NPASS Compound

Structure

NPC44452 OpenBabel07101718312D 38 41 0 0 1 0 0 0 0 0999 V2000 6.9282 -4.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 2.0981 -5.3660 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 1.7321 -3.0000 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 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 1.7321 -1.0000 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 3.4641 -3.0000 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 -0.0000 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 2.5981 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 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 1.0981 -5.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 -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 3.0981 -5.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 35 1 0 0 0 0 2 36 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 16 1 0 0 0 0 5 12 2 0 0 0 0 5 17 1 0 0 0 0 6 13 2 0 0 0 0 6 18 1 0 0 0 0 7 14 2 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 8 26 1 0 0 0 0 9 15 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 26 1 0 0 0 0 11 29 1 0 0 0 0 13 14 1 0 0 0 0 14 21 1 0 0 0 0 15 21 1 0 0 0 0 15 26 1 1 0 0 0 16 17 2 0 0 0 0 16 30 1 0 0 0 0 17 35 1 0 0 0 0 18 19 2 0 0 0 0 18 36 1 0 0 0 0 19 37 1 0 0 0 0 20 10 1 6 0 0 0 20 22 1 0 0 0 0 20 38 1 0 0 0 0 21 12 1 6 0 0 0 22 23 1 0 0 0 0 22 31 1 1 0 0 0 23 24 1 0 0 0 0 23 32 1 6 0 0 0 24 25 1 0 0 0 0 24 33 1 1 0 0 0 25 37 1 6 0 0 0 25 38 1 0 0 0 0 26 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.21
Volume:	513.69
LogP:	-0.398
LogD:	-0.145
LogS:	-2.185
# Rotatable Bonds:	8
TPSA:	198.76
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.196
Synthetic Accessibility Score:	4.575
Fsp3:	0.538
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.458
MDCK Permeability:	5.4225471103563905e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.787
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	80.04544067382812%
Volume Distribution (VD):	0.549
Pgp-substrate:	17.790525436401367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.514
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.727
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.188
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.33

ADMET: Excretion

Clearance (CL):	4.302
Half-life (T1/2):	0.635

ADMET: Toxicity

hERG Blockers:	0.205
Human Hepatotoxicity (H-HT):	0.439
Drug-inuced Liver Injury (DILI):	0.229
AMES Toxicity:	0.2
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.092
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC44452

Natural Product ID:	NPC44452
*Common Name:**	Cyclo-Olivil 6-O-Beta-D-Glucoside
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(6S,7S,8S)-6-hydroxy-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-7,8-dihydro-5H-naphthalen-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	WDTFNYPORMFVPG-MNAFQOMLSA-N
Standard InCHI:	InChI=1S/C26H34O12/c1-35-17-5-12(3-4-16(17)30)21-14-7-19(37-25-24(33)23(32)22(31)20(10-28)38-25)18(36-2)6-13(14)8-26(34,11-29)15(21)9-27/h3-7,15,20-25,27-34H,8-11H2,1-2H3/t15-,20-,21+,22-,23+,24-,25-,26-/m1/s1
SMILES:	OC[C@@H]1[C@@H](c2ccc(c(c2)OC)O)c2cc(O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)c(cc2C[C@@]1(O)CO)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1911054
PubChem CID:	57393825
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
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21955940]
NPO16259	Syringa reticulata	Species	Oleaceae	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
EC50	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	39260.0	nM	PMID[496074]
NPT1	Others	Radical scavenging activity		EC50	>	100000.0	nM	PMID[496074]

☑ 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 NPC44452 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	447
0.1-0.2	1547
0.2-0.3	3615
0.3-0.4	8584
0.4-0.5	9415
0.5-0.6	5045
0.6-0.7	8218
0.7-0.8	4570
0.8-0.85	949
0.85-0.9	237
0.9-0.95	64
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9716	High Similarity	NPC286245
0.9716	High Similarity	NPC272619
0.9645	High Similarity	NPC471065
0.9645	High Similarity	NPC253015
0.9388	High Similarity	NPC21902
0.9384	High Similarity	NPC469707
0.9384	High Similarity	NPC182368
0.9384	High Similarity	NPC185955
0.9384	High Similarity	NPC9933
0.9384	High Similarity	NPC214326
0.9384	High Similarity	NPC225815
0.9384	High Similarity	NPC145979
0.9384	High Similarity	NPC260781
0.9384	High Similarity	NPC218041
0.9384	High Similarity	NPC469706
0.9384	High Similarity	NPC183380
0.9371	High Similarity	NPC283995
0.9371	High Similarity	NPC470235
0.9371	High Similarity	NPC129417
0.931	High Similarity	NPC213074
0.931	High Similarity	NPC275284
0.931	High Similarity	NPC114505
0.931	High Similarity	NPC193473
0.931	High Similarity	NPC224674
0.931	High Similarity	NPC31325
0.931	High Similarity	NPC15956
0.9301	High Similarity	NPC185307
0.9301	High Similarity	NPC470950
0.9301	High Similarity	NPC46092
0.9252	High Similarity	NPC98624
0.9241	High Similarity	NPC112861
0.9236	High Similarity	NPC164183
0.9236	High Similarity	NPC133251
0.9231	High Similarity	NPC476356
0.9225	High Similarity	NPC106944
0.922	High Similarity	NPC470413
0.922	High Similarity	NPC138738
0.9195	High Similarity	NPC475227
0.9195	High Similarity	NPC200645
0.9195	High Similarity	NPC106669
0.9172	High Similarity	NPC43508
0.9172	High Similarity	NPC38041
0.9172	High Similarity	NPC18979
0.9172	High Similarity	NPC476301
0.9172	High Similarity	NPC22150
0.9172	High Similarity	NPC279298
0.9167	High Similarity	NPC113680
0.9167	High Similarity	NPC278961
0.9161	High Similarity	NPC472711
0.9149	High Similarity	NPC52277
0.9149	High Similarity	NPC177035
0.9149	High Similarity	NPC199459
0.9128	High Similarity	NPC474442
0.9122	High Similarity	NPC475224
0.9116	High Similarity	NPC179809
0.9103	High Similarity	NPC79429
0.9103	High Similarity	NPC471667
0.9103	High Similarity	NPC84181
0.9103	High Similarity	NPC217635
0.9097	High Similarity	NPC60249
0.9097	High Similarity	NPC48309
0.9085	High Similarity	NPC304152
0.9054	High Similarity	NPC181452
0.9054	High Similarity	NPC474893
0.9054	High Similarity	NPC220006
0.9054	High Similarity	NPC475940
0.9048	High Similarity	NPC39657
0.9041	High Similarity	NPC475096
0.9034	High Similarity	NPC477898
0.9028	High Similarity	NPC76871
0.9007	High Similarity	NPC311256
0.9007	High Similarity	NPC187194
0.9007	High Similarity	NPC476411
0.8993	High Similarity	NPC472709
0.8993	High Similarity	NPC472710
0.8986	High Similarity	NPC159697
0.8986	High Similarity	NPC474940
0.8986	High Similarity	NPC474795
0.8986	High Similarity	NPC117788
0.8986	High Similarity	NPC130959
0.8986	High Similarity	NPC303013
0.8986	High Similarity	NPC290902
0.8986	High Similarity	NPC291326
0.8986	High Similarity	NPC474856
0.8986	High Similarity	NPC474834
0.898	High Similarity	NPC125755
0.898	High Similarity	NPC190714
0.898	High Similarity	NPC99515
0.8973	High Similarity	NPC473045
0.8973	High Similarity	NPC471063
0.8973	High Similarity	NPC25292
0.8966	High Similarity	NPC189115
0.8966	High Similarity	NPC5262
0.8966	High Similarity	NPC469559
0.8966	High Similarity	NPC246947
0.8966	High Similarity	NPC472714
0.8966	High Similarity	NPC253878
0.894	High Similarity	NPC78809
0.8926	High Similarity	NPC286235
0.8926	High Similarity	NPC55158
0.8926	High Similarity	NPC51328
0.8919	High Similarity	NPC227902
0.8912	High Similarity	NPC469586
0.8912	High Similarity	NPC161700
0.8912	High Similarity	NPC277867
0.8904	High Similarity	NPC473044
0.8897	High Similarity	NPC471414
0.8897	High Similarity	NPC469661
0.8896	High Similarity	NPC478269
0.8873	High Similarity	NPC35731
0.8859	High Similarity	NPC226153
0.8859	High Similarity	NPC304048
0.8859	High Similarity	NPC130449
0.8859	High Similarity	NPC175976
0.8859	High Similarity	NPC270751
0.8859	High Similarity	NPC248132
0.8851	High Similarity	NPC205796
0.8851	High Similarity	NPC276753
0.8844	High Similarity	NPC469313
0.8844	High Similarity	NPC187774
0.8844	High Similarity	NPC472713
0.8844	High Similarity	NPC76176
0.8844	High Similarity	NPC473046
0.8844	High Similarity	NPC118385
0.8844	High Similarity	NPC168579
0.8844	High Similarity	NPC472712
0.8844	High Similarity	NPC138227
0.8839	High Similarity	NPC100936
0.8839	High Similarity	NPC1253
0.8836	High Similarity	NPC302506
0.8836	High Similarity	NPC475084
0.8811	High Similarity	NPC101624
0.8811	High Similarity	NPC184938
0.8808	High Similarity	NPC2745
0.8794	High Similarity	NPC65942
0.8794	High Similarity	NPC248307
0.8792	High Similarity	NPC474397
0.8792	High Similarity	NPC473480
0.8792	High Similarity	NPC15538
0.8792	High Similarity	NPC99183
0.8782	High Similarity	NPC478267
0.8776	High Similarity	NPC37793
0.8766	High Similarity	NPC11411
0.8766	High Similarity	NPC228357
0.8759	High Similarity	NPC98777
0.8759	High Similarity	NPC212770
0.8759	High Similarity	NPC156376
0.875	High Similarity	NPC478268
0.875	High Similarity	NPC77861
0.875	High Similarity	NPC157783
0.8742	High Similarity	NPC195561
0.8742	High Similarity	NPC158784
0.8741	High Similarity	NPC471942
0.8741	High Similarity	NPC478085
0.8741	High Similarity	NPC470881
0.8733	High Similarity	NPC116229
0.8733	High Similarity	NPC280945
0.8733	High Similarity	NPC473876
0.8732	High Similarity	NPC254275
0.8725	High Similarity	NPC233980
0.8725	High Similarity	NPC241846
0.8725	High Similarity	NPC93610
0.8723	High Similarity	NPC472024
0.8723	High Similarity	NPC80600
0.8716	High Similarity	NPC473108
0.8716	High Similarity	NPC179521
0.8707	High Similarity	NPC477800
0.8707	High Similarity	NPC477794
0.8707	High Similarity	NPC477799
0.8699	High Similarity	NPC291101
0.8699	High Similarity	NPC55793
0.8699	High Similarity	NPC266197
0.8693	High Similarity	NPC245615
0.8693	High Similarity	NPC299706
0.8693	High Similarity	NPC115466
0.8693	High Similarity	NPC61604
0.869	High Similarity	NPC59324
0.869	High Similarity	NPC65530
0.8684	High Similarity	NPC302915
0.8684	High Similarity	NPC473621
0.8681	High Similarity	NPC79957
0.8671	High Similarity	NPC25821
0.8671	High Similarity	NPC25889
0.8671	High Similarity	NPC6836
0.8662	High Similarity	NPC9912
0.8658	High Similarity	NPC252292
0.8658	High Similarity	NPC34587
0.8658	High Similarity	NPC100998
0.8658	High Similarity	NPC34927
0.8658	High Similarity	NPC476382
0.8654	High Similarity	NPC185231
0.8652	High Similarity	NPC270849
0.8652	High Similarity	NPC86030
0.8652	High Similarity	NPC307110
0.8652	High Similarity	NPC5851
0.8652	High Similarity	NPC26653
0.8652	High Similarity	NPC248355
0.8652	High Similarity	NPC166040
0.8649	High Similarity	NPC252169
0.8649	High Similarity	NPC265154

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 NPC44452 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	850
0.2-0.3	1794
0.3-0.4	2712
0.4-0.5	1767
0.5-0.6	944
0.6-0.7	575
0.7-0.8	139
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9028	High Similarity	NPD6674	Discontinued
0.8509	High Similarity	NPD7228	Approved
0.8302	Intermediate Similarity	NPD6234	Discontinued
0.8255	Intermediate Similarity	NPD7266	Discontinued
0.8219	Intermediate Similarity	NPD1613	Approved
0.8219	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD37	Approved
0.8176	Intermediate Similarity	NPD4966	Approved
0.8176	Intermediate Similarity	NPD4965	Approved
0.8176	Intermediate Similarity	NPD4967	Phase 2
0.8138	Intermediate Similarity	NPD3027	Phase 3
0.7976	Intermediate Similarity	NPD7240	Approved
0.7973	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD3620	Phase 2
0.7964	Intermediate Similarity	NPD7074	Phase 3
0.7962	Intermediate Similarity	NPD1653	Approved
0.7945	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7054	Approved
0.7895	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7199	Phase 2
0.7857	Intermediate Similarity	NPD7472	Approved
0.7838	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD3705	Approved
0.7832	Intermediate Similarity	NPD1091	Approved
0.7826	Intermediate Similarity	NPD8455	Phase 2
0.7823	Intermediate Similarity	NPD4908	Phase 1
0.7755	Intermediate Similarity	NPD2861	Phase 2
0.7733	Intermediate Similarity	NPD4060	Phase 1
0.7697	Intermediate Similarity	NPD7097	Phase 1
0.7682	Intermediate Similarity	NPD5735	Approved
0.7674	Intermediate Similarity	NPD8312	Approved
0.7674	Intermediate Similarity	NPD8313	Approved
0.7665	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7251	Discontinued
0.7661	Intermediate Similarity	NPD7685	Pre-registration
0.7651	Intermediate Similarity	NPD4625	Phase 3
0.7643	Intermediate Similarity	NPD5058	Phase 3
0.7633	Intermediate Similarity	NPD3818	Discontinued
0.7616	Intermediate Similarity	NPD7808	Phase 3
0.7611	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6797	Phase 2
0.76	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD5844	Phase 1
0.7548	Intermediate Similarity	NPD5762	Approved
0.7548	Intermediate Similarity	NPD5763	Approved
0.7545	Intermediate Similarity	NPD8127	Discontinued
0.7541	Intermediate Similarity	NPD7680	Approved
0.7515	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6166	Phase 2
0.7515	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7906	Approved
0.7471	Intermediate Similarity	NPD7313	Approved
0.7471	Intermediate Similarity	NPD7310	Approved
0.7471	Intermediate Similarity	NPD7311	Approved
0.7471	Intermediate Similarity	NPD7312	Approved
0.747	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1610	Phase 2
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5125	Phase 3
0.7448	Intermediate Similarity	NPD5126	Approved
0.7447	Intermediate Similarity	NPD5283	Phase 1
0.7443	Intermediate Similarity	NPD4663	Approved
0.7439	Intermediate Similarity	NPD1934	Approved
0.7429	Intermediate Similarity	NPD7309	Approved
0.7419	Intermediate Similarity	NPD4108	Discontinued
0.7412	Intermediate Similarity	NPD27	Approved
0.7412	Intermediate Similarity	NPD2489	Approved
0.7396	Intermediate Similarity	NPD3051	Approved
0.7396	Intermediate Similarity	NPD3787	Discontinued
0.7394	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4140	Approved
0.7384	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1357	Approved
0.7375	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4577	Approved
0.7371	Intermediate Similarity	NPD4578	Approved
0.7365	Intermediate Similarity	NPD5327	Phase 3
0.7365	Intermediate Similarity	NPD4749	Approved
0.7356	Intermediate Similarity	NPD6559	Discontinued
0.7355	Intermediate Similarity	NPD4538	Approved
0.7355	Intermediate Similarity	NPD4536	Approved
0.7355	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2970	Approved
0.7353	Intermediate Similarity	NPD2969	Approved
0.7343	Intermediate Similarity	NPD7157	Approved
0.733	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD8651	Approved
0.7305	Intermediate Similarity	NPD228	Approved
0.7303	Intermediate Similarity	NPD7095	Approved
0.729	Intermediate Similarity	NPD6353	Approved
0.7267	Intermediate Similarity	NPD3094	Phase 2
0.7267	Intermediate Similarity	NPD7473	Discontinued
0.7262	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7843	Approved
0.7248	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3751	Discontinued
0.7222	Intermediate Similarity	NPD6671	Approved
0.7222	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1375	Discontinued
0.72	Intermediate Similarity	NPD6696	Suspended
0.7197	Intermediate Similarity	NPD5960	Phase 3
0.7197	Intermediate Similarity	NPD5588	Approved
0.7193	Intermediate Similarity	NPD6232	Discontinued
0.7186	Intermediate Similarity	NPD2977	Approved
0.7186	Intermediate Similarity	NPD1465	Phase 2
0.7186	Intermediate Similarity	NPD2978	Approved
0.7178	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3021	Approved
0.7163	Intermediate Similarity	NPD3022	Approved
0.7161	Intermediate Similarity	NPD1558	Phase 1
0.716	Intermediate Similarity	NPD7833	Phase 2
0.716	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7831	Phase 2
0.716	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7041	Phase 2
0.7143	Intermediate Similarity	NPD2677	Approved
0.7143	Intermediate Similarity	NPD6190	Approved
0.7133	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5124	Phase 1
0.7115	Intermediate Similarity	NPD3657	Discovery
0.7115	Intermediate Similarity	NPD6355	Discontinued
0.7115	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3092	Approved
0.7111	Intermediate Similarity	NPD6843	Phase 3
0.7111	Intermediate Similarity	NPD6842	Approved
0.7111	Intermediate Similarity	NPD6841	Approved
0.7108	Intermediate Similarity	NPD7028	Phase 2
0.7105	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2684	Approved
0.7089	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2801	Approved
0.7081	Intermediate Similarity	NPD6331	Phase 2
0.7081	Intermediate Similarity	NPD4628	Phase 3
0.7081	Intermediate Similarity	NPD4110	Phase 3
0.7081	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8166	Discontinued
0.7075	Intermediate Similarity	NPD1548	Phase 1
0.7063	Intermediate Similarity	NPD7037	Approved
0.7059	Intermediate Similarity	NPD3018	Phase 2
0.7055	Intermediate Similarity	NPD7340	Approved
0.7051	Intermediate Similarity	NPD2238	Phase 2
0.7048	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6100	Approved
0.7044	Intermediate Similarity	NPD6099	Approved
0.7041	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8053	Approved
0.7039	Intermediate Similarity	NPD8054	Approved
0.7037	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6959	Discontinued
0.7032	Intermediate Similarity	NPD6798	Discontinued
0.7024	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7549	Discontinued
0.7021	Intermediate Similarity	NPD6823	Phase 2
0.702	Intermediate Similarity	NPD2982	Phase 2
0.702	Intermediate Similarity	NPD2983	Phase 2
0.7019	Intermediate Similarity	NPD5177	Phase 3
0.7006	Intermediate Similarity	NPD4380	Phase 2
0.7005	Intermediate Similarity	NPD6777	Approved
0.7005	Intermediate Similarity	NPD6779	Approved
0.7005	Intermediate Similarity	NPD6776	Approved
0.7005	Intermediate Similarity	NPD6781	Approved
0.7005	Intermediate Similarity	NPD6782	Approved
0.7005	Intermediate Similarity	NPD6780	Approved
0.7005	Intermediate Similarity	NPD6778	Approved
0.6995	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7783	Phase 2
0.6994	Remote Similarity	NPD6071	Discontinued
0.6993	Remote Similarity	NPD4624	Approved
0.6993	Remote Similarity	NPD6584	Phase 3
0.6987	Remote Similarity	NPD6233	Phase 2
0.6984	Remote Similarity	NPD7435	Discontinued
0.6982	Remote Similarity	NPD7819	Suspended
0.6982	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5929	Approved
0.698	Remote Similarity	NPD6516	Phase 2
0.698	Remote Similarity	NPD5846	Approved
0.6977	Remote Similarity	NPD5494	Approved
0.6977	Remote Similarity	NPD4666	Phase 3
0.6975	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6273	Approved
0.6962	Remote Similarity	NPD6653	Approved
0.6959	Remote Similarity	NPD3091	Approved
0.6959	Remote Similarity	NPD7075	Discontinued
0.6954	Remote Similarity	NPD2981	Phase 2
0.6946	Remote Similarity	NPD7458	Discontinued
0.6941	Remote Similarity	NPD2563	Approved
0.6941	Remote Similarity	NPD2560	Approved
0.6941	Remote Similarity	NPD3817	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