NPASS Compound

Structure

NPC470950 OpenBabel07101718222D 37 40 0 0 1 0 0 0 0 0999 V2000 -9.5367 -0.3411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1801 -3.6817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1746 -3.7862 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 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3611 -1.9591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3176 -4.3849 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 -5.3007 -2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7734 -2.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1097 -3.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7624 -2.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3557 -2.0636 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 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 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7788 -2.6636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2687 -4.6939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7569 -3.0817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -9.9434 -1.2546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 -1.7976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 33 1 0 0 0 0 2 34 1 0 0 0 0 3 6 2 0 0 0 0 3 13 1 0 0 0 0 4 5 2 0 0 0 0 4 14 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 8 13 2 0 0 0 0 8 20 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 15 1 0 0 0 0 12 35 1 0 0 0 0 15 7 1 1 0 0 0 15 16 1 0 0 0 0 16 10 1 1 0 0 0 16 25 1 0 0 0 0 17 19 2 0 0 0 0 17 29 1 0 0 0 0 18 20 2 0 0 0 0 18 36 1 0 0 0 0 19 33 1 0 0 0 0 20 34 1 0 0 0 0 21 11 1 6 0 0 0 21 22 1 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 1 0 0 0 23 24 1 0 0 0 0 23 31 1 6 0 0 0 24 26 1 0 0 0 0 24 32 1 1 0 0 0 25 14 1 6 0 0 0 25 35 1 0 0 0 0 26 36 1 6 0 0 0 26 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1405.81
Volume:	1063.203
LogP:	7.98
LogD:	2.9
LogS:	-2.497
# Rotatable Bonds:	24
TPSA:	295.45
# H-Bond Aceptor:	18
# H-Bond Donor:	11
# Rings:	6
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.018
Synthetic Accessibility Score:	4.217
Fsp3:	0.176
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.387
MDCK Permeability:	1.3249152289063204e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.983
20% Bioavailability (F20%):	0.87
30% Bioavailability (F30%):	0.631

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	113.98253631591797%
Volume Distribution (VD):	0.236
Pgp-substrate:	0.200189471244812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.608
CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.931
CYP2C19-substrate:	0.028
CYP2C9-inhibitor:	0.983
CYP2C9-substrate:	0.796
CYP2D6-inhibitor:	0.742
CYP2D6-substrate:	0.262
CYP3A4-inhibitor:	0.276
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	-1.119
Half-life (T1/2):	0.103

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.781
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.944
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.003

Download Data

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

Natural Product: NPC470950

Natural Product ID:	NPC470950
*Common Name:**	4'-O-Lariciresinol-Glucoside
IUPAC Name:	(2R,3S,4R,5R,6S)-2-[4-[[(3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	GAYKAIAESJROGN-JJFAMHGWSA-N
Standard InCHI:	InChI=1S/C26H34O11/c1-33-19-9-14(4-5-17(19)29)25-16(10-27)15(12-35-25)7-13-3-6-18(20(8-13)34-2)36-26-24(32)23(31)22(30)21(11-28)37-26/h3-6,8-9,15-16,21-32H,7,10-12H2,1-2H3/t15-,16-,21+,22+,23-,24+,25+,26+/m1/s1
SMILES:	OC[C@@H]1[C@@H](CO[C@H]1c1ccc(c(c1)OC)O)Cc1ccc(c(c1)OC)O[C@H]1O[C@@H](CO)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL233297
PubChem CID:	44429873
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
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17287127]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	12.27	%	PMID[490725]

☑ 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 NPC470950 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	401
0.1-0.2	1348
0.2-0.3	3429
0.3-0.4	8927
0.4-0.5	9766
0.5-0.6	5645
0.6-0.7	8304
0.7-0.8	3669
0.8-0.85	763
0.85-0.9	328
0.9-0.95	95
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC185307
0.9926	High Similarity	NPC129417
0.9926	High Similarity	NPC470235
0.9926	High Similarity	NPC476356
0.9926	High Similarity	NPC283995
0.9854	High Similarity	NPC22150
0.9854	High Similarity	NPC279298
0.9854	High Similarity	NPC38041
0.9853	High Similarity	NPC46092
0.9852	High Similarity	NPC472711
0.9783	High Similarity	NPC112861
0.9712	High Similarity	NPC39657
0.9712	High Similarity	NPC31325
0.9712	High Similarity	NPC213074
0.9712	High Similarity	NPC114505
0.9712	High Similarity	NPC275284
0.9712	High Similarity	NPC15956
0.9712	High Similarity	NPC224674
0.9712	High Similarity	NPC193473
0.971	High Similarity	NPC18979
0.9708	High Similarity	NPC477898
0.9638	High Similarity	NPC84181
0.9635	High Similarity	NPC246947
0.963	High Similarity	NPC470413
0.963	High Similarity	NPC138738
0.9574	High Similarity	NPC51328
0.9574	High Similarity	NPC286235
0.9574	High Similarity	NPC55158
0.9568	High Similarity	NPC43508
0.9568	High Similarity	NPC476301
0.9556	High Similarity	NPC52277
0.9556	High Similarity	NPC177035
0.9556	High Similarity	NPC199459
0.9507	High Similarity	NPC475224
0.9507	High Similarity	NPC98624
0.9504	High Similarity	NPC248132
0.9504	High Similarity	NPC130449
0.9496	High Similarity	NPC217635
0.9496	High Similarity	NPC187774
0.9496	High Similarity	NPC471063
0.9496	High Similarity	NPC472713
0.9496	High Similarity	NPC471667
0.9496	High Similarity	NPC79429
0.9496	High Similarity	NPC473046
0.9496	High Similarity	NPC118385
0.9496	High Similarity	NPC472712
0.9489	High Similarity	NPC106944
0.9481	High Similarity	NPC184938
0.9481	High Similarity	NPC101624
0.9429	High Similarity	NPC469586
0.9424	High Similarity	NPC113680
0.9424	High Similarity	NPC278961
0.9416	High Similarity	NPC156376
0.9407	High Similarity	NPC187194
0.9407	High Similarity	NPC476411
0.9371	High Similarity	NPC472709
0.9371	High Similarity	NPC472710
0.9362	High Similarity	NPC276753
0.9362	High Similarity	NPC205796
0.9357	High Similarity	NPC473045
0.9357	High Similarity	NPC25292
0.9353	High Similarity	NPC189115
0.9353	High Similarity	NPC253878
0.9353	High Similarity	NPC302506
0.9353	High Similarity	NPC472714
0.9353	High Similarity	NPC469559
0.9353	High Similarity	NPC5262
0.9343	High Similarity	NPC304152
0.931	High Similarity	NPC61604
0.931	High Similarity	NPC245615
0.931	High Similarity	NPC299706
0.931	High Similarity	NPC115466
0.9301	High Similarity	NPC44452
0.9291	High Similarity	NPC475096
0.9291	High Similarity	NPC272619
0.9291	High Similarity	NPC286245
0.9286	High Similarity	NPC473044
0.9281	High Similarity	NPC471908
0.9281	High Similarity	NPC471414
0.9281	High Similarity	NPC469661
0.927	High Similarity	NPC77861
0.9265	High Similarity	NPC470881
0.9265	High Similarity	NPC35731
0.9259	High Similarity	NPC471505
0.9259	High Similarity	NPC106739
0.9231	High Similarity	NPC270751
0.9231	High Similarity	NPC304048
0.9231	High Similarity	NPC226153
0.9225	High Similarity	NPC190714
0.9225	High Similarity	NPC99515
0.922	High Similarity	NPC253015
0.922	High Similarity	NPC471065
0.922	High Similarity	NPC179521
0.9214	High Similarity	NPC60249
0.9214	High Similarity	NPC48309
0.9197	High Similarity	NPC135777
0.9197	High Similarity	NPC142547
0.9191	High Similarity	NPC6836
0.9191	High Similarity	NPC25821
0.9185	High Similarity	NPC476345
0.9185	High Similarity	NPC65942
0.9185	High Similarity	NPC248307
0.9161	High Similarity	NPC227902
0.9143	High Similarity	NPC76871
0.9137	High Similarity	NPC193666
0.9137	High Similarity	NPC88640
0.9137	High Similarity	NPC212770
0.9137	High Similarity	NPC98777
0.9137	High Similarity	NPC123526
0.9122	High Similarity	NPC11411
0.9122	High Similarity	NPC163635
0.9122	High Similarity	NPC228357
0.9118	High Similarity	NPC252833
0.9111	High Similarity	NPC92164
0.9111	High Similarity	NPC145305
0.9111	High Similarity	NPC257582
0.9111	High Similarity	NPC80600
0.9111	High Similarity	NPC173308
0.9111	High Similarity	NPC275950
0.9111	High Similarity	NPC64201
0.9111	High Similarity	NPC181079
0.9111	High Similarity	NPC241522
0.9111	High Similarity	NPC187998
0.9111	High Similarity	NPC77040
0.9111	High Similarity	NPC472024
0.9111	High Similarity	NPC42300
0.9111	High Similarity	NPC242807
0.9111	High Similarity	NPC174495
0.9111	High Similarity	NPC153739
0.911	High Similarity	NPC478268
0.9103	High Similarity	NPC229882
0.9103	High Similarity	NPC158635
0.9097	High Similarity	NPC175976
0.9091	High Similarity	NPC93610
0.9091	High Similarity	NPC125755
0.9091	High Similarity	NPC241846
0.9078	High Similarity	NPC475084
0.9071	High Similarity	NPC55793
0.9065	High Similarity	NPC59324
0.9065	High Similarity	NPC477798
0.9065	High Similarity	NPC474039
0.9065	High Similarity	NPC65530
0.9065	High Similarity	NPC477797
0.9058	High Similarity	NPC93783
0.9051	High Similarity	NPC169973
0.9044	High Similarity	NPC9912
0.9044	High Similarity	NPC277804
0.9037	High Similarity	NPC248355
0.9037	High Similarity	NPC307110
0.9037	High Similarity	NPC166040
0.9037	High Similarity	NPC26653
0.9037	High Similarity	NPC270849
0.9037	High Similarity	NPC5851
0.9037	High Similarity	NPC86030
0.9037	High Similarity	NPC475875
0.9034	High Similarity	NPC95392
0.9034	High Similarity	NPC35877
0.9034	High Similarity	NPC55715
0.9028	High Similarity	NPC99183
0.9021	High Similarity	NPC277867
0.9021	High Similarity	NPC161700
0.9021	High Similarity	NPC307466
0.9014	High Similarity	NPC81638
0.9014	High Similarity	NPC478239
0.9007	High Similarity	NPC470372
0.9	High Similarity	NPC478269
0.8993	High Similarity	NPC177160
0.8993	High Similarity	NPC242028
0.8993	High Similarity	NPC263367
0.8993	High Similarity	NPC25695
0.8993	High Similarity	NPC29799
0.8993	High Similarity	NPC10737
0.8993	High Similarity	NPC209985
0.8993	High Similarity	NPC203230
0.8993	High Similarity	NPC172818
0.8993	High Similarity	NPC54743
0.8993	High Similarity	NPC477939
0.8993	High Similarity	NPC156502
0.8993	High Similarity	NPC478055
0.8986	High Similarity	NPC478085
0.898	High Similarity	NPC302610
0.8978	High Similarity	NPC147616
0.8978	High Similarity	NPC254275
0.8978	High Similarity	NPC219671
0.8978	High Similarity	NPC104077
0.8978	High Similarity	NPC259742
0.8966	High Similarity	NPC301961
0.8966	High Similarity	NPC166584
0.8966	High Similarity	NPC116229
0.8963	High Similarity	NPC45774
0.8963	High Similarity	NPC11258
0.8963	High Similarity	NPC252307
0.8963	High Similarity	NPC302378
0.8963	High Similarity	NPC21867
0.8963	High Similarity	NPC245826
0.8963	High Similarity	NPC184733
0.8963	High Similarity	NPC282703
0.8963	High Similarity	NPC72529
0.8963	High Similarity	NPC474178
0.8963	High Similarity	NPC470084

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 NPC470950 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	756
0.2-0.3	1689
0.3-0.4	2803
0.4-0.5	1864
0.5-0.6	1068
0.6-0.7	549
0.7-0.8	94
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8489	Intermediate Similarity	NPD3027	Phase 3
0.8483	Intermediate Similarity	NPD6674	Discontinued
0.8472	Intermediate Similarity	NPD7266	Discontinued
0.844	Intermediate Similarity	NPD1613	Approved
0.844	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7228	Approved
0.8175	Intermediate Similarity	NPD3705	Approved
0.8158	Intermediate Similarity	NPD1653	Approved
0.8156	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6234	Discontinued
0.8085	Intermediate Similarity	NPD2861	Phase 2
0.8085	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD37	Approved
0.8043	Intermediate Similarity	NPD1091	Approved
0.8037	Intermediate Similarity	NPD7074	Phase 3
0.8025	Intermediate Similarity	NPD4965	Approved
0.8025	Intermediate Similarity	NPD4967	Phase 2
0.8025	Intermediate Similarity	NPD4966	Approved
0.8025	Intermediate Similarity	NPD3818	Discontinued
0.7975	Intermediate Similarity	NPD7054	Approved
0.7956	Intermediate Similarity	NPD1357	Approved
0.7947	Intermediate Similarity	NPD5058	Phase 3
0.7937	Intermediate Similarity	NPD7199	Phase 2
0.7927	Intermediate Similarity	NPD7472	Approved
0.7831	Intermediate Similarity	NPD7685	Pre-registration
0.7808	Intermediate Similarity	NPD3620	Phase 2
0.7808	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5283	Phase 1
0.7778	Intermediate Similarity	NPD4908	Phase 1
0.7778	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7251	Discontinued
0.7725	Intermediate Similarity	NPD7240	Approved
0.7679	Intermediate Similarity	NPD7808	Phase 3
0.7673	Intermediate Similarity	NPD2978	Approved
0.7673	Intermediate Similarity	NPD8455	Phase 2
0.7673	Intermediate Similarity	NPD2977	Approved
0.7671	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6797	Phase 2
0.7664	Intermediate Similarity	NPD7157	Approved
0.766	Intermediate Similarity	NPD1610	Phase 2
0.7647	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD228	Approved
0.761	Intermediate Similarity	NPD1934	Approved
0.76	Intermediate Similarity	NPD5588	Approved
0.7574	Intermediate Similarity	NPD7843	Approved
0.7574	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4060	Phase 1
0.7533	Intermediate Similarity	NPD4536	Approved
0.7533	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4538	Approved
0.7531	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD5125	Phase 3
0.7518	Intermediate Similarity	NPD5126	Approved
0.7517	Intermediate Similarity	NPD5735	Approved
0.7515	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD1375	Discontinued
0.7481	Intermediate Similarity	NPD3022	Approved
0.7481	Intermediate Similarity	NPD3021	Approved
0.747	Intermediate Similarity	NPD6166	Phase 2
0.747	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1558	Phase 1
0.7432	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7097	Phase 1
0.7407	Intermediate Similarity	NPD2684	Approved
0.74	Intermediate Similarity	NPD6355	Discontinued
0.7386	Intermediate Similarity	NPD5763	Approved
0.7386	Intermediate Similarity	NPD5762	Approved
0.7379	Intermediate Similarity	NPD8651	Approved
0.7374	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5960	Phase 3
0.7368	Intermediate Similarity	NPD4108	Discontinued
0.7365	Intermediate Similarity	NPD7095	Approved
0.7355	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4110	Phase 3
0.7355	Intermediate Similarity	NPD6331	Phase 2
0.7351	Intermediate Similarity	NPD6653	Approved
0.7337	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2983	Phase 2
0.731	Intermediate Similarity	NPD2982	Phase 2
0.731	Intermediate Similarity	NPD4749	Approved
0.7308	Intermediate Similarity	NPD7680	Approved
0.7301	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4236	Phase 3
0.729	Intermediate Similarity	NPD4237	Approved
0.7289	Intermediate Similarity	NPD8127	Discontinued
0.7286	Intermediate Similarity	NPD6671	Approved
0.7283	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD27	Approved
0.7262	Intermediate Similarity	NPD2489	Approved
0.7256	Intermediate Similarity	NPD3882	Suspended
0.7254	Intermediate Similarity	NPD1548	Phase 1
0.7248	Intermediate Similarity	NPD4625	Phase 3
0.7244	Intermediate Similarity	NPD4628	Phase 3
0.7241	Intermediate Similarity	NPD2981	Phase 2
0.7239	Intermediate Similarity	NPD5773	Approved
0.7239	Intermediate Similarity	NPD5772	Approved
0.7239	Intermediate Similarity	NPD2801	Approved
0.723	Intermediate Similarity	NPD3018	Phase 2
0.7225	Intermediate Similarity	NPD7312	Approved
0.7225	Intermediate Similarity	NPD8312	Approved
0.7225	Intermediate Similarity	NPD7311	Approved
0.7225	Intermediate Similarity	NPD8313	Approved
0.7225	Intermediate Similarity	NPD7310	Approved
0.7225	Intermediate Similarity	NPD7313	Approved
0.7219	Intermediate Similarity	NPD4140	Approved
0.7205	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2970	Approved
0.7202	Intermediate Similarity	NPD2969	Approved
0.7197	Intermediate Similarity	NPD6190	Approved
0.7192	Intermediate Similarity	NPD5327	Phase 3
0.7184	Intermediate Similarity	NPD7309	Approved
0.7179	Intermediate Similarity	NPD5177	Phase 3
0.7179	Intermediate Similarity	NPD3060	Approved
0.717	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6584	Phase 3
0.7159	Intermediate Similarity	NPD7906	Approved
0.7153	Intermediate Similarity	NPD5846	Approved
0.7153	Intermediate Similarity	NPD6516	Phase 2
0.7152	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD3051	Approved
0.7143	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6071	Discontinued
0.7135	Intermediate Similarity	NPD5844	Phase 1
0.7126	Intermediate Similarity	NPD5494	Approved
0.7125	Intermediate Similarity	NPD52	Approved
0.7125	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7526	Approved
0.7102	Intermediate Similarity	NPD4663	Approved
0.7097	Intermediate Similarity	NPD2161	Phase 2
0.7095	Intermediate Similarity	NPD3094	Phase 2
0.7091	Intermediate Similarity	NPD2560	Approved
0.7091	Intermediate Similarity	NPD3817	Phase 2
0.7091	Intermediate Similarity	NPD2563	Approved
0.7089	Intermediate Similarity	NPD2677	Approved
0.7086	Intermediate Similarity	NPD6798	Discontinued
0.708	Intermediate Similarity	NPD290	Approved
0.7075	Intermediate Similarity	NPD3685	Discontinued
0.7075	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3382	Approved
0.7073	Intermediate Similarity	NPD3383	Approved
0.7073	Intermediate Similarity	NPD3384	Approved
0.7073	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4162	Approved
0.7067	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4123	Phase 3
0.7062	Intermediate Similarity	NPD6842	Approved
0.7062	Intermediate Similarity	NPD6841	Approved
0.7062	Intermediate Similarity	NPD6843	Phase 3
0.7055	Intermediate Similarity	NPD7028	Phase 2
0.7052	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3787	Discontinued
0.7039	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3687	Approved
0.7037	Intermediate Similarity	NPD3686	Approved
0.7032	Intermediate Similarity	NPD7033	Discontinued
0.703	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1465	Phase 2
0.7029	Intermediate Similarity	NPD4577	Approved
0.7029	Intermediate Similarity	NPD4578	Approved
0.7027	Intermediate Similarity	NPD6696	Suspended
0.7025	Intermediate Similarity	NPD4535	Phase 3
0.7025	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6353	Approved
0.7007	Intermediate Similarity	NPD2231	Phase 2
0.7007	Intermediate Similarity	NPD2235	Phase 2
0.7007	Intermediate Similarity	NPD1608	Approved
0.7007	Intermediate Similarity	NPD968	Approved
0.7006	Intermediate Similarity	NPD7075	Discontinued
0.7006	Intermediate Similarity	NPD5604	Discontinued
0.7	Intermediate Similarity	NPD1511	Approved
0.6993	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2238	Phase 2
0.6981	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD291	Approved
0.6962	Remote Similarity	NPD1652	Phase 2
0.6959	Remote Similarity	NPD6583	Phase 3
0.6959	Remote Similarity	NPD6582	Phase 2
0.6957	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7007	Discovery
0.6951	Remote Similarity	NPD4675	Approved
0.6951	Remote Similarity	NPD4678	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