C.[Cl-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45266492
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tongoa, Vanuatu Islands	1996	PMID[10757711]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662110]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497946]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tong-Yong City in the South Sea, Korea	n.a.	PMID[16905319]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17567172]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988093]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18407692]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[24992702]

☑ 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	5

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	3.1	%	PMID[10757711]
NPT2	Others	Unspecified	Inhibition	=	9.1	%	PMID[10757711]
NPT2	Others	Unspecified	Inhibition	=	40.4	%	PMID[10757711]
NPT2	Others	Unspecified	Inhibition	=	30.9	%	PMID[10757711]
NPT2	Others	Unspecified	Inhibition	=	36.2	%	PMID[10757711]

☑ 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 NPC477976 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	292
0.1-0.2	1301
0.2-0.3	6843
0.3-0.4	23820
0.4-0.5	5967
0.5-0.6	2862
0.6-0.7	1509
0.7-0.8	100
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8827	High Similarity	NPC477975
0.8662	High Similarity	NPC477974
0.7977	Intermediate Similarity	NPC469938
0.7943	Intermediate Similarity	NPC213468
0.7898	Intermediate Similarity	NPC471997
0.7688	Intermediate Similarity	NPC41717
0.764	Intermediate Similarity	NPC248462
0.7514	Intermediate Similarity	NPC473763
0.7514	Intermediate Similarity	NPC117244
0.75	Intermediate Similarity	NPC322488
0.7486	Intermediate Similarity	NPC98187
0.7486	Intermediate Similarity	NPC64436
0.7444	Intermediate Similarity	NPC283219
0.7444	Intermediate Similarity	NPC126709
0.7444	Intermediate Similarity	NPC248041
0.7442	Intermediate Similarity	NPC129721
0.7433	Intermediate Similarity	NPC103230
0.7421	Intermediate Similarity	NPC50997
0.7421	Intermediate Similarity	NPC160127
0.7418	Intermediate Similarity	NPC143533
0.7394	Intermediate Similarity	NPC57994
0.7394	Intermediate Similarity	NPC195239
0.7394	Intermediate Similarity	NPC157828
0.7394	Intermediate Similarity	NPC289299
0.7391	Intermediate Similarity	NPC94752
0.7389	Intermediate Similarity	NPC14113
0.7389	Intermediate Similarity	NPC145885
0.7389	Intermediate Similarity	NPC84827
0.738	Intermediate Similarity	NPC47190
0.7377	Intermediate Similarity	NPC207851
0.7374	Intermediate Similarity	NPC139763
0.7368	Intermediate Similarity	NPC477041
0.7368	Intermediate Similarity	NPC477044
0.7354	Intermediate Similarity	NPC11445
0.7345	Intermediate Similarity	NPC70949
0.7333	Intermediate Similarity	NPC267885
0.733	Intermediate Similarity	NPC477045
0.7308	Intermediate Similarity	NPC477042
0.7297	Intermediate Similarity	NPC235684
0.7296	Intermediate Similarity	NPC471313
0.7296	Intermediate Similarity	NPC471311
0.7293	Intermediate Similarity	NPC157583
0.7292	Intermediate Similarity	NPC470279
0.7278	Intermediate Similarity	NPC203468
0.7278	Intermediate Similarity	NPC110500
0.7278	Intermediate Similarity	NPC149155
0.7273	Intermediate Similarity	NPC476446
0.7273	Intermediate Similarity	NPC78375
0.7273	Intermediate Similarity	NPC3715
0.7273	Intermediate Similarity	NPC469813
0.7247	Intermediate Similarity	NPC78020
0.7247	Intermediate Similarity	NPC201700
0.7228	Intermediate Similarity	NPC281049
0.7219	Intermediate Similarity	NPC321708
0.7219	Intermediate Similarity	NPC183805
0.7213	Intermediate Similarity	NPC300688
0.7204	Intermediate Similarity	NPC478077
0.7204	Intermediate Similarity	NPC62749
0.7202	Intermediate Similarity	NPC477977
0.72	Intermediate Similarity	NPC317752
0.7198	Intermediate Similarity	NPC475600
0.7198	Intermediate Similarity	NPC476110
0.7198	Intermediate Similarity	NPC475631
0.7198	Intermediate Similarity	NPC87152
0.7198	Intermediate Similarity	NPC111275
0.7189	Intermediate Similarity	NPC228835
0.7188	Intermediate Similarity	NPC149708
0.7166	Intermediate Similarity	NPC472323
0.7163	Intermediate Similarity	NPC470486
0.7163	Intermediate Similarity	NPC475644
0.7163	Intermediate Similarity	NPC471977
0.7163	Intermediate Similarity	NPC471190
0.7157	Intermediate Similarity	NPC475835
0.715	Intermediate Similarity	NPC293917
0.715	Intermediate Similarity	NPC318299
0.7143	Intermediate Similarity	NPC477043
0.7143	Intermediate Similarity	NPC477714
0.7143	Intermediate Similarity	NPC203754
0.7143	Intermediate Similarity	NPC150048
0.7136	Intermediate Similarity	NPC76565
0.7135	Intermediate Similarity	NPC469736
0.7135	Intermediate Similarity	NPC159125
0.7128	Intermediate Similarity	NPC57398
0.7128	Intermediate Similarity	NPC328318
0.7128	Intermediate Similarity	NPC182814
0.7128	Intermediate Similarity	NPC476874
0.7128	Intermediate Similarity	NPC328596
0.712	Intermediate Similarity	NPC20593
0.7115	Intermediate Similarity	NPC476491
0.711	Intermediate Similarity	NPC470679
0.711	Intermediate Similarity	NPC217021
0.7104	Intermediate Similarity	NPC237188
0.7104	Intermediate Similarity	NPC151939
0.7102	Intermediate Similarity	NPC80681
0.7101	Intermediate Similarity	NPC475137
0.7101	Intermediate Similarity	NPC475498
0.7098	Intermediate Similarity	NPC474916
0.7097	Intermediate Similarity	NPC46895
0.7097	Intermediate Similarity	NPC472119
0.7095	Intermediate Similarity	NPC475303
0.7095	Intermediate Similarity	NPC475596
0.7092	Intermediate Similarity	NPC98715
0.7083	Intermediate Similarity	NPC472116
0.7077	Intermediate Similarity	NPC300183
0.7071	Intermediate Similarity	NPC46225
0.7071	Intermediate Similarity	NPC225821
0.7069	Intermediate Similarity	NPC200743
0.7067	Intermediate Similarity	NPC473506
0.7065	Intermediate Similarity	NPC55772
0.7065	Intermediate Similarity	NPC75634
0.7065	Intermediate Similarity	NPC219336
0.7062	Intermediate Similarity	NPC123395
0.7062	Intermediate Similarity	NPC30456
0.7059	Intermediate Similarity	NPC473310
0.7059	Intermediate Similarity	NPC318020
0.7056	Intermediate Similarity	NPC473376
0.7053	Intermediate Similarity	NPC127647
0.7052	Intermediate Similarity	NPC473878
0.7048	Intermediate Similarity	NPC328029
0.7047	Intermediate Similarity	NPC262898
0.7037	Intermediate Similarity	NPC213629
0.7037	Intermediate Similarity	NPC255909
0.7035	Intermediate Similarity	NPC127677
0.7035	Intermediate Similarity	NPC258062
0.7033	Intermediate Similarity	NPC122968
0.7033	Intermediate Similarity	NPC477787
0.7033	Intermediate Similarity	NPC228377
0.7033	Intermediate Similarity	NPC328186
0.7031	Intermediate Similarity	NPC135950
0.7027	Intermediate Similarity	NPC15840
0.702	Intermediate Similarity	NPC317373
0.7014	Intermediate Similarity	NPC473689
0.7014	Intermediate Similarity	NPC292416
0.7012	Intermediate Similarity	NPC256893
0.7012	Intermediate Similarity	NPC324611
0.7011	Intermediate Similarity	NPC70406
0.7011	Intermediate Similarity	NPC15573
0.7011	Intermediate Similarity	NPC183662
0.7011	Intermediate Similarity	NPC217372
0.701	Intermediate Similarity	NPC102008
0.701	Intermediate Similarity	NPC34837
0.701	Intermediate Similarity	NPC477715
0.7006	Intermediate Similarity	NPC314102
0.7006	Intermediate Similarity	NPC65408
0.7006	Intermediate Similarity	NPC251722
0.7	Intermediate Similarity	NPC271862
0.7	Intermediate Similarity	NPC478158
0.7	Intermediate Similarity	NPC160105
0.6995	Remote Similarity	NPC179701
0.6995	Remote Similarity	NPC170751
0.6995	Remote Similarity	NPC109922
0.6995	Remote Similarity	NPC327769
0.6995	Remote Similarity	NPC478157
0.6984	Remote Similarity	NPC328798
0.6984	Remote Similarity	NPC325775
0.6981	Remote Similarity	NPC244839
0.6981	Remote Similarity	NPC319880
0.6981	Remote Similarity	NPC320324
0.698	Remote Similarity	NPC292517
0.6979	Remote Similarity	NPC45850
0.6978	Remote Similarity	NPC273532
0.6978	Remote Similarity	NPC126492
0.6977	Remote Similarity	NPC302159
0.6975	Remote Similarity	NPC278451
0.6974	Remote Similarity	NPC103361
0.6973	Remote Similarity	NPC11126
0.6971	Remote Similarity	NPC251391
0.6971	Remote Similarity	NPC259644
0.6971	Remote Similarity	NPC469763
0.6971	Remote Similarity	NPC25008
0.6971	Remote Similarity	NPC57797
0.6971	Remote Similarity	NPC469786
0.6971	Remote Similarity	NPC469765
0.6971	Remote Similarity	NPC250807
0.6971	Remote Similarity	NPC73952
0.6971	Remote Similarity	NPC469760
0.697	Remote Similarity	NPC327592
0.6965	Remote Similarity	NPC234999
0.6961	Remote Similarity	NPC477907
0.6961	Remote Similarity	NPC42678
0.6961	Remote Similarity	NPC477909
0.6952	Remote Similarity	NPC146824
0.6952	Remote Similarity	NPC325093
0.6952	Remote Similarity	NPC322043
0.6948	Remote Similarity	NPC237702
0.6942	Remote Similarity	NPC84815
0.6942	Remote Similarity	NPC313804
0.6942	Remote Similarity	NPC315804
0.6942	Remote Similarity	NPC301368
0.6938	Remote Similarity	NPC473850
0.6935	Remote Similarity	NPC61011
0.6934	Remote Similarity	NPC316841
0.6932	Remote Similarity	NPC70922
0.6932	Remote Similarity	NPC211572
0.6932	Remote Similarity	NPC212376
0.6932	Remote Similarity	NPC80597
0.6932	Remote Similarity	NPC75540
0.6927	Remote Similarity	NPC194881
0.6923	Remote Similarity	NPC171317
0.6923	Remote Similarity	NPC477788

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 NPC477976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	470
0.2-0.3	661
0.3-0.4	1956
0.4-0.5	2884
0.5-0.6	2221
0.6-0.7	721
0.7-0.8	69
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
0.809	Intermediate Similarity	NPD7233	Approved
0.809	Intermediate Similarity	NPD7234	Approved
0.8038	Intermediate Similarity	NPD2896	Discontinued
0.7826	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6635	Approved
0.7765	Intermediate Similarity	NPD6178	Phase 3
0.7758	Intermediate Similarity	NPD4703	Approved
0.7758	Intermediate Similarity	NPD4702	Approved
0.7738	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4805	Approved
0.7627	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3717	Discontinued
0.7619	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD750	Phase 2
0.7606	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6026	Approved
0.7579	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD2511	Approved
0.7546	Intermediate Similarity	NPD4804	Approved
0.7529	Intermediate Similarity	NPD2809	Approved
0.75	Intermediate Similarity	NPD6987	Phase 1
0.75	Intermediate Similarity	NPD5255	Approved
0.7486	Intermediate Similarity	NPD8123	Approved
0.7486	Intermediate Similarity	NPD8122	Approved
0.7473	Intermediate Similarity	NPD2091	Phase 2
0.7473	Intermediate Similarity	NPD2096	Phase 2
0.7471	Intermediate Similarity	NPD5088	Discontinued
0.7447	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD2095	Phase 2
0.7418	Intermediate Similarity	NPD2094	Phase 2
0.7418	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD2092	Phase 2
0.7398	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7187	Phase 2
0.7394	Intermediate Similarity	NPD4602	Approved
0.7394	Intermediate Similarity	NPD7944	Discontinued
0.7386	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD5043	Discontinued
0.738	Intermediate Similarity	NPD6665	Discontinued
0.7377	Intermediate Similarity	NPD7482	Phase 2
0.7377	Intermediate Similarity	NPD7483	Phase 2
0.7374	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5862	Discovery
0.7341	Intermediate Similarity	NPD4326	Phase 2
0.7341	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4427	Phase 2
0.7297	Intermediate Similarity	NPD5809	Phase 3
0.7296	Intermediate Similarity	NPD2118	Approved
0.7296	Intermediate Similarity	NPD2119	Approved
0.7288	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7469	Discontinued
0.7278	Intermediate Similarity	NPD482	Approved
0.7273	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD6999	Discontinued
0.724	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1575	Approved
0.7207	Intermediate Similarity	NPD1573	Approved
0.7191	Intermediate Similarity	NPD5611	Phase 2
0.7191	Intermediate Similarity	NPD6446	Discontinued
0.7181	Intermediate Similarity	NPD6281	Approved
0.7178	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD1631	Approved
0.7175	Intermediate Similarity	NPD3583	Phase 2
0.7174	Intermediate Similarity	NPD8408	Discontinued
0.7174	Intermediate Similarity	NPD3178	Discontinued
0.7168	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4528	Approved
0.7158	Intermediate Similarity	NPD4529	Approved
0.7158	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4526	Approved
0.7151	Intermediate Similarity	NPD4639	Approved
0.7151	Intermediate Similarity	NPD4638	Approved
0.7151	Intermediate Similarity	NPD4640	Approved
0.715	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2336	Approved
0.7143	Intermediate Similarity	NPD5471	Phase 3
0.7143	Intermediate Similarity	NPD4918	Discontinued
0.7143	Intermediate Similarity	NPD3238	Discontinued
0.7134	Intermediate Similarity	NPD3942	Approved
0.7134	Intermediate Similarity	NPD3944	Approved
0.7134	Intermediate Similarity	NPD4030	Approved
0.7134	Intermediate Similarity	NPD4029	Approved
0.7134	Intermediate Similarity	NPD4028	Approved
0.7121	Intermediate Similarity	NPD7191	Phase 2
0.712	Intermediate Similarity	NPD7619	Phase 3
0.712	Intermediate Similarity	NPD7618	Phase 3
0.7119	Intermediate Similarity	NPD5400	Approved
0.7114	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5505	Discontinued
0.7104	Intermediate Similarity	NPD2753	Discontinued
0.7098	Intermediate Similarity	NPD6846	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD8431	Approved
0.7072	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8093	Discontinued
0.7056	Intermediate Similarity	NPD5426	Phase 3
0.7056	Intermediate Similarity	NPD7103	Approved
0.7055	Intermediate Similarity	NPD3476	Approved
0.7055	Intermediate Similarity	NPD3475	Approved
0.705	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5100	Phase 3
0.7045	Intermediate Similarity	NPD2582	Approved
0.7045	Intermediate Similarity	NPD2581	Approved
0.7043	Intermediate Similarity	NPD5213	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5020	Approved
0.7039	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6363	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6452	Discontinued
0.7026	Intermediate Similarity	NPD6479	Discontinued
0.7022	Intermediate Similarity	NPD8026	Phase 1
0.702	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7957	Phase 1
0.7015	Intermediate Similarity	NPD7470	Discontinued
0.7015	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3262	Approved
0.7011	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7777	Approved
0.701	Intermediate Similarity	NPD4397	Phase 1
0.701	Intermediate Similarity	NPD53	Approved
0.701	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7778	Approved
0.7006	Intermediate Similarity	NPD200	Phase 2
0.7006	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD201	Phase 2
0.7006	Intermediate Similarity	NPD1630	Approved
0.7005	Intermediate Similarity	NPD7564	Discontinued
0.7	Intermediate Similarity	NPD8063	Discontinued
0.7	Intermediate Similarity	NPD5510	Approved
0.6995	Remote Similarity	NPD6226	Phase 3
0.6995	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2307	Discontinued
0.6989	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7562	Approved
0.6985	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8021	Approved
0.6984	Remote Similarity	NPD8020	Approved
0.698	Remote Similarity	NPD7069	Discontinued
0.698	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4889	Approved
0.6968	Remote Similarity	NPD6241	Phase 1
0.6967	Remote Similarity	NPD7824	Approved
0.6965	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4949	Discontinued
0.6959	Remote Similarity	NPD6664	Approved
0.6959	Remote Similarity	NPD3813	Approved
0.695	Remote Similarity	NPD7666	Phase 3
0.695	Remote Similarity	NPD7665	Phase 2
0.6948	Remote Similarity	NPD7791	Approved
0.6948	Remote Similarity	NPD7952	Approved
0.6948	Remote Similarity	NPD7950	Approved
0.6948	Remote Similarity	NPD7790	Approved
0.6948	Remote Similarity	NPD7953	Approved
0.6948	Remote Similarity	NPD7789	Approved
0.6948	Remote Similarity	NPD7951	Approved
0.6946	Remote Similarity	NPD8094	Discontinued
0.6935	Remote Similarity	NPD5897	Approved
0.6935	Remote Similarity	NPD5898	Approved
0.6935	Remote Similarity	NPD5899	Approved
0.6927	Remote Similarity	NPD6771	Discontinued
0.6923	Remote Similarity	NPD8356	Approved
0.6923	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4520	Approved
0.6914	Remote Similarity	NPD6158	Phase 2
0.6914	Remote Similarity	NPD510	Phase 1
0.6914	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7707	Approved
0.6906	Remote Similarity	NPD5636	Discontinued
0.6902	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.69	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3576	Approved
0.6897	Remote Similarity	NPD3575	Approved
0.6895	Remote Similarity	NPD3961	Discontinued
0.6889	Remote Similarity	NPD8129	Discovery
0.6884	Remote Similarity	NPD8114	Approved
0.6884	Remote Similarity	NPD8169	Discontinued
0.6884	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8115	Approved
0.6884	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7731	Approved
0.6872	Remote Similarity	NPD7730	Approved
0.6869	Remote Similarity	NPD7561	Approved
0.6868	Remote Similarity	NPD2781	Approved
0.6868	Remote Similarity	NPD4779	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