NPASS Compound

Structure

NPC476411 OpenBabel07101719122D 33 36 0 0 1 0 0 0 0 0999 V2000 -3.1358 -1.1114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6672 -0.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6376 -1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3030 -0.5861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2652 0.8428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9257 0.3536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1921 1.9066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6214 -1.6366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0854 0.3742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8223 0.1998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0887 1.7528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9391 -1.2427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4416 -0.5296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7878 -1.3645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6106 1.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0961 -0.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0987 -0.1276 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4038 0.8994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9391 -0.4548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6214 -0.0609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7878 -0.4548 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5756 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5756 0.9097 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7878 1.3645 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9097 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.8194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2115 -0.3286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3634 -0.4548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3634 1.3645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7878 2.2742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6081 0.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7878 1.3645 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 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 9 1 0 0 0 0 5 15 1 0 0 0 0 6 10 1 0 0 0 0 6 15 2 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 26 1 0 0 0 0 17 27 1 1 0 0 0 18 31 1 0 0 0 0 19 20 2 0 0 0 0 19 32 1 0 0 0 0 20 31 1 0 0 0 0 21 14 1 1 0 0 0 21 22 1 0 0 0 0 21 33 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 6 0 0 0 23 24 1 0 0 0 0 23 29 1 1 0 0 0 24 25 1 0 0 0 0 24 30 1 6 0 0 0 25 32 1 6 0 0 0 25 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.21
Volume:	461.233
LogP:	2.637
LogD:	2.542
LogS:	-4.024
# Rotatable Bonds:	3
TPSA:	128.84
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	5.712
Fsp3:	0.52
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.519
MDCK Permeability:	1.6167041394510306e-05
Pgp-inhibitor:	0.323
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.324
20% Bioavailability (F20%):	0.918
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	95.41094207763672%
Volume Distribution (VD):	0.504
Pgp-substrate:	1.9925605058670044%

ADMET: Metabolism

CYP1A2-inhibitor:	0.202
CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.169
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.255
CYP2C9-substrate:	0.706
CYP2D6-inhibitor:	0.444
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	7.795
Half-life (T1/2):	0.486

ADMET: Toxicity

hERG Blockers:	0.366
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.356
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.913
Carcinogencity:	0.663
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.227

Download Data

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

Natural Product: NPC476411

Natural Product ID:	NPC476411
*Common Name:**	Aceroside I
IUPAC Name:	n.a.
Synonyms:	Aceroside I
Standard InCHIKey:	LYWCEZCFIUWAGY-CHTWLVHHSA-N
Standard InCHI:	InChI=1S/C25H32O8/c26-14-21-22(28)23(29)24(30)25(33-21)32-19-12-8-16-3-1-2-4-17(27)9-5-15-6-10-18(11-7-15)31-20(19)13-16/h6-8,10-13,17,21-30H,1-5,9,14H2/t17-,21+,22+,23-,24+,25-/m0/s1
SMILES:	C1CCC2=CC(=C(C=C2)OC3C(C(C(C(O3)CO)O)O)O)OC4=CC=C(CCC(C1)O)C=C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL597938
PubChem CID:	24896756
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

*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
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	Japan	n.a.	PMID[12542351]
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21550801]
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	Inhibition	=	18.3	%	PMID[524008]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	15.0	%	PMID[524008]

☑ 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 NPC476411 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	406
0.1-0.2	1501
0.2-0.3	3989
0.3-0.4	10391
0.4-0.5	8154
0.5-0.6	5141
0.6-0.7	8091
0.7-0.8	3883
0.8-0.85	778
0.85-0.9	266
0.9-0.95	84
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9844	High Similarity	NPC187194
0.9621	High Similarity	NPC106944
0.9618	High Similarity	NPC138738
0.9618	High Similarity	NPC470413
0.9609	High Similarity	NPC9912
0.9542	High Similarity	NPC199459
0.9542	High Similarity	NPC177035
0.9542	High Similarity	NPC52277
0.9531	High Similarity	NPC80600
0.9531	High Similarity	NPC472024
0.9478	High Similarity	NPC246947
0.9453	High Similarity	NPC26653
0.9453	High Similarity	NPC270849
0.9407	High Similarity	NPC46092
0.9407	High Similarity	NPC470950
0.9407	High Similarity	NPC185307
0.9403	High Similarity	NPC76871
0.9403	High Similarity	NPC469661
0.9398	High Similarity	NPC156376
0.9375	High Similarity	NPC302378
0.9338	High Similarity	NPC129417
0.9338	High Similarity	NPC470235
0.9338	High Similarity	NPC471063
0.9338	High Similarity	NPC471667
0.9338	High Similarity	NPC217635
0.9338	High Similarity	NPC283995
0.9338	High Similarity	NPC79429
0.9333	High Similarity	NPC189115
0.9333	High Similarity	NPC476356
0.9333	High Similarity	NPC60249
0.9333	High Similarity	NPC469559
0.9302	High Similarity	NPC248355
0.9302	High Similarity	NPC166040
0.927	High Similarity	NPC38041
0.927	High Similarity	NPC279298
0.927	High Similarity	NPC476301
0.927	High Similarity	NPC43508
0.927	High Similarity	NPC475096
0.927	High Similarity	NPC22150
0.927	High Similarity	NPC18979
0.9259	High Similarity	NPC472711
0.9259	High Similarity	NPC471908
0.9242	High Similarity	NPC35731
0.9203	High Similarity	NPC276753
0.9203	High Similarity	NPC205796
0.9203	High Similarity	NPC112861
0.9197	High Similarity	NPC25292
0.9197	High Similarity	NPC473045
0.9179	High Similarity	NPC304152
0.9179	High Similarity	NPC59324
0.9179	High Similarity	NPC65530
0.9173	High Similarity	NPC470236
0.9167	High Similarity	NPC69513
0.9167	High Similarity	NPC215833
0.9167	High Similarity	NPC25821
0.916	High Similarity	NPC65942
0.916	High Similarity	NPC248307
0.9137	High Similarity	NPC213074
0.9137	High Similarity	NPC224674
0.9137	High Similarity	NPC227902
0.9137	High Similarity	NPC39657
0.9137	High Similarity	NPC193473
0.9137	High Similarity	NPC114505
0.9137	High Similarity	NPC275284
0.9137	High Similarity	NPC15956
0.9137	High Similarity	NPC31325
0.913	High Similarity	NPC469586
0.9124	High Similarity	NPC477898
0.9124	High Similarity	NPC113680
0.9124	High Similarity	NPC473044
0.9124	High Similarity	NPC278961
0.9111	High Similarity	NPC212770
0.9111	High Similarity	NPC98777
0.9104	High Similarity	NPC242028
0.9104	High Similarity	NPC164857
0.9104	High Similarity	NPC203230
0.9098	High Similarity	NPC13745
0.9098	High Similarity	NPC48863
0.9098	High Similarity	NPC251981
0.9091	High Similarity	NPC254275
0.9091	High Similarity	NPC162093
0.9077	High Similarity	NPC72529
0.9071	High Similarity	NPC116229
0.9071	High Similarity	NPC270751
0.9065	High Similarity	NPC190714
0.9065	High Similarity	NPC125755
0.9065	High Similarity	NPC99515
0.9058	High Similarity	NPC168579
0.9058	High Similarity	NPC76176
0.9058	High Similarity	NPC138227
0.9058	High Similarity	NPC84181
0.9058	High Similarity	NPC469313
0.9051	High Similarity	NPC302506
0.9051	High Similarity	NPC475084
0.9051	High Similarity	NPC472714
0.9051	High Similarity	NPC48309
0.9051	High Similarity	NPC5262
0.9023	High Similarity	NPC49074
0.9015	High Similarity	NPC473412
0.9015	High Similarity	NPC469698
0.9008	High Similarity	NPC86030
0.9008	High Similarity	NPC307110
0.9008	High Similarity	NPC5851
0.9007	High Similarity	NPC55158
0.9007	High Similarity	NPC44452
0.9007	High Similarity	NPC286235
0.9007	High Similarity	NPC51328
0.9	High Similarity	NPC79715
0.9	High Similarity	NPC264900
0.9	High Similarity	NPC231607
0.9	High Similarity	NPC108659
0.8993	High Similarity	NPC286245
0.8993	High Similarity	NPC161700
0.8993	High Similarity	NPC277867
0.8993	High Similarity	NPC272619
0.8986	High Similarity	NPC252169
0.8986	High Similarity	NPC37793
0.8986	High Similarity	NPC478239
0.8978	High Similarity	NPC186406
0.8963	High Similarity	NPC25695
0.8963	High Similarity	NPC172818
0.8955	High Similarity	NPC470881
0.8955	High Similarity	NPC87696
0.8947	High Similarity	NPC85799
0.8947	High Similarity	NPC26080
0.8947	High Similarity	NPC299144
0.8947	High Similarity	NPC303422
0.8947	High Similarity	NPC165686
0.8944	High Similarity	NPC158635
0.8944	High Similarity	NPC229882
0.8944	High Similarity	NPC475224
0.8944	High Similarity	NPC98624
0.8939	High Similarity	NPC477804
0.8936	High Similarity	NPC175976
0.8936	High Similarity	NPC280945
0.8936	High Similarity	NPC248132
0.8936	High Similarity	NPC130449
0.8931	High Similarity	NPC474178
0.8931	High Similarity	NPC245826
0.8931	High Similarity	NPC252307
0.8923	High Similarity	NPC94179
0.8921	High Similarity	NPC253015
0.8921	High Similarity	NPC179521
0.8921	High Similarity	NPC118385
0.8921	High Similarity	NPC472713
0.8921	High Similarity	NPC473046
0.8921	High Similarity	NPC232228
0.8921	High Similarity	NPC471065
0.8921	High Similarity	NPC472712
0.8921	High Similarity	NPC187774
0.8915	High Similarity	NPC94276
0.8915	High Similarity	NPC109822
0.8913	High Similarity	NPC477794
0.8913	High Similarity	NPC477800
0.8913	High Similarity	NPC140502
0.8913	High Similarity	NPC157816
0.8913	High Similarity	NPC477799
0.8906	High Similarity	NPC71090
0.8898	High Similarity	NPC198734
0.8898	High Similarity	NPC469412
0.8897	High Similarity	NPC477797
0.8897	High Similarity	NPC477798
0.8889	High Similarity	NPC101624
0.8889	High Similarity	NPC79957
0.8889	High Similarity	NPC184938
0.8889	High Similarity	NPC55040
0.8881	High Similarity	NPC294166
0.8881	High Similarity	NPC6836
0.8881	High Similarity	NPC263064
0.8881	High Similarity	NPC115022
0.8873	High Similarity	NPC95392
0.8873	High Similarity	NPC35877
0.8873	High Similarity	NPC106138
0.8873	High Similarity	NPC55715
0.8872	High Similarity	NPC475067
0.8872	High Similarity	NPC469613
0.8872	High Similarity	NPC166168
0.8872	High Similarity	NPC469625
0.8872	High Similarity	NPC30043
0.8872	High Similarity	NPC121376
0.8865	High Similarity	NPC15538
0.8865	High Similarity	NPC473480
0.8864	High Similarity	NPC184092
0.8857	High Similarity	NPC476869
0.8857	High Similarity	NPC476868
0.8857	High Similarity	NPC476866
0.8857	High Similarity	NPC100998
0.8857	High Similarity	NPC252292
0.8857	High Similarity	NPC34587
0.8857	High Similarity	NPC34927
0.8857	High Similarity	NPC476864
0.8857	High Similarity	NPC476382
0.8855	High Similarity	NPC183181
0.8855	High Similarity	NPC118787
0.8855	High Similarity	NPC163332
0.8855	High Similarity	NPC41706
0.8855	High Similarity	NPC111247
0.8855	High Similarity	NPC292056
0.8855	High Similarity	NPC319625
0.8855	High Similarity	NPC147821

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 NPC476411 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	826
0.2-0.3	1763
0.3-0.4	2768
0.4-0.5	1744
0.5-0.6	952
0.6-0.7	634
0.7-0.8	118
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD6674	Discontinued
0.8529	High Similarity	NPD1613	Approved
0.8529	High Similarity	NPD1612	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD3027	Phase 3
0.8429	Intermediate Similarity	NPD7266	Discontinued
0.8397	Intermediate Similarity	NPD1091	Approved
0.8235	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1653	Approved
0.8162	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD3705	Approved
0.8014	Intermediate Similarity	NPD5058	Phase 3
0.7987	Intermediate Similarity	NPD7074	Phase 3
0.7961	Intermediate Similarity	NPD8455	Phase 2
0.7925	Intermediate Similarity	NPD7054	Approved
0.7907	Intermediate Similarity	NPD7843	Approved
0.7899	Intermediate Similarity	NPD2861	Phase 2
0.7895	Intermediate Similarity	NPD1357	Approved
0.7875	Intermediate Similarity	NPD7472	Approved
0.7863	Intermediate Similarity	NPD7157	Approved
0.7862	Intermediate Similarity	NPD3818	Discontinued
0.7846	Intermediate Similarity	NPD5283	Phase 1
0.7832	Intermediate Similarity	NPD4538	Approved
0.7832	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD4536	Approved
0.7808	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5588	Approved
0.7778	Intermediate Similarity	NPD5960	Phase 3
0.7778	Intermediate Similarity	NPD37	Approved
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.775	Intermediate Similarity	NPD7228	Approved
0.7742	Intermediate Similarity	NPD4966	Approved
0.7742	Intermediate Similarity	NPD4967	Phase 2
0.7742	Intermediate Similarity	NPD4965	Approved
0.7734	Intermediate Similarity	NPD2684	Approved
0.773	Intermediate Similarity	NPD7808	Phase 3
0.7718	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7251	Discontinued
0.7643	Intermediate Similarity	NPD6234	Discontinued
0.7622	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD2982	Phase 2
0.7609	Intermediate Similarity	NPD2983	Phase 2
0.7607	Intermediate Similarity	NPD6797	Phase 2
0.7591	Intermediate Similarity	NPD1610	Phase 2
0.7589	Intermediate Similarity	NPD4908	Phase 1
0.7586	Intermediate Similarity	NPD7097	Phase 1
0.7574	Intermediate Similarity	NPD5846	Approved
0.7574	Intermediate Similarity	NPD6516	Phase 2
0.7562	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7240	Approved
0.7557	Intermediate Similarity	NPD228	Approved
0.7554	Intermediate Similarity	NPD8651	Approved
0.7551	Intermediate Similarity	NPD1375	Discontinued
0.7548	Intermediate Similarity	NPD1934	Approved
0.7536	Intermediate Similarity	NPD2981	Phase 2
0.7535	Intermediate Similarity	NPD7095	Approved
0.7518	Intermediate Similarity	NPD3018	Phase 2
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7685	Pre-registration
0.7448	Intermediate Similarity	NPD5735	Approved
0.7445	Intermediate Similarity	NPD5125	Phase 3
0.7445	Intermediate Similarity	NPD5126	Approved
0.7431	Intermediate Similarity	NPD6233	Phase 2
0.7426	Intermediate Similarity	NPD1548	Phase 1
0.7415	Intermediate Similarity	NPD4108	Discontinued
0.7407	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6166	Phase 2
0.7407	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2978	Approved
0.7389	Intermediate Similarity	NPD2977	Approved
0.7385	Intermediate Similarity	NPD290	Approved
0.7379	Intermediate Similarity	NPD3620	Phase 2
0.7379	Intermediate Similarity	NPD4060	Phase 1
0.7379	Intermediate Similarity	NPD1558	Phase 1
0.7379	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6798	Discontinued
0.7357	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6559	Discontinued
0.7343	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3817	Phase 2
0.7338	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6671	Approved
0.7333	Intermediate Similarity	NPD4162	Approved
0.7333	Intermediate Similarity	NPD4237	Approved
0.7333	Intermediate Similarity	NPD4236	Phase 3
0.7329	Intermediate Similarity	NPD6355	Discontinued
0.7315	Intermediate Similarity	NPD5762	Approved
0.7315	Intermediate Similarity	NPD5763	Approved
0.7303	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6331	Phase 2
0.7285	Intermediate Similarity	NPD4535	Phase 3
0.7285	Intermediate Similarity	NPD4110	Phase 3
0.7285	Intermediate Similarity	NPD4628	Phase 3
0.7285	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3787	Discontinued
0.7266	Intermediate Similarity	NPD291	Approved
0.7244	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5535	Approved
0.7237	Intermediate Similarity	NPD2677	Approved
0.7237	Intermediate Similarity	NPD6190	Approved
0.7234	Intermediate Similarity	NPD3685	Discontinued
0.7226	Intermediate Similarity	NPD5536	Phase 2
0.7222	Intermediate Similarity	NPD8127	Discontinued
0.7219	Intermediate Similarity	NPD1652	Phase 2
0.7219	Intermediate Similarity	NPD3060	Approved
0.7219	Intermediate Similarity	NPD5177	Phase 3
0.7215	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4340	Discontinued
0.7208	Intermediate Similarity	NPD4123	Phase 3
0.7203	Intermediate Similarity	NPD6584	Phase 3
0.72	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6842	Approved
0.7193	Intermediate Similarity	NPD6841	Approved
0.7193	Intermediate Similarity	NPD6843	Phase 3
0.7192	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3687	Approved
0.7179	Intermediate Similarity	NPD3686	Approved
0.7176	Intermediate Similarity	NPD968	Approved
0.7176	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4625	Phase 3
0.7171	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5772	Approved
0.717	Intermediate Similarity	NPD2801	Approved
0.717	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5773	Approved
0.7169	Intermediate Similarity	NPD5844	Phase 1
0.7163	Intermediate Similarity	NPD2231	Phase 2
0.7163	Intermediate Similarity	NPD2235	Phase 2
0.7162	Intermediate Similarity	NPD6653	Approved
0.7161	Intermediate Similarity	NPD52	Approved
0.7161	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7526	Approved
0.716	Intermediate Similarity	NPD8312	Approved
0.716	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1774	Approved
0.7143	Intermediate Similarity	NPD556	Approved
0.7143	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD3021	Approved
0.7124	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5327	Phase 3
0.7113	Intermediate Similarity	NPD4749	Approved
0.7097	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4380	Phase 2
0.7089	Intermediate Similarity	NPD4675	Approved
0.7089	Intermediate Similarity	NPD4678	Approved
0.7083	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4062	Phase 3
0.7067	Intermediate Similarity	NPD7033	Discontinued
0.7063	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1608	Approved
0.7039	Intermediate Similarity	NPD2424	Discontinued
0.7037	Intermediate Similarity	NPD7075	Discontinued
0.7032	Intermediate Similarity	NPD1511	Approved
0.7025	Intermediate Similarity	NPD4005	Discontinued
0.702	Intermediate Similarity	NPD2161	Phase 2
0.702	Intermediate Similarity	NPD6032	Approved
0.7007	Intermediate Similarity	NPD5718	Phase 2
0.7006	Intermediate Similarity	NPD2122	Discontinued
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3382	Approved
0.7	Intermediate Similarity	NPD3383	Approved
0.7	Intermediate Similarity	NPD3384	Approved
0.6993	Remote Similarity	NPD6582	Phase 2
0.6993	Remote Similarity	NPD6583	Phase 3
0.698	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1933	Approved
0.698	Remote Similarity	NPD5124	Phase 1
0.6975	Remote Similarity	NPD3882	Suspended
0.6974	Remote Similarity	NPD3540	Phase 1
0.697	Remote Similarity	NPD6071	Discontinued
0.697	Remote Similarity	NPD3051	Approved
0.6957	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1465	Phase 2
0.6957	Remote Similarity	NPD7819	Suspended
0.6951	Remote Similarity	NPD5494	Approved
0.6943	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1512	Approved
0.6939	Remote Similarity	NPD3180	Approved
0.6939	Remote Similarity	NPD3179	Approved
0.6933	Remote Similarity	NPD5604	Discontinued
0.6933	Remote Similarity	NPD6353	Approved
0.6929	Remote Similarity	NPD1894	Discontinued
0.6929	Remote Similarity	NPD1182	Approved
0.6928	Remote Similarity	NPD2970	Approved
0.6928	Remote Similarity	NPD2969	Approved
0.6927	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2563	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