NPASS Compound

Structure

CID301641 OpenBabel06191716112D 24 27 0 0 1 0 0 0 0 0999 V2000 4.2072 3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 4.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4781 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 3.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4752 3.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2072 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8904 0.3601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8904 1.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 5 2 0 0 0 0 3 15 1 0 0 0 0 4 6 2 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 13 1 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 16 2 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 11 23 1 0 0 0 0 12 22 1 0 0 0 0 12 24 1 0 0 0 0 13 1 1 1 0 0 0 13 14 1 0 0 0 0 14 2 1 1 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.15
Volume:	339.592
LogP:	5.276
LogD:	4.416
LogS:	-6.403
# Rotatable Bonds:	5
TPSA:	36.92
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.825
Synthetic Accessibility Score:	2.986
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.135
MDCK Permeability:	2.7526903068064712e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	99.18228149414062%
Volume Distribution (VD):	1.671
Pgp-substrate:	1.5833454132080078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.979
CYP2C19-substrate:	0.285
CYP2C9-inhibitor:	0.915
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.99
CYP2D6-substrate:	0.94
CYP3A4-inhibitor:	0.987
CYP3A4-substrate:	0.622

ADMET: Excretion

Clearance (CL):	18.991
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.186
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.525
Skin Sensitization:	0.787
Carcinogencity:	0.933
Eye Corrosion:	0.006
Eye Irritation:	0.269
Respiratory Toxicity:	0.236

Download Data

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

Natural Product: NPC301641

Natural Product ID:	NPC301641
*Common Name:**	Machilin A
IUPAC Name:	5-[(2R,3S)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-1,3-benzodioxole
Synonyms:
Standard InCHIKey:	QEFJURUMSHPMTC-OKILXGFUSA-N
Standard InCHI:	InChI=1S/C20H22O4/c1-13(7-15-3-5-17-19(9-15)23-11-21-17)14(2)8-16-4-6-18-20(10-16)24-12-22-18/h3-6,9-10,13-14H,7-8,11-12H2,1-2H3/t13-,14+
SMILES:	C[C@H]([C@@H](Cc1ccc2c(c1)OCO2)C)Cc1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL261367
PubChem CID:	10359012
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579855]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[11045899]
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18242997]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[19555186]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	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	4
Others	7

Activity Type	# Activity
Cell Line	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	MED	=	10.0	uM	PMID[503813]
NPT83	Cell Line	MCF7	Homo sapiens	Ratio	=	1.9	n.a.	PMID[503813]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.01	%	PMID[503813]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	13.5	%	PMID[503813]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	84.0	%	PMID[503814]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	89.0	%	PMID[503814]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	89900.0	nM	PMID[503814]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	98.0	%	PMID[503814]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	102700.0	nM	PMID[503814]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	175300.0	nM	PMID[503814]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	235500.0	nM	PMID[503814]

☑ 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 NPC301641 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	427
0.1-0.2	1703
0.2-0.3	4634
0.3-0.4	14054
0.4-0.5	4282
0.5-0.6	8730
0.6-0.7	6351
0.7-0.8	2139
0.8-0.85	276
0.85-0.9	73
0.9-0.95	23
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC80241
0.9825	High Similarity	NPC344161
0.95	High Similarity	NPC158737
0.95	High Similarity	NPC177167
0.9421	High Similarity	NPC226862
0.9421	High Similarity	NPC165128
0.9421	High Similarity	NPC158471
0.9421	High Similarity	NPC57119
0.9417	High Similarity	NPC213711
0.9417	High Similarity	NPC40352
0.9344	High Similarity	NPC476748
0.9333	High Similarity	NPC17348
0.9328	High Similarity	NPC249788
0.9268	High Similarity	NPC271208
0.9268	High Similarity	NPC233224
0.9256	High Similarity	NPC274356
0.9211	High Similarity	NPC165106
0.9194	High Similarity	NPC82111
0.9194	High Similarity	NPC227160
0.9194	High Similarity	NPC192255
0.912	High Similarity	NPC219671
0.912	High Similarity	NPC7744
0.912	High Similarity	NPC104077
0.912	High Similarity	NPC259742
0.912	High Similarity	NPC147616
0.9113	High Similarity	NPC134764
0.9113	High Similarity	NPC171550
0.9052	High Similarity	NPC47194
0.9052	High Similarity	NPC473264
0.9052	High Similarity	NPC475815
0.9048	High Similarity	NPC169973
0.9048	High Similarity	NPC136750
0.9048	High Similarity	NPC205915
0.9048	High Similarity	NPC266848
0.8976	High Similarity	NPC90083
0.8976	High Similarity	NPC170779
0.8974	High Similarity	NPC81067
0.8974	High Similarity	NPC9341
0.8968	High Similarity	NPC33611
0.8968	High Similarity	NPC65183
0.8968	High Similarity	NPC261812
0.8968	High Similarity	NPC129687
0.8968	High Similarity	NPC158526
0.8968	High Similarity	NPC171928
0.8968	High Similarity	NPC100223
0.8968	High Similarity	NPC16830
0.8968	High Similarity	NPC72046
0.896	High Similarity	NPC275950
0.8947	High Similarity	NPC31279
0.8934	High Similarity	NPC121783
0.8934	High Similarity	NPC34902
0.8934	High Similarity	NPC18449
0.8906	High Similarity	NPC135777
0.8906	High Similarity	NPC142547
0.8906	High Similarity	NPC474139
0.8906	High Similarity	NPC189474
0.8889	High Similarity	NPC476345
0.8871	High Similarity	NPC64948
0.8871	High Similarity	NPC100129
0.886	High Similarity	NPC127326
0.8843	High Similarity	NPC65933
0.8843	High Similarity	NPC312713
0.8843	High Similarity	NPC172676
0.8843	High Similarity	NPC126935
0.8843	High Similarity	NPC57268
0.8843	High Similarity	NPC216929
0.8828	High Similarity	NPC19890
0.8828	High Similarity	NPC47181
0.8828	High Similarity	NPC110958
0.8828	High Similarity	NPC31530
0.8824	High Similarity	NPC474040
0.8819	High Similarity	NPC106739
0.8819	High Similarity	NPC471505
0.8819	High Similarity	NPC227002
0.881	High Similarity	NPC181079
0.881	High Similarity	NPC173308
0.8769	High Similarity	NPC185908
0.876	High Similarity	NPC25333
0.876	High Similarity	NPC18576
0.876	High Similarity	NPC150534
0.876	High Similarity	NPC49235
0.876	High Similarity	NPC148893
0.875	High Similarity	NPC196937
0.8702	High Similarity	NPC123526
0.8702	High Similarity	NPC193666
0.8702	High Similarity	NPC88640
0.8699	High Similarity	NPC31344
0.8699	High Similarity	NPC317769
0.8692	High Similarity	NPC11453
0.8692	High Similarity	NPC32189
0.8692	High Similarity	NPC121651
0.8678	High Similarity	NPC232316
0.8678	High Similarity	NPC165133
0.8678	High Similarity	NPC56214
0.8678	High Similarity	NPC117780
0.8678	High Similarity	NPC227217
0.8678	High Similarity	NPC242885
0.8678	High Similarity	NPC95614
0.8672	High Similarity	NPC97316
0.8661	High Similarity	NPC63574
0.8651	High Similarity	NPC222127
0.8651	High Similarity	NPC82862
0.8626	High Similarity	NPC469981
0.8626	High Similarity	NPC101807
0.8626	High Similarity	NPC283949
0.8615	High Similarity	NPC101624
0.8615	High Similarity	NPC184938
0.8615	High Similarity	NPC174191
0.8595	High Similarity	NPC281298
0.8595	High Similarity	NPC310338
0.8595	High Similarity	NPC69670
0.8571	High Similarity	NPC473092
0.8571	High Similarity	NPC166137
0.8571	High Similarity	NPC8050
0.8571	High Similarity	NPC223807
0.8571	High Similarity	NPC282291
0.8571	High Similarity	NPC473093
0.8571	High Similarity	NPC312199
0.8561	High Similarity	NPC9068
0.8561	High Similarity	NPC113550
0.8561	High Similarity	NPC178290
0.8561	High Similarity	NPC156376
0.856	High Similarity	NPC85830
0.855	High Similarity	NPC143895
0.855	High Similarity	NPC102260
0.855	High Similarity	NPC230968
0.8548	High Similarity	NPC470887
0.8538	High Similarity	NPC185680
0.8538	High Similarity	NPC145722
0.8538	High Similarity	NPC256776
0.8537	High Similarity	NPC160380
0.8537	High Similarity	NPC477886
0.8537	High Similarity	NPC114845
0.8537	High Similarity	NPC38996
0.8516	High Similarity	NPC184814
0.8512	High Similarity	NPC470626
0.8512	High Similarity	NPC474214
0.8507	High Similarity	NPC210354
0.8507	High Similarity	NPC80326
0.8507	High Similarity	NPC472562
0.8507	High Similarity	NPC302506
0.8507	High Similarity	NPC176586
0.8507	High Similarity	NPC246947
0.8504	High Similarity	NPC281864
0.8504	High Similarity	NPC54321
0.8504	High Similarity	NPC328682
0.8496	Intermediate Similarity	NPC216434
0.8496	Intermediate Similarity	NPC46591
0.8496	Intermediate Similarity	NPC103448
0.8496	Intermediate Similarity	NPC177868
0.8496	Intermediate Similarity	NPC226547
0.8496	Intermediate Similarity	NPC56091
0.8492	Intermediate Similarity	NPC112571
0.8492	Intermediate Similarity	NPC206882
0.8492	Intermediate Similarity	NPC50683
0.8492	Intermediate Similarity	NPC285725
0.8485	Intermediate Similarity	NPC166184
0.8485	Intermediate Similarity	NPC196420
0.8468	Intermediate Similarity	NPC256167
0.8468	Intermediate Similarity	NPC85488
0.8462	Intermediate Similarity	NPC1474
0.845	Intermediate Similarity	NPC161557
0.845	Intermediate Similarity	NPC27843
0.845	Intermediate Similarity	NPC7171
0.845	Intermediate Similarity	NPC228346
0.845	Intermediate Similarity	NPC158079
0.845	Intermediate Similarity	NPC115207
0.845	Intermediate Similarity	NPC40432
0.8444	Intermediate Similarity	NPC298317
0.8444	Intermediate Similarity	NPC477898
0.8444	Intermediate Similarity	NPC265154
0.8444	Intermediate Similarity	NPC474288
0.8444	Intermediate Similarity	NPC255566
0.8444	Intermediate Similarity	NPC474808
0.8443	Intermediate Similarity	NPC474320
0.8443	Intermediate Similarity	NPC119949
0.8443	Intermediate Similarity	NPC475961
0.8443	Intermediate Similarity	NPC254625
0.8433	Intermediate Similarity	NPC471908
0.8433	Intermediate Similarity	NPC58137
0.8433	Intermediate Similarity	NPC218092
0.8433	Intermediate Similarity	NPC300798
0.8433	Intermediate Similarity	NPC246474
0.8433	Intermediate Similarity	NPC162851
0.843	Intermediate Similarity	NPC212643
0.843	Intermediate Similarity	NPC293619
0.843	Intermediate Similarity	NPC199209
0.8425	Intermediate Similarity	NPC98745
0.8421	Intermediate Similarity	NPC292792
0.8409	Intermediate Similarity	NPC197166
0.84	Intermediate Similarity	NPC280704
0.8385	Intermediate Similarity	NPC207400
0.8385	Intermediate Similarity	NPC181049
0.8382	Intermediate Similarity	NPC84181
0.8382	Intermediate Similarity	NPC177644
0.8382	Intermediate Similarity	NPC473575
0.8382	Intermediate Similarity	NPC191158
0.8382	Intermediate Similarity	NPC179521
0.837	Intermediate Similarity	NPC151423
0.837	Intermediate Similarity	NPC311057

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 NPC301641 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	1021
0.2-0.3	1387
0.3-0.4	2900
0.4-0.5	1815
0.5-0.6	1068
0.6-0.7	519
0.7-0.8	87
0.8-0.85	6
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9211	High Similarity	NPD5283	Phase 1
0.8689	High Similarity	NPD3705	Approved
0.8293	Intermediate Similarity	NPD1357	Approved
0.8175	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.813	Intermediate Similarity	NPD5536	Phase 2
0.7955	Intermediate Similarity	NPD5109	Approved
0.7955	Intermediate Similarity	NPD5111	Phase 2
0.7955	Intermediate Similarity	NPD5110	Phase 2
0.7934	Intermediate Similarity	NPD228	Approved
0.7929	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD3021	Approved
0.7769	Intermediate Similarity	NPD3022	Approved
0.7752	Intermediate Similarity	NPD2981	Phase 2
0.7744	Intermediate Similarity	NPD3027	Phase 3
0.7724	Intermediate Similarity	NPD7028	Phase 2
0.7692	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2982	Phase 2
0.7692	Intermediate Similarity	NPD2983	Phase 2
0.7664	Intermediate Similarity	NPD6896	Approved
0.7664	Intermediate Similarity	NPD6895	Approved
0.7647	Intermediate Similarity	NPD3657	Discovery
0.7639	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD5451	Approved
0.7606	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD3018	Phase 2
0.7584	Intermediate Similarity	NPD4965	Approved
0.7584	Intermediate Similarity	NPD4966	Approved
0.7584	Intermediate Similarity	NPD4967	Phase 2
0.7581	Intermediate Similarity	NPD5535	Approved
0.7574	Intermediate Similarity	NPD3620	Phase 2
0.7574	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD2684	Approved
0.754	Intermediate Similarity	NPD6387	Discontinued
0.754	Intermediate Similarity	NPD7157	Approved
0.7537	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2922	Phase 1
0.75	Intermediate Similarity	NPD1139	Approved
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD1137	Approved
0.7483	Intermediate Similarity	NPD6234	Discontinued
0.7482	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD4108	Discontinued
0.7465	Intermediate Similarity	NPD4110	Phase 3
0.7465	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD2492	Phase 1
0.745	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD4060	Phase 1
0.7442	Intermediate Similarity	NPD1651	Approved
0.744	Intermediate Similarity	NPD1138	Approved
0.744	Intermediate Similarity	NPD7843	Approved
0.7426	Intermediate Similarity	NPD5718	Phase 2
0.7424	Intermediate Similarity	NPD5327	Phase 3
0.7405	Intermediate Similarity	NPD1281	Approved
0.7402	Intermediate Similarity	NPD709	Approved
0.7394	Intermediate Similarity	NPD6674	Discontinued
0.7386	Intermediate Similarity	NPD7199	Phase 2
0.7376	Intermediate Similarity	NPD1375	Discontinued
0.7353	Intermediate Similarity	NPD7095	Approved
0.7343	Intermediate Similarity	NPD6331	Phase 2
0.7324	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1358	Approved
0.7311	Intermediate Similarity	NPD3020	Approved
0.7308	Intermediate Similarity	NPD5691	Approved
0.7308	Intermediate Similarity	NPD5585	Approved
0.7305	Intermediate Similarity	NPD2161	Phase 2
0.729	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6355	Discontinued
0.7259	Intermediate Similarity	NPD4624	Approved
0.7252	Intermediate Similarity	NPD2668	Approved
0.7252	Intermediate Similarity	NPD2667	Approved
0.7252	Intermediate Similarity	NPD4626	Approved
0.7246	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7124	Phase 2
0.7239	Intermediate Similarity	NPD1283	Approved
0.7236	Intermediate Similarity	NPD3134	Approved
0.7226	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2978	Approved
0.7219	Intermediate Similarity	NPD2977	Approved
0.7206	Intermediate Similarity	NPD2861	Phase 2
0.7203	Intermediate Similarity	NPD2808	Discontinued
0.7197	Intermediate Similarity	NPD3847	Discontinued
0.7194	Intermediate Similarity	NPD2979	Phase 3
0.7183	Intermediate Similarity	NPD2438	Suspended
0.7172	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD1669	Approved
0.7153	Intermediate Similarity	NPD4236	Phase 3
0.7153	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4237	Approved
0.7152	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD5735	Approved
0.7121	Intermediate Similarity	NPD5846	Approved
0.7121	Intermediate Similarity	NPD17	Approved
0.7121	Intermediate Similarity	NPD6516	Phase 2
0.7114	Intermediate Similarity	NPD4210	Discontinued
0.7111	Intermediate Similarity	NPD1876	Approved
0.7099	Intermediate Similarity	NPD1182	Approved
0.7092	Intermediate Similarity	NPD2653	Approved
0.709	Intermediate Similarity	NPD2232	Approved
0.709	Intermediate Similarity	NPD2233	Approved
0.709	Intermediate Similarity	NPD2230	Approved
0.709	Intermediate Similarity	NPD1840	Phase 2
0.708	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3596	Phase 2
0.7071	Intermediate Similarity	NPD1613	Approved
0.7071	Intermediate Similarity	NPD4140	Approved
0.7071	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3539	Phase 1
0.7059	Intermediate Similarity	NPD2860	Approved
0.7059	Intermediate Similarity	NPD2859	Approved
0.7042	Intermediate Similarity	NPD7119	Phase 2
0.7042	Intermediate Similarity	NPD6111	Discontinued
0.7039	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4359	Approved
0.7037	Intermediate Similarity	NPD3685	Discontinued
0.7034	Intermediate Similarity	NPD4162	Approved
0.7034	Intermediate Similarity	NPD3060	Approved
0.7029	Intermediate Similarity	NPD4908	Phase 1
0.7027	Intermediate Similarity	NPD4584	Approved
0.7021	Intermediate Similarity	NPD1933	Approved
0.7015	Intermediate Similarity	NPD1611	Approved
0.7014	Intermediate Similarity	NPD3540	Phase 1
0.7014	Intermediate Similarity	NPD7266	Discontinued
0.7007	Intermediate Similarity	NPD5058	Phase 3
0.7007	Intermediate Similarity	NPD6584	Phase 3
0.7007	Intermediate Similarity	NPD2798	Approved
0.7	Intermediate Similarity	NPD6671	Approved
0.7	Intermediate Similarity	NPD2674	Phase 3
0.7	Intermediate Similarity	NPD8032	Phase 2
0.6994	Remote Similarity	NPD7280	Phase 3
0.6994	Remote Similarity	NPD7281	Phase 3
0.6975	Remote Similarity	NPD7240	Approved
0.6975	Remote Similarity	NPD2934	Approved
0.6975	Remote Similarity	NPD2933	Approved
0.6974	Remote Similarity	NPD6873	Phase 2
0.6972	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6353	Approved
0.697	Remote Similarity	NPD6580	Approved
0.697	Remote Similarity	NPD6581	Approved
0.6966	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3972	Approved
0.6963	Remote Similarity	NPD1608	Approved
0.695	Remote Similarity	NPD1558	Phase 1
0.6944	Remote Similarity	NPD2531	Phase 2
0.6939	Remote Similarity	NPD5241	Discontinued
0.6929	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3144	Approved
0.6929	Remote Similarity	NPD6798	Discontinued
0.6929	Remote Similarity	NPD3145	Approved
0.6929	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7097	Phase 1
0.6918	Remote Similarity	NPD5177	Phase 3
0.6917	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3444	Approved
0.6917	Remote Similarity	NPD3445	Approved
0.6917	Remote Similarity	NPD3443	Approved
0.6913	Remote Similarity	NPD4739	Approved
0.6897	Remote Similarity	NPD5763	Approved
0.6897	Remote Similarity	NPD5762	Approved
0.6889	Remote Similarity	NPD1091	Approved
0.6889	Remote Similarity	NPD1610	Phase 2
0.6884	Remote Similarity	NPD7905	Discontinued
0.687	Remote Similarity	NPD2557	Approved
0.6867	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD8651	Approved
0.6859	Remote Similarity	NPD5604	Discontinued
0.6859	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2157	Approved
0.6853	Remote Similarity	NPD4097	Suspended
0.6848	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7458	Discontinued
0.6831	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3028	Approved
0.6825	Remote Similarity	NPD968	Approved
0.6821	Remote Similarity	NPD6031	Approved
0.6821	Remote Similarity	NPD5976	Discontinued
0.6821	Remote Similarity	NPD4727	Phase 1
0.6821	Remote Similarity	NPD6030	Approved
0.6821	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3383	Approved
0.6818	Remote Similarity	NPD3382	Approved
0.6818	Remote Similarity	NPD3384	Approved
0.6815	Remote Similarity	NPD3496	Discontinued
0.6797	Remote Similarity	NPD6876	Approved
0.6797	Remote Similarity	NPD6875	Approved
0.6788	Remote Similarity	NPD6582	Phase 2
0.6788	Remote Similarity	NPD6583	Phase 3
0.6776	Remote Similarity	NPD2883	Discontinued
0.6772	Remote Similarity	NPD290	Approved
0.6772	Remote Similarity	NPD5494	Approved
0.6769	Remote Similarity	NPD821	Approved
0.6765	Remote Similarity	NPD776	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