NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	452.17
Volume:	435.482
LogP:	-0.041
LogD:	0.262
LogS:	-1.625
# Rotatable Bonds:	8
TPSA:	144.14
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	4.995
Fsp3:	0.5
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:	-5.119
MDCK Permeability:	2.3575625164085068e-05
Pgp-inhibitor:	0.181
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.096
20% Bioavailability (F20%):	0.904
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.859
Plasma Protein Binding (PPB):	43.119659423828125%
Volume Distribution (VD):	1.163
Pgp-substrate:	34.859066009521484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.602
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.282
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.255
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.354

ADMET: Excretion

Clearance (CL):	5.374
Half-life (T1/2):	0.797

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.869
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.603
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.186
Carcinogencity:	0.058
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC476841

Natural Product ID:	NPC476841
*Common Name:**	(1R,3R,4S)-1-[(1R)-1,2-dihydroxyethyl]-3-(4-hydroxy-3,5-dimethoxyphenyl)-4-(hydroxymethyl)-7,9-dimethoxy-2-oxaspiro[4.5]deca-6,9-dien-8-one
IUPAC Name:	(1R,3R,4S)-1-[(1R)-1,2-dihydroxyethyl]-3-(4-hydroxy-3,5-dimethoxyphenyl)-4-(hydroxymethyl)-7,9-dimethoxy-2-oxaspiro[4.5]deca-6,9-dien-8-one
Synonyms:
Standard InCHIKey:	FVTPGXYESFNCMY-FKULMGGCSA-N
Standard InCHI:	InChI=1S/C22H28O10/c1-28-14-5-11(6-15(29-2)18(14)26)20-12(9-23)22(21(32-20)13(25)10-24)7-16(30-3)19(27)17(8-22)31-4/h5-8,12-13,20-21,23-26H,9-10H2,1-4H3/t12-,13+,20-,21-/m0/s1
SMILES:	COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H](C3(C=C(C(=O)C(=C3)OC)OC)[C@@H](O2)[C@@H](CO)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122182034
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	=	4300	nM	PMID[26087384]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	102	%	PMID[26087384]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	111	%	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 NPC476841 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	377
0.1-0.2	1259
0.2-0.3	3395
0.3-0.4	7753
0.4-0.5	11061
0.5-0.6	4698
0.6-0.7	8923
0.7-0.8	4884
0.8-0.85	318
0.85-0.9	25
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476843
0.9638	High Similarity	NPC476840
0.9638	High Similarity	NPC476842
0.8993	High Similarity	NPC326095
0.8993	High Similarity	NPC244983
0.8857	High Similarity	NPC287745
0.8849	High Similarity	NPC175067
0.8849	High Similarity	NPC204215
0.8828	High Similarity	NPC50696
0.8794	High Similarity	NPC165155
0.8794	High Similarity	NPC141765
0.8794	High Similarity	NPC24490
0.8794	High Similarity	NPC34103
0.8786	High Similarity	NPC158331
0.8759	High Similarity	NPC474966
0.8723	High Similarity	NPC145769
0.8716	High Similarity	NPC473408
0.8716	High Similarity	NPC102934
0.8716	High Similarity	NPC252402
0.8681	High Similarity	NPC144284
0.8681	High Similarity	NPC267291
0.8681	High Similarity	NPC322021
0.8662	High Similarity	NPC126409
0.8662	High Similarity	NPC99572
0.8643	High Similarity	NPC474017
0.8621	High Similarity	NPC311530
0.8618	High Similarity	NPC287504
0.8581	High Similarity	NPC212890
0.8581	High Similarity	NPC472560
0.8571	High Similarity	NPC241522
0.8571	High Similarity	NPC174495
0.8571	High Similarity	NPC242807
0.8571	High Similarity	NPC92164
0.8571	High Similarity	NPC64201
0.8571	High Similarity	NPC187998
0.8571	High Similarity	NPC145305
0.8571	High Similarity	NPC153739
0.8571	High Similarity	NPC257582
0.8571	High Similarity	NPC77040
0.8571	High Similarity	NPC42300
0.8562	High Similarity	NPC278469
0.8562	High Similarity	NPC67467
0.8562	High Similarity	NPC193722
0.8553	High Similarity	NPC470769
0.8552	High Similarity	NPC278076
0.8542	High Similarity	NPC474039
0.8514	High Similarity	NPC477702
0.8511	High Similarity	NPC277804
0.8511	High Similarity	NPC470096
0.8511	High Similarity	NPC470095
0.85	High Similarity	NPC475875
0.85	High Similarity	NPC170844
0.85	High Similarity	NPC476968
0.8497	Intermediate Similarity	NPC25127
0.8493	Intermediate Similarity	NPC224876
0.8493	Intermediate Similarity	NPC83375
0.8493	Intermediate Similarity	NPC87725
0.8493	Intermediate Similarity	NPC263261
0.8487	Intermediate Similarity	NPC476434
0.8477	Intermediate Similarity	NPC177830
0.8472	Intermediate Similarity	NPC471988
0.8467	Intermediate Similarity	NPC165375
0.8467	Intermediate Similarity	NPC220598
0.8462	Intermediate Similarity	NPC67247
0.8462	Intermediate Similarity	NPC135127
0.8451	Intermediate Similarity	NPC35932
0.8451	Intermediate Similarity	NPC160991
0.8451	Intermediate Similarity	NPC184447
0.8451	Intermediate Similarity	NPC7903
0.8451	Intermediate Similarity	NPC201587
0.8451	Intermediate Similarity	NPC16208
0.8451	Intermediate Similarity	NPC253105
0.8446	Intermediate Similarity	NPC474444
0.8446	Intermediate Similarity	NPC118385
0.8446	Intermediate Similarity	NPC297342
0.8446	Intermediate Similarity	NPC472712
0.8446	Intermediate Similarity	NPC264706
0.8446	Intermediate Similarity	NPC187774
0.8446	Intermediate Similarity	NPC114119
0.8446	Intermediate Similarity	NPC472713
0.8446	Intermediate Similarity	NPC471415
0.8446	Intermediate Similarity	NPC473046
0.8446	Intermediate Similarity	NPC284881
0.8446	Intermediate Similarity	NPC93433
0.8446	Intermediate Similarity	NPC470097
0.844	Intermediate Similarity	NPC339621
0.844	Intermediate Similarity	NPC280399
0.844	Intermediate Similarity	NPC233961
0.8431	Intermediate Similarity	NPC327225
0.8429	Intermediate Similarity	NPC186843
0.8429	Intermediate Similarity	NPC470213
0.8429	Intermediate Similarity	NPC98631
0.8429	Intermediate Similarity	NPC129570
0.8429	Intermediate Similarity	NPC11258
0.8429	Intermediate Similarity	NPC206615
0.8429	Intermediate Similarity	NPC45774
0.8429	Intermediate Similarity	NPC184733
0.8429	Intermediate Similarity	NPC128208
0.8429	Intermediate Similarity	NPC282703
0.8429	Intermediate Similarity	NPC470084
0.8429	Intermediate Similarity	NPC21867
0.8425	Intermediate Similarity	NPC309124
0.8425	Intermediate Similarity	NPC254759
0.8425	Intermediate Similarity	NPC184797
0.8425	Intermediate Similarity	NPC160283
0.8425	Intermediate Similarity	NPC177868
0.8425	Intermediate Similarity	NPC291101
0.8425	Intermediate Similarity	NPC266197
0.8417	Intermediate Similarity	NPC76451
0.8411	Intermediate Similarity	NPC474393
0.8411	Intermediate Similarity	NPC474347
0.84	Intermediate Similarity	NPC30720
0.8389	Intermediate Similarity	NPC474982
0.8389	Intermediate Similarity	NPC163898
0.838	Intermediate Similarity	NPC7171
0.838	Intermediate Similarity	NPC472597
0.838	Intermediate Similarity	NPC158079
0.838	Intermediate Similarity	NPC228346
0.838	Intermediate Similarity	NPC40432
0.838	Intermediate Similarity	NPC309787
0.838	Intermediate Similarity	NPC115207
0.838	Intermediate Similarity	NPC161557
0.838	Intermediate Similarity	NPC27843
0.8378	Intermediate Similarity	NPC470811
0.8378	Intermediate Similarity	NPC477696
0.8378	Intermediate Similarity	NPC12728
0.8378	Intermediate Similarity	NPC185071
0.8378	Intermediate Similarity	NPC477616
0.8378	Intermediate Similarity	NPC477697
0.8369	Intermediate Similarity	NPC48315
0.8367	Intermediate Similarity	NPC247291
0.8366	Intermediate Similarity	NPC95498
0.8366	Intermediate Similarity	NPC246566
0.8366	Intermediate Similarity	NPC151425
0.8357	Intermediate Similarity	NPC165045
0.8357	Intermediate Similarity	NPC118533
0.8357	Intermediate Similarity	NPC127587
0.8356	Intermediate Similarity	NPC473739
0.8356	Intermediate Similarity	NPC236306
0.8356	Intermediate Similarity	NPC292882
0.8356	Intermediate Similarity	NPC232164
0.8356	Intermediate Similarity	NPC22517
0.8355	Intermediate Similarity	NPC475170
0.8355	Intermediate Similarity	NPC241636
0.8355	Intermediate Similarity	NPC470916
0.8333	Intermediate Similarity	NPC310854
0.8333	Intermediate Similarity	NPC119060
0.8333	Intermediate Similarity	NPC249791
0.8333	Intermediate Similarity	NPC107478
0.8333	Intermediate Similarity	NPC260397
0.8333	Intermediate Similarity	NPC317053
0.8333	Intermediate Similarity	NPC476387
0.8333	Intermediate Similarity	NPC170694
0.8333	Intermediate Similarity	NPC474054
0.8333	Intermediate Similarity	NPC470827
0.8333	Intermediate Similarity	NPC238810
0.8333	Intermediate Similarity	NPC324492
0.8333	Intermediate Similarity	NPC474799
0.8333	Intermediate Similarity	NPC237594
0.8323	Intermediate Similarity	NPC117154
0.8323	Intermediate Similarity	NPC476065
0.8322	Intermediate Similarity	NPC239302
0.8322	Intermediate Similarity	NPC470752
0.8322	Intermediate Similarity	NPC181049
0.8322	Intermediate Similarity	NPC4940
0.8322	Intermediate Similarity	NPC87883
0.8322	Intermediate Similarity	NPC18842
0.8322	Intermediate Similarity	NPC207400
0.8321	Intermediate Similarity	NPC49341
0.8312	Intermediate Similarity	NPC149735
0.8311	Intermediate Similarity	NPC46180
0.8311	Intermediate Similarity	NPC472714
0.8311	Intermediate Similarity	NPC5262
0.8311	Intermediate Similarity	NPC107161
0.8311	Intermediate Similarity	NPC287124
0.831	Intermediate Similarity	NPC469612
0.831	Intermediate Similarity	NPC472338
0.831	Intermediate Similarity	NPC469614
0.8302	Intermediate Similarity	NPC476822
0.8301	Intermediate Similarity	NPC62354
0.8298	Intermediate Similarity	NPC328682
0.8298	Intermediate Similarity	NPC109275
0.8298	Intermediate Similarity	NPC54321
0.8298	Intermediate Similarity	NPC281864
0.8289	Intermediate Similarity	NPC125570
0.8288	Intermediate Similarity	NPC46277
0.8288	Intermediate Similarity	NPC156948
0.8288	Intermediate Similarity	NPC477938
0.8288	Intermediate Similarity	NPC3072
0.8288	Intermediate Similarity	NPC86605
0.8288	Intermediate Similarity	NPC281780
0.8288	Intermediate Similarity	NPC301765
0.8286	Intermediate Similarity	NPC9891
0.8286	Intermediate Similarity	NPC50683
0.8286	Intermediate Similarity	NPC206882
0.8286	Intermediate Similarity	NPC285725
0.8286	Intermediate Similarity	NPC112571
0.8286	Intermediate Similarity	NPC88297
0.8286	Intermediate Similarity	NPC186845
0.828	Intermediate Similarity	NPC470828

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 NPC476841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	842
0.2-0.3	1939
0.3-0.4	2764
0.4-0.5	1819
0.5-0.6	1002
0.6-0.7	421
0.7-0.8	61
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.85	High Similarity	NPD3027	Phase 3
0.8038	Intermediate Similarity	NPD3882	Suspended
0.7945	Intermediate Similarity	NPD1613	Approved
0.7945	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6234	Discontinued
0.7821	Intermediate Similarity	NPD1653	Approved
0.7805	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6166	Phase 2
0.7805	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD37	Approved
0.7736	Intermediate Similarity	NPD1934	Approved
0.7724	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3818	Discontinued
0.7703	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD3620	Phase 2
0.7702	Intermediate Similarity	NPD4966	Approved
0.7702	Intermediate Similarity	NPD4967	Phase 2
0.7702	Intermediate Similarity	NPD4965	Approved
0.7692	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7228	Approved
0.7593	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6190	Approved
0.7534	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3817	Phase 2
0.7516	Intermediate Similarity	NPD7266	Discontinued
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2801	Approved
0.7457	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3705	Approved
0.7427	Intermediate Similarity	NPD7251	Discontinued
0.7425	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD230	Phase 1
0.7412	Intermediate Similarity	NPD7074	Phase 3
0.7391	Intermediate Similarity	NPD228	Approved
0.7391	Intermediate Similarity	NPD4380	Phase 2
0.7384	Intermediate Similarity	NPD7808	Phase 3
0.7384	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1512	Approved
0.7353	Intermediate Similarity	NPD7054	Approved
0.7351	Intermediate Similarity	NPD4060	Phase 1
0.7349	Intermediate Similarity	NPD5494	Approved
0.7346	Intermediate Similarity	NPD5090	Approved
0.7346	Intermediate Similarity	NPD5089	Approved
0.7343	Intermediate Similarity	NPD1357	Approved
0.7333	Intermediate Similarity	NPD7075	Discontinued
0.7329	Intermediate Similarity	NPD2983	Phase 2
0.7329	Intermediate Similarity	NPD2982	Phase 2
0.7329	Intermediate Similarity	NPD4749	Approved
0.7315	Intermediate Similarity	NPD4908	Phase 1
0.7312	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7472	Approved
0.7305	Intermediate Similarity	NPD7157	Approved
0.7305	Intermediate Similarity	NPD7199	Phase 2
0.7286	Intermediate Similarity	NPD5283	Phase 1
0.7284	Intermediate Similarity	NPD6599	Discontinued
0.7261	Intermediate Similarity	NPD4628	Phase 3
0.726	Intermediate Similarity	NPD2981	Phase 2
0.7248	Intermediate Similarity	NPD3018	Phase 2
0.7233	Intermediate Similarity	NPD4357	Discontinued
0.7233	Intermediate Similarity	NPD1511	Approved
0.7219	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5402	Approved
0.7203	Intermediate Similarity	NPD5536	Phase 2
0.7202	Intermediate Similarity	NPD8127	Discontinued
0.7195	Intermediate Similarity	NPD6801	Discontinued
0.7192	Intermediate Similarity	NPD1610	Phase 2
0.7179	Intermediate Similarity	NPD5763	Approved
0.7179	Intermediate Similarity	NPD5762	Approved
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD1465	Phase 2
0.7152	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD4110	Phase 3
0.7151	Intermediate Similarity	NPD5844	Phase 1
0.7135	Intermediate Similarity	NPD7473	Discontinued
0.7133	Intermediate Similarity	NPD2861	Phase 2
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.7126	Intermediate Similarity	NPD7240	Approved
0.7126	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6799	Approved
0.7125	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3926	Phase 2
0.7115	Intermediate Similarity	NPD6099	Approved
0.7115	Intermediate Similarity	NPD6100	Approved
0.7108	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1247	Approved
0.7099	Intermediate Similarity	NPD5403	Approved
0.7097	Intermediate Similarity	NPD6111	Discontinued
0.7089	Intermediate Similarity	NPD1652	Phase 2
0.7089	Intermediate Similarity	NPD2800	Approved
0.7083	Intermediate Similarity	NPD919	Approved
0.7081	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6355	Discontinued
0.7078	Intermediate Similarity	NPD5124	Phase 1
0.7075	Intermediate Similarity	NPD422	Phase 1
0.7059	Intermediate Similarity	NPD6232	Discontinued
0.7052	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4585	Approved
0.7047	Intermediate Similarity	NPD8651	Approved
0.7029	Intermediate Similarity	NPD7685	Pre-registration
0.7025	Intermediate Similarity	NPD2424	Discontinued
0.7025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8434	Phase 2
0.702	Intermediate Similarity	NPD9494	Approved
0.7012	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2560	Approved
0.7006	Intermediate Similarity	NPD2563	Approved
0.7	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3021	Approved
0.7	Intermediate Similarity	NPD2219	Phase 1
0.7	Intermediate Similarity	NPD3022	Approved
0.6994	Remote Similarity	NPD3751	Discontinued
0.6983	Remote Similarity	NPD6842	Approved
0.6983	Remote Similarity	NPD6841	Approved
0.6983	Remote Similarity	NPD6843	Phase 3
0.6981	Remote Similarity	NPD4237	Approved
0.6981	Remote Similarity	NPD4236	Phase 3
0.6981	Remote Similarity	NPD6674	Discontinued
0.6975	Remote Similarity	NPD2532	Approved
0.6975	Remote Similarity	NPD2534	Approved
0.6975	Remote Similarity	NPD2533	Approved
0.6975	Remote Similarity	NPD5401	Approved
0.6972	Remote Similarity	NPD7843	Approved
0.697	Remote Similarity	NPD7028	Phase 2
0.6968	Remote Similarity	NPD5735	Approved
0.6957	Remote Similarity	NPD7124	Phase 2
0.6943	Remote Similarity	NPD1510	Phase 2
0.6937	Remote Similarity	NPD3750	Approved
0.6929	Remote Similarity	NPD2684	Approved
0.6923	Remote Similarity	NPD6651	Approved
0.6923	Remote Similarity	NPD6653	Approved
0.6923	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1549	Phase 2
0.6918	Remote Similarity	NPD1548	Phase 1
0.6914	Remote Similarity	NPD5297	Approved
0.691	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4005	Discontinued
0.6905	Remote Similarity	NPD5353	Approved
0.6905	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1240	Approved
0.6903	Remote Similarity	NPD4140	Approved
0.6893	Remote Similarity	NPD7549	Discontinued
0.6887	Remote Similarity	NPD3094	Phase 2
0.6879	Remote Similarity	NPD4750	Phase 3
0.6879	Remote Similarity	NPD2489	Approved
0.6879	Remote Similarity	NPD27	Approved
0.6859	Remote Similarity	NPD3657	Discovery
0.6859	Remote Similarity	NPD4340	Discontinued
0.6855	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3687	Approved
0.6848	Remote Similarity	NPD3686	Approved
0.6846	Remote Similarity	NPD1091	Approved
0.6845	Remote Similarity	NPD7819	Suspended
0.6839	Remote Similarity	NPD6233	Phase 2
0.6835	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2970	Approved
0.6821	Remote Similarity	NPD2969	Approved
0.6821	Remote Similarity	NPD6696	Suspended
0.6818	Remote Similarity	NPD4625	Phase 3
0.6815	Remote Similarity	NPD1607	Approved
0.6802	Remote Similarity	NPD6959	Discontinued
0.6795	Remote Similarity	NPD1558	Phase 1
0.6795	Remote Similarity	NPD2238	Phase 2
0.6795	Remote Similarity	NPD943	Approved
0.6792	Remote Similarity	NPD2796	Approved
0.6779	Remote Similarity	NPD3496	Discontinued
0.6774	Remote Similarity	NPD6798	Discontinued
0.6774	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3060	Approved
0.6768	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4678	Approved
0.6766	Remote Similarity	NPD4675	Approved
0.6763	Remote Similarity	NPD6071	Discontinued
0.6763	Remote Similarity	NPD3787	Discontinued
0.676	Remote Similarity	NPD7312	Approved
0.676	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7311	Approved
0.676	Remote Similarity	NPD7310	Approved
0.676	Remote Similarity	NPD7313	Approved
0.6758	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2494	Approved
0.6755	Remote Similarity	NPD2493	Approved
0.675	Remote Similarity	NPD3540	Phase 1
0.675	Remote Similarity	NPD1375	Discontinued
0.6746	Remote Similarity	NPD2977	Approved
0.6746	Remote Similarity	NPD2978	Approved
0.674	Remote Similarity	NPD4663	Approved
0.6738	Remote Similarity	NPD1358	Approved
0.6737	Remote Similarity	NPD4582	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