NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	594.01
Volume:	517.878
LogP:	0.982
LogD:	-0.15
LogS:	-3.338
# Rotatable Bonds:	9
TPSA:	221.24
# H-Bond Aceptor:	14
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	4.498
Fsp3:	0.083
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.323
MDCK Permeability:	1.2048146345478017e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.483

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	99.82660675048828%
Volume Distribution (VD):	0.073
Pgp-substrate:	0.2938038110733032%

ADMET: Metabolism

CYP1A2-inhibitor:	0.388
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.226
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.602
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.844
CYP2D6-substrate:	0.539
CYP3A4-inhibitor:	0.626
CYP3A4-substrate:	0.104

ADMET: Excretion

Clearance (CL):	0.782
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.997
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.218
Rat Oral Acute Toxicity:	0.275
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.849
Carcinogencity:	0.983
Eye Corrosion:	0.003
Eye Irritation:	0.822
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC477799

Natural Product ID:	NPC477799
*Common Name:**	disodium;[(E)-2-[3-(3,4-dihydroxyphenyl)-2-[2-hydroxy-4-[(E)-2-sulfonatooxyethenyl]phenoxy]-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl] sulfate
IUPAC Name:	disodium;[(E)-2-[3-(3,4-dihydroxyphenyl)-2-[2-hydroxy-4-[(E)-2-sulfonatooxyethenyl]phenoxy]-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl] sulfate
Synonyms:
Standard InCHIKey:	ODYCABSKQVVMGG-QZKABRJGSA-L
Standard InCHI:	InChI=1S/C24H20O14S2.2Na/c25-17-4-3-16(13-18(17)26)23-24(37-20-5-1-14(11-19(20)27)7-9-34-39(28,29)30)38-21-6-2-15(12-22(21)36-23)8-10-35-40(31,32)33;;/h1-13,23-27H,(H,28,29,30)(H,31,32,33);;/q;2*+1/p-2/b9-7+,10-8+;;
SMILES:	C1=CC2=C(C=C1/C=C/OS(=O)(=O)[O-])OC(C(O2)OC3=C(C=C(C=C3)/C=C/OS(=O)(=O)[O-])O)C4=CC(=C(C=C4)O)O.[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	24878678
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	=	173.3	ug/ml	PMID[18407691]
NPT2	Others	Unspecified		IC50	=	163.5	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 NPC477799 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	472
0.1-0.2	2063
0.2-0.3	6241
0.3-0.4	12129
0.4-0.5	4937
0.5-0.6	6594
0.6-0.7	7058
0.7-0.8	2847
0.8-0.85	326
0.85-0.9	26
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477794
1.0	High Similarity	NPC477800
0.927	High Similarity	NPC477798
0.927	High Similarity	NPC477797
0.9179	High Similarity	NPC477804
0.9137	High Similarity	NPC106944
0.913	High Similarity	NPC470413
0.913	High Similarity	NPC138738
0.8936	High Similarity	NPC469661
0.8921	High Similarity	NPC199459
0.8921	High Similarity	NPC52277
0.8921	High Similarity	NPC177035
0.8913	High Similarity	NPC187194
0.8913	High Similarity	NPC476411
0.8873	High Similarity	NPC469559
0.8873	High Similarity	NPC189115
0.8857	High Similarity	NPC65530
0.8857	High Similarity	NPC59324
0.8832	High Similarity	NPC248307
0.8832	High Similarity	NPC9912
0.8832	High Similarity	NPC65942
0.8811	High Similarity	NPC470950
0.8811	High Similarity	NPC185307
0.8811	High Similarity	NPC46092
0.8794	High Similarity	NPC98777
0.8794	High Similarity	NPC212770
0.8786	High Similarity	NPC203230
0.8786	High Similarity	NPC242028
0.8777	High Similarity	NPC35731
0.8759	High Similarity	NPC80600
0.8759	High Similarity	NPC472024
0.8759	High Similarity	NPC125755
0.875	High Similarity	NPC129417
0.875	High Similarity	NPC283995
0.875	High Similarity	NPC473045
0.875	High Similarity	NPC76176
0.875	High Similarity	NPC138227
0.875	High Similarity	NPC25292
0.875	High Similarity	NPC72529
0.875	High Similarity	NPC469313
0.875	High Similarity	NPC470235
0.875	High Similarity	NPC168579
0.8741	High Similarity	NPC476356
0.8741	High Similarity	NPC475084
0.8707	High Similarity	NPC44452
0.869	High Similarity	NPC22150
0.869	High Similarity	NPC277867
0.869	High Similarity	NPC18979
0.869	High Similarity	NPC38041
0.869	High Similarity	NPC475096
0.869	High Similarity	NPC286245
0.869	High Similarity	NPC272619
0.869	High Similarity	NPC469586
0.869	High Similarity	NPC161700
0.869	High Similarity	NPC279298
0.8686	High Similarity	NPC86030
0.8686	High Similarity	NPC307110
0.8686	High Similarity	NPC5851
0.8686	High Similarity	NPC248355
0.8686	High Similarity	NPC26653
0.8686	High Similarity	NPC166040
0.8686	High Similarity	NPC270849
0.8681	High Similarity	NPC252169
0.8681	High Similarity	NPC37793
0.8681	High Similarity	NPC473044
0.8681	High Similarity	NPC278961
0.8681	High Similarity	NPC113680
0.8681	High Similarity	NPC478239
0.8671	High Similarity	NPC472711
0.8671	High Similarity	NPC186406
0.8643	High Similarity	NPC87696
0.8643	High Similarity	NPC470881
0.8639	High Similarity	NPC116229
0.8639	High Similarity	NPC226153
0.8639	High Similarity	NPC304048
0.8633	High Similarity	NPC254275
0.863	High Similarity	NPC112861
0.863	High Similarity	NPC190714
0.863	High Similarity	NPC99515
0.8621	High Similarity	NPC471065
0.8621	High Similarity	NPC253015
0.8621	High Similarity	NPC232228
0.8613	High Similarity	NPC302378
0.8611	High Similarity	NPC140502
0.8611	High Similarity	NPC157816
0.8611	High Similarity	NPC302506
0.8611	High Similarity	NPC60249
0.8611	High Similarity	NPC48309
0.8603	High Similarity	NPC191037
0.8603	High Similarity	NPC178284
0.8603	High Similarity	NPC58607
0.8601	High Similarity	NPC262189
0.8601	High Similarity	NPC55793
0.86	High Similarity	NPC78809
0.8592	High Similarity	NPC304152
0.8571	High Similarity	NPC275284
0.8571	High Similarity	NPC193473
0.8571	High Similarity	NPC227902
0.8571	High Similarity	NPC31325
0.8571	High Similarity	NPC213074
0.8571	High Similarity	NPC473480
0.8571	High Similarity	NPC25821
0.8571	High Similarity	NPC15538
0.8571	High Similarity	NPC15956
0.8571	High Similarity	NPC6836
0.8571	High Similarity	NPC224674
0.8571	High Similarity	NPC39657
0.8571	High Similarity	NPC114505
0.8562	High Similarity	NPC476864
0.8562	High Similarity	NPC476866
0.8562	High Similarity	NPC476868
0.8562	High Similarity	NPC100998
0.8562	High Similarity	NPC476869
0.8562	High Similarity	NPC34927
0.8562	High Similarity	NPC476382
0.8562	High Similarity	NPC252292
0.8562	High Similarity	NPC34587
0.8561	High Similarity	NPC166168
0.8552	High Similarity	NPC477898
0.8542	High Similarity	NPC76871
0.854	High Similarity	NPC111247
0.854	High Similarity	NPC41706
0.854	High Similarity	NPC183181
0.854	High Similarity	NPC319625
0.854	High Similarity	NPC163332
0.854	High Similarity	NPC118787
0.854	High Similarity	NPC292056
0.854	High Similarity	NPC147821
0.8533	High Similarity	NPC21902
0.8529	High Similarity	NPC194519
0.8523	High Similarity	NPC476871
0.8523	High Similarity	NPC475224
0.8521	High Similarity	NPC77861
0.8514	High Similarity	NPC175976
0.8514	High Similarity	NPC280945
0.8511	High Similarity	NPC107478
0.8511	High Similarity	NPC188555
0.8511	High Similarity	NPC170694
0.8511	High Similarity	NPC130496
0.8511	High Similarity	NPC13745
0.8511	High Similarity	NPC251981
0.8511	High Similarity	NPC48863
0.8503	High Similarity	NPC241846
0.8503	High Similarity	NPC93610
0.8503	High Similarity	NPC476865
0.8503	High Similarity	NPC199928
0.85	High Similarity	NPC165686
0.85	High Similarity	NPC252833
0.85	High Similarity	NPC471505
0.85	High Similarity	NPC303422
0.85	High Similarity	NPC85799
0.85	High Similarity	NPC26080
0.8493	Intermediate Similarity	NPC476867
0.8493	Intermediate Similarity	NPC84181
0.8493	Intermediate Similarity	NPC292443
0.8493	Intermediate Similarity	NPC471063
0.8493	Intermediate Similarity	NPC179521
0.8483	Intermediate Similarity	NPC246947
0.8483	Intermediate Similarity	NPC5262
0.8483	Intermediate Similarity	NPC472714
0.8478	Intermediate Similarity	NPC474178
0.8478	Intermediate Similarity	NPC252307
0.8478	Intermediate Similarity	NPC245826
0.8472	Intermediate Similarity	NPC202700
0.8462	Intermediate Similarity	NPC474390
0.8456	Intermediate Similarity	NPC55158
0.8456	Intermediate Similarity	NPC286235
0.8456	Intermediate Similarity	NPC51328
0.8456	Intermediate Similarity	NPC109822
0.8456	Intermediate Similarity	NPC106138
0.8456	Intermediate Similarity	NPC94276
0.8451	Intermediate Similarity	NPC238243
0.8451	Intermediate Similarity	NPC101624
0.8451	Intermediate Similarity	NPC135777
0.8451	Intermediate Similarity	NPC142547
0.8451	Intermediate Similarity	NPC184938
0.8446	Intermediate Similarity	NPC232992
0.844	Intermediate Similarity	NPC132895
0.844	Intermediate Similarity	NPC115022
0.844	Intermediate Similarity	NPC69513
0.844	Intermediate Similarity	NPC49074
0.844	Intermediate Similarity	NPC294166
0.844	Intermediate Similarity	NPC215833
0.8435	Intermediate Similarity	NPC476301
0.8435	Intermediate Similarity	NPC43508
0.8431	Intermediate Similarity	NPC11411
0.8429	Intermediate Similarity	NPC121376
0.8425	Intermediate Similarity	NPC81638
0.8417	Intermediate Similarity	NPC184092
0.8414	Intermediate Similarity	NPC178054
0.8414	Intermediate Similarity	NPC470372
0.8411	Intermediate Similarity	NPC478268
0.8411	Intermediate Similarity	NPC474442
0.8406	Intermediate Similarity	NPC264900
0.8406	Intermediate Similarity	NPC108659
0.8406	Intermediate Similarity	NPC79715
0.8406	Intermediate Similarity	NPC231607
0.8403	Intermediate Similarity	NPC100389
0.8403	Intermediate Similarity	NPC292487
0.8403	Intermediate Similarity	NPC156376

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 NPC477799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	967
0.2-0.3	2130
0.3-0.4	2691
0.4-0.5	1565
0.5-0.6	940
0.6-0.7	428
0.7-0.8	41
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
0.8151	Intermediate Similarity	NPD7266	Discontinued
0.8112	Intermediate Similarity	NPD1613	Approved
0.8112	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD3027	Phase 3
0.7974	Intermediate Similarity	NPD1653	Approved
0.7958	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6674	Discontinued
0.7887	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1091	Approved
0.7714	Intermediate Similarity	NPD3705	Approved
0.7697	Intermediate Similarity	NPD7054	Approved
0.7651	Intermediate Similarity	NPD7074	Phase 3
0.7651	Intermediate Similarity	NPD7472	Approved
0.7639	Intermediate Similarity	NPD2861	Phase 2
0.7625	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4908	Phase 1
0.7556	Intermediate Similarity	NPD228	Approved
0.7531	Intermediate Similarity	NPD6234	Discontinued
0.753	Intermediate Similarity	NPD3818	Discontinued
0.753	Intermediate Similarity	NPD7228	Approved
0.7515	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1357	Approved
0.75	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7251	Discontinued
0.7412	Intermediate Similarity	NPD7808	Phase 3
0.741	Intermediate Similarity	NPD6166	Phase 2
0.741	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1558	Phase 1
0.7362	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7199	Phase 2
0.7329	Intermediate Similarity	NPD1934	Approved
0.7329	Intermediate Similarity	NPD37	Approved
0.7319	Intermediate Similarity	NPD5283	Phase 1
0.7308	Intermediate Similarity	NPD5058	Phase 3
0.7301	Intermediate Similarity	NPD4965	Approved
0.7301	Intermediate Similarity	NPD4967	Phase 2
0.7301	Intermediate Similarity	NPD4966	Approved
0.7284	Intermediate Similarity	NPD2978	Approved
0.7284	Intermediate Similarity	NPD2977	Approved
0.7267	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3620	Phase 2
0.7251	Intermediate Similarity	NPD7685	Pre-registration
0.7246	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7097	Phase 1
0.7226	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1610	Phase 2
0.7211	Intermediate Similarity	NPD6584	Phase 3
0.7203	Intermediate Similarity	NPD6516	Phase 2
0.7203	Intermediate Similarity	NPD5846	Approved
0.72	Intermediate Similarity	NPD6233	Phase 2
0.7197	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1548	Phase 1
0.7178	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7134	Intermediate Similarity	NPD6190	Approved
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7124	Intermediate Similarity	NPD4538	Approved
0.7124	Intermediate Similarity	NPD4536	Approved
0.7124	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2983	Phase 2
0.7123	Intermediate Similarity	NPD2982	Phase 2
0.7122	Intermediate Similarity	NPD7843	Approved
0.7117	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4340	Discontinued
0.7097	Intermediate Similarity	NPD1375	Discontinued
0.7097	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7157	Approved
0.7086	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4062	Phase 3
0.708	Intermediate Similarity	NPD2684	Approved
0.7078	Intermediate Similarity	NPD5588	Approved
0.7078	Intermediate Similarity	NPD5960	Phase 3
0.7073	Intermediate Similarity	NPD2801	Approved
0.7067	Intermediate Similarity	NPD7095	Approved
0.7059	Intermediate Similarity	NPD968	Approved
0.7055	Intermediate Similarity	NPD2981	Phase 2
0.7052	Intermediate Similarity	NPD6559	Discontinued
0.7052	Intermediate Similarity	NPD7240	Approved
0.7047	Intermediate Similarity	NPD3018	Phase 2
0.7029	Intermediate Similarity	NPD3021	Approved
0.7029	Intermediate Similarity	NPD3022	Approved
0.7019	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6583	Phase 3
0.7007	Intermediate Similarity	NPD6582	Phase 2
0.7006	Intermediate Similarity	NPD3060	Approved
0.7	Intermediate Similarity	NPD4123	Phase 3
0.6993	Remote Similarity	NPD3657	Discovery
0.6982	Remote Similarity	NPD3787	Discontinued
0.6977	Remote Similarity	NPD5844	Phase 1
0.6977	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6671	Approved
0.6971	Remote Similarity	NPD8312	Approved
0.6971	Remote Similarity	NPD8313	Approved
0.697	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1511	Approved
0.6928	Remote Similarity	NPD3817	Phase 2
0.6928	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2122	Discontinued
0.6899	Remote Similarity	NPD4237	Approved
0.6899	Remote Similarity	NPD4162	Approved
0.6899	Remote Similarity	NPD4236	Phase 3
0.6894	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3882	Suspended
0.6883	Remote Similarity	NPD5735	Approved
0.6882	Remote Similarity	NPD7680	Approved
0.6879	Remote Similarity	NPD5535	Approved
0.6875	Remote Similarity	NPD5536	Phase 2
0.6871	Remote Similarity	NPD3687	Approved
0.6871	Remote Similarity	NPD3686	Approved
0.6867	Remote Similarity	NPD1465	Phase 2
0.6867	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4108	Discontinued
0.6859	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4628	Phase 3
0.6855	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4110	Phase 3
0.6855	Remote Similarity	NPD6331	Phase 2
0.6852	Remote Similarity	NPD1512	Approved
0.6846	Remote Similarity	NPD8651	Approved
0.6845	Remote Similarity	NPD5604	Discontinued
0.6842	Remote Similarity	NPD4625	Phase 3
0.6832	Remote Similarity	NPD7213	Phase 3
0.6832	Remote Similarity	NPD7212	Phase 2
0.6829	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8127	Discontinued
0.6824	Remote Similarity	NPD2235	Phase 2
0.6824	Remote Similarity	NPD2231	Phase 2
0.6821	Remote Similarity	NPD3751	Discontinued
0.6813	Remote Similarity	NPD2677	Approved
0.6792	Remote Similarity	NPD1652	Phase 2
0.679	Remote Similarity	NPD7447	Phase 1
0.6788	Remote Similarity	NPD4675	Approved
0.6788	Remote Similarity	NPD4678	Approved
0.6788	Remote Similarity	NPD4380	Phase 2
0.6779	Remote Similarity	NPD4749	Approved
0.6774	Remote Similarity	NPD6355	Discontinued
0.6772	Remote Similarity	NPD3540	Phase 1
0.6766	Remote Similarity	NPD5772	Approved
0.6766	Remote Similarity	NPD5773	Approved
0.6763	Remote Similarity	NPD290	Approved
0.6757	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2674	Phase 3
0.675	Remote Similarity	NPD4535	Phase 3
0.6748	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5126	Approved
0.6735	Remote Similarity	NPD5125	Phase 3
0.673	Remote Similarity	NPD7037	Approved
0.6728	Remote Similarity	NPD1774	Approved
0.6723	Remote Similarity	NPD7549	Discontinued
0.6722	Remote Similarity	NPD7906	Approved
0.671	Remote Similarity	NPD4140	Approved
0.6709	Remote Similarity	NPD3539	Phase 1
0.6708	Remote Similarity	NPD5241	Discontinued
0.6705	Remote Similarity	NPD2489	Approved
0.6705	Remote Similarity	NPD27	Approved
0.6689	Remote Similarity	NPD3496	Discontinued
0.6688	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5177	Phase 3
0.6686	Remote Similarity	NPD3051	Approved
0.6686	Remote Similarity	NPD6232	Discontinued
0.6685	Remote Similarity	NPD4578	Approved
0.6685	Remote Similarity	NPD4577	Approved
0.6667	Remote Similarity	NPD4663	Approved
0.6667	Remote Similarity	NPD7039	Approved
0.6667	Remote Similarity	NPD5327	Phase 3
0.6667	Remote Similarity	NPD7038	Approved
0.6667	Remote Similarity	NPD3685	Discontinued
0.6667	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD5451	Approved
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD8054	Approved
0.6648	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD8053	Approved
0.6647	Remote Similarity	NPD2970	Approved
0.6647	Remote Similarity	NPD2969	Approved
0.6647	Remote Similarity	NPD7075	Discontinued
0.6646	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1535	Discovery
0.6642	Remote Similarity	NPD291	Approved
0.663	Remote Similarity	NPD6841	Approved
0.663	Remote Similarity	NPD6843	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data