NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.16
Volume:	284.004
LogP:	2.186
LogD:	2.424
LogS:	-2.062
# Rotatable Bonds:	4
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.817
Synthetic Accessibility Score:	4.036
Fsp3:	0.5
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:	-4.786
MDCK Permeability:	1.4722615560458507e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.607
Human Intestinal Absorption (HIA):	0.139
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.764

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.661
Plasma Protein Binding (PPB):	85.73811340332031%
Volume Distribution (VD):	1.127
Pgp-substrate:	11.676361083984375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.526
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.756
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.266
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.255
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	6.92
Half-life (T1/2):	0.579

ADMET: Toxicity

hERG Blockers:	0.138
Human Hepatotoxicity (H-HT):	0.241
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.152
Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.134
Skin Sensitization:	0.542
Carcinogencity:	0.202
Eye Corrosion:	0.052
Eye Irritation:	0.646
Respiratory Toxicity:	0.515

Download Data

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

Natural Product: NPC266343

Natural Product ID:	NPC266343
*Common Name:**	(1R,2S,4S,5S)-2-Methoxy-5-((R)-1-Phenylallyl)Cyclohexane-1,4-Diol
IUPAC Name:	(1R,2S,4S,5S)-2-methoxy-5-[(1R)-1-phenylprop-2-enyl]cyclohexane-1,4-diol
Synonyms:
Standard InCHIKey:	ALWFGDVUNCQWQU-GVRJEKJASA-N
Standard InCHI:	InChI=1S/C16H22O3/c1-3-12(11-7-5-4-6-8-11)13-9-15(18)16(19-2)10-14(13)17/h3-8,12-18H,1,9-10H2,2H3/t12-,13-,14-,15+,16-/m0/s1
SMILES:	C=C[C@@H](c1ccccc1)[C@@H]1C[C@H]([C@H](C[C@@H]1O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451888
PubChem CID:	11380002
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols [CHEMONTID:0002647] Cyclohexanols

*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
NPO29804	Nepalese propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15974608]

☑ 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	1

Activity Type	# Activity
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20763	CELL-LINE	J774.1	Mus musculus	IC50	=	100000.0	nM	PMID[529484]

☑ 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 NPC266343 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	213
0.1-0.2	1006
0.2-0.3	2212
0.3-0.4	7955
0.4-0.5	13766
0.5-0.6	13951
0.6-0.7	3470
0.7-0.8	120
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8318	Intermediate Similarity	NPC111108
0.8095	Intermediate Similarity	NPC474307
0.8087	Intermediate Similarity	NPC473871
0.8087	Intermediate Similarity	NPC473870
0.8019	Intermediate Similarity	NPC25385
0.8019	Intermediate Similarity	NPC475905
0.8019	Intermediate Similarity	NPC193640
0.8	Intermediate Similarity	NPC473889
0.7979	Intermediate Similarity	NPC73637
0.7979	Intermediate Similarity	NPC121478
0.7881	Intermediate Similarity	NPC475933
0.7881	Intermediate Similarity	NPC470158
0.7815	Intermediate Similarity	NPC476971
0.7815	Intermediate Similarity	NPC476972
0.7767	Intermediate Similarity	NPC324602
0.7766	Intermediate Similarity	NPC184030
0.7766	Intermediate Similarity	NPC164449
0.7732	Intermediate Similarity	NPC99482
0.7731	Intermediate Similarity	NPC476970
0.7692	Intermediate Similarity	NPC262826
0.7652	Intermediate Similarity	NPC473860
0.7545	Intermediate Similarity	NPC64642
0.7545	Intermediate Similarity	NPC472982
0.7545	Intermediate Similarity	NPC149455
0.75	Intermediate Similarity	NPC47286
0.75	Intermediate Similarity	NPC471758
0.75	Intermediate Similarity	NPC476976
0.7479	Intermediate Similarity	NPC108286
0.7459	Intermediate Similarity	NPC58061
0.7458	Intermediate Similarity	NPC37641
0.7458	Intermediate Similarity	NPC311175
0.7438	Intermediate Similarity	NPC45821
0.7423	Intermediate Similarity	NPC475199
0.7423	Intermediate Similarity	NPC283012
0.7419	Intermediate Similarity	NPC476977
0.7395	Intermediate Similarity	NPC70973
0.7387	Intermediate Similarity	NPC475282
0.7383	Intermediate Similarity	NPC158623
0.7368	Intermediate Similarity	NPC224544
0.7355	Intermediate Similarity	NPC284022
0.7347	Intermediate Similarity	NPC477770
0.7333	Intermediate Similarity	NPC12016
0.7328	Intermediate Similarity	NPC472862
0.7328	Intermediate Similarity	NPC470820
0.7317	Intermediate Similarity	NPC118533
0.7317	Intermediate Similarity	NPC165045
0.7315	Intermediate Similarity	NPC60373
0.7315	Intermediate Similarity	NPC154905
0.7304	Intermediate Similarity	NPC473137
0.7304	Intermediate Similarity	NPC12656
0.7304	Intermediate Similarity	NPC120280
0.7304	Intermediate Similarity	NPC473869
0.7297	Intermediate Similarity	NPC472979
0.7297	Intermediate Similarity	NPC27252
0.7297	Intermediate Similarity	NPC472980
0.7282	Intermediate Similarity	NPC220596
0.728	Intermediate Similarity	NPC470727
0.7273	Intermediate Similarity	NPC473451
0.7273	Intermediate Similarity	NPC472373
0.7273	Intermediate Similarity	NPC243601
0.7265	Intermediate Similarity	NPC476266
0.7258	Intermediate Similarity	NPC470084
0.7258	Intermediate Similarity	NPC93632
0.725	Intermediate Similarity	NPC475328
0.7248	Intermediate Similarity	NPC469527
0.7236	Intermediate Similarity	NPC206882
0.7227	Intermediate Similarity	NPC223451
0.7222	Intermediate Similarity	NPC474017
0.7222	Intermediate Similarity	NPC80599
0.7213	Intermediate Similarity	NPC114927
0.7213	Intermediate Similarity	NPC473083
0.72	Intermediate Similarity	NPC475710
0.7193	Intermediate Similarity	NPC54373
0.7188	Intermediate Similarity	NPC16485
0.7182	Intermediate Similarity	NPC19136
0.7182	Intermediate Similarity	NPC56168
0.7179	Intermediate Similarity	NPC473556
0.7179	Intermediate Similarity	NPC301651
0.7177	Intermediate Similarity	NPC5428
0.7177	Intermediate Similarity	NPC242032
0.7168	Intermediate Similarity	NPC473524
0.7167	Intermediate Similarity	NPC473439
0.7167	Intermediate Similarity	NPC300827
0.7154	Intermediate Similarity	NPC473111
0.7154	Intermediate Similarity	NPC473082
0.7154	Intermediate Similarity	NPC473110
0.7154	Intermediate Similarity	NPC33654
0.7154	Intermediate Similarity	NPC148627
0.7143	Intermediate Similarity	NPC42300
0.7143	Intermediate Similarity	NPC241522
0.7143	Intermediate Similarity	NPC257582
0.7143	Intermediate Similarity	NPC153739
0.7143	Intermediate Similarity	NPC64201
0.7143	Intermediate Similarity	NPC187998
0.7143	Intermediate Similarity	NPC174495
0.7143	Intermediate Similarity	NPC77040
0.7143	Intermediate Similarity	NPC145305
0.7143	Intermediate Similarity	NPC242807
0.7143	Intermediate Similarity	NPC92164
0.712	Intermediate Similarity	NPC148366
0.712	Intermediate Similarity	NPC311293
0.7119	Intermediate Similarity	NPC471553
0.7119	Intermediate Similarity	NPC320864
0.7119	Intermediate Similarity	NPC84129
0.7117	Intermediate Similarity	NPC37714
0.7117	Intermediate Similarity	NPC152384
0.7115	Intermediate Similarity	NPC187725
0.7115	Intermediate Similarity	NPC141607
0.7105	Intermediate Similarity	NPC30563
0.71	Intermediate Similarity	NPC304538
0.7099	Intermediate Similarity	NPC275592
0.7099	Intermediate Similarity	NPC100913
0.7097	Intermediate Similarity	NPC208302
0.7097	Intermediate Similarity	NPC470724
0.7087	Intermediate Similarity	NPC1793
0.7087	Intermediate Similarity	NPC45715
0.7087	Intermediate Similarity	NPC474356
0.7087	Intermediate Similarity	NPC12275
0.7087	Intermediate Similarity	NPC277804
0.7073	Intermediate Similarity	NPC131747
0.7073	Intermediate Similarity	NPC257682
0.7073	Intermediate Similarity	NPC146355
0.7069	Intermediate Similarity	NPC123175
0.7069	Intermediate Similarity	NPC319803
0.7069	Intermediate Similarity	NPC176730
0.7063	Intermediate Similarity	NPC475875
0.7063	Intermediate Similarity	NPC476968
0.7063	Intermediate Similarity	NPC190144
0.7063	Intermediate Similarity	NPC170844
0.7059	Intermediate Similarity	NPC48781
0.7059	Intermediate Similarity	NPC9592
0.7054	Intermediate Similarity	NPC287745
0.7049	Intermediate Similarity	NPC273336
0.7049	Intermediate Similarity	NPC182333
0.7045	Intermediate Similarity	NPC472576
0.7045	Intermediate Similarity	NPC87448
0.7045	Intermediate Similarity	NPC97947
0.7045	Intermediate Similarity	NPC27377
0.7045	Intermediate Similarity	NPC41481
0.7045	Intermediate Similarity	NPC291599
0.7045	Intermediate Similarity	NPC118080
0.7045	Intermediate Similarity	NPC325078
0.7043	Intermediate Similarity	NPC257430
0.7043	Intermediate Similarity	NPC471189
0.7043	Intermediate Similarity	NPC179002
0.7043	Intermediate Similarity	NPC187583
0.7043	Intermediate Similarity	NPC234376
0.7043	Intermediate Similarity	NPC308689
0.704	Intermediate Similarity	NPC471077
0.704	Intermediate Similarity	NPC295478
0.7034	Intermediate Similarity	NPC148055
0.7031	Intermediate Similarity	NPC6451
0.7031	Intermediate Similarity	NPC230219
0.7027	Intermediate Similarity	NPC323810
0.7018	Intermediate Similarity	NPC62258
0.7018	Intermediate Similarity	NPC55617
0.7018	Intermediate Similarity	NPC474148
0.7018	Intermediate Similarity	NPC276061
0.7008	Intermediate Similarity	NPC143483
0.7008	Intermediate Similarity	NPC192687
0.7008	Intermediate Similarity	NPC224157
0.7	Intermediate Similarity	NPC135961
0.7	Intermediate Similarity	NPC256262
0.6992	Remote Similarity	NPC34012
0.6992	Remote Similarity	NPC77691
0.6992	Remote Similarity	NPC474160
0.6992	Remote Similarity	NPC280704
0.6992	Remote Similarity	NPC471693
0.6992	Remote Similarity	NPC471389
0.6991	Remote Similarity	NPC305603
0.6991	Remote Similarity	NPC61033
0.6984	Remote Similarity	NPC474178
0.6984	Remote Similarity	NPC282703
0.6984	Remote Similarity	NPC184733
0.6984	Remote Similarity	NPC21867
0.6984	Remote Similarity	NPC128208
0.6984	Remote Similarity	NPC129570
0.6984	Remote Similarity	NPC245826
0.6984	Remote Similarity	NPC186843
0.6984	Remote Similarity	NPC98631
0.6984	Remote Similarity	NPC11258
0.6984	Remote Similarity	NPC470213
0.6984	Remote Similarity	NPC252307
0.6984	Remote Similarity	NPC45774
0.6984	Remote Similarity	NPC206615
0.6983	Remote Similarity	NPC228425
0.6983	Remote Similarity	NPC473521
0.6983	Remote Similarity	NPC265002
0.6977	Remote Similarity	NPC158331
0.6977	Remote Similarity	NPC26394
0.6977	Remote Similarity	NPC263064
0.697	Remote Similarity	NPC472547
0.697	Remote Similarity	NPC292882
0.697	Remote Similarity	NPC471388
0.697	Remote Similarity	NPC97667
0.697	Remote Similarity	NPC171207
0.697	Remote Similarity	NPC90614
0.6967	Remote Similarity	NPC469686
0.6967	Remote Similarity	NPC476343
0.6964	Remote Similarity	NPC154899

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 NPC266343 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	746
0.2-0.3	1506
0.3-0.4	3286
0.4-0.5	2109
0.5-0.6	1153
0.6-0.7	148
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7364	Intermediate Similarity	NPD6685	Approved
0.7248	Intermediate Similarity	NPD5765	Approved
0.7227	Intermediate Similarity	NPD5126	Approved
0.7227	Intermediate Similarity	NPD5125	Phase 3
0.7117	Intermediate Similarity	NPD5048	Discontinued
0.7069	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3027	Phase 3
0.7059	Intermediate Similarity	NPD7741	Discontinued
0.7009	Intermediate Similarity	NPD2629	Approved
0.6937	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6912	Phase 3
0.687	Remote Similarity	NPD3022	Approved
0.687	Remote Similarity	NPD3021	Approved
0.6822	Remote Similarity	NPD3719	Approved
0.6822	Remote Similarity	NPD3718	Approved
0.6818	Remote Similarity	NPD3020	Approved
0.681	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4814	Discontinued
0.6746	Remote Similarity	NPD3094	Phase 2
0.6724	Remote Similarity	NPD4750	Phase 3
0.6696	Remote Similarity	NPD4719	Phase 2
0.6694	Remote Similarity	NPD3092	Approved
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD531	Approved
0.6667	Remote Similarity	NPD7798	Approved
0.6642	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2861	Phase 2
0.6641	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD1613	Approved
0.6641	Remote Similarity	NPD2238	Phase 2
0.6637	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6647	Phase 2
0.6555	Remote Similarity	NPD7635	Approved
0.6552	Remote Similarity	NPD6406	Approved
0.6549	Remote Similarity	NPD846	Approved
0.6549	Remote Similarity	NPD940	Approved
0.6545	Remote Similarity	NPD2860	Approved
0.6545	Remote Similarity	NPD2859	Approved
0.6542	Remote Similarity	NPD3672	Approved
0.6542	Remote Similarity	NPD3673	Approved
0.6518	Remote Similarity	NPD2066	Phase 3
0.6515	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1101	Approved
0.6504	Remote Similarity	NPD3091	Approved
0.65	Remote Similarity	NPD5283	Phase 1
0.6496	Remote Similarity	NPD2684	Approved
0.6462	Remote Similarity	NPD4908	Phase 1
0.646	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD2934	Approved
0.6455	Remote Similarity	NPD2933	Approved
0.6449	Remote Similarity	NPD5347	Phase 2
0.6449	Remote Similarity	NPD5346	Phase 2
0.6434	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1610	Phase 2
0.6423	Remote Similarity	NPD7522	Discontinued
0.641	Remote Similarity	NPD290	Approved
0.64	Remote Similarity	NPD9294	Approved
0.64	Remote Similarity	NPD3095	Discontinued
0.6396	Remote Similarity	NPD1989	Approved
0.6393	Remote Similarity	NPD7157	Approved
0.6389	Remote Similarity	NPD1090	Approved
0.6389	Remote Similarity	NPD1089	Approved
0.6389	Remote Similarity	NPD1086	Approved
0.6377	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD845	Approved
0.6364	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7266	Discontinued
0.6348	Remote Similarity	NPD1929	Approved
0.6348	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD1930	Approved
0.6339	Remote Similarity	NPD288	Approved
0.6336	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7876	Discontinued
0.6316	Remote Similarity	NPD1242	Phase 1
0.6316	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD226	Approved
0.6308	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1693	Approved
0.6306	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD1091	Approved
0.6296	Remote Similarity	NPD800	Approved
0.6293	Remote Similarity	NPD5909	Discontinued
0.6286	Remote Similarity	NPD2677	Approved
0.6283	Remote Similarity	NPD9495	Approved
0.6281	Remote Similarity	NPD7843	Approved
0.6279	Remote Similarity	NPD8651	Approved
0.6273	Remote Similarity	NPD752	Approved
0.6273	Remote Similarity	NPD1088	Approved
0.6271	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5305	Approved
0.627	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5306	Approved
0.6269	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD3620	Phase 2
0.6262	Remote Similarity	NPD7524	Approved
0.6262	Remote Similarity	NPD4793	Discontinued
0.6261	Remote Similarity	NPD4818	Approved
0.6261	Remote Similarity	NPD4817	Approved
0.626	Remote Similarity	NPD3317	Approved
0.626	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD6674	Discontinued
0.625	Remote Similarity	NPD844	Approved
0.625	Remote Similarity	NPD4538	Approved
0.625	Remote Similarity	NPD4536	Approved
0.625	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5886	Approved
0.625	Remote Similarity	NPD41	Approved
0.6241	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD5762	Approved
0.6232	Remote Similarity	NPD5763	Approved
0.6232	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5735	Approved
0.6216	Remote Similarity	NPD719	Approved
0.6216	Remote Similarity	NPD720	Approved
0.6216	Remote Similarity	NPD1409	Phase 3
0.6212	Remote Similarity	NPD2613	Approved
0.6202	Remote Similarity	NPD4749	Approved
0.6198	Remote Similarity	NPD228	Approved
0.6195	Remote Similarity	NPD1564	Approved
0.6195	Remote Similarity	NPD1875	Phase 1
0.6195	Remote Similarity	NPD1566	Phase 3
0.6195	Remote Similarity	NPD1565	Approved
0.6194	Remote Similarity	NPD4404	Approved
0.619	Remote Similarity	NPD3971	Phase 1
0.6186	Remote Similarity	NPD5705	Approved
0.6186	Remote Similarity	NPD5704	Approved
0.6186	Remote Similarity	NPD5706	Approved
0.6182	Remote Similarity	NPD1239	Approved
0.6182	Remote Similarity	NPD530	Approved
0.6174	Remote Similarity	NPD2549	Approved
0.6174	Remote Similarity	NPD2558	Approved
0.6174	Remote Similarity	NPD2552	Approved
0.6174	Remote Similarity	NPD2555	Approved
0.6174	Remote Similarity	NPD2553	Approved
0.6174	Remote Similarity	NPD2550	Approved
0.6172	Remote Similarity	NPD4807	Approved
0.6172	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD4806	Approved
0.6172	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6190	Approved
0.6161	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1237	Approved
0.6154	Remote Similarity	NPD3047	Approved
0.6154	Remote Similarity	NPD3048	Approved
0.6154	Remote Similarity	NPD3046	Approved
0.6148	Remote Similarity	NPD7094	Approved
0.6148	Remote Similarity	NPD6858	Approved
0.6148	Remote Similarity	NPD4060	Phase 1
0.6142	Remote Similarity	NPD7725	Approved
0.6142	Remote Similarity	NPD9384	Approved
0.6142	Remote Similarity	NPD5723	Approved
0.6142	Remote Similarity	NPD9381	Approved
0.614	Remote Similarity	NPD5926	Approved
0.6136	Remote Similarity	NPD3018	Phase 2
0.6134	Remote Similarity	NPD9532	Phase 3
0.6129	Remote Similarity	NPD6671	Approved
0.6124	Remote Similarity	NPD2232	Approved
0.6124	Remote Similarity	NPD2233	Approved
0.6124	Remote Similarity	NPD2230	Approved
0.6121	Remote Similarity	NPD1932	Approved
0.6121	Remote Similarity	NPD4189	Approved
0.6121	Remote Similarity	NPD4188	Approved
0.6116	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1087	Approved
0.6111	Remote Similarity	NPD1548	Phase 1
0.6111	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD1809	Phase 2
0.6103	Remote Similarity	NPD6355	Discontinued
0.6098	Remote Similarity	NPD2652	Approved
0.6098	Remote Similarity	NPD2650	Approved
0.6098	Remote Similarity	NPD2234	Approved
0.6098	Remote Similarity	NPD2229	Approved
0.6098	Remote Similarity	NPD2228	Approved
0.6098	Remote Similarity	NPD6010	Discontinued
0.6094	Remote Similarity	NPD4106	Approved
0.6094	Remote Similarity	NPD4135	Approved
0.6094	Remote Similarity	NPD4136	Approved
0.6087	Remote Similarity	NPD5588	Approved
0.6087	Remote Similarity	NPD5960	Phase 3
0.6083	Remote Similarity	NPD2329	Discontinued
0.6081	Remote Similarity	NPD37	Approved
0.6077	Remote Similarity	NPD4659	Approved
0.6077	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD2983	Phase 2
0.6077	Remote Similarity	NPD2982	Phase 2
0.6077	Remote Similarity	NPD9622	Approved
0.6074	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD3089	Approved
0.6074	Remote Similarity	NPD2574	Discontinued
0.6074	Remote Similarity	NPD4746	Phase 3
0.6074	Remote Similarity	NPD3616	Approved
0.6074	Remote Similarity	NPD2566	Approved
0.6074	Remote Similarity	NPD3088	Approved
0.6074	Remote Similarity	NPD3087	Approved
0.6074	Remote Similarity	NPD2570	Approved
0.6074	Remote Similarity	NPD3090	Approved
0.6074	Remote Similarity	NPD2573	Approved
0.6074	Remote Similarity	NPD3614	Approved
0.6074	Remote Similarity	NPD3615	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