NPASS Compound

Structure

NPC177644 OpenBabel07101718292D 28 32 0 0 1 0 0 0 0 0999 V2000 -1.3975 5.5328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7248 2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4190 2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6369 3.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2851 5.0035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9328 3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6270 3.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8838 4.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1896 4.5546 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 3.0491 4.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0491 2.7298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4930 4.0254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2905 5.1081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 12 1 0 0 0 0 3 16 1 0 0 0 0 4 13 1 0 0 0 0 5 12 1 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 13 1 0 0 0 0 8 19 2 0 0 0 0 9 14 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 11 28 1 0 0 0 0 14 4 1 1 0 0 0 14 15 1 0 0 0 0 15 5 1 6 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 22 2 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.12
Volume:	372.066
LogP:	3.507
LogD:	3.46
LogS:	-5.36
# Rotatable Bonds:	5
TPSA:	72.45
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.734
Synthetic Accessibility Score:	3.394
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.937
MDCK Permeability:	3.3419812098145485e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.235
Plasma Protein Binding (PPB):	97.47069549560547%
Volume Distribution (VD):	1.449
Pgp-substrate:	2.7312657833099365%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.241
CYP2C19-inhibitor:	0.979
CYP2C19-substrate:	0.474
CYP2C9-inhibitor:	0.912
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.982
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.985
CYP3A4-substrate:	0.609

ADMET: Excretion

Clearance (CL):	15.601
Half-life (T1/2):	0.271

ADMET: Toxicity

hERG Blockers:	0.244
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.653
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.745
Skin Sensitization:	0.902
Carcinogencity:	0.892
Eye Corrosion:	0.004
Eye Irritation:	0.265
Respiratory Toxicity:	0.319

Download Data

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

Natural Product: NPC177644

Natural Product ID:	NPC177644
*Common Name:**	(2S,3S)-2-(3,4-Methylenedioxybenzyl)-3-(5-Methoxy-3,4-Methylenedioxybenzyl)Butyrolactone
IUPAC Name:	(3S,4S)-3-(1,3-benzodioxol-5-ylmethyl)-4-[(7-methoxy-1,3-benzodioxol-5-yl)methyl]oxolan-2-one
Synonyms:
Standard InCHIKey:	GBQHDHMFTXPYAM-CABCVRRESA-N
Standard InCHI:	InChI=1S/C21H20O7/c1-23-18-7-13(8-19-20(18)28-11-27-19)4-14-9-24-21(22)15(14)5-12-2-3-16-17(6-12)26-10-25-16/h2-3,6-8,14-15H,4-5,9-11H2,1H3/t14-,15+/m1/s1
SMILES:	COc1cc(C[C@@H]2COC(=O)[C@H]2Cc2ccc3c(c2)OCO3)cc2c1OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL493853
PubChem CID:	11516533
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
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
Others	6

Activity Type	# Activity
Cell Line	2
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	>	260000.0	nM	PMID[550670]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	260000.0	nM	PMID[550670]
NPT27	Others	Unspecified		IC50	>	260000.0	nM	PMID[550670]
NPT2	Others	Unspecified		Activity	=	91.0	%	PMID[550670]
NPT2	Others	Unspecified		Activity	=	102.0	%	PMID[550670]
NPT2	Others	Unspecified		Activity	=	74.0	%	PMID[550670]
NPT2	Others	Unspecified		Activity	=	70.0	%	PMID[550670]
NPT2	Others	Unspecified		Activity	=	96.0	%	PMID[550670]
NPT2	Others	Unspecified		Activity	=	67.0	%	PMID[550670]

☑ 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 NPC177644 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	362
0.1-0.2	1410
0.2-0.3	3151
0.3-0.4	8533
0.4-0.5	10711
0.5-0.6	4346
0.6-0.7	9837
0.7-0.8	3857
0.8-0.85	311
0.85-0.9	117
0.9-0.95	50
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC191158
0.9854	High Similarity	NPC218841
0.9854	High Similarity	NPC92693
0.9853	High Similarity	NPC176586
0.9853	High Similarity	NPC210354
0.9712	High Similarity	NPC193779
0.9708	High Similarity	NPC151423
0.9708	High Similarity	NPC40237
0.9568	High Similarity	NPC475000
0.9507	High Similarity	NPC177476
0.9507	High Similarity	NPC262455
0.9496	High Similarity	NPC474288
0.9412	High Similarity	NPC211386
0.9375	High Similarity	NPC164082
0.9371	High Similarity	NPC145569
0.9371	High Similarity	NPC216223
0.9366	High Similarity	NPC65574
0.9366	High Similarity	NPC304687
0.9366	High Similarity	NPC80230
0.9366	High Similarity	NPC101755
0.9366	High Similarity	NPC104024
0.9338	High Similarity	NPC110958
0.9338	High Similarity	NPC19890
0.927	High Similarity	NPC72796
0.927	High Similarity	NPC44245
0.9265	High Similarity	NPC205915
0.9236	High Similarity	NPC474965
0.9236	High Similarity	NPC174512
0.9236	High Similarity	NPC477695
0.9236	High Similarity	NPC293757
0.9236	High Similarity	NPC477698
0.9236	High Similarity	NPC668
0.9225	High Similarity	NPC474158
0.9203	High Similarity	NPC11453
0.9178	High Similarity	NPC56184
0.9172	High Similarity	NPC149505
0.9161	High Similarity	NPC3982
0.913	High Similarity	NPC189474
0.9118	High Similarity	NPC192255
0.911	High Similarity	NPC13985
0.911	High Similarity	NPC303519
0.911	High Similarity	NPC477700
0.911	High Similarity	NPC210642
0.9065	High Similarity	NPC102260
0.9065	High Similarity	NPC143895
0.9065	High Similarity	NPC230968
0.9058	High Similarity	NPC31530
0.9048	High Similarity	NPC477699
0.9034	High Similarity	NPC40654
0.9034	High Similarity	NPC262804
0.9021	High Similarity	NPC166884
0.9021	High Similarity	NPC141569
0.9021	High Similarity	NPC477701
0.9007	High Similarity	NPC96593
0.9007	High Similarity	NPC470637
0.9	High Similarity	NPC14022
0.8993	High Similarity	NPC49235
0.8993	High Similarity	NPC25333
0.8993	High Similarity	NPC148893
0.8986	High Similarity	NPC136750
0.8986	High Similarity	NPC266848
0.898	High Similarity	NPC474975
0.898	High Similarity	NPC32079
0.8951	High Similarity	NPC106920
0.8951	High Similarity	NPC273657
0.8947	High Similarity	NPC288149
0.8944	High Similarity	NPC246474
0.8944	High Similarity	NPC218092
0.8944	High Similarity	NPC162851
0.8929	High Similarity	NPC209229
0.8926	High Similarity	NPC136757
0.8926	High Similarity	NPC273578
0.8926	High Similarity	NPC178195
0.8926	High Similarity	NPC103197
0.8926	High Similarity	NPC30009
0.8926	High Similarity	NPC348849
0.8913	High Similarity	NPC72046
0.8913	High Similarity	NPC65183
0.8913	High Similarity	NPC261812
0.8881	High Similarity	NPC287124
0.8841	High Similarity	NPC227160
0.8841	High Similarity	NPC82111
0.8824	High Similarity	NPC223807
0.8819	High Similarity	NPC477697
0.8819	High Similarity	NPC470811
0.8819	High Similarity	NPC477696
0.8811	High Similarity	NPC312199
0.8811	High Similarity	NPC282291
0.8811	High Similarity	NPC166137
0.8808	High Similarity	NPC237946
0.8808	High Similarity	NPC473900
0.8808	High Similarity	NPC32373
0.8803	High Similarity	NPC113550
0.8768	High Similarity	NPC233224
0.8768	High Similarity	NPC271208
0.8759	High Similarity	NPC18211
0.875	High Similarity	NPC115281
0.875	High Similarity	NPC163527
0.875	High Similarity	NPC19947
0.875	High Similarity	NPC207584
0.875	High Similarity	NPC181168
0.8742	High Similarity	NPC234730
0.8742	High Similarity	NPC186316
0.8742	High Similarity	NPC254163
0.8741	High Similarity	NPC56091
0.8741	High Similarity	NPC46591
0.8732	High Similarity	NPC185908
0.8716	High Similarity	NPC125570
0.8699	High Similarity	NPC477702
0.8696	High Similarity	NPC476748
0.869	High Similarity	NPC255566
0.869	High Similarity	NPC298317
0.8662	High Similarity	NPC121651
0.8658	High Similarity	NPC475170
0.8643	High Similarity	NPC171928
0.8643	High Similarity	NPC100223
0.8643	High Similarity	NPC16830
0.8643	High Similarity	NPC158526
0.8643	High Similarity	NPC129687
0.8643	High Similarity	NPC7744
0.8643	High Similarity	NPC33611
0.8639	High Similarity	NPC87295
0.8639	High Similarity	NPC321958
0.8639	High Similarity	NPC321696
0.8639	High Similarity	NPC212890
0.8636	High Similarity	NPC268718
0.8636	High Similarity	NPC150943
0.8636	High Similarity	NPC91634
0.8636	High Similarity	NPC119910
0.863	High Similarity	NPC15743
0.863	High Similarity	NPC143092
0.863	High Similarity	NPC474036
0.8623	High Similarity	NPC165128
0.8623	High Similarity	NPC82862
0.8623	High Similarity	NPC158471
0.8623	High Similarity	NPC222127
0.8623	High Similarity	NPC57119
0.8623	High Similarity	NPC226862
0.8621	High Similarity	NPC474295
0.8621	High Similarity	NPC311057
0.8609	High Similarity	NPC473236
0.8609	High Similarity	NPC245948
0.8609	High Similarity	NPC308555
0.8601	High Similarity	NPC283949
0.86	High Similarity	NPC163002
0.8592	High Similarity	NPC150534
0.8592	High Similarity	NPC474139
0.8591	High Similarity	NPC85141
0.8582	High Similarity	NPC196937
0.8581	High Similarity	NPC258322
0.8581	High Similarity	NPC191352
0.8581	High Similarity	NPC152424
0.8581	High Similarity	NPC100465
0.8581	High Similarity	NPC239890
0.8581	High Similarity	NPC209411
0.8581	High Similarity	NPC115624
0.8571	High Similarity	NPC474043
0.8571	High Similarity	NPC318286
0.8571	High Similarity	NPC223185
0.8571	High Similarity	NPC327651
0.8562	High Similarity	NPC76415
0.8562	High Similarity	NPC185071
0.8562	High Similarity	NPC218510
0.8562	High Similarity	NPC12728
0.8551	High Similarity	NPC473092
0.8551	High Similarity	NPC158737
0.8551	High Similarity	NPC8050
0.8551	High Similarity	NPC473093
0.8543	High Similarity	NPC104353
0.8533	High Similarity	NPC158635
0.8533	High Similarity	NPC229882
0.8526	High Similarity	NPC61141
0.8526	High Similarity	NPC76687
0.8523	High Similarity	NPC304821
0.8521	High Similarity	NPC47181
0.8506	High Similarity	NPC19600
0.8503	High Similarity	NPC27159
0.8503	High Similarity	NPC326144
0.8493	Intermediate Similarity	NPC46180
0.8493	Intermediate Similarity	NPC253722
0.8493	Intermediate Similarity	NPC80326
0.8493	Intermediate Similarity	NPC52664
0.8493	Intermediate Similarity	NPC31751
0.8493	Intermediate Similarity	NPC253481
0.8493	Intermediate Similarity	NPC472562
0.8489	Intermediate Similarity	NPC328682
0.8489	Intermediate Similarity	NPC54321
0.8489	Intermediate Similarity	NPC281864
0.8487	Intermediate Similarity	NPC474514
0.8483	Intermediate Similarity	NPC103448
0.8483	Intermediate Similarity	NPC216434
0.8483	Intermediate Similarity	NPC177868
0.8483	Intermediate Similarity	NPC226547
0.8478	Intermediate Similarity	NPC285725
0.8478	Intermediate Similarity	NPC50683
0.8478	Intermediate Similarity	NPC112571
0.8472	Intermediate Similarity	NPC166184
0.8471	Intermediate Similarity	NPC14294
0.8471	Intermediate Similarity	NPC116759
0.8467	Intermediate Similarity	NPC472567

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 NPC177644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	850
0.2-0.3	1632
0.3-0.4	2740
0.4-0.5	1914
0.5-0.6	1134
0.6-0.7	495
0.7-0.8	82
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8808	High Similarity	NPD4965	Approved
0.8808	High Similarity	NPD4967	Phase 2
0.8808	High Similarity	NPD4966	Approved
0.8693	High Similarity	NPD6234	Discontinued
0.8609	High Similarity	NPD37	Approved
0.8523	High Similarity	NPD6980	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7199	Phase 2
0.8354	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7228	Approved
0.811	Intermediate Similarity	NPD7240	Approved
0.7986	Intermediate Similarity	NPD3705	Approved
0.7964	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD5283	Phase 1
0.7716	Intermediate Similarity	NPD5494	Approved
0.7671	Intermediate Similarity	NPD3027	Phase 3
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.7647	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4110	Phase 3
0.7589	Intermediate Similarity	NPD17	Approved
0.7578	Intermediate Similarity	NPD3817	Phase 2
0.7576	Intermediate Similarity	NPD5242	Approved
0.7556	Intermediate Similarity	NPD7680	Approved
0.7552	Intermediate Similarity	NPD2981	Phase 2
0.7531	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD2982	Phase 2
0.75	Intermediate Similarity	NPD2438	Suspended
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6355	Discontinued
0.7439	Intermediate Similarity	NPD919	Approved
0.7438	Intermediate Similarity	NPD7028	Phase 2
0.7431	Intermediate Similarity	NPD1608	Approved
0.743	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3018	Phase 2
0.741	Intermediate Similarity	NPD6232	Discontinued
0.74	Intermediate Similarity	NPD2979	Phase 3
0.7381	Intermediate Similarity	NPD7473	Discontinued
0.7376	Intermediate Similarity	NPD5536	Phase 2
0.7365	Intermediate Similarity	NPD3926	Phase 2
0.7362	Intermediate Similarity	NPD5353	Approved
0.7361	Intermediate Similarity	NPD1281	Approved
0.7353	Intermediate Similarity	NPD7074	Phase 3
0.7351	Intermediate Similarity	NPD1933	Approved
0.7346	Intermediate Similarity	NPD1934	Approved
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3748	Approved
0.7308	Intermediate Similarity	NPD5006	Approved
0.7308	Intermediate Similarity	NPD5005	Approved
0.7305	Intermediate Similarity	NPD7229	Phase 3
0.7301	Intermediate Similarity	NPD2801	Approved
0.7294	Intermediate Similarity	NPD7054	Approved
0.7294	Intermediate Similarity	NPD5844	Phase 1
0.7284	Intermediate Similarity	NPD6386	Approved
0.7284	Intermediate Similarity	NPD6385	Approved
0.7278	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD5585	Approved
0.7267	Intermediate Similarity	NPD7685	Pre-registration
0.7261	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7472	Approved
0.7237	Intermediate Similarity	NPD230	Phase 1
0.7222	Intermediate Similarity	NPD6599	Discontinued
0.7211	Intermediate Similarity	NPD1283	Approved
0.7205	Intermediate Similarity	NPD1653	Approved
0.7197	Intermediate Similarity	NPD4628	Phase 3
0.7195	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7819	Suspended
0.7188	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4420	Approved
0.7179	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1613	Approved
0.717	Intermediate Similarity	NPD4357	Discontinued
0.7168	Intermediate Similarity	NPD6559	Discontinued
0.7161	Intermediate Similarity	NPD2796	Approved
0.7161	Intermediate Similarity	NPD2531	Phase 2
0.7153	Intermediate Similarity	NPD1651	Approved
0.7153	Intermediate Similarity	NPD1357	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD1247	Approved
0.7133	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4908	Phase 1
0.7126	Intermediate Similarity	NPD7808	Phase 3
0.7125	Intermediate Similarity	NPD2532	Approved
0.7125	Intermediate Similarity	NPD2534	Approved
0.7125	Intermediate Similarity	NPD2533	Approved
0.7125	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3146	Approved
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7266	Discontinued
0.711	Intermediate Similarity	NPD6797	Phase 2
0.7107	Intermediate Similarity	NPD7124	Phase 2
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7105	Intermediate Similarity	NPD8032	Phase 2
0.7095	Intermediate Similarity	NPD7296	Approved
0.7091	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1465	Phase 2
0.7091	Intermediate Similarity	NPD8455	Phase 2
0.7089	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3750	Approved
0.7089	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7095	Approved
0.7073	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7251	Discontinued
0.7067	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4060	Phase 1
0.7047	Intermediate Similarity	NPD3266	Approved
0.7047	Intermediate Similarity	NPD2797	Approved
0.7047	Intermediate Similarity	NPD3267	Approved
0.7044	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6190	Approved
0.7041	Intermediate Similarity	NPD8127	Discontinued
0.7039	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1296	Phase 2
0.7037	Intermediate Similarity	NPD920	Approved
0.7027	Intermediate Similarity	NPD4359	Approved
0.7027	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5535	Approved
0.7018	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6166	Phase 2
0.7018	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1610	Phase 2
0.7006	Intermediate Similarity	NPD6002	Phase 3
0.7006	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6005	Phase 3
0.7006	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD3787	Discontinued
0.6993	Remote Similarity	NPD4062	Phase 3
0.6989	Remote Similarity	NPD7280	Phase 3
0.6989	Remote Similarity	NPD7281	Phase 3
0.697	Remote Similarity	NPD6873	Phase 2
0.6966	Remote Similarity	NPD1894	Discontinued
0.6964	Remote Similarity	NPD7075	Discontinued
0.6963	Remote Similarity	NPD7827	Phase 1
0.6962	Remote Similarity	NPD5958	Discontinued
0.6957	Remote Similarity	NPD1511	Approved
0.6951	Remote Similarity	NPD7458	Discontinued
0.6951	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5402	Approved
0.6943	Remote Similarity	NPD2935	Discontinued
0.6943	Remote Similarity	NPD6099	Approved
0.6943	Remote Similarity	NPD6100	Approved
0.6943	Remote Similarity	NPD3539	Phase 1
0.6939	Remote Similarity	NPD3847	Discontinued
0.6928	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD3384	Approved
0.6928	Remote Similarity	NPD3382	Approved
0.6928	Remote Similarity	NPD3268	Approved
0.6928	Remote Similarity	NPD6801	Discontinued
0.6928	Remote Similarity	NPD3383	Approved
0.6923	Remote Similarity	NPD7097	Phase 1
0.6923	Remote Similarity	NPD6111	Discontinued
0.6918	Remote Similarity	NPD5691	Approved
0.6918	Remote Similarity	NPD6674	Discontinued
0.6918	Remote Similarity	NPD1243	Approved
0.6914	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6832	Phase 2
0.6906	Remote Similarity	NPD1358	Approved
0.6905	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7768	Phase 2
0.6903	Remote Similarity	NPD447	Suspended
0.6899	Remote Similarity	NPD1375	Discontinued
0.6899	Remote Similarity	NPD3540	Phase 1
0.6894	Remote Similarity	NPD643	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4210	Discontinued
0.6889	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1510	Phase 2
0.6879	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD2799	Discontinued
0.6871	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1512	Approved
0.6867	Remote Similarity	NPD1876	Approved
0.6867	Remote Similarity	NPD7411	Suspended
0.6864	Remote Similarity	NPD6971	Discontinued
0.6864	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6653	Approved
0.6855	Remote Similarity	NPD4534	Discontinued
0.6839	Remote Similarity	NPD1240	Approved
0.6835	Remote Similarity	NPD3134	Approved
0.6835	Remote Similarity	NPD1551	Phase 2
0.6829	Remote Similarity	NPD5403	Approved
0.6818	Remote Similarity	NPD5110	Phase 2
0.6818	Remote Similarity	NPD5109	Approved
0.6818	Remote Similarity	NPD5111	Phase 2
0.6813	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5401	Approved
0.681	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4380	Phase 2
0.6802	Remote Similarity	NPD7315	Approved
0.68	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4618	Approved
0.6795	Remote Similarity	NPD4622	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