NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	422.16
Volume:	409.396
LogP:	-0.04
LogD:	0.811
LogS:	-1.489
# Rotatable Bonds:	7
TPSA:	134.91
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	4.974
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.918
MDCK Permeability:	1.7163421944133006e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.867
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.677
Plasma Protein Binding (PPB):	55.12638854980469%
Volume Distribution (VD):	0.982
Pgp-substrate:	40.48836898803711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.589
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.654
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.232
CYP2D6-inhibitor:	0.339
CYP2D6-substrate:	0.282
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.375

ADMET: Excretion

Clearance (CL):	7.14
Half-life (T1/2):	0.732

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.865
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.652
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.131
Carcinogencity:	0.247
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC476842

Natural Product ID:	NPC476842
*Common Name:**	(1S,3S,4R)-1-[(1S)-1,2-dihydroxyethyl]-3-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)-7,9-dimethoxy-2-oxaspiro[4.5]deca-6,9-dien-8-one
IUPAC Name:	(1S,3S,4R)-1-[(1S)-1,2-dihydroxyethyl]-3-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)-7,9-dimethoxy-2-oxaspiro[4.5]deca-6,9-dien-8-one
Synonyms:
Standard InCHIKey:	PKAFILSFKQEGRU-GREUMRBKSA-N
Standard InCHI:	InChI=1S/C21H26O9/c1-27-15-6-11(4-5-13(15)24)19-12(9-22)21(20(30-19)14(25)10-23)7-16(28-2)18(26)17(8-21)29-3/h4-8,12,14,19-20,22-25H,9-10H2,1-3H3/t12-,14+,19-,20-/m1/s1
SMILES:	COC1=C(C=CC(=C1)[C@@H]2[C@H](C3(C=C(C(=O)C(=C3)OC)OC)[C@H](O2)[C@H](CO)O)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122182031
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	stems	Wulai Hsiang, Taipei County, Taiwan	2005-MAY	PMID[17253858]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23025417]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	stem bark	Laifeng, Hubei Province, China	2012-JUL	PMID[26087384]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	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	1
Others	2

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	17900	nM	PMID[26087384]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	98	%	PMID[26087384]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	104	%	PMID[26087384]

☑ 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 NPC476842 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	352
0.1-0.2	1204
0.2-0.3	3218
0.3-0.4	7325
0.4-0.5	11354
0.5-0.6	4746
0.6-0.7	10003
0.7-0.8	4127
0.8-0.85	303
0.85-0.9	61
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476840
0.9638	High Similarity	NPC476843
0.9638	High Similarity	NPC476841
0.9	High Similarity	NPC322021
0.8897	High Similarity	NPC42300
0.8897	High Similarity	NPC174495
0.8897	High Similarity	NPC187998
0.8897	High Similarity	NPC257582
0.8897	High Similarity	NPC242807
0.8897	High Similarity	NPC77040
0.8897	High Similarity	NPC92164
0.8897	High Similarity	NPC145305
0.8897	High Similarity	NPC241522
0.8897	High Similarity	NPC64201
0.8897	High Similarity	NPC153739
0.8873	High Similarity	NPC67467
0.8865	High Similarity	NPC278076
0.8832	High Similarity	NPC277804
0.8824	High Similarity	NPC475875
0.8786	High Similarity	NPC471988
0.8777	High Similarity	NPC67247
0.8777	High Similarity	NPC135127
0.8759	High Similarity	NPC339621
0.8759	High Similarity	NPC233961
0.8759	High Similarity	NPC280399
0.875	High Similarity	NPC264706
0.875	High Similarity	NPC128208
0.875	High Similarity	NPC284881
0.875	High Similarity	NPC93433
0.875	High Similarity	NPC474444
0.875	High Similarity	NPC11258
0.875	High Similarity	NPC21867
0.875	High Similarity	NPC282703
0.875	High Similarity	NPC184733
0.875	High Similarity	NPC45774
0.875	High Similarity	NPC129570
0.875	High Similarity	NPC470084
0.8696	High Similarity	NPC7171
0.8696	High Similarity	NPC27843
0.8696	High Similarity	NPC161557
0.8696	High Similarity	NPC115207
0.8696	High Similarity	NPC158079
0.8696	High Similarity	NPC40432
0.8696	High Similarity	NPC228346
0.869	High Similarity	NPC163898
0.8676	High Similarity	NPC118533
0.8676	High Similarity	NPC165045
0.8643	High Similarity	NPC244983
0.8643	High Similarity	NPC287745
0.8643	High Similarity	NPC237594
0.8643	High Similarity	NPC476387
0.8643	High Similarity	NPC326095
0.8643	High Similarity	NPC249791
0.8643	High Similarity	NPC119060
0.8633	High Similarity	NPC181049
0.8633	High Similarity	NPC239302
0.8633	High Similarity	NPC4940
0.8633	High Similarity	NPC207400
0.8621	High Similarity	NPC50696
0.8603	High Similarity	NPC206882
0.86	High Similarity	NPC327225
0.8592	High Similarity	NPC281780
0.8571	High Similarity	NPC158331
0.8552	High Similarity	NPC474966
0.854	High Similarity	NPC5428
0.8531	High Similarity	NPC226005
0.8529	High Similarity	NPC148627
0.8521	High Similarity	NPC263367
0.8521	High Similarity	NPC10737
0.8521	High Similarity	NPC156502
0.8521	High Similarity	NPC177160
0.8521	High Similarity	NPC77861
0.8521	High Similarity	NPC54743
0.8521	High Similarity	NPC209985
0.8521	High Similarity	NPC477939
0.8521	High Similarity	NPC29799
0.8514	High Similarity	NPC98009
0.8514	High Similarity	NPC473408
0.8514	High Similarity	NPC102934
0.8514	High Similarity	NPC252402
0.8511	High Similarity	NPC145769
0.8507	High Similarity	NPC476343
0.8507	High Similarity	NPC470804
0.85	High Similarity	NPC18842
0.85	High Similarity	NPC175067
0.85	High Similarity	NPC204215
0.8489	Intermediate Similarity	NPC172673
0.8483	Intermediate Similarity	NPC131971
0.8478	Intermediate Similarity	NPC474178
0.8478	Intermediate Similarity	NPC252307
0.8478	Intermediate Similarity	NPC245826
0.8472	Intermediate Similarity	NPC288452
0.8472	Intermediate Similarity	NPC267291
0.8472	Intermediate Similarity	NPC289690
0.8472	Intermediate Similarity	NPC147379
0.8472	Intermediate Similarity	NPC144284
0.8467	Intermediate Similarity	NPC178048
0.8462	Intermediate Similarity	NPC126206
0.8451	Intermediate Similarity	NPC141765
0.8451	Intermediate Similarity	NPC101624
0.8451	Intermediate Similarity	NPC165155
0.8451	Intermediate Similarity	NPC214729
0.8451	Intermediate Similarity	NPC24490
0.8451	Intermediate Similarity	NPC99572
0.8451	Intermediate Similarity	NPC184938
0.8451	Intermediate Similarity	NPC34103
0.8451	Intermediate Similarity	NPC126409
0.8429	Intermediate Similarity	NPC474017
0.8414	Intermediate Similarity	NPC472711
0.8414	Intermediate Similarity	NPC100675
0.8411	Intermediate Similarity	NPC478268
0.8406	Intermediate Similarity	NPC292056
0.8406	Intermediate Similarity	NPC319625
0.8406	Intermediate Similarity	NPC183181
0.8406	Intermediate Similarity	NPC147821
0.8406	Intermediate Similarity	NPC118787
0.8406	Intermediate Similarity	NPC111247
0.8406	Intermediate Similarity	NPC41706
0.8406	Intermediate Similarity	NPC163332
0.8403	Intermediate Similarity	NPC474640
0.8403	Intermediate Similarity	NPC475757
0.8392	Intermediate Similarity	NPC471664
0.8392	Intermediate Similarity	NPC120852
0.8392	Intermediate Similarity	NPC157554
0.8392	Intermediate Similarity	NPC471665
0.8389	Intermediate Similarity	NPC236166
0.8387	Intermediate Similarity	NPC472962
0.8387	Intermediate Similarity	NPC472961
0.8382	Intermediate Similarity	NPC473451
0.8382	Intermediate Similarity	NPC471693
0.8382	Intermediate Similarity	NPC31344
0.8382	Intermediate Similarity	NPC317769
0.8382	Intermediate Similarity	NPC280704
0.838	Intermediate Similarity	NPC193026
0.838	Intermediate Similarity	NPC471942
0.838	Intermediate Similarity	NPC49603
0.838	Intermediate Similarity	NPC187616
0.838	Intermediate Similarity	NPC470881
0.8378	Intermediate Similarity	NPC472560
0.8369	Intermediate Similarity	NPC471505
0.8369	Intermediate Similarity	NPC106739
0.8358	Intermediate Similarity	NPC177475
0.8358	Intermediate Similarity	NPC148615
0.8358	Intermediate Similarity	NPC35071
0.8356	Intermediate Similarity	NPC193722
0.8356	Intermediate Similarity	NPC140502
0.8356	Intermediate Similarity	NPC476356
0.8356	Intermediate Similarity	NPC253481
0.8356	Intermediate Similarity	NPC278469
0.8356	Intermediate Similarity	NPC253722
0.8356	Intermediate Similarity	NPC31751
0.8355	Intermediate Similarity	NPC470769
0.8355	Intermediate Similarity	NPC44730
0.8345	Intermediate Similarity	NPC110313
0.8345	Intermediate Similarity	NPC55793
0.8333	Intermediate Similarity	NPC178284
0.8333	Intermediate Similarity	NPC58607
0.8333	Intermediate Similarity	NPC191037
0.8333	Intermediate Similarity	NPC166184
0.8322	Intermediate Similarity	NPC221383
0.8322	Intermediate Similarity	NPC299090
0.8322	Intermediate Similarity	NPC283081
0.8322	Intermediate Similarity	NPC143892
0.8322	Intermediate Similarity	NPC174191
0.8322	Intermediate Similarity	NPC93783
0.8322	Intermediate Similarity	NPC142547
0.8322	Intermediate Similarity	NPC135777
0.8322	Intermediate Similarity	NPC25496
0.831	Intermediate Similarity	NPC26394
0.831	Intermediate Similarity	NPC6836
0.8309	Intermediate Similarity	NPC85488
0.8309	Intermediate Similarity	NPC209567
0.8301	Intermediate Similarity	NPC25127
0.8301	Intermediate Similarity	NPC287504
0.8299	Intermediate Similarity	NPC477898
0.8299	Intermediate Similarity	NPC185307
0.8299	Intermediate Similarity	NPC470950
0.8298	Intermediate Similarity	NPC470095
0.8298	Intermediate Similarity	NPC470096
0.8298	Intermediate Similarity	NPC65942
0.8298	Intermediate Similarity	NPC248307
0.8298	Intermediate Similarity	NPC469480
0.8289	Intermediate Similarity	NPC267091
0.8289	Intermediate Similarity	NPC476434
0.8288	Intermediate Similarity	NPC83375
0.8288	Intermediate Similarity	NPC471414
0.8288	Intermediate Similarity	NPC263261
0.8288	Intermediate Similarity	NPC224876
0.8288	Intermediate Similarity	NPC87725
0.8288	Intermediate Similarity	NPC311530
0.8288	Intermediate Similarity	NPC470372
0.8286	Intermediate Similarity	NPC170844
0.8286	Intermediate Similarity	NPC86030
0.8286	Intermediate Similarity	NPC5851
0.8286	Intermediate Similarity	NPC476968
0.8284	Intermediate Similarity	NPC135961
0.8284	Intermediate Similarity	NPC24474
0.8284	Intermediate Similarity	NPC320987
0.8284	Intermediate Similarity	NPC311595
0.8284	Intermediate Similarity	NPC181969

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 NPC476842 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	795
0.2-0.3	1787
0.3-0.4	2671
0.4-0.5	1955
0.5-0.6	1067
0.6-0.7	535
0.7-0.8	57
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
0.8286	Intermediate Similarity	NPD3027	Phase 3
0.7986	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3620	Phase 2
0.7862	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3882	Suspended
0.7785	Intermediate Similarity	NPD7266	Discontinued
0.774	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1613	Approved
0.7697	Intermediate Similarity	NPD6190	Approved
0.7687	Intermediate Similarity	NPD228	Approved
0.7628	Intermediate Similarity	NPD1653	Approved
0.7626	Intermediate Similarity	NPD1357	Approved
0.7622	Intermediate Similarity	NPD6166	Phase 2
0.7622	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4060	Phase 1
0.7591	Intermediate Similarity	NPD7157	Approved
0.7589	Intermediate Similarity	NPD3705	Approved
0.7588	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5283	Phase 1
0.7547	Intermediate Similarity	NPD1934	Approved
0.7531	Intermediate Similarity	NPD6234	Discontinued
0.753	Intermediate Similarity	NPD3818	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7482	Intermediate Similarity	NPD5536	Phase 2
0.7466	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD8127	Discontinued
0.7438	Intermediate Similarity	NPD37	Approved
0.7434	Intermediate Similarity	NPD5763	Approved
0.7434	Intermediate Similarity	NPD5762	Approved
0.7415	Intermediate Similarity	NPD7095	Approved
0.7407	Intermediate Similarity	NPD4966	Approved
0.7407	Intermediate Similarity	NPD4965	Approved
0.7407	Intermediate Similarity	NPD4967	Phase 2
0.7403	Intermediate Similarity	NPD8166	Discontinued
0.7403	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4110	Phase 3
0.7397	Intermediate Similarity	NPD2861	Phase 2
0.7397	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD6355	Discontinued
0.7321	Intermediate Similarity	NPD7228	Approved
0.731	Intermediate Similarity	NPD8651	Approved
0.7301	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6797	Phase 2
0.7284	Intermediate Similarity	NPD2801	Approved
0.7279	Intermediate Similarity	NPD3021	Approved
0.7279	Intermediate Similarity	NPD3022	Approved
0.7279	Intermediate Similarity	NPD9494	Approved
0.7251	Intermediate Similarity	NPD7251	Discontinued
0.7251	Intermediate Similarity	NPD7685	Pre-registration
0.7248	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7843	Approved
0.7239	Intermediate Similarity	NPD2563	Approved
0.7239	Intermediate Similarity	NPD2560	Approved
0.7235	Intermediate Similarity	NPD7074	Phase 3
0.7226	Intermediate Similarity	NPD4237	Approved
0.7226	Intermediate Similarity	NPD4236	Phase 3
0.7219	Intermediate Similarity	NPD5735	Approved
0.7211	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7808	Phase 3
0.7209	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD2684	Approved
0.7205	Intermediate Similarity	NPD4380	Phase 2
0.7205	Intermediate Similarity	NPD7028	Phase 2
0.7193	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7054	Approved
0.7171	Intermediate Similarity	NPD6653	Approved
0.717	Intermediate Similarity	NPD1512	Approved
0.7169	Intermediate Similarity	NPD5494	Approved
0.7161	Intermediate Similarity	NPD2424	Discontinued
0.7152	Intermediate Similarity	NPD7075	Discontinued
0.7152	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD3094	Phase 2
0.7135	Intermediate Similarity	NPD7472	Approved
0.7126	Intermediate Similarity	NPD7199	Phase 2
0.7125	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2983	Phase 2
0.7123	Intermediate Similarity	NPD2982	Phase 2
0.7115	Intermediate Similarity	NPD6674	Discontinued
0.7114	Intermediate Similarity	NPD4908	Phase 1
0.7105	Intermediate Similarity	NPD4340	Discontinued
0.7105	Intermediate Similarity	NPD230	Phase 1
0.7101	Intermediate Similarity	NPD27	Approved
0.7101	Intermediate Similarity	NPD2489	Approved
0.7099	Intermediate Similarity	NPD6599	Discontinued
0.7086	Intermediate Similarity	NPD6233	Phase 2
0.7081	Intermediate Similarity	NPD3687	Approved
0.7081	Intermediate Similarity	NPD3686	Approved
0.707	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5090	Approved
0.7055	Intermediate Similarity	NPD5089	Approved
0.7055	Intermediate Similarity	NPD2981	Phase 2
0.7047	Intermediate Similarity	NPD3018	Phase 2
0.7044	Intermediate Similarity	NPD4357	Discontinued
0.7044	Intermediate Similarity	NPD1511	Approved
0.7041	Intermediate Similarity	NPD2970	Approved
0.7041	Intermediate Similarity	NPD2969	Approved
0.7039	Intermediate Similarity	NPD1558	Phase 1
0.7034	Intermediate Similarity	NPD3496	Discontinued
0.703	Intermediate Similarity	NPD5402	Approved
0.702	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6798	Discontinued
0.7012	Intermediate Similarity	NPD6801	Discontinued
0.7007	Intermediate Similarity	NPD4749	Approved
0.7007	Intermediate Similarity	NPD1358	Approved
0.7006	Intermediate Similarity	NPD3060	Approved
0.7006	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3657	Discovery
0.6987	Remote Similarity	NPD1375	Discontinued
0.6986	Remote Similarity	NPD1091	Approved
0.6986	Remote Similarity	NPD3092	Approved
0.6986	Remote Similarity	NPD1610	Phase 2
0.6982	Remote Similarity	NPD6071	Discontinued
0.6977	Remote Similarity	NPD5844	Phase 1
0.6971	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7313	Approved
0.6971	Remote Similarity	NPD7310	Approved
0.6971	Remote Similarity	NPD7312	Approved
0.6971	Remote Similarity	NPD7311	Approved
0.697	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2977	Approved
0.697	Remote Similarity	NPD2978	Approved
0.6968	Remote Similarity	NPD5588	Approved
0.6966	Remote Similarity	NPD4626	Approved
0.6966	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7473	Discontinued
0.6959	Remote Similarity	NPD6696	Suspended
0.6957	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7526	Approved
0.6957	Remote Similarity	NPD52	Approved
0.6957	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6559	Discontinued
0.6946	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4534	Discontinued
0.6941	Remote Similarity	NPD3926	Phase 2
0.6937	Remote Similarity	NPD6799	Approved
0.6934	Remote Similarity	NPD3134	Approved
0.6933	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7309	Approved
0.6928	Remote Similarity	NPD2238	Phase 2
0.6927	Remote Similarity	NPD2490	Approved
0.6927	Remote Similarity	NPD2488	Approved
0.6923	Remote Similarity	NPD2161	Phase 2
0.6923	Remote Similarity	NPD1247	Approved
0.6919	Remote Similarity	NPD3751	Discontinued
0.6914	Remote Similarity	NPD5403	Approved
0.6905	Remote Similarity	NPD919	Approved
0.6903	Remote Similarity	NPD4538	Approved
0.6903	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4536	Approved
0.6901	Remote Similarity	NPD2898	Approved
0.6899	Remote Similarity	NPD1652	Phase 2
0.6897	Remote Similarity	NPD5691	Approved
0.6894	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5327	Phase 3
0.6884	Remote Similarity	NPD290	Approved
0.6883	Remote Similarity	NPD5124	Phase 1
0.6883	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6232	Discontinued
0.6882	Remote Similarity	NPD3051	Approved
0.6879	Remote Similarity	NPD6004	Phase 3
0.6879	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6002	Phase 3
0.6879	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6005	Phase 3
0.6875	Remote Similarity	NPD5058	Phase 3
0.6871	Remote Similarity	NPD422	Phase 1
0.6867	Remote Similarity	NPD5772	Approved
0.6867	Remote Similarity	NPD1465	Phase 2
0.6867	Remote Similarity	NPD5773	Approved
0.6865	Remote Similarity	NPD2493	Approved
0.6865	Remote Similarity	NPD2494	Approved
0.6863	Remote Similarity	NPD4062	Phase 3
0.6863	Remote Similarity	NPD2674	Phase 3
0.6857	Remote Similarity	NPD7240	Approved
0.6855	Remote Similarity	NPD6331	Phase 2
0.6854	Remote Similarity	NPD4663	Approved
0.6853	Remote Similarity	NPD6671	Approved
0.6852	Remote Similarity	NPD6273	Approved
0.6845	Remote Similarity	NPD4583	Approved
0.6845	Remote Similarity	NPD4582	Approved
0.6835	Remote Similarity	NPD5958	Discontinued
0.6831	Remote Similarity	NPD1241	Discontinued
0.6828	Remote Similarity	NPD3091	Approved
0.6828	Remote Similarity	NPD3057	Approved
0.6826	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2163	Approved
0.6816	Remote Similarity	NPD7906	Approved
0.6815	Remote Similarity	NPD6100	Approved
0.6815	Remote Similarity	NPD6099	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