NPASS Compound

Structure

NPC156376 OpenBabel07101718282D 37 41 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 -0.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -3.1691 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 1.9400 -3.9781 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 1 3 2 0 0 0 0 1 14 1 0 0 0 0 2 4 2 0 0 0 0 2 15 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 14 2 0 0 0 0 7 20 1 0 0 0 0 8 15 2 0 0 0 0 8 21 1 0 0 0 0 9 16 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 17 1 0 0 0 0 11 32 1 0 0 0 0 12 33 1 0 0 0 0 12 35 1 0 0 0 0 13 34 1 0 0 0 0 13 36 1 0 0 0 0 16 5 1 6 0 0 0 16 17 1 0 0 0 0 17 6 1 6 0 0 0 18 20 2 0 0 0 0 18 33 1 0 0 0 0 19 21 2 0 0 0 0 19 34 1 0 0 0 0 20 35 1 0 0 0 0 21 36 1 0 0 0 0 22 10 1 1 0 0 0 22 23 1 0 0 0 0 22 37 1 0 0 0 0 23 24 1 0 0 0 0 23 29 1 6 0 0 0 24 25 1 0 0 0 0 24 30 1 1 0 0 0 25 26 1 0 0 0 0 25 31 1 6 0 0 0 26 32 1 1 0 0 0 26 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.19
Volume:	496.344
LogP:	1.259
LogD:	1.406
LogS:	-3.245
# Rotatable Bonds:	10
TPSA:	156.53
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.287
Synthetic Accessibility Score:	4.26
Fsp3:	0.538
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.69
MDCK Permeability:	1.6616189896012656e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.738
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	97.95354461669922%
Volume Distribution (VD):	0.489
Pgp-substrate:	1.7182880640029907%

ADMET: Metabolism

CYP1A2-inhibitor:	0.36
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.186
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.219
CYP2D6-inhibitor:	0.982
CYP2D6-substrate:	0.533
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.336

ADMET: Excretion

Clearance (CL):	6.139
Half-life (T1/2):	0.574

ADMET: Toxicity

hERG Blockers:	0.453
Human Hepatotoxicity (H-HT):	0.239
Drug-inuced Liver Injury (DILI):	0.302
AMES Toxicity:	0.249
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.813
Carcinogencity:	0.849
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC156376

Natural Product ID:	NPC156376
*Common Name:**	Tetracentronside B
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[(2R,3R)-2,3-bis(1,3-benzodioxol-5-ylmethyl)-4-hydroxybutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	RYQGXMHEFILHCV-DNABOVRESA-N
Standard InCHI:	InChI=1S/C26H32O11/c27-9-16(5-14-1-3-18-20(7-14)35-12-33-18)17(6-15-2-4-19-21(8-15)36-13-34-19)11-32-26-25(31)24(30)23(29)22(10-28)37-26/h1-4,7-8,16-17,22-31H,5-6,9-13H2/t16-,17-,22+,23+,24-,25+,26+/m0/s1
SMILES:	OC[C@@H]([C@@H](Cc1ccc2c(c1)OCO2)CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)Cc1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3290507
PubChem CID:	90682210
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

*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	=	65.0	%	PMID[542978]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	64.0	%	PMID[542978]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	63.1	%	PMID[542978]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	65.2	%	PMID[542978]

☑ 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 NPC156376 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	407
0.1-0.2	1376
0.2-0.3	3398
0.3-0.4	9068
0.4-0.5	9563
0.5-0.6	5776
0.6-0.7	8659
0.7-0.8	3426
0.8-0.85	697
0.85-0.9	258
0.9-0.95	66
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.985	High Similarity	NPC471908
0.9776	High Similarity	NPC246947
0.9704	High Similarity	NPC477898
0.9632	High Similarity	NPC84181
0.9562	High Similarity	NPC22150
0.9562	High Similarity	NPC38041
0.9562	High Similarity	NPC279298
0.9556	High Similarity	NPC472711
0.9493	High Similarity	NPC205796
0.9493	High Similarity	NPC112861
0.9493	High Similarity	NPC276753
0.942	High Similarity	NPC18979
0.9416	High Similarity	NPC470950
0.9416	High Similarity	NPC185307
0.9398	High Similarity	NPC47181
0.9398	High Similarity	NPC476411
0.9348	High Similarity	NPC471667
0.9348	High Similarity	NPC217635
0.9348	High Similarity	NPC470235
0.9348	High Similarity	NPC129417
0.9348	High Similarity	NPC283995
0.9348	High Similarity	NPC79429
0.9348	High Similarity	NPC471063
0.9343	High Similarity	NPC476356
0.9343	High Similarity	NPC302506
0.9333	High Similarity	NPC469981
0.9328	High Similarity	NPC18576
0.9291	High Similarity	NPC51328
0.9291	High Similarity	NPC286235
0.9291	High Similarity	NPC55158
0.9281	High Similarity	NPC43508
0.9281	High Similarity	NPC476301
0.9281	High Similarity	NPC469586
0.9275	High Similarity	NPC46092
0.9259	High Similarity	NPC52277
0.9259	High Similarity	NPC199459
0.9259	High Similarity	NPC177035
0.9254	High Similarity	NPC187194
0.9248	High Similarity	NPC259742
0.9248	High Similarity	NPC147616
0.9248	High Similarity	NPC219671
0.9248	High Similarity	NPC104077
0.9225	High Similarity	NPC475224
0.9225	High Similarity	NPC98624
0.922	High Similarity	NPC130449
0.922	High Similarity	NPC248132
0.9209	High Similarity	NPC472712
0.9209	High Similarity	NPC473046
0.9209	High Similarity	NPC472713
0.9209	High Similarity	NPC118385
0.9209	High Similarity	NPC179521
0.9209	High Similarity	NPC187774
0.9191	High Similarity	NPC283949
0.9191	High Similarity	NPC185908
0.9191	High Similarity	NPC101807
0.9185	High Similarity	NPC142547
0.9185	High Similarity	NPC101624
0.9185	High Similarity	NPC135777
0.9185	High Similarity	NPC184938
0.9155	High Similarity	NPC35877
0.9155	High Similarity	NPC95392
0.9155	High Similarity	NPC55715
0.9149	High Similarity	NPC114505
0.9149	High Similarity	NPC15956
0.9149	High Similarity	NPC31325
0.9149	High Similarity	NPC213074
0.9149	High Similarity	NPC275284
0.9149	High Similarity	NPC224674
0.9149	High Similarity	NPC193473
0.9149	High Similarity	NPC39657
0.9137	High Similarity	NPC278961
0.9137	High Similarity	NPC113680
0.9124	High Similarity	NPC123526
0.9124	High Similarity	NPC193666
0.9124	High Similarity	NPC88640
0.9098	High Similarity	NPC134764
0.9098	High Similarity	NPC171550
0.9091	High Similarity	NPC57119
0.9091	High Similarity	NPC158471
0.9091	High Similarity	NPC238140
0.9091	High Similarity	NPC165128
0.9091	High Similarity	NPC226862
0.9085	High Similarity	NPC270751
0.9084	High Similarity	NPC213711
0.9084	High Similarity	NPC40352
0.9078	High Similarity	NPC93610
0.9078	High Similarity	NPC241846
0.9065	High Similarity	NPC5262
0.9065	High Similarity	NPC472714
0.9058	High Similarity	NPC56091
0.9058	High Similarity	NPC46591
0.9058	High Similarity	NPC226547
0.9058	High Similarity	NPC106944
0.9051	High Similarity	NPC304152
0.9051	High Similarity	NPC470413
0.9051	High Similarity	NPC138738
0.9044	High Similarity	NPC174191
0.9044	High Similarity	NPC236522
0.9044	High Similarity	NPC150534
0.9037	High Similarity	NPC169973
0.903	High Similarity	NPC227160
0.903	High Similarity	NPC82111
0.903	High Similarity	NPC9912
0.9007	High Similarity	NPC272619
0.9007	High Similarity	NPC286245
0.8993	High Similarity	NPC76871
0.8971	High Similarity	NPC35731
0.8971	High Similarity	NPC470881
0.8963	High Similarity	NPC33611
0.8963	High Similarity	NPC106739
0.8963	High Similarity	NPC7744
0.8963	High Similarity	NPC100223
0.8963	High Similarity	NPC129687
0.8963	High Similarity	NPC471505
0.8963	High Similarity	NPC171928
0.8963	High Similarity	NPC158526
0.8963	High Similarity	NPC16830
0.8958	High Similarity	NPC229882
0.8958	High Similarity	NPC158635
0.8955	High Similarity	NPC80600
0.8955	High Similarity	NPC472024
0.8955	High Similarity	NPC271208
0.8955	High Similarity	NPC233224
0.8951	High Similarity	NPC226153
0.8951	High Similarity	NPC304048
0.8947	High Similarity	NPC470084
0.8939	High Similarity	NPC206882
0.8936	High Similarity	NPC253015
0.8936	High Similarity	NPC471065
0.8929	High Similarity	NPC48309
0.8929	High Similarity	NPC60249
0.8929	High Similarity	NPC287124
0.8921	High Similarity	NPC55793
0.8921	High Similarity	NPC177868
0.8897	High Similarity	NPC266848
0.8897	High Similarity	NPC25821
0.8897	High Similarity	NPC196937
0.8897	High Similarity	NPC136750
0.8897	High Similarity	NPC6836
0.8889	High Similarity	NPC228346
0.8889	High Similarity	NPC115207
0.8889	High Similarity	NPC65942
0.8889	High Similarity	NPC158079
0.8889	High Similarity	NPC40432
0.8889	High Similarity	NPC476345
0.8889	High Similarity	NPC7171
0.8889	High Similarity	NPC248307
0.8889	High Similarity	NPC27843
0.8889	High Similarity	NPC161557
0.8881	High Similarity	NPC26653
0.8881	High Similarity	NPC270849
0.8865	High Similarity	NPC12728
0.8865	High Similarity	NPC265154
0.8865	High Similarity	NPC255566
0.8865	High Similarity	NPC298317
0.8865	High Similarity	NPC185071
0.8857	High Similarity	NPC469661
0.8851	High Similarity	NPC11411
0.8836	High Similarity	NPC478268
0.8836	High Similarity	NPC302610
0.8828	High Similarity	NPC472710
0.8828	High Similarity	NPC472709
0.8824	High Similarity	NPC181049
0.8824	High Similarity	NPC254275
0.8824	High Similarity	NPC4940
0.8824	High Similarity	NPC252833
0.8824	High Similarity	NPC207400
0.8824	High Similarity	NPC261812
0.8824	High Similarity	NPC72046
0.8824	High Similarity	NPC65183
0.8815	High Similarity	NPC275950
0.8815	High Similarity	NPC187998
0.8815	High Similarity	NPC257582
0.8815	High Similarity	NPC181079
0.8815	High Similarity	NPC77040
0.8815	High Similarity	NPC174495
0.8815	High Similarity	NPC42300
0.8815	High Similarity	NPC145305
0.8815	High Similarity	NPC242807
0.8815	High Similarity	NPC64201
0.8815	High Similarity	NPC173308
0.8815	High Similarity	NPC153739
0.8815	High Similarity	NPC92164
0.8815	High Similarity	NPC241522
0.8811	High Similarity	NPC212890
0.8806	High Similarity	NPC302378
0.8803	High Similarity	NPC25292
0.8803	High Similarity	NPC473045
0.8803	High Similarity	NPC166884
0.8803	High Similarity	NPC477701
0.8803	High Similarity	NPC141569
0.8794	High Similarity	NPC189115
0.8794	High Similarity	NPC469559
0.8794	High Similarity	NPC253878
0.8788	High Similarity	NPC34902
0.8788	High Similarity	NPC18449
0.8788	High Similarity	NPC121783
0.8784	High Similarity	NPC186316
0.8777	High Similarity	NPC474039
0.8776	High Similarity	NPC245615

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 NPC156376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	781
0.2-0.3	1674
0.3-0.4	2815
0.4-0.5	1827
0.5-0.6	1041
0.6-0.7	584
0.7-0.8	101
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD6674	Discontinued
0.8284	Intermediate Similarity	NPD3705	Approved
0.8235	Intermediate Similarity	NPD4965	Approved
0.8235	Intermediate Similarity	NPD4967	Phase 2
0.8235	Intermediate Similarity	NPD4966	Approved
0.8228	Intermediate Similarity	NPD7228	Approved
0.8201	Intermediate Similarity	NPD3027	Phase 3
0.8194	Intermediate Similarity	NPD7266	Discontinued
0.8129	Intermediate Similarity	NPD6234	Discontinued
0.8039	Intermediate Similarity	NPD37	Approved
0.8028	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD1613	Approved
0.8025	Intermediate Similarity	NPD7240	Approved
0.7926	Intermediate Similarity	NPD1357	Approved
0.7911	Intermediate Similarity	NPD7199	Phase 2
0.7883	Intermediate Similarity	NPD1091	Approved
0.7879	Intermediate Similarity	NPD5283	Phase 1
0.7867	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD2861	Phase 2
0.78	Intermediate Similarity	NPD5058	Phase 3
0.7778	Intermediate Similarity	NPD1653	Approved
0.7746	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3818	Discontinued
0.7643	Intermediate Similarity	NPD8455	Phase 2
0.7609	Intermediate Similarity	NPD5125	Phase 3
0.7609	Intermediate Similarity	NPD5126	Approved
0.759	Intermediate Similarity	NPD7685	Pre-registration
0.7576	Intermediate Similarity	NPD7074	Phase 3
0.7568	Intermediate Similarity	NPD5588	Approved
0.7534	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3620	Phase 2
0.7515	Intermediate Similarity	NPD7054	Approved
0.7515	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7157	Approved
0.7483	Intermediate Similarity	NPD5735	Approved
0.7483	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7472	Approved
0.745	Intermediate Similarity	NPD4108	Discontinued
0.7421	Intermediate Similarity	NPD2978	Approved
0.7421	Intermediate Similarity	NPD2977	Approved
0.7407	Intermediate Similarity	NPD7843	Approved
0.7394	Intermediate Similarity	NPD2983	Phase 2
0.7394	Intermediate Similarity	NPD2982	Phase 2
0.7391	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4538	Approved
0.7383	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4536	Approved
0.7379	Intermediate Similarity	NPD4908	Phase 1
0.7376	Intermediate Similarity	NPD1610	Phase 2
0.7372	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4236	Phase 3
0.7368	Intermediate Similarity	NPD4237	Approved
0.7351	Intermediate Similarity	NPD1375	Discontinued
0.7345	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7808	Phase 3
0.7333	Intermediate Similarity	NPD228	Approved
0.7333	Intermediate Similarity	NPD5960	Phase 3
0.7324	Intermediate Similarity	NPD2981	Phase 2
0.731	Intermediate Similarity	NPD3018	Phase 2
0.7284	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7680	Approved
0.7278	Intermediate Similarity	NPD7251	Discontinued
0.7267	Intermediate Similarity	NPD7097	Phase 1
0.7251	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6355	Discontinued
0.7239	Intermediate Similarity	NPD2684	Approved
0.7237	Intermediate Similarity	NPD5763	Approved
0.7237	Intermediate Similarity	NPD5762	Approved
0.7235	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7028	Phase 2
0.7222	Intermediate Similarity	NPD8651	Approved
0.7219	Intermediate Similarity	NPD6797	Phase 2
0.7211	Intermediate Similarity	NPD7095	Approved
0.7208	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4110	Phase 3
0.7208	Intermediate Similarity	NPD6331	Phase 2
0.7185	Intermediate Similarity	NPD3021	Approved
0.7185	Intermediate Similarity	NPD3022	Approved
0.7181	Intermediate Similarity	NPD4060	Phase 1
0.7176	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD1934	Approved
0.7143	Intermediate Similarity	NPD5177	Phase 3
0.7126	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6516	Phase 2
0.7113	Intermediate Similarity	NPD5846	Approved
0.7099	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6653	Approved
0.7073	Intermediate Similarity	NPD5604	Discontinued
0.7067	Intermediate Similarity	NPD4140	Approved
0.7063	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2161	Phase 2
0.7051	Intermediate Similarity	NPD6190	Approved
0.7051	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3382	Approved
0.7037	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3383	Approved
0.7037	Intermediate Similarity	NPD3384	Approved
0.7034	Intermediate Similarity	NPD5327	Phase 3
0.7032	Intermediate Similarity	NPD3060	Approved
0.7025	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6166	Phase 2
0.7024	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5536	Phase 2
0.702	Intermediate Similarity	NPD3657	Discovery
0.7006	Intermediate Similarity	NPD3051	Approved
0.7006	Intermediate Similarity	NPD3787	Discontinued
0.7	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6994	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5773	Approved
0.6994	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD8313	Approved
0.6994	Remote Similarity	NPD8312	Approved
0.6994	Remote Similarity	NPD5772	Approved
0.6993	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5494	Approved
0.6987	Remote Similarity	NPD4628	Phase 3
0.6981	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7526	Approved
0.6981	Remote Similarity	NPD52	Approved
0.6974	Remote Similarity	NPD6353	Approved
0.6972	Remote Similarity	NPD1548	Phase 1
0.6964	Remote Similarity	NPD2970	Approved
0.6964	Remote Similarity	NPD2969	Approved
0.6957	Remote Similarity	NPD4005	Discontinued
0.6954	Remote Similarity	NPD1558	Phase 1
0.6954	Remote Similarity	NPD2238	Phase 2
0.6951	Remote Similarity	NPD3817	Phase 2
0.6943	Remote Similarity	NPD2677	Approved
0.6939	Remote Similarity	NPD3094	Phase 2
0.6933	Remote Similarity	NPD5111	Phase 2
0.6933	Remote Similarity	NPD5110	Phase 2
0.6933	Remote Similarity	NPD6798	Discontinued
0.6933	Remote Similarity	NPD5109	Approved
0.6932	Remote Similarity	NPD6841	Approved
0.6932	Remote Similarity	NPD6843	Phase 3
0.6932	Remote Similarity	NPD6842	Approved
0.6928	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4162	Approved
0.6918	Remote Similarity	NPD4749	Approved
0.6918	Remote Similarity	NPD3685	Discontinued
0.6918	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4380	Phase 2
0.6913	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD290	Approved
0.691	Remote Similarity	NPD7296	Approved
0.6905	Remote Similarity	NPD6071	Discontinued
0.6901	Remote Similarity	NPD5844	Phase 1
0.6899	Remote Similarity	NPD7124	Phase 2
0.6894	Remote Similarity	NPD4210	Discontinued
0.6892	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4535	Phase 3
0.6879	Remote Similarity	NPD6671	Approved
0.6875	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4625	Phase 3
0.6849	Remote Similarity	NPD2235	Phase 2
0.6849	Remote Similarity	NPD2231	Phase 2
0.6849	Remote Similarity	NPD1608	Approved
0.6848	Remote Similarity	NPD2563	Approved
0.6848	Remote Similarity	NPD2560	Approved
0.6842	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2438	Suspended
0.6835	Remote Similarity	NPD5241	Discontinued
0.6824	Remote Similarity	NPD27	Approved
0.6824	Remote Similarity	NPD2489	Approved
0.6821	Remote Similarity	NPD5718	Phase 2
0.6821	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7119	Phase 2
0.6818	Remote Similarity	NPD6896	Approved
0.6818	Remote Similarity	NPD6895	Approved
0.6815	Remote Similarity	NPD1652	Phase 2
0.6813	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4123	Phase 3
0.6807	Remote Similarity	NPD3882	Suspended
0.68	Remote Similarity	NPD7313	Approved
0.68	Remote Similarity	NPD7312	Approved
0.68	Remote Similarity	NPD7311	Approved
0.68	Remote Similarity	NPD7310	Approved
0.6798	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4340	Discontinued
0.6796	Remote Similarity	NPD5582	Discontinued
0.6795	Remote Similarity	NPD6004	Phase 3
0.6795	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6005	Phase 3
0.6795	Remote Similarity	NPD6002	Phase 3

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