NPASS Compound

Structure

NPC46591 OpenBabel07101718242D 30 34 0 0 1 0 0 0 0 0999 V2000 -8.9814 3.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1767 2.9451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3833 -0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2493 1.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1154 -0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 -0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3958 -1.0987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 1.2807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5202 0.7862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2493 0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5173 0.2862 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6038 -0.1205 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1154 1.7862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9814 0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9346 0.6226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9814 1.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1390 -1.7678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1154 2.7862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 2.0316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4346 1.4886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9325 -0.0228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9325 1.5952 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 12 1 0 0 0 0 4 12 2 0 0 0 0 4 16 1 0 0 0 0 5 12 1 0 0 0 0 5 18 2 0 0 0 0 6 13 2 0 0 0 0 6 17 1 0 0 0 0 7 13 1 0 0 0 0 7 19 2 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 10 29 1 0 0 0 0 11 28 1 0 0 0 0 11 30 1 0 0 0 0 14 3 1 1 0 0 0 14 15 1 0 0 0 0 15 8 1 1 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 22 2 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 19 28 1 0 0 0 0 20 13 1 6 0 0 0 20 26 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.15
Volume:	400.789
LogP:	2.882
LogD:	3.129
LogS:	-4.664
# Rotatable Bonds:	6
TPSA:	84.84
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.77
Synthetic Accessibility Score:	3.806
Fsp3:	0.455
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:	-4.784
MDCK Permeability:	3.925960845663212e-05
Pgp-inhibitor:	0.885
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	92.18938446044922%
Volume Distribution (VD):	0.6
Pgp-substrate:	4.506927490234375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.516
CYP1A2-substrate:	0.801
CYP2C19-inhibitor:	0.726
CYP2C19-substrate:	0.78
CYP2C9-inhibitor:	0.498
CYP2C9-substrate:	0.802
CYP2D6-inhibitor:	0.956
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.969
CYP3A4-substrate:	0.854

ADMET: Excretion

Clearance (CL):	11.555
Half-life (T1/2):	0.321

ADMET: Toxicity

hERG Blockers:	0.244
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.536
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.628
Skin Sensitization:	0.949
Carcinogencity:	0.91
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.695

Download Data

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

Natural Product: NPC46591

Natural Product ID:	NPC46591
*Common Name:**	(2S,3R,4R)-2-(5-Methoxy-3,4-Methylenedioxyphenyl)-4-(5-Methoxy-3,4-Methylenedioxybenzyl)-3-Furanmethanol
IUPAC Name:	[(2S,3R,4R)-2-(7-methoxy-1,3-benzodioxol-5-yl)-4-[(7-methoxy-1,3-benzodioxol-5-yl)methyl]oxolan-3-yl]methanol
Synonyms:
Standard InCHIKey:	NEKCZSOZRUNPLY-AUSJPIAWSA-N
Standard InCHI:	InChI=1S/C22H24O8/c1-24-16-4-12(5-18-21(16)29-10-27-18)3-14-9-26-20(15(14)8-23)13-6-17(25-2)22-19(7-13)28-11-30-22/h4-7,14-15,20,23H,3,8-11H2,1-2H3/t14-,15-,20+/m0/s1
SMILES:	COc1cc(C[C@H]2CO[C@H](c3cc(c4c(c3)OCO4)OC)[C@H]2CO)cc2c1OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL222581
PubChem CID:	16215161
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
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499322]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17358082]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17547458]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17040	Peperomia duclouxii	Species	Piperaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	74.3	ug.mL-1	PMID[507399]
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	99.1	ug.mL-1	PMID[507399]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	72.0	ug.mL-1	PMID[507399]

☑ 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 NPC46591 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	381
0.1-0.2	1327
0.2-0.3	3655
0.3-0.4	9573
0.4-0.5	9634
0.5-0.6	5229
0.6-0.7	8986
0.7-0.8	2859
0.8-0.85	655
0.85-0.9	321
0.9-0.95	68
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.985	High Similarity	NPC56091
0.9706	High Similarity	NPC477701
0.9706	High Similarity	NPC166884
0.9706	High Similarity	NPC141569
0.9699	High Similarity	NPC283949
0.9697	High Similarity	NPC25333
0.9697	High Similarity	NPC148893
0.9697	High Similarity	NPC150534
0.9697	High Similarity	NPC49235
0.9632	High Similarity	NPC12728
0.9632	High Similarity	NPC185071
0.9621	High Similarity	NPC31530
0.9559	High Similarity	NPC287124
0.9556	High Similarity	NPC226547
0.9552	High Similarity	NPC185908
0.9549	High Similarity	NPC189474
0.9489	High Similarity	NPC255566
0.9489	High Similarity	NPC298317
0.9481	High Similarity	NPC113550
0.9474	High Similarity	NPC47181
0.947	High Similarity	NPC72046
0.947	High Similarity	NPC65183
0.947	High Similarity	NPC261812
0.9412	High Similarity	NPC177868
0.9403	High Similarity	NPC18576
0.9403	High Similarity	NPC236522
0.9398	High Similarity	NPC136750
0.9398	High Similarity	NPC196937
0.9398	High Similarity	NPC266848
0.9343	High Similarity	NPC312199
0.9333	High Similarity	NPC121651
0.9286	High Similarity	NPC212890
0.9265	High Similarity	NPC469981
0.9265	High Similarity	NPC474039
0.9248	High Similarity	NPC227160
0.9248	High Similarity	NPC192255
0.9248	High Similarity	NPC82111
0.9214	High Similarity	NPC475868
0.9214	High Similarity	NPC477702
0.9209	High Similarity	NPC474808
0.9203	High Similarity	NPC471908
0.9197	High Similarity	NPC123526
0.9197	High Similarity	NPC193666
0.9197	High Similarity	NPC88640
0.9191	High Similarity	NPC11453
0.9179	High Similarity	NPC104077
0.9179	High Similarity	NPC259742
0.9179	High Similarity	NPC147616
0.9179	High Similarity	NPC219671
0.9173	High Similarity	NPC233224
0.9173	High Similarity	NPC271208
0.9167	High Similarity	NPC328682
0.9167	High Similarity	NPC281864
0.9167	High Similarity	NPC54321
0.9155	High Similarity	NPC248132
0.9155	High Similarity	NPC130449
0.9143	High Similarity	NPC239254
0.9143	High Similarity	NPC187774
0.9143	High Similarity	NPC472712
0.9143	High Similarity	NPC172171
0.9143	High Similarity	NPC118385
0.9143	High Similarity	NPC473046
0.9143	High Similarity	NPC472713
0.9137	High Similarity	NPC474295
0.9124	High Similarity	NPC101807
0.9118	High Similarity	NPC165155
0.9118	High Similarity	NPC34103
0.9118	High Similarity	NPC24490
0.9118	High Similarity	NPC141765
0.9111	High Similarity	NPC1474
0.9097	High Similarity	NPC164082
0.9091	High Similarity	NPC473092
0.9091	High Similarity	NPC95392
0.9091	High Similarity	NPC240521
0.9091	High Similarity	NPC473093
0.9091	High Similarity	NPC51328
0.9091	High Similarity	NPC8050
0.9091	High Similarity	NPC55715
0.9091	High Similarity	NPC35877
0.9091	High Similarity	NPC286235
0.9091	High Similarity	NPC55158
0.9078	High Similarity	NPC180953
0.9071	High Similarity	NPC324962
0.9058	High Similarity	NPC9068
0.9058	High Similarity	NPC156376
0.9051	High Similarity	NPC25695
0.9051	High Similarity	NPC172818
0.9044	High Similarity	NPC244983
0.9044	High Similarity	NPC326095
0.9037	High Similarity	NPC7744
0.9037	High Similarity	NPC129687
0.9037	High Similarity	NPC100223
0.9037	High Similarity	NPC171928
0.9037	High Similarity	NPC158526
0.9037	High Similarity	NPC33611
0.9037	High Similarity	NPC16830
0.903	High Similarity	NPC171550
0.903	High Similarity	NPC134764
0.9028	High Similarity	NPC473989
0.9023	High Similarity	NPC222127
0.9023	High Similarity	NPC226862
0.9023	High Similarity	NPC82862
0.9023	High Similarity	NPC165128
0.9023	High Similarity	NPC57119
0.9023	High Similarity	NPC158471
0.9007	High Similarity	NPC179521
0.9	High Similarity	NPC311057
0.9	High Similarity	NPC229172
0.9	High Similarity	NPC103637
0.9	High Similarity	NPC36531
0.9	High Similarity	NPC230538
0.9	High Similarity	NPC5262
0.9	High Similarity	NPC246947
0.9	High Similarity	NPC472714
0.8993	High Similarity	NPC103448
0.8993	High Similarity	NPC216434
0.8978	High Similarity	NPC99572
0.8978	High Similarity	NPC474139
0.8978	High Similarity	NPC142547
0.8978	High Similarity	NPC174191
0.8978	High Similarity	NPC126409
0.8978	High Similarity	NPC135777
0.8971	High Similarity	NPC58585
0.8958	High Similarity	NPC477698
0.8951	High Similarity	NPC39657
0.8944	High Similarity	NPC205316
0.8936	High Similarity	NPC477898
0.8936	High Similarity	NPC265154
0.8913	High Similarity	NPC143895
0.8913	High Similarity	NPC197166
0.8905	High Similarity	NPC287745
0.8904	High Similarity	NPC56184
0.8897	High Similarity	NPC238140
0.8897	High Similarity	NPC204215
0.8897	High Similarity	NPC175067
0.8889	High Similarity	NPC270751
0.8889	High Similarity	NPC316676
0.8889	High Similarity	NPC325720
0.8889	High Similarity	NPC71726
0.8889	High Similarity	NPC63574
0.8881	High Similarity	NPC154971
0.8881	High Similarity	NPC252286
0.8873	High Similarity	NPC84181
0.8873	High Similarity	NPC92693
0.8873	High Similarity	NPC218841
0.8872	High Similarity	NPC186845
0.8872	High Similarity	NPC285725
0.8872	High Similarity	NPC9891
0.8872	High Similarity	NPC206882
0.8872	High Similarity	NPC112571
0.8872	High Similarity	NPC40352
0.8872	High Similarity	NPC88297
0.8872	High Similarity	NPC213711
0.8872	High Similarity	NPC473960
0.8872	High Similarity	NPC50683
0.8865	High Similarity	NPC302506
0.8865	High Similarity	NPC472562
0.8865	High Similarity	NPC80326
0.8841	High Similarity	NPC101624
0.8841	High Similarity	NPC184938
0.8832	High Similarity	NPC112237
0.8832	High Similarity	NPC158331
0.8832	High Similarity	NPC69513
0.8832	High Similarity	NPC215833
0.8819	High Similarity	NPC116019
0.8811	High Similarity	NPC110763
0.8811	High Similarity	NPC189239
0.8811	High Similarity	NPC11422
0.8811	High Similarity	NPC178014
0.8811	High Similarity	NPC42716
0.8811	High Similarity	NPC279298
0.8811	High Similarity	NPC22150
0.8811	High Similarity	NPC38041
0.8811	High Similarity	NPC474749
0.8811	High Similarity	NPC469586
0.8811	High Similarity	NPC197352
0.8811	High Similarity	NPC166506
0.8806	High Similarity	NPC158737
0.8794	High Similarity	NPC300798
0.8794	High Similarity	NPC58137
0.8794	High Similarity	NPC472711
0.8786	High Similarity	NPC290714
0.8786	High Similarity	NPC201404
0.8786	High Similarity	NPC6369
0.8786	High Similarity	NPC53722
0.8786	High Similarity	NPC30951
0.8784	High Similarity	NPC136757
0.8784	High Similarity	NPC312763
0.8777	High Similarity	NPC32189
0.8768	High Similarity	NPC48863
0.8768	High Similarity	NPC107478
0.8768	High Similarity	NPC13745
0.8768	High Similarity	NPC251981
0.8767	High Similarity	NPC472709
0.8767	High Similarity	NPC472710
0.8759	High Similarity	NPC301961
0.8759	High Similarity	NPC166584
0.8759	High Similarity	NPC471505
0.8759	High Similarity	NPC106739
0.875	High Similarity	NPC226540

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 NPC46591 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	830
0.2-0.3	1869
0.3-0.4	2854
0.4-0.5	1726
0.5-0.6	1021
0.6-0.7	475
0.7-0.8	76
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD4967	Phase 2
0.8667	High Similarity	NPD4965	Approved
0.8667	High Similarity	NPD4966	Approved
0.854	High Similarity	NPD3027	Phase 3
0.8467	Intermediate Similarity	NPD37	Approved
0.8431	Intermediate Similarity	NPD6234	Discontinued
0.8358	Intermediate Similarity	NPD3705	Approved
0.8176	Intermediate Similarity	NPD7228	Approved
0.8089	Intermediate Similarity	NPD7199	Phase 2
0.7975	Intermediate Similarity	NPD7240	Approved
0.7972	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1613	Approved
0.7875	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1357	Approved
0.7842	Intermediate Similarity	NPD2983	Phase 2
0.7842	Intermediate Similarity	NPD2982	Phase 2
0.782	Intermediate Similarity	NPD5283	Phase 1
0.7785	Intermediate Similarity	NPD6674	Discontinued
0.777	Intermediate Similarity	NPD2981	Phase 2
0.7746	Intermediate Similarity	NPD3018	Phase 2
0.7746	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3818	Discontinued
0.7613	Intermediate Similarity	NPD1653	Approved
0.7569	Intermediate Similarity	NPD4908	Phase 1
0.7547	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7266	Discontinued
0.7466	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1091	Approved
0.7447	Intermediate Similarity	NPD1610	Phase 2
0.7425	Intermediate Similarity	NPD7074	Phase 3
0.7412	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5058	Phase 3
0.7379	Intermediate Similarity	NPD2861	Phase 2
0.7365	Intermediate Similarity	NPD7054	Approved
0.7365	Intermediate Similarity	NPD3620	Phase 2
0.7365	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4005	Discontinued
0.7333	Intermediate Similarity	NPD7680	Approved
0.7321	Intermediate Similarity	NPD7472	Approved
0.732	Intermediate Similarity	NPD4236	Phase 3
0.732	Intermediate Similarity	NPD4237	Approved
0.731	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1375	Discontinued
0.7303	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2977	Approved
0.7267	Intermediate Similarity	NPD2978	Approved
0.723	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4749	Approved
0.7205	Intermediate Similarity	NPD1934	Approved
0.7194	Intermediate Similarity	NPD7157	Approved
0.7193	Intermediate Similarity	NPD7808	Phase 3
0.719	Intermediate Similarity	NPD3540	Phase 1
0.7183	Intermediate Similarity	NPD5125	Phase 3
0.7183	Intermediate Similarity	NPD5126	Approved
0.7179	Intermediate Similarity	NPD7124	Phase 2
0.7178	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6797	Phase 2
0.7168	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1548	Phase 1
0.7161	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4110	Phase 3
0.7153	Intermediate Similarity	NPD228	Approved
0.7152	Intermediate Similarity	NPD5494	Approved
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7135	Intermediate Similarity	NPD7251	Discontinued
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3539	Phase 1
0.7117	Intermediate Similarity	NPD3817	Phase 2
0.7115	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6111	Discontinued
0.7101	Intermediate Similarity	NPD7843	Approved
0.7099	Intermediate Similarity	NPD3383	Approved
0.7099	Intermediate Similarity	NPD3382	Approved
0.7099	Intermediate Similarity	NPD3384	Approved
0.7097	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5735	Approved
0.7083	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6166	Phase 2
0.7083	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7028	Phase 2
0.7081	Intermediate Similarity	NPD4678	Approved
0.7081	Intermediate Similarity	NPD4675	Approved
0.7073	Intermediate Similarity	NPD3882	Suspended
0.7059	Intermediate Similarity	NPD5844	Phase 1
0.7059	Intermediate Similarity	NPD5588	Approved
0.7059	Intermediate Similarity	NPD4108	Discontinued
0.7059	Intermediate Similarity	NPD2684	Approved
0.7055	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6331	Phase 2
0.7051	Intermediate Similarity	NPD3892	Phase 2
0.7047	Intermediate Similarity	NPD4625	Phase 3
0.7035	Intermediate Similarity	NPD7685	Pre-registration
0.7025	Intermediate Similarity	NPD4357	Discontinued
0.702	Intermediate Similarity	NPD4060	Phase 1
0.702	Intermediate Similarity	NPD2238	Phase 2
0.7013	Intermediate Similarity	NPD2161	Phase 2
0.7007	Intermediate Similarity	NPD3021	Approved
0.7007	Intermediate Similarity	NPD3022	Approved
0.6993	Remote Similarity	NPD4536	Approved
0.6993	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4538	Approved
0.6989	Remote Similarity	NPD6842	Approved
0.6989	Remote Similarity	NPD6841	Approved
0.6989	Remote Similarity	NPD6843	Phase 3
0.6987	Remote Similarity	NPD5177	Phase 3
0.6987	Remote Similarity	NPD3060	Approved
0.6986	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6355	Discontinued
0.6974	Remote Similarity	NPD3657	Discovery
0.6972	Remote Similarity	NPD5536	Phase 2
0.6968	Remote Similarity	NPD5762	Approved
0.6968	Remote Similarity	NPD5763	Approved
0.6964	Remote Similarity	NPD6232	Discontinued
0.6962	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2801	Approved
0.6951	Remote Similarity	NPD8455	Phase 2
0.6941	Remote Similarity	NPD7473	Discontinued
0.6937	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4140	Approved
0.6905	Remote Similarity	NPD8127	Discontinued
0.6899	Remote Similarity	NPD2219	Phase 1
0.6893	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5109	Approved
0.6887	Remote Similarity	NPD5111	Phase 2
0.6887	Remote Similarity	NPD5110	Phase 2
0.6883	Remote Similarity	NPD7097	Phase 1
0.6879	Remote Similarity	NPD1652	Phase 2
0.6872	Remote Similarity	NPD7296	Approved
0.6871	Remote Similarity	NPD4380	Phase 2
0.6871	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3685	Discontinued
0.6864	Remote Similarity	NPD3787	Discontinued
0.6863	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5124	Phase 1
0.686	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4210	Discontinued
0.6842	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5960	Phase 3
0.6835	Remote Similarity	NPD4628	Phase 3
0.6832	Remote Similarity	NPD7526	Approved
0.6832	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD52	Approved
0.6832	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4055	Discovery
0.6824	Remote Similarity	NPD8651	Approved
0.6821	Remote Similarity	NPD7095	Approved
0.6818	Remote Similarity	NPD6653	Approved
0.6807	Remote Similarity	NPD2563	Approved
0.6807	Remote Similarity	NPD2560	Approved
0.6803	Remote Similarity	NPD1608	Approved
0.68	Remote Similarity	NPD7549	Discontinued
0.6797	Remote Similarity	NPD1558	Phase 1
0.6795	Remote Similarity	NPD2438	Suspended
0.6792	Remote Similarity	NPD2677	Approved
0.6792	Remote Similarity	NPD6190	Approved
0.6782	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4162	Approved
0.677	Remote Similarity	NPD4123	Phase 3
0.677	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7229	Phase 3
0.6763	Remote Similarity	NPD4750	Phase 3
0.6757	Remote Similarity	NPD5327	Phase 3
0.6755	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD230	Phase 1
0.6752	Remote Similarity	NPD6002	Phase 3
0.6752	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6004	Phase 3
0.6752	Remote Similarity	NPD6005	Phase 3
0.6752	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3687	Approved
0.6748	Remote Similarity	NPD3686	Approved
0.6747	Remote Similarity	NPD5772	Approved
0.6747	Remote Similarity	NPD5773	Approved
0.6747	Remote Similarity	NPD1465	Phase 2
0.6747	Remote Similarity	NPD7819	Suspended
0.6739	Remote Similarity	NPD290	Approved
0.6735	Remote Similarity	NPD422	Phase 1
0.6732	Remote Similarity	NPD6233	Phase 2
0.6731	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7466	Approved
0.6728	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5604	Discontinued
0.6725	Remote Similarity	NPD5242	Approved
0.6725	Remote Similarity	NPD3926	Phase 2
0.6712	Remote Similarity	NPD5846	Approved
0.6712	Remote Similarity	NPD6516	Phase 2
0.671	Remote Similarity	NPD6353	Approved
0.6709	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1511	Approved
0.6707	Remote Similarity	NPD7261	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