NPASS Compound

Structure

NPC8050 OpenBabel07101718322D 30 33 0 0 1 0 0 0 0 0999 V2000 5.8558 -2.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9898 2.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1237 -1.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2577 0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9898 0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -2.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2577 -0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9898 -0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1237 0.9351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7026 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3917 -1.0649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7026 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8558 -1.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1237 1.9351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -3.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2872 -2.0594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 13 2 0 0 0 0 6 15 1 0 0 0 0 7 13 1 0 0 0 0 7 16 2 0 0 0 0 8 14 2 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 20 2 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 30 1 0 0 0 0 12 29 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 11 1 6 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 12 1 6 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 21 13 1 6 0 0 0 21 29 1 0 0 0 0 22 14 1 1 0 0 0 22 30 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.18
Volume:	417.851
LogP:	3.496
LogD:	3.367
LogS:	-4.708
# Rotatable Bonds:	7
TPSA:	64.61
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	3.684
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.905
MDCK Permeability:	6.1010781791992486e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.353
Plasma Protein Binding (PPB):	67.0753173828125%
Volume Distribution (VD):	0.823
Pgp-substrate:	18.342525482177734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.134
CYP2C19-substrate:	0.937
CYP2C9-inhibitor:	0.265
CYP2C9-substrate:	0.607
CYP2D6-inhibitor:	0.161
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.664
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	7.166
Half-life (T1/2):	0.296

ADMET: Toxicity

hERG Blockers:	0.683
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.952
Carcinogencity:	0.026
Eye Corrosion:	0.004
Eye Irritation:	0.05
Respiratory Toxicity:	0.164

Download Data

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

Natural Product: NPC8050

Natural Product ID:	NPC8050
*Common Name:**	Epimagnolin B
IUPAC Name:	(3R,3aR,6S,6aR)-3-(3,5-dimethoxyphenyl)-6-(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan
Synonyms:
Standard InCHIKey:	DTZKTJXOROSTPI-YHDSQAASSA-N
Standard InCHI:	InChI=1S/C23H28O7/c1-24-15-6-13(7-16(10-15)25-2)21-17-11-30-22(18(17)12-29-21)14-8-19(26-3)23(28-5)20(9-14)27-4/h6-10,17-18,21-22H,11-12H2,1-5H3/t17-,18-,21-,22+/m0/s1
SMILES:	COc1cc(OC)cc(c1)[C@@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480759
PubChem CID:	25194949
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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
NPO17167	Magnolia fargesii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19110419]
NPO17167	Magnolia fargesii	Species	Magnoliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[9644071]
NPO17167	Magnolia fargesii	Species	Magnoliaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	10900.0	nM	PMID[509180]

☑ 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 NPC8050 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	501
0.1-0.2	1477
0.2-0.3	4259
0.3-0.4	12427
0.4-0.5	6579
0.5-0.6	6064
0.6-0.7	8740
0.7-0.8	1999
0.8-0.85	480
0.85-0.9	115
0.9-0.95	42
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473092
1.0	High Similarity	NPC473093
0.9917	High Similarity	NPC328682
0.9917	High Similarity	NPC222127
0.9917	High Similarity	NPC82862
0.9917	High Similarity	NPC54321
0.9917	High Similarity	NPC281864
0.9752	High Similarity	NPC285725
0.9752	High Similarity	NPC88297
0.9752	High Similarity	NPC50683
0.9752	High Similarity	NPC186845
0.9752	High Similarity	NPC9891
0.9752	High Similarity	NPC112571
0.96	High Similarity	NPC261812
0.96	High Similarity	NPC72046
0.96	High Similarity	NPC65183
0.9587	High Similarity	NPC18449
0.9587	High Similarity	NPC121783
0.9587	High Similarity	NPC34902
0.9524	High Similarity	NPC136750
0.9524	High Similarity	NPC266848
0.9449	High Similarity	NPC31530
0.944	High Similarity	NPC237169
0.944	High Similarity	NPC470624
0.9375	High Similarity	NPC99572
0.9375	High Similarity	NPC189474
0.9375	High Similarity	NPC165155
0.9375	High Similarity	NPC34103
0.9375	High Similarity	NPC25333
0.9375	High Similarity	NPC148893
0.9375	High Similarity	NPC141765
0.9375	High Similarity	NPC126409
0.9375	High Similarity	NPC24490
0.9375	High Similarity	NPC49235
0.9365	High Similarity	NPC192255
0.9339	High Similarity	NPC126935
0.9339	High Similarity	NPC172676
0.9339	High Similarity	NPC57268
0.9339	High Similarity	NPC312713
0.9339	High Similarity	NPC65933
0.9339	High Similarity	NPC216929
0.9302	High Similarity	NPC121651
0.9302	High Similarity	NPC78047
0.9291	High Similarity	NPC204215
0.9291	High Similarity	NPC175067
0.9291	High Similarity	NPC475856
0.9219	High Similarity	NPC158331
0.9219	High Similarity	NPC1474
0.918	High Similarity	NPC477886
0.916	High Similarity	NPC113550
0.9154	High Similarity	NPC11453
0.9147	High Similarity	NPC287745
0.9147	High Similarity	NPC326095
0.9147	High Similarity	NPC474478
0.9147	High Similarity	NPC244983
0.9141	High Similarity	NPC7744
0.9127	High Similarity	NPC158471
0.9127	High Similarity	NPC165128
0.9127	High Similarity	NPC226862
0.9127	High Similarity	NPC57119
0.912	High Similarity	NPC206882
0.9106	High Similarity	NPC261661
0.9091	High Similarity	NPC216434
0.9091	High Similarity	NPC103448
0.9091	High Similarity	NPC254625
0.9091	High Similarity	NPC46591
0.9091	High Similarity	NPC475961
0.9091	High Similarity	NPC177868
0.9084	High Similarity	NPC185908
0.9084	High Similarity	NPC283949
0.9077	High Similarity	NPC150534
0.9062	High Similarity	NPC40432
0.9062	High Similarity	NPC27843
0.9062	High Similarity	NPC115207
0.9062	High Similarity	NPC161557
0.9062	High Similarity	NPC141493
0.9062	High Similarity	NPC158079
0.9062	High Similarity	NPC228346
0.9062	High Similarity	NPC7171
0.9062	High Similarity	NPC227160
0.9062	High Similarity	NPC184928
0.9062	High Similarity	NPC82111
0.9023	High Similarity	NPC312199
0.8992	High Similarity	NPC207400
0.8992	High Similarity	NPC181049
0.8984	High Similarity	NPC233224
0.8984	High Similarity	NPC271208
0.8976	High Similarity	NPC470084
0.8976	High Similarity	NPC31707
0.8955	High Similarity	NPC80326
0.8955	High Similarity	NPC474295
0.8955	High Similarity	NPC287124
0.8955	High Similarity	NPC472562
0.8947	High Similarity	NPC226547
0.8947	High Similarity	NPC56091
0.8943	High Similarity	NPC472596
0.8939	High Similarity	NPC477938
0.8934	High Similarity	NPC15805
0.8931	High Similarity	NPC236522
0.8923	High Similarity	NPC196937
0.8915	High Similarity	NPC474017
0.8898	High Similarity	NPC189248
0.8898	High Similarity	NPC202904
0.8898	High Similarity	NPC98745
0.8898	High Similarity	NPC242032
0.8889	High Similarity	NPC255566
0.8889	High Similarity	NPC12728
0.8889	High Similarity	NPC298317
0.8889	High Similarity	NPC185071
0.8881	High Similarity	NPC58137
0.8881	High Similarity	NPC300798
0.8864	High Similarity	NPC143895
0.8864	High Similarity	NPC32189
0.8855	High Similarity	NPC145769
0.8846	High Similarity	NPC129687
0.8846	High Similarity	NPC33611
0.8846	High Similarity	NPC158526
0.8846	High Similarity	NPC4940
0.8846	High Similarity	NPC100223
0.8846	High Similarity	NPC171928
0.8846	High Similarity	NPC16830
0.8843	High Similarity	NPC123948
0.8837	High Similarity	NPC187998
0.8837	High Similarity	NPC257582
0.8837	High Similarity	NPC42300
0.8837	High Similarity	NPC174495
0.8837	High Similarity	NPC242807
0.8837	High Similarity	NPC145305
0.8837	High Similarity	NPC64201
0.8837	High Similarity	NPC153739
0.8837	High Similarity	NPC77040
0.8837	High Similarity	NPC92164
0.8837	High Similarity	NPC241522
0.8828	High Similarity	NPC129570
0.8828	High Similarity	NPC128208
0.8828	High Similarity	NPC282703
0.8828	High Similarity	NPC283114
0.8828	High Similarity	NPC21867
0.8828	High Similarity	NPC184733
0.8828	High Similarity	NPC45774
0.8828	High Similarity	NPC207702
0.8828	High Similarity	NPC210674
0.8828	High Similarity	NPC149008
0.8828	High Similarity	NPC11258
0.8824	High Similarity	NPC471415
0.8824	High Similarity	NPC114119
0.8824	High Similarity	NPC166884
0.8824	High Similarity	NPC470097
0.8824	High Similarity	NPC477701
0.8824	High Similarity	NPC141569
0.8819	High Similarity	NPC76451
0.8815	High Similarity	NPC311057
0.8815	High Similarity	NPC174522
0.8806	High Similarity	NPC309124
0.8806	High Similarity	NPC27495
0.8806	High Similarity	NPC254759
0.8806	High Similarity	NPC184797
0.8806	High Similarity	NPC160283
0.8797	High Similarity	NPC474039
0.8788	High Similarity	NPC211386
0.8788	High Similarity	NPC72796
0.8788	High Similarity	NPC44245
0.8788	High Similarity	NPC474139
0.8769	High Similarity	NPC277804
0.876	High Similarity	NPC285339
0.876	High Similarity	NPC202582
0.876	High Similarity	NPC273295
0.876	High Similarity	NPC470258
0.876	High Similarity	NPC475875
0.876	High Similarity	NPC3439
0.876	High Similarity	NPC222004
0.876	High Similarity	NPC476968
0.876	High Similarity	NPC170844
0.876	High Similarity	NPC226788
0.876	High Similarity	NPC218856
0.876	High Similarity	NPC190629
0.876	High Similarity	NPC210623
0.8759	High Similarity	NPC477702
0.8759	High Similarity	NPC205316
0.8759	High Similarity	NPC180953
0.875	High Similarity	NPC474119
0.875	High Similarity	NPC127587
0.875	High Similarity	NPC474808
0.8741	High Similarity	NPC247291
0.8741	High Similarity	NPC263261
0.8741	High Similarity	NPC87725
0.8741	High Similarity	NPC311530
0.8731	High Similarity	NPC232164
0.8731	High Similarity	NPC9068
0.8731	High Similarity	NPC236306
0.8731	High Similarity	NPC292882
0.8731	High Similarity	NPC473739
0.873	High Similarity	NPC282496
0.873	High Similarity	NPC233526
0.8722	High Similarity	NPC209229
0.8712	High Similarity	NPC170779
0.8712	High Similarity	NPC90083
0.8712	High Similarity	NPC145722
0.8712	High Similarity	NPC185680
0.8712	High Similarity	NPC47181

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 NPC8050 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	874
0.2-0.3	1803
0.3-0.4	2900
0.4-0.5	1699
0.5-0.6	993
0.6-0.7	428
0.7-0.8	67
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.876	High Similarity	NPD3027	Phase 3
0.8595	High Similarity	NPD5283	Phase 1
0.8425	Intermediate Similarity	NPD3705	Approved
0.8359	Intermediate Similarity	NPD2981	Phase 2
0.8295	Intermediate Similarity	NPD2982	Phase 2
0.8295	Intermediate Similarity	NPD2983	Phase 2
0.8182	Intermediate Similarity	NPD3018	Phase 2
0.8148	Intermediate Similarity	NPD1613	Approved
0.8148	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD4966	Approved
0.8108	Intermediate Similarity	NPD4965	Approved
0.8108	Intermediate Similarity	NPD4967	Phase 2
0.8085	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6234	Discontinued
0.7985	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD37	Approved
0.7852	Intermediate Similarity	NPD4908	Phase 1
0.7778	Intermediate Similarity	NPD7124	Phase 2
0.7737	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1610	Phase 2
0.7714	Intermediate Similarity	NPD6111	Discontinued
0.7712	Intermediate Similarity	NPD5494	Approved
0.7682	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2861	Phase 2
0.7643	Intermediate Similarity	NPD7228	Approved
0.7615	Intermediate Similarity	NPD5536	Phase 2
0.7606	Intermediate Similarity	NPD3539	Phase 1
0.7571	Intermediate Similarity	NPD3657	Discovery
0.7568	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3540	Phase 1
0.7548	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD3620	Phase 2
0.75	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD5109	Approved
0.7482	Intermediate Similarity	NPD5110	Phase 2
0.7482	Intermediate Similarity	NPD5111	Phase 2
0.7481	Intermediate Similarity	NPD4749	Approved
0.7467	Intermediate Similarity	NPD4005	Discontinued
0.7453	Intermediate Similarity	NPD7240	Approved
0.7452	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4236	Phase 3
0.7448	Intermediate Similarity	NPD4237	Approved
0.7445	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1934	Approved
0.7424	Intermediate Similarity	NPD1548	Phase 1
0.7422	Intermediate Similarity	NPD228	Approved
0.7383	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1357	Approved
0.7365	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5327	Phase 3
0.7338	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6674	Discontinued
0.7328	Intermediate Similarity	NPD7157	Approved
0.7323	Intermediate Similarity	NPD2684	Approved
0.731	Intermediate Similarity	NPD1375	Discontinued
0.7303	Intermediate Similarity	NPD4678	Approved
0.7303	Intermediate Similarity	NPD4675	Approved
0.7292	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3882	Suspended
0.7286	Intermediate Similarity	NPD4625	Phase 3
0.7285	Intermediate Similarity	NPD4210	Discontinued
0.7279	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4110	Phase 3
0.7279	Intermediate Similarity	NPD6331	Phase 2
0.7279	Intermediate Similarity	NPD7466	Approved
0.7273	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3022	Approved
0.7266	Intermediate Similarity	NPD3021	Approved
0.7248	Intermediate Similarity	NPD4357	Discontinued
0.7241	Intermediate Similarity	NPD2161	Phase 2
0.7237	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7843	Approved
0.7226	Intermediate Similarity	NPD3817	Phase 2
0.7226	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6896	Approved
0.7222	Intermediate Similarity	NPD6895	Approved
0.7211	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5735	Approved
0.7179	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5588	Approved
0.7162	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3892	Phase 2
0.7161	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5297	Approved
0.7133	Intermediate Similarity	NPD4060	Phase 1
0.7133	Intermediate Similarity	NPD2238	Phase 2
0.7132	Intermediate Similarity	NPD5451	Approved
0.7125	Intermediate Similarity	NPD5242	Approved
0.7125	Intermediate Similarity	NPD3926	Phase 2
0.7123	Intermediate Similarity	NPD2796	Approved
0.7123	Intermediate Similarity	NPD2438	Suspended
0.7115	Intermediate Similarity	NPD5353	Approved
0.7114	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2219	Phase 1
0.7111	Intermediate Similarity	NPD5585	Approved
0.7108	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4536	Approved
0.7103	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4538	Approved
0.7101	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5535	Approved
0.7099	Intermediate Similarity	NPD3818	Discontinued
0.7097	Intermediate Similarity	NPD3383	Approved
0.7097	Intermediate Similarity	NPD3382	Approved
0.7097	Intermediate Similarity	NPD3384	Approved
0.7095	Intermediate Similarity	NPD3060	Approved
0.7095	Intermediate Similarity	NPD5177	Phase 3
0.7083	Intermediate Similarity	NPD6355	Discontinued
0.7081	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6166	Phase 2
0.7081	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5058	Phase 3
0.7063	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1653	Approved
0.7059	Intermediate Similarity	NPD17	Approved
0.7055	Intermediate Similarity	NPD5844	Phase 1
0.705	Intermediate Similarity	NPD2922	Phase 1
0.705	Intermediate Similarity	NPD8651	Approved
0.7039	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1182	Approved
0.7029	Intermediate Similarity	NPD1840	Phase 2
0.7025	Intermediate Similarity	NPD4055	Discovery
0.7014	Intermediate Similarity	NPD1558	Phase 1
0.7014	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD4750	Phase 3
0.7	Intermediate Similarity	NPD1247	Approved
0.6993	Remote Similarity	NPD5718	Phase 2
0.6993	Remote Similarity	NPD5976	Discontinued
0.6985	Remote Similarity	NPD5691	Approved
0.6985	Remote Similarity	NPD1651	Approved
0.6981	Remote Similarity	NPD919	Approved
0.698	Remote Similarity	NPD4162	Approved
0.6977	Remote Similarity	NPD1358	Approved
0.6974	Remote Similarity	NPD4123	Phase 3
0.6959	Remote Similarity	NPD5763	Approved
0.6959	Remote Similarity	NPD7266	Discontinued
0.6959	Remote Similarity	NPD5762	Approved
0.6957	Remote Similarity	NPD1091	Approved
0.6957	Remote Similarity	NPD6232	Discontinued
0.6954	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5960	Phase 3
0.6934	Remote Similarity	NPD5846	Approved
0.6934	Remote Similarity	NPD6516	Phase 2
0.6933	Remote Similarity	NPD7473	Discontinued
0.6928	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7526	Approved
0.6928	Remote Similarity	NPD52	Approved
0.6923	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5089	Approved
0.6923	Remote Similarity	NPD7095	Approved
0.6923	Remote Similarity	NPD5090	Approved
0.6918	Remote Similarity	NPD6353	Approved
0.6913	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7074	Phase 3
0.6908	Remote Similarity	NPD1511	Approved
0.6906	Remote Similarity	NPD1608	Approved
0.6905	Remote Similarity	NPD1242	Phase 1
0.6899	Remote Similarity	NPD3134	Approved
0.6899	Remote Similarity	NPD2563	Approved
0.6899	Remote Similarity	NPD2560	Approved
0.6897	Remote Similarity	NPD4140	Approved
0.6892	Remote Similarity	NPD6099	Approved
0.6892	Remote Similarity	NPD6100	Approved
0.6889	Remote Similarity	NPD3596	Phase 2
0.6887	Remote Similarity	NPD2677	Approved
0.6886	Remote Similarity	NPD7549	Discontinued
0.6867	Remote Similarity	NPD1652	Phase 2
0.6864	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4380	Phase 2
0.6857	Remote Similarity	NPD4359	Approved
0.6855	Remote Similarity	NPD6788	Approved
0.6853	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7229	Phase 3
0.6849	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD230	Phase 1
0.6849	Remote Similarity	NPD5124	Phase 1
0.6848	Remote Similarity	NPD8156	Discontinued
0.6848	Remote Similarity	NPD7054	Approved
0.6846	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD290	Approved
0.6838	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2977	Approved
0.6835	Remote Similarity	NPD1281	Approved
0.6835	Remote Similarity	NPD422	Phase 1
0.6835	Remote Similarity	NPD5772	Approved
0.6835	Remote Similarity	NPD2978	Approved
0.6835	Remote Similarity	NPD4585	Approved
0.6835	Remote Similarity	NPD5773	Approved
0.6831	Remote Similarity	NPD4624	Approved
0.6831	Remote Similarity	NPD6584	Phase 3
0.6828	Remote Similarity	NPD6233	Phase 2
0.6825	Remote Similarity	NPD3020	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