NPASS Compound

Structure

NPC281780 OpenBabel07101718292D 32 34 0 0 1 0 0 0 0 0999 V2000 1.6136 -5.8308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0806 -6.1909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2579 1.4565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9013 -1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8958 -1.9886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4546 -4.5436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0823 -0.1615 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 0.0388 -2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6625 -5.5218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4836 -1.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0768 -0.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4965 -4.2346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4128 0.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4781 -1.2841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2396 -4.9037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -1.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6646 0.5430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7044 -3.2564 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 7 2 0 0 0 0 5 16 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 15 1 0 0 0 0 9 24 1 0 0 0 0 10 16 1 0 0 0 0 11 16 2 0 0 0 0 11 22 1 0 0 0 0 12 17 2 0 0 0 0 12 23 1 0 0 0 0 13 18 1 0 0 0 0 13 32 1 0 0 0 0 14 31 1 0 0 0 0 18 10 1 1 0 0 0 18 19 1 0 0 0 0 19 14 1 1 0 0 0 19 25 1 0 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 21 23 2 0 0 0 0 21 27 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 28 2 0 0 0 0 24 31 1 0 0 0 0 25 17 1 6 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.21
Volume:	458.363
LogP:	4.254
LogD:	3.827
LogS:	-4.671
# Rotatable Bonds:	10
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	3.618
Fsp3:	0.48
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.757
MDCK Permeability:	2.1401623598649167e-05
Pgp-inhibitor:	0.196
Pgp-substrate:	0.087
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.072

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	97.6446762084961%
Volume Distribution (VD):	0.45
Pgp-substrate:	2.317209005355835%

ADMET: Metabolism

CYP1A2-inhibitor:	0.136
CYP1A2-substrate:	0.536
CYP2C19-inhibitor:	0.828
CYP2C19-substrate:	0.512
CYP2C9-inhibitor:	0.892
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.824
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.737
CYP3A4-substrate:	0.727

ADMET: Excretion

Clearance (CL):	13.2
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.18
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.856
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.249
Maximum Recommended Daily Dose:	0.5
Skin Sensitization:	0.942
Carcinogencity:	0.173
Eye Corrosion:	0.004
Eye Irritation:	0.72
Respiratory Toxicity:	0.561

Download Data

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

Natural Product: NPC281780

Natural Product ID:	NPC281780
*Common Name:**	(+)-9'-Isovaleroxylariciresinol
IUPAC Name:	[(2S,3R,4R)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl 3-methylbutanoate
Synonyms:	(+)-9'-Isovaleroxylariciresinol
Standard InCHIKey:	VOGRFGIBINTSKJ-XHNVNVPESA-N
Standard InCHI:	InChI=1S/C25H32O7/c1-15(2)9-24(28)31-14-19-18(10-16-5-7-20(26)22(11-16)29-3)13-32-25(19)17-6-8-21(27)23(12-17)30-4/h5-8,11-12,15,18-19,25-27H,9-10,13-14H2,1-4H3/t18-,19-,25+/m0/s1
SMILES:	CC(C)CC(=O)OC[C@H]1[C@@H](Cc2ccc(c(c2)OC)O)CO[C@@H]1c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098920
PubChem CID:	46211187
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003422] 7,9'-epoxylignans

*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
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18760601]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245261]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20151678]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	bark	n.a.	PMID[21875114]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434131]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26247834]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30579794]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	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	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
PROTEIN COMPLEX	100

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	5300.0	nM	PMID[520726]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8100.0	nM	PMID[520726]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	=	4900.0	nM	PMID[520727]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	=	9100.0	nM	PMID[520727]

☑ 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 NPC281780 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	283
0.1-0.2	1065
0.2-0.3	2882
0.3-0.4	6704
0.4-0.5	11860
0.5-0.6	4212
0.6-0.7	9263
0.7-0.8	5053
0.8-0.85	1051
0.85-0.9	237
0.9-0.95	83
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9769	High Similarity	NPC67247
0.9621	High Similarity	NPC471988
0.9481	High Similarity	NPC100675
0.9348	High Similarity	NPC223185
0.9313	High Similarity	NPC92164
0.9313	High Similarity	NPC77040
0.9313	High Similarity	NPC42300
0.9313	High Similarity	NPC174495
0.9313	High Similarity	NPC145305
0.9313	High Similarity	NPC257582
0.9313	High Similarity	NPC187998
0.9313	High Similarity	NPC64201
0.9313	High Similarity	NPC242807
0.9313	High Similarity	NPC241522
0.9313	High Similarity	NPC153739
0.9308	High Similarity	NPC11258
0.9308	High Similarity	NPC129570
0.9308	High Similarity	NPC128208
0.9308	High Similarity	NPC282703
0.9308	High Similarity	NPC21867
0.9308	High Similarity	NPC184733
0.9308	High Similarity	NPC45774
0.927	High Similarity	NPC131971
0.927	High Similarity	NPC253481
0.927	High Similarity	NPC31751
0.927	High Similarity	NPC253722
0.927	High Similarity	NPC67467
0.9242	High Similarity	NPC228346
0.9242	High Similarity	NPC40432
0.9242	High Similarity	NPC277804
0.9242	High Similarity	NPC7171
0.9242	High Similarity	NPC158079
0.9242	High Similarity	NPC161557
0.9242	High Similarity	NPC27843
0.9242	High Similarity	NPC115207
0.9237	High Similarity	NPC475875
0.9203	High Similarity	NPC106920
0.9203	High Similarity	NPC273657
0.9179	High Similarity	NPC176814
0.9179	High Similarity	NPC4982
0.9179	High Similarity	NPC68779
0.9179	High Similarity	NPC300776
0.9179	High Similarity	NPC5310
0.9173	High Similarity	NPC181049
0.9173	High Similarity	NPC207400
0.916	High Similarity	NPC470084
0.9149	High Similarity	NPC236166
0.9124	High Similarity	NPC147379
0.9104	High Similarity	NPC158331
0.9084	High Similarity	NPC118533
0.9084	High Similarity	NPC165045
0.9071	High Similarity	NPC163898
0.9065	High Similarity	NPC477696
0.9065	High Similarity	NPC477697
0.9065	High Similarity	NPC470811
0.9037	High Similarity	NPC135127
0.9037	High Similarity	NPC287745
0.903	High Similarity	NPC204215
0.903	High Similarity	NPC471505
0.903	High Similarity	NPC175067
0.903	High Similarity	NPC4940
0.9014	High Similarity	NPC102934
0.9014	High Similarity	NPC252402
0.9008	High Similarity	NPC206882
0.8971	High Similarity	NPC99572
0.8971	High Similarity	NPC184938
0.8971	High Similarity	NPC113295
0.8971	High Similarity	NPC101624
0.8971	High Similarity	NPC126409
0.8971	High Similarity	NPC135777
0.8971	High Similarity	NPC142547
0.8966	High Similarity	NPC61604
0.8966	High Similarity	NPC115466
0.8966	High Similarity	NPC245615
0.8966	High Similarity	NPC299706
0.8951	High Similarity	NPC125570
0.8939	High Similarity	NPC5428
0.8936	High Similarity	NPC477702
0.8931	High Similarity	NPC148627
0.8923	High Similarity	NPC31344
0.8923	High Similarity	NPC317769
0.8921	High Similarity	NPC472711
0.8913	High Similarity	NPC193666
0.8913	High Similarity	NPC123526
0.8913	High Similarity	NPC88640
0.8905	High Similarity	NPC29799
0.8905	High Similarity	NPC209985
0.8905	High Similarity	NPC477939
0.8905	High Similarity	NPC90431
0.8905	High Similarity	NPC177160
0.8905	High Similarity	NPC54743
0.8905	High Similarity	NPC156502
0.8905	High Similarity	NPC263367
0.8905	High Similarity	NPC10737
0.8905	High Similarity	NPC77861
0.8897	High Similarity	NPC326095
0.8897	High Similarity	NPC476434
0.8897	High Similarity	NPC49603
0.8897	High Similarity	NPC244983
0.8897	High Similarity	NPC187616
0.8897	High Similarity	NPC267091
0.8897	High Similarity	NPC471942
0.8897	High Similarity	NPC193026
0.8889	High Similarity	NPC106739
0.8873	High Similarity	NPC212890
0.8872	High Similarity	NPC474178
0.8872	High Similarity	NPC252307
0.8872	High Similarity	NPC245826
0.8857	High Similarity	NPC476356
0.8857	High Similarity	NPC52664
0.8844	High Similarity	NPC38699
0.8841	High Similarity	NPC126206
0.8841	High Similarity	NPC308976
0.8836	High Similarity	NPC473236
0.8836	High Similarity	NPC474606
0.8832	High Similarity	NPC24490
0.8832	High Similarity	NPC141765
0.8832	High Similarity	NPC470990
0.8832	High Similarity	NPC165155
0.8832	High Similarity	NPC34103
0.8828	High Similarity	NPC243891
0.8819	High Similarity	NPC145569
0.8819	High Similarity	NPC216223
0.8815	High Similarity	NPC476345
0.8815	High Similarity	NPC474017
0.8797	High Similarity	NPC118787
0.8797	High Similarity	NPC319625
0.8797	High Similarity	NPC183181
0.8797	High Similarity	NPC163332
0.8797	High Similarity	NPC147821
0.8797	High Similarity	NPC292056
0.8797	High Similarity	NPC111247
0.8797	High Similarity	NPC41706
0.8794	High Similarity	NPC470950
0.8794	High Similarity	NPC477898
0.8794	High Similarity	NPC185307
0.8786	High Similarity	NPC282291
0.8786	High Similarity	NPC166137
0.8786	High Similarity	NPC29599
0.8786	High Similarity	NPC471414
0.8784	High Similarity	NPC228357
0.8784	High Similarity	NPC163635
0.8779	High Similarity	NPC471693
0.8779	High Similarity	NPC280704
0.8779	High Similarity	NPC473451
0.8769	High Similarity	NPC65933
0.8769	High Similarity	NPC126935
0.8769	High Similarity	NPC312713
0.8769	High Similarity	NPC172676
0.8769	High Similarity	NPC57268
0.8769	High Similarity	NPC216929
0.8768	High Similarity	NPC471664
0.8768	High Similarity	NPC120852
0.8768	High Similarity	NPC471665
0.8768	High Similarity	NPC471719
0.8767	High Similarity	NPC471154
0.8767	High Similarity	NPC478268
0.8759	High Similarity	NPC229882
0.8759	High Similarity	NPC158635
0.8741	High Similarity	NPC173308
0.8741	High Similarity	NPC3982
0.8741	High Similarity	NPC181079
0.8741	High Similarity	NPC275950
0.8741	High Similarity	NPC474054
0.8732	High Similarity	NPC284881
0.8732	High Similarity	NPC470235
0.8732	High Similarity	NPC27159
0.8732	High Similarity	NPC474444
0.8732	High Similarity	NPC129417
0.8732	High Similarity	NPC93433
0.8732	High Similarity	NPC84181
0.8732	High Similarity	NPC264706
0.8732	High Similarity	NPC283995
0.8732	High Similarity	NPC87883
0.8723	High Similarity	NPC253878
0.8722	High Similarity	NPC213552
0.8722	High Similarity	NPC178284
0.8722	High Similarity	NPC120225
0.8722	High Similarity	NPC191037
0.8722	High Similarity	NPC58607
0.8716	High Similarity	NPC238834
0.8714	High Similarity	NPC254759
0.8714	High Similarity	NPC309124
0.8714	High Similarity	NPC184797
0.8714	High Similarity	NPC160283
0.8714	High Similarity	NPC289690
0.8714	High Similarity	NPC288452
0.8714	High Similarity	NPC177868
0.8712	High Similarity	NPC131747
0.8712	High Similarity	NPC34902
0.8712	High Similarity	NPC18449
0.8712	High Similarity	NPC257682
0.8712	High Similarity	NPC146355
0.8712	High Similarity	NPC121783
0.8707	High Similarity	NPC178574
0.8707	High Similarity	NPC65591
0.8707	High Similarity	NPC115203
0.8705	High Similarity	NPC474039
0.8702	High Similarity	NPC85488
0.8699	High Similarity	NPC475756

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 NPC281780 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	719
0.2-0.3	1608
0.3-0.4	2477
0.4-0.5	2117
0.5-0.6	1073
0.6-0.7	757
0.7-0.8	154
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD3027	Phase 3
0.8421	Intermediate Similarity	NPD6234	Discontinued
0.8222	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD37	Approved
0.817	Intermediate Similarity	NPD4967	Phase 2
0.817	Intermediate Similarity	NPD4966	Approved
0.817	Intermediate Similarity	NPD4965	Approved
0.8165	Intermediate Similarity	NPD7228	Approved
0.8163	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD6355	Discontinued
0.8125	Intermediate Similarity	NPD7266	Discontinued
0.8085	Intermediate Similarity	NPD1613	Approved
0.8085	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD4060	Phase 1
0.8082	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD4110	Phase 3
0.8077	Intermediate Similarity	NPD5283	Phase 1
0.8	Intermediate Similarity	NPD7095	Approved
0.7972	Intermediate Similarity	NPD6653	Approved
0.7941	Intermediate Similarity	NPD3705	Approved
0.7929	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD228	Approved
0.7879	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2861	Phase 2
0.7857	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1934	Approved
0.7848	Intermediate Similarity	NPD7199	Phase 2
0.7838	Intermediate Similarity	NPD4628	Phase 3
0.7832	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD3620	Phase 2
0.7821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6190	Approved
0.7769	Intermediate Similarity	NPD3022	Approved
0.7769	Intermediate Similarity	NPD3021	Approved
0.7762	Intermediate Similarity	NPD6233	Phase 2
0.7755	Intermediate Similarity	NPD5763	Approved
0.7755	Intermediate Similarity	NPD5762	Approved
0.7754	Intermediate Similarity	NPD1608	Approved
0.775	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7685	Pre-registration
0.7707	Intermediate Similarity	NPD3882	Suspended
0.7704	Intermediate Similarity	NPD5536	Phase 2
0.7692	Intermediate Similarity	NPD6798	Discontinued
0.7692	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7240	Approved
0.7625	Intermediate Similarity	NPD8127	Discontinued
0.7607	Intermediate Similarity	NPD3818	Discontinued
0.7605	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8166	Discontinued
0.7597	Intermediate Similarity	NPD1653	Approved
0.7591	Intermediate Similarity	NPD5585	Approved
0.7591	Intermediate Similarity	NPD1357	Approved
0.758	Intermediate Similarity	NPD2801	Approved
0.7568	Intermediate Similarity	NPD2438	Suspended
0.7552	Intermediate Similarity	NPD4908	Phase 1
0.7551	Intermediate Similarity	NPD7097	Phase 1
0.7546	Intermediate Similarity	NPD7473	Discontinued
0.7536	Intermediate Similarity	NPD17	Approved
0.7534	Intermediate Similarity	NPD230	Phase 1
0.7533	Intermediate Similarity	NPD6674	Discontinued
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3817	Phase 2
0.7518	Intermediate Similarity	NPD1283	Approved
0.7517	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6004	Phase 3
0.7517	Intermediate Similarity	NPD6005	Phase 3
0.7517	Intermediate Similarity	NPD4062	Phase 3
0.7517	Intermediate Similarity	NPD6002	Phase 3
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7484	Intermediate Similarity	NPD3686	Approved
0.7484	Intermediate Similarity	NPD3687	Approved
0.7483	Intermediate Similarity	NPD5736	Approved
0.7482	Intermediate Similarity	NPD3847	Discontinued
0.7469	Intermediate Similarity	NPD6232	Discontinued
0.7467	Intermediate Similarity	NPD5958	Discontinued
0.7466	Intermediate Similarity	NPD4140	Approved
0.7466	Intermediate Similarity	NPD1558	Phase 1
0.7466	Intermediate Similarity	NPD2979	Phase 3
0.7455	Intermediate Similarity	NPD5844	Phase 1
0.7455	Intermediate Similarity	NPD7054	Approved
0.745	Intermediate Similarity	NPD6032	Approved
0.745	Intermediate Similarity	NPD2935	Discontinued
0.7448	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2982	Phase 2
0.7447	Intermediate Similarity	NPD2983	Phase 2
0.7429	Intermediate Similarity	NPD1610	Phase 2
0.7426	Intermediate Similarity	NPD7157	Approved
0.7417	Intermediate Similarity	NPD4237	Approved
0.7417	Intermediate Similarity	NPD4236	Phase 3
0.741	Intermediate Similarity	NPD7472	Approved
0.7376	Intermediate Similarity	NPD2981	Phase 2
0.7361	Intermediate Similarity	NPD9494	Approved
0.7361	Intermediate Similarity	NPD3018	Phase 2
0.7358	Intermediate Similarity	NPD8455	Phase 2
0.7358	Intermediate Similarity	NPD2978	Approved
0.7358	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2977	Approved
0.7358	Intermediate Similarity	NPD1465	Phase 2
0.7355	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4534	Discontinued
0.7346	Intermediate Similarity	NPD5494	Approved
0.7343	Intermediate Similarity	NPD2797	Approved
0.7343	Intermediate Similarity	NPD6362	Approved
0.7342	Intermediate Similarity	NPD6385	Approved
0.7342	Intermediate Similarity	NPD6386	Approved
0.7338	Intermediate Similarity	NPD1511	Approved
0.7338	Intermediate Similarity	NPD4357	Discontinued
0.7333	Intermediate Similarity	NPD5535	Approved
0.7333	Intermediate Similarity	NPD7843	Approved
0.7329	Intermediate Similarity	NPD7075	Discontinued
0.7329	Intermediate Similarity	NPD3764	Approved
0.7326	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4359	Approved
0.7324	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1535	Discovery
0.7305	Intermediate Similarity	NPD1281	Approved
0.7303	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3060	Approved
0.7297	Intermediate Similarity	NPD4340	Discontinued
0.7297	Intermediate Similarity	NPD5735	Approved
0.7293	Intermediate Similarity	NPD2684	Approved
0.7292	Intermediate Similarity	NPD5647	Approved
0.7288	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4626	Approved
0.7286	Intermediate Similarity	NPD1778	Approved
0.7285	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1375	Discontinued
0.7279	Intermediate Similarity	NPD6663	Approved
0.7278	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5058	Phase 3
0.7273	Intermediate Similarity	NPD6666	Approved
0.7273	Intermediate Similarity	NPD6667	Approved
0.7267	Intermediate Similarity	NPD5588	Approved
0.7266	Intermediate Similarity	NPD1894	Discontinued
0.7262	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7229	Phase 3
0.7255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6331	Phase 2
0.7254	Intermediate Similarity	NPD1481	Phase 2
0.725	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1512	Approved
0.7237	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3496	Discontinued
0.7233	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7680	Approved
0.7219	Intermediate Similarity	NPD7251	Discontinued
0.7218	Intermediate Similarity	NPD1358	Approved
0.7215	Intermediate Similarity	NPD3455	Phase 2
0.7214	Intermediate Similarity	NPD5691	Approved
0.7211	Intermediate Similarity	NPD3268	Approved
0.7208	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4536	Approved
0.72	Intermediate Similarity	NPD4538	Approved
0.72	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD422	Phase 1
0.7183	Intermediate Similarity	NPD1091	Approved
0.7181	Intermediate Similarity	NPD447	Suspended
0.7179	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD2532	Approved
0.7179	Intermediate Similarity	NPD2534	Approved
0.7176	Intermediate Similarity	NPD7808	Phase 3
0.7174	Intermediate Similarity	NPD6671	Approved
0.717	Intermediate Similarity	NPD4380	Phase 2
0.717	Intermediate Similarity	NPD7028	Phase 2
0.7162	Intermediate Similarity	NPD4870	Approved
0.7162	Intermediate Similarity	NPD8032	Phase 2
0.716	Intermediate Similarity	NPD6797	Phase 2
0.7153	Intermediate Similarity	NPD8651	Approved
0.7152	Intermediate Similarity	NPD4210	Discontinued
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD3134	Approved
0.7134	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6273	Approved
0.7124	Intermediate Similarity	NPD2424	Discontinued
0.7118	Intermediate Similarity	NPD6559	Discontinued
0.7117	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6799	Approved
0.7114	Intermediate Similarity	NPD2238	Phase 2
0.7114	Intermediate Similarity	NPD825	Approved
0.7114	Intermediate Similarity	NPD826	Approved
0.7108	Intermediate Similarity	NPD5242	Approved
0.7107	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2161	Phase 2
0.7105	Intermediate Similarity	NPD6100	Approved
0.7105	Intermediate Similarity	NPD2531	Phase 2
0.7105	Intermediate Similarity	NPD6099	Approved
0.7103	Intermediate Similarity	NPD987	Approved
0.7103	Intermediate Similarity	NPD3094	Phase 2
0.7099	Intermediate Similarity	NPD5353	Approved
0.7099	Intermediate Similarity	NPD6374	Clinical (unspecified phase)

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