NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	358.695
LogP:	2.47
LogD:	2.924
LogS:	-3.678
# Rotatable Bonds:	3
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.787
Synthetic Accessibility Score:	4.643
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.826
MDCK Permeability:	2.2180684027262032e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.376
30% Bioavailability (F30%):	0.478

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.234
Plasma Protein Binding (PPB):	94.79535675048828%
Volume Distribution (VD):	1.101
Pgp-substrate:	5.934167385101318%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.554
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.231
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.236
CYP3A4-inhibitor:	0.24
CYP3A4-substrate:	0.397

ADMET: Excretion

Clearance (CL):	7.665
Half-life (T1/2):	0.438

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.127
Carcinogencity:	0.243
Eye Corrosion:	0.017
Eye Irritation:	0.571
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC476946

Natural Product ID:	NPC476946
*Common Name:**	(1R,2R,4aR,5S,6R,8aR)-5-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-1,5,6,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2-diol
IUPAC Name:	(1R,2R,4aR,5S,6R,8aR)-5-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-1,5,6,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2-diol
Synonyms:
Standard InCHIKey:	ZOVNGEHLBNZAPT-UDERSWLKSA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-13-7-9-19(3)16(5-6-17(22)20(19,4)23)18(13,2)11-15(21)14-8-10-24-12-14/h8,10,12-13,15-17,21-23H,5-7,9,11H2,1-4H3/t13-,15+,16-,17-,18+,19-,20+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)C[C@@H](C3=COC=C3)O)CC[C@H]([C@]2(C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90676771
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO33579	Croton laui	Species	Euphorbiaceae	Eukaryota	Twigs	Hainan Province, China	n.a.	PMID[24735527]

☑ 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
MIC	11

Activity Type	# Activity
Cell Line	2
Organism	10
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>=	10000	nM	PMID[24735527]
NPT168	Cell Line	P388	Mus musculus	IC50	>=	10000	nM	PMID[24735527]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	150000	nM	PMID[24735527]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	>	150000	nM	PMID[24735527]
NPT2	Others	Unspecified		MIC	>	150000	nM	PMID[24735527]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	150000	nM	PMID[24735527]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	150000	nM	PMID[24735527]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	150000	nM	PMID[24735527]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	150000	nM	PMID[24735527]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	150000	nM	PMID[24735527]
NPT1533	Organism	Saccharomyces	Saccharomyces	MIC	>	150000	nM	PMID[24735527]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	150000	nM	PMID[24735527]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	150000	nM	PMID[24735527]

☑ 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 NPC476946 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	322
0.1-0.2	1201
0.2-0.3	2735
0.3-0.4	5606
0.4-0.5	11211
0.5-0.6	9199
0.6-0.7	10417
0.7-0.8	1674
0.8-0.85	261
0.85-0.9	64
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9407	High Similarity	NPC476947
0.9353	High Similarity	NPC52412
0.9167	High Similarity	NPC470998
0.9155	High Similarity	NPC5676
0.9118	High Similarity	NPC218838
0.9085	High Similarity	NPC476944
0.9007	High Similarity	NPC205765
0.8971	High Similarity	NPC61788
0.894	High Similarity	NPC200782
0.8936	High Similarity	NPC67003
0.8904	High Similarity	NPC69647
0.8904	High Similarity	NPC125182
0.8851	High Similarity	NPC33938
0.8844	High Similarity	NPC470997
0.8828	High Similarity	NPC346
0.8811	High Similarity	NPC475519
0.8808	High Similarity	NPC475967
0.8792	High Similarity	NPC282445
0.8776	High Similarity	NPC195325
0.8776	High Similarity	NPC472654
0.8767	High Similarity	NPC302987
0.8767	High Similarity	NPC255414
0.8758	High Similarity	NPC472773
0.875	High Similarity	NPC243577
0.8742	High Similarity	NPC299038
0.8733	High Similarity	NPC264943
0.8733	High Similarity	NPC35000
0.8725	High Similarity	NPC469503
0.8707	High Similarity	NPC471007
0.8701	High Similarity	NPC470940
0.8701	High Similarity	NPC276551
0.8701	High Similarity	NPC470182
0.8693	High Similarity	NPC329938
0.8693	High Similarity	NPC82851
0.8693	High Similarity	NPC472771
0.8681	High Similarity	NPC121158
0.8681	High Similarity	NPC62103
0.8681	High Similarity	NPC20578
0.8667	High Similarity	NPC178932
0.8667	High Similarity	NPC30222
0.8658	High Similarity	NPC18135
0.8652	High Similarity	NPC46896
0.8649	High Similarity	NPC234494
0.8645	High Similarity	NPC470875
0.8636	High Similarity	NPC292389
0.8636	High Similarity	NPC288602
0.8636	High Similarity	NPC477405
0.8636	High Similarity	NPC88841
0.8636	High Similarity	NPC469338
0.8627	High Similarity	NPC472653
0.8627	High Similarity	NPC335761
0.8627	High Similarity	NPC477402
0.8621	High Similarity	NPC267632
0.8618	High Similarity	NPC472772
0.8618	High Similarity	NPC261597
0.8618	High Similarity	NPC45101
0.8618	High Similarity	NPC249021
0.8618	High Similarity	NPC472776
0.8618	High Similarity	NPC472778
0.8618	High Similarity	NPC472777
0.8609	High Similarity	NPC214541
0.8609	High Similarity	NPC469336
0.8609	High Similarity	NPC44675
0.8603	High Similarity	NPC23086
0.86	High Similarity	NPC75906
0.86	High Similarity	NPC476201
0.86	High Similarity	NPC268905
0.8592	High Similarity	NPC470742
0.8591	High Similarity	NPC196846
0.859	High Similarity	NPC472651
0.859	High Similarity	NPC472775
0.859	High Similarity	NPC472774
0.8581	High Similarity	NPC469849
0.8571	High Similarity	NPC5079
0.8571	High Similarity	NPC263432
0.8571	High Similarity	NPC188649
0.8571	High Similarity	NPC69028
0.8562	High Similarity	NPC307383
0.8562	High Similarity	NPC251865
0.8562	High Similarity	NPC475226
0.8543	High Similarity	NPC57998
0.8543	High Similarity	NPC302054
0.8543	High Similarity	NPC98206
0.8543	High Similarity	NPC253201
0.8543	High Similarity	NPC34421
0.8543	High Similarity	NPC237259
0.8542	High Similarity	NPC90296
0.8535	High Similarity	NPC471397
0.8535	High Similarity	NPC472652
0.8535	High Similarity	NPC271235
0.8535	High Similarity	NPC296558
0.8531	High Similarity	NPC476943
0.8526	High Similarity	NPC93172
0.8526	High Similarity	NPC472141
0.8526	High Similarity	NPC97574
0.8516	High Similarity	NPC234660
0.8516	High Similarity	NPC198047
0.8516	High Similarity	NPC51568
0.8516	High Similarity	NPC302369
0.8516	High Similarity	NPC134254
0.8516	High Similarity	NPC39986
0.8514	High Similarity	NPC250228
0.8514	High Similarity	NPC221809
0.8506	High Similarity	NPC470789
0.8503	High Similarity	NPC41182
0.8503	High Similarity	NPC185456
0.8497	Intermediate Similarity	NPC194499
0.8497	Intermediate Similarity	NPC36655
0.8487	Intermediate Similarity	NPC92979
0.8487	Intermediate Similarity	NPC476262
0.8487	Intermediate Similarity	NPC281258
0.8481	Intermediate Similarity	NPC82602
0.8477	Intermediate Similarity	NPC472672
0.8477	Intermediate Similarity	NPC470996
0.8472	Intermediate Similarity	NPC90953
0.8471	Intermediate Similarity	NPC472282
0.8471	Intermediate Similarity	NPC173516
0.8467	Intermediate Similarity	NPC476122
0.8467	Intermediate Similarity	NPC196864
0.8467	Intermediate Similarity	NPC477404
0.8462	Intermediate Similarity	NPC476856
0.8462	Intermediate Similarity	NPC310830
0.8462	Intermediate Similarity	NPC271657
0.8462	Intermediate Similarity	NPC476857
0.8462	Intermediate Similarity	NPC473268
0.8462	Intermediate Similarity	NPC476858
0.8452	Intermediate Similarity	NPC193798
0.8452	Intermediate Similarity	NPC470792
0.8452	Intermediate Similarity	NPC18986
0.8452	Intermediate Similarity	NPC18347
0.8452	Intermediate Similarity	NPC211777
0.8452	Intermediate Similarity	NPC207978
0.8452	Intermediate Similarity	NPC149896
0.8451	Intermediate Similarity	NPC158525
0.8451	Intermediate Similarity	NPC92941
0.8442	Intermediate Similarity	NPC474611
0.8442	Intermediate Similarity	NPC477403
0.8431	Intermediate Similarity	NPC469485
0.8429	Intermediate Similarity	NPC89133
0.8421	Intermediate Similarity	NPC114880
0.8418	Intermediate Similarity	NPC160651
0.8408	Intermediate Similarity	NPC121995
0.8403	Intermediate Similarity	NPC472376
0.8403	Intermediate Similarity	NPC471996
0.84	Intermediate Similarity	NPC211625
0.8397	Intermediate Similarity	NPC224394
0.8397	Intermediate Similarity	NPC663
0.8397	Intermediate Similarity	NPC472139
0.8389	Intermediate Similarity	NPC470941
0.8387	Intermediate Similarity	NPC287559
0.8387	Intermediate Similarity	NPC25255
0.8377	Intermediate Similarity	NPC88007
0.8377	Intermediate Similarity	NPC167142
0.8377	Intermediate Similarity	NPC173544
0.8377	Intermediate Similarity	NPC187149
0.8377	Intermediate Similarity	NPC470118
0.8367	Intermediate Similarity	NPC64568
0.8366	Intermediate Similarity	NPC141538
0.8366	Intermediate Similarity	NPC296807
0.8366	Intermediate Similarity	NPC155939
0.8365	Intermediate Similarity	NPC470995
0.8356	Intermediate Similarity	NPC20500
0.8355	Intermediate Similarity	NPC476940
0.8355	Intermediate Similarity	NPC294511
0.8355	Intermediate Similarity	NPC44577
0.8355	Intermediate Similarity	NPC121615
0.8355	Intermediate Similarity	NPC476939
0.8354	Intermediate Similarity	NPC476853
0.8354	Intermediate Similarity	NPC476850
0.8354	Intermediate Similarity	NPC476861
0.8345	Intermediate Similarity	NPC477040
0.8345	Intermediate Similarity	NPC112706
0.8345	Intermediate Similarity	NPC207294
0.8344	Intermediate Similarity	NPC159927
0.8344	Intermediate Similarity	NPC156189
0.8344	Intermediate Similarity	NPC469335
0.8344	Intermediate Similarity	NPC123088
0.8333	Intermediate Similarity	NPC68848
0.8333	Intermediate Similarity	NPC186626
0.8333	Intermediate Similarity	NPC476942
0.8333	Intermediate Similarity	NPC476941
0.8333	Intermediate Similarity	NPC4764
0.8333	Intermediate Similarity	NPC138139
0.8333	Intermediate Similarity	NPC46536
0.8323	Intermediate Similarity	NPC472671
0.8322	Intermediate Similarity	NPC262198
0.8322	Intermediate Similarity	NPC97904
0.8313	Intermediate Similarity	NPC294512
0.8312	Intermediate Similarity	NPC126723
0.8312	Intermediate Similarity	NPC209364
0.8312	Intermediate Similarity	NPC107646
0.8311	Intermediate Similarity	NPC137295
0.8311	Intermediate Similarity	NPC142113
0.831	Intermediate Similarity	NPC474407
0.831	Intermediate Similarity	NPC474425
0.831	Intermediate Similarity	NPC474426
0.8309	Intermediate Similarity	NPC477967
0.8309	Intermediate Similarity	NPC263870
0.8302	Intermediate Similarity	NPC472765
0.8302	Intermediate Similarity	NPC472766

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 NPC476946 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	861
0.2-0.3	1908
0.3-0.4	2636
0.4-0.5	2028
0.5-0.6	1064
0.6-0.7	350
0.7-0.8	11
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8859	High Similarity	NPD5761	Phase 2
0.8859	High Similarity	NPD5760	Phase 2
0.8024	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7412	Intermediate Similarity	NPD6559	Discontinued
0.7342	Intermediate Similarity	NPD6273	Approved
0.731	Intermediate Similarity	NPD6765	Approved
0.731	Intermediate Similarity	NPD6764	Approved
0.7273	Intermediate Similarity	NPD2344	Approved
0.7273	Intermediate Similarity	NPD1471	Phase 3
0.7255	Intermediate Similarity	NPD2799	Discontinued
0.7239	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2935	Discontinued
0.7205	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2346	Discontinued
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD6785	Approved
0.7143	Intermediate Similarity	NPD6784	Approved
0.7126	Intermediate Similarity	NPD5494	Approved
0.7089	Intermediate Similarity	NPD2309	Approved
0.7083	Intermediate Similarity	NPD8127	Discontinued
0.7076	Intermediate Similarity	NPD3818	Discontinued
0.7073	Intermediate Similarity	NPD1934	Approved
0.7067	Intermediate Similarity	NPD6832	Phase 2
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7059	Intermediate Similarity	NPD447	Suspended
0.7055	Intermediate Similarity	NPD4380	Phase 2
0.7055	Intermediate Similarity	NPD6599	Discontinued
0.703	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7819	Suspended
0.7025	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2424	Discontinued
0.7006	Intermediate Similarity	NPD7075	Discontinued
0.6988	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1551	Phase 2
0.6975	Remote Similarity	NPD920	Approved
0.6974	Remote Similarity	NPD2313	Discontinued
0.6962	Remote Similarity	NPD2800	Approved
0.6957	Remote Similarity	NPD2533	Approved
0.6957	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2532	Approved
0.6957	Remote Similarity	NPD2534	Approved
0.6957	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8404	Phase 2
0.6936	Remote Similarity	NPD5844	Phase 1
0.6932	Remote Similarity	NPD8313	Approved
0.6932	Remote Similarity	NPD8312	Approved
0.6928	Remote Similarity	NPD2801	Approved
0.6923	Remote Similarity	NPD4308	Phase 3
0.6918	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7003	Approved
0.6918	Remote Similarity	NPD4110	Phase 3
0.6905	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3749	Approved
0.6899	Remote Similarity	NPD1549	Phase 2
0.6892	Remote Similarity	NPD9717	Approved
0.689	Remote Similarity	NPD3226	Approved
0.689	Remote Similarity	NPD7458	Discontinued
0.6886	Remote Similarity	NPD5402	Approved
0.6882	Remote Similarity	NPD1247	Approved
0.6879	Remote Similarity	NPD6100	Approved
0.6879	Remote Similarity	NPD6099	Approved
0.6879	Remote Similarity	NPD2796	Approved
0.6867	Remote Similarity	NPD37	Approved
0.6867	Remote Similarity	NPD6801	Discontinued
0.6867	Remote Similarity	NPD2797	Approved
0.6867	Remote Similarity	NPD1203	Approved
0.686	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6166	Phase 2
0.6852	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4967	Phase 2
0.6845	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7768	Phase 2
0.6845	Remote Similarity	NPD4966	Approved
0.6845	Remote Similarity	NPD4965	Approved
0.6839	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5735	Approved
0.6835	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7236	Approved
0.6824	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7473	Discontinued
0.6821	Remote Similarity	NPD2798	Approved
0.6821	Remote Similarity	NPD5647	Approved
0.6813	Remote Similarity	NPD8166	Discontinued
0.68	Remote Similarity	NPD7074	Phase 3
0.6795	Remote Similarity	NPD6653	Approved
0.679	Remote Similarity	NPD6799	Approved
0.679	Remote Similarity	NPD1511	Approved
0.6786	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6959	Discontinued
0.6779	Remote Similarity	NPD3972	Approved
0.6776	Remote Similarity	NPD9494	Approved
0.6774	Remote Similarity	NPD4140	Approved
0.6768	Remote Similarity	NPD5403	Approved
0.6766	Remote Similarity	NPD6844	Discontinued
0.6765	Remote Similarity	NPD919	Approved
0.6765	Remote Similarity	NPD6234	Discontinued
0.676	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD411	Approved
0.6753	Remote Similarity	NPD3268	Approved
0.675	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6232	Discontinued
0.6743	Remote Similarity	NPD7054	Approved
0.6743	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6002	Phase 3
0.673	Remote Similarity	NPD6005	Phase 3
0.673	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5763	Approved
0.673	Remote Similarity	NPD6004	Phase 3
0.673	Remote Similarity	NPD5762	Approved
0.6728	Remote Similarity	NPD643	Clinical (unspecified phase)
0.671	Remote Similarity	NPD8032	Phase 2
0.6709	Remote Similarity	NPD7033	Discontinued
0.6709	Remote Similarity	NPD1510	Phase 2
0.6708	Remote Similarity	NPD3750	Approved
0.6707	Remote Similarity	NPD7411	Suspended
0.6707	Remote Similarity	NPD1512	Approved
0.6705	Remote Similarity	NPD7472	Approved
0.6705	Remote Similarity	NPD3926	Phase 2
0.669	Remote Similarity	NPD7157	Approved
0.6689	Remote Similarity	NPD1876	Approved
0.6688	Remote Similarity	NPD7095	Approved
0.6688	Remote Similarity	NPD1607	Approved
0.6688	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2651	Approved
0.6687	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2649	Approved
0.6686	Remote Similarity	NPD7228	Approved
0.6686	Remote Similarity	NPD3751	Discontinued
0.6686	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD1240	Approved
0.6647	Remote Similarity	NPD7028	Phase 2
0.6646	Remote Similarity	NPD5401	Approved
0.6646	Remote Similarity	NPD7097	Phase 1
0.6646	Remote Similarity	NPD4662	Approved
0.6646	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4661	Approved
0.6645	Remote Similarity	NPD6798	Discontinued
0.6645	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3764	Approved
0.663	Remote Similarity	NPD8150	Discontinued
0.6629	Remote Similarity	NPD7251	Discontinued
0.6627	Remote Similarity	NPD7239	Suspended
0.6624	Remote Similarity	NPD1933	Approved
0.6623	Remote Similarity	NPD5327	Phase 3
0.6605	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6233	Phase 2
0.6601	Remote Similarity	NPD1019	Discontinued
0.6592	Remote Similarity	NPD7808	Phase 3
0.6591	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD2296	Approved
0.6582	Remote Similarity	NPD6353	Approved
0.6579	Remote Similarity	NPD1283	Approved
0.6577	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6797	Phase 2
0.6571	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6279	Approved
0.6568	Remote Similarity	NPD6280	Approved
0.6562	Remote Similarity	NPD2438	Suspended
0.6561	Remote Similarity	NPD2979	Phase 3
0.6561	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3620	Phase 2
0.6557	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3787	Discontinued
0.6552	Remote Similarity	NPD1241	Discontinued
0.6552	Remote Similarity	NPD6808	Phase 2
0.6543	Remote Similarity	NPD1243	Approved
0.6538	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7685	Pre-registration
0.6533	Remote Similarity	NPD4111	Phase 1
0.6533	Remote Similarity	NPD4665	Approved
0.6514	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5585	Approved
0.65	Remote Similarity	NPD3748	Approved
0.65	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6663	Approved
0.6494	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7199	Phase 2
0.6481	Remote Similarity	NPD4534	Discontinued
0.648	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6651	Approved
0.6477	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6696	Suspended
0.6468	Remote Similarity	NPD7907	Approved
0.646	Remote Similarity	NPD4477	Approved
0.646	Remote Similarity	NPD4476	Approved
0.6457	Remote Similarity	NPD5710	Approved
0.6457	Remote Similarity	NPD5711	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