NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	416.15
Volume:	406.709
LogP:	2.921
LogD:	3.208
LogS:	-4.788
# 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:	0.719
Synthetic Accessibility Score:	3.795
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.757
MDCK Permeability:	3.7661342503270134e-05
Pgp-inhibitor:	0.573
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.081

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	95.80414581298828%
Volume Distribution (VD):	1.316
Pgp-substrate:	3.4360058307647705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.175
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.701
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.555
CYP2C9-substrate:	0.86
CYP2D6-inhibitor:	0.495
CYP2D6-substrate:	0.844
CYP3A4-inhibitor:	0.952
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	14.168
Half-life (T1/2):	0.213

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.512
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.163
Skin Sensitization:	0.237
Carcinogencity:	0.328
Eye Corrosion:	0.003
Eye Irritation:	0.278
Respiratory Toxicity:	0.754

Download Data

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

Natural Product: NPC477695

Natural Product ID:	NPC477695
*Common Name:**	(3S,4S)-3-Methyl-4-[alpha-(4-methoxy-1,3-benzodioxole-6-yl)-4-hydroxy-3,5-dimethoxybenzyl]tetrahydrofuran-2-one
IUPAC Name:	(3S,4S)-4-[(4-hydroxy-3,5-dimethoxyphenyl)-(7-methoxy-1,3-benzodioxol-5-yl)methyl]-3-methyloxolan-2-one
Synonyms:
Standard InCHIKey:	ZOMWNRBXFSZJFM-WHRCVXDFSA-N
Standard InCHI:	InChI=1S/C22H24O8/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/h5-8,11,14,19,23H,9-10H2,1-4H3/t11-,14+,19?/m0/s1
SMILES:	C[C@H]1[C@@H](COC1=O)C(C2=CC3=C(C(=C2)OC)OCO3)C4=CC(=C(C(=C4)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11517262
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	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	=	112000	nM	PMID[16724842]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	159000	nM	PMID[16724842]
NPT27	Others	Unspecified		IC50	=	174000	nM	PMID[16724842]
NPT2	Others	Unspecified		Activity	=	99	%	PMID[16724842]
NPT2	Others	Unspecified		Activity	=	104	%	PMID[16724842]
NPT2	Others	Unspecified		Activity	=	107	%	PMID[16724842]
NPT2	Others	Unspecified		Activity	=	93	%	PMID[16724842]
NPT2	Others	Unspecified		Activity	=	90	%	PMID[16724842]
NPT2	Others	Unspecified		Activity	=	71	%	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 NPC477695 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	322
0.1-0.2	1331
0.2-0.3	3197
0.3-0.4	7869
0.4-0.5	11022
0.5-0.6	4360
0.6-0.7	7836
0.7-0.8	6056
0.8-0.85	494
0.85-0.9	142
0.9-0.95	47
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC668
1.0	High Similarity	NPC174512
1.0	High Similarity	NPC474965
1.0	High Similarity	NPC293757
0.986	High Similarity	NPC477700
0.9859	High Similarity	NPC216223
0.9859	High Similarity	NPC145569
0.9792	High Similarity	NPC477699
0.9722	High Similarity	NPC32079
0.9658	High Similarity	NPC136757
0.9574	High Similarity	NPC477697
0.9574	High Similarity	NPC470811
0.9574	High Similarity	NPC477696
0.9524	High Similarity	NPC103197
0.9524	High Similarity	NPC30009
0.9504	High Similarity	NPC40237
0.9504	High Similarity	NPC151423
0.9463	High Similarity	NPC115281
0.9463	High Similarity	NPC163527
0.9463	High Similarity	NPC181168
0.9448	High Similarity	NPC125570
0.9448	High Similarity	NPC477698
0.9441	High Similarity	NPC477702
0.9437	High Similarity	NPC273657
0.9437	High Similarity	NPC106920
0.9388	High Similarity	NPC56184
0.9375	High Similarity	NPC212890
0.9371	High Similarity	NPC218841
0.9371	High Similarity	NPC475000
0.9371	High Similarity	NPC92693
0.9366	High Similarity	NPC176586
0.9366	High Similarity	NPC210354
0.9338	High Similarity	NPC150943
0.9338	High Similarity	NPC91634
0.9338	High Similarity	NPC268718
0.932	High Similarity	NPC164082
0.9296	High Similarity	NPC282291
0.9296	High Similarity	NPC166137
0.9241	High Similarity	NPC193779
0.9236	High Similarity	NPC177644
0.9236	High Similarity	NPC191158
0.9216	High Similarity	NPC76687
0.9195	High Similarity	NPC473236
0.9167	High Similarity	NPC474288
0.9156	High Similarity	NPC14294
0.9156	High Similarity	NPC116759
0.9139	High Similarity	NPC237946
0.9139	High Similarity	NPC32373
0.9103	High Similarity	NPC27159
0.9097	High Similarity	NPC52664
0.9097	High Similarity	NPC287124
0.9091	High Similarity	NPC177868
0.9079	High Similarity	NPC207584
0.9079	High Similarity	NPC19947
0.9078	High Similarity	NPC44245
0.9078	High Similarity	NPC72796
0.9073	High Similarity	NPC238834
0.9048	High Similarity	NPC80230
0.9048	High Similarity	NPC304687
0.9048	High Similarity	NPC101755
0.9048	High Similarity	NPC104024
0.9048	High Similarity	NPC65574
0.9041	High Similarity	NPC223185
0.9034	High Similarity	NPC185071
0.9034	High Similarity	NPC12728
0.9014	High Similarity	NPC11453
0.9013	High Similarity	NPC478055
0.9	High Similarity	NPC476434
0.8993	High Similarity	NPC149505
0.8981	High Similarity	NPC185498
0.898	High Similarity	NPC3982
0.8973	High Similarity	NPC477701
0.8973	High Similarity	NPC166884
0.8973	High Similarity	NPC141569
0.8966	High Similarity	NPC253481
0.8966	High Similarity	NPC253722
0.8966	High Similarity	NPC31751
0.8961	High Similarity	NPC119910
0.8944	High Similarity	NPC211386
0.894	High Similarity	NPC61604
0.894	High Similarity	NPC178574
0.894	High Similarity	NPC115466
0.894	High Similarity	NPC245948
0.894	High Similarity	NPC299706
0.894	High Similarity	NPC474606
0.894	High Similarity	NPC65591
0.894	High Similarity	NPC245615
0.8933	High Similarity	NPC210642
0.8933	High Similarity	NPC303519
0.8933	High Similarity	NPC13985
0.8933	High Similarity	NPC475756
0.8926	High Similarity	NPC262455
0.8926	High Similarity	NPC177476
0.8912	High Similarity	NPC474158
0.8904	High Similarity	NPC255566
0.8904	High Similarity	NPC298317
0.8903	High Similarity	NPC115624
0.8903	High Similarity	NPC152424
0.8903	High Similarity	NPC100465
0.8903	High Similarity	NPC288149
0.8897	High Similarity	NPC100675
0.8874	High Similarity	NPC471154
0.8873	High Similarity	NPC300776
0.8873	High Similarity	NPC5310
0.8873	High Similarity	NPC176814
0.8873	High Similarity	NPC4982
0.8873	High Similarity	NPC68779
0.8868	High Similarity	NPC179240
0.8867	High Similarity	NPC24425
0.8859	High Similarity	NPC304821
0.8851	High Similarity	NPC472560
0.8839	High Similarity	NPC96593
0.8824	High Similarity	NPC38699
0.8819	High Similarity	NPC283949
0.8819	High Similarity	NPC474039
0.8812	High Similarity	NPC178737
0.8811	High Similarity	NPC141765
0.8811	High Similarity	NPC165155
0.8811	High Similarity	NPC34103
0.8811	High Similarity	NPC150534
0.8811	High Similarity	NPC24490
0.8805	High Similarity	NPC117911
0.8803	High Similarity	NPC205915
0.8767	High Similarity	NPC470991
0.8766	High Similarity	NPC163635
0.8758	High Similarity	NPC273578
0.8758	High Similarity	NPC348849
0.8758	High Similarity	NPC178195
0.875	High Similarity	NPC143895
0.8742	High Similarity	NPC158635
0.8742	High Similarity	NPC473989
0.8742	High Similarity	NPC229882
0.8734	High Similarity	NPC222531
0.8733	High Similarity	NPC248132
0.8733	High Similarity	NPC130449
0.8733	High Similarity	NPC40654
0.8733	High Similarity	NPC262804
0.8718	High Similarity	NPC474770
0.8716	High Similarity	NPC472712
0.8716	High Similarity	NPC187774
0.8716	High Similarity	NPC473046
0.8716	High Similarity	NPC118385
0.8716	High Similarity	NPC472713
0.8701	High Similarity	NPC186316
0.8701	High Similarity	NPC476065
0.8699	High Similarity	NPC56091
0.8699	High Similarity	NPC226547
0.8699	High Similarity	NPC46591
0.869	High Similarity	NPC185908
0.869	High Similarity	NPC281780
0.8681	High Similarity	NPC142547
0.8681	High Similarity	NPC99572
0.8681	High Similarity	NPC113295
0.8681	High Similarity	NPC135777
0.8681	High Similarity	NPC126409
0.8679	High Similarity	NPC174734
0.8679	High Similarity	NPC306475
0.8679	High Similarity	NPC474042
0.8675	High Similarity	NPC55158
0.8675	High Similarity	NPC51328
0.8675	High Similarity	NPC286235
0.8662	High Similarity	NPC192255
0.8654	High Similarity	NPC76211
0.8636	High Similarity	NPC312763
0.8636	High Similarity	NPC198461
0.863	High Similarity	NPC30951
0.863	High Similarity	NPC6369
0.863	High Similarity	NPC123526
0.863	High Similarity	NPC88640
0.863	High Similarity	NPC193666
0.863	High Similarity	NPC9068
0.8625	High Similarity	NPC311912
0.8621	High Similarity	NPC209229
0.8621	High Similarity	NPC471988
0.8621	High Similarity	NPC90431
0.8616	High Similarity	NPC475738
0.8611	High Similarity	NPC19890
0.8611	High Similarity	NPC326095
0.8611	High Similarity	NPC110958
0.8611	High Similarity	NPC244983
0.8611	High Similarity	NPC67247
0.8609	High Similarity	NPC325720
0.8609	High Similarity	NPC316676
0.8601	High Similarity	NPC175067
0.8601	High Similarity	NPC261812
0.8601	High Similarity	NPC204215
0.8601	High Similarity	NPC72046
0.8601	High Similarity	NPC65183
0.86	High Similarity	NPC154971
0.86	High Similarity	NPC252286
0.8592	High Similarity	NPC63574
0.859	High Similarity	NPC472860
0.859	High Similarity	NPC475592
0.859	High Similarity	NPC474990
0.8581	High Similarity	NPC5262
0.8581	High Similarity	NPC472714
0.8571	High Similarity	NPC88557
0.8571	High Similarity	NPC203351
0.8571	High Similarity	NPC284464
0.8571	High Similarity	NPC147379

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 NPC477695 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	819
0.2-0.3	1727
0.3-0.4	2715
0.4-0.5	1952
0.5-0.6	1086
0.6-0.7	481
0.7-0.8	92
0.8-0.85	6
0.85-0.9	2
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.94	High Similarity	NPD6234	Discontinued
0.9139	High Similarity	NPD4966	Approved
0.9139	High Similarity	NPD4967	Phase 2
0.9139	High Similarity	NPD4965	Approved
0.8981	High Similarity	NPD7228	Approved
0.894	High Similarity	NPD37	Approved
0.8662	High Similarity	NPD7199	Phase 2
0.8553	High Similarity	NPD7184	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7240	Approved
0.8411	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3818	Discontinued
0.8138	Intermediate Similarity	NPD3027	Phase 3
0.8063	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3882	Suspended
0.7857	Intermediate Similarity	NPD7074	Phase 3
0.7833	Intermediate Similarity	NPD7680	Approved
0.7824	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD230	Phase 1
0.7798	Intermediate Similarity	NPD7054	Approved
0.7765	Intermediate Similarity	NPD7685	Pre-registration
0.7764	Intermediate Similarity	NPD1934	Approved
0.7751	Intermediate Similarity	NPD7472	Approved
0.7736	Intermediate Similarity	NPD1653	Approved
0.7718	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD2801	Approved
0.7716	Intermediate Similarity	NPD1465	Phase 2
0.7711	Intermediate Similarity	NPD6232	Discontinued
0.7708	Intermediate Similarity	NPD3705	Approved
0.7679	Intermediate Similarity	NPD7473	Discontinued
0.7669	Intermediate Similarity	NPD3817	Phase 2
0.7662	Intermediate Similarity	NPD7266	Discontinued
0.7635	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4110	Phase 3
0.7628	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1613	Approved
0.7616	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6797	Phase 2
0.7584	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6190	Approved
0.7566	Intermediate Similarity	NPD6355	Discontinued
0.7558	Intermediate Similarity	NPD7251	Discontinued
0.7558	Intermediate Similarity	NPD6559	Discontinued
0.7515	Intermediate Similarity	NPD6166	Phase 2
0.7515	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7827	Phase 1
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2534	Approved
0.7438	Intermediate Similarity	NPD2533	Approved
0.7438	Intermediate Similarity	NPD2532	Approved
0.7423	Intermediate Similarity	NPD7028	Phase 2
0.7415	Intermediate Similarity	NPD1608	Approved
0.7405	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4628	Phase 3
0.7386	Intermediate Similarity	NPD4060	Phase 1
0.7384	Intermediate Similarity	NPD5844	Phase 1
0.7381	Intermediate Similarity	NPD5494	Approved
0.7375	Intermediate Similarity	NPD1511	Approved
0.7365	Intermediate Similarity	NPD2983	Phase 2
0.7365	Intermediate Similarity	NPD2982	Phase 2
0.7365	Intermediate Similarity	NPD7075	Discontinued
0.7351	Intermediate Similarity	NPD4908	Phase 1
0.7324	Intermediate Similarity	NPD5283	Phase 1
0.7297	Intermediate Similarity	NPD2981	Phase 2
0.7296	Intermediate Similarity	NPD3750	Approved
0.7296	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7229	Phase 3
0.7289	Intermediate Similarity	NPD7819	Suspended
0.7289	Intermediate Similarity	NPD8455	Phase 2
0.7285	Intermediate Similarity	NPD3018	Phase 2
0.7284	Intermediate Similarity	NPD1512	Approved
0.7278	Intermediate Similarity	NPD7296	Approved
0.7267	Intermediate Similarity	NPD6799	Approved
0.7267	Intermediate Similarity	NPD4357	Discontinued
0.7263	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6099	Approved
0.7261	Intermediate Similarity	NPD2438	Suspended
0.7261	Intermediate Similarity	NPD6100	Approved
0.726	Intermediate Similarity	NPD1357	Approved
0.7255	Intermediate Similarity	NPD6798	Discontinued
0.7255	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5242	Approved
0.723	Intermediate Similarity	NPD1610	Phase 2
0.7222	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6599	Discontinued
0.7212	Intermediate Similarity	NPD4380	Phase 2
0.7211	Intermediate Similarity	NPD17	Approved
0.7208	Intermediate Similarity	NPD6233	Phase 2
0.72	Intermediate Similarity	NPD1283	Approved
0.719	Intermediate Similarity	NPD7095	Approved
0.7188	Intermediate Similarity	NPD8166	Discontinued
0.7186	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD228	Approved
0.7171	Intermediate Similarity	NPD9494	Approved
0.7169	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3620	Phase 2
0.7161	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2797	Approved
0.7152	Intermediate Similarity	NPD2935	Discontinued
0.7151	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD3764	Approved
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7126	Intermediate Similarity	NPD6801	Discontinued
0.7125	Intermediate Similarity	NPD6674	Discontinued
0.7118	Intermediate Similarity	NPD919	Approved
0.7107	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6004	Phase 3
0.7107	Intermediate Similarity	NPD6005	Phase 3
0.7107	Intermediate Similarity	NPD6002	Phase 3
0.7101	Intermediate Similarity	NPD7768	Phase 2
0.7097	Intermediate Similarity	NPD4062	Phase 3
0.7093	Intermediate Similarity	NPD3787	Discontinued
0.7089	Intermediate Similarity	NPD1510	Phase 2
0.707	Intermediate Similarity	NPD6653	Approved
0.7067	Intermediate Similarity	NPD9269	Phase 2
0.7066	Intermediate Similarity	NPD7411	Suspended
0.7063	Intermediate Similarity	NPD5958	Discontinued
0.7051	Intermediate Similarity	NPD1240	Approved
0.7051	Intermediate Similarity	NPD943	Approved
0.7051	Intermediate Similarity	NPD2979	Phase 3
0.7048	Intermediate Similarity	NPD7458	Discontinued
0.7044	Intermediate Similarity	NPD1551	Phase 2
0.7042	Intermediate Similarity	NPD3021	Approved
0.7042	Intermediate Similarity	NPD3022	Approved
0.7041	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3268	Approved
0.703	Intermediate Similarity	NPD5403	Approved
0.7025	Intermediate Similarity	NPD7097	Phase 1
0.7021	Intermediate Similarity	NPD5005	Approved
0.7021	Intermediate Similarity	NPD5006	Approved
0.702	Intermediate Similarity	NPD4749	Approved
0.7012	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5536	Phase 2
0.7006	Intermediate Similarity	NPD447	Suspended
0.7006	Intermediate Similarity	NPD1933	Approved
0.7	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD422	Phase 1
0.7	Intermediate Similarity	NPD1281	Approved
0.7	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5647	Approved
0.6983	Remote Similarity	NPD7280	Phase 3
0.6983	Remote Similarity	NPD8312	Approved
0.6983	Remote Similarity	NPD7281	Phase 3
0.6983	Remote Similarity	NPD8313	Approved
0.6982	Remote Similarity	NPD2978	Approved
0.6982	Remote Similarity	NPD2977	Approved
0.6981	Remote Similarity	NPD3748	Approved
0.6981	Remote Similarity	NPD7033	Discontinued
0.6964	Remote Similarity	NPD6386	Approved
0.6964	Remote Similarity	NPD6385	Approved
0.6962	Remote Similarity	NPD1607	Approved
0.6959	Remote Similarity	NPD1548	Phase 1
0.6959	Remote Similarity	NPD3749	Approved
0.6959	Remote Similarity	NPD1894	Discontinued
0.6959	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4534	Discontinued
0.6957	Remote Similarity	NPD1549	Phase 2
0.6948	Remote Similarity	NPD2861	Phase 2
0.6933	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3847	Discontinued
0.6932	Remote Similarity	NPD3751	Discontinued
0.6923	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5585	Approved
0.6909	Remote Similarity	NPD5401	Approved
0.6898	Remote Similarity	NPD4420	Approved
0.6897	Remote Similarity	NPD5711	Approved
0.6897	Remote Similarity	NPD5710	Approved
0.6894	Remote Similarity	NPD5763	Approved
0.6894	Remote Similarity	NPD5762	Approved
0.6887	Remote Similarity	NPD1091	Approved
0.6887	Remote Similarity	NPD1535	Discovery
0.6883	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6663	Approved
0.6879	Remote Similarity	NPD6746	Phase 2
0.6875	Remote Similarity	NPD2799	Discontinued
0.6867	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6971	Discontinued
0.6859	Remote Similarity	NPD4625	Phase 3
0.6845	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4005	Discontinued
0.6845	Remote Similarity	NPD3455	Phase 2
0.6845	Remote Similarity	NPD6723	Discontinued

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