NPASS Compound

Structure

NPC17348 OpenBabel07101718192D 25 28 0 0 1 0 0 0 0 0999 V2000 -1.0739 -5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4041 0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -4.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9400 -3.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8060 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -2.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4041 -0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 0.0219 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 -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 6 2 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 7 15 1 0 0 0 0 8 14 2 0 0 0 0 8 18 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 24 1 0 0 0 0 11 25 1 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 13 2 1 6 0 0 0 13 21 1 0 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.17
Volume:	356.888
LogP:	5.013
LogD:	4.19
LogS:	-6.231
# Rotatable Bonds:	3
TPSA:	36.92
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.83
Synthetic Accessibility Score:	3.317
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:	-5.075
MDCK Permeability:	4.0490729588782415e-05
Pgp-inhibitor:	0.896
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.331
30% Bioavailability (F30%):	0.263

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	96.91719818115234%
Volume Distribution (VD):	3.739
Pgp-substrate:	1.8956561088562012%

ADMET: Metabolism

CYP1A2-inhibitor:	0.519
CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.896
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.821
CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	0.965
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	15.976
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.161
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.717
Skin Sensitization:	0.154
Carcinogencity:	0.82
Eye Corrosion:	0.003
Eye Irritation:	0.079
Respiratory Toxicity:	0.434

Download Data

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

Natural Product: NPC17348

Natural Product ID:	NPC17348
*Common Name:**	(-)-Galcatin
IUPAC Name:	(5S,6S,7R)-5-(3,4-dimethoxyphenyl)-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole
Synonyms:
Standard InCHIKey:	KLVQONDOFFKFBN-BHVCSQLQSA-N
Standard InCHI:	InChI=1S/C21H24O4/c1-12-7-15-9-19-20(25-11-24-19)10-16(15)21(13(12)2)14-5-6-17(22-3)18(8-14)23-4/h5-6,8-10,12-13,21H,7,11H2,1-4H3/t12-,13+,21+/m1/s1
SMILES:	C[C@@H]1Cc2cc3c(cc2[C@@H]([C@H]1C)c1ccc(c(c1)OC)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3290509
PubChem CID:	15559452
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin 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	=	57.4	%	PMID[483636]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	58.2	%	PMID[483636]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	59.8	%	PMID[483636]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	58.7	%	PMID[483636]

☑ 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 NPC17348 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	463
0.1-0.2	1717
0.2-0.3	4174
0.3-0.4	13061
0.4-0.5	5407
0.5-0.6	7694
0.6-0.7	7410
0.7-0.8	2470
0.8-0.85	235
0.85-0.9	53
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9833	High Similarity	NPC177167
0.9508	High Similarity	NPC100129
0.9492	High Similarity	NPC344161
0.944	High Similarity	NPC227002
0.9333	High Similarity	NPC80241
0.9333	High Similarity	NPC301641
0.9077	High Similarity	NPC196420
0.9024	High Similarity	NPC249788
0.896	High Similarity	NPC274356
0.8908	High Similarity	NPC47194
0.8898	High Similarity	NPC165106
0.8889	High Similarity	NPC158737
0.888	High Similarity	NPC228771
0.888	High Similarity	NPC29008
0.888	High Similarity	NPC266705
0.8819	High Similarity	NPC226862
0.8819	High Similarity	NPC57119
0.8819	High Similarity	NPC158471
0.8819	High Similarity	NPC165128
0.881	High Similarity	NPC213711
0.881	High Similarity	NPC40352
0.879	High Similarity	NPC30462
0.875	High Similarity	NPC476748
0.875	High Similarity	NPC475815
0.875	High Similarity	NPC473264
0.8741	High Similarity	NPC137920
0.8741	High Similarity	NPC125134
0.8741	High Similarity	NPC86455
0.8731	High Similarity	NPC162851
0.8731	High Similarity	NPC218092
0.8731	High Similarity	NPC246474
0.873	High Similarity	NPC9067
0.8692	High Similarity	NPC97316
0.8682	High Similarity	NPC275950
0.8682	High Similarity	NPC233224
0.8682	High Similarity	NPC271208
0.8678	High Similarity	NPC9341
0.8678	High Similarity	NPC81067
0.8672	High Similarity	NPC277458
0.8672	High Similarity	NPC307050
0.8667	High Similarity	NPC191231
0.8644	High Similarity	NPC31279
0.8636	High Similarity	NPC474139
0.8615	High Similarity	NPC227160
0.8615	High Similarity	NPC82111
0.8615	High Similarity	NPC192255
0.8615	High Similarity	NPC476345
0.8594	High Similarity	NPC64948
0.8561	High Similarity	NPC145722
0.8561	High Similarity	NPC90083
0.8561	High Similarity	NPC256776
0.8561	High Similarity	NPC471942
0.8561	High Similarity	NPC185680
0.8561	High Similarity	NPC170779
0.856	High Similarity	NPC65933
0.856	High Similarity	NPC312713
0.856	High Similarity	NPC126935
0.856	High Similarity	NPC172676
0.856	High Similarity	NPC57268
0.856	High Similarity	NPC216929
0.8559	High Similarity	NPC127326
0.8551	High Similarity	NPC33832
0.855	High Similarity	NPC106739
0.855	High Similarity	NPC7744
0.855	High Similarity	NPC219671
0.855	High Similarity	NPC147616
0.855	High Similarity	NPC259742
0.855	High Similarity	NPC471505
0.855	High Similarity	NPC104077
0.854	High Similarity	NPC473575
0.8538	High Similarity	NPC173308
0.8538	High Similarity	NPC134764
0.8538	High Similarity	NPC171550
0.8538	High Similarity	NPC181079
0.8537	High Similarity	NPC474040
0.8485	Intermediate Similarity	NPC266848
0.8485	Intermediate Similarity	NPC169973
0.8485	Intermediate Similarity	NPC136750
0.8485	Intermediate Similarity	NPC196937
0.8485	Intermediate Similarity	NPC205915
0.845	Intermediate Similarity	NPC471986
0.8444	Intermediate Similarity	NPC178290
0.8433	Intermediate Similarity	NPC32189
0.8425	Intermediate Similarity	NPC31344
0.8425	Intermediate Similarity	NPC317769
0.8409	Intermediate Similarity	NPC65183
0.8409	Intermediate Similarity	NPC100223
0.8409	Intermediate Similarity	NPC33611
0.8409	Intermediate Similarity	NPC158526
0.8409	Intermediate Similarity	NPC261812
0.8409	Intermediate Similarity	NPC16830
0.8409	Intermediate Similarity	NPC72046
0.8409	Intermediate Similarity	NPC129687
0.8409	Intermediate Similarity	NPC171928
0.8406	Intermediate Similarity	NPC253015
0.8406	Intermediate Similarity	NPC471065
0.8406	Intermediate Similarity	NPC145304
0.84	Intermediate Similarity	NPC95614
0.84	Intermediate Similarity	NPC117780
0.84	Intermediate Similarity	NPC165133
0.84	Intermediate Similarity	NPC242885
0.84	Intermediate Similarity	NPC232316
0.84	Intermediate Similarity	NPC56214
0.84	Intermediate Similarity	NPC227217
0.8397	Intermediate Similarity	NPC63574
0.8374	Intermediate Similarity	NPC33900
0.8359	Intermediate Similarity	NPC34902
0.8359	Intermediate Similarity	NPC18449
0.8359	Intermediate Similarity	NPC121783
0.8358	Intermediate Similarity	NPC101624
0.8358	Intermediate Similarity	NPC142547
0.8358	Intermediate Similarity	NPC135777
0.8358	Intermediate Similarity	NPC184938
0.8358	Intermediate Similarity	NPC189474
0.8357	Intermediate Similarity	NPC80230
0.8357	Intermediate Similarity	NPC104024
0.8357	Intermediate Similarity	NPC65574
0.8357	Intermediate Similarity	NPC304687
0.8357	Intermediate Similarity	NPC101755
0.8345	Intermediate Similarity	NPC286245
0.8345	Intermediate Similarity	NPC272619
0.8333	Intermediate Similarity	NPC471983
0.8333	Intermediate Similarity	NPC149337
0.8321	Intermediate Similarity	NPC29599
0.832	Intermediate Similarity	NPC310338
0.832	Intermediate Similarity	NPC281298
0.832	Intermediate Similarity	NPC69670
0.8309	Intermediate Similarity	NPC201404
0.8309	Intermediate Similarity	NPC290714
0.8309	Intermediate Similarity	NPC53722
0.8309	Intermediate Similarity	NPC318575
0.8308	Intermediate Similarity	NPC98745
0.8308	Intermediate Similarity	NPC223807
0.8306	Intermediate Similarity	NPC25648
0.8298	Intermediate Similarity	NPC211296
0.8296	Intermediate Similarity	NPC143895
0.8295	Intermediate Similarity	NPC85830
0.8284	Intermediate Similarity	NPC19890
0.8284	Intermediate Similarity	NPC47181
0.8284	Intermediate Similarity	NPC110958
0.8284	Intermediate Similarity	NPC31530
0.8284	Intermediate Similarity	NPC311256
0.8281	Intermediate Similarity	NPC470887
0.8271	Intermediate Similarity	NPC14224
0.8271	Intermediate Similarity	NPC161958
0.8268	Intermediate Similarity	NPC160380
0.8268	Intermediate Similarity	NPC477886
0.8268	Intermediate Similarity	NPC38996
0.8268	Intermediate Similarity	NPC114845
0.8261	Intermediate Similarity	NPC302506
0.8258	Intermediate Similarity	NPC184814
0.8248	Intermediate Similarity	NPC216434
0.8248	Intermediate Similarity	NPC103448
0.824	Intermediate Similarity	NPC470626
0.824	Intermediate Similarity	NPC474214
0.8239	Intermediate Similarity	NPC177476
0.8239	Intermediate Similarity	NPC262455
0.8239	Intermediate Similarity	NPC127827
0.8235	Intermediate Similarity	NPC185908
0.8231	Intermediate Similarity	NPC50683
0.8231	Intermediate Similarity	NPC206882
0.8231	Intermediate Similarity	NPC112571
0.8231	Intermediate Similarity	NPC285725
0.8222	Intermediate Similarity	NPC313081
0.8222	Intermediate Similarity	NPC49235
0.8222	Intermediate Similarity	NPC25333
0.8222	Intermediate Similarity	NPC95485
0.8222	Intermediate Similarity	NPC18576
0.8222	Intermediate Similarity	NPC148893
0.8222	Intermediate Similarity	NPC150534
0.8222	Intermediate Similarity	NPC88065
0.8222	Intermediate Similarity	NPC89504
0.8209	Intermediate Similarity	NPC1474
0.8203	Intermediate Similarity	NPC85488
0.8203	Intermediate Similarity	NPC256167
0.8201	Intermediate Similarity	NPC265154
0.8188	Intermediate Similarity	NPC472711
0.8188	Intermediate Similarity	NPC323601
0.8182	Intermediate Similarity	NPC24425
0.8182	Intermediate Similarity	NPC149505
0.8182	Intermediate Similarity	NPC475722
0.8175	Intermediate Similarity	NPC156376
0.8175	Intermediate Similarity	NPC123526
0.8175	Intermediate Similarity	NPC119949
0.8175	Intermediate Similarity	NPC254625
0.8175	Intermediate Similarity	NPC193666
0.8175	Intermediate Similarity	NPC475961
0.8175	Intermediate Similarity	NPC474320
0.8175	Intermediate Similarity	NPC88640
0.8169	Intermediate Similarity	NPC77359
0.8169	Intermediate Similarity	NPC262804
0.8169	Intermediate Similarity	NPC40654
0.8162	Intermediate Similarity	NPC11453
0.8162	Intermediate Similarity	NPC121651
0.8162	Intermediate Similarity	NPC197166
0.816	Intermediate Similarity	NPC212643
0.816	Intermediate Similarity	NPC293619
0.816	Intermediate Similarity	NPC199209
0.8143	Intermediate Similarity	NPC217635
0.8143	Intermediate Similarity	NPC179521

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 NPC17348 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	997
0.2-0.3	1383
0.3-0.4	2870
0.4-0.5	1824
0.5-0.6	1041
0.6-0.7	540
0.7-0.8	107
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8898	High Similarity	NPD5283	Phase 1
0.871	High Similarity	NPD3705	Approved
0.8333	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD3657	Discovery
0.8134	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD3620	Phase 2
0.8031	Intermediate Similarity	NPD1357	Approved
0.8014	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD5327	Phase 3
0.7985	Intermediate Similarity	NPD5111	Phase 2
0.7985	Intermediate Similarity	NPD5110	Phase 2
0.7985	Intermediate Similarity	NPD5109	Approved
0.7929	Intermediate Similarity	NPD6674	Discontinued
0.7877	Intermediate Similarity	NPD7028	Phase 2
0.7874	Intermediate Similarity	NPD5536	Phase 2
0.7852	Intermediate Similarity	NPD4967	Phase 2
0.7852	Intermediate Similarity	NPD4966	Approved
0.7852	Intermediate Similarity	NPD4965	Approved
0.7832	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD4624	Approved
0.777	Intermediate Similarity	NPD4108	Discontinued
0.7752	Intermediate Similarity	NPD1651	Approved
0.7748	Intermediate Similarity	NPD6234	Discontinued
0.7727	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD1281	Approved
0.768	Intermediate Similarity	NPD228	Approved
0.7671	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD5451	Approved
0.7639	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5535	Approved
0.7615	Intermediate Similarity	NPD5691	Approved
0.7609	Intermediate Similarity	NPD4060	Phase 1
0.7609	Intermediate Similarity	NPD4140	Approved
0.7557	Intermediate Similarity	NPD4626	Approved
0.7554	Intermediate Similarity	NPD5735	Approved
0.7537	Intermediate Similarity	NPD1283	Approved
0.7536	Intermediate Similarity	NPD8032	Phase 2
0.7532	Intermediate Similarity	NPD7199	Phase 2
0.752	Intermediate Similarity	NPD3022	Approved
0.752	Intermediate Similarity	NPD3021	Approved
0.7519	Intermediate Similarity	NPD2981	Phase 2
0.7518	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2979	Phase 3
0.7465	Intermediate Similarity	NPD2438	Suspended
0.7464	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD2983	Phase 2
0.7463	Intermediate Similarity	NPD2982	Phase 2
0.7463	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6895	Approved
0.7447	Intermediate Similarity	NPD6896	Approved
0.7442	Intermediate Similarity	NPD6387	Discontinued
0.7442	Intermediate Similarity	NPD709	Approved
0.7436	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7228	Approved
0.7402	Intermediate Similarity	NPD1139	Approved
0.7402	Intermediate Similarity	NPD1137	Approved
0.7394	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7095	Approved
0.7379	Intermediate Similarity	NPD4110	Phase 3
0.7379	Intermediate Similarity	NPD6331	Phase 2
0.7379	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4097	Suspended
0.7376	Intermediate Similarity	NPD6353	Approved
0.7372	Intermediate Similarity	NPD3018	Phase 2
0.7344	Intermediate Similarity	NPD1138	Approved
0.7338	Intermediate Similarity	NPD5718	Phase 2
0.7333	Intermediate Similarity	NPD1669	Approved
0.7319	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4727	Phase 1
0.7313	Intermediate Similarity	NPD1611	Approved
0.7308	Intermediate Similarity	NPD7157	Approved
0.7302	Intermediate Similarity	NPD2684	Approved
0.7293	Intermediate Similarity	NPD3095	Discontinued
0.7279	Intermediate Similarity	NPD2922	Phase 1
0.7273	Intermediate Similarity	NPD3091	Approved
0.7266	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2492	Phase 1
0.7241	Intermediate Similarity	NPD2808	Discontinued
0.7241	Intermediate Similarity	NPD7037	Approved
0.7234	Intermediate Similarity	NPD3109	Approved
0.7234	Intermediate Similarity	NPD3110	Approved
0.7222	Intermediate Similarity	NPD7240	Approved
0.7222	Intermediate Similarity	NPD2531	Phase 2
0.7218	Intermediate Similarity	NPD3025	Approved
0.7218	Intermediate Similarity	NPD3024	Approved
0.7211	Intermediate Similarity	NPD5241	Discontinued
0.7209	Intermediate Similarity	NPD7843	Approved
0.7208	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7119	Phase 2
0.7185	Intermediate Similarity	NPD3092	Approved
0.7181	Intermediate Similarity	NPD4584	Approved
0.7172	Intermediate Similarity	NPD5762	Approved
0.7172	Intermediate Similarity	NPD5763	Approved
0.7172	Intermediate Similarity	NPD1375	Discontinued
0.7164	Intermediate Similarity	NPD5846	Approved
0.7164	Intermediate Similarity	NPD5125	Phase 3
0.7164	Intermediate Similarity	NPD5126	Approved
0.7164	Intermediate Similarity	NPD6516	Phase 2
0.7153	Intermediate Similarity	NPD1876	Approved
0.7133	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1840	Phase 2
0.7122	Intermediate Similarity	NPD2861	Phase 2
0.7115	Intermediate Similarity	NPD7833	Phase 2
0.7115	Intermediate Similarity	NPD7831	Phase 2
0.7115	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3023	Approved
0.7111	Intermediate Similarity	NPD3026	Approved
0.7105	Intermediate Similarity	NPD7458	Discontinued
0.7101	Intermediate Similarity	NPD3094	Phase 2
0.7092	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5585	Approved
0.7087	Intermediate Similarity	NPD1358	Approved
0.7083	Intermediate Similarity	NPD7097	Phase 1
0.7078	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3020	Approved
0.7071	Intermediate Similarity	NPD4908	Phase 1
0.7071	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.705	Intermediate Similarity	NPD6584	Phase 3
0.7047	Intermediate Similarity	NPD5058	Phase 3
0.7047	Intermediate Similarity	NPD7124	Phase 2
0.7042	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2667	Approved
0.7037	Intermediate Similarity	NPD4059	Approved
0.7037	Intermediate Similarity	NPD2668	Approved
0.7037	Intermediate Similarity	NPD3019	Approved
0.7032	Intermediate Similarity	NPD2977	Approved
0.7032	Intermediate Similarity	NPD2978	Approved
0.7021	Intermediate Similarity	NPD4625	Phase 3
0.702	Intermediate Similarity	NPD6273	Approved
0.7015	Intermediate Similarity	NPD6580	Approved
0.7015	Intermediate Similarity	NPD6581	Approved
0.7008	Intermediate Similarity	NPD3134	Approved
0.7007	Intermediate Similarity	NPD2233	Approved
0.7007	Intermediate Similarity	NPD2230	Approved
0.7007	Intermediate Similarity	NPD2232	Approved
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5736	Approved
0.6993	Remote Similarity	NPD1613	Approved
0.6993	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2161	Phase 2
0.6985	Remote Similarity	NPD3847	Discontinued
0.6981	Remote Similarity	NPD8127	Discontinued
0.698	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6030	Approved
0.6974	Remote Similarity	NPD6031	Approved
0.6972	Remote Similarity	NPD7294	Phase 1
0.6972	Remote Similarity	NPD6798	Discontinued
0.6963	Remote Similarity	NPD3443	Approved
0.6963	Remote Similarity	NPD3444	Approved
0.6963	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3445	Approved
0.6959	Remote Similarity	NPD4236	Phase 3
0.6959	Remote Similarity	NPD4237	Approved
0.6957	Remote Similarity	NPD4481	Phase 3
0.6946	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1933	Approved
0.6939	Remote Similarity	NPD7266	Discontinued
0.6937	Remote Similarity	NPD3051	Approved
0.6937	Remote Similarity	NPD6232	Discontinued
0.6929	Remote Similarity	NPD2798	Approved
0.6923	Remote Similarity	NPD7265	Discontinued
0.6914	Remote Similarity	NPD7473	Discontinued
0.6913	Remote Similarity	NPD7003	Approved
0.6913	Remote Similarity	NPD8166	Discontinued
0.6912	Remote Similarity	NPD2932	Approved
0.6912	Remote Similarity	NPD17	Approved
0.6908	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8651	Approved
0.6903	Remote Similarity	NPD7110	Phase 1
0.6903	Remote Similarity	NPD6873	Phase 2
0.6903	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2653	Approved
0.6897	Remote Similarity	NPD2157	Approved
0.6892	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1182	Approved
0.6887	Remote Similarity	NPD7041	Phase 2
0.6887	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3972	Approved
0.6883	Remote Similarity	NPD4005	Discontinued
0.6883	Remote Similarity	NPD4017	Approved
0.6879	Remote Similarity	NPD5978	Approved
0.6879	Remote Similarity	NPD5977	Approved
0.6875	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3539	Phase 1
0.6866	Remote Similarity	NPD3596	Phase 2
0.6863	Remote Similarity	NPD5699	Approved
0.6863	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7298	Approved
0.6849	Remote Similarity	NPD6111	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data