NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.08
Volume:	227.682
LogP:	0.154
LogD:	0.688
LogS:	-2.792
# Rotatable Bonds:	1
TPSA:	114.1
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	4.299
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.173
MDCK Permeability:	5.6641747505636886e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.905
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	44.987213134765625%
Volume Distribution (VD):	0.625
Pgp-substrate:	50.65010070800781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.199
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.348

ADMET: Excretion

Clearance (CL):	5.799
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.646
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.617
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.576
Skin Sensitization:	0.073
Carcinogencity:	0.808
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC212742

Natural Product ID:	NPC212742
*Common Name:**	Spongiacidin C
IUPAC Name:	(5Z)-5-(8-oxo-1,5,6,7-tetrahydropyrrolo[2,3-c]azepin-4-ylidene)imidazolidine-2,4-dione
Synonyms:	spongiacidin C
Standard InCHIKey:	MOYLWFAZPQYOGQ-VURMDHGXSA-N
Standard InCHI:	InChI=1S/C11H10N4O3/c16-9-7-5(1-3-12-7)6(2-4-13-9)8-10(17)15-11(18)14-8/h1,3,12H,2,4H2,(H,13,16)(H2,14,15,17,18)/b8-6-
SMILES:	c1c[nH]c2c1/C(=C1/C(=NC(=N1)O)O)/CCN=C2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448126
PubChem CID:	10634145
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002491] Azolidines [CHEMONTID:0000250] Imidazolidines [CHEMONTID:0001149] Imidazolidinones [CHEMONTID:0001150] Imidazolidinediones [CHEMONTID:0002273] Hydantoins

*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
NPO7079	Stylissa massa	Species	Axinellidae	Eukaryota	n.a.	Philippine	n.a.	PMID[11784156]
NPO32740	hymeniacidon sp.	Species	Halichondriidae	Eukaryota	n.a.	southern Australian	n.a.	PMID[11908980]
NPO7079	Stylissa massa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12816422]
NPO32740	hymeniacidon sp.	Species	Halichondriidae	Eukaryota	n.a.	Singapore	n.a.	PMID[15043446]
NPO7079	Stylissa massa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23684893]
NPO32740	hymeniacidon sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599282]
NPO7079	Stylissa massa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	7

Activity Type	# Activity
Individual Protein	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[510063]
NPT2213	Individual Protein	Cyclin-dependent kinase 4	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[510063]
NPT5212	Individual Protein	Sentrin-specific protease 1	Homo sapiens	IC50	>	31600.0	nM	PMID[510064]
NPT6590	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 21	Homo sapiens	IC50	=	16600.0	nM	PMID[510064]
NPT2661	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 8	Homo sapiens	IC50	>	31600.0	nM	PMID[510064]
NPT45	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	IC50	>	31600.0	nM	PMID[510064]
NPT4886	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 7	Homo sapiens	IC50	=	3800.0	nM	PMID[510064]

☑ 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 NPC212742 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	544
0.1-0.2	11040
0.2-0.3	17194
0.3-0.4	7466
0.4-0.5	2996
0.5-0.6	2314
0.6-0.7	995
0.7-0.8	145
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC162268
0.871	High Similarity	NPC475870
0.8025	Intermediate Similarity	NPC131718
0.7939	Intermediate Similarity	NPC49217
0.7818	Intermediate Similarity	NPC102423
0.7673	Intermediate Similarity	NPC159856
0.7657	Intermediate Similarity	NPC163421
0.7657	Intermediate Similarity	NPC188387
0.7622	Intermediate Similarity	NPC141353
0.759	Intermediate Similarity	NPC279918
0.7561	Intermediate Similarity	NPC33229
0.7545	Intermediate Similarity	NPC282231
0.7544	Intermediate Similarity	NPC313791
0.7543	Intermediate Similarity	NPC48938
0.753	Intermediate Similarity	NPC230869
0.7516	Intermediate Similarity	NPC104049
0.7515	Intermediate Similarity	NPC160105
0.75	Intermediate Similarity	NPC25008
0.75	Intermediate Similarity	NPC73952
0.75	Intermediate Similarity	NPC469765
0.75	Intermediate Similarity	NPC469760
0.75	Intermediate Similarity	NPC259644
0.75	Intermediate Similarity	NPC476118
0.75	Intermediate Similarity	NPC328029
0.75	Intermediate Similarity	NPC469786
0.75	Intermediate Similarity	NPC469763
0.7485	Intermediate Similarity	NPC24678
0.7485	Intermediate Similarity	NPC105818
0.747	Intermediate Similarity	NPC469762
0.7458	Intermediate Similarity	NPC314002
0.7455	Intermediate Similarity	NPC75540
0.7455	Intermediate Similarity	NPC477815
0.7455	Intermediate Similarity	NPC211572
0.7455	Intermediate Similarity	NPC212376
0.7455	Intermediate Similarity	NPC80597
0.7455	Intermediate Similarity	NPC70922
0.7453	Intermediate Similarity	NPC314372
0.7443	Intermediate Similarity	NPC220765
0.7438	Intermediate Similarity	NPC190296
0.7434	Intermediate Similarity	NPC306397
0.7414	Intermediate Similarity	NPC96890
0.7414	Intermediate Similarity	NPC184964
0.7412	Intermediate Similarity	NPC49954
0.7412	Intermediate Similarity	NPC54988
0.7412	Intermediate Similarity	NPC474561
0.741	Intermediate Similarity	NPC469785
0.7401	Intermediate Similarity	NPC204717
0.7396	Intermediate Similarity	NPC311276
0.7384	Intermediate Similarity	NPC302647
0.7374	Intermediate Similarity	NPC46580
0.7371	Intermediate Similarity	NPC42979
0.7368	Intermediate Similarity	NPC63751
0.7356	Intermediate Similarity	NPC224764
0.7341	Intermediate Similarity	NPC314603
0.7337	Intermediate Similarity	NPC77555
0.7321	Intermediate Similarity	NPC92796
0.7321	Intermediate Similarity	NPC135141
0.732	Intermediate Similarity	NPC212125
0.7318	Intermediate Similarity	NPC171171
0.7314	Intermediate Similarity	NPC59269
0.7283	Intermediate Similarity	NPC242209
0.7283	Intermediate Similarity	NPC470498
0.7278	Intermediate Similarity	NPC29702
0.7263	Intermediate Similarity	NPC15102
0.7213	Intermediate Similarity	NPC99666
0.72	Intermediate Similarity	NPC149155
0.72	Intermediate Similarity	NPC110500
0.72	Intermediate Similarity	NPC203468
0.7193	Intermediate Similarity	NPC194640
0.7193	Intermediate Similarity	NPC40779
0.7175	Intermediate Similarity	NPC126709
0.7175	Intermediate Similarity	NPC248041
0.7175	Intermediate Similarity	NPC283219
0.717	Intermediate Similarity	NPC96102
0.7168	Intermediate Similarity	NPC78020
0.7159	Intermediate Similarity	NPC267885
0.7152	Intermediate Similarity	NPC471957
0.7143	Intermediate Similarity	NPC32771
0.7134	Intermediate Similarity	NPC82295
0.7134	Intermediate Similarity	NPC324611
0.7125	Intermediate Similarity	NPC105127
0.7125	Intermediate Similarity	NPC84911
0.712	Intermediate Similarity	NPC477166
0.712	Intermediate Similarity	NPC304187
0.7119	Intermediate Similarity	NPC111275
0.7119	Intermediate Similarity	NPC248454
0.7112	Intermediate Similarity	NPC131887
0.7111	Intermediate Similarity	NPC284678
0.7104	Intermediate Similarity	NPC83111
0.7097	Intermediate Similarity	NPC165370
0.7095	Intermediate Similarity	NPC233936
0.7091	Intermediate Similarity	NPC143872
0.7088	Intermediate Similarity	NPC278434
0.7079	Intermediate Similarity	NPC141377
0.7076	Intermediate Similarity	NPC324203
0.7076	Intermediate Similarity	NPC63338
0.7076	Intermediate Similarity	NPC322976
0.7063	Intermediate Similarity	NPC29886
0.7063	Intermediate Similarity	NPC261195
0.7059	Intermediate Similarity	NPC138018
0.7059	Intermediate Similarity	NPC156704
0.7052	Intermediate Similarity	NPC41333
0.7049	Intermediate Similarity	NPC213629
0.7037	Intermediate Similarity	NPC315491
0.7037	Intermediate Similarity	NPC110126
0.7037	Intermediate Similarity	NPC45459
0.7037	Intermediate Similarity	NPC73767
0.7027	Intermediate Similarity	NPC324149
0.7024	Intermediate Similarity	NPC216713
0.7021	Intermediate Similarity	NPC192315
0.7013	Intermediate Similarity	NPC27740
0.7011	Intermediate Similarity	NPC41717
0.7006	Intermediate Similarity	NPC37268
0.7	Intermediate Similarity	NPC71037
0.6994	Remote Similarity	NPC469784
0.6994	Remote Similarity	NPC279081
0.6994	Remote Similarity	NPC469768
0.6994	Remote Similarity	NPC469779
0.6994	Remote Similarity	NPC469767
0.6994	Remote Similarity	NPC469780
0.6994	Remote Similarity	NPC469761
0.6994	Remote Similarity	NPC469783
0.6989	Remote Similarity	NPC307963
0.6984	Remote Similarity	NPC476167
0.6978	Remote Similarity	NPC311282
0.6971	Remote Similarity	NPC201700
0.6961	Remote Similarity	NPC163055
0.6957	Remote Similarity	NPC321708
0.6954	Remote Similarity	NPC282247
0.6952	Remote Similarity	NPC326634
0.6951	Remote Similarity	NPC469766
0.694	Remote Similarity	NPC94752
0.6939	Remote Similarity	NPC82370
0.6935	Remote Similarity	NPC473342
0.6935	Remote Similarity	NPC477167
0.6927	Remote Similarity	NPC145885
0.6927	Remote Similarity	NPC84827
0.6927	Remote Similarity	NPC14113
0.6918	Remote Similarity	NPC256893
0.6915	Remote Similarity	NPC251090
0.6905	Remote Similarity	NPC37548
0.6902	Remote Similarity	NPC317030
0.6902	Remote Similarity	NPC17059
0.6898	Remote Similarity	NPC106937
0.6897	Remote Similarity	NPC469813
0.6897	Remote Similarity	NPC78375
0.6897	Remote Similarity	NPC476446
0.6891	Remote Similarity	NPC470500
0.689	Remote Similarity	NPC230002
0.6889	Remote Similarity	NPC55772
0.6886	Remote Similarity	NPC288838
0.6885	Remote Similarity	NPC280290
0.6868	Remote Similarity	NPC469358
0.6865	Remote Similarity	NPC209917
0.6865	Remote Similarity	NPC296527
0.6862	Remote Similarity	NPC133366
0.6859	Remote Similarity	NPC213308
0.6855	Remote Similarity	NPC315320
0.6848	Remote Similarity	NPC315555
0.6848	Remote Similarity	NPC474707
0.6848	Remote Similarity	NPC235684
0.6842	Remote Similarity	NPC63562
0.6842	Remote Similarity	NPC470499
0.6836	Remote Similarity	NPC194411
0.6836	Remote Similarity	NPC256828
0.6833	Remote Similarity	NPC151939
0.6833	Remote Similarity	NPC68354
0.6831	Remote Similarity	NPC228835
0.6828	Remote Similarity	NPC76748
0.6825	Remote Similarity	NPC222018
0.6823	Remote Similarity	NPC300183
0.6816	Remote Similarity	NPC469717
0.6813	Remote Similarity	NPC472861
0.6813	Remote Similarity	NPC184932
0.6813	Remote Similarity	NPC471322
0.6813	Remote Similarity	NPC314394
0.6811	Remote Similarity	NPC204565
0.681	Remote Similarity	NPC125746
0.6809	Remote Similarity	NPC474177
0.6809	Remote Similarity	NPC473821
0.6809	Remote Similarity	NPC84853
0.6805	Remote Similarity	NPC13432
0.6805	Remote Similarity	NPC282531
0.6804	Remote Similarity	NPC470505
0.6802	Remote Similarity	NPC285469
0.6802	Remote Similarity	NPC5145
0.6798	Remote Similarity	NPC158129
0.6798	Remote Similarity	NPC273532
0.6796	Remote Similarity	NPC176199
0.6796	Remote Similarity	NPC215795
0.6796	Remote Similarity	NPC11126
0.6796	Remote Similarity	NPC213468
0.6791	Remote Similarity	NPC92111
0.6789	Remote Similarity	NPC74153
0.6788	Remote Similarity	NPC476073
0.6786	Remote Similarity	NPC220523
0.6786	Remote Similarity	NPC302159
0.6784	Remote Similarity	NPC200214
0.678	Remote Similarity	NPC319456
0.6778	Remote Similarity	NPC476419

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 NPC212742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	873
0.2-0.3	899
0.3-0.4	1857
0.4-0.5	2665
0.5-0.6	2029
0.6-0.7	568
0.7-0.8	44
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7816	Intermediate Similarity	NPD706	Phase 1
0.7688	Intermediate Similarity	NPD3178	Discontinued
0.7602	Intermediate Similarity	NPD5065	Approved
0.7595	Intermediate Similarity	NPD1592	Phase 3
0.75	Intermediate Similarity	NPD5138	Approved
0.75	Intermediate Similarity	NPD5140	Approved
0.7434	Intermediate Similarity	NPD9080	Approved
0.7427	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6595	Phase 3
0.732	Intermediate Similarity	NPD9284	Approved
0.7278	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7948	Phase 1
0.7233	Intermediate Similarity	NPD9506	Approved
0.7219	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5255	Approved
0.7216	Intermediate Similarity	NPD2144	Approved
0.7205	Intermediate Similarity	NPD1649	Discontinued
0.7202	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD482	Approved
0.7189	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1352	Discontinued
0.717	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5596	Phase 2
0.7126	Intermediate Similarity	NPD1325	Approved
0.7126	Intermediate Similarity	NPD1326	Approved
0.712	Intermediate Similarity	NPD2127	Suspended
0.7119	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5117	Phase 2
0.7095	Intermediate Similarity	NPD3038	Discontinued
0.7081	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3813	Approved
0.7039	Intermediate Similarity	NPD6452	Discontinued
0.7037	Intermediate Similarity	NPD786	Approved
0.7037	Intermediate Similarity	NPD484	Approved
0.7018	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD1096	Discontinued
0.7011	Intermediate Similarity	NPD424	Approved
0.7011	Intermediate Similarity	NPD425	Approved
0.7006	Intermediate Similarity	NPD2928	Phase 2
0.6989	Remote Similarity	NPD1038	Approved
0.6978	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2095	Phase 2
0.6961	Remote Similarity	NPD2092	Phase 2
0.6961	Remote Similarity	NPD2094	Phase 2
0.6961	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1722	Approved
0.6949	Remote Similarity	NPD1599	Approved
0.6946	Remote Similarity	NPD4702	Approved
0.6946	Remote Similarity	NPD4703	Approved
0.6936	Remote Similarity	NPD8026	Phase 1
0.6935	Remote Similarity	NPD3404	Approved
0.6923	Remote Similarity	NPD2091	Phase 2
0.6923	Remote Similarity	NPD2096	Phase 2
0.6914	Remote Similarity	NPD1248	Discontinued
0.6909	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3717	Discontinued
0.6906	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD8431	Approved
0.6902	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD802	Phase 2
0.6889	Remote Similarity	NPD4076	Approved
0.6889	Remote Similarity	NPD4079	Approved
0.6882	Remote Similarity	NPD4699	Discontinued
0.6875	Remote Similarity	NPD2844	Phase 3
0.6868	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4463	Approved
0.6864	Remote Similarity	NPD4462	Approved
0.6862	Remote Similarity	NPD4999	Phase 3
0.6862	Remote Similarity	NPD4998	Phase 3
0.686	Remote Similarity	NPD2582	Approved
0.686	Remote Similarity	NPD2581	Approved
0.6857	Remote Similarity	NPD926	Approved
0.6857	Remote Similarity	NPD925	Approved
0.6855	Remote Similarity	NPD9206	Approved
0.6855	Remote Similarity	NPD9207	Approved
0.6854	Remote Similarity	NPD750	Phase 2
0.6853	Remote Similarity	NPD7470	Discontinued
0.6848	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6665	Discontinued
0.6833	Remote Similarity	NPD3506	Approved
0.6833	Remote Similarity	NPD3505	Approved
0.6828	Remote Similarity	NPD1043	Phase 3
0.6816	Remote Similarity	NPD4128	Approved
0.6813	Remote Similarity	NPD9726	Discontinued
0.6805	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5901	Discontinued
0.6802	Remote Similarity	NPD3013	Phase 3
0.6802	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3082	Discontinued
0.6791	Remote Similarity	NPD5081	Phase 1
0.6791	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5082	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4612	Discontinued
0.6774	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD991	Phase 2
0.6765	Remote Similarity	NPD2172	Phase 1
0.6763	Remote Similarity	NPD9382	Approved
0.6763	Remote Similarity	NPD9383	Approved
0.6755	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD416	Approved
0.6742	Remote Similarity	NPD565	Phase 2
0.674	Remote Similarity	NPD4181	Approved
0.6738	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1392	Approved
0.6734	Remote Similarity	NPD8093	Discontinued
0.6721	Remote Similarity	NPD1570	Approved
0.672	Remote Similarity	NPD5428	Discontinued
0.672	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1315	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3814	Phase 1
0.6718	Remote Similarity	NPD1915	Phase 1
0.6716	Remote Similarity	NPD5612	Discontinued
0.6708	Remote Similarity	NPD803	Phase 1
0.6706	Remote Similarity	NPD3100	Discontinued
0.6705	Remote Similarity	NPD8129	Discovery
0.6688	Remote Similarity	NPD9357	Approved
0.6685	Remote Similarity	NPD5100	Phase 3
0.6684	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1598	Discontinued
0.6667	Remote Similarity	NPD9392	Approved
0.6667	Remote Similarity	NPD2872	Phase 2
0.6667	Remote Similarity	NPD9396	Approved
0.6667	Remote Similarity	NPD1234	Discontinued
0.665	Remote Similarity	NPD3330	Phase 1
0.665	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3439	Approved
0.6633	Remote Similarity	NPD5426	Phase 3
0.663	Remote Similarity	NPD9690	Approved
0.6629	Remote Similarity	NPD5611	Phase 2
0.6617	Remote Similarity	NPD8094	Discontinued
0.6614	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD3575	Approved
0.6608	Remote Similarity	NPD3576	Approved
0.6604	Remote Similarity	NPD9583	Approved
0.6603	Remote Similarity	NPD271	Approved
0.6603	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD268	Approved
0.66	Remote Similarity	NPD3570	Phase 2
0.66	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.66	Remote Similarity	NPD949	Phase 1
0.6591	Remote Similarity	NPD9705	Discontinued
0.6591	Remote Similarity	NPD1403	Approved
0.6591	Remote Similarity	NPD1404	Approved
0.6591	Remote Similarity	NPD112	Approved
0.6588	Remote Similarity	NPD7469	Discontinued
0.6582	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4615	Phase 2
0.6579	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD966	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD796	Phase 2
0.6566	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4511	Phase 1
0.6561	Remote Similarity	NPD8063	Discontinued
0.6556	Remote Similarity	NPD2619	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2620	Phase 2
0.6555	Remote Similarity	NPD6165	Phase 2
0.6555	Remote Similarity	NPD6164	Phase 2
0.655	Remote Similarity	NPD8321	Discontinued
0.655	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD4548	Discontinued
0.6545	Remote Similarity	NPD1173	Approved
0.6543	Remote Similarity	NPD3475	Approved
0.6543	Remote Similarity	NPD3961	Discontinued
0.6543	Remote Similarity	NPD3476	Approved
0.6538	Remote Similarity	NPD158	Discontinued
0.6537	Remote Similarity	NPD534	Phase 2
0.6537	Remote Similarity	NPD537	Phase 2
0.6536	Remote Similarity	NPD2639	Approved
0.6536	Remote Similarity	NPD2642	Approved
0.6533	Remote Similarity	NPD2187	Approved
0.6533	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2189	Approved
0.6532	Remote Similarity	NPD510	Phase 1
0.6532	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3262	Approved
0.6529	Remote Similarity	NPD9074	Approved
0.6529	Remote Similarity	NPD9075	Approved
0.6526	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD1235	Phase 3
0.6522	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8386	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