NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.09
Volume:	235.088
LogP:	-0.645
LogD:	-0.472
LogS:	-0.531
# Rotatable Bonds:	5
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	3.003
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.246
MDCK Permeability:	7.603772974107414e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.253
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.418
Plasma Protein Binding (PPB):	31.94318389892578%
Volume Distribution (VD):	1.108
Pgp-substrate:	46.18512725830078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.429
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.478
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.281
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	6.418
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.216
Carcinogencity:	0.013
Eye Corrosion:	0.004
Eye Irritation:	0.265
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC165375

Natural Product ID:	NPC165375
*Common Name:**	Threo-1-C-Syringyl-Glycerol
IUPAC Name:	(1R,2R)-1-(4-hydroxy-3,5-dimethoxyphenyl)propane-1,2,3-triol
Synonyms:
Standard InCHIKey:	GIZSHQYTTBQKOQ-GMSGAONNSA-N
Standard InCHI:	InChI=1S/C11H16O6/c1-16-8-3-6(10(14)7(13)5-12)4-9(17-2)11(8)15/h3-4,7,10,12-15H,5H2,1-2H3/t7-,10-/m1/s1
SMILES:	COc1cc(cc(c1O)OC)[C@H]([C@@H](CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3400304
PubChem CID:	14237630
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17944538]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22823026]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	leaves and stems	Ha Long, Quang Ninh province, Vietnam	2014-Jul	PMID[25769817]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29792702]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14254	Kandelia candel	Species	Rhizophoraceae	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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[537145]

☑ 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 NPC165375 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	363
0.1-0.2	1640
0.2-0.3	5657
0.3-0.4	12911
0.4-0.5	4596
0.5-0.6	4837
0.6-0.7	7681
0.7-0.8	3740
0.8-0.85	759
0.85-0.9	347
0.9-0.95	156
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC220598
0.9828	High Similarity	NPC49341
0.9508	High Similarity	NPC476968
0.9508	High Similarity	NPC170844
0.9492	High Similarity	NPC470804
0.9487	High Similarity	NPC177475
0.9487	High Similarity	NPC35071
0.9487	High Similarity	NPC229401
0.9487	High Similarity	NPC148615
0.9483	High Similarity	NPC63083
0.9426	High Similarity	NPC206615
0.9426	High Similarity	NPC186843
0.9426	High Similarity	NPC470213
0.9426	High Similarity	NPC98631
0.9402	High Similarity	NPC20674
0.9402	High Similarity	NPC320987
0.9402	High Similarity	NPC135961
0.9402	High Similarity	NPC181969
0.9355	High Similarity	NPC470096
0.9355	High Similarity	NPC474017
0.9355	High Similarity	NPC470095
0.9355	High Similarity	NPC472597
0.9328	High Similarity	NPC476343
0.9316	High Similarity	NPC255675
0.931	High Similarity	NPC193067
0.928	High Similarity	NPC184447
0.928	High Similarity	NPC35932
0.928	High Similarity	NPC253105
0.928	High Similarity	NPC7903
0.928	High Similarity	NPC16208
0.928	High Similarity	NPC160991
0.928	High Similarity	NPC201587
0.9274	High Similarity	NPC472338
0.9256	High Similarity	NPC183446
0.925	High Similarity	NPC209567
0.9231	High Similarity	NPC259638
0.92	High Similarity	NPC309787
0.9194	High Similarity	NPC470258
0.9194	High Similarity	NPC3439
0.9194	High Similarity	NPC212015
0.9194	High Similarity	NPC222004
0.9194	High Similarity	NPC210623
0.9194	High Similarity	NPC273295
0.9194	High Similarity	NPC218856
0.9194	High Similarity	NPC285339
0.9194	High Similarity	NPC190629
0.9194	High Similarity	NPC202582
0.9194	High Similarity	NPC226788
0.918	High Similarity	NPC203133
0.918	High Similarity	NPC233410
0.918	High Similarity	NPC475169
0.918	High Similarity	NPC208950
0.918	High Similarity	NPC193544
0.918	High Similarity	NPC298757
0.918	High Similarity	NPC116907
0.918	High Similarity	NPC117214
0.918	High Similarity	NPC472093
0.918	High Similarity	NPC251855
0.918	High Similarity	NPC17943
0.918	High Similarity	NPC221077
0.918	High Similarity	NPC57490
0.9174	High Similarity	NPC197757
0.9174	High Similarity	NPC228922
0.9145	High Similarity	NPC221049
0.9134	High Similarity	NPC326095
0.9134	High Similarity	NPC244983
0.9134	High Similarity	NPC107478
0.9134	High Similarity	NPC287745
0.9134	High Similarity	NPC310854
0.9134	High Similarity	NPC170694
0.9127	High Similarity	NPC175067
0.9127	High Similarity	NPC470270
0.9127	High Similarity	NPC204215
0.9127	High Similarity	NPC470752
0.912	High Similarity	NPC469614
0.912	High Similarity	NPC469612
0.9106	High Similarity	NPC44748
0.9106	High Similarity	NPC18924
0.9106	High Similarity	NPC76451
0.9106	High Similarity	NPC473960
0.9106	High Similarity	NPC214406
0.9106	High Similarity	NPC28730
0.9106	High Similarity	NPC78974
0.9106	High Similarity	NPC223136
0.9106	High Similarity	NPC103823
0.9091	High Similarity	NPC262253
0.9091	High Similarity	NPC270326
0.9091	High Similarity	NPC41562
0.9091	High Similarity	NPC473411
0.9091	High Similarity	NPC71579
0.9076	High Similarity	NPC311595
0.9076	High Similarity	NPC24474
0.9062	High Similarity	NPC260898
0.9062	High Similarity	NPC472337
0.9062	High Similarity	NPC234333
0.9062	High Similarity	NPC256262
0.9062	High Similarity	NPC47398
0.9055	High Similarity	NPC475840
0.9055	High Similarity	NPC158331
0.9048	High Similarity	NPC469625
0.9048	High Similarity	NPC30043
0.9048	High Similarity	NPC469613
0.904	High Similarity	NPC158477
0.904	High Similarity	NPC10225
0.904	High Similarity	NPC58164
0.9032	High Similarity	NPC474119
0.9032	High Similarity	NPC41706
0.9032	High Similarity	NPC292056
0.9032	High Similarity	NPC210355
0.9032	High Similarity	NPC159968
0.9032	High Similarity	NPC163332
0.9032	High Similarity	NPC111247
0.9032	High Similarity	NPC319625
0.9032	High Similarity	NPC324112
0.9032	High Similarity	NPC236791
0.9032	High Similarity	NPC127587
0.9032	High Similarity	NPC82679
0.9032	High Similarity	NPC124452
0.9032	High Similarity	NPC74817
0.9032	High Similarity	NPC183181
0.9032	High Similarity	NPC118787
0.9032	High Similarity	NPC165045
0.9032	High Similarity	NPC242032
0.9032	High Similarity	NPC147821
0.9032	High Similarity	NPC293054
0.9032	High Similarity	NPC169474
0.9032	High Similarity	NPC246620
0.9032	High Similarity	NPC118533
0.9032	High Similarity	NPC282000
0.9024	High Similarity	NPC299584
0.9024	High Similarity	NPC265483
0.9024	High Similarity	NPC234400
0.9024	High Similarity	NPC60885
0.9024	High Similarity	NPC82483
0.9016	High Similarity	NPC471693
0.9016	High Similarity	NPC282496
0.9016	High Similarity	NPC136319
0.9016	High Similarity	NPC233526
0.9008	High Similarity	NPC285289
0.9	High Similarity	NPC232084
0.9	High Similarity	NPC10932
0.9	High Similarity	NPC247364
0.9	High Similarity	NPC61516
0.8992	High Similarity	NPC472334
0.8992	High Similarity	NPC306441
0.8992	High Similarity	NPC16435
0.8992	High Similarity	NPC472336
0.8968	High Similarity	NPC51840
0.8968	High Similarity	NPC311680
0.8968	High Similarity	NPC299221
0.8968	High Similarity	NPC234488
0.896	High Similarity	NPC245826
0.896	High Similarity	NPC252307
0.896	High Similarity	NPC474178
0.896	High Similarity	NPC28765
0.896	High Similarity	NPC154866
0.8952	High Similarity	NPC191037
0.8952	High Similarity	NPC112596
0.8952	High Similarity	NPC178284
0.8952	High Similarity	NPC58607
0.8943	High Similarity	NPC206487
0.8943	High Similarity	NPC5796
0.8934	High Similarity	NPC246967
0.8934	High Similarity	NPC135414
0.8926	High Similarity	NPC166759
0.8926	High Similarity	NPC199023
0.8923	High Similarity	NPC301765
0.8923	High Similarity	NPC474039
0.8923	High Similarity	NPC3072
0.8923	High Similarity	NPC46277
0.8923	High Similarity	NPC156948
0.8923	High Similarity	NPC86605
0.8917	High Similarity	NPC226629
0.8915	High Similarity	NPC474206
0.8915	High Similarity	NPC61946
0.8915	High Similarity	NPC94750
0.8915	High Similarity	NPC112939
0.8915	High Similarity	NPC121812
0.8915	High Similarity	NPC24490
0.8915	High Similarity	NPC141765
0.8915	High Similarity	NPC126409
0.8915	High Similarity	NPC112246
0.8915	High Similarity	NPC165155
0.8915	High Similarity	NPC470356
0.8915	High Similarity	NPC99572
0.8915	High Similarity	NPC34103
0.8908	High Similarity	NPC164386
0.8906	High Similarity	NPC132895
0.8906	High Similarity	NPC168059
0.8906	High Similarity	NPC229442
0.8898	High Similarity	NPC268266
0.8898	High Similarity	NPC268342
0.8898	High Similarity	NPC42760
0.8898	High Similarity	NPC220825
0.8889	High Similarity	NPC5851
0.8889	High Similarity	NPC45824
0.8889	High Similarity	NPC469963
0.8889	High Similarity	NPC204120
0.8889	High Similarity	NPC48315
0.8889	High Similarity	NPC469951

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 NPC165375 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	899
0.2-0.3	2263
0.3-0.4	2700
0.4-0.5	1474
0.5-0.6	852
0.6-0.7	529
0.7-0.8	96
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9508	High Similarity	NPD3027	Phase 3
0.8828	High Similarity	NPD1613	Approved
0.8828	High Similarity	NPD1612	Clinical (unspecified phase)
0.8718	High Similarity	NPD228	Approved
0.8583	High Similarity	NPD1530	Clinical (unspecified phase)
0.8516	High Similarity	NPD1529	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD2982	Phase 2
0.8125	Intermediate Similarity	NPD2983	Phase 2
0.8047	Intermediate Similarity	NPD2981	Phase 2
0.8016	Intermediate Similarity	NPD1357	Approved
0.8015	Intermediate Similarity	NPD3018	Phase 2
0.7972	Intermediate Similarity	NPD1653	Approved
0.7969	Intermediate Similarity	NPD3705	Approved
0.7852	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3620	Phase 2
0.7846	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD5283	Phase 1
0.7795	Intermediate Similarity	NPD1548	Phase 1
0.7794	Intermediate Similarity	NPD230	Phase 1
0.7755	Intermediate Similarity	NPD1934	Approved
0.7705	Intermediate Similarity	NPD2684	Approved
0.7692	Intermediate Similarity	NPD1091	Approved
0.7692	Intermediate Similarity	NPD1610	Phase 2
0.7687	Intermediate Similarity	NPD4908	Phase 1
0.7676	Intermediate Similarity	NPD2219	Phase 1
0.7669	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD37	Approved
0.7623	Intermediate Similarity	NPD290	Approved
0.7616	Intermediate Similarity	NPD6234	Discontinued
0.76	Intermediate Similarity	NPD7843	Approved
0.7591	Intermediate Similarity	NPD1558	Phase 1
0.7584	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2801	Approved
0.7576	Intermediate Similarity	NPD4749	Approved
0.7574	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD7157	Approved
0.7535	Intermediate Similarity	NPD3060	Approved
0.7518	Intermediate Similarity	NPD2674	Phase 3
0.7518	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD940	Approved
0.75	Intermediate Similarity	NPD291	Approved
0.75	Intermediate Similarity	NPD3022	Approved
0.75	Intermediate Similarity	NPD846	Approved
0.7484	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6166	Phase 2
0.7483	Intermediate Similarity	NPD3882	Suspended
0.7483	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4965	Approved
0.7483	Intermediate Similarity	NPD4967	Phase 2
0.7483	Intermediate Similarity	NPD4966	Approved
0.7481	Intermediate Similarity	NPD9494	Approved
0.7448	Intermediate Similarity	NPD1511	Approved
0.7436	Intermediate Similarity	NPD9296	Approved
0.7432	Intermediate Similarity	NPD4005	Discontinued
0.7431	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6111	Discontinued
0.7424	Intermediate Similarity	NPD422	Phase 1
0.7417	Intermediate Similarity	NPD1242	Phase 1
0.7413	Intermediate Similarity	NPD4237	Approved
0.7413	Intermediate Similarity	NPD1652	Phase 2
0.7413	Intermediate Similarity	NPD4236	Phase 3
0.7405	Intermediate Similarity	NPD9381	Approved
0.7405	Intermediate Similarity	NPD9384	Approved
0.7394	Intermediate Similarity	NPD3540	Phase 1
0.7389	Intermediate Similarity	NPD7228	Approved
0.7383	Intermediate Similarity	NPD4675	Approved
0.7383	Intermediate Similarity	NPD4678	Approved
0.7353	Intermediate Similarity	NPD2861	Phase 2
0.7347	Intermediate Similarity	NPD1512	Approved
0.7342	Intermediate Similarity	NPD7054	Approved
0.7329	Intermediate Similarity	NPD4357	Discontinued
0.7324	Intermediate Similarity	NPD3539	Phase 1
0.732	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD3144	Approved
0.7319	Intermediate Similarity	NPD3145	Approved
0.7313	Intermediate Similarity	NPD9622	Approved
0.7308	Intermediate Similarity	NPD5536	Phase 2
0.7303	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7472	Approved
0.7296	Intermediate Similarity	NPD7074	Phase 3
0.7292	Intermediate Similarity	NPD6674	Discontinued
0.7278	Intermediate Similarity	NPD3818	Discontinued
0.7273	Intermediate Similarity	NPD1375	Discontinued
0.7266	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3687	Approved
0.7248	Intermediate Similarity	NPD3686	Approved
0.7246	Intermediate Similarity	NPD4625	Phase 3
0.7237	Intermediate Similarity	NPD2977	Approved
0.7237	Intermediate Similarity	NPD2978	Approved
0.7222	Intermediate Similarity	NPD4750	Phase 3
0.7214	Intermediate Similarity	NPD2238	Phase 2
0.72	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6190	Approved
0.719	Intermediate Similarity	NPD3817	Phase 2
0.7183	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4538	Approved
0.7183	Intermediate Similarity	NPD4536	Approved
0.7172	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5177	Phase 3
0.7165	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6671	Approved
0.7153	Intermediate Similarity	NPD9619	Approved
0.7153	Intermediate Similarity	NPD9620	Approved
0.7153	Intermediate Similarity	NPD9621	Approved
0.7152	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD7124	Phase 2
0.7132	Intermediate Similarity	NPD8651	Approved
0.712	Intermediate Similarity	NPD968	Approved
0.7113	Intermediate Similarity	NPD6653	Approved
0.7111	Intermediate Similarity	NPD9269	Phase 2
0.7103	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7251	Discontinued
0.7095	Intermediate Similarity	NPD1774	Approved
0.7092	Intermediate Similarity	NPD4060	Phase 1
0.7075	Intermediate Similarity	NPD2677	Approved
0.7071	Intermediate Similarity	NPD597	Approved
0.7071	Intermediate Similarity	NPD598	Approved
0.7071	Intermediate Similarity	NPD601	Approved
0.707	Intermediate Similarity	NPD7199	Phase 2
0.7063	Intermediate Similarity	NPD1358	Approved
0.7059	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7808	Phase 3
0.7055	Intermediate Similarity	NPD4162	Approved
0.7055	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD821	Approved
0.705	Intermediate Similarity	NPD596	Approved
0.705	Intermediate Similarity	NPD600	Approved
0.7047	Intermediate Similarity	NPD4123	Phase 3
0.7047	Intermediate Similarity	NPD3158	Phase 1
0.7047	Intermediate Similarity	NPD3157	Approved
0.7042	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5124	Phase 1
0.7037	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6232	Discontinued
0.7021	Intermediate Similarity	NPD1136	Approved
0.7021	Intermediate Similarity	NPD1130	Approved
0.7021	Intermediate Similarity	NPD1132	Approved
0.7021	Intermediate Similarity	NPD840	Approved
0.7021	Intermediate Similarity	NPD839	Approved
0.7019	Intermediate Similarity	NPD5844	Phase 1
0.7014	Intermediate Similarity	NPD1510	Phase 2
0.7014	Intermediate Similarity	NPD5960	Phase 3
0.7014	Intermediate Similarity	NPD5588	Approved
0.7013	Intermediate Similarity	NPD5773	Approved
0.7013	Intermediate Similarity	NPD5772	Approved
0.7013	Intermediate Similarity	NPD1465	Phase 2
0.7	Intermediate Similarity	NPD52	Approved
0.7	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3180	Approved
0.7	Intermediate Similarity	NPD7526	Approved
0.7	Intermediate Similarity	NPD3179	Approved
0.6993	Remote Similarity	NPD5089	Approved
0.6993	Remote Similarity	NPD5090	Approved
0.6985	Remote Similarity	NPD2235	Phase 2
0.6985	Remote Similarity	NPD2231	Phase 2
0.698	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1240	Approved
0.6972	Remote Similarity	NPD3062	Approved
0.6972	Remote Similarity	NPD3059	Approved
0.6972	Remote Similarity	NPD3061	Approved
0.6966	Remote Similarity	NPD2161	Phase 2
0.6963	Remote Similarity	NPD3496	Discontinued
0.6959	Remote Similarity	NPD5241	Discontinued
0.6957	Remote Similarity	NPD3094	Phase 2
0.6954	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD556	Approved
0.6929	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3657	Discovery
0.6923	Remote Similarity	NPD5735	Approved
0.6923	Remote Similarity	NPD9377	Approved
0.6923	Remote Similarity	NPD447	Suspended
0.6923	Remote Similarity	NPD9379	Approved
0.6923	Remote Similarity	NPD9094	Approved
0.6918	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5058	Phase 3
0.6906	Remote Similarity	NPD859	Approved
0.6906	Remote Similarity	NPD599	Approved
0.6906	Remote Similarity	NPD858	Approved
0.6906	Remote Similarity	NPD6584	Phase 3
0.6906	Remote Similarity	NPD558	Phase 2
0.6906	Remote Similarity	NPD602	Approved
0.6903	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6233	Phase 2
0.6894	Remote Similarity	NPD7473	Discontinued
0.6892	Remote Similarity	NPD4110	Phase 3
0.6892	Remote Similarity	NPD4628	Phase 3
0.6892	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7240	Approved
0.6889	Remote Similarity	NPD5846	Approved
0.6889	Remote Similarity	NPD1778	Approved
0.6889	Remote Similarity	NPD6516	Phase 2
0.6889	Remote Similarity	NPD4626	Approved
0.6887	Remote Similarity	NPD1940	Clinical (unspecified phase)

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