NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	459.98
Volume:	381.032
LogP:	-0.215
LogD:	-0.474
LogS:	-2.336
# Rotatable Bonds:	6
TPSA:	191.78
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.268
Synthetic Accessibility Score:	4.328
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.129
MDCK Permeability:	1.330193208559649e-05
Pgp-inhibitor:	0.827
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.088

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	98.48235321044922%
Volume Distribution (VD):	0.281
Pgp-substrate:	0.7481318712234497%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.368
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.111

ADMET: Excretion

Clearance (CL):	0.712
Half-life (T1/2):	0.118

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.986
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.872
Rat Oral Acute Toxicity:	0.7
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.892
Carcinogencity:	0.97
Eye Corrosion:	0.003
Eye Irritation:	0.832
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC477804

Natural Product ID:	NPC477804
*Common Name:**	disodium;[(E)-2-[3-(3,4-dihydroxyphenyl)-2-sulfonatooxy-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl] sulfate
IUPAC Name:	disodium;[(E)-2-[3-(3,4-dihydroxyphenyl)-2-sulfonatooxy-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl] sulfate
Synonyms:
Standard InCHIKey:	GEKRVOWIMFFGED-TXOOBNKBSA-L
Standard InCHI:	InChI=1S/C16H14O12S2.2Na/c17-11-3-2-10(8-12(11)18)15-16(28-30(22,23)24)27-13-4-1-9(7-14(13)26-15)5-6-25-29(19,20)21;;/h1-8,15-18H,(H,19,20,21)(H,22,23,24);;/q;2*+1/p-2/b6-5+;;
SMILES:	C1=CC2=C(C=C1/C=C/OS(=O)(=O)[O-])OC(C(O2)OS(=O)(=O)[O-])C3=CC(=C(C=C3)O)O.[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44577123
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002699] Benzodioxanes [CHEMONTID:0002704] Phenylbenzodioxanes [CHEMONTID:0002707] Phenylbenzo-1,4-dioxanes

*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
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	Vanuatu islands	n.a.	PMID[10924170]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277766]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640526]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326327]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	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	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	172.8	ug/ml	PMID[18407691]
NPT2	Others	Unspecified		IC50	>	200	ug/ml	PMID[18407691]

☑ 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 NPC477804 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	490
0.1-0.2	2039
0.2-0.3	6644
0.3-0.4	12711
0.4-0.5	3872
0.5-0.6	7553
0.6-0.7	7140
0.7-0.8	2104
0.8-0.85	138
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9179	High Similarity	NPC477800
0.9179	High Similarity	NPC477794
0.9179	High Similarity	NPC477799
0.9023	High Similarity	NPC477798
0.9023	High Similarity	NPC477797
0.8939	High Similarity	NPC187194
0.8939	High Similarity	NPC476411
0.8855	High Similarity	NPC9912
0.8779	High Similarity	NPC80600
0.8779	High Similarity	NPC472024
0.8741	High Similarity	NPC470413
0.8741	High Similarity	NPC138738
0.8712	High Similarity	NPC469698
0.8712	High Similarity	NPC473412
0.8702	High Similarity	NPC270849
0.8702	High Similarity	NPC26653
0.8626	High Similarity	NPC302378
0.8613	High Similarity	NPC106944
0.8561	High Similarity	NPC248355
0.8561	High Similarity	NPC166040
0.8551	High Similarity	NPC76871
0.8551	High Similarity	NPC469661
0.8529	High Similarity	NPC199459
0.8529	High Similarity	NPC177035
0.8529	High Similarity	NPC52277
0.8527	High Similarity	NPC279379
0.8489	Intermediate Similarity	NPC246947
0.8489	Intermediate Similarity	NPC469559
0.8489	Intermediate Similarity	NPC476356
0.8489	Intermediate Similarity	NPC60249
0.8489	Intermediate Similarity	NPC189115
0.8485	Intermediate Similarity	NPC72529
0.8467	Intermediate Similarity	NPC59324
0.8467	Intermediate Similarity	NPC65530
0.8462	Intermediate Similarity	NPC109822
0.8462	Intermediate Similarity	NPC94276
0.845	Intermediate Similarity	NPC71090
0.8444	Intermediate Similarity	NPC69513
0.8444	Intermediate Similarity	NPC215833
0.8444	Intermediate Similarity	NPC25821
0.8433	Intermediate Similarity	NPC65942
0.8433	Intermediate Similarity	NPC248307
0.8429	Intermediate Similarity	NPC470950
0.8429	Intermediate Similarity	NPC185307
0.8429	Intermediate Similarity	NPC46092
0.8421	Intermediate Similarity	NPC5851
0.8421	Intermediate Similarity	NPC86030
0.8406	Intermediate Similarity	NPC212770
0.8406	Intermediate Similarity	NPC292487
0.8406	Intermediate Similarity	NPC98777
0.8406	Intermediate Similarity	NPC156376
0.8394	Intermediate Similarity	NPC242028
0.8394	Intermediate Similarity	NPC203230
0.8382	Intermediate Similarity	NPC48863
0.8382	Intermediate Similarity	NPC35731
0.8382	Intermediate Similarity	NPC251981
0.8382	Intermediate Similarity	NPC13745
0.837	Intermediate Similarity	NPC162093
0.8369	Intermediate Similarity	NPC217635
0.8369	Intermediate Similarity	NPC473045
0.8369	Intermediate Similarity	NPC470235
0.8369	Intermediate Similarity	NPC25292
0.8369	Intermediate Similarity	NPC129417
0.8369	Intermediate Similarity	NPC471667
0.8369	Intermediate Similarity	NPC283995
0.8369	Intermediate Similarity	NPC471063
0.8369	Intermediate Similarity	NPC79429
0.8357	Intermediate Similarity	NPC473792
0.8357	Intermediate Similarity	NPC475084
0.8357	Intermediate Similarity	NPC473873
0.8346	Intermediate Similarity	NPC165128
0.8346	Intermediate Similarity	NPC31707
0.8346	Intermediate Similarity	NPC158471
0.8346	Intermediate Similarity	NPC57119
0.8346	Intermediate Similarity	NPC226862
0.8333	Intermediate Similarity	NPC178284
0.8333	Intermediate Similarity	NPC58607
0.8333	Intermediate Similarity	NPC191037
0.8321	Intermediate Similarity	NPC470236
0.831	Intermediate Similarity	NPC43508
0.831	Intermediate Similarity	NPC22150
0.831	Intermediate Similarity	NPC476301
0.831	Intermediate Similarity	NPC279298
0.831	Intermediate Similarity	NPC38041
0.831	Intermediate Similarity	NPC18979
0.831	Intermediate Similarity	NPC475096
0.831	Intermediate Similarity	NPC469586
0.8309	Intermediate Similarity	NPC49074
0.8308	Intermediate Similarity	NPC261661
0.8298	Intermediate Similarity	NPC252169
0.8298	Intermediate Similarity	NPC478239
0.8298	Intermediate Similarity	NPC473044
0.8286	Intermediate Similarity	NPC186406
0.8286	Intermediate Similarity	NPC472711
0.8286	Intermediate Similarity	NPC471908
0.8284	Intermediate Similarity	NPC307110
0.8271	Intermediate Similarity	NPC183181
0.8271	Intermediate Similarity	NPC163332
0.8271	Intermediate Similarity	NPC111247
0.8271	Intermediate Similarity	NPC292056
0.8271	Intermediate Similarity	NPC147821
0.8271	Intermediate Similarity	NPC118787
0.8271	Intermediate Similarity	NPC41706
0.8271	Intermediate Similarity	NPC319625
0.8261	Intermediate Similarity	NPC25695
0.8261	Intermediate Similarity	NPC172818
0.8261	Intermediate Similarity	NPC164857
0.8258	Intermediate Similarity	NPC194519
0.8252	Intermediate Similarity	NPC205796
0.8252	Intermediate Similarity	NPC99515
0.8252	Intermediate Similarity	NPC190714
0.8252	Intermediate Similarity	NPC276753
0.8252	Intermediate Similarity	NPC125755
0.8252	Intermediate Similarity	NPC112861
0.8248	Intermediate Similarity	NPC170694
0.8248	Intermediate Similarity	NPC170779
0.8248	Intermediate Similarity	NPC87696
0.8248	Intermediate Similarity	NPC90083
0.8248	Intermediate Similarity	NPC470881
0.8239	Intermediate Similarity	NPC168579
0.8239	Intermediate Similarity	NPC469313
0.8239	Intermediate Similarity	NPC138227
0.8239	Intermediate Similarity	NPC76176
0.8239	Intermediate Similarity	NPC232228
0.8235	Intermediate Similarity	NPC26080
0.8235	Intermediate Similarity	NPC165686
0.8235	Intermediate Similarity	NPC303422
0.8235	Intermediate Similarity	NPC299144
0.8235	Intermediate Similarity	NPC85799
0.8231	Intermediate Similarity	NPC172676
0.8231	Intermediate Similarity	NPC65933
0.8231	Intermediate Similarity	NPC216929
0.8231	Intermediate Similarity	NPC312713
0.8231	Intermediate Similarity	NPC126935
0.8231	Intermediate Similarity	NPC57268
0.8227	Intermediate Similarity	NPC157816
0.8227	Intermediate Similarity	NPC140502
0.8227	Intermediate Similarity	NPC48309
0.8227	Intermediate Similarity	NPC302506
0.8222	Intermediate Similarity	NPC233224
0.8222	Intermediate Similarity	NPC79184
0.8222	Intermediate Similarity	NPC271208
0.8222	Intermediate Similarity	NPC307042
0.8209	Intermediate Similarity	NPC210674
0.8209	Intermediate Similarity	NPC474178
0.8209	Intermediate Similarity	NPC252307
0.8209	Intermediate Similarity	NPC245826
0.8201	Intermediate Similarity	NPC304152
0.8194	Intermediate Similarity	NPC39657
0.8194	Intermediate Similarity	NPC275284
0.8194	Intermediate Similarity	NPC15956
0.8194	Intermediate Similarity	NPC114505
0.8194	Intermediate Similarity	NPC193473
0.8194	Intermediate Similarity	NPC213074
0.8194	Intermediate Similarity	NPC31325
0.8194	Intermediate Similarity	NPC227902
0.8194	Intermediate Similarity	NPC224674
0.8188	Intermediate Similarity	NPC224941
0.8188	Intermediate Similarity	NPC311430
0.8188	Intermediate Similarity	NPC55040
0.8182	Intermediate Similarity	NPC114901
0.8182	Intermediate Similarity	NPC161700
0.8182	Intermediate Similarity	NPC277867
0.8182	Intermediate Similarity	NPC293701
0.8182	Intermediate Similarity	NPC48990
0.8175	Intermediate Similarity	NPC115022
0.8175	Intermediate Similarity	NPC263064
0.8175	Intermediate Similarity	NPC294166
0.8175	Intermediate Similarity	NPC6836
0.8169	Intermediate Similarity	NPC477898
0.8169	Intermediate Similarity	NPC278961
0.8169	Intermediate Similarity	NPC113680
0.8169	Intermediate Similarity	NPC37793
0.8162	Intermediate Similarity	NPC469613
0.8162	Intermediate Similarity	NPC469625
0.8162	Intermediate Similarity	NPC121376
0.8162	Intermediate Similarity	NPC166168
0.8162	Intermediate Similarity	NPC227160
0.8162	Intermediate Similarity	NPC30043
0.8162	Intermediate Similarity	NPC82111
0.8156	Intermediate Similarity	NPC300798
0.8156	Intermediate Similarity	NPC58137
0.8154	Intermediate Similarity	NPC267064
0.8154	Intermediate Similarity	NPC469412
0.8154	Intermediate Similarity	NPC472596
0.8154	Intermediate Similarity	NPC198734
0.8148	Intermediate Similarity	NPC222004
0.8148	Intermediate Similarity	NPC3439
0.8148	Intermediate Similarity	NPC285339
0.8148	Intermediate Similarity	NPC273295
0.8148	Intermediate Similarity	NPC226788
0.8148	Intermediate Similarity	NPC218856
0.8148	Intermediate Similarity	NPC202582
0.8148	Intermediate Similarity	NPC190629
0.8148	Intermediate Similarity	NPC470258
0.8148	Intermediate Similarity	NPC210623
0.8138	Intermediate Similarity	NPC175976
0.8138	Intermediate Similarity	NPC116229
0.8138	Intermediate Similarity	NPC270751
0.8138	Intermediate Similarity	NPC93924

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 NPC477804 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	965
0.2-0.3	2100
0.3-0.4	2691
0.4-0.5	1549
0.5-0.6	935
0.6-0.7	467
0.7-0.8	37
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
0.8092	Intermediate Similarity	NPD3705	Approved
0.7971	Intermediate Similarity	NPD1613	Approved
0.7971	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5283	Phase 1
0.781	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD3027	Phase 3
0.7737	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1091	Approved
0.7655	Intermediate Similarity	NPD6674	Discontinued
0.7639	Intermediate Similarity	NPD7266	Discontinued
0.7609	Intermediate Similarity	NPD2861	Phase 2
0.76	Intermediate Similarity	NPD1653	Approved
0.7574	Intermediate Similarity	NPD2982	Phase 2
0.7574	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD2981	Phase 2
0.7482	Intermediate Similarity	NPD3018	Phase 2
0.7463	Intermediate Similarity	NPD1357	Approved
0.7397	Intermediate Similarity	NPD1375	Discontinued
0.7385	Intermediate Similarity	NPD228	Approved
0.7333	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7843	Approved
0.7313	Intermediate Similarity	NPD5536	Phase 2
0.7305	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1610	Phase 2
0.7297	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7157	Approved
0.7292	Intermediate Similarity	NPD3657	Discovery
0.7287	Intermediate Similarity	NPD2684	Approved
0.7267	Intermediate Similarity	NPD5058	Phase 3
0.7259	Intermediate Similarity	NPD1548	Phase 1
0.7239	Intermediate Similarity	NPD7054	Approved
0.7222	Intermediate Similarity	NPD1558	Phase 1
0.7208	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5535	Approved
0.7195	Intermediate Similarity	NPD7074	Phase 3
0.7195	Intermediate Similarity	NPD7472	Approved
0.7192	Intermediate Similarity	NPD4538	Approved
0.7192	Intermediate Similarity	NPD7097	Phase 1
0.7192	Intermediate Similarity	NPD4536	Approved
0.7192	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4908	Phase 1
0.7179	Intermediate Similarity	NPD1934	Approved
0.7179	Intermediate Similarity	NPD37	Approved
0.7178	Intermediate Similarity	NPD3818	Discontinued
0.7172	Intermediate Similarity	NPD4340	Discontinued
0.7162	Intermediate Similarity	NPD3540	Phase 1
0.7153	Intermediate Similarity	NPD5846	Approved
0.7153	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4062	Phase 3
0.7153	Intermediate Similarity	NPD6516	Phase 2
0.7152	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD4966	Approved
0.7152	Intermediate Similarity	NPD4967	Phase 2
0.7152	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5960	Phase 3
0.7143	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5588	Approved
0.7134	Intermediate Similarity	NPD8455	Phase 2
0.7132	Intermediate Similarity	NPD968	Approved
0.7132	Intermediate Similarity	NPD1182	Approved
0.7095	Intermediate Similarity	NPD3539	Phase 1
0.7089	Intermediate Similarity	NPD3817	Phase 2
0.7089	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7199	Phase 2
0.7078	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4236	Phase 3
0.7067	Intermediate Similarity	NPD4237	Approved
0.7067	Intermediate Similarity	NPD4162	Approved
0.7066	Intermediate Similarity	NPD7808	Phase 3
0.7066	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6234	Discontinued
0.7059	Intermediate Similarity	NPD4123	Phase 3
0.7048	Intermediate Similarity	NPD6797	Phase 2
0.7044	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6233	Phase 2
0.7029	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4108	Discontinued
0.7021	Intermediate Similarity	NPD8651	Approved
0.702	Intermediate Similarity	NPD4110	Phase 3
0.702	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6331	Phase 2
0.7014	Intermediate Similarity	NPD7095	Approved
0.7006	Intermediate Similarity	NPD7251	Discontinued
0.7	Intermediate Similarity	NPD1840	Phase 2
0.7	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4060	Phase 1
0.6974	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7228	Approved
0.6966	Remote Similarity	NPD5718	Phase 2
0.6966	Remote Similarity	NPD6798	Discontinued
0.6957	Remote Similarity	NPD5585	Approved
0.6954	Remote Similarity	NPD3060	Approved
0.695	Remote Similarity	NPD5327	Phase 3
0.6947	Remote Similarity	NPD290	Approved
0.6939	Remote Similarity	NPD1933	Approved
0.6923	Remote Similarity	NPD6584	Phase 3
0.6923	Remote Similarity	NPD3687	Approved
0.6923	Remote Similarity	NPD3686	Approved
0.6918	Remote Similarity	NPD3530	Approved
0.6918	Remote Similarity	NPD3531	Approved
0.6918	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3532	Approved
0.6918	Remote Similarity	NPD2977	Approved
0.6918	Remote Similarity	NPD2978	Approved
0.6912	Remote Similarity	NPD6671	Approved
0.6906	Remote Similarity	NPD17	Approved
0.6903	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1894	Discontinued
0.6883	Remote Similarity	NPD1774	Approved
0.6879	Remote Similarity	NPD1608	Approved
0.6879	Remote Similarity	NPD2231	Phase 2
0.6879	Remote Similarity	NPD2235	Phase 2
0.6871	Remote Similarity	NPD3620	Phase 2
0.6871	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2677	Approved
0.6859	Remote Similarity	NPD2122	Discontinued
0.6857	Remote Similarity	NPD3496	Discontinued
0.6855	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5110	Phase 2
0.6849	Remote Similarity	NPD5109	Approved
0.6849	Remote Similarity	NPD5111	Phase 2
0.6849	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6166	Phase 2
0.6848	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5451	Approved
0.6842	Remote Similarity	NPD556	Approved
0.6842	Remote Similarity	NPD1652	Phase 2
0.6835	Remote Similarity	NPD4675	Approved
0.6835	Remote Similarity	NPD4678	Approved
0.6831	Remote Similarity	NPD3685	Discontinued
0.6824	Remote Similarity	NPD6355	Discontinued
0.6824	Remote Similarity	NPD5735	Approved
0.6822	Remote Similarity	NPD291	Approved
0.6821	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1358	Approved
0.6813	Remote Similarity	NPD5772	Approved
0.6813	Remote Similarity	NPD2801	Approved
0.6813	Remote Similarity	NPD5773	Approved
0.681	Remote Similarity	NPD5494	Approved
0.6805	Remote Similarity	NPD7685	Pre-registration
0.6805	Remote Similarity	NPD7240	Approved
0.6797	Remote Similarity	NPD4628	Phase 3
0.6797	Remote Similarity	NPD4535	Phase 3
0.679	Remote Similarity	NPD5604	Discontinued
0.6788	Remote Similarity	NPD6387	Discontinued
0.6788	Remote Similarity	NPD709	Approved
0.6783	Remote Similarity	NPD2922	Phase 1
0.6781	Remote Similarity	NPD4625	Phase 3
0.6774	Remote Similarity	NPD1511	Approved
0.6768	Remote Similarity	NPD8127	Discontinued
0.6763	Remote Similarity	NPD6580	Approved
0.6763	Remote Similarity	NPD6581	Approved
0.6761	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4140	Approved
0.6755	Remote Similarity	NPD6032	Approved
0.6755	Remote Similarity	NPD2161	Phase 2
0.6753	Remote Similarity	NPD6190	Approved
0.6753	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6031	Approved
0.6752	Remote Similarity	NPD6030	Approved
0.675	Remote Similarity	NPD3383	Approved
0.675	Remote Similarity	NPD3382	Approved
0.675	Remote Similarity	NPD3384	Approved
0.6739	Remote Similarity	NPD3596	Phase 2
0.6732	Remote Similarity	NPD5177	Phase 3
0.6731	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3146	Approved
0.6727	Remote Similarity	NPD3787	Discontinued
0.6726	Remote Similarity	NPD5844	Phase 1
0.6716	Remote Similarity	NPD3021	Approved
0.6716	Remote Similarity	NPD3022	Approved
0.6714	Remote Similarity	NPD6382	Discontinued
0.6714	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6582	Phase 2
0.6713	Remote Similarity	NPD4359	Approved
0.6713	Remote Similarity	NPD4749	Approved
0.6713	Remote Similarity	NPD6583	Phase 3
0.6711	Remote Similarity	NPD5763	Approved
0.6711	Remote Similarity	NPD5762	Approved
0.6709	Remote Similarity	NPD4210	Discontinued
0.6708	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6559	Discontinued
0.6691	Remote Similarity	NPD821	Approved
0.669	Remote Similarity	NPD1535	Discovery
0.669	Remote Similarity	NPD776	Approved
0.669	Remote Similarity	NPD1611	Approved
0.6689	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1512	Approved
0.6688	Remote Similarity	NPD3892	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