NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.18
Volume:	292.51
LogP:	4.914
LogD:	4.868
LogS:	-5.217
# Rotatable Bonds:	4
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.757
Synthetic Accessibility Score:	2.857
Fsp3:	0.588
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.532
MDCK Permeability:	2.486259472789243e-05
Pgp-inhibitor:	0.097
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.855
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	98.29270935058594%
Volume Distribution (VD):	1.627
Pgp-substrate:	1.843159794807434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.336
CYP1A2-substrate:	0.335
CYP2C19-inhibitor:	0.723
CYP2C19-substrate:	0.205
CYP2C9-inhibitor:	0.635
CYP2C9-substrate:	0.709
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.334
CYP3A4-substrate:	0.336

ADMET: Excretion

Clearance (CL):	8.694
Half-life (T1/2):	0.332

ADMET: Toxicity

hERG Blockers:	0.17
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.763
Carcinogencity:	0.354
Eye Corrosion:	0.138
Eye Irritation:	0.956
Respiratory Toxicity:	0.258

Download Data

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

Natural Product: NPC128368

Natural Product ID:	NPC128368
*Common Name:**	Menthyl Benzoate
IUPAC Name:	[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] benzoate
Synonyms:
Standard InCHIKey:	TTYVYRHNIVBWCB-VNQPRFMTSA-N
Standard InCHI:	InChI=1S/C17H24O2/c1-12(2)15-10-9-13(3)11-16(15)19-17(18)14-7-5-4-6-8-14/h4-8,12-13,15-16H,9-11H2,1-3H3/t13-,15+,16-/m1/s1
SMILES:	C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)c1ccccc1)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3039111
PubChem CID:	170088
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	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
Others	8

Activity Type	# Activity
Individual Protein	2
Organism	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		LogP	=	4.82	n.a.	PMID[504219]
NPT21	Organism	Aspergillus niger	Aspergillus niger	-logMIC	=	1.92	n.a.	PMID[504219]
NPT20	Organism	Candida albicans	Candida albicans	-logMIC	=	1.92	n.a.	PMID[504219]
NPT19	Organism	Escherichia coli	Escherichia coli	-logMIC	=	2.01	n.a.	PMID[504219]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	-logMIC	=	2.01	n.a.	PMID[504219]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	-logMIC	=	1.92	n.a.	PMID[504219]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	100.91	%	PMID[504220]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	101.05	%	PMID[504220]

☑ 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 NPC128368 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	235
0.1-0.2	1154
0.2-0.3	2156
0.3-0.4	5873
0.4-0.5	12188
0.5-0.6	11621
0.6-0.7	8214
0.7-0.8	1162
0.8-0.85	75
0.85-0.9	18
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC473243
0.8889	High Similarity	NPC469636
0.8846	High Similarity	NPC146351
0.8829	High Similarity	NPC307651
0.8774	High Similarity	NPC474365
0.8774	High Similarity	NPC301943
0.8762	High Similarity	NPC42211
0.8762	High Similarity	NPC70624
0.875	High Similarity	NPC78701
0.875	High Similarity	NPC225060
0.875	High Similarity	NPC35448
0.8739	High Similarity	NPC473220
0.8739	High Similarity	NPC470753
0.8727	High Similarity	NPC474157
0.8716	High Similarity	NPC265407
0.8716	High Similarity	NPC83628
0.8667	High Similarity	NPC118343
0.8667	High Similarity	NPC325497
0.8655	High Similarity	NPC470765
0.8655	High Similarity	NPC275576
0.8654	High Similarity	NPC276775
0.8654	High Similarity	NPC92754
0.8654	High Similarity	NPC249912
0.8649	High Similarity	NPC270699
0.8649	High Similarity	NPC82899
0.8636	High Similarity	NPC196246
0.8636	High Similarity	NPC214067
0.8611	High Similarity	NPC269457
0.8584	High Similarity	NPC210092
0.8583	High Similarity	NPC169913
0.8559	High Similarity	NPC305912
0.8559	High Similarity	NPC210089
0.8559	High Similarity	NPC1082
0.8547	High Similarity	NPC50872
0.8545	High Similarity	NPC10251
0.8545	High Similarity	NPC17417
0.8525	High Similarity	NPC147561
0.8505	High Similarity	NPC188895
0.8491	Intermediate Similarity	NPC203925
0.8468	Intermediate Similarity	NPC251854
0.8468	Intermediate Similarity	NPC93084
0.8462	Intermediate Similarity	NPC130398
0.8455	Intermediate Similarity	NPC470278
0.8455	Intermediate Similarity	NPC56493
0.844	Intermediate Similarity	NPC209632
0.8421	Intermediate Similarity	NPC474095
0.8407	Intermediate Similarity	NPC272524
0.8393	Intermediate Similarity	NPC476003
0.8378	Intermediate Similarity	NPC474364
0.8364	Intermediate Similarity	NPC119271
0.8349	Intermediate Similarity	NPC114594
0.8348	Intermediate Similarity	NPC149691
0.8333	Intermediate Similarity	NPC153053
0.8333	Intermediate Similarity	NPC308744
0.832	Intermediate Similarity	NPC472656
0.8319	Intermediate Similarity	NPC158282
0.8319	Intermediate Similarity	NPC79496
0.8306	Intermediate Similarity	NPC72915
0.8304	Intermediate Similarity	NPC174099
0.8261	Intermediate Similarity	NPC474685
0.8261	Intermediate Similarity	NPC186933
0.8257	Intermediate Similarity	NPC89886
0.8257	Intermediate Similarity	NPC60679
0.8254	Intermediate Similarity	NPC474608
0.8254	Intermediate Similarity	NPC126516
0.8254	Intermediate Similarity	NPC203486
0.8254	Intermediate Similarity	NPC48929
0.8254	Intermediate Similarity	NPC329913
0.824	Intermediate Similarity	NPC238370
0.824	Intermediate Similarity	NPC472394
0.823	Intermediate Similarity	NPC167504
0.8226	Intermediate Similarity	NPC473247
0.8214	Intermediate Similarity	NPC99846
0.8214	Intermediate Similarity	NPC269023
0.8205	Intermediate Similarity	NPC152812
0.8198	Intermediate Similarity	NPC30594
0.8198	Intermediate Similarity	NPC37622
0.8197	Intermediate Similarity	NPC476599
0.8189	Intermediate Similarity	NPC473399
0.8189	Intermediate Similarity	NPC195647
0.8189	Intermediate Similarity	NPC291638
0.8189	Intermediate Similarity	NPC66761
0.8189	Intermediate Similarity	NPC472577
0.8189	Intermediate Similarity	NPC473216
0.8189	Intermediate Similarity	NPC17877
0.8182	Intermediate Similarity	NPC31786
0.8174	Intermediate Similarity	NPC477411
0.8165	Intermediate Similarity	NPC304873
0.8158	Intermediate Similarity	NPC321852
0.8131	Intermediate Similarity	NPC270654
0.813	Intermediate Similarity	NPC51292
0.8125	Intermediate Similarity	NPC472551
0.8125	Intermediate Similarity	NPC472372
0.8125	Intermediate Similarity	NPC472545
0.8125	Intermediate Similarity	NPC472374
0.8115	Intermediate Similarity	NPC295664
0.8115	Intermediate Similarity	NPC125053
0.811	Intermediate Similarity	NPC472591
0.8108	Intermediate Similarity	NPC105899
0.8099	Intermediate Similarity	NPC472703
0.8087	Intermediate Similarity	NPC161611
0.8083	Intermediate Similarity	NPC144547
0.807	Intermediate Similarity	NPC260818
0.8062	Intermediate Similarity	NPC283375
0.8062	Intermediate Similarity	NPC183122
0.8062	Intermediate Similarity	NPC39549
0.8062	Intermediate Similarity	NPC475373
0.8051	Intermediate Similarity	NPC45794
0.8051	Intermediate Similarity	NPC228318
0.8051	Intermediate Similarity	NPC469574
0.8047	Intermediate Similarity	NPC477893
0.8047	Intermediate Similarity	NPC477896
0.8034	Intermediate Similarity	NPC135730
0.8034	Intermediate Similarity	NPC100353
0.8034	Intermediate Similarity	NPC226093
0.8033	Intermediate Similarity	NPC472704
0.8017	Intermediate Similarity	NPC196075
0.8017	Intermediate Similarity	NPC474363
0.8016	Intermediate Similarity	NPC475478
0.8	Intermediate Similarity	NPC475652
0.8	Intermediate Similarity	NPC119631
0.8	Intermediate Similarity	NPC238861
0.8	Intermediate Similarity	NPC988
0.8	Intermediate Similarity	NPC45613
0.8	Intermediate Similarity	NPC289432
0.8	Intermediate Similarity	NPC77000
0.8	Intermediate Similarity	NPC66208
0.8	Intermediate Similarity	NPC214550
0.8	Intermediate Similarity	NPC232958
0.8	Intermediate Similarity	NPC25458
0.8	Intermediate Similarity	NPC210591
0.7984	Intermediate Similarity	NPC472706
0.7982	Intermediate Similarity	NPC217621
0.7981	Intermediate Similarity	NPC220893
0.7981	Intermediate Similarity	NPC173443
0.7965	Intermediate Similarity	NPC211439
0.7949	Intermediate Similarity	NPC221275
0.7949	Intermediate Similarity	NPC228936
0.7949	Intermediate Similarity	NPC306740
0.7939	Intermediate Similarity	NPC183270
0.7939	Intermediate Similarity	NPC48017
0.7939	Intermediate Similarity	NPC473085
0.7939	Intermediate Similarity	NPC184747
0.7939	Intermediate Similarity	NPC472547
0.7939	Intermediate Similarity	NPC147880
0.7939	Intermediate Similarity	NPC477904
0.7939	Intermediate Similarity	NPC473112
0.7939	Intermediate Similarity	NPC473758
0.7939	Intermediate Similarity	NPC473060
0.7939	Intermediate Similarity	NPC473109
0.7939	Intermediate Similarity	NPC211137
0.7939	Intermediate Similarity	NPC473081
0.7939	Intermediate Similarity	NPC97667
0.7939	Intermediate Similarity	NPC473613
0.7939	Intermediate Similarity	NPC100913
0.7939	Intermediate Similarity	NPC275592
0.7939	Intermediate Similarity	NPC4341
0.7939	Intermediate Similarity	NPC476094
0.7939	Intermediate Similarity	NPC43241
0.7939	Intermediate Similarity	NPC200592
0.7939	Intermediate Similarity	NPC90614
0.7939	Intermediate Similarity	NPC171207
0.7931	Intermediate Similarity	NPC474176
0.7928	Intermediate Similarity	NPC234305
0.7928	Intermediate Similarity	NPC255676
0.7928	Intermediate Similarity	NPC329556
0.7925	Intermediate Similarity	NPC77273
0.792	Intermediate Similarity	NPC472707
0.7917	Intermediate Similarity	NPC204784
0.7909	Intermediate Similarity	NPC473325
0.7905	Intermediate Similarity	NPC213156
0.7905	Intermediate Similarity	NPC240108
0.7899	Intermediate Similarity	NPC45104
0.7895	Intermediate Similarity	NPC85493
0.7886	Intermediate Similarity	NPC140118
0.7886	Intermediate Similarity	NPC12881
0.7885	Intermediate Similarity	NPC304760
0.7879	Intermediate Similarity	NPC27377
0.7879	Intermediate Similarity	NPC472576
0.7879	Intermediate Similarity	NPC87448
0.7879	Intermediate Similarity	NPC16912
0.7879	Intermediate Similarity	NPC97947
0.7879	Intermediate Similarity	NPC291599
0.7879	Intermediate Similarity	NPC118080
0.7879	Intermediate Similarity	NPC41481
0.7879	Intermediate Similarity	NPC224491
0.7874	Intermediate Similarity	NPC469519
0.7863	Intermediate Similarity	NPC472395
0.7863	Intermediate Similarity	NPC472371
0.7863	Intermediate Similarity	NPC9905
0.7857	Intermediate Similarity	NPC85977
0.785	Intermediate Similarity	NPC261181
0.7845	Intermediate Similarity	NPC474314
0.7845	Intermediate Similarity	NPC212415
0.7829	Intermediate Similarity	NPC153617
0.7826	Intermediate Similarity	NPC273837
0.7823	Intermediate Similarity	NPC246166
0.782	Intermediate Similarity	NPC472546
0.782	Intermediate Similarity	NPC34012
0.7818	Intermediate Similarity	NPC472318

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 NPC128368 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	859
0.2-0.3	1069
0.3-0.4	2449
0.4-0.5	2564
0.5-0.6	1394
0.6-0.7	497
0.7-0.8	95
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
0.8899	High Similarity	NPD2181	Clinical (unspecified phase)
0.8667	High Similarity	NPD1238	Approved
0.8545	High Similarity	NPD2182	Approved
0.8182	Intermediate Similarity	NPD164	Approved
0.8167	Intermediate Similarity	NPD6287	Discontinued
0.8037	Intermediate Similarity	NPD1989	Approved
0.8	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD2066	Phase 3
0.7949	Intermediate Similarity	NPD2629	Approved
0.7937	Intermediate Similarity	NPD7008	Discontinued
0.7937	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD1930	Approved
0.7928	Intermediate Similarity	NPD1929	Approved
0.7857	Intermediate Similarity	NPD5909	Discontinued
0.785	Intermediate Similarity	NPD1202	Approved
0.7845	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD5951	Approved
0.7699	Intermediate Similarity	NPD1237	Approved
0.7692	Intermediate Similarity	NPD9259	Approved
0.7692	Intermediate Similarity	NPD9257	Approved
0.768	Intermediate Similarity	NPD2199	Approved
0.768	Intermediate Similarity	NPD2198	Approved
0.7672	Intermediate Similarity	NPD2067	Discontinued
0.7647	Intermediate Similarity	NPD7236	Approved
0.7619	Intermediate Similarity	NPD1087	Approved
0.7586	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6832	Phase 2
0.757	Intermediate Similarity	NPD3673	Approved
0.757	Intermediate Similarity	NPD3672	Approved
0.7559	Intermediate Similarity	NPD2798	Approved
0.7559	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD1932	Approved
0.752	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD7094	Approved
0.7479	Intermediate Similarity	NPD6858	Approved
0.7456	Intermediate Similarity	NPD6647	Phase 2
0.744	Intermediate Similarity	NPD1281	Approved
0.744	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4198	Discontinued
0.7436	Intermediate Similarity	NPD2329	Discontinued
0.7419	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD17	Approved
0.7411	Intermediate Similarity	NPD5926	Approved
0.7407	Intermediate Similarity	NPD1086	Approved
0.7407	Intermediate Similarity	NPD1090	Approved
0.7407	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD9256	Approved
0.7407	Intermediate Similarity	NPD1089	Approved
0.7407	Intermediate Similarity	NPD9258	Approved
0.7405	Intermediate Similarity	NPD7713	Phase 3
0.7402	Intermediate Similarity	NPD1876	Approved
0.7402	Intermediate Similarity	NPD5667	Approved
0.7398	Intermediate Similarity	NPD9545	Approved
0.7388	Intermediate Similarity	NPD2799	Discontinued
0.7385	Intermediate Similarity	NPD6039	Approved
0.7377	Intermediate Similarity	NPD9493	Approved
0.7376	Intermediate Similarity	NPD7239	Suspended
0.7373	Intermediate Similarity	NPD5240	Approved
0.7373	Intermediate Similarity	NPD5236	Approved
0.7373	Intermediate Similarity	NPD5239	Approved
0.7373	Intermediate Similarity	NPD5235	Approved
0.7373	Intermediate Similarity	NPD5237	Approved
0.7372	Intermediate Similarity	NPD4628	Phase 3
0.7364	Intermediate Similarity	NPD1563	Approved
0.7364	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6273	Approved
0.7348	Intermediate Similarity	NPD2979	Phase 3
0.7348	Intermediate Similarity	NPD4307	Phase 2
0.7344	Intermediate Similarity	NPD2797	Approved
0.7339	Intermediate Similarity	NPD5691	Approved
0.7339	Intermediate Similarity	NPD5585	Approved
0.7315	Intermediate Similarity	NPD800	Approved
0.7313	Intermediate Similarity	NPD2569	Approved
0.7313	Intermediate Similarity	NPD2567	Approved
0.7311	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1693	Approved
0.7293	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD5306	Approved
0.728	Intermediate Similarity	NPD5305	Approved
0.7279	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD1088	Approved
0.7273	Intermediate Similarity	NPD1241	Discontinued
0.7266	Intermediate Similarity	NPD1283	Approved
0.7265	Intermediate Similarity	NPD3134	Approved
0.7257	Intermediate Similarity	NPD9495	Approved
0.7246	Intermediate Similarity	NPD7003	Approved
0.7244	Intermediate Similarity	NPD1608	Approved
0.7218	Intermediate Similarity	NPD3373	Approved
0.7209	Intermediate Similarity	NPD3267	Approved
0.7209	Intermediate Similarity	NPD3266	Approved
0.7206	Intermediate Similarity	NPD2438	Suspended
0.7206	Intermediate Similarity	NPD2935	Discontinued
0.7203	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2313	Discontinued
0.7197	Intermediate Similarity	NPD3764	Approved
0.7193	Intermediate Similarity	NPD7798	Approved
0.7182	Intermediate Similarity	NPD1239	Approved
0.7168	Intermediate Similarity	NPD1564	Approved
0.7168	Intermediate Similarity	NPD1565	Approved
0.7168	Intermediate Similarity	NPD1566	Phase 3
0.7167	Intermediate Similarity	NPD2201	Approved
0.7165	Intermediate Similarity	NPD4806	Approved
0.7165	Intermediate Similarity	NPD4807	Approved
0.7164	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD9260	Approved
0.7132	Intermediate Similarity	NPD4308	Phase 3
0.713	Intermediate Similarity	NPD1282	Approved
0.7117	Intermediate Similarity	NPD7631	Approved
0.7109	Intermediate Similarity	NPD6637	Approved
0.7097	Intermediate Similarity	NPD4574	Approved
0.7097	Intermediate Similarity	NPD4576	Approved
0.7087	Intermediate Similarity	NPD4135	Approved
0.7087	Intermediate Similarity	NPD4136	Approved
0.7087	Intermediate Similarity	NPD4106	Approved
0.708	Intermediate Similarity	NPD2531	Phase 2
0.708	Intermediate Similarity	NPD2796	Approved
0.7068	Intermediate Similarity	NPD3268	Approved
0.7063	Intermediate Similarity	NPD1651	Approved
0.7054	Intermediate Similarity	NPD4359	Approved
0.705	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD2347	Approved
0.7037	Intermediate Similarity	NPD4622	Approved
0.7037	Intermediate Similarity	NPD4618	Approved
0.7031	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7058	Phase 2
0.7027	Intermediate Similarity	NPD7609	Phase 3
0.7027	Intermediate Similarity	NPD7057	Phase 3
0.7023	Intermediate Similarity	NPD6085	Phase 2
0.7023	Intermediate Similarity	NPD1019	Discontinued
0.7023	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD9490	Approved
0.7018	Intermediate Similarity	NPD3495	Discontinued
0.7015	Intermediate Similarity	NPD6663	Approved
0.7015	Intermediate Similarity	NPD8032	Phase 2
0.7009	Intermediate Similarity	NPD9261	Approved
0.7008	Intermediate Similarity	NPD4626	Approved
0.7007	Intermediate Similarity	NPD3748	Approved
0.7	Intermediate Similarity	NPD8166	Discontinued
0.6991	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1894	Discontinued
0.6983	Remote Similarity	NPD2553	Approved
0.6983	Remote Similarity	NPD2552	Approved
0.6983	Remote Similarity	NPD2549	Approved
0.6983	Remote Similarity	NPD2550	Approved
0.6983	Remote Similarity	NPD2555	Approved
0.6983	Remote Similarity	NPD2558	Approved
0.6977	Remote Similarity	NPD9717	Approved
0.697	Remote Similarity	NPD5736	Approved
0.6966	Remote Similarity	NPD7458	Discontinued
0.6966	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3887	Approved
0.6949	Remote Similarity	NPD3048	Approved
0.6949	Remote Similarity	NPD3046	Approved
0.6949	Remote Similarity	NPD3047	Approved
0.6947	Remote Similarity	NPD1203	Approved
0.6942	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1317	Discontinued
0.694	Remote Similarity	NPD6798	Discontinued
0.6934	Remote Similarity	NPD5688	Approved
0.6934	Remote Similarity	NPD5689	Approved
0.6929	Remote Similarity	NPD4102	Approved
0.6929	Remote Similarity	NPD4105	Approved
0.6923	Remote Similarity	NPD5159	Phase 2
0.6923	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD225	Approved
0.6923	Remote Similarity	NPD227	Approved
0.6923	Remote Similarity	NPD5157	Phase 1
0.6923	Remote Similarity	NPD4188	Approved
0.6923	Remote Similarity	NPD4189	Approved
0.6917	Remote Similarity	NPD1358	Approved
0.6916	Remote Similarity	NPD9491	Approved
0.6912	Remote Similarity	NPD1933	Approved
0.6911	Remote Similarity	NPD5277	Phase 2
0.6906	Remote Similarity	NPD7611	Approved
0.6891	Remote Similarity	NPD5048	Discontinued
0.6889	Remote Similarity	NPD4870	Approved
0.6889	Remote Similarity	NPD7961	Discontinued
0.6887	Remote Similarity	NPD942	Approved
0.688	Remote Similarity	NPD3317	Approved
0.6879	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4110	Phase 3
0.6875	Remote Similarity	NPD1778	Approved
0.6875	Remote Similarity	NPD2345	Approved
0.6866	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2897	Discontinued
0.6855	Remote Similarity	NPD2650	Approved
0.6855	Remote Similarity	NPD2652	Approved
0.6855	Remote Similarity	NPD6010	Discontinued
0.6847	Remote Similarity	NPD5346	Phase 2
0.6847	Remote Similarity	NPD5347	Phase 2
0.6846	Remote Similarity	NPD4878	Approved
0.6842	Remote Similarity	NPD5204	Approved
0.6835	Remote Similarity	NPD4476	Approved
0.6835	Remote Similarity	NPD4477	Approved
0.6835	Remote Similarity	NPD1551	Phase 2

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