NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.08
Volume:	197.524
LogP:	2.265
LogD:	2.587
LogS:	-2.927
# Rotatable Bonds:	2
TPSA:	27.69
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.72
Synthetic Accessibility Score:	2.333
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.599
MDCK Permeability:	1.7269278032472357e-05
Pgp-inhibitor:	0.362
Pgp-substrate:	0.932
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.486
Plasma Protein Binding (PPB):	94.24723815917969%
Volume Distribution (VD):	1.911
Pgp-substrate:	3.6459543704986572%

ADMET: Metabolism

CYP1A2-inhibitor:	0.995
CYP1A2-substrate:	0.88
CYP2C19-inhibitor:	0.862
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.184
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.913
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.81
CYP3A4-substrate:	0.37

ADMET: Excretion

Clearance (CL):	12.117
Half-life (T1/2):	0.605

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.068
Drug-inuced Liver Injury (DILI):	0.466
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.154
Skin Sensitization:	0.821
Carcinogencity:	0.898
Eye Corrosion:	0.727
Eye Irritation:	0.945
Respiratory Toxicity:	0.442

Download Data

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

Natural Product: NPC33271

Natural Product ID:	NPC33271
*Common Name:**	Isomyristicin
IUPAC Name:	4-methoxy-6-[(E)-prop-1-enyl]-1,3-benzodioxole
Synonyms:	Isomyristicin
Standard InCHIKey:	DHUZAAUGHUHIDS-ONEGZZNKSA-N
Standard InCHI:	InChI=1S/C11H12O3/c1-3-4-8-5-9(12-2)11-10(6-8)13-7-14-11/h3-6H,7H2,1-2H3/b4-3+
SMILES:	C/C=C/c1cc(c2c(c1)OCO2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1642213
PubChem CID:	6436484
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO9662	Conioselinum vaginatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4176	Mosla scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4176	Mosla scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9662	Conioselinum vaginatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9662	Conioselinum vaginatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4176	Mosla scabra	Species	Lamiaceae	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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2588	Organism	Paracentrotus lividus	Paracentrotus lividus	EC	>	5.0	uM	PMID[568993]

☑ 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 NPC33271 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	454
0.1-0.2	2344
0.2-0.3	8837
0.3-0.4	11063
0.4-0.5	3751
0.5-0.6	7241
0.6-0.7	6750
0.7-0.8	1938
0.8-0.85	262
0.85-0.9	45
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.982	High Similarity	NPC119949
0.9316	High Similarity	NPC191768
0.9316	High Similarity	NPC92869
0.9316	High Similarity	NPC283170
0.931	High Similarity	NPC211231
0.9273	High Similarity	NPC203924
0.9266	High Similarity	NPC165386
0.9266	High Similarity	NPC127326
0.9107	High Similarity	NPC204120
0.9009	High Similarity	NPC31279
0.9	High Similarity	NPC473960
0.8934	High Similarity	NPC228769
0.8934	High Similarity	NPC470633
0.887	High Similarity	NPC123948
0.8862	High Similarity	NPC63574
0.8793	High Similarity	NPC52464
0.8793	High Similarity	NPC259638
0.8793	High Similarity	NPC304208
0.879	High Similarity	NPC192255
0.8729	High Similarity	NPC222175
0.8707	High Similarity	NPC193067
0.8651	High Similarity	NPC136750
0.8651	High Similarity	NPC266848
0.8651	High Similarity	NPC471391
0.8651	High Similarity	NPC196937
0.8651	High Similarity	NPC58585
0.8651	High Similarity	NPC471390
0.8644	High Similarity	NPC308217
0.8644	High Similarity	NPC15805
0.8644	High Similarity	NPC20674
0.8644	High Similarity	NPC475961
0.8644	High Similarity	NPC254625
0.8632	High Similarity	NPC212643
0.8632	High Similarity	NPC199209
0.8624	High Similarity	NPC310905
0.8624	High Similarity	NPC12714
0.8583	High Similarity	NPC310373
0.8571	High Similarity	NPC72046
0.8571	High Similarity	NPC229401
0.8571	High Similarity	NPC65183
0.8571	High Similarity	NPC261812
0.856	High Similarity	NPC184814
0.8559	High Similarity	NPC63083
0.8547	High Similarity	NPC111225
0.8516	High Similarity	NPC189474
0.8512	High Similarity	NPC288238
0.85	High Similarity	NPC472596
0.85	High Similarity	NPC199023
0.85	High Similarity	NPC166759
0.8492	Intermediate Similarity	NPC473412
0.8492	Intermediate Similarity	NPC469698
0.8487	Intermediate Similarity	NPC69670
0.8468	Intermediate Similarity	NPC292792
0.845	Intermediate Similarity	NPC143895
0.845	Intermediate Similarity	NPC172818
0.845	Intermediate Similarity	NPC25695
0.8438	Intermediate Similarity	NPC256776
0.8438	Intermediate Similarity	NPC31530
0.8438	Intermediate Similarity	NPC145722
0.8438	Intermediate Similarity	NPC185680
0.843	Intermediate Similarity	NPC285289
0.843	Intermediate Similarity	NPC193484
0.843	Intermediate Similarity	NPC477886
0.8425	Intermediate Similarity	NPC162093
0.8421	Intermediate Similarity	NPC82016
0.8417	Intermediate Similarity	NPC61516
0.8417	Intermediate Similarity	NPC344161
0.8417	Intermediate Similarity	NPC474565
0.8417	Intermediate Similarity	NPC247364
0.8417	Intermediate Similarity	NPC232084
0.8417	Intermediate Similarity	NPC10932
0.8403	Intermediate Similarity	NPC474612
0.8387	Intermediate Similarity	NPC285725
0.8387	Intermediate Similarity	NPC112571
0.8387	Intermediate Similarity	NPC50683
0.8387	Intermediate Similarity	NPC52593
0.8385	Intermediate Similarity	NPC196420
0.8385	Intermediate Similarity	NPC195196
0.8385	Intermediate Similarity	NPC185908
0.8385	Intermediate Similarity	NPC20796
0.8372	Intermediate Similarity	NPC148893
0.8372	Intermediate Similarity	NPC38101
0.8372	Intermediate Similarity	NPC25333
0.8372	Intermediate Similarity	NPC73071
0.8372	Intermediate Similarity	NPC150534
0.8372	Intermediate Similarity	NPC49235
0.8372	Intermediate Similarity	NPC240915
0.8361	Intermediate Similarity	NPC194626
0.8361	Intermediate Similarity	NPC262253
0.8361	Intermediate Similarity	NPC261661
0.8361	Intermediate Similarity	NPC473411
0.8361	Intermediate Similarity	NPC71579
0.8361	Intermediate Similarity	NPC270326
0.8359	Intermediate Similarity	NPC49074
0.8359	Intermediate Similarity	NPC112237
0.8359	Intermediate Similarity	NPC1474
0.8359	Intermediate Similarity	NPC132895
0.8333	Intermediate Similarity	NPC226629
0.8333	Intermediate Similarity	NPC57501
0.8308	Intermediate Similarity	NPC11453
0.8308	Intermediate Similarity	NPC121651
0.8308	Intermediate Similarity	NPC197166
0.8308	Intermediate Similarity	NPC32189
0.8306	Intermediate Similarity	NPC58279
0.8306	Intermediate Similarity	NPC300326
0.8306	Intermediate Similarity	NPC27352
0.8295	Intermediate Similarity	NPC7163
0.8293	Intermediate Similarity	NPC282496
0.8293	Intermediate Similarity	NPC108545
0.8293	Intermediate Similarity	NPC233526
0.8293	Intermediate Similarity	NPC238810
0.8281	Intermediate Similarity	NPC299144
0.8281	Intermediate Similarity	NPC470270
0.8281	Intermediate Similarity	NPC7744
0.8279	Intermediate Similarity	NPC301641
0.8279	Intermediate Similarity	NPC80241
0.8279	Intermediate Similarity	NPC49341
0.8279	Intermediate Similarity	NPC114845
0.8258	Intermediate Similarity	NPC284464
0.8254	Intermediate Similarity	NPC222127
0.8254	Intermediate Similarity	NPC226862
0.8254	Intermediate Similarity	NPC165128
0.8254	Intermediate Similarity	NPC82862
0.8254	Intermediate Similarity	NPC57119
0.8254	Intermediate Similarity	NPC158471
0.8246	Intermediate Similarity	NPC227894
0.8246	Intermediate Similarity	NPC258171
0.8246	Intermediate Similarity	NPC35543
0.8244	Intermediate Similarity	NPC283949
0.8244	Intermediate Similarity	NPC474039
0.824	Intermediate Similarity	NPC127604
0.824	Intermediate Similarity	NPC88297
0.824	Intermediate Similarity	NPC9891
0.824	Intermediate Similarity	NPC186845
0.8231	Intermediate Similarity	NPC470236
0.8231	Intermediate Similarity	NPC236522
0.8226	Intermediate Similarity	NPC183446
0.8226	Intermediate Similarity	NPC5796
0.8226	Intermediate Similarity	NPC206487
0.8217	Intermediate Similarity	NPC215833
0.8217	Intermediate Similarity	NPC69513
0.8211	Intermediate Similarity	NPC264885
0.8211	Intermediate Similarity	NPC256167
0.8211	Intermediate Similarity	NPC41562
0.8205	Intermediate Similarity	NPC280606
0.8203	Intermediate Similarity	NPC227160
0.8203	Intermediate Similarity	NPC82111
0.8195	Intermediate Similarity	NPC312199
0.8195	Intermediate Similarity	NPC58137
0.8195	Intermediate Similarity	NPC300798
0.8182	Intermediate Similarity	NPC30951
0.8182	Intermediate Similarity	NPC6369
0.8182	Intermediate Similarity	NPC113550
0.8182	Intermediate Similarity	NPC53722
0.8182	Intermediate Similarity	NPC290714
0.8182	Intermediate Similarity	NPC9068
0.8182	Intermediate Similarity	NPC292487
0.8182	Intermediate Similarity	NPC201404
0.8175	Intermediate Similarity	NPC473093
0.8175	Intermediate Similarity	NPC473092
0.8175	Intermediate Similarity	NPC194841
0.8175	Intermediate Similarity	NPC8050
0.8174	Intermediate Similarity	NPC245115
0.8168	Intermediate Similarity	NPC164857
0.816	Intermediate Similarity	NPC475169
0.816	Intermediate Similarity	NPC265483
0.816	Intermediate Similarity	NPC299584
0.816	Intermediate Similarity	NPC82483
0.816	Intermediate Similarity	NPC203133
0.816	Intermediate Similarity	NPC251855
0.816	Intermediate Similarity	NPC472093
0.816	Intermediate Similarity	NPC233410
0.816	Intermediate Similarity	NPC234400
0.816	Intermediate Similarity	NPC105925
0.816	Intermediate Similarity	NPC208950
0.816	Intermediate Similarity	NPC193544
0.816	Intermediate Similarity	NPC298757
0.816	Intermediate Similarity	NPC60885
0.816	Intermediate Similarity	NPC116907
0.816	Intermediate Similarity	NPC117214
0.816	Intermediate Similarity	NPC173608
0.816	Intermediate Similarity	NPC221077
0.816	Intermediate Similarity	NPC57490
0.816	Intermediate Similarity	NPC271985
0.816	Intermediate Similarity	NPC17943
0.816	Intermediate Similarity	NPC85830
0.8158	Intermediate Similarity	NPC164576
0.8154	Intermediate Similarity	NPC107478
0.8154	Intermediate Similarity	NPC13745
0.8154	Intermediate Similarity	NPC251981
0.8154	Intermediate Similarity	NPC48863
0.8145	Intermediate Similarity	NPC165375
0.8145	Intermediate Similarity	NPC228922
0.8145	Intermediate Similarity	NPC197757
0.8145	Intermediate Similarity	NPC249788
0.8145	Intermediate Similarity	NPC220598
0.814	Intermediate Similarity	NPC252833
0.8134	Intermediate Similarity	NPC210354
0.8134	Intermediate Similarity	NPC176586
0.8134	Intermediate Similarity	NPC80326

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 NPC33271 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	1065
0.2-0.3	2283
0.3-0.4	2685
0.4-0.5	1432
0.5-0.6	898
0.6-0.7	349
0.7-0.8	37
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8583	High Similarity	NPD3705	Approved
0.8487	Intermediate Similarity	NPD1357	Approved
0.8361	Intermediate Similarity	NPD2981	Phase 2
0.8293	Intermediate Similarity	NPD2982	Phase 2
0.8293	Intermediate Similarity	NPD2983	Phase 2
0.8031	Intermediate Similarity	NPD3018	Phase 2
0.7966	Intermediate Similarity	NPD228	Approved
0.7907	Intermediate Similarity	NPD3027	Phase 3
0.7833	Intermediate Similarity	NPD5283	Phase 1
0.7786	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD5536	Phase 2
0.7557	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1613	Approved
0.7463	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD3539	Phase 1
0.7426	Intermediate Similarity	NPD6111	Discontinued
0.7397	Intermediate Similarity	NPD37	Approved
0.7391	Intermediate Similarity	NPD3540	Phase 1
0.7361	Intermediate Similarity	NPD1653	Approved
0.7353	Intermediate Similarity	NPD2492	Phase 1
0.7333	Intermediate Similarity	NPD1358	Approved
0.7324	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5297	Approved
0.7287	Intermediate Similarity	NPD1091	Approved
0.7266	Intermediate Similarity	NPD1375	Discontinued
0.7265	Intermediate Similarity	NPD1242	Phase 1
0.7248	Intermediate Similarity	NPD4966	Approved
0.7248	Intermediate Similarity	NPD4965	Approved
0.7248	Intermediate Similarity	NPD4967	Phase 2
0.7244	Intermediate Similarity	NPD1548	Phase 1
0.7203	Intermediate Similarity	NPD4357	Discontinued
0.7183	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7199	Phase 2
0.7154	Intermediate Similarity	NPD1610	Phase 2
0.7154	Intermediate Similarity	NPD422	Phase 1
0.7152	Intermediate Similarity	NPD6234	Discontinued
0.7133	Intermediate Similarity	NPD7124	Phase 2
0.7131	Intermediate Similarity	NPD2684	Approved
0.7107	Intermediate Similarity	NPD3134	Approved
0.7078	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2219	Phase 1
0.7049	Intermediate Similarity	NPD290	Approved
0.7034	Intermediate Similarity	NPD1424	Approved
0.7031	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD9296	Approved
0.6977	Remote Similarity	NPD7534	Approved
0.6977	Remote Similarity	NPD7533	Approved
0.6963	Remote Similarity	NPD9494	Approved
0.6959	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1558	Phase 1
0.6944	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD556	Approved
0.6923	Remote Similarity	NPD4237	Approved
0.6923	Remote Similarity	NPD4236	Phase 3
0.6917	Remote Similarity	NPD291	Approved
0.6917	Remote Similarity	NPD846	Approved
0.6917	Remote Similarity	NPD4749	Approved
0.6917	Remote Similarity	NPD940	Approved
0.6912	Remote Similarity	NPD4908	Phase 1
0.6912	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD230	Phase 1
0.6905	Remote Similarity	NPD7843	Approved
0.6897	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD776	Approved
0.6889	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7157	Approved
0.6875	Remote Similarity	NPD709	Approved
0.6871	Remote Similarity	NPD1350	Approved
0.6871	Remote Similarity	NPD1349	Approved
0.6871	Remote Similarity	NPD1351	Approved
0.6866	Remote Similarity	NPD2922	Phase 1
0.6863	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1182	Approved
0.6835	Remote Similarity	NPD7228	Approved
0.6835	Remote Similarity	NPD3818	Discontinued
0.6825	Remote Similarity	NPD1139	Approved
0.6825	Remote Similarity	NPD1137	Approved
0.6821	Remote Similarity	NPD3382	Approved
0.6821	Remote Similarity	NPD3383	Approved
0.6821	Remote Similarity	NPD3384	Approved
0.6818	Remote Similarity	NPD919	Approved
0.6812	Remote Similarity	NPD5718	Phase 2
0.6812	Remote Similarity	NPD3144	Approved
0.6812	Remote Similarity	NPD5110	Phase 2
0.6812	Remote Similarity	NPD3145	Approved
0.6812	Remote Similarity	NPD5109	Approved
0.6812	Remote Similarity	NPD5111	Phase 2
0.6812	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6674	Discontinued
0.68	Remote Similarity	NPD4678	Approved
0.68	Remote Similarity	NPD4675	Approved
0.68	Remote Similarity	NPD5451	Approved
0.6797	Remote Similarity	NPD3882	Suspended
0.6794	Remote Similarity	NPD5691	Approved
0.6788	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1933	Approved
0.6783	Remote Similarity	NPD7266	Discontinued
0.6776	Remote Similarity	NPD2978	Approved
0.6776	Remote Similarity	NPD2977	Approved
0.6772	Remote Similarity	NPD1138	Approved
0.6763	Remote Similarity	NPD2674	Phase 3
0.6742	Remote Similarity	NPD4626	Approved
0.6742	Remote Similarity	NPD1778	Approved
0.6742	Remote Similarity	NPD17	Approved
0.6739	Remote Similarity	NPD4625	Phase 3
0.6733	Remote Similarity	NPD4005	Discontinued
0.6732	Remote Similarity	NPD3817	Phase 2
0.6732	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3620	Phase 2
0.6714	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3454	Phase 3
0.6711	Remote Similarity	NPD1934	Approved
0.6691	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7028	Phase 2
0.6687	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD4210	Discontinued
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD7240	Approved
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD3657	Discovery
0.6646	Remote Similarity	NPD7074	Phase 3
0.6646	Remote Similarity	NPD7472	Approved
0.6645	Remote Similarity	NPD5089	Approved
0.6645	Remote Similarity	NPD5090	Approved
0.6645	Remote Similarity	NPD5604	Discontinued
0.6642	Remote Similarity	NPD1281	Approved
0.6641	Remote Similarity	NPD821	Approved
0.6641	Remote Similarity	NPD5535	Approved
0.6624	Remote Similarity	NPD1247	Approved
0.6623	Remote Similarity	NPD5353	Approved
0.6622	Remote Similarity	NPD1511	Approved
0.6621	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD970	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2653	Approved
0.6597	Remote Similarity	NPD2161	Phase 2
0.6596	Remote Similarity	NPD1240	Approved
0.6594	Remote Similarity	NPD2861	Phase 2
0.6593	Remote Similarity	NPD1608	Approved
0.6593	Remote Similarity	NPD1840	Phase 2
0.6589	Remote Similarity	NPD1241	Discontinued
0.6581	Remote Similarity	NPD9365	Approved
0.6581	Remote Similarity	NPD6788	Approved
0.6577	Remote Similarity	NPD4739	Approved
0.6577	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3146	Approved
0.6575	Remote Similarity	NPD1652	Phase 2
0.6575	Remote Similarity	NPD3060	Approved
0.6573	Remote Similarity	NPD6896	Approved
0.6573	Remote Similarity	NPD6895	Approved
0.6571	Remote Similarity	NPD1296	Phase 2
0.6561	Remote Similarity	NPD5677	Discontinued
0.656	Remote Similarity	NPD968	Approved
0.6558	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4585	Approved
0.6545	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD5327	Phase 3
0.6541	Remote Similarity	NPD3926	Phase 2
0.6541	Remote Similarity	NPD5585	Approved
0.6538	Remote Similarity	NPD4055	Discovery
0.6535	Remote Similarity	NPD4750	Phase 3
0.6535	Remote Similarity	NPD3021	Approved
0.6535	Remote Similarity	NPD3022	Approved
0.6533	Remote Similarity	NPD1512	Approved
0.6531	Remote Similarity	NPD4110	Phase 3
0.6531	Remote Similarity	NPD7466	Approved
0.6531	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4108	Discontinued
0.6528	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7808	Phase 3
0.6516	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1607	Approved
0.6503	Remote Similarity	NPD6797	Phase 2
0.6496	Remote Similarity	NPD1283	Approved
0.6496	Remote Similarity	NPD8651	Approved
0.6491	Remote Similarity	NPD111	Approved
0.6489	Remote Similarity	NPD6671	Approved
0.6483	Remote Similarity	NPD2796	Approved
0.648	Remote Similarity	NPD9697	Approved
0.6478	Remote Similarity	NPD6232	Discontinued
0.6467	Remote Similarity	NPD4123	Phase 3
0.6466	Remote Similarity	NPD9094	Approved
0.6463	Remote Similarity	NPD7251	Discontinued
0.6463	Remote Similarity	NPD1243	Approved
0.6452	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3686	Approved
0.6447	Remote Similarity	NPD3687	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