NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	316.13
Volume:	322.347
LogP:	2.228
LogD:	0.347
LogS:	-2.74
# Rotatable Bonds:	6
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	2.447
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.744
MDCK Permeability:	2.8583772291312926e-05
Pgp-inhibitor:	0.352
Pgp-substrate:	0.242
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.587
30% Bioavailability (F30%):	0.888

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	65.6062240600586%
Volume Distribution (VD):	1.27
Pgp-substrate:	12.165777206420898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.922
CYP1A2-substrate:	0.726
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.412
CYP2C9-inhibitor:	0.813
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.823
CYP2D6-substrate:	0.797
CYP3A4-inhibitor:	0.945
CYP3A4-substrate:	0.493

ADMET: Excretion

Clearance (CL):	11.991
Half-life (T1/2):	0.838

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.441
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.844
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.324
Carcinogencity:	0.655
Eye Corrosion:	0.01
Eye Irritation:	0.091
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC477705

Natural Product ID:	NPC477705
*Common Name:**	Trineurone B
IUPAC Name:	2-[15-(1,3-benzodioxol-5-yl)-1-hydroxypentadecylidene]cyclohexane-1,3-dione
Synonyms:
Standard InCHIKey:	HAYFSZWIUKOZGT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H40O5/c29-23(28-24(30)16-13-17-25(28)31)15-12-10-8-6-4-2-1-3-5-7-9-11-14-22-18-19-26-27(20-22)33-21-32-26/h18-20,29H,1-17,21H2
SMILES:	C1CC(=O)C(=C(CCCCCCCCCCCCCCC2=CC3=C(C=C2)OCO3)O)C(=O)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	102339097
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO33674	Peperomia trineura	Species	Piperaceae	Eukaryota	aerial parts	Encantado, Rio Grande do Sul, Brazil	2006-DEC	PMID[24905499]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	Activity	=	5	ug	PMID[24905499]
NPT488	Organism	Cladosporium sphaerospermum	Cladosporium sphaerospermum	Activity	=	5	ug	PMID[24905499]

☑ 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 NPC477705 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	315
0.1-0.2	1451
0.2-0.3	3884
0.3-0.4	10045
0.4-0.5	8559
0.5-0.6	4384
0.6-0.7	11154
0.7-0.8	2739
0.8-0.85	138
0.85-0.9	24
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477694
0.9919	High Similarity	NPC477706
0.9318	High Similarity	NPC470855
0.9037	High Similarity	NPC104956
0.8984	High Similarity	NPC64948
0.8963	High Similarity	NPC28398
0.8889	High Similarity	NPC256167
0.8768	High Similarity	NPC46880
0.8741	High Similarity	NPC231719
0.8741	High Similarity	NPC52968
0.8705	High Similarity	NPC327052
0.8702	High Similarity	NPC304622
0.8692	High Similarity	NPC286683
0.8672	High Similarity	NPC163083
0.8643	High Similarity	NPC472560
0.8643	High Similarity	NPC189054
0.8636	High Similarity	NPC172673
0.8615	High Similarity	NPC92207
0.8615	High Similarity	NPC84076
0.8615	High Similarity	NPC127937
0.8615	High Similarity	NPC303680
0.8615	High Similarity	NPC90128
0.8582	High Similarity	NPC476336
0.8561	High Similarity	NPC472564
0.8551	High Similarity	NPC323601
0.855	High Similarity	NPC123722
0.855	High Similarity	NPC151167
0.855	High Similarity	NPC276466
0.855	High Similarity	NPC5018
0.855	High Similarity	NPC123228
0.8538	High Similarity	NPC257589
0.8538	High Similarity	NPC53305
0.8529	High Similarity	NPC230968
0.8529	High Similarity	NPC102260
0.8527	High Similarity	NPC244876
0.8527	High Similarity	NPC4181
0.8527	High Similarity	NPC164778
0.8527	High Similarity	NPC257976
0.8527	High Similarity	NPC242372
0.8516	High Similarity	NPC201777
0.8507	High Similarity	NPC239302
0.8492	Intermediate Similarity	NPC205502
0.8473	Intermediate Similarity	NPC179777
0.8462	Intermediate Similarity	NPC273686
0.8462	Intermediate Similarity	NPC312404
0.8451	Intermediate Similarity	NPC88345
0.845	Intermediate Similarity	NPC114298
0.8444	Intermediate Similarity	NPC327410
0.8444	Intermediate Similarity	NPC205915
0.8438	Intermediate Similarity	NPC158949
0.8429	Intermediate Similarity	NPC125134
0.8429	Intermediate Similarity	NPC86455
0.8429	Intermediate Similarity	NPC137920
0.8425	Intermediate Similarity	NPC69670
0.8425	Intermediate Similarity	NPC57501
0.8417	Intermediate Similarity	NPC282291
0.8417	Intermediate Similarity	NPC166137
0.8417	Intermediate Similarity	NPC51681
0.8403	Intermediate Similarity	NPC12854
0.8397	Intermediate Similarity	NPC85830
0.8394	Intermediate Similarity	NPC90431
0.8385	Intermediate Similarity	NPC249788
0.8382	Intermediate Similarity	NPC45404
0.8382	Intermediate Similarity	NPC19890
0.8382	Intermediate Similarity	NPC110958
0.8369	Intermediate Similarity	NPC15743
0.8359	Intermediate Similarity	NPC344161
0.8357	Intermediate Similarity	NPC52664
0.8346	Intermediate Similarity	NPC226661
0.8345	Intermediate Similarity	NPC234152
0.8333	Intermediate Similarity	NPC213711
0.8333	Intermediate Similarity	NPC40352
0.8333	Intermediate Similarity	NPC274356
0.8333	Intermediate Similarity	NPC268317
0.8333	Intermediate Similarity	NPC166184
0.8322	Intermediate Similarity	NPC25496
0.8308	Intermediate Similarity	NPC286573
0.8299	Intermediate Similarity	NPC476364
0.8293	Intermediate Similarity	NPC31279
0.8281	Intermediate Similarity	NPC299406
0.8276	Intermediate Similarity	NPC177830
0.8271	Intermediate Similarity	NPC223807
0.8271	Intermediate Similarity	NPC293641
0.8271	Intermediate Similarity	NPC20287
0.8271	Intermediate Similarity	NPC12022
0.8271	Intermediate Similarity	NPC20404
0.8268	Intermediate Similarity	NPC185738
0.8268	Intermediate Similarity	NPC199209
0.8268	Intermediate Similarity	NPC212643
0.8258	Intermediate Similarity	NPC280767
0.8258	Intermediate Similarity	NPC120066
0.8258	Intermediate Similarity	NPC3221
0.8248	Intermediate Similarity	NPC176814
0.8248	Intermediate Similarity	NPC4982
0.8248	Intermediate Similarity	NPC5310
0.8248	Intermediate Similarity	NPC68779
0.8248	Intermediate Similarity	NPC300776
0.8244	Intermediate Similarity	NPC18984
0.8244	Intermediate Similarity	NPC106659
0.8244	Intermediate Similarity	NPC229084
0.8244	Intermediate Similarity	NPC474691
0.8244	Intermediate Similarity	NPC160900
0.8235	Intermediate Similarity	NPC153453
0.8231	Intermediate Similarity	NPC114845
0.8231	Intermediate Similarity	NPC177291
0.8231	Intermediate Similarity	NPC301641
0.8231	Intermediate Similarity	NPC194416
0.8231	Intermediate Similarity	NPC80241
0.8222	Intermediate Similarity	NPC137427
0.8222	Intermediate Similarity	NPC66905
0.8222	Intermediate Similarity	NPC319282
0.8222	Intermediate Similarity	NPC123196
0.8222	Intermediate Similarity	NPC215941
0.8222	Intermediate Similarity	NPC65935
0.8222	Intermediate Similarity	NPC244246
0.8222	Intermediate Similarity	NPC311419
0.8222	Intermediate Similarity	NPC275724
0.8214	Intermediate Similarity	NPC474784
0.8209	Intermediate Similarity	NPC278308
0.8207	Intermediate Similarity	NPC472567
0.8195	Intermediate Similarity	NPC276014
0.8194	Intermediate Similarity	NPC153620
0.8194	Intermediate Similarity	NPC24257
0.8189	Intermediate Similarity	NPC111225
0.8188	Intermediate Similarity	NPC204592
0.8154	Intermediate Similarity	NPC225245
0.8151	Intermediate Similarity	NPC475170
0.8151	Intermediate Similarity	NPC37220
0.8148	Intermediate Similarity	NPC241354
0.8143	Intermediate Similarity	NPC318575
0.8143	Intermediate Similarity	NPC284409
0.8134	Intermediate Similarity	NPC32163
0.8134	Intermediate Similarity	NPC16651
0.8125	Intermediate Similarity	NPC296575
0.8125	Intermediate Similarity	NPC280001
0.8125	Intermediate Similarity	NPC3982
0.8116	Intermediate Similarity	NPC471110
0.8116	Intermediate Similarity	NPC37065
0.8108	Intermediate Similarity	NPC104728
0.8108	Intermediate Similarity	NPC35544
0.8099	Intermediate Similarity	NPC472410
0.8095	Intermediate Similarity	NPC163002
0.8092	Intermediate Similarity	NPC193484
0.8088	Intermediate Similarity	NPC134764
0.8088	Intermediate Similarity	NPC233961
0.8088	Intermediate Similarity	NPC339621
0.8088	Intermediate Similarity	NPC171550
0.8088	Intermediate Similarity	NPC280399
0.8088	Intermediate Similarity	NPC184814
0.8088	Intermediate Similarity	NPC275950
0.8088	Intermediate Similarity	NPC63574
0.8085	Intermediate Similarity	NPC322021
0.8079	Intermediate Similarity	NPC472565
0.8079	Intermediate Similarity	NPC68619
0.8067	Intermediate Similarity	NPC261090
0.8065	Intermediate Similarity	NPC127326
0.8058	Intermediate Similarity	NPC477301
0.8056	Intermediate Similarity	NPC229787
0.8056	Intermediate Similarity	NPC474158
0.8043	Intermediate Similarity	NPC475468
0.8029	Intermediate Similarity	NPC476345
0.8028	Intermediate Similarity	NPC218092
0.8028	Intermediate Similarity	NPC246474
0.8028	Intermediate Similarity	NPC162851
0.8026	Intermediate Similarity	NPC218471
0.8026	Intermediate Similarity	NPC239818
0.8026	Intermediate Similarity	NPC476337
0.8015	Intermediate Similarity	NPC60962
0.8015	Intermediate Similarity	NPC269843
0.8015	Intermediate Similarity	NPC476748
0.8015	Intermediate Similarity	NPC224814
0.8015	Intermediate Similarity	NPC189844
0.8015	Intermediate Similarity	NPC14007
0.8015	Intermediate Similarity	NPC109083
0.8014	Intermediate Similarity	NPC304821
0.8014	Intermediate Similarity	NPC178290
0.8013	Intermediate Similarity	NPC474990
0.8	Intermediate Similarity	NPC476363
0.8	Intermediate Similarity	NPC30890
0.8	Intermediate Similarity	NPC281020
0.8	Intermediate Similarity	NPC224687
0.7987	Intermediate Similarity	NPC308555
0.7986	Intermediate Similarity	NPC469978
0.7985	Intermediate Similarity	NPC173608
0.7985	Intermediate Similarity	NPC17348
0.7973	Intermediate Similarity	NPC32079
0.7972	Intermediate Similarity	NPC176586
0.7972	Intermediate Similarity	NPC210354
0.7971	Intermediate Similarity	NPC104077
0.7971	Intermediate Similarity	NPC50763
0.7971	Intermediate Similarity	NPC147616
0.7971	Intermediate Similarity	NPC106739
0.7971	Intermediate Similarity	NPC97316
0.7971	Intermediate Similarity	NPC259742
0.7971	Intermediate Similarity	NPC219671
0.7971	Intermediate Similarity	NPC227002
0.7971	Intermediate Similarity	NPC471505
0.797	Intermediate Similarity	NPC473942
0.7961	Intermediate Similarity	NPC475095
0.7959	Intermediate Similarity	NPC145569

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 NPC477705 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	903
0.2-0.3	1537
0.3-0.4	2652
0.4-0.5	1980
0.5-0.6	1168
0.6-0.7	577
0.7-0.8	49
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD6143	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD7028	Phase 2
0.8268	Intermediate Similarity	NPD5536	Phase 2
0.8244	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1357	Approved
0.782	Intermediate Similarity	NPD3705	Approved
0.7812	Intermediate Similarity	NPD5283	Phase 1
0.7737	Intermediate Similarity	NPD9494	Approved
0.7724	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4110	Phase 3
0.7656	Intermediate Similarity	NPD228	Approved
0.7632	Intermediate Similarity	NPD37	Approved
0.761	Intermediate Similarity	NPD3818	Discontinued
0.7538	Intermediate Similarity	NPD1241	Discontinued
0.7516	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD3972	Approved
0.7484	Intermediate Similarity	NPD4965	Approved
0.7484	Intermediate Similarity	NPD4966	Approved
0.7484	Intermediate Similarity	NPD4967	Phase 2
0.7483	Intermediate Similarity	NPD2492	Phase 1
0.7463	Intermediate Similarity	NPD1651	Approved
0.7434	Intermediate Similarity	NPD7458	Discontinued
0.7421	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6355	Discontinued
0.741	Intermediate Similarity	NPD2798	Approved
0.7391	Intermediate Similarity	NPD1876	Approved
0.7391	Intermediate Similarity	NPD1283	Approved
0.7389	Intermediate Similarity	NPD6234	Discontinued
0.7372	Intermediate Similarity	NPD3882	Suspended
0.7353	Intermediate Similarity	NPD3847	Discontinued
0.7329	Intermediate Similarity	NPD2935	Discontinued
0.7324	Intermediate Similarity	NPD6798	Discontinued
0.7301	Intermediate Similarity	NPD7074	Phase 3
0.7292	Intermediate Similarity	NPD1933	Approved
0.7292	Intermediate Similarity	NPD447	Suspended
0.729	Intermediate Similarity	NPD1934	Approved
0.7279	Intermediate Similarity	NPD4626	Approved
0.7259	Intermediate Similarity	NPD1894	Discontinued
0.7254	Intermediate Similarity	NPD7095	Approved
0.7254	Intermediate Similarity	NPD3027	Phase 3
0.7248	Intermediate Similarity	NPD8166	Discontinued
0.7248	Intermediate Similarity	NPD4628	Phase 3
0.7246	Intermediate Similarity	NPD1608	Approved
0.7244	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2801	Approved
0.7239	Intermediate Similarity	NPD7054	Approved
0.7209	Intermediate Similarity	NPD1358	Approved
0.7203	Intermediate Similarity	NPD3268	Approved
0.7197	Intermediate Similarity	NPD3817	Phase 2
0.7195	Intermediate Similarity	NPD7472	Approved
0.7174	Intermediate Similarity	NPD1281	Approved
0.7162	Intermediate Similarity	NPD2344	Approved
0.7154	Intermediate Similarity	NPD2684	Approved
0.7153	Intermediate Similarity	NPD6233	Phase 2
0.7153	Intermediate Similarity	NPD4062	Phase 3
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7134	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1511	Approved
0.7097	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2797	Approved
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8127	Discontinued
0.708	Intermediate Similarity	NPD5691	Approved
0.7073	Intermediate Similarity	NPD7228	Approved
0.7068	Intermediate Similarity	NPD7843	Approved
0.7067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7808	Phase 3
0.7066	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2614	Approved
0.705	Intermediate Similarity	NPD1535	Discovery
0.7048	Intermediate Similarity	NPD6797	Phase 2
0.7047	Intermediate Similarity	NPD7266	Discontinued
0.7044	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6232	Discontinued
0.7037	Intermediate Similarity	NPD7157	Approved
0.7034	Intermediate Similarity	NPD8032	Phase 2
0.7034	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1653	Approved
0.7029	Intermediate Similarity	NPD2932	Approved
0.7029	Intermediate Similarity	NPD17	Approved
0.7029	Intermediate Similarity	NPD1778	Approved
0.7027	Intermediate Similarity	NPD1510	Phase 2
0.7019	Intermediate Similarity	NPD5494	Approved
0.7013	Intermediate Similarity	NPD1512	Approved
0.7012	Intermediate Similarity	NPD7473	Discontinued
0.7006	Intermediate Similarity	NPD6873	Phase 2
0.7006	Intermediate Similarity	NPD7251	Discontinued
0.7006	Intermediate Similarity	NPD6385	Approved
0.7006	Intermediate Similarity	NPD7685	Pre-registration
0.7006	Intermediate Similarity	NPD6386	Approved
0.7	Intermediate Similarity	NPD5958	Discontinued
0.7	Intermediate Similarity	NPD2424	Discontinued
0.7	Intermediate Similarity	NPD1481	Phase 2
0.7	Intermediate Similarity	NPD3134	Approved
0.6994	Remote Similarity	NPD3926	Phase 2
0.6993	Remote Similarity	NPD4357	Discontinued
0.6986	Remote Similarity	NPD1240	Approved
0.6986	Remote Similarity	NPD3620	Phase 2
0.6986	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4060	Phase 1
0.6986	Remote Similarity	NPD2979	Phase 3
0.6981	Remote Similarity	NPD5977	Approved
0.6981	Remote Similarity	NPD5978	Approved
0.698	Remote Similarity	NPD2438	Suspended
0.6978	Remote Similarity	NPD3496	Discontinued
0.6974	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6190	Approved
0.6974	Remote Similarity	NPD2354	Approved
0.6974	Remote Similarity	NPD2309	Approved
0.6972	Remote Similarity	NPD3266	Approved
0.6972	Remote Similarity	NPD3267	Approved
0.697	Remote Similarity	NPD3022	Approved
0.697	Remote Similarity	NPD3021	Approved
0.6966	Remote Similarity	NPD2313	Discontinued
0.6966	Remote Similarity	NPD3764	Approved
0.6959	Remote Similarity	NPD7097	Phase 1
0.6957	Remote Similarity	NPD919	Approved
0.6951	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6166	Phase 2
0.695	Remote Similarity	NPD2982	Phase 2
0.695	Remote Similarity	NPD2983	Phase 2
0.6948	Remote Similarity	NPD3146	Approved
0.6948	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5535	Approved
0.6939	Remote Similarity	NPD230	Phase 1
0.6933	Remote Similarity	NPD1375	Discontinued
0.6928	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5647	Approved
0.6923	Remote Similarity	NPD7280	Phase 3
0.6923	Remote Similarity	NPD7281	Phase 3
0.6919	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3750	Approved
0.6906	Remote Similarity	NPD3019	Approved
0.6905	Remote Similarity	NPD6559	Discontinued
0.6905	Remote Similarity	NPD7240	Approved
0.6903	Remote Similarity	NPD6273	Approved
0.6892	Remote Similarity	NPD1607	Approved
0.6892	Remote Similarity	NPD6653	Approved
0.6887	Remote Similarity	NPD4534	Discontinued
0.6887	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9545	Approved
0.6883	Remote Similarity	NPD6799	Approved
0.6879	Remote Similarity	NPD2981	Phase 2
0.6875	Remote Similarity	NPD3018	Phase 2
0.6871	Remote Similarity	NPD943	Approved
0.6863	Remote Similarity	NPD3887	Approved
0.6859	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5110	Phase 2
0.6849	Remote Similarity	NPD5111	Phase 2
0.6849	Remote Similarity	NPD5109	Approved
0.6842	Remote Similarity	NPD4237	Approved
0.6842	Remote Similarity	NPD4236	Phase 3
0.6842	Remote Similarity	NPD6674	Discontinued
0.6839	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4739	Approved
0.6835	Remote Similarity	NPD4380	Phase 2
0.6835	Remote Similarity	NPD5585	Approved
0.6831	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5844	Phase 1
0.6821	Remote Similarity	NPD2353	Approved
0.6821	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2346	Discontinued
0.6813	Remote Similarity	NPD2978	Approved
0.6813	Remote Similarity	NPD8455	Phase 2
0.6813	Remote Similarity	NPD2977	Approved
0.6813	Remote Similarity	NPD7819	Suspended
0.6813	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1091	Approved
0.6809	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2674	Phase 3
0.68	Remote Similarity	NPD3748	Approved
0.6797	Remote Similarity	NPD7003	Approved
0.6797	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6671	Approved
0.6784	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3225	Approved
0.6783	Remote Similarity	NPD196	Phase 1
0.6781	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2653	Approved
0.6776	Remote Similarity	NPD1549	Phase 2
0.6772	Remote Similarity	NPD824	Approved
0.6772	Remote Similarity	NPD3455	Phase 2
0.6768	Remote Similarity	NPD2821	Approved
0.6768	Remote Similarity	NPD1247	Approved
0.6766	Remote Similarity	NPD3751	Discontinued
0.6761	Remote Similarity	NPD9717	Approved
0.6759	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3140	Approved

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