NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	414.13
Volume:	404.072
LogP:	2.679
LogD:	3.02
LogS:	-4.739
# Rotatable Bonds:	6
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.57
Synthetic Accessibility Score:	3.682
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.762
MDCK Permeability:	3.0105597033980303e-05
Pgp-inhibitor:	0.285
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	93.553466796875%
Volume Distribution (VD):	0.76
Pgp-substrate:	7.019983768463135%

ADMET: Metabolism

CYP1A2-inhibitor:	0.178
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.84
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.882
CYP2C9-substrate:	0.86
CYP2D6-inhibitor:	0.863
CYP2D6-substrate:	0.79
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.875

ADMET: Excretion

Clearance (CL):	13.562
Half-life (T1/2):	0.296

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.545
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.758
Skin Sensitization:	0.4
Carcinogencity:	0.638
Eye Corrosion:	0.003
Eye Irritation:	0.417
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC477700

Natural Product ID:	NPC477700
*Common Name:**	(4S)-3-Methylene-4-[alpha-(4-methoxy-1,3-benzodioxole-6-yl)-4-hydroxy-3,5-dimethoxybenzyl]tetrahydrofuran-2-one
IUPAC Name:	(4S)-4-[(4-hydroxy-3,5-dimethoxyphenyl)-(7-methoxy-1,3-benzodioxol-5-yl)methyl]-3-methylideneoxolan-2-one
Synonyms:
Standard InCHIKey:	UGKOGWUDRSXQOZ-MJTSIZKDSA-N
Standard InCHI:	InChI=1S/C22H22O8/c1-11-14(9-28-22(11)24)19(12-5-15(25-2)20(23)16(6-12)26-3)13-7-17(27-4)21-18(8-13)29-10-30-21/h5-8,14,19,23H,1,9-10H2,2-4H3/t14-,19?/m1/s1
SMILES:	COC1=CC(=CC(=C1O)OC)C([C@@H]2COC(=O)C2=C)C3=CC4=C(C(=C3)OC)OCO4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11567816
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16309318]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16724842]
NPO27718	Peperomia dindygulensis	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	6
Others	6

Activity Type	# Activity
Cell Line	5
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	=	13500	nM	PMID[16724842]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	22300	nM	PMID[16724842]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4230	nM	PMID[16724842]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3160	nM	PMID[16724842]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	84700	nM	PMID[16724842]
NPT27	Others	Unspecified		IC50	=	20900	nM	PMID[16724842]
NPT2	Others	Unspecified		Activity	=	104	%	PMID[16724842]
NPT2	Others	Unspecified		Activity	=	98	%	PMID[16724842]
NPT2	Others	Unspecified		Activity	=	125	%	PMID[16724842]
NPT2	Others	Unspecified		Activity	=	85	%	PMID[16724842]
NPT2	Others	Unspecified		Activity	=	83	%	PMID[16724842]

☑ 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 NPC477700 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	325
0.1-0.2	1346
0.2-0.3	3181
0.3-0.4	7669
0.4-0.5	11046
0.5-0.6	4266
0.6-0.7	7487
0.7-0.8	6677
0.8-0.85	508
0.85-0.9	139
0.9-0.95	41
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC32079
0.986	High Similarity	NPC668
0.986	High Similarity	NPC474965
0.986	High Similarity	NPC174512
0.986	High Similarity	NPC293757
0.986	High Similarity	NPC477695
0.9722	High Similarity	NPC145569
0.9722	High Similarity	NPC216223
0.9658	High Similarity	NPC477699
0.9527	High Similarity	NPC136757
0.951	High Similarity	NPC475000
0.9441	High Similarity	NPC470811
0.9441	High Similarity	NPC477696
0.9441	High Similarity	NPC477697
0.9396	High Similarity	NPC103197
0.9396	High Similarity	NPC30009
0.9379	High Similarity	NPC193779
0.9371	High Similarity	NPC151423
0.9371	High Similarity	NPC40237
0.9346	High Similarity	NPC76687
0.9338	High Similarity	NPC163527
0.9338	High Similarity	NPC181168
0.9338	High Similarity	NPC115281
0.932	High Similarity	NPC477698
0.932	High Similarity	NPC125570
0.931	High Similarity	NPC477702
0.9306	High Similarity	NPC273657
0.9306	High Similarity	NPC106920
0.9262	High Similarity	NPC56184
0.9247	High Similarity	NPC212890
0.9241	High Similarity	NPC218841
0.9241	High Similarity	NPC92693
0.9236	High Similarity	NPC176586
0.9236	High Similarity	NPC210354
0.9216	High Similarity	NPC150943
0.9216	High Similarity	NPC91634
0.9216	High Similarity	NPC268718
0.9195	High Similarity	NPC164082
0.9167	High Similarity	NPC166137
0.9167	High Similarity	NPC282291
0.9133	High Similarity	NPC476434
0.911	High Similarity	NPC177644
0.911	High Similarity	NPC191158
0.9073	High Similarity	NPC473236
0.9048	High Similarity	NPC474158
0.9041	High Similarity	NPC474288
0.9038	High Similarity	NPC14294
0.9038	High Similarity	NPC116759
0.902	High Similarity	NPC32373
0.902	High Similarity	NPC237946
0.898	High Similarity	NPC27159
0.8973	High Similarity	NPC52664
0.8973	High Similarity	NPC287124
0.8966	High Similarity	NPC177868
0.8961	High Similarity	NPC207584
0.8961	High Similarity	NPC19947
0.8954	High Similarity	NPC238834
0.8951	High Similarity	NPC72796
0.8951	High Similarity	NPC44245
0.8938	High Similarity	NPC178737
0.8926	High Similarity	NPC304687
0.8926	High Similarity	NPC80230
0.8926	High Similarity	NPC101755
0.8926	High Similarity	NPC65574
0.8926	High Similarity	NPC104024
0.8919	High Similarity	NPC223185
0.8912	High Similarity	NPC185071
0.8912	High Similarity	NPC12728
0.8896	High Similarity	NPC478055
0.8889	High Similarity	NPC178195
0.8889	High Similarity	NPC11453
0.8889	High Similarity	NPC348849
0.8874	High Similarity	NPC149505
0.8868	High Similarity	NPC185498
0.8859	High Similarity	NPC472560
0.8859	High Similarity	NPC3982
0.8851	High Similarity	NPC477701
0.8851	High Similarity	NPC141569
0.8851	High Similarity	NPC166884
0.8846	High Similarity	NPC474770
0.8846	High Similarity	NPC119910
0.8844	High Similarity	NPC253481
0.8844	High Similarity	NPC31751
0.8844	High Similarity	NPC253722
0.8831	High Similarity	NPC476065
0.8824	High Similarity	NPC115466
0.8824	High Similarity	NPC245948
0.8824	High Similarity	NPC245615
0.8824	High Similarity	NPC178574
0.8824	High Similarity	NPC61604
0.8824	High Similarity	NPC299706
0.8824	High Similarity	NPC474606
0.8824	High Similarity	NPC65591
0.8819	High Similarity	NPC211386
0.8816	High Similarity	NPC13985
0.8816	High Similarity	NPC210642
0.8816	High Similarity	NPC303519
0.8816	High Similarity	NPC475756
0.8812	High Similarity	NPC117911
0.8808	High Similarity	NPC177476
0.8808	High Similarity	NPC262455
0.879	High Similarity	NPC100465
0.879	High Similarity	NPC115624
0.879	High Similarity	NPC288149
0.879	High Similarity	NPC152424
0.8784	High Similarity	NPC298317
0.8784	High Similarity	NPC255566
0.8782	High Similarity	NPC76211
0.8776	High Similarity	NPC100675
0.8766	High Similarity	NPC312763
0.8766	High Similarity	NPC198461
0.8759	High Similarity	NPC90431
0.8758	High Similarity	NPC471154
0.8758	High Similarity	NPC179240
0.875	High Similarity	NPC300776
0.875	High Similarity	NPC24425
0.875	High Similarity	NPC4982
0.875	High Similarity	NPC176814
0.875	High Similarity	NPC311912
0.875	High Similarity	NPC68779
0.875	High Similarity	NPC5310
0.8742	High Similarity	NPC475738
0.8742	High Similarity	NPC40654
0.8742	High Similarity	NPC262804
0.8742	High Similarity	NPC304821
0.8726	High Similarity	NPC96593
0.8718	High Similarity	NPC475592
0.8718	High Similarity	NPC472860
0.8718	High Similarity	NPC474990
0.871	High Similarity	NPC38699
0.8699	High Similarity	NPC474039
0.8699	High Similarity	NPC283949
0.8696	High Similarity	NPC88557
0.869	High Similarity	NPC34103
0.869	High Similarity	NPC150534
0.869	High Similarity	NPC141765
0.869	High Similarity	NPC165155
0.869	High Similarity	NPC24490
0.8688	High Similarity	NPC174734
0.8688	High Similarity	NPC474042
0.8681	High Similarity	NPC205915
0.8654	High Similarity	NPC163635
0.8649	High Similarity	NPC470991
0.8645	High Similarity	NPC287504
0.8645	High Similarity	NPC273578
0.8636	High Similarity	NPC95498
0.8636	High Similarity	NPC246566
0.8634	High Similarity	NPC79322
0.863	High Similarity	NPC143895
0.8627	High Similarity	NPC158635
0.8627	High Similarity	NPC229882
0.8627	High Similarity	NPC473989
0.8625	High Similarity	NPC222531
0.8618	High Similarity	NPC252402
0.8618	High Similarity	NPC130449
0.8618	High Similarity	NPC248132
0.8618	High Similarity	NPC102934
0.8608	High Similarity	NPC239966
0.8608	High Similarity	NPC203020
0.86	High Similarity	NPC118385
0.86	High Similarity	NPC187774
0.86	High Similarity	NPC472712
0.86	High Similarity	NPC472713
0.86	High Similarity	NPC473046
0.8599	High Similarity	NPC1913
0.859	High Similarity	NPC186316
0.8581	High Similarity	NPC24562
0.8581	High Similarity	NPC226547
0.8581	High Similarity	NPC217708
0.8581	High Similarity	NPC56091
0.8581	High Similarity	NPC77237
0.8581	High Similarity	NPC308739
0.8581	High Similarity	NPC46591
0.8581	High Similarity	NPC44730
0.8581	High Similarity	NPC126405
0.8581	High Similarity	NPC53669
0.8581	High Similarity	NPC297271
0.8581	High Similarity	NPC16791
0.8571	High Similarity	NPC306475
0.8571	High Similarity	NPC185908
0.8571	High Similarity	NPC281780
0.8562	High Similarity	NPC99572
0.8562	High Similarity	NPC85141
0.8562	High Similarity	NPC135777
0.8562	High Similarity	NPC126409
0.8562	High Similarity	NPC475865
0.8562	High Similarity	NPC469518
0.8562	High Similarity	NPC55158
0.8562	High Similarity	NPC469475
0.8562	High Similarity	NPC286235
0.8562	High Similarity	NPC142547
0.8562	High Similarity	NPC51328
0.8562	High Similarity	NPC113295
0.8553	High Similarity	NPC209411
0.8553	High Similarity	NPC239890
0.8545	High Similarity	NPC196771
0.8544	High Similarity	NPC472565
0.8544	High Similarity	NPC289811
0.8544	High Similarity	NPC215400
0.8544	High Similarity	NPC241600

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 NPC477700 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	823
0.2-0.3	1730
0.3-0.4	2677
0.4-0.5	1977
0.5-0.6	1088
0.6-0.7	481
0.7-0.8	87
0.8-0.85	8
0.85-0.9	1
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9276	High Similarity	NPD6234	Discontinued
0.902	High Similarity	NPD4966	Approved
0.902	High Similarity	NPD4967	Phase 2
0.902	High Similarity	NPD4965	Approved
0.8868	High Similarity	NPD7228	Approved
0.8824	High Similarity	NPD37	Approved
0.8553	High Similarity	NPD7199	Phase 2
0.8447	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7240	Approved
0.8293	Intermediate Similarity	NPD3818	Discontinued
0.8187	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD3882	Suspended
0.8027	Intermediate Similarity	NPD3027	Phase 3
0.7933	Intermediate Similarity	NPD230	Phase 1
0.7921	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7685	Pre-registration
0.787	Intermediate Similarity	NPD7074	Phase 3
0.7862	Intermediate Similarity	NPD1653	Approved
0.784	Intermediate Similarity	NPD1465	Phase 2
0.7836	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7054	Approved
0.7792	Intermediate Similarity	NPD7266	Discontinued
0.7778	Intermediate Similarity	NPD1934	Approved
0.7765	Intermediate Similarity	NPD7472	Approved
0.7747	Intermediate Similarity	NPD7680	Approved
0.773	Intermediate Similarity	NPD2801	Approved
0.7725	Intermediate Similarity	NPD6232	Discontinued
0.7707	Intermediate Similarity	NPD6190	Approved
0.7692	Intermediate Similarity	NPD7473	Discontinued
0.7683	Intermediate Similarity	NPD3817	Phase 2
0.7674	Intermediate Similarity	NPD6559	Discontinued
0.7622	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6797	Phase 2
0.7616	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3705	Approved
0.759	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7251	Discontinued
0.7533	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7532	Intermediate Similarity	NPD4110	Phase 3
0.7529	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6166	Phase 2
0.7529	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7808	Phase 3
0.7516	Intermediate Similarity	NPD1613	Approved
0.7516	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD5494	Approved
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7483	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6355	Discontinued
0.7453	Intermediate Similarity	NPD2533	Approved
0.7453	Intermediate Similarity	NPD2532	Approved
0.7453	Intermediate Similarity	NPD2534	Approved
0.7439	Intermediate Similarity	NPD7028	Phase 2
0.7421	Intermediate Similarity	NPD3750	Approved
0.7421	Intermediate Similarity	NPD7827	Phase 1
0.7421	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7819	Suspended
0.7391	Intermediate Similarity	NPD4357	Discontinued
0.7391	Intermediate Similarity	NPD6799	Approved
0.7391	Intermediate Similarity	NPD1511	Approved
0.7374	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5242	Approved
0.7333	Intermediate Similarity	NPD4380	Phase 2
0.7333	Intermediate Similarity	NPD6599	Discontinued
0.7315	Intermediate Similarity	NPD1608	Approved
0.7312	Intermediate Similarity	NPD8166	Discontinued
0.7305	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD9494	Approved
0.7301	Intermediate Similarity	NPD1512	Approved
0.729	Intermediate Similarity	NPD4060	Phase 1
0.7278	Intermediate Similarity	NPD2935	Discontinued
0.7273	Intermediate Similarity	NPD3764	Approved
0.7267	Intermediate Similarity	NPD2983	Phase 2
0.7267	Intermediate Similarity	NPD3926	Phase 2
0.7267	Intermediate Similarity	NPD2982	Phase 2
0.7262	Intermediate Similarity	NPD5353	Approved
0.7262	Intermediate Similarity	NPD5402	Approved
0.7255	Intermediate Similarity	NPD4908	Phase 1
0.7251	Intermediate Similarity	NPD8127	Discontinued
0.7246	Intermediate Similarity	NPD6801	Discontinued
0.7235	Intermediate Similarity	NPD919	Approved
0.7222	Intermediate Similarity	NPD5283	Phase 1
0.7219	Intermediate Similarity	NPD7768	Phase 2
0.7215	Intermediate Similarity	NPD1510	Phase 2
0.7209	Intermediate Similarity	NPD7229	Phase 3
0.7202	Intermediate Similarity	NPD8455	Phase 2
0.72	Intermediate Similarity	NPD2981	Phase 2
0.72	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9269	Phase 2
0.7198	Intermediate Similarity	NPD7296	Approved
0.719	Intermediate Similarity	NPD3018	Phase 2
0.7186	Intermediate Similarity	NPD7411	Suspended
0.7179	Intermediate Similarity	NPD943	Approved
0.7179	Intermediate Similarity	NPD1240	Approved
0.7171	Intermediate Similarity	NPD2797	Approved
0.717	Intermediate Similarity	NPD6099	Approved
0.717	Intermediate Similarity	NPD6100	Approved
0.717	Intermediate Similarity	NPD2438	Suspended
0.717	Intermediate Similarity	NPD1551	Phase 2
0.7169	Intermediate Similarity	NPD7458	Discontinued
0.7162	Intermediate Similarity	NPD1357	Approved
0.7161	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6798	Discontinued
0.7152	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7134	Intermediate Similarity	NPD447	Suspended
0.7134	Intermediate Similarity	NPD1933	Approved
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1610	Phase 2
0.7115	Intermediate Similarity	NPD6233	Phase 2
0.7114	Intermediate Similarity	NPD17	Approved
0.7107	Intermediate Similarity	NPD3748	Approved
0.7105	Intermediate Similarity	NPD1283	Approved
0.7104	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7095	Approved
0.7095	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD8313	Approved
0.7089	Intermediate Similarity	NPD1607	Approved
0.7083	Intermediate Similarity	NPD6386	Approved
0.7083	Intermediate Similarity	NPD228	Approved
0.7083	Intermediate Similarity	NPD6385	Approved
0.7083	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1549	Phase 2
0.7076	Intermediate Similarity	NPD3749	Approved
0.707	Intermediate Similarity	NPD3620	Phase 2
0.707	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3268	Approved
0.7045	Intermediate Similarity	NPD3751	Discontinued
0.7037	Intermediate Similarity	NPD6674	Discontinued
0.7037	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5005	Approved
0.7037	Intermediate Similarity	NPD5006	Approved
0.703	Intermediate Similarity	NPD5401	Approved
0.703	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD422	Phase 1
0.7019	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6004	Phase 3
0.7019	Intermediate Similarity	NPD6002	Phase 3
0.7019	Intermediate Similarity	NPD6005	Phase 3
0.7011	Intermediate Similarity	NPD3787	Discontinued
0.7006	Intermediate Similarity	NPD4062	Phase 3
0.7	Intermediate Similarity	NPD2799	Discontinued
0.6981	Remote Similarity	NPD6653	Approved
0.6977	Remote Similarity	NPD6971	Discontinued
0.6975	Remote Similarity	NPD5958	Discontinued
0.6964	Remote Similarity	NPD3455	Phase 2
0.6962	Remote Similarity	NPD2979	Phase 3
0.6957	Remote Similarity	NPD2796	Approved
0.6954	Remote Similarity	NPD1247	Approved
0.6944	Remote Similarity	NPD7549	Discontinued
0.6944	Remote Similarity	NPD3022	Approved
0.6944	Remote Similarity	NPD3021	Approved
0.6937	Remote Similarity	NPD7097	Phase 1
0.6933	Remote Similarity	NPD9268	Approved
0.6928	Remote Similarity	NPD4749	Approved
0.6928	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4420	Approved
0.6914	Remote Similarity	NPD5711	Approved
0.6914	Remote Similarity	NPD5710	Approved
0.6908	Remote Similarity	NPD1281	Approved
0.6907	Remote Similarity	NPD8151	Discontinued
0.6906	Remote Similarity	NPD7280	Phase 3
0.6906	Remote Similarity	NPD7281	Phase 3
0.6903	Remote Similarity	NPD5647	Approved
0.6901	Remote Similarity	NPD2978	Approved
0.6901	Remote Similarity	NPD2977	Approved
0.6894	Remote Similarity	NPD7033	Discontinued
0.6886	Remote Similarity	NPD6273	Approved
0.6885	Remote Similarity	NPD8434	Phase 2
0.6879	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4534	Discontinued
0.6867	Remote Similarity	NPD1894	Discontinued
0.6867	Remote Similarity	NPD1548	Phase 1
0.6867	Remote Similarity	NPD9545	Approved
0.6859	Remote Similarity	NPD2861	Phase 2
0.6857	Remote Similarity	NPD6959	Discontinued
0.6848	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD920	Approved
0.6842	Remote Similarity	NPD3847	Discontinued
0.6835	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5953	Discontinued
0.6832	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2800	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