NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.15
Volume:	257.918
LogP:	2.416
LogD:	2.274
LogS:	-3.853
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	3.779
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.52
MDCK Permeability:	2.0048904843861237e-05
Pgp-inhibitor:	0.769
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.571
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.418
Plasma Protein Binding (PPB):	86.05965423583984%
Volume Distribution (VD):	1.958
Pgp-substrate:	14.191596031188965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.193
CYP1A2-substrate:	0.846
CYP2C19-inhibitor:	0.662
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.356
CYP2C9-substrate:	0.819
CYP2D6-inhibitor:	0.199
CYP2D6-substrate:	0.497
CYP3A4-inhibitor:	0.767
CYP3A4-substrate:	0.651

ADMET: Excretion

Clearance (CL):	6.053
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.382
Carcinogencity:	0.104
Eye Corrosion:	0.028
Eye Irritation:	0.856
Respiratory Toxicity:	0.203

Download Data

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

Natural Product: NPC306295

Natural Product ID:	NPC306295
*Common Name:**	Laur-11-En-1,10-Diol
IUPAC Name:	2-[(1R,3R)-3-hydroxy-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol
Synonyms:
Standard InCHIKey:	OTLGMBCGSIMCIP-HUUCEWRRSA-N
Standard InCHI:	InChI=1S/C15H20O2/c1-10-5-6-12(13(16)9-10)14(3)7-8-15(4,17)11(14)2/h5-6,9,16-17H,2,7-8H2,1,3-4H3/t14-,15-/m1/s1
SMILES:	Cc1ccc(c(c1)O)[C@]1(C)CC[C@@](C1=C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463473
PubChem CID:	21778173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001272] Cresols [CHEMONTID:0001273] Meta cresols

*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
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974618]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27536968]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507571]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507571]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507571]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507571]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507571]

☑ 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 NPC306295 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	284
0.1-0.2	1662
0.2-0.3	3126
0.3-0.4	12464
0.4-0.5	9101
0.5-0.6	11122
0.6-0.7	4078
0.7-0.8	697
0.8-0.85	146
0.85-0.9	15
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC310456
0.92	High Similarity	NPC33675
0.92	High Similarity	NPC299762
0.9109	High Similarity	NPC72729
0.9048	High Similarity	NPC64586
0.9038	High Similarity	NPC53740
0.902	High Similarity	NPC252105
0.8942	High Similarity	NPC47284
0.8911	High Similarity	NPC79241
0.8911	High Similarity	NPC6597
0.8812	High Similarity	NPC312132
0.8812	High Similarity	NPC259512
0.88	High Similarity	NPC152415
0.87	High Similarity	NPC55903
0.8667	High Similarity	NPC227458
0.8667	High Similarity	NPC475225
0.8667	High Similarity	NPC218879
0.8667	High Similarity	NPC244513
0.8649	High Similarity	NPC469719
0.86	High Similarity	NPC306074
0.86	High Similarity	NPC231150
0.8598	High Similarity	NPC66834
0.8598	High Similarity	NPC204901
0.8598	High Similarity	NPC232523
0.8598	High Similarity	NPC158253
0.8585	High Similarity	NPC37802
0.8571	High Similarity	NPC471228
0.8571	High Similarity	NPC269212
0.8571	High Similarity	NPC235762
0.8558	High Similarity	NPC174911
0.8529	High Similarity	NPC222146
0.8519	High Similarity	NPC174981
0.8505	High Similarity	NPC12640
0.8505	High Similarity	NPC201662
0.8505	High Similarity	NPC99836
0.8496	Intermediate Similarity	NPC320864
0.8476	Intermediate Similarity	NPC80800
0.8476	Intermediate Similarity	NPC477685
0.8462	Intermediate Similarity	NPC252821
0.8462	Intermediate Similarity	NPC122005
0.8455	Intermediate Similarity	NPC54373
0.8455	Intermediate Similarity	NPC469912
0.8455	Intermediate Similarity	NPC224527
0.844	Intermediate Similarity	NPC19808
0.844	Intermediate Similarity	NPC33728
0.844	Intermediate Similarity	NPC299568
0.844	Intermediate Similarity	NPC186385
0.8431	Intermediate Similarity	NPC316301
0.8431	Intermediate Similarity	NPC289769
0.8431	Intermediate Similarity	NPC245187
0.8431	Intermediate Similarity	NPC27323
0.8426	Intermediate Similarity	NPC320439
0.8407	Intermediate Similarity	NPC141001
0.8396	Intermediate Similarity	NPC108497
0.8393	Intermediate Similarity	NPC471534
0.8381	Intermediate Similarity	NPC225506
0.8381	Intermediate Similarity	NPC248396
0.8381	Intermediate Similarity	NPC48730
0.8381	Intermediate Similarity	NPC129373
0.8365	Intermediate Similarity	NPC475078
0.8365	Intermediate Similarity	NPC152097
0.8333	Intermediate Similarity	NPC147284
0.8333	Intermediate Similarity	NPC155072
0.8333	Intermediate Similarity	NPC94139
0.8333	Intermediate Similarity	NPC306884
0.8333	Intermediate Similarity	NPC162314
0.8333	Intermediate Similarity	NPC469913
0.8333	Intermediate Similarity	NPC3358
0.8333	Intermediate Similarity	NPC210497
0.8318	Intermediate Similarity	NPC272029
0.8317	Intermediate Similarity	NPC192
0.83	Intermediate Similarity	NPC27974
0.8288	Intermediate Similarity	NPC470770
0.8288	Intermediate Similarity	NPC77772
0.8288	Intermediate Similarity	NPC266937
0.8288	Intermediate Similarity	NPC151537
0.8286	Intermediate Similarity	NPC92730
0.8286	Intermediate Similarity	NPC260775
0.8276	Intermediate Similarity	NPC68339
0.8273	Intermediate Similarity	NPC473524
0.8261	Intermediate Similarity	NPC206
0.8241	Intermediate Similarity	NPC117115
0.8241	Intermediate Similarity	NPC471350
0.8235	Intermediate Similarity	NPC155908
0.8224	Intermediate Similarity	NPC71002
0.8224	Intermediate Similarity	NPC242342
0.8224	Intermediate Similarity	NPC94351
0.8224	Intermediate Similarity	NPC249828
0.8224	Intermediate Similarity	NPC146798
0.8224	Intermediate Similarity	NPC53051
0.8224	Intermediate Similarity	NPC85479
0.8224	Intermediate Similarity	NPC313030
0.8224	Intermediate Similarity	NPC24404
0.8224	Intermediate Similarity	NPC106396
0.8224	Intermediate Similarity	NPC222522
0.8224	Intermediate Similarity	NPC168303
0.8224	Intermediate Similarity	NPC302219
0.8214	Intermediate Similarity	NPC166995
0.8214	Intermediate Similarity	NPC177962
0.8214	Intermediate Similarity	NPC228452
0.8214	Intermediate Similarity	NPC62867
0.8214	Intermediate Similarity	NPC250323
0.8208	Intermediate Similarity	NPC130756
0.8208	Intermediate Similarity	NPC211885
0.8208	Intermediate Similarity	NPC12931
0.8208	Intermediate Similarity	NPC10588
0.8208	Intermediate Similarity	NPC166761
0.8208	Intermediate Similarity	NPC130103
0.8208	Intermediate Similarity	NPC70677
0.8205	Intermediate Similarity	NPC328504
0.82	Intermediate Similarity	NPC407
0.82	Intermediate Similarity	NPC307235
0.8198	Intermediate Similarity	NPC224870
0.819	Intermediate Similarity	NPC474073
0.819	Intermediate Similarity	NPC77492
0.819	Intermediate Similarity	NPC225464
0.8174	Intermediate Similarity	NPC304510
0.8174	Intermediate Similarity	NPC172219
0.8173	Intermediate Similarity	NPC144682
0.8165	Intermediate Similarity	NPC477814
0.8165	Intermediate Similarity	NPC21594
0.8158	Intermediate Similarity	NPC84999
0.8158	Intermediate Similarity	NPC246760
0.8155	Intermediate Similarity	NPC29373
0.8148	Intermediate Similarity	NPC120719
0.8148	Intermediate Similarity	NPC238696
0.8148	Intermediate Similarity	NPC475580
0.8148	Intermediate Similarity	NPC102216
0.8142	Intermediate Similarity	NPC319803
0.8142	Intermediate Similarity	NPC23804
0.8142	Intermediate Similarity	NPC117846
0.8142	Intermediate Similarity	NPC263753
0.8131	Intermediate Similarity	NPC192032
0.8131	Intermediate Similarity	NPC11280
0.8131	Intermediate Similarity	NPC147310
0.8131	Intermediate Similarity	NPC12221
0.8131	Intermediate Similarity	NPC137415
0.8131	Intermediate Similarity	NPC24407
0.8131	Intermediate Similarity	NPC294186
0.8131	Intermediate Similarity	NPC72947
0.8131	Intermediate Similarity	NPC166313
0.8131	Intermediate Similarity	NPC284011
0.8125	Intermediate Similarity	NPC176279
0.8125	Intermediate Similarity	NPC322753
0.8125	Intermediate Similarity	NPC275627
0.8125	Intermediate Similarity	NPC260323
0.812	Intermediate Similarity	NPC99734
0.8108	Intermediate Similarity	NPC58865
0.8103	Intermediate Similarity	NPC154030
0.8103	Intermediate Similarity	NPC471671
0.81	Intermediate Similarity	NPC155393
0.8095	Intermediate Similarity	NPC202986
0.8091	Intermediate Similarity	NPC151477
0.8091	Intermediate Similarity	NPC474352
0.8087	Intermediate Similarity	NPC471668
0.8087	Intermediate Similarity	NPC137496
0.8087	Intermediate Similarity	NPC247858
0.8087	Intermediate Similarity	NPC257540
0.8087	Intermediate Similarity	NPC154511
0.8087	Intermediate Similarity	NPC474387
0.8087	Intermediate Similarity	NPC474358
0.8077	Intermediate Similarity	NPC76938
0.8073	Intermediate Similarity	NPC99557
0.8073	Intermediate Similarity	NPC219286
0.807	Intermediate Similarity	NPC195922
0.807	Intermediate Similarity	NPC249270
0.8058	Intermediate Similarity	NPC304541
0.8058	Intermediate Similarity	NPC270547
0.8053	Intermediate Similarity	NPC46940
0.8053	Intermediate Similarity	NPC302371
0.8049	Intermediate Similarity	NPC266868
0.8039	Intermediate Similarity	NPC123273
0.8039	Intermediate Similarity	NPC242240
0.8039	Intermediate Similarity	NPC318325
0.8036	Intermediate Similarity	NPC141782
0.8036	Intermediate Similarity	NPC132720
0.8036	Intermediate Similarity	NPC13482
0.8034	Intermediate Similarity	NPC471449
0.8034	Intermediate Similarity	NPC469644
0.8019	Intermediate Similarity	NPC156313
0.8018	Intermediate Similarity	NPC95344
0.8017	Intermediate Similarity	NPC252962
0.8017	Intermediate Similarity	NPC477136
0.8	Intermediate Similarity	NPC286904
0.8	Intermediate Similarity	NPC32714
0.8	Intermediate Similarity	NPC232165
0.8	Intermediate Similarity	NPC8392
0.8	Intermediate Similarity	NPC274678
0.8	Intermediate Similarity	NPC474211
0.8	Intermediate Similarity	NPC243166
0.8	Intermediate Similarity	NPC35797
0.8	Intermediate Similarity	NPC192948
0.8	Intermediate Similarity	NPC150837
0.7982	Intermediate Similarity	NPC254965
0.7982	Intermediate Similarity	NPC241891
0.7982	Intermediate Similarity	NPC327811
0.7982	Intermediate Similarity	NPC261343
0.7981	Intermediate Similarity	NPC271440
0.7965	Intermediate Similarity	NPC4493
0.7965	Intermediate Similarity	NPC95716

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 NPC306295 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	999
0.2-0.3	1351
0.3-0.4	3014
0.4-0.5	2035
0.5-0.6	1161
0.6-0.7	276
0.7-0.8	42
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.89	High Similarity	NPD844	Approved
0.8812	High Similarity	NPD288	Approved
0.8738	High Similarity	NPD289	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD4750	Phase 3
0.8431	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8173	Intermediate Similarity	NPD1809	Phase 2
0.8155	Intermediate Similarity	NPD845	Approved
0.8131	Intermediate Similarity	NPD846	Approved
0.8131	Intermediate Similarity	NPD940	Approved
0.812	Intermediate Similarity	NPD4059	Approved
0.7949	Intermediate Similarity	NPD3091	Approved
0.7944	Intermediate Similarity	NPD3020	Approved
0.7895	Intermediate Similarity	NPD7635	Approved
0.7833	Intermediate Similarity	NPD3092	Approved
0.783	Intermediate Similarity	NPD2859	Approved
0.783	Intermediate Similarity	NPD2860	Approved
0.7787	Intermediate Similarity	NPD6696	Suspended
0.7768	Intermediate Similarity	NPD2342	Discontinued
0.7736	Intermediate Similarity	NPD2934	Approved
0.7736	Intermediate Similarity	NPD2933	Approved
0.7679	Intermediate Similarity	NPD1444	Approved
0.7679	Intermediate Similarity	NPD1445	Approved
0.7667	Intermediate Similarity	NPD3019	Approved
0.7667	Intermediate Similarity	NPD2932	Approved
0.7632	Intermediate Similarity	NPD3022	Approved
0.7632	Intermediate Similarity	NPD3021	Approved
0.7581	Intermediate Similarity	NPD3094	Phase 2
0.7561	Intermediate Similarity	NPD4749	Approved
0.7549	Intermediate Similarity	NPD111	Approved
0.7545	Intermediate Similarity	NPD1242	Phase 1
0.7542	Intermediate Similarity	NPD6671	Approved
0.7521	Intermediate Similarity	NPD3095	Discontinued
0.7478	Intermediate Similarity	NPD1792	Phase 2
0.7458	Intermediate Similarity	NPD1793	Approved
0.7458	Intermediate Similarity	NPD1791	Approved
0.7422	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4624	Approved
0.735	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4625	Phase 3
0.7323	Intermediate Similarity	NPD5736	Approved
0.7258	Intermediate Similarity	NPD1201	Approved
0.7236	Intermediate Similarity	NPD1778	Approved
0.7236	Intermediate Similarity	NPD4626	Approved
0.7236	Intermediate Similarity	NPD1751	Approved
0.7227	Intermediate Similarity	NPD2229	Approved
0.7227	Intermediate Similarity	NPD2228	Approved
0.7227	Intermediate Similarity	NPD2234	Approved
0.7227	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2861	Phase 2
0.7167	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD497	Approved
0.7165	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD9500	Approved
0.7099	Intermediate Similarity	NPD6663	Approved
0.7097	Intermediate Similarity	NPD4589	Approved
0.7083	Intermediate Similarity	NPD495	Approved
0.7083	Intermediate Similarity	NPD1398	Phase 1
0.7083	Intermediate Similarity	NPD498	Approved
0.7083	Intermediate Similarity	NPD496	Approved
0.7073	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD228	Approved
0.7054	Intermediate Similarity	NPD9273	Approved
0.7049	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD3026	Approved
0.704	Intermediate Similarity	NPD3023	Approved
0.7037	Intermediate Similarity	NPD6099	Approved
0.7037	Intermediate Similarity	NPD6100	Approved
0.7031	Intermediate Similarity	NPD1470	Approved
0.7016	Intermediate Similarity	NPD3024	Approved
0.7016	Intermediate Similarity	NPD3025	Approved
0.7016	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1755	Approved
0.7008	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2286	Discontinued
0.694	Remote Similarity	NPD6353	Approved
0.694	Remote Similarity	NPD4097	Suspended
0.6935	Remote Similarity	NPD7330	Discontinued
0.6929	Remote Similarity	NPD2233	Approved
0.6929	Remote Similarity	NPD2232	Approved
0.6929	Remote Similarity	NPD2230	Approved
0.6917	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3620	Phase 2
0.6911	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7340	Approved
0.6905	Remote Similarity	NPD3143	Discontinued
0.6897	Remote Similarity	NPD9608	Approved
0.6897	Remote Similarity	NPD9610	Approved
0.6891	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD9614	Approved
0.6885	Remote Similarity	NPD9618	Approved
0.688	Remote Similarity	NPD5691	Approved
0.688	Remote Similarity	NPD4093	Discontinued
0.688	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5327	Phase 3
0.6866	Remote Similarity	NPD5735	Approved
0.6861	Remote Similarity	NPD5762	Approved
0.6861	Remote Similarity	NPD5763	Approved
0.686	Remote Similarity	NPD9379	Approved
0.686	Remote Similarity	NPD9377	Approved
0.685	Remote Similarity	NPD1610	Phase 2
0.6846	Remote Similarity	NPD2195	Approved
0.6846	Remote Similarity	NPD2194	Approved
0.6838	Remote Similarity	NPD7742	Approved
0.6838	Remote Similarity	NPD7743	Approved
0.6835	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD709	Approved
0.6829	Remote Similarity	NPD7157	Approved
0.68	Remote Similarity	NPD7741	Discontinued
0.68	Remote Similarity	NPD9087	Approved
0.68	Remote Similarity	NPD5303	Approved
0.68	Remote Similarity	NPD5304	Approved
0.6797	Remote Similarity	NPD3070	Discontinued
0.6794	Remote Similarity	NPD3637	Approved
0.6794	Remote Similarity	NPD3636	Approved
0.6794	Remote Similarity	NPD3635	Approved
0.6791	Remote Similarity	NPD4140	Approved
0.6783	Remote Similarity	NPD3028	Approved
0.6783	Remote Similarity	NPD1616	Discontinued
0.6774	Remote Similarity	NPD7636	Approved
0.6772	Remote Similarity	NPD3496	Discontinued
0.6772	Remote Similarity	NPD1981	Approved
0.6772	Remote Similarity	NPD1983	Approved
0.6772	Remote Similarity	NPD1980	Approved
0.6762	Remote Similarity	NPD9089	Approved
0.6746	Remote Similarity	NPD1357	Approved
0.6742	Remote Similarity	NPD2606	Approved
0.6742	Remote Similarity	NPD4908	Phase 1
0.6742	Remote Similarity	NPD2605	Approved
0.6739	Remote Similarity	NPD4726	Approved
0.6739	Remote Similarity	NPD4721	Approved
0.6739	Remote Similarity	NPD4725	Approved
0.6723	Remote Similarity	NPD290	Approved
0.672	Remote Similarity	NPD9616	Approved
0.672	Remote Similarity	NPD9613	Approved
0.672	Remote Similarity	NPD16	Approved
0.672	Remote Similarity	NPD9615	Approved
0.672	Remote Similarity	NPD856	Approved
0.6699	Remote Similarity	NPD9088	Approved
0.6693	Remote Similarity	NPD9381	Approved
0.6693	Remote Similarity	NPD9384	Approved
0.6693	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5155	Approved
0.6692	Remote Similarity	NPD5156	Approved
0.6667	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD1712	Approved
0.6667	Remote Similarity	NPD1548	Phase 1
0.6667	Remote Similarity	NPD2238	Phase 2
0.6667	Remote Similarity	NPD5283	Phase 1
0.6667	Remote Similarity	NPD9093	Approved
0.6667	Remote Similarity	NPD2684	Approved
0.6667	Remote Similarity	NPD316	Approved
0.6643	Remote Similarity	NPD3638	Discontinued
0.6643	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD1134	Approved
0.6641	Remote Similarity	NPD4103	Phase 2
0.6641	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD1131	Approved
0.6641	Remote Similarity	NPD1133	Approved
0.6641	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD1135	Approved
0.6641	Remote Similarity	NPD1129	Approved
0.6639	Remote Similarity	NPD968	Approved
0.6637	Remote Similarity	NPD1693	Approved
0.6617	Remote Similarity	NPD3594	Approved
0.6617	Remote Similarity	NPD3595	Approved
0.6617	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD9622	Approved
0.6614	Remote Similarity	NPD1651	Approved
0.6613	Remote Similarity	NPD475	Phase 2
0.6607	Remote Similarity	NPD1088	Approved
0.6602	Remote Similarity	NPD9294	Approved
0.6594	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD1611	Approved
0.6589	Remote Similarity	NPD422	Phase 1
0.6587	Remote Similarity	NPD318	Approved
0.6587	Remote Similarity	NPD317	Approved
0.6585	Remote Similarity	NPD1138	Approved
0.6583	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2157	Approved
0.6567	Remote Similarity	NPD7095	Approved
0.6567	Remote Similarity	NPD3027	Phase 3
0.6565	Remote Similarity	NPD1283	Approved
0.6565	Remote Similarity	NPD8651	Approved
0.6562	Remote Similarity	NPD2668	Approved
0.6562	Remote Similarity	NPD2667	Approved
0.656	Remote Similarity	NPD256	Approved
0.656	Remote Similarity	NPD255	Approved
0.6549	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD5404	Approved
0.6547	Remote Similarity	NPD5406	Approved
0.6547	Remote Similarity	NPD5405	Approved
0.6547	Remote Similarity	NPD5408	Approved
0.6545	Remote Similarity	NPD1101	Approved
0.6544	Remote Similarity	NPD6346	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