NPASS Compound

Structure

NPC344161 OpenBabel07101719142D 25 27 0 0 1 0 0 0 0 0999 V2000 4.4152 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 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 22 1 0 0 0 0 4 23 1 0 0 0 0 5 7 2 0 0 0 0 5 16 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 24 1 0 0 0 0 13 25 1 0 0 0 0 14 1 1 1 0 0 0 14 15 1 0 0 0 0 15 2 1 1 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.18
Volume:	365.445
LogP:	4.99
LogD:	4.396
LogS:	-5.646
# Rotatable Bonds:	7
TPSA:	36.92
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	2.831
Fsp3:	0.429
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:	-5.029
MDCK Permeability:	2.385828884143848e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.104
30% Bioavailability (F30%):	0.162

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	98.10114288330078%
Volume Distribution (VD):	2.25
Pgp-substrate:	1.4063585996627808%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.972
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.917
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.972
CYP2D6-substrate:	0.947
CYP3A4-inhibitor:	0.982
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	14.816
Half-life (T1/2):	0.378

ADMET: Toxicity

hERG Blockers:	0.287
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.892
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.25
Skin Sensitization:	0.834
Carcinogencity:	0.893
Eye Corrosion:	0.008
Eye Irritation:	0.116
Respiratory Toxicity:	0.055

Download Data

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

Natural Product: NPC344161

Natural Product ID:	NPC344161
*Common Name:**	5-[(2S,3R)-4-(3,4-Dimethoxyphenyl)-2,3-Dimethylbutyl]-1,3-Benzodioxole
IUPAC Name:	5-[(2S,3R)-4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,3-benzodioxole
Synonyms:
Standard InCHIKey:	ZANBLNRUVUOABN-CABCVRRESA-N
Standard InCHI:	InChI=1S/C21H26O4/c1-14(9-16-5-7-18(22-3)20(11-16)23-4)15(2)10-17-6-8-19-21(12-17)25-13-24-19/h5-8,11-12,14-15H,9-10,13H2,1-4H3/t14-,15+/m1/s1
SMILES:	COc1cc(ccc1OC)C[C@H]([C@H](Cc1ccc2c(c1)OCO2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3290508
PubChem CID:	14057534
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
NPO19979	Schisandra glaucescens	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[23373215]
NPO19979	Schisandra glaucescens	Species	Schisandraceae	Eukaryota	fruit	n.a.	n.a.	PMID[24927000]
NPO19979	Schisandra glaucescens	Species	Schisandraceae	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	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	58.1	%	PMID[568188]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	62.2	%	PMID[568188]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	61.1	%	PMID[568188]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	61.9	%	PMID[568188]

☑ 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 NPC344161 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	419
0.1-0.2	1663
0.2-0.3	4449
0.3-0.4	13864
0.4-0.5	4524
0.5-0.6	7952
0.6-0.7	7000
0.7-0.8	2368
0.8-0.85	330
0.85-0.9	102
0.9-0.95	21
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9825	High Similarity	NPC80241
0.9825	High Similarity	NPC301641
0.9492	High Similarity	NPC17348
0.9487	High Similarity	NPC249788
0.9412	High Similarity	NPC274356
0.9375	High Similarity	NPC165106
0.9333	High Similarity	NPC177167
0.9333	High Similarity	NPC158737
0.9256	High Similarity	NPC226862
0.9256	High Similarity	NPC158471
0.9256	High Similarity	NPC57119
0.9256	High Similarity	NPC165128
0.925	High Similarity	NPC40352
0.925	High Similarity	NPC213711
0.9211	High Similarity	NPC473264
0.9211	High Similarity	NPC47194
0.9211	High Similarity	NPC475815
0.918	High Similarity	NPC476748
0.913	High Similarity	NPC9341
0.913	High Similarity	NPC81067
0.9107	High Similarity	NPC31279
0.9106	High Similarity	NPC233224
0.9106	High Similarity	NPC271208
0.9106	High Similarity	NPC275950
0.9032	High Similarity	NPC227160
0.9032	High Similarity	NPC192255
0.9032	High Similarity	NPC82111
0.9032	High Similarity	NPC476345
0.9018	High Similarity	NPC127326
0.9016	High Similarity	NPC64948
0.9016	High Similarity	NPC100129
0.8992	High Similarity	NPC312713
0.8992	High Similarity	NPC57268
0.8992	High Similarity	NPC172676
0.8992	High Similarity	NPC65933
0.8992	High Similarity	NPC216929
0.8992	High Similarity	NPC126935
0.8974	High Similarity	NPC474040
0.896	High Similarity	NPC7744
0.896	High Similarity	NPC106739
0.896	High Similarity	NPC219671
0.896	High Similarity	NPC227002
0.896	High Similarity	NPC259742
0.896	High Similarity	NPC471505
0.896	High Similarity	NPC147616
0.896	High Similarity	NPC104077
0.8952	High Similarity	NPC173308
0.8952	High Similarity	NPC171550
0.8952	High Similarity	NPC134764
0.8952	High Similarity	NPC181079
0.8889	High Similarity	NPC136750
0.8889	High Similarity	NPC169973
0.8889	High Similarity	NPC196937
0.8889	High Similarity	NPC266848
0.8889	High Similarity	NPC205915
0.8843	High Similarity	NPC317769
0.8843	High Similarity	NPC31344
0.8824	High Similarity	NPC232316
0.8824	High Similarity	NPC227217
0.8824	High Similarity	NPC117780
0.8824	High Similarity	NPC165133
0.8824	High Similarity	NPC56214
0.8824	High Similarity	NPC242885
0.8824	High Similarity	NPC95614
0.8819	High Similarity	NPC90083
0.8819	High Similarity	NPC170779
0.881	High Similarity	NPC33611
0.881	High Similarity	NPC129687
0.881	High Similarity	NPC65183
0.881	High Similarity	NPC16830
0.881	High Similarity	NPC100223
0.881	High Similarity	NPC171928
0.881	High Similarity	NPC97316
0.881	High Similarity	NPC158526
0.881	High Similarity	NPC261812
0.881	High Similarity	NPC72046
0.88	High Similarity	NPC63574
0.877	High Similarity	NPC34902
0.877	High Similarity	NPC18449
0.877	High Similarity	NPC121783
0.875	High Similarity	NPC184938
0.875	High Similarity	NPC101624
0.875	High Similarity	NPC474139
0.875	High Similarity	NPC135777
0.875	High Similarity	NPC142547
0.875	High Similarity	NPC189474
0.8739	High Similarity	NPC281298
0.8739	High Similarity	NPC69670
0.8739	High Similarity	NPC310338
0.871	High Similarity	NPC223807
0.8699	High Similarity	NPC85830
0.8689	High Similarity	NPC470887
0.8682	High Similarity	NPC143895
0.8678	High Similarity	NPC38996
0.8678	High Similarity	NPC114845
0.8678	High Similarity	NPC160380
0.8678	High Similarity	NPC477886
0.8672	High Similarity	NPC185680
0.8672	High Similarity	NPC19890
0.8672	High Similarity	NPC110958
0.8672	High Similarity	NPC31530
0.8672	High Similarity	NPC47181
0.8672	High Similarity	NPC256776
0.8672	High Similarity	NPC145722
0.8655	High Similarity	NPC470626
0.8655	High Similarity	NPC474214
0.8651	High Similarity	NPC184814
0.8629	High Similarity	NPC285725
0.8629	High Similarity	NPC206882
0.8629	High Similarity	NPC112571
0.8629	High Similarity	NPC50683
0.8615	High Similarity	NPC185908
0.8615	High Similarity	NPC196420
0.8607	High Similarity	NPC85488
0.8607	High Similarity	NPC256167
0.8605	High Similarity	NPC49235
0.8605	High Similarity	NPC148893
0.8605	High Similarity	NPC18576
0.8605	High Similarity	NPC150534
0.8605	High Similarity	NPC25333
0.8594	High Similarity	NPC1474
0.8583	High Similarity	NPC254625
0.8583	High Similarity	NPC475961
0.8583	High Similarity	NPC119949
0.8583	High Similarity	NPC474320
0.8571	High Similarity	NPC212643
0.8571	High Similarity	NPC292792
0.8571	High Similarity	NPC293619
0.8571	High Similarity	NPC199209
0.856	High Similarity	NPC98745
0.855	High Similarity	NPC123526
0.855	High Similarity	NPC193666
0.855	High Similarity	NPC88640
0.8538	High Similarity	NPC11453
0.8538	High Similarity	NPC121651
0.8538	High Similarity	NPC197166
0.8538	High Similarity	NPC32189
0.8537	High Similarity	NPC280704
0.8492	Intermediate Similarity	NPC147247
0.8492	Intermediate Similarity	NPC129570
0.8492	Intermediate Similarity	NPC45774
0.8492	Intermediate Similarity	NPC222127
0.8492	Intermediate Similarity	NPC470084
0.8492	Intermediate Similarity	NPC82862
0.8492	Intermediate Similarity	NPC282703
0.8492	Intermediate Similarity	NPC184733
0.8492	Intermediate Similarity	NPC21867
0.8492	Intermediate Similarity	NPC246974
0.8492	Intermediate Similarity	NPC11258
0.8492	Intermediate Similarity	NPC128208
0.8485	Intermediate Similarity	NPC284464
0.848	Intermediate Similarity	NPC88297
0.848	Intermediate Similarity	NPC186845
0.848	Intermediate Similarity	NPC9891
0.8473	Intermediate Similarity	NPC469981
0.8473	Intermediate Similarity	NPC474039
0.8473	Intermediate Similarity	NPC101807
0.8473	Intermediate Similarity	NPC283949
0.8462	Intermediate Similarity	NPC236522
0.8462	Intermediate Similarity	NPC174191
0.8455	Intermediate Similarity	NPC30462
0.845	Intermediate Similarity	NPC112237
0.845	Intermediate Similarity	NPC471391
0.845	Intermediate Similarity	NPC471390
0.8443	Intermediate Similarity	NPC207613
0.843	Intermediate Similarity	NPC15805
0.8425	Intermediate Similarity	NPC470633
0.8425	Intermediate Similarity	NPC228769
0.8425	Intermediate Similarity	NPC475875
0.8421	Intermediate Similarity	NPC166137
0.8421	Intermediate Similarity	NPC312199
0.8421	Intermediate Similarity	NPC472711
0.8421	Intermediate Similarity	NPC28398
0.8421	Intermediate Similarity	NPC282291
0.8417	Intermediate Similarity	NPC33271
0.8413	Intermediate Similarity	NPC473092
0.8413	Intermediate Similarity	NPC99798
0.8413	Intermediate Similarity	NPC8050
0.8413	Intermediate Similarity	NPC157740
0.8413	Intermediate Similarity	NPC473093
0.8413	Intermediate Similarity	NPC191302
0.8409	Intermediate Similarity	NPC113550
0.8409	Intermediate Similarity	NPC9068
0.8409	Intermediate Similarity	NPC53722
0.8409	Intermediate Similarity	NPC30951
0.8409	Intermediate Similarity	NPC178290
0.8409	Intermediate Similarity	NPC6369
0.8409	Intermediate Similarity	NPC201404
0.8409	Intermediate Similarity	NPC156376
0.8409	Intermediate Similarity	NPC290714
0.84	Intermediate Similarity	NPC9067
0.84	Intermediate Similarity	NPC29008
0.84	Intermediate Similarity	NPC148627
0.84	Intermediate Similarity	NPC266705
0.84	Intermediate Similarity	NPC228771
0.8397	Intermediate Similarity	NPC230968
0.8397	Intermediate Similarity	NPC102260
0.8393	Intermediate Similarity	NPC12714
0.8393	Intermediate Similarity	NPC310905
0.8374	Intermediate Similarity	NPC324571

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 NPC344161 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	1000
0.2-0.3	1400
0.3-0.4	2842
0.4-0.5	1818
0.5-0.6	1064
0.6-0.7	550
0.7-0.8	123
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
0.9375	High Similarity	NPD5283	Phase 1
0.8833	High Similarity	NPD3705	Approved
0.843	Intermediate Similarity	NPD1357	Approved
0.8264	Intermediate Similarity	NPD5536	Phase 2
0.8077	Intermediate Similarity	NPD5110	Phase 2
0.8077	Intermediate Similarity	NPD5109	Approved
0.8077	Intermediate Similarity	NPD5111	Phase 2
0.8067	Intermediate Similarity	NPD228	Approved
0.8029	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD3021	Approved
0.7899	Intermediate Similarity	NPD3022	Approved
0.7874	Intermediate Similarity	NPD2981	Phase 2
0.7863	Intermediate Similarity	NPD3027	Phase 3
0.7812	Intermediate Similarity	NPD2983	Phase 2
0.7812	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2982	Phase 2
0.7778	Intermediate Similarity	NPD6895	Approved
0.7778	Intermediate Similarity	NPD6896	Approved
0.7761	Intermediate Similarity	NPD3657	Discovery
0.775	Intermediate Similarity	NPD5451	Approved
0.7746	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD3018	Phase 2
0.7708	Intermediate Similarity	NPD7028	Phase 2
0.7705	Intermediate Similarity	NPD5535	Approved
0.7687	Intermediate Similarity	NPD3620	Phase 2
0.7687	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2684	Approved
0.7661	Intermediate Similarity	NPD6387	Discontinued
0.7661	Intermediate Similarity	NPD7157	Approved
0.7652	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD1139	Approved
0.7623	Intermediate Similarity	NPD1137	Approved
0.7615	Intermediate Similarity	NPD2922	Phase 1
0.7603	Intermediate Similarity	NPD37	Approved
0.7591	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD4108	Discontinued
0.7591	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD2492	Phase 1
0.7571	Intermediate Similarity	NPD4110	Phase 3
0.7571	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7843	Approved
0.7561	Intermediate Similarity	NPD1138	Approved
0.7559	Intermediate Similarity	NPD1651	Approved
0.7556	Intermediate Similarity	NPD4060	Phase 1
0.7551	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD5327	Phase 3
0.7537	Intermediate Similarity	NPD5718	Phase 2
0.752	Intermediate Similarity	NPD709	Approved
0.7519	Intermediate Similarity	NPD1281	Approved
0.75	Intermediate Similarity	NPD6674	Discontinued
0.7482	Intermediate Similarity	NPD1375	Discontinued
0.7463	Intermediate Similarity	NPD7095	Approved
0.745	Intermediate Similarity	NPD4965	Approved
0.745	Intermediate Similarity	NPD4966	Approved
0.745	Intermediate Similarity	NPD4967	Phase 2
0.7447	Intermediate Similarity	NPD6331	Phase 2
0.7438	Intermediate Similarity	NPD1358	Approved
0.7436	Intermediate Similarity	NPD3020	Approved
0.7429	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD5585	Approved
0.7422	Intermediate Similarity	NPD5691	Approved
0.7372	Intermediate Similarity	NPD6355	Discontinued
0.7368	Intermediate Similarity	NPD7199	Phase 2
0.7368	Intermediate Similarity	NPD4624	Approved
0.7364	Intermediate Similarity	NPD2668	Approved
0.7364	Intermediate Similarity	NPD2667	Approved
0.7364	Intermediate Similarity	NPD4626	Approved
0.7355	Intermediate Similarity	NPD3134	Approved
0.7353	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6234	Discontinued
0.7348	Intermediate Similarity	NPD1283	Approved
0.7343	Intermediate Similarity	NPD7124	Phase 2
0.7333	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2978	Approved
0.7315	Intermediate Similarity	NPD2977	Approved
0.7313	Intermediate Similarity	NPD2861	Phase 2
0.7308	Intermediate Similarity	NPD3847	Discontinued
0.7305	Intermediate Similarity	NPD2808	Discontinued
0.7299	Intermediate Similarity	NPD2979	Phase 3
0.7286	Intermediate Similarity	NPD2438	Suspended
0.7286	Intermediate Similarity	NPD2161	Phase 2
0.7273	Intermediate Similarity	NPD1669	Approved
0.7273	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4236	Phase 3
0.7254	Intermediate Similarity	NPD4237	Approved
0.7231	Intermediate Similarity	NPD17	Approved
0.7231	Intermediate Similarity	NPD6516	Phase 2
0.7231	Intermediate Similarity	NPD5846	Approved
0.7218	Intermediate Similarity	NPD1876	Approved
0.7209	Intermediate Similarity	NPD1182	Approved
0.7197	Intermediate Similarity	NPD2230	Approved
0.7197	Intermediate Similarity	NPD2233	Approved
0.7197	Intermediate Similarity	NPD1840	Phase 2
0.7197	Intermediate Similarity	NPD2232	Approved
0.7194	Intermediate Similarity	NPD2653	Approved
0.7188	Intermediate Similarity	NPD3596	Phase 2
0.7185	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2860	Approved
0.7179	Intermediate Similarity	NPD2859	Approved
0.7174	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4140	Approved
0.7174	Intermediate Similarity	NPD1613	Approved
0.7163	Intermediate Similarity	NPD3539	Phase 1
0.7143	Intermediate Similarity	NPD7119	Phase 2
0.7143	Intermediate Similarity	NPD4359	Approved
0.7143	Intermediate Similarity	NPD3685	Discontinued
0.7143	Intermediate Similarity	NPD6111	Discontinued
0.7133	Intermediate Similarity	NPD4162	Approved
0.7133	Intermediate Similarity	NPD3060	Approved
0.7133	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4908	Phase 1
0.7123	Intermediate Similarity	NPD4584	Approved
0.7122	Intermediate Similarity	NPD1933	Approved
0.7122	Intermediate Similarity	NPD5735	Approved
0.7121	Intermediate Similarity	NPD1611	Approved
0.7113	Intermediate Similarity	NPD3540	Phase 1
0.7113	Intermediate Similarity	NPD7266	Discontinued
0.7111	Intermediate Similarity	NPD2798	Approved
0.7111	Intermediate Similarity	NPD6584	Phase 3
0.7109	Intermediate Similarity	NPD6671	Approved
0.7103	Intermediate Similarity	NPD5058	Phase 3
0.7101	Intermediate Similarity	NPD2674	Phase 3
0.7101	Intermediate Similarity	NPD8032	Phase 2
0.7095	Intermediate Similarity	NPD4210	Discontinued
0.7094	Intermediate Similarity	NPD2933	Approved
0.7094	Intermediate Similarity	NPD2934	Approved
0.7077	Intermediate Similarity	NPD6581	Approved
0.7077	Intermediate Similarity	NPD6580	Approved
0.7071	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3972	Approved
0.7068	Intermediate Similarity	NPD1608	Approved
0.7067	Intermediate Similarity	NPD6873	Phase 2
0.705	Intermediate Similarity	NPD1558	Phase 1
0.7042	Intermediate Similarity	NPD2531	Phase 2
0.7034	Intermediate Similarity	NPD5241	Discontinued
0.7029	Intermediate Similarity	NPD3144	Approved
0.7029	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3145	Approved
0.7029	Intermediate Similarity	NPD6798	Discontinued
0.7025	Intermediate Similarity	NPD7228	Approved
0.7023	Intermediate Similarity	NPD3445	Approved
0.7023	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD3444	Approved
0.7023	Intermediate Similarity	NPD3443	Approved
0.7021	Intermediate Similarity	NPD7097	Phase 1
0.7014	Intermediate Similarity	NPD5177	Phase 3
0.7007	Intermediate Similarity	NPD4739	Approved
0.6993	Remote Similarity	NPD5763	Approved
0.6993	Remote Similarity	NPD5762	Approved
0.6992	Remote Similarity	NPD1610	Phase 2
0.6992	Remote Similarity	NPD1091	Approved
0.6985	Remote Similarity	NPD7905	Discontinued
0.6977	Remote Similarity	NPD2557	Approved
0.697	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD8651	Approved
0.6963	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4097	Suspended
0.695	Remote Similarity	NPD6353	Approved
0.6948	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5604	Discontinued
0.6944	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3028	Approved
0.6935	Remote Similarity	NPD968	Approved
0.6933	Remote Similarity	NPD7458	Discontinued
0.6933	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3496	Discontinued
0.6913	Remote Similarity	NPD6030	Approved
0.6913	Remote Similarity	NPD4727	Phase 1
0.6913	Remote Similarity	NPD6031	Approved
0.6913	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3383	Approved
0.6908	Remote Similarity	NPD3384	Approved
0.6908	Remote Similarity	NPD3382	Approved
0.6889	Remote Similarity	NPD6582	Phase 2
0.6889	Remote Similarity	NPD6583	Phase 3
0.6887	Remote Similarity	NPD6875	Approved
0.6887	Remote Similarity	NPD6876	Approved
0.688	Remote Similarity	NPD290	Approved
0.6875	Remote Similarity	NPD821	Approved
0.6871	Remote Similarity	NPD7280	Phase 3
0.6871	Remote Similarity	NPD7281	Phase 3
0.6867	Remote Similarity	NPD2883	Discontinued
0.6866	Remote Similarity	NPD776	Approved
0.6861	Remote Similarity	NPD7018	Phase 2
0.6859	Remote Similarity	NPD5494	Approved
0.6857	Remote Similarity	NPD6233	Phase 2
0.6857	Remote Similarity	NPD3532	Approved
0.6857	Remote Similarity	NPD3530	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