NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.1
Volume:	273.096
LogP:	3.153
LogD:	3.232
LogS:	-3.778
# Rotatable Bonds:	4
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.789
Synthetic Accessibility Score:	3.074
Fsp3:	0.4
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:	-4.585
MDCK Permeability:	5.59885629627388e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.88

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253
Plasma Protein Binding (PPB):	95.93910217285156%
Volume Distribution (VD):	0.819
Pgp-substrate:	3.9592339992523193%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.272
CYP2C19-inhibitor:	0.965
CYP2C19-substrate:	0.646
CYP2C9-inhibitor:	0.835
CYP2C9-substrate:	0.739
CYP2D6-inhibitor:	0.959
CYP2D6-substrate:	0.764
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.404

ADMET: Excretion

Clearance (CL):	13.101
Half-life (T1/2):	0.711

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.914
Drug-inuced Liver Injury (DILI):	0.119
AMES Toxicity:	0.19
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.956
Carcinogencity:	0.807
Eye Corrosion:	0.169
Eye Irritation:	0.667
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC85830

Natural Product ID:	NPC85830
*Common Name:**	Dihydromethysticin
IUPAC Name:	(2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
Synonyms:	(+)-Dihydromethysticin; Dihydromethysticin
Standard InCHIKey:	RSIWXFIBHXYNFM-NSHDSACASA-N
Standard InCHI:	InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3/t11-/m0/s1
SMILES:	COC1=CC(=O)O[C@H](C1)CCc1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL576066
PubChem CID:	88308
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001761] Kavalactones

*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
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11830162]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12809361]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	root	n.a.	n.a.	PMID[25597012]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26193	Piper methysticum	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	2
Others	19

Activity Type	# Activity
Individual Protein	2
Organism	17
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	24.84	%	PMID[559541]
NPT2	Others	Unspecified		IC50	=	20.0	ug.mL-1	PMID[559540]
NPT27	Others	Unspecified		IC50	=	313.0	ug.mL-1	PMID[559540]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	3.66	%	PMID[559541]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	GI	=	0.0	%	PMID[559542]
NPT2600	Organism	Fusarium solani	Fusarium solani	GI	=	48.4	%	PMID[559542]
NPT2600	Organism	Fusarium solani	Fusarium solani	GI	=	40.3	%	PMID[559542]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	GI	=	27.8	%	PMID[559542]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	GI	=	0.0	%	PMID[559542]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	48.2	%	PMID[559542]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	32.1	%	PMID[559542]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	55.6	%	PMID[559542]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	48.6	%	PMID[559542]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	56.7	%	PMID[559542]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	50.0	%	PMID[559542]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	74.8	%	PMID[559542]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	76.5	%	PMID[559542]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	89.9	%	PMID[559542]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	GI	=	31.9	%	PMID[559542]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	GI	=	18.8	%	PMID[559542]

☑ 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 NPC85830 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	296
0.1-0.2	1454
0.2-0.3	4263
0.3-0.4	10511
0.4-0.5	7948
0.5-0.6	5692
0.6-0.7	9676
0.7-0.8	2571
0.8-0.85	254
0.85-0.9	28
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9661	High Similarity	NPC193484
0.9174	High Similarity	NPC114845
0.9083	High Similarity	NPC69670
0.9076	High Similarity	NPC212643
0.9076	High Similarity	NPC199209
0.8898	High Similarity	NPC476748
0.877	High Similarity	NPC57501
0.874	High Similarity	NPC64948
0.8699	High Similarity	NPC344161
0.8689	High Similarity	NPC277460
0.8678	High Similarity	NPC111225
0.8647	High Similarity	NPC166184
0.8644	High Similarity	NPC31279
0.864	High Similarity	NPC256167
0.8626	High Similarity	NPC205915
0.8571	High Similarity	NPC143895
0.8571	High Similarity	NPC102260
0.8571	High Similarity	NPC230968
0.856	High Similarity	NPC301641
0.856	High Similarity	NPC80241
0.8559	High Similarity	NPC127326
0.8527	High Similarity	NPC158471
0.8527	High Similarity	NPC226862
0.8527	High Similarity	NPC57119
0.8527	High Similarity	NPC165128
0.8519	High Similarity	NPC278076
0.8507	High Similarity	NPC20796
0.8496	Intermediate Similarity	NPC73071
0.848	Intermediate Similarity	NPC267064
0.8473	Intermediate Similarity	NPC227160
0.8473	Intermediate Similarity	NPC82111
0.8468	Intermediate Similarity	NPC37858
0.845	Intermediate Similarity	NPC158737
0.845	Intermediate Similarity	NPC223807
0.8444	Intermediate Similarity	NPC178290
0.8444	Intermediate Similarity	NPC226005
0.8433	Intermediate Similarity	NPC11453
0.843	Intermediate Similarity	NPC303522
0.8425	Intermediate Similarity	NPC279379
0.8421	Intermediate Similarity	NPC19890
0.8421	Intermediate Similarity	NPC110958
0.8409	Intermediate Similarity	NPC7744
0.84	Intermediate Similarity	NPC2058
0.8397	Intermediate Similarity	NPC477694
0.8397	Intermediate Similarity	NPC477705
0.8397	Intermediate Similarity	NPC280399
0.8397	Intermediate Similarity	NPC233961
0.8397	Intermediate Similarity	NPC271208
0.8397	Intermediate Similarity	NPC233224
0.8397	Intermediate Similarity	NPC339621
0.8394	Intermediate Similarity	NPC104956
0.8372	Intermediate Similarity	NPC120225
0.8372	Intermediate Similarity	NPC213552
0.8361	Intermediate Similarity	NPC294941
0.8359	Intermediate Similarity	NPC60517
0.8359	Intermediate Similarity	NPC146886
0.8359	Intermediate Similarity	NPC20443
0.8358	Intermediate Similarity	NPC240915
0.8346	Intermediate Similarity	NPC266848
0.8346	Intermediate Similarity	NPC136750
0.8346	Intermediate Similarity	NPC288238
0.8333	Intermediate Similarity	NPC204466
0.8333	Intermediate Similarity	NPC477706
0.8333	Intermediate Similarity	NPC192255
0.8321	Intermediate Similarity	NPC51681
0.832	Intermediate Similarity	NPC119949
0.8296	Intermediate Similarity	NPC157554
0.8296	Intermediate Similarity	NPC37468
0.8295	Intermediate Similarity	NPC289459
0.8295	Intermediate Similarity	NPC17348
0.8284	Intermediate Similarity	NPC67247
0.8284	Intermediate Similarity	NPC7163
0.8281	Intermediate Similarity	NPC21238
0.8281	Intermediate Similarity	NPC249788
0.8281	Intermediate Similarity	NPC470887
0.8273	Intermediate Similarity	NPC15743
0.8273	Intermediate Similarity	NPC50696
0.8271	Intermediate Similarity	NPC16830
0.8271	Intermediate Similarity	NPC158526
0.8271	Intermediate Similarity	NPC100223
0.8271	Intermediate Similarity	NPC65183
0.8271	Intermediate Similarity	NPC72046
0.8271	Intermediate Similarity	NPC129687
0.8271	Intermediate Similarity	NPC33611
0.8271	Intermediate Similarity	NPC171928
0.8271	Intermediate Similarity	NPC261812
0.8268	Intermediate Similarity	NPC126935
0.8268	Intermediate Similarity	NPC57268
0.8268	Intermediate Similarity	NPC172676
0.8268	Intermediate Similarity	NPC70752
0.8268	Intermediate Similarity	NPC312713
0.8268	Intermediate Similarity	NPC216929
0.8268	Intermediate Similarity	NPC65933
0.8264	Intermediate Similarity	NPC245552
0.8261	Intermediate Similarity	NPC176586
0.8261	Intermediate Similarity	NPC287124
0.8261	Intermediate Similarity	NPC473873
0.8261	Intermediate Similarity	NPC140502
0.8261	Intermediate Similarity	NPC473792
0.8261	Intermediate Similarity	NPC210354
0.8258	Intermediate Similarity	NPC19242
0.8258	Intermediate Similarity	NPC275950
0.8254	Intermediate Similarity	NPC222175
0.8254	Intermediate Similarity	NPC202474
0.8244	Intermediate Similarity	NPC210674
0.824	Intermediate Similarity	NPC159916
0.824	Intermediate Similarity	NPC474214
0.824	Intermediate Similarity	NPC124916
0.8235	Intermediate Similarity	NPC14022
0.8231	Intermediate Similarity	NPC213711
0.8231	Intermediate Similarity	NPC40352
0.8231	Intermediate Similarity	NPC274356
0.8227	Intermediate Similarity	NPC153620
0.8227	Intermediate Similarity	NPC24257
0.8222	Intermediate Similarity	NPC174191
0.8222	Intermediate Similarity	NPC189474
0.8222	Intermediate Similarity	NPC184938
0.8222	Intermediate Similarity	NPC474139
0.8222	Intermediate Similarity	NPC101624
0.8217	Intermediate Similarity	NPC246704
0.8217	Intermediate Similarity	NPC18449
0.8217	Intermediate Similarity	NPC121783
0.8217	Intermediate Similarity	NPC34902
0.8214	Intermediate Similarity	NPC476450
0.8201	Intermediate Similarity	NPC218510
0.8201	Intermediate Similarity	NPC76415
0.8195	Intermediate Similarity	NPC476345
0.8189	Intermediate Similarity	NPC471877
0.8188	Intermediate Similarity	NPC282291
0.8188	Intermediate Similarity	NPC166137
0.8182	Intermediate Similarity	NPC270849
0.8182	Intermediate Similarity	NPC179309
0.8182	Intermediate Similarity	NPC26653
0.8182	Intermediate Similarity	NPC83062
0.8175	Intermediate Similarity	NPC100389
0.8175	Intermediate Similarity	NPC474320
0.8175	Intermediate Similarity	NPC318575
0.8169	Intermediate Similarity	NPC477375
0.8169	Intermediate Similarity	NPC198129
0.8169	Intermediate Similarity	NPC252281
0.8169	Intermediate Similarity	NPC327352
0.8168	Intermediate Similarity	NPC177167
0.8168	Intermediate Similarity	NPC286683
0.8162	Intermediate Similarity	NPC186418
0.8162	Intermediate Similarity	NPC471988
0.8162	Intermediate Similarity	NPC90431
0.816	Intermediate Similarity	NPC33271
0.8154	Intermediate Similarity	NPC27352
0.8148	Intermediate Similarity	NPC170779
0.8148	Intermediate Similarity	NPC31530
0.8148	Intermediate Similarity	NPC145769
0.8148	Intermediate Similarity	NPC135127
0.8148	Intermediate Similarity	NPC37065
0.8148	Intermediate Similarity	NPC470881
0.8148	Intermediate Similarity	NPC47181
0.8148	Intermediate Similarity	NPC90083
0.8143	Intermediate Similarity	NPC177644
0.8143	Intermediate Similarity	NPC475000
0.8143	Intermediate Similarity	NPC477701
0.8143	Intermediate Similarity	NPC110063
0.8143	Intermediate Similarity	NPC326144
0.8143	Intermediate Similarity	NPC166884
0.8143	Intermediate Similarity	NPC297342
0.8143	Intermediate Similarity	NPC141569
0.8143	Intermediate Similarity	NPC191158
0.8143	Intermediate Similarity	NPC474036
0.8136	Intermediate Similarity	NPC109637
0.8136	Intermediate Similarity	NPC292792
0.8134	Intermediate Similarity	NPC219671
0.8134	Intermediate Similarity	NPC106739
0.8134	Intermediate Similarity	NPC319969
0.8134	Intermediate Similarity	NPC104077
0.8134	Intermediate Similarity	NPC259742
0.8134	Intermediate Similarity	NPC137669
0.8134	Intermediate Similarity	NPC147616
0.8134	Intermediate Similarity	NPC471505
0.813	Intermediate Similarity	NPC165106
0.8129	Intermediate Similarity	NPC67467
0.8129	Intermediate Similarity	NPC151423
0.8129	Intermediate Similarity	NPC52664
0.8129	Intermediate Similarity	NPC40237
0.812	Intermediate Similarity	NPC173308
0.812	Intermediate Similarity	NPC181079
0.812	Intermediate Similarity	NPC307042
0.812	Intermediate Similarity	NPC134764
0.812	Intermediate Similarity	NPC63574
0.812	Intermediate Similarity	NPC476399
0.812	Intermediate Similarity	NPC472024
0.812	Intermediate Similarity	NPC80600
0.812	Intermediate Similarity	NPC79184
0.812	Intermediate Similarity	NPC171550
0.8116	Intermediate Similarity	NPC470855
0.8112	Intermediate Similarity	NPC85141
0.8112	Intermediate Similarity	NPC477374
0.8112	Intermediate Similarity	NPC477376
0.8112	Intermediate Similarity	NPC322426
0.8102	Intermediate Similarity	NPC281780
0.8099	Intermediate Similarity	NPC25496
0.8095	Intermediate Similarity	NPC70744
0.8095	Intermediate Similarity	NPC137537

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 NPC85830 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	898
0.2-0.3	1695
0.3-0.4	2722
0.4-0.5	1809
0.5-0.6	1099
0.6-0.7	586
0.7-0.8	74
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8413	Intermediate Similarity	NPD3705	Approved
0.832	Intermediate Similarity	NPD1357	Approved
0.8235	Intermediate Similarity	NPD1358	Approved
0.813	Intermediate Similarity	NPD5283	Phase 1
0.8085	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8016	Intermediate Similarity	NPD5536	Phase 2
0.7917	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD5691	Approved
0.7851	Intermediate Similarity	NPD3134	Approved
0.774	Intermediate Similarity	NPD1653	Approved
0.768	Intermediate Similarity	NPD228	Approved
0.766	Intermediate Similarity	NPD7266	Discontinued
0.7626	Intermediate Similarity	NPD2492	Phase 1
0.7622	Intermediate Similarity	NPD4110	Phase 3
0.7622	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5535	Approved
0.7594	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD4626	Approved
0.7533	Intermediate Similarity	NPD37	Approved
0.7518	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4966	Approved
0.7483	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2684	Approved
0.7429	Intermediate Similarity	NPD1933	Approved
0.741	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6234	Discontinued
0.74	Intermediate Similarity	NPD7028	Phase 2
0.7397	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD4060	Phase 1
0.7344	Intermediate Similarity	NPD7843	Approved
0.7343	Intermediate Similarity	NPD2438	Suspended
0.7339	Intermediate Similarity	NPD9697	Approved
0.7308	Intermediate Similarity	NPD7199	Phase 2
0.7308	Intermediate Similarity	NPD7157	Approved
0.7305	Intermediate Similarity	NPD6355	Discontinued
0.7292	Intermediate Similarity	NPD1375	Discontinued
0.7287	Intermediate Similarity	NPD1241	Discontinued
0.7266	Intermediate Similarity	NPD969	Suspended
0.7266	Intermediate Similarity	NPD7095	Approved
0.7259	Intermediate Similarity	NPD2981	Phase 2
0.7254	Intermediate Similarity	NPD2653	Approved
0.7234	Intermediate Similarity	NPD4140	Approved
0.7218	Intermediate Similarity	NPD5585	Approved
0.7215	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6798	Discontinued
0.7206	Intermediate Similarity	NPD2982	Phase 2
0.7206	Intermediate Similarity	NPD2983	Phase 2
0.7203	Intermediate Similarity	NPD7097	Phase 1
0.7194	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6674	Discontinued
0.7188	Intermediate Similarity	NPD3818	Discontinued
0.7185	Intermediate Similarity	NPD1281	Approved
0.7185	Intermediate Similarity	NPD1091	Approved
0.7185	Intermediate Similarity	NPD422	Phase 1
0.7183	Intermediate Similarity	NPD447	Suspended
0.7183	Intermediate Similarity	NPD3657	Discovery
0.7179	Intermediate Similarity	NPD919	Approved
0.7163	Intermediate Similarity	NPD6233	Phase 2
0.7133	Intermediate Similarity	NPD6653	Approved
0.7133	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3018	Phase 2
0.7122	Intermediate Similarity	NPD9494	Approved
0.7113	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3620	Phase 2
0.7113	Intermediate Similarity	NPD2979	Phase 3
0.7113	Intermediate Similarity	NPD1613	Approved
0.7111	Intermediate Similarity	NPD3847	Discontinued
0.7097	Intermediate Similarity	NPD3817	Phase 2
0.7095	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5109	Approved
0.7092	Intermediate Similarity	NPD5110	Phase 2
0.7092	Intermediate Similarity	NPD5111	Phase 2
0.709	Intermediate Similarity	NPD1651	Approved
0.7087	Intermediate Similarity	NPD290	Approved
0.7081	Intermediate Similarity	NPD7228	Approved
0.708	Intermediate Similarity	NPD5327	Phase 3
0.7078	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4236	Phase 3
0.7075	Intermediate Similarity	NPD4237	Approved
0.7075	Intermediate Similarity	NPD1652	Phase 2
0.7063	Intermediate Similarity	NPD4340	Discontinued
0.7059	Intermediate Similarity	NPD1611	Approved
0.7055	Intermediate Similarity	NPD5763	Approved
0.7055	Intermediate Similarity	NPD5762	Approved
0.7042	Intermediate Similarity	NPD4062	Phase 3
0.7039	Intermediate Similarity	NPD4210	Discontinued
0.7037	Intermediate Similarity	NPD17	Approved
0.7037	Intermediate Similarity	NPD1778	Approved
0.7034	Intermediate Similarity	NPD4108	Discontinued
0.7029	Intermediate Similarity	NPD1283	Approved
0.7027	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4628	Phase 3
0.7027	Intermediate Similarity	NPD6331	Phase 2
0.7013	Intermediate Similarity	NPD6385	Approved
0.7013	Intermediate Similarity	NPD6386	Approved
0.7012	Intermediate Similarity	NPD7685	Pre-registration
0.7007	Intermediate Similarity	NPD2424	Discontinued
0.7	Intermediate Similarity	NPD1139	Approved
0.7	Intermediate Similarity	NPD1137	Approved
0.6986	Remote Similarity	NPD6032	Approved
0.6986	Remote Similarity	NPD2935	Discontinued
0.6986	Remote Similarity	NPD2161	Phase 2
0.6981	Remote Similarity	NPD8127	Discontinued
0.6978	Remote Similarity	NPD2797	Approved
0.6978	Remote Similarity	NPD3266	Approved
0.6978	Remote Similarity	NPD3267	Approved
0.6977	Remote Similarity	NPD556	Approved
0.6977	Remote Similarity	NPD5451	Approved
0.696	Remote Similarity	NPD291	Approved
0.6957	Remote Similarity	NPD3685	Discontinued
0.6957	Remote Similarity	NPD4359	Approved
0.6954	Remote Similarity	NPD4739	Approved
0.6954	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3146	Approved
0.695	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6832	Phase 2
0.6947	Remote Similarity	NPD1138	Approved
0.6946	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5124	Phase 1
0.6944	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD776	Approved
0.6933	Remote Similarity	NPD7054	Approved
0.6933	Remote Similarity	NPD5058	Phase 3
0.6928	Remote Similarity	NPD3687	Approved
0.6928	Remote Similarity	NPD3686	Approved
0.6923	Remote Similarity	NPD2978	Approved
0.6923	Remote Similarity	NPD2977	Approved
0.6923	Remote Similarity	NPD8032	Phase 2
0.6918	Remote Similarity	NPD5494	Approved
0.6918	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7240	Approved
0.6906	Remote Similarity	NPD2922	Phase 1
0.6903	Remote Similarity	NPD6873	Phase 2
0.6892	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7074	Phase 3
0.689	Remote Similarity	NPD7472	Approved
0.6889	Remote Similarity	NPD1894	Discontinued
0.6889	Remote Similarity	NPD1182	Approved
0.6887	Remote Similarity	NPD5297	Approved
0.6884	Remote Similarity	NPD1608	Approved
0.6883	Remote Similarity	NPD7458	Discontinued
0.6883	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5353	Approved
0.6879	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2531	Phase 2
0.6867	Remote Similarity	NPD3887	Approved
0.6867	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1282	Approved
0.6859	Remote Similarity	NPD1934	Approved
0.6857	Remote Similarity	NPD987	Approved
0.6853	Remote Similarity	NPD5718	Phase 2
0.6853	Remote Similarity	NPD3268	Approved
0.6853	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1296	Phase 2
0.6849	Remote Similarity	NPD6895	Approved
0.6849	Remote Similarity	NPD6896	Approved
0.6846	Remote Similarity	NPD2067	Discontinued
0.6846	Remote Similarity	NPD4162	Approved
0.6846	Remote Similarity	NPD3021	Approved
0.6846	Remote Similarity	NPD3022	Approved
0.6835	Remote Similarity	NPD3882	Suspended
0.6835	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD230	Phase 1
0.6818	Remote Similarity	NPD821	Approved
0.6815	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2798	Approved
0.6806	Remote Similarity	NPD4870	Approved
0.6803	Remote Similarity	NPD7033	Discontinued
0.68	Remote Similarity	NPD8166	Discontinued
0.6797	Remote Similarity	NPD6273	Approved
0.6797	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6671	Approved
0.6791	Remote Similarity	NPD709	Approved
0.679	Remote Similarity	NPD5242	Approved
0.6788	Remote Similarity	NPD6516	Phase 2
0.6788	Remote Similarity	NPD5846	Approved
0.6786	Remote Similarity	NPD1876	Approved
0.6783	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5958	Discontinued
0.6779	Remote Similarity	NPD4534	Discontinued
0.6776	Remote Similarity	NPD4357	Discontinued
0.6774	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1247	Approved
0.6766	Remote Similarity	NPD7808	Phase 3
0.6763	Remote Similarity	NPD1840	Phase 2
0.6763	Remote Similarity	NPD3972	Approved
0.6761	Remote Similarity	NPD2861	Phase 2
0.6761	Remote Similarity	NPD2237	Approved
0.6759	Remote Similarity	NPD4307	Phase 2

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