NPASS Compound

Structure

NPC140151 OpenBabel07101718232D 32 34 0 0 1 0 0 0 0 0999 V2000 -4.3301 1.5000 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 -5.1962 2.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 0.0000 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 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 3.4641 0.0000 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 -6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 3.4641 -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 2.5981 0.5000 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 3 1 0 0 0 0 1 10 2 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 12 2 0 0 0 0 4 12 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 30 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 31 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 16 2 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 9 1 1 0 0 0 15 17 1 0 0 0 0 15 32 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 6 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 21 1 0 0 0 0 19 28 1 6 0 0 0 20 29 2 0 0 0 0 20 31 1 0 0 0 0 21 30 1 1 0 0 0 21 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.13
Volume:	424.34
LogP:	0.834
LogD:	0.222
LogS:	-2.305
# Rotatable Bonds:	8
TPSA:	186.37
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	3.771
Fsp3:	0.381
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.364
MDCK Permeability:	7.958622518344782e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.065
Human Intestinal Absorption (HIA):	0.95
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	95.25799560546875%
Volume Distribution (VD):	0.555
Pgp-substrate:	4.993688583374023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.136
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.238
CYP2C9-substrate:	0.222
CYP2D6-inhibitor:	0.318
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	8.389
Half-life (T1/2):	0.947

ADMET: Toxicity

hERG Blockers:	0.264
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.178
AMES Toxicity:	0.378
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.954
Carcinogencity:	0.176
Eye Corrosion:	0.003
Eye Irritation:	0.898
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC140151

Natural Product ID:	NPC140151
*Common Name:**	6''-O-Galloylsalidroside
IUPAC Name:	[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms:	6'-O-Galloylsalidroside
Standard InCHIKey:	BHUHTEAJYSUNLI-PEVLUNPASA-N
Standard InCHI:	InChI=1S/C21H24O11/c22-12-3-1-10(2-4-12)5-6-30-21-19(28)18(27)17(26)15(32-21)9-31-20(29)11-7-13(23)16(25)14(24)8-11/h1-4,7-8,15,17-19,21-28H,5-6,9H2/t15-,17-,18+,19-,21-/m1/s1
SMILES:	Oc1ccc(cc1)CCO[C@@H]1O[C@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1770695
PubChem CID:	13270048
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0001251] Gallic acid and derivatives [CHEMONTID:0003539] Galloyl esters

*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
NPO5829	Distylium racemosum	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21489793]
NPO5829	Distylium racemosum	Species	Hamamelidaceae	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
IC50	8

Activity Type	# Activity
Individual Protein	2
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3046	Individual Protein	Ribonuclease HI	Escherichia coli (strain K12)	IC50	>	20000.0	nM	PMID[557073]
NPT2	Others	Unspecified		IC50	=	1700.0	nM	PMID[557073]
NPT2	Others	Unspecified		IC50	=	3500.0	nM	PMID[557073]
NPT2	Others	Unspecified		IC50	=	17400.0	nM	PMID[557073]

☑ 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 NPC140151 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	349
0.1-0.2	1451
0.2-0.3	3364
0.3-0.4	7758
0.4-0.5	10108
0.5-0.6	5028
0.6-0.7	6183
0.7-0.8	6936
0.8-0.85	1168
0.85-0.9	256
0.9-0.95	79
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.986	High Similarity	NPC92117
0.979	High Similarity	NPC248257
0.979	High Similarity	NPC120621
0.9597	High Similarity	NPC472860
0.9592	High Similarity	NPC61152
0.9592	High Similarity	NPC205037
0.9592	High Similarity	NPC16024
0.9592	High Similarity	NPC3746
0.9592	High Similarity	NPC44260
0.958	High Similarity	NPC108455
0.951	High Similarity	NPC226738
0.951	High Similarity	NPC22176
0.951	High Similarity	NPC229036
0.951	High Similarity	NPC190587
0.951	High Similarity	NPC121573
0.947	High Similarity	NPC203020
0.947	High Similarity	NPC239966
0.9452	High Similarity	NPC75945
0.9404	High Similarity	NPC74319
0.9404	High Similarity	NPC287872
0.9404	High Similarity	NPC160780
0.9404	High Similarity	NPC289811
0.9342	High Similarity	NPC289346
0.9338	High Similarity	NPC238419
0.9338	High Similarity	NPC1913
0.9338	High Similarity	NPC172419
0.9281	High Similarity	NPC25389
0.9281	High Similarity	NPC311803
0.9281	High Similarity	NPC472859
0.9272	High Similarity	NPC247629
0.9272	High Similarity	NPC239019
0.9252	High Similarity	NPC142528
0.9247	High Similarity	NPC473867
0.9231	High Similarity	NPC225036
0.9231	High Similarity	NPC105525
0.9231	High Similarity	NPC75763
0.9231	High Similarity	NPC12218
0.9221	High Similarity	NPC14030
0.9221	High Similarity	NPC291957
0.9221	High Similarity	NPC90905
0.9221	High Similarity	NPC33298
0.9221	High Similarity	NPC285108
0.9221	High Similarity	NPC4013
0.9216	High Similarity	NPC166277
0.9216	High Similarity	NPC119125
0.9211	High Similarity	NPC135222
0.9211	High Similarity	NPC49173
0.9211	High Similarity	NPC474010
0.9205	High Similarity	NPC156624
0.9205	High Similarity	NPC172920
0.9189	High Similarity	NPC42464
0.9161	High Similarity	NPC470898
0.915	High Similarity	NPC104222
0.915	High Similarity	NPC210501
0.915	High Similarity	NPC318826
0.915	High Similarity	NPC141331
0.915	High Similarity	NPC114791
0.9145	High Similarity	NPC471405
0.9139	High Similarity	NPC194095
0.9139	High Similarity	NPC327032
0.9139	High Similarity	NPC191046
0.9128	High Similarity	NPC306343
0.9122	High Similarity	NPC43123
0.9116	High Similarity	NPC474465
0.9108	High Similarity	NPC116745
0.9091	High Similarity	NPC302583
0.9091	High Similarity	NPC310252
0.9091	High Similarity	NPC100558
0.9091	High Similarity	NPC84789
0.9085	High Similarity	NPC4747
0.9085	High Similarity	NPC226759
0.9085	High Similarity	NPC104275
0.9079	High Similarity	NPC10205
0.9079	High Similarity	NPC203757
0.9073	High Similarity	NPC105827
0.9073	High Similarity	NPC157898
0.9073	High Similarity	NPC310661
0.9038	High Similarity	NPC88043
0.9028	High Similarity	NPC239943
0.9021	High Similarity	NPC471345
0.9007	High Similarity	NPC75695
0.9007	High Similarity	NPC134905
0.9007	High Similarity	NPC36130
0.8994	High Similarity	NPC204937
0.8994	High Similarity	NPC149011
0.8987	High Similarity	NPC470271
0.8987	High Similarity	NPC311389
0.8981	High Similarity	NPC165720
0.898	High Similarity	NPC114242
0.898	High Similarity	NPC50221
0.8974	High Similarity	NPC148273
0.8961	High Similarity	NPC133984
0.8961	High Similarity	NPC187205
0.8951	High Similarity	NPC123988
0.8947	High Similarity	NPC137813
0.8931	High Similarity	NPC95421
0.8931	High Similarity	NPC658
0.8931	High Similarity	NPC198125
0.8931	High Similarity	NPC197708
0.8924	High Similarity	NPC175793
0.8917	High Similarity	NPC168822
0.8917	High Similarity	NPC121290
0.8912	High Similarity	NPC478250
0.8889	High Similarity	NPC156892
0.8882	High Similarity	NPC172033
0.8882	High Similarity	NPC175230
0.8882	High Similarity	NPC227485
0.8882	High Similarity	NPC88560
0.8881	High Similarity	NPC34293
0.8881	High Similarity	NPC287597
0.8881	High Similarity	NPC886
0.8875	High Similarity	NPC20505
0.8875	High Similarity	NPC470272
0.8875	High Similarity	NPC235260
0.8875	High Similarity	NPC155763
0.8874	High Similarity	NPC473091
0.8868	High Similarity	NPC43918
0.8868	High Similarity	NPC45400
0.8868	High Similarity	NPC261411
0.8868	High Similarity	NPC190204
0.8861	High Similarity	NPC475738
0.8854	High Similarity	NPC77660
0.8854	High Similarity	NPC189142
0.8854	High Similarity	NPC300537
0.8854	High Similarity	NPC127782
0.8854	High Similarity	NPC41009
0.8846	High Similarity	NPC24164
0.8839	High Similarity	NPC38779
0.8839	High Similarity	NPC114179
0.8839	High Similarity	NPC156818
0.8839	High Similarity	NPC68324
0.8839	High Similarity	NPC289322
0.8839	High Similarity	NPC160512
0.8831	High Similarity	NPC145425
0.8828	High Similarity	NPC78363
0.8827	High Similarity	NPC171706
0.882	High Similarity	NPC5786
0.882	High Similarity	NPC211594
0.882	High Similarity	NPC102851
0.882	High Similarity	NPC175107
0.882	High Similarity	NPC254540
0.882	High Similarity	NPC67134
0.882	High Similarity	NPC190003
0.882	High Similarity	NPC172807
0.882	High Similarity	NPC47140
0.8819	High Similarity	NPC18646
0.8816	High Similarity	NPC252979
0.8812	High Similarity	NPC138927
0.8812	High Similarity	NPC229687
0.8812	High Similarity	NPC476017
0.8808	High Similarity	NPC476394
0.8808	High Similarity	NPC111785
0.8808	High Similarity	NPC98809
0.88	High Similarity	NPC268366
0.8797	High Similarity	NPC191306
0.8797	High Similarity	NPC19709
0.8797	High Similarity	NPC270335
0.8797	High Similarity	NPC29830
0.8774	High Similarity	NPC300845
0.8774	High Similarity	NPC104983
0.8774	High Similarity	NPC250436
0.8774	High Similarity	NPC291948
0.8774	High Similarity	NPC88803
0.8773	High Similarity	NPC79736
0.8773	High Similarity	NPC67629
0.8773	High Similarity	NPC61904
0.8773	High Similarity	NPC472991
0.8773	High Similarity	NPC473713
0.8773	High Similarity	NPC472992
0.8773	High Similarity	NPC144097
0.8765	High Similarity	NPC472993
0.8765	High Similarity	NPC4390
0.8765	High Similarity	NPC163165
0.8758	High Similarity	NPC471416
0.8758	High Similarity	NPC475058
0.8758	High Similarity	NPC212748
0.8758	High Similarity	NPC244776
0.8758	High Similarity	NPC116864
0.8758	High Similarity	NPC72249
0.8758	High Similarity	NPC47521
0.8758	High Similarity	NPC34287
0.875	High Similarity	NPC473818
0.875	High Similarity	NPC229729
0.875	High Similarity	NPC205054
0.875	High Similarity	NPC45618
0.875	High Similarity	NPC31034
0.875	High Similarity	NPC149244
0.875	High Similarity	NPC48640
0.875	High Similarity	NPC146792
0.875	High Similarity	NPC58716
0.8742	High Similarity	NPC81835
0.8742	High Similarity	NPC311830
0.8742	High Similarity	NPC472969
0.8742	High Similarity	NPC277205
0.8742	High Similarity	NPC22832
0.8734	High Similarity	NPC473043
0.8734	High Similarity	NPC145847
0.8726	High Similarity	NPC24627
0.8726	High Similarity	NPC53889
0.872	High Similarity	NPC267549

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 NPC140151 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	824
0.2-0.3	1721
0.3-0.4	2732
0.4-0.5	2008
0.5-0.6	1063
0.6-0.7	365
0.7-0.8	119
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8774	High Similarity	NPD4868	Clinical (unspecified phase)
0.875	High Similarity	NPD3818	Discontinued
0.8712	High Similarity	NPD4338	Clinical (unspecified phase)
0.8681	High Similarity	NPD230	Phase 1
0.8658	High Similarity	NPD6190	Approved
0.8639	High Similarity	NPD7266	Discontinued
0.858	High Similarity	NPD7054	Approved
0.8528	High Similarity	NPD7472	Approved
0.8528	High Similarity	NPD7074	Phase 3
0.8481	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD6797	Phase 2
0.8424	Intermediate Similarity	NPD7251	Discontinued
0.8313	Intermediate Similarity	NPD7685	Pre-registration
0.8263	Intermediate Similarity	NPD7808	Phase 3
0.8258	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1934	Approved
0.8205	Intermediate Similarity	NPD1653	Approved
0.8176	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD4380	Phase 2
0.8086	Intermediate Similarity	NPD6234	Discontinued
0.8072	Intermediate Similarity	NPD7228	Approved
0.8063	Intermediate Similarity	NPD2801	Approved
0.8063	Intermediate Similarity	NPD1465	Phase 2
0.8061	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6166	Phase 2
0.8042	Intermediate Similarity	NPD9269	Phase 2
0.8012	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD37	Approved
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7963	Intermediate Similarity	NPD3882	Suspended
0.7963	Intermediate Similarity	NPD4966	Approved
0.7963	Intermediate Similarity	NPD4965	Approved
0.7963	Intermediate Similarity	NPD4967	Phase 2
0.7949	Intermediate Similarity	NPD1511	Approved
0.7949	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5844	Phase 1
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7075	Discontinued
0.7867	Intermediate Similarity	NPD943	Approved
0.7848	Intermediate Similarity	NPD1512	Approved
0.7831	Intermediate Similarity	NPD6232	Discontinued
0.7803	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5402	Approved
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7762	Intermediate Similarity	NPD9268	Approved
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.773	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7473	Discontinued
0.7684	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6801	Discontinued
0.7667	Intermediate Similarity	NPD3027	Phase 3
0.7632	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1613	Approved
0.7628	Intermediate Similarity	NPD1549	Phase 2
0.7622	Intermediate Similarity	NPD7819	Suspended
0.761	Intermediate Similarity	NPD6799	Approved
0.7578	Intermediate Similarity	NPD5403	Approved
0.7574	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7240	Approved
0.7569	Intermediate Similarity	NPD9545	Approved
0.7564	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1510	Phase 2
0.7532	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD5494	Approved
0.7486	Intermediate Similarity	NPD8312	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.7485	Intermediate Similarity	NPD3455	Phase 2
0.7472	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5353	Approved
0.7453	Intermediate Similarity	NPD5401	Approved
0.7442	Intermediate Similarity	NPD3751	Discontinued
0.7436	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3750	Approved
0.7417	Intermediate Similarity	NPD9494	Approved
0.741	Intermediate Similarity	NPD8455	Phase 2
0.7405	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5242	Approved
0.7354	Intermediate Similarity	NPD8151	Discontinued
0.7346	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6599	Discontinued
0.731	Intermediate Similarity	NPD3787	Discontinued
0.7308	Intermediate Similarity	NPD6535	Approved
0.7308	Intermediate Similarity	NPD6534	Approved
0.7303	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1240	Approved
0.7289	Intermediate Similarity	NPD6386	Approved
0.7289	Intermediate Similarity	NPD6385	Approved
0.7278	Intermediate Similarity	NPD2796	Approved
0.7278	Intermediate Similarity	NPD2935	Discontinued
0.7278	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD7435	Discontinued
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7262	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1933	Approved
0.7243	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2532	Approved
0.7239	Intermediate Similarity	NPD2534	Approved
0.7239	Intermediate Similarity	NPD2533	Approved
0.7234	Intermediate Similarity	NPD8319	Approved
0.7234	Intermediate Similarity	NPD8320	Phase 1
0.7225	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD8166	Discontinued
0.7204	Intermediate Similarity	NPD6776	Approved
0.7204	Intermediate Similarity	NPD6781	Approved
0.7204	Intermediate Similarity	NPD6782	Approved
0.7204	Intermediate Similarity	NPD6778	Approved
0.7204	Intermediate Similarity	NPD6777	Approved
0.7204	Intermediate Similarity	NPD6780	Approved
0.7204	Intermediate Similarity	NPD6779	Approved
0.7197	Intermediate Similarity	NPD1607	Approved
0.7189	Intermediate Similarity	NPD7700	Phase 2
0.7189	Intermediate Similarity	NPD7699	Phase 2
0.7181	Intermediate Similarity	NPD7680	Approved
0.7176	Intermediate Similarity	NPD3749	Approved
0.7169	Intermediate Similarity	NPD7458	Discontinued
0.7152	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6959	Discontinued
0.7151	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD447	Suspended
0.7134	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7585	Approved
0.7118	Intermediate Similarity	NPD7768	Phase 2
0.7107	Intermediate Similarity	NPD3748	Approved
0.7068	Intermediate Similarity	NPD7583	Approved
0.7065	Intermediate Similarity	NPD6213	Phase 3
0.7065	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6212	Phase 3
0.7047	Intermediate Similarity	NPD7874	Approved
0.7047	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD919	Approved
0.702	Intermediate Similarity	NPD1091	Approved
0.701	Intermediate Similarity	NPD7783	Phase 2
0.701	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6233	Phase 2
0.7	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7697	Approved
0.7	Intermediate Similarity	NPD7698	Approved
0.7	Intermediate Similarity	NPD7696	Phase 3
0.6994	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7039	Approved
0.6983	Remote Similarity	NPD7038	Approved
0.6979	Remote Similarity	NPD7584	Approved
0.6978	Remote Similarity	NPD8434	Phase 2
0.6971	Remote Similarity	NPD3926	Phase 2
0.6964	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7870	Phase 2
0.6963	Remote Similarity	NPD7871	Phase 2
0.6947	Remote Similarity	NPD6823	Phase 2
0.6943	Remote Similarity	NPD7701	Phase 2
0.6933	Remote Similarity	NPD1652	Phase 2
0.6928	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5953	Discontinued
0.6923	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4357	Discontinued
0.6867	Remote Similarity	NPD7390	Discontinued
0.6864	Remote Similarity	NPD3226	Approved
0.6863	Remote Similarity	NPD1608	Approved
0.6857	Remote Similarity	NPD1247	Approved
0.6857	Remote Similarity	NPD8127	Discontinued
0.6855	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5408	Approved
0.6852	Remote Similarity	NPD5405	Approved
0.6852	Remote Similarity	NPD5406	Approved
0.6852	Remote Similarity	NPD5404	Approved
0.6846	Remote Similarity	NPD9493	Approved
0.6845	Remote Similarity	NPD920	Approved
0.6839	Remote Similarity	NPD1203	Approved
0.6837	Remote Similarity	NPD7801	Approved
0.6835	Remote Similarity	NPD6798	Discontinued
0.6826	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5711	Approved
0.6818	Remote Similarity	NPD5710	Approved
0.6816	Remote Similarity	NPD7286	Phase 2
0.6816	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6832	Phase 2
0.679	Remote Similarity	NPD7033	Discontinued
0.6786	Remote Similarity	NPD6273	Approved
0.6782	Remote Similarity	NPD6971	Discontinued
0.6772	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5006	Approved
0.6771	Remote Similarity	NPD5005	Approved
0.6754	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7999	Approved
0.6753	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD9570	Approved
0.6748	Remote Similarity	NPD6100	Approved
0.6748	Remote Similarity	NPD6099	Approved
0.6734	Remote Similarity	NPD7930	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