NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.15
Volume:	243.208
LogP:	3.863
LogD:	3.673
LogS:	-4.516
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.757
Synthetic Accessibility Score:	3.611
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.684
MDCK Permeability:	2.2546237232745625e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.892
30% Bioavailability (F30%):	0.809

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.234
Plasma Protein Binding (PPB):	96.78898620605469%
Volume Distribution (VD):	2.56
Pgp-substrate:	5.137005805969238%

ADMET: Metabolism

CYP1A2-inhibitor:	0.828
CYP1A2-substrate:	0.913
CYP2C19-inhibitor:	0.775
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.451
CYP2C9-substrate:	0.806
CYP2D6-inhibitor:	0.621
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.796
CYP3A4-substrate:	0.565

ADMET: Excretion

Clearance (CL):	9.456
Half-life (T1/2):	0.281

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.061
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.717
Skin Sensitization:	0.934
Carcinogencity:	0.206
Eye Corrosion:	0.916
Eye Irritation:	0.985
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC64586

Natural Product ID:	NPC64586
*Common Name:**	Cyclolauren-2-Ol
IUPAC Name:	5-[(1S,2R,5R)-1,2-dimethyl-2-bicyclo[3.1.0]hexanyl]-2-methylphenol
Synonyms:	Cyclolauren-2-ol
Standard InCHIKey:	CVIXDDABZMVCMV-SNPRPXQTSA-N
Standard InCHI:	InChI=1S/C15H20O/c1-10-4-5-11(8-13(10)16)14(2)7-6-12-9-15(12,14)3/h4-5,8,12,16H,6-7,9H2,1-3H3/t12-,14+,15+/m1/s1
SMILES:	Cc1ccc(cc1O)[C@]1(C)CC[C@@H]2C[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512942
PubChem CID:	11390308
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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[464335]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[464335]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[464335]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[464335]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[464335]

☑ 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 NPC64586 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	367
0.1-0.2	1874
0.2-0.3	3510
0.3-0.4	12699
0.4-0.5	10546
0.5-0.6	10317
0.6-0.7	2817
0.7-0.8	493
0.8-0.85	62
0.85-0.9	10
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9223	High Similarity	NPC310456
0.92	High Similarity	NPC299762
0.92	High Similarity	NPC33675
0.91	High Similarity	NPC6597
0.91	High Similarity	NPC79241
0.9048	High Similarity	NPC306295
0.902	High Similarity	NPC252105
0.9	High Similarity	NPC312132
0.9	High Similarity	NPC259512
0.8922	High Similarity	NPC72729
0.8818	High Similarity	NPC469719
0.88	High Similarity	NPC152415
0.8762	High Similarity	NPC47284
0.87	High Similarity	NPC55903
0.8679	High Similarity	NPC53740
0.8667	High Similarity	NPC475225
0.8624	High Similarity	NPC322753
0.8614	High Similarity	NPC245187
0.86	High Similarity	NPC306074
0.86	High Similarity	NPC231150
0.8598	High Similarity	NPC320439
0.8585	High Similarity	NPC117115
0.8571	High Similarity	NPC471228
0.8571	High Similarity	NPC235762
0.8545	High Similarity	NPC250323
0.8534	High Similarity	NPC297057
0.8529	High Similarity	NPC222146
0.8505	High Similarity	NPC21594
0.8462	Intermediate Similarity	NPC122005
0.8462	Intermediate Similarity	NPC252821
0.8455	Intermediate Similarity	NPC470770
0.8455	Intermediate Similarity	NPC176279
0.8455	Intermediate Similarity	NPC77772
0.8455	Intermediate Similarity	NPC260323
0.8455	Intermediate Similarity	NPC266937
0.8447	Intermediate Similarity	NPC202986
0.844	Intermediate Similarity	NPC58865
0.8431	Intermediate Similarity	NPC316301
0.8431	Intermediate Similarity	NPC289769
0.8431	Intermediate Similarity	NPC27323
0.8426	Intermediate Similarity	NPC66834
0.8426	Intermediate Similarity	NPC151477
0.8407	Intermediate Similarity	NPC474358
0.8407	Intermediate Similarity	NPC154511
0.8407	Intermediate Similarity	NPC247858
0.8407	Intermediate Similarity	NPC474387
0.8407	Intermediate Similarity	NPC257540
0.8407	Intermediate Similarity	NPC137496
0.8396	Intermediate Similarity	NPC269212
0.8393	Intermediate Similarity	NPC195922
0.8381	Intermediate Similarity	NPC225506
0.8381	Intermediate Similarity	NPC211885
0.8381	Intermediate Similarity	NPC174911
0.8378	Intermediate Similarity	NPC62867
0.8378	Intermediate Similarity	NPC177962
0.8365	Intermediate Similarity	NPC77492
0.8364	Intermediate Similarity	NPC141782
0.8364	Intermediate Similarity	NPC13482
0.8333	Intermediate Similarity	NPC306884
0.8333	Intermediate Similarity	NPC155072
0.8333	Intermediate Similarity	NPC94139
0.8333	Intermediate Similarity	NPC147284
0.8333	Intermediate Similarity	NPC162314
0.8333	Intermediate Similarity	NPC3358
0.8333	Intermediate Similarity	NPC210497
0.8318	Intermediate Similarity	NPC238696
0.8318	Intermediate Similarity	NPC272029
0.8318	Intermediate Similarity	NPC475580
0.8318	Intermediate Similarity	NPC254965
0.8318	Intermediate Similarity	NPC327811
0.8317	Intermediate Similarity	NPC192
0.8302	Intermediate Similarity	NPC477685
0.83	Intermediate Similarity	NPC27974
0.8235	Intermediate Similarity	NPC304541
0.8235	Intermediate Similarity	NPC155908
0.8208	Intermediate Similarity	NPC129373
0.8208	Intermediate Similarity	NPC48730
0.8208	Intermediate Similarity	NPC248396
0.82	Intermediate Similarity	NPC407
0.82	Intermediate Similarity	NPC307235
0.8198	Intermediate Similarity	NPC132720
0.819	Intermediate Similarity	NPC152097
0.819	Intermediate Similarity	NPC156313
0.819	Intermediate Similarity	NPC225464
0.8174	Intermediate Similarity	NPC477136
0.8173	Intermediate Similarity	NPC8392
0.8173	Intermediate Similarity	NPC144682
0.8158	Intermediate Similarity	NPC35797
0.8158	Intermediate Similarity	NPC192948
0.8148	Intermediate Similarity	NPC244513
0.8148	Intermediate Similarity	NPC218879
0.8148	Intermediate Similarity	NPC227458
0.8142	Intermediate Similarity	NPC715
0.8131	Intermediate Similarity	NPC80800
0.8131	Intermediate Similarity	NPC12221
0.8125	Intermediate Similarity	NPC151537
0.8125	Intermediate Similarity	NPC224527
0.8125	Intermediate Similarity	NPC469912
0.812	Intermediate Similarity	NPC68339
0.812	Intermediate Similarity	NPC99734
0.8113	Intermediate Similarity	NPC260775
0.8113	Intermediate Similarity	NPC92730
0.8108	Intermediate Similarity	NPC299568
0.8108	Intermediate Similarity	NPC186385
0.8103	Intermediate Similarity	NPC48342
0.8103	Intermediate Similarity	NPC164649
0.81	Intermediate Similarity	NPC155393
0.8091	Intermediate Similarity	NPC204901
0.8091	Intermediate Similarity	NPC232523
0.8091	Intermediate Similarity	NPC158253
0.8087	Intermediate Similarity	NPC141001
0.8087	Intermediate Similarity	NPC92
0.8087	Intermediate Similarity	NPC471668
0.8087	Intermediate Similarity	NPC219112
0.8087	Intermediate Similarity	NPC469663
0.8087	Intermediate Similarity	NPC308311
0.8087	Intermediate Similarity	NPC38893
0.8087	Intermediate Similarity	NPC477137
0.8077	Intermediate Similarity	NPC76938
0.8073	Intermediate Similarity	NPC37802
0.807	Intermediate Similarity	NPC471534
0.807	Intermediate Similarity	NPC268160
0.8056	Intermediate Similarity	NPC108497
0.8053	Intermediate Similarity	NPC228452
0.8053	Intermediate Similarity	NPC228425
0.8053	Intermediate Similarity	NPC46940
0.8053	Intermediate Similarity	NPC302371
0.8051	Intermediate Similarity	NPC328504
0.8049	Intermediate Similarity	NPC266868
0.8039	Intermediate Similarity	NPC258219
0.8039	Intermediate Similarity	NPC123273
0.8039	Intermediate Similarity	NPC318325
0.8039	Intermediate Similarity	NPC242240
0.8037	Intermediate Similarity	NPC70677
0.8037	Intermediate Similarity	NPC130756
0.8037	Intermediate Similarity	NPC12931
0.8034	Intermediate Similarity	NPC473974
0.8034	Intermediate Similarity	NPC31296
0.8034	Intermediate Similarity	NPC258366
0.8034	Intermediate Similarity	NPC79933
0.8019	Intermediate Similarity	NPC474073
0.8019	Intermediate Similarity	NPC475078
0.8018	Intermediate Similarity	NPC174981
0.8018	Intermediate Similarity	NPC11554
0.8017	Intermediate Similarity	NPC304510
0.8017	Intermediate Similarity	NPC172219
0.8	Intermediate Similarity	NPC286904
0.8	Intermediate Similarity	NPC147179
0.8	Intermediate Similarity	NPC201662
0.8	Intermediate Similarity	NPC246760
0.8	Intermediate Similarity	NPC12640
0.8	Intermediate Similarity	NPC150837
0.8	Intermediate Similarity	NPC477814
0.8	Intermediate Similarity	NPC32714
0.8	Intermediate Similarity	NPC99836
0.8	Intermediate Similarity	NPC84999
0.7982	Intermediate Similarity	NPC120719
0.7981	Intermediate Similarity	NPC271440
0.7981	Intermediate Similarity	NPC29373
0.7966	Intermediate Similarity	NPC318552
0.7966	Intermediate Similarity	NPC190501
0.7965	Intermediate Similarity	NPC54373
0.7965	Intermediate Similarity	NPC95716
0.7965	Intermediate Similarity	NPC275627
0.7949	Intermediate Similarity	NPC154030
0.7949	Intermediate Similarity	NPC471671
0.7949	Intermediate Similarity	NPC206
0.7946	Intermediate Similarity	NPC314187
0.7946	Intermediate Similarity	NPC33728
0.7946	Intermediate Similarity	NPC19808
0.7941	Intermediate Similarity	NPC25493
0.7941	Intermediate Similarity	NPC19680
0.7941	Intermediate Similarity	NPC113460
0.7931	Intermediate Similarity	NPC308828
0.7909	Intermediate Similarity	NPC471350
0.7899	Intermediate Similarity	NPC474175
0.7899	Intermediate Similarity	NPC32322
0.7899	Intermediate Similarity	NPC241001
0.7899	Intermediate Similarity	NPC259703
0.7895	Intermediate Similarity	NPC471179
0.7895	Intermediate Similarity	NPC26615
0.789	Intermediate Similarity	NPC233827
0.789	Intermediate Similarity	NPC168393
0.789	Intermediate Similarity	NPC24327
0.789	Intermediate Similarity	NPC12870
0.7885	Intermediate Similarity	NPC204210
0.7881	Intermediate Similarity	NPC469644
0.7881	Intermediate Similarity	NPC93071
0.7881	Intermediate Similarity	NPC126002
0.7876	Intermediate Similarity	NPC224870
0.7864	Intermediate Similarity	NPC177420
0.7864	Intermediate Similarity	NPC280347
0.7864	Intermediate Similarity	NPC98772
0.7863	Intermediate Similarity	NPC320864
0.7863	Intermediate Similarity	NPC16030
0.785	Intermediate Similarity	NPC32674
0.7843	Intermediate Similarity	NPC23167
0.7843	Intermediate Similarity	NPC184169
0.7838	Intermediate Similarity	NPC271274
0.7838	Intermediate Similarity	NPC469913

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 NPC64586 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	998
0.2-0.3	1402
0.3-0.4	3135
0.4-0.5	2006
0.5-0.6	1042
0.6-0.7	203
0.7-0.8	34
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD288	Approved
0.89	High Similarity	NPD844	Approved
0.8558	High Similarity	NPD289	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD845	Approved
0.8173	Intermediate Similarity	NPD1809	Phase 2
0.812	Intermediate Similarity	NPD4059	Approved
0.8108	Intermediate Similarity	NPD4750	Phase 3
0.8103	Intermediate Similarity	NPD3091	Approved
0.8053	Intermediate Similarity	NPD7635	Approved
0.7966	Intermediate Similarity	NPD2932	Approved
0.7966	Intermediate Similarity	NPD3019	Approved
0.7944	Intermediate Similarity	NPD3020	Approved
0.7928	Intermediate Similarity	NPD2342	Discontinued
0.7838	Intermediate Similarity	NPD1445	Approved
0.7838	Intermediate Similarity	NPD1444	Approved
0.7833	Intermediate Similarity	NPD3092	Approved
0.7788	Intermediate Similarity	NPD1792	Phase 2
0.7667	Intermediate Similarity	NPD3095	Discontinued
0.7664	Intermediate Similarity	NPD2859	Approved
0.7664	Intermediate Similarity	NPD2860	Approved
0.7636	Intermediate Similarity	NPD940	Approved
0.7636	Intermediate Similarity	NPD846	Approved
0.7632	Intermediate Similarity	NPD3022	Approved
0.7632	Intermediate Similarity	NPD3021	Approved
0.7581	Intermediate Similarity	NPD3094	Phase 2
0.757	Intermediate Similarity	NPD2934	Approved
0.757	Intermediate Similarity	NPD2933	Approved
0.7549	Intermediate Similarity	NPD111	Approved
0.7521	Intermediate Similarity	NPD1751	Approved
0.746	Intermediate Similarity	NPD5736	Approved
0.7458	Intermediate Similarity	NPD1793	Approved
0.7458	Intermediate Similarity	NPD1791	Approved
0.7381	Intermediate Similarity	NPD4624	Approved
0.736	Intermediate Similarity	NPD6696	Suspended
0.7317	Intermediate Similarity	NPD3026	Approved
0.7317	Intermediate Similarity	NPD3023	Approved
0.7295	Intermediate Similarity	NPD3024	Approved
0.7295	Intermediate Similarity	NPD3025	Approved
0.725	Intermediate Similarity	NPD6671	Approved
0.7244	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4626	Approved
0.7231	Intermediate Similarity	NPD6663	Approved
0.7213	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD497	Approved
0.7154	Intermediate Similarity	NPD4093	Discontinued
0.7143	Intermediate Similarity	NPD4749	Approved
0.7143	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD2194	Approved
0.7109	Intermediate Similarity	NPD2195	Approved
0.7105	Intermediate Similarity	NPD9500	Approved
0.7097	Intermediate Similarity	NPD4589	Approved
0.7083	Intermediate Similarity	NPD2234	Approved
0.7083	Intermediate Similarity	NPD2228	Approved
0.7083	Intermediate Similarity	NPD498	Approved
0.7083	Intermediate Similarity	NPD2229	Approved
0.7083	Intermediate Similarity	NPD496	Approved
0.7083	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD495	Approved
0.708	Intermediate Similarity	NPD1242	Phase 1
0.7068	Intermediate Similarity	NPD4097	Suspended
0.7054	Intermediate Similarity	NPD3637	Approved
0.7054	Intermediate Similarity	NPD3635	Approved
0.7054	Intermediate Similarity	NPD1712	Approved
0.7054	Intermediate Similarity	NPD2861	Phase 2
0.7054	Intermediate Similarity	NPD3636	Approved
0.7045	Intermediate Similarity	NPD3620	Phase 2
0.7045	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD5327	Phase 3
0.7	Intermediate Similarity	NPD2605	Approved
0.7	Intermediate Similarity	NPD2606	Approved
0.6984	Remote Similarity	NPD1201	Approved
0.6963	Remote Similarity	NPD7742	Approved
0.6963	Remote Similarity	NPD7743	Approved
0.696	Remote Similarity	NPD2286	Discontinued
0.696	Remote Similarity	NPD1778	Approved
0.6957	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5156	Approved
0.6947	Remote Similarity	NPD4625	Phase 3
0.6947	Remote Similarity	NPD5155	Approved
0.6942	Remote Similarity	NPD1398	Phase 1
0.694	Remote Similarity	NPD6353	Approved
0.6935	Remote Similarity	NPD5304	Approved
0.6935	Remote Similarity	NPD5303	Approved
0.6929	Remote Similarity	NPD2233	Approved
0.6929	Remote Similarity	NPD2232	Approved
0.6929	Remote Similarity	NPD2230	Approved
0.6917	Remote Similarity	NPD228	Approved
0.6917	Remote Similarity	NPD4140	Approved
0.6911	Remote Similarity	NPD7340	Approved
0.6911	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD9273	Approved
0.6897	Remote Similarity	NPD9608	Approved
0.6897	Remote Similarity	NPD9610	Approved
0.6885	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5691	Approved
0.688	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1755	Approved
0.687	Remote Similarity	NPD3594	Approved
0.687	Remote Similarity	NPD3595	Approved
0.6866	Remote Similarity	NPD5735	Approved
0.6829	Remote Similarity	NPD709	Approved
0.6815	Remote Similarity	NPD2157	Approved
0.68	Remote Similarity	NPD9087	Approved
0.68	Remote Similarity	NPD7330	Discontinued
0.6788	Remote Similarity	NPD6099	Approved
0.6788	Remote Similarity	NPD6100	Approved
0.6772	Remote Similarity	NPD1981	Approved
0.6772	Remote Similarity	NPD1983	Approved
0.6772	Remote Similarity	NPD3143	Discontinued
0.6772	Remote Similarity	NPD1980	Approved
0.6769	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1470	Approved
0.6763	Remote Similarity	NPD3638	Discontinued
0.6748	Remote Similarity	NPD9614	Approved
0.6748	Remote Similarity	NPD9618	Approved
0.6746	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5762	Approved
0.6739	Remote Similarity	NPD5763	Approved
0.6721	Remote Similarity	NPD9379	Approved
0.6721	Remote Similarity	NPD9377	Approved
0.6694	Remote Similarity	NPD7157	Approved
0.6692	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD5283	Phase 1
0.6667	Remote Similarity	NPD7741	Discontinued
0.6667	Remote Similarity	NPD4717	Approved
0.6667	Remote Similarity	NPD4720	Approved
0.6667	Remote Similarity	NPD4718	Approved
0.6667	Remote Similarity	NPD3070	Discontinued
0.6667	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3496	Discontinued
0.6641	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7636	Approved
0.664	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD3028	Approved
0.6638	Remote Similarity	NPD1616	Discontinued
0.6637	Remote Similarity	NPD1693	Approved
0.6614	Remote Similarity	NPD1651	Approved
0.6614	Remote Similarity	NPD5585	Approved
0.6614	Remote Similarity	NPD1357	Approved
0.6613	Remote Similarity	NPD475	Phase 2
0.6607	Remote Similarity	NPD1088	Approved
0.6602	Remote Similarity	NPD9294	Approved
0.6593	Remote Similarity	NPD8032	Phase 2
0.6589	Remote Similarity	NPD1610	Phase 2
0.6589	Remote Similarity	NPD1611	Approved
0.6587	Remote Similarity	NPD9615	Approved
0.6587	Remote Similarity	NPD9613	Approved
0.6587	Remote Similarity	NPD9616	Approved
0.6585	Remote Similarity	NPD1138	Approved
0.6583	Remote Similarity	NPD290	Approved
0.6549	Remote Similarity	NPD8131	Suspended
0.6545	Remote Similarity	NPD1101	Approved
0.6544	Remote Similarity	NPD6346	Approved
0.6538	Remote Similarity	NPD9088	Approved
0.6535	Remote Similarity	NPD316	Approved
0.6529	Remote Similarity	NPD2684	Approved
0.6525	Remote Similarity	NPD3683	Approved
0.6525	Remote Similarity	NPD2211	Approved
0.6525	Remote Similarity	NPD3681	Approved
0.6525	Remote Similarity	NPD2209	Approved
0.6522	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD1139	Approved
0.6504	Remote Similarity	NPD1137	Approved
0.65	Remote Similarity	NPD968	Approved
0.65	Remote Similarity	NPD4725	Approved
0.65	Remote Similarity	NPD4721	Approved
0.65	Remote Similarity	NPD4726	Approved
0.6493	Remote Similarity	NPD4908	Phase 1
0.6479	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD1281	Approved
0.6454	Remote Similarity	NPD4256	Phase 2
0.6454	Remote Similarity	NPD4257	Approved
0.6441	Remote Similarity	NPD4818	Approved
0.6441	Remote Similarity	NPD4817	Approved
0.6434	Remote Similarity	NPD2668	Approved
0.6434	Remote Similarity	NPD2667	Approved
0.6434	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1086	Approved
0.6429	Remote Similarity	NPD1089	Approved
0.6429	Remote Similarity	NPD256	Approved
0.6429	Remote Similarity	NPD1090	Approved
0.6429	Remote Similarity	NPD255	Approved
0.6423	Remote Similarity	NPD2238	Phase 2
0.6423	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD4212	Discontinued
0.6414	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD3645	Discontinued
0.6412	Remote Similarity	NPD1608	Approved
0.6406	Remote Similarity	NPD1759	Phase 1
0.64	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD4907	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