NPASS Compound

Structure

NPC471063 OpenBabel07101719152D 48 52 0 0 1 0 0 0 0 0999 V2000 6.9520 -0.6268 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 8.3086 2.7138 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 8.7153 1.8003 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 6.9073 3.7319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7263 2.0093 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 5.4516 2.1151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6989 1.4867 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 5.4128 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3141 2.8183 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 5.9128 3.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2437 3.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1275 0.9912 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 7.1330 1.0958 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 11.1111 0.6777 0.0000 C 0 0 1 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 11.5178 -0.2359 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 10.9301 -1.0449 0.0000 C 0 0 2 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 9.9355 -0.9404 0.0000 C 0 0 1 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 4.3301 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5288 -0.0268 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 4.7084 1.4460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6934 1.3821 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 12.5124 -0.3404 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 11.3368 -1.9584 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 9.3477 -1.7494 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 6.5452 0.2868 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 4.4347 4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5343 0.0777 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 10.1166 0.7822 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 42 1 0 0 0 0 2 43 1 0 0 0 0 3 5 2 0 0 0 0 3 14 1 0 0 0 0 4 6 2 0 0 0 0 4 15 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 14 1 0 0 0 0 8 14 2 0 0 0 0 8 20 1 0 0 0 0 9 15 2 0 0 0 0 9 21 1 0 0 0 0 10 33 1 0 0 0 0 11 34 1 0 0 0 0 12 35 1 0 0 0 0 13 16 1 0 0 0 0 13 44 1 0 0 0 0 16 7 1 1 0 0 0 16 17 1 0 0 0 0 17 10 1 1 0 0 0 17 30 1 0 0 0 0 18 20 2 0 0 0 0 18 45 1 0 0 0 0 19 21 2 0 0 0 0 19 46 1 0 0 0 0 20 42 1 0 0 0 0 21 43 1 0 0 0 0 22 11 1 1 0 0 0 22 24 1 0 0 0 0 22 47 1 0 0 0 0 23 12 1 6 0 0 0 23 25 1 0 0 0 0 23 48 1 0 0 0 0 24 26 1 0 0 0 0 24 36 1 6 0 0 0 25 27 1 0 0 0 0 25 37 1 1 0 0 0 26 28 1 0 0 0 0 26 38 1 1 0 0 0 27 29 1 0 0 0 0 27 39 1 6 0 0 0 28 31 1 0 0 0 0 28 40 1 6 0 0 0 29 32 1 0 0 0 0 29 41 1 1 0 0 0 30 15 1 6 0 0 0 30 44 1 0 0 0 0 31 45 1 1 0 0 0 31 47 1 0 0 0 0 32 46 1 6 0 0 0 32 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	684.26
Volume:	644.071
LogP:	-0.202
LogD:	-0.066
LogS:	-2.686
# Rotatable Bonds:	12
TPSA:	246.68
# H-Bond Aceptor:	16
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.113
Synthetic Accessibility Score:	4.985
Fsp3:	0.625
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.541
MDCK Permeability:	8.431488822679967e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.897
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	48.34331512451172%
Volume Distribution (VD):	0.468
Pgp-substrate:	18.40015983581543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.32
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.125
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.045

ADMET: Excretion

Clearance (CL):	1.38
Half-life (T1/2):	0.627

ADMET: Toxicity

hERG Blockers:	0.404
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.207
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.611
Carcinogencity:	0.286
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC471063

Natural Product ID:	NPC471063
*Common Name:**	4,4'-O-Lariciresinol-Bis-Glucoside
IUPAC Name:	(2S,3R,4R,5S,6R)-2-(hydroxymethyl)-6-[4-[[(3S,4S,5R)-4-(hydroxymethyl)-5-[3-methoxy-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]oxolan-3-yl]methyl]-2-methoxyphenoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	PBLWZMSRSJTRHJ-SXCKUSEKSA-N
Standard InCHI:	InChI=1S/C32H44O16/c1-42-20-8-14(3-5-18(20)45-31-28(40)26(38)24(36)22(11-34)47-31)7-16-13-44-30(17(16)10-33)15-4-6-19(21(9-15)43-2)46-32-29(41)27(39)25(37)23(12-35)48-32/h3-6,8-9,16-17,22-41H,7,10-13H2,1-2H3/t16-,17-,22+,23+,24+,25+,26-,27-,28+,29+,30+,31+,32+/m1/s1
SMILES:	OC[C@@H]1O[C@H](Oc2ccc(cc2OC)C[C@@H]2CO[C@H]([C@@H]2CO)c2ccc(c(c2)OC)O[C@H]2O[C@@H](CO)[C@@H]([C@H]([C@@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL234142
PubChem CID:	44429874
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	=	11.06	%	PMID[469884]

☑ 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 NPC471063 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	415
0.1-0.2	1310
0.2-0.3	3232
0.3-0.4	7943
0.4-0.5	9815
0.5-0.6	7656
0.6-0.7	8146
0.7-0.8	3446
0.8-0.85	526
0.85-0.9	169
0.9-0.95	35
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC205796
0.9855	High Similarity	NPC276753
0.9577	High Similarity	NPC475224
0.9565	High Similarity	NPC246947
0.9507	High Similarity	NPC95392
0.9507	High Similarity	NPC35877
0.9507	High Similarity	NPC55715
0.9496	High Similarity	NPC113680
0.9496	High Similarity	NPC185307
0.9496	High Similarity	NPC278961
0.9496	High Similarity	NPC470950
0.9429	High Similarity	NPC471667
0.9429	High Similarity	NPC79429
0.9429	High Similarity	NPC470235
0.9429	High Similarity	NPC129417
0.9429	High Similarity	NPC283995
0.9429	High Similarity	NPC217635
0.9424	High Similarity	NPC476356
0.9362	High Similarity	NPC22150
0.9362	High Similarity	NPC279298
0.9362	High Similarity	NPC43508
0.9362	High Similarity	NPC38041
0.9362	High Similarity	NPC476301
0.9357	High Similarity	NPC46092
0.9353	High Similarity	NPC472711
0.9348	High Similarity	NPC156376
0.9338	High Similarity	NPC187194
0.9338	High Similarity	NPC476411
0.9296	High Similarity	NPC112861
0.9281	High Similarity	NPC106944
0.9231	High Similarity	NPC224674
0.9231	High Similarity	NPC275284
0.9231	High Similarity	NPC15956
0.9231	High Similarity	NPC193473
0.9231	High Similarity	NPC39657
0.9231	High Similarity	NPC31325
0.9231	High Similarity	NPC114505
0.9231	High Similarity	NPC213074
0.9225	High Similarity	NPC18979
0.922	High Similarity	NPC477898
0.9214	High Similarity	NPC471908
0.9167	High Similarity	NPC270751
0.9161	High Similarity	NPC93610
0.9161	High Similarity	NPC241846
0.9155	High Similarity	NPC84181
0.9149	High Similarity	NPC302506
0.9137	High Similarity	NPC470413
0.9137	High Similarity	NPC138738
0.9118	High Similarity	NPC9912
0.9103	High Similarity	NPC55158
0.9103	High Similarity	NPC286235
0.9103	High Similarity	NPC51328
0.9097	High Similarity	NPC99183
0.9078	High Similarity	NPC76871
0.9065	High Similarity	NPC52277
0.9065	High Similarity	NPC199459
0.9065	High Similarity	NPC177035
0.9044	High Similarity	NPC472024
0.9044	High Similarity	NPC80600
0.9041	High Similarity	NPC238140
0.9041	High Similarity	NPC229882
0.9041	High Similarity	NPC158635
0.9041	High Similarity	NPC98624
0.9034	High Similarity	NPC130449
0.9034	High Similarity	NPC304048
0.9034	High Similarity	NPC226153
0.9034	High Similarity	NPC248132
0.9021	High Similarity	NPC187774
0.9021	High Similarity	NPC472713
0.9021	High Similarity	NPC473046
0.9021	High Similarity	NPC179521
0.9021	High Similarity	NPC118385
0.9021	High Similarity	NPC472712
0.9014	High Similarity	NPC60249
0.9	High Similarity	NPC304152
0.8993	High Similarity	NPC184938
0.8993	High Similarity	NPC101624
0.8993	High Similarity	NPC93783
0.8986	High Similarity	NPC25821
0.8973	High Similarity	NPC44452
0.8971	High Similarity	NPC26653
0.8971	High Similarity	NPC270849
0.8958	High Similarity	NPC272619
0.8958	High Similarity	NPC469586
0.8958	High Similarity	NPC286245
0.8944	High Similarity	NPC108674
0.8936	High Similarity	NPC260842
0.8933	High Similarity	NPC11411
0.8921	High Similarity	NPC35731
0.8919	High Similarity	NPC302610
0.8919	High Similarity	NPC478268
0.8912	High Similarity	NPC472709
0.8912	High Similarity	NPC188393
0.8912	High Similarity	NPC470934
0.8912	High Similarity	NPC472710
0.8897	High Similarity	NPC125755
0.8897	High Similarity	NPC302378
0.8889	High Similarity	NPC25292
0.8889	High Similarity	NPC471065
0.8889	High Similarity	NPC253015
0.8889	High Similarity	NPC473045
0.8881	High Similarity	NPC253878
0.8881	High Similarity	NPC472714
0.8881	High Similarity	NPC5262
0.8881	High Similarity	NPC469559
0.8881	High Similarity	NPC189115
0.8873	High Similarity	NPC226547
0.8859	High Similarity	NPC61604
0.8859	High Similarity	NPC299706
0.8859	High Similarity	NPC245615
0.8859	High Similarity	NPC115466
0.8857	High Similarity	NPC236522
0.8857	High Similarity	NPC470236
0.8851	High Similarity	NPC473621
0.8832	High Similarity	NPC166040
0.8832	High Similarity	NPC248355
0.8828	High Similarity	NPC161700
0.8828	High Similarity	NPC277867
0.8828	High Similarity	NPC475096
0.8824	High Similarity	NPC149873
0.8824	High Similarity	NPC7191
0.8819	High Similarity	NPC473044
0.8816	High Similarity	NPC478269
0.8811	High Similarity	NPC470372
0.8811	High Similarity	NPC469661
0.8811	High Similarity	NPC471414
0.8794	High Similarity	NPC164857
0.8794	High Similarity	NPC77861
0.8794	High Similarity	NPC25695
0.8794	High Similarity	NPC172818
0.8792	High Similarity	NPC474442
0.8786	High Similarity	NPC47181
0.8786	High Similarity	NPC470881
0.8777	High Similarity	NPC104077
0.8777	High Similarity	NPC219671
0.8777	High Similarity	NPC254275
0.8777	High Similarity	NPC471505
0.8777	High Similarity	NPC147616
0.8777	High Similarity	NPC106739
0.8777	High Similarity	NPC259742
0.8776	High Similarity	NPC116229
0.8776	High Similarity	NPC280945
0.8767	High Similarity	NPC476865
0.8767	High Similarity	NPC190714
0.8767	High Similarity	NPC99515
0.8759	High Similarity	NPC76176
0.8759	High Similarity	NPC138227
0.8759	High Similarity	NPC469313
0.8759	High Similarity	NPC168579
0.8759	High Similarity	NPC470084
0.875	High Similarity	NPC473792
0.875	High Similarity	NPC206882
0.875	High Similarity	NPC473873
0.875	High Similarity	NPC48309
0.8741	High Similarity	NPC55793
0.8732	High Similarity	NPC185908
0.8732	High Similarity	NPC283949
0.8732	High Similarity	NPC469981
0.8723	High Similarity	NPC135777
0.8723	High Similarity	NPC142547
0.8723	High Similarity	NPC18576
0.8716	High Similarity	NPC471062
0.8716	High Similarity	NPC476398
0.8716	High Similarity	NPC94871
0.8716	High Similarity	NPC473427
0.8716	High Similarity	NPC259347
0.8716	High Similarity	NPC306890
0.8716	High Similarity	NPC476386
0.8716	High Similarity	NPC470933
0.8714	High Similarity	NPC215833
0.8714	High Similarity	NPC69513
0.8714	High Similarity	NPC6836
0.8714	High Similarity	NPC196937
0.8707	High Similarity	NPC175275
0.8707	High Similarity	NPC15538
0.8707	High Similarity	NPC227902
0.8707	High Similarity	NPC473480
0.8705	High Similarity	NPC476345
0.8705	High Similarity	NPC65942
0.8705	High Similarity	NPC248307
0.8701	High Similarity	NPC478267
0.8699	High Similarity	NPC476868
0.8699	High Similarity	NPC100998
0.8699	High Similarity	NPC476382
0.8699	High Similarity	NPC34927
0.8699	High Similarity	NPC476864
0.8699	High Similarity	NPC287615
0.8699	High Similarity	NPC216819
0.8699	High Similarity	NPC252292
0.8699	High Similarity	NPC34587
0.8699	High Similarity	NPC262182
0.8699	High Similarity	NPC476869
0.8699	High Similarity	NPC83743
0.8699	High Similarity	NPC476866
0.8693	High Similarity	NPC173726
0.8693	High Similarity	NPC241600
0.869	High Similarity	NPC37793
0.8684	High Similarity	NPC163635
0.8684	High Similarity	NPC228357
0.8681	High Similarity	NPC273932

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 NPC471063 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	751
0.2-0.3	1669
0.3-0.4	2809
0.4-0.5	1929
0.5-0.6	1073
0.6-0.7	506
0.7-0.8	83
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8552	High Similarity	NPD6674	Discontinued
0.8288	Intermediate Similarity	NPD7266	Discontinued
0.8116	Intermediate Similarity	NPD3705	Approved
0.8086	Intermediate Similarity	NPD7228	Approved
0.8077	Intermediate Similarity	NPD8455	Phase 2
0.8042	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD7240	Approved
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1613	Approved
0.7898	Intermediate Similarity	NPD37	Approved
0.7895	Intermediate Similarity	NPD5058	Phase 3
0.7888	Intermediate Similarity	NPD7199	Phase 2
0.7879	Intermediate Similarity	NPD7472	Approved
0.7879	Intermediate Similarity	NPD7074	Phase 3
0.7862	Intermediate Similarity	NPD4965	Approved
0.7862	Intermediate Similarity	NPD4967	Phase 2
0.7862	Intermediate Similarity	NPD4966	Approved
0.7857	Intermediate Similarity	NPD1091	Approved
0.7844	Intermediate Similarity	NPD7808	Phase 3
0.7818	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD2861	Phase 2
0.777	Intermediate Similarity	NPD1357	Approved
0.7764	Intermediate Similarity	NPD6234	Discontinued
0.7756	Intermediate Similarity	NPD1653	Approved
0.7724	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD5283	Phase 1
0.7683	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7251	Discontinued
0.7679	Intermediate Similarity	NPD7685	Pre-registration
0.7655	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.7647	Intermediate Similarity	NPD7843	Approved
0.7619	Intermediate Similarity	NPD6797	Phase 2
0.7613	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7157	Approved
0.7603	Intermediate Similarity	NPD4908	Phase 1
0.7582	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4536	Approved
0.7483	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7097	Phase 1
0.7483	Intermediate Similarity	NPD4538	Approved
0.7467	Intermediate Similarity	NPD5735	Approved
0.7465	Intermediate Similarity	NPD5125	Phase 3
0.7465	Intermediate Similarity	NPD5126	Approved
0.7455	Intermediate Similarity	NPD8127	Discontinued
0.7451	Intermediate Similarity	NPD1375	Discontinued
0.7448	Intermediate Similarity	NPD8651	Approved
0.74	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3620	Phase 2
0.7396	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7378	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1610	Phase 2
0.7353	Intermediate Similarity	NPD2684	Approved
0.7351	Intermediate Similarity	NPD6355	Discontinued
0.7338	Intermediate Similarity	NPD5762	Approved
0.7338	Intermediate Similarity	NPD5763	Approved
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6166	Phase 2
0.7321	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5960	Phase 3
0.732	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4108	Discontinued
0.732	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7095	Approved
0.7308	Intermediate Similarity	NPD6331	Phase 2
0.7308	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4110	Phase 3
0.7301	Intermediate Similarity	NPD2977	Approved
0.7301	Intermediate Similarity	NPD2978	Approved
0.7289	Intermediate Similarity	NPD5494	Approved
0.7285	Intermediate Similarity	NPD4060	Phase 1
0.7268	Intermediate Similarity	NPD7680	Approved
0.7267	Intermediate Similarity	NPD6559	Discontinued
0.726	Intermediate Similarity	NPD2983	Phase 2
0.726	Intermediate Similarity	NPD2982	Phase 2
0.7256	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4237	Approved
0.7244	Intermediate Similarity	NPD4236	Phase 3
0.7239	Intermediate Similarity	NPD1934	Approved
0.7238	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3051	Approved
0.7194	Intermediate Similarity	NPD228	Approved
0.7192	Intermediate Similarity	NPD2981	Phase 2
0.719	Intermediate Similarity	NPD6653	Approved
0.7181	Intermediate Similarity	NPD3018	Phase 2
0.7171	Intermediate Similarity	NPD4140	Approved
0.716	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2969	Approved
0.716	Intermediate Similarity	NPD2970	Approved
0.7152	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.7134	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7028	Phase 2
0.711	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7103	Intermediate Similarity	NPD6516	Phase 2
0.7103	Intermediate Similarity	NPD5846	Approved
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7093	Intermediate Similarity	NPD5844	Phase 1
0.7091	Intermediate Similarity	NPD5772	Approved
0.7091	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5773	Approved
0.7089	Intermediate Similarity	NPD4628	Phase 3
0.7081	Intermediate Similarity	NPD52	Approved
0.7081	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7526	Approved
0.7059	Intermediate Similarity	NPD1558	Phase 1
0.7051	Intermediate Similarity	NPD2161	Phase 2
0.705	Intermediate Similarity	NPD3021	Approved
0.705	Intermediate Similarity	NPD3022	Approved
0.7048	Intermediate Similarity	NPD3817	Phase 2
0.7044	Intermediate Similarity	NPD2677	Approved
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.703	Intermediate Similarity	NPD3382	Approved
0.703	Intermediate Similarity	NPD3384	Approved
0.703	Intermediate Similarity	NPD3383	Approved
0.7029	Intermediate Similarity	NPD290	Approved
0.7027	Intermediate Similarity	NPD3685	Discontinued
0.7027	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4749	Approved
0.7025	Intermediate Similarity	NPD4162	Approved
0.7025	Intermediate Similarity	NPD5177	Phase 3
0.7022	Intermediate Similarity	NPD6843	Phase 3
0.7022	Intermediate Similarity	NPD6842	Approved
0.7022	Intermediate Similarity	NPD6841	Approved
0.7022	Intermediate Similarity	NPD7906	Approved
0.702	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2489	Approved
0.7018	Intermediate Similarity	NPD27	Approved
0.7	Intermediate Similarity	NPD6071	Discontinued
0.6993	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6671	Approved
0.6989	Remote Similarity	NPD7312	Approved
0.6989	Remote Similarity	NPD7311	Approved
0.6989	Remote Similarity	NPD7310	Approved
0.6989	Remote Similarity	NPD7313	Approved
0.6988	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4535	Phase 3
0.6975	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4625	Phase 3
0.6968	Remote Similarity	NPD6353	Approved
0.6966	Remote Similarity	NPD1548	Phase 1
0.6959	Remote Similarity	NPD1608	Approved
0.6949	Remote Similarity	NPD7309	Approved
0.6949	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2560	Approved
0.6946	Remote Similarity	NPD2563	Approved
0.6937	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2122	Discontinued
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7119	Phase 2
0.6918	Remote Similarity	NPD1652	Phase 2
0.6918	Remote Similarity	NPD3060	Approved
0.6914	Remote Similarity	NPD4123	Phase 3
0.6912	Remote Similarity	NPD291	Approved
0.6905	Remote Similarity	NPD3882	Suspended
0.6903	Remote Similarity	NPD5124	Phase 1
0.6903	Remote Similarity	NPD3657	Discovery
0.6903	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5535	Approved
0.6899	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5536	Phase 2
0.689	Remote Similarity	NPD3686	Approved
0.689	Remote Similarity	NPD3687	Approved
0.689	Remote Similarity	NPD4210	Discontinued
0.6889	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6584	Phase 3
0.6886	Remote Similarity	NPD7819	Suspended
0.6886	Remote Similarity	NPD2801	Approved
0.6886	Remote Similarity	NPD1465	Phase 2
0.6879	Remote Similarity	NPD7033	Discontinued
0.6875	Remote Similarity	NPD7466	Approved
0.6872	Remote Similarity	NPD4663	Approved
0.6871	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4772	Phase 2
0.6867	Remote Similarity	NPD4773	Phase 2
0.6864	Remote Similarity	NPD7833	Phase 2
0.6864	Remote Similarity	NPD7831	Phase 2
0.6864	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5604	Discontinued
0.6855	Remote Similarity	NPD2424	Discontinued
0.6852	Remote Similarity	NPD1774	Approved
0.6848	Remote Similarity	NPD4005	Discontinued
0.6846	Remote Similarity	NPD2231	Phase 2
0.6846	Remote Similarity	NPD2235	Phase 2

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