NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	644.26
Volume:	659.354
LogP:	5.174
LogD:	4.174
LogS:	-6.38
# Rotatable Bonds:	11
TPSA:	107.98
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.175
Synthetic Accessibility Score:	4.418
Fsp3:	0.351
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.793
MDCK Permeability:	2.0233912437106483e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	85.66281127929688%
Volume Distribution (VD):	0.399
Pgp-substrate:	10.929766654968262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.974
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.969
CYP2C9-substrate:	0.813
CYP2D6-inhibitor:	0.303
CYP2D6-substrate:	0.322
CYP3A4-inhibitor:	0.952
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	4.112
Half-life (T1/2):	0.075

ADMET: Toxicity

hERG Blockers:	0.165
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.098
Skin Sensitization:	0.425
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.245
Respiratory Toxicity:	0.084

Download Data

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

Natural Product: NPC477377

Natural Product ID:	NPC477377
*Common Name:**	Polysperlignan E
IUPAC Name:	[(8R,9S,10R,11R)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-[(E)-3-phenylprop-2-enoyl]oxy-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-11-yl] (Z)-2-methylbut-2-enoate
Synonyms:	Polysperlignan E
Standard InCHIKey:	DHKOFLWROPIHJS-HWDZMEBBSA-N
Standard InCHI:	InChI=1S/C37H40O10/c1-9-20(2)37(39)47-32-22(4)21(3)31(46-28(38)16-15-23-13-11-10-12-14-23)24-17-26(40-5)33(41-6)35(42-7)29(24)30-25(32)18-27-34(36(30)43-8)45-19-44-27/h9-18,21-22,31-32H,19H2,1-8H3/b16-15+,20-9-/t21-,22+,31+,32+/m0/s1
SMILES:	C/C=C(/C)\C(=O)O[C@@H]1[C@@H]([C@@H]([C@H](C2=CC(=C(C(=C2C3=C(C4=C(C=C13)OCO4)OC)OC)OC)OC)OC(=O)/C=C/C5=CC=CC=C5)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	57333572
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO23565	Kadsura polysperma	Species	Schisandraceae	Eukaryota	stems	Emei County of Sichuan Province, China	2009-AUG	PMID[22329624]
NPO23565	Kadsura polysperma	Species	Schisandraceae	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
Others	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	39	%	PMID[22329624]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	39.7	%	PMID[22329624]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	57.1	%	PMID[22329624]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	58.9	%	PMID[22329624]

☑ 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 NPC477377 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	404
0.1-0.2	1531
0.2-0.3	3605
0.3-0.4	9015
0.4-0.5	9742
0.5-0.6	3906
0.6-0.7	8228
0.7-0.8	5761
0.8-0.85	363
0.85-0.9	86
0.9-0.95	45
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC475229
0.9931	High Similarity	NPC477378
0.9724	High Similarity	NPC477374
0.9724	High Similarity	NPC322426
0.9724	High Similarity	NPC477376
0.9658	High Similarity	NPC316989
0.9655	High Similarity	NPC327352
0.9655	High Similarity	NPC252281
0.9655	High Similarity	NPC477375
0.9655	High Similarity	NPC198129
0.9539	High Similarity	NPC319749
0.9456	High Similarity	NPC85141
0.9448	High Similarity	NPC327651
0.9448	High Similarity	NPC318286
0.9408	High Similarity	NPC230531
0.9408	High Similarity	NPC215400
0.9384	High Similarity	NPC321958
0.9384	High Similarity	NPC321696
0.9379	High Similarity	NPC326144
0.9355	High Similarity	NPC477884
0.9333	High Similarity	NPC126405
0.9333	High Similarity	NPC308739
0.9333	High Similarity	NPC16791
0.9333	High Similarity	NPC217708
0.9333	High Similarity	NPC53669
0.9333	High Similarity	NPC297271
0.9333	High Similarity	NPC24562
0.9333	High Similarity	NPC77237
0.931	High Similarity	NPC218510
0.931	High Similarity	NPC76415
0.9286	High Similarity	NPC258322
0.9286	High Similarity	NPC191352
0.9226	High Similarity	NPC280778
0.9216	High Similarity	NPC475592
0.9216	High Similarity	NPC477885
0.9211	High Similarity	NPC476065
0.92	High Similarity	NPC224472
0.9172	High Similarity	NPC118162
0.9172	High Similarity	NPC320471
0.9172	High Similarity	NPC83049
0.915	High Similarity	NPC473323
0.915	High Similarity	NPC477380
0.9145	High Similarity	NPC198461
0.9145	High Similarity	NPC348849
0.9145	High Similarity	NPC312763
0.9145	High Similarity	NPC178195
0.9119	High Similarity	NPC477883
0.9079	High Similarity	NPC475141
0.902	High Similarity	NPC473736
0.9013	High Similarity	NPC471154
0.9006	High Similarity	NPC477881
0.9	High Similarity	NPC325720
0.9	High Similarity	NPC316676
0.8994	High Similarity	NPC311912
0.8994	High Similarity	NPC79322
0.8966	High Similarity	NPC865
0.8954	High Similarity	NPC474606
0.8947	High Similarity	NPC475756
0.8947	High Similarity	NPC303519
0.8938	High Similarity	NPC88557
0.8933	High Similarity	NPC295297
0.891	High Similarity	NPC325122
0.8897	High Similarity	NPC143895
0.8896	High Similarity	NPC473425
0.8882	High Similarity	NPC473989
0.8841	High Similarity	NPC477882
0.8841	High Similarity	NPC477880
0.8839	High Similarity	NPC238834
0.8824	High Similarity	NPC477379
0.8816	High Similarity	NPC474347
0.8816	High Similarity	NPC474393
0.8782	High Similarity	NPC29727
0.8759	High Similarity	NPC145722
0.8759	High Similarity	NPC185680
0.8759	High Similarity	NPC256776
0.8758	High Similarity	NPC477381
0.8758	High Similarity	NPC470916
0.875	High Similarity	NPC252402
0.875	High Similarity	NPC102934
0.8742	High Similarity	NPC473445
0.8718	High Similarity	NPC117154
0.871	High Similarity	NPC474514
0.8707	High Similarity	NPC196420
0.8701	High Similarity	NPC210642
0.8701	High Similarity	NPC13985
0.8688	High Similarity	NPC291977
0.8684	High Similarity	NPC183083
0.8684	High Similarity	NPC137352
0.8671	High Similarity	NPC241600
0.8671	High Similarity	NPC173726
0.8667	High Similarity	NPC324962
0.8654	High Similarity	NPC273578
0.8639	High Similarity	NPC32189
0.8639	High Similarity	NPC11453
0.8636	High Similarity	NPC24425
0.8636	High Similarity	NPC149505
0.8625	High Similarity	NPC249070
0.8625	High Similarity	NPC42797
0.8616	High Similarity	NPC63061
0.8609	High Similarity	NPC474036
0.86	High Similarity	NPC229172
0.86	High Similarity	NPC103637
0.86	High Similarity	NPC36531
0.86	High Similarity	NPC230538
0.8591	High Similarity	NPC103448
0.8591	High Similarity	NPC216434
0.859	High Similarity	NPC149735
0.8553	High Similarity	NPC125713
0.8553	High Similarity	NPC474043
0.8553	High Similarity	NPC475868
0.8553	High Similarity	NPC328122
0.8552	High Similarity	NPC184928
0.8552	High Similarity	NPC141493
0.8526	High Similarity	NPC220577
0.8526	High Similarity	NPC478268
0.8526	High Similarity	NPC302610
0.8523	High Similarity	NPC53722
0.8523	High Similarity	NPC201404
0.8523	High Similarity	NPC290714
0.8509	High Similarity	NPC61141
0.8506	High Similarity	NPC262804
0.8506	High Similarity	NPC40654
0.8506	High Similarity	NPC477879
0.85	High Similarity	NPC96593
0.8497	Intermediate Similarity	NPC474054
0.8491	Intermediate Similarity	NPC125495
0.8491	Intermediate Similarity	NPC19947
0.8491	Intermediate Similarity	NPC207584
0.8487	Intermediate Similarity	NPC172171
0.8487	Intermediate Similarity	NPC18211
0.8487	Intermediate Similarity	NPC143092
0.8487	Intermediate Similarity	NPC475000
0.8487	Intermediate Similarity	NPC121661
0.8487	Intermediate Similarity	NPC239254
0.8487	Intermediate Similarity	NPC73467
0.8487	Intermediate Similarity	NPC87883
0.8485	Intermediate Similarity	NPC469506
0.8477	Intermediate Similarity	NPC287124
0.8477	Intermediate Similarity	NPC474295
0.8471	Intermediate Similarity	NPC245948
0.8447	Intermediate Similarity	NPC288149
0.8442	Intermediate Similarity	NPC101755
0.8442	Intermediate Similarity	NPC80230
0.8442	Intermediate Similarity	NPC104024
0.8442	Intermediate Similarity	NPC304687
0.8442	Intermediate Similarity	NPC65574
0.8438	Intermediate Similarity	NPC478269
0.8435	Intermediate Similarity	NPC136750
0.8435	Intermediate Similarity	NPC266848
0.8434	Intermediate Similarity	NPC474568
0.8431	Intermediate Similarity	NPC474158
0.8431	Intermediate Similarity	NPC166506
0.8431	Intermediate Similarity	NPC110763
0.8431	Intermediate Similarity	NPC189239
0.8431	Intermediate Similarity	NPC197352
0.8428	Intermediate Similarity	NPC239113
0.8428	Intermediate Similarity	NPC301897
0.8428	Intermediate Similarity	NPC32373
0.8428	Intermediate Similarity	NPC237946
0.8428	Intermediate Similarity	NPC115123
0.8421	Intermediate Similarity	NPC469630
0.8415	Intermediate Similarity	NPC475453
0.8415	Intermediate Similarity	NPC473531
0.8411	Intermediate Similarity	NPC312199
0.8408	Intermediate Similarity	NPC472611
0.8408	Intermediate Similarity	NPC472612
0.8408	Intermediate Similarity	NPC104353
0.8408	Intermediate Similarity	NPC476434
0.8408	Intermediate Similarity	NPC289967
0.8387	Intermediate Similarity	NPC93924
0.8387	Intermediate Similarity	NPC304821
0.8377	Intermediate Similarity	NPC154971
0.8377	Intermediate Similarity	NPC193779
0.8377	Intermediate Similarity	NPC252286
0.8367	Intermediate Similarity	NPC65183
0.8367	Intermediate Similarity	NPC7744
0.8367	Intermediate Similarity	NPC261812
0.8367	Intermediate Similarity	NPC475856
0.8367	Intermediate Similarity	NPC72046
0.8366	Intermediate Similarity	NPC141569
0.8366	Intermediate Similarity	NPC477701
0.8366	Intermediate Similarity	NPC166884
0.8365	Intermediate Similarity	NPC234730
0.8355	Intermediate Similarity	NPC67467
0.8355	Intermediate Similarity	NPC80326
0.8355	Intermediate Similarity	NPC40237
0.8355	Intermediate Similarity	NPC210354
0.8355	Intermediate Similarity	NPC151423
0.8355	Intermediate Similarity	NPC133934
0.8355	Intermediate Similarity	NPC176586
0.8355	Intermediate Similarity	NPC184684
0.8355	Intermediate Similarity	NPC184641
0.8354	Intermediate Similarity	NPC471923
0.8354	Intermediate Similarity	NPC474042
0.8354	Intermediate Similarity	NPC59516
0.8354	Intermediate Similarity	NPC174734
0.8345	Intermediate Similarity	NPC207702
0.8345	Intermediate Similarity	NPC283114
0.8345	Intermediate Similarity	NPC149008
0.8344	Intermediate Similarity	NPC469518

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 NPC477377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	930
0.2-0.3	1694
0.3-0.4	2804
0.4-0.5	1795
0.5-0.6	971
0.6-0.7	534
0.7-0.8	88
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8471	Intermediate Similarity	NPD37	Approved
0.8428	Intermediate Similarity	NPD4965	Approved
0.8428	Intermediate Similarity	NPD4966	Approved
0.8428	Intermediate Similarity	NPD4967	Phase 2
0.8387	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7199	Phase 2
0.8323	Intermediate Similarity	NPD6234	Discontinued
0.8232	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7228	Approved
0.7895	Intermediate Similarity	NPD7240	Approved
0.7862	Intermediate Similarity	NPD3705	Approved
0.7848	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD5844	Phase 1
0.7811	Intermediate Similarity	NPD7473	Discontinued
0.7764	Intermediate Similarity	NPD1653	Approved
0.7738	Intermediate Similarity	NPD6232	Discontinued
0.7714	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3818	Discontinued
0.7651	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5494	Approved
0.758	Intermediate Similarity	NPD7266	Discontinued
0.753	Intermediate Similarity	NPD7819	Suspended
0.7486	Intermediate Similarity	NPD6559	Discontinued
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3817	Phase 2
0.7484	Intermediate Similarity	NPD6674	Discontinued
0.7471	Intermediate Similarity	NPD7074	Phase 3
0.7471	Intermediate Similarity	NPD8127	Discontinued
0.7451	Intermediate Similarity	NPD3027	Phase 3
0.7427	Intermediate Similarity	NPD7229	Phase 3
0.7425	Intermediate Similarity	NPD8455	Phase 2
0.7423	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7054	Approved
0.738	Intermediate Similarity	NPD7680	Approved
0.7371	Intermediate Similarity	NPD7472	Approved
0.736	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7808	Phase 3
0.7342	Intermediate Similarity	NPD3748	Approved
0.7321	Intermediate Similarity	NPD1465	Phase 2
0.732	Intermediate Similarity	NPD3018	Phase 2
0.7317	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1613	Approved
0.7288	Intermediate Similarity	NPD7685	Pre-registration
0.7283	Intermediate Similarity	NPD3926	Phase 2
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7262	Intermediate Similarity	NPD1934	Approved
0.7258	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD919	Approved
0.7247	Intermediate Similarity	NPD7549	Discontinued
0.7247	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6166	Phase 2
0.7241	Intermediate Similarity	NPD5283	Phase 1
0.7241	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7768	Phase 2
0.7232	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2981	Phase 2
0.7207	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD8312	Approved
0.7193	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7251	Discontinued
0.7188	Intermediate Similarity	NPD2438	Suspended
0.7181	Intermediate Similarity	NPD5691	Approved
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2983	Phase 2
0.7171	Intermediate Similarity	NPD2982	Phase 2
0.7162	Intermediate Similarity	NPD5536	Phase 2
0.7161	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD5005	Approved
0.7143	Intermediate Similarity	NPD5006	Approved
0.7135	Intermediate Similarity	NPD6797	Phase 2
0.7135	Intermediate Similarity	NPD3882	Suspended
0.712	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3750	Approved
0.7097	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7075	Discontinued
0.7089	Intermediate Similarity	NPD4060	Phase 1
0.7086	Intermediate Similarity	NPD5242	Approved
0.7081	Intermediate Similarity	NPD2796	Approved
0.7076	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5353	Approved
0.7073	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7097	Phase 1
0.7062	Intermediate Similarity	NPD3751	Discontinued
0.7049	Intermediate Similarity	NPD6843	Phase 3
0.7049	Intermediate Similarity	NPD6841	Approved
0.7049	Intermediate Similarity	NPD6842	Approved
0.7048	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6355	Discontinued
0.7037	Intermediate Similarity	NPD5762	Approved
0.7037	Intermediate Similarity	NPD5763	Approved
0.7029	Intermediate Similarity	NPD3787	Discontinued
0.7022	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4420	Approved
0.7018	Intermediate Similarity	NPD2801	Approved
0.7012	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8151	Discontinued
0.7	Intermediate Similarity	NPD7411	Suspended
0.6994	Remote Similarity	NPD3749	Approved
0.6994	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6799	Approved
0.6982	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7458	Discontinued
0.6982	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2979	Phase 3
0.6977	Remote Similarity	NPD5402	Approved
0.6971	Remote Similarity	NPD6959	Discontinued
0.6971	Remote Similarity	NPD1247	Approved
0.697	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6190	Approved
0.6962	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD6801	Discontinued
0.6951	Remote Similarity	NPD1652	Phase 2
0.6949	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2532	Approved
0.6946	Remote Similarity	NPD2533	Approved
0.6946	Remote Similarity	NPD2534	Approved
0.6941	Remote Similarity	NPD4380	Phase 2
0.6941	Remote Similarity	NPD6599	Discontinued
0.6941	Remote Similarity	NPD7028	Phase 2
0.6937	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5124	Phase 1
0.6928	Remote Similarity	NPD1610	Phase 2
0.6918	Remote Similarity	NPD8032	Phase 2
0.6909	Remote Similarity	NPD7466	Approved
0.6909	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4110	Phase 3
0.6908	Remote Similarity	NPD4626	Approved
0.6902	Remote Similarity	NPD8434	Phase 2
0.6901	Remote Similarity	NPD6385	Approved
0.6901	Remote Similarity	NPD6386	Approved
0.6899	Remote Similarity	NPD7095	Approved
0.6899	Remote Similarity	NPD4625	Phase 3
0.6886	Remote Similarity	NPD4357	Discontinued
0.6879	Remote Similarity	NPD2861	Phase 2
0.6875	Remote Similarity	NPD4140	Approved
0.6871	Remote Similarity	NPD3539	Phase 1
0.6864	Remote Similarity	NPD920	Approved
0.6864	Remote Similarity	NPD5403	Approved
0.6855	Remote Similarity	NPD3764	Approved
0.6854	Remote Similarity	NPD4481	Phase 3
0.6848	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5401	Approved
0.6842	Remote Similarity	NPD1357	Approved
0.6839	Remote Similarity	NPD5327	Phase 3
0.6839	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6832	Phase 2
0.6833	Remote Similarity	NPD8156	Discontinued
0.6832	Remote Similarity	NPD3657	Discovery
0.6829	Remote Similarity	NPD3540	Phase 1
0.6828	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1358	Approved
0.6826	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7124	Phase 2
0.6824	Remote Similarity	NPD5535	Approved
0.6821	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD422	Phase 1
0.6818	Remote Similarity	NPD1611	Approved
0.6818	Remote Similarity	NPD1281	Approved
0.6813	Remote Similarity	NPD6233	Phase 2
0.681	Remote Similarity	NPD4108	Discontinued
0.6807	Remote Similarity	NPD4628	Phase 3
0.6807	Remote Similarity	NPD7003	Approved
0.6807	Remote Similarity	NPD8166	Discontinued
0.6805	Remote Similarity	NPD6273	Approved
0.6802	Remote Similarity	NPD5089	Approved
0.6802	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5090	Approved
0.6786	Remote Similarity	NPD1511	Approved
0.6782	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD8251	Approved
0.6778	Remote Similarity	NPD8099	Discontinued
0.6778	Remote Similarity	NPD8252	Approved
0.677	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3620	Phase 2
0.6768	Remote Similarity	NPD2935	Discontinued
0.6763	Remote Similarity	NPD3384	Approved
0.6763	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3383	Approved
0.6763	Remote Similarity	NPD3382	Approved
0.6759	Remote Similarity	NPD3134	Approved
0.6752	Remote Similarity	NPD3267	Approved
0.6752	Remote Similarity	NPD2797	Approved
0.6752	Remote Similarity	NPD3266	Approved
0.6747	Remote Similarity	NPD1243	Approved
0.6747	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD5585	Approved
0.673	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD230	Phase 1
0.6726	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4585	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