NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	328.17
Volume:	336.309
LogP:	3.196
LogD:	2.784
LogS:	-4.143
# Rotatable Bonds:	0
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	8
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	6.862
Fsp3:	0.7
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:	-5.294
MDCK Permeability:	5.19E-05
Pgp-inhibitor:	0.655
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.185
30% Bioavailability (F30%):	0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.52
Plasma Protein Binding (PPB):	89.34%
Volume Distribution (VD):	1.481
Pgp-substrate:	4.49%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.256
CYP2C19-inhibitor:	0.54
CYP2C19-substrate:	0.864
CYP2C9-inhibitor:	0.222
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.401
CYP3A4-inhibitor:	0.421
CYP3A4-substrate:	0.546

ADMET: Excretion

Clearance (CL):	11.289
Half-life (T1/2):	0.03

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.828
Drug-inuced Liver Injury (DILI):	0.742
AMES Toxicity:	0.799
Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.431
Carcinogencity:	0.891
Eye Corrosion:	0.462
Eye Irritation:	0.601
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC477575

Natural Product ID:	NPC477575
*Common Name:**	Nepetaparnone
IUPAC Name:	(1R,2S,7S,8S,9R,14R)-3,7,10,14-tetramethyl-16,18-dioxapentacyclo[7.5.2.22,8.01,11.04,8]octadeca-3,10-diene-15,17-dione
Synonyms:	Nepetaparnone
Standard InCHIKey:	KESCUBFFLAUUPO-VUESOCQISA-N
Standard InCHI:	InChI=1S/C20H24O4/c1-9-5-7-13-11(3)16-20-10(2)6-8-14(20)12(4)15(23-18(20)22)19(9,13)17(21)24-16/h9-10,15-16H,5-8H2,1-4H3/t9-,10+,15+,16-,19-,20+
SMILES:	C[C@@H]1CCC2=C([C@@H]3[C@]45[C@H](CCC4=C([C@@H]([C@@]12C(=O)O3)OC5=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	24879156
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO8819	Nepeta parnassica	Species	Lamiaceae	Eukaryota	aerial parts	Mt. Parnassos, Greece	n.a.	PMID[18393463]
NPO8819	Nepeta parnassica	Species	Lamiaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT7173	Organism	Leptothorax	Leptothorax	Activity	=	55	%	PMID[18393463]

☑ 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 NPC477575 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	266
0.1-0.2	1754
0.2-0.3	7742
0.3-0.4	16631
0.4-0.5	9262
0.5-0.6	5956
0.6-0.7	1082
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477576
0.7802	Intermediate Similarity	NPC161638
0.7558	Intermediate Similarity	NPC469620
0.7386	Intermediate Similarity	NPC282293
0.7386	Intermediate Similarity	NPC79277
0.7386	Intermediate Similarity	NPC475481
0.7381	Intermediate Similarity	NPC474551
0.7363	Intermediate Similarity	NPC238593
0.7356	Intermediate Similarity	NPC469690
0.734	Intermediate Similarity	NPC472953
0.7333	Intermediate Similarity	NPC469407
0.7326	Intermediate Similarity	NPC474760
0.732	Intermediate Similarity	NPC2049
0.7312	Intermediate Similarity	NPC212664
0.7292	Intermediate Similarity	NPC469873
0.7292	Intermediate Similarity	NPC33473
0.7273	Intermediate Similarity	NPC6823
0.7273	Intermediate Similarity	NPC472470
0.7262	Intermediate Similarity	NPC238425
0.7262	Intermediate Similarity	NPC472018
0.7262	Intermediate Similarity	NPC474543
0.7253	Intermediate Similarity	NPC78089
0.7234	Intermediate Similarity	NPC469595
0.7234	Intermediate Similarity	NPC212679
0.7234	Intermediate Similarity	NPC220454
0.7234	Intermediate Similarity	NPC469372
0.7229	Intermediate Similarity	NPC69462
0.7222	Intermediate Similarity	NPC475947
0.7222	Intermediate Similarity	NPC222358
0.7222	Intermediate Similarity	NPC193198
0.7222	Intermediate Similarity	NPC215294
0.7209	Intermediate Similarity	NPC152754
0.7209	Intermediate Similarity	NPC59602
0.7209	Intermediate Similarity	NPC476987
0.7204	Intermediate Similarity	NPC477128
0.7204	Intermediate Similarity	NPC226863
0.7204	Intermediate Similarity	NPC80335
0.7191	Intermediate Similarity	NPC471325
0.7188	Intermediate Similarity	NPC470697
0.7184	Intermediate Similarity	NPC220155
0.7174	Intermediate Similarity	NPC261253
0.7174	Intermediate Similarity	NPC220478
0.7174	Intermediate Similarity	NPC107787
0.7174	Intermediate Similarity	NPC474045
0.7172	Intermediate Similarity	NPC474012
0.7172	Intermediate Similarity	NPC476299
0.7159	Intermediate Similarity	NPC182550
0.7159	Intermediate Similarity	NPC178277
0.7159	Intermediate Similarity	NPC471299
0.7159	Intermediate Similarity	NPC150646
0.7158	Intermediate Similarity	NPC472705
0.7158	Intermediate Similarity	NPC150978
0.7158	Intermediate Similarity	NPC70595
0.7158	Intermediate Similarity	NPC123177
0.7158	Intermediate Similarity	NPC472814
0.7158	Intermediate Similarity	NPC74103
0.7158	Intermediate Similarity	NPC284185
0.7158	Intermediate Similarity	NPC290651
0.7158	Intermediate Similarity	NPC177037
0.7143	Intermediate Similarity	NPC110937
0.7143	Intermediate Similarity	NPC100391
0.7143	Intermediate Similarity	NPC474359
0.7143	Intermediate Similarity	NPC475100
0.7128	Intermediate Similarity	NPC280833
0.7128	Intermediate Similarity	NPC288699
0.7126	Intermediate Similarity	NPC316500
0.7111	Intermediate Similarity	NPC35556
0.7111	Intermediate Similarity	NPC200513
0.7108	Intermediate Similarity	NPC107130
0.71	Intermediate Similarity	NPC244456
0.71	Intermediate Similarity	NPC469657
0.7097	Intermediate Similarity	NPC201658
0.7087	Intermediate Similarity	NPC91034
0.7083	Intermediate Similarity	NPC271652
0.7083	Intermediate Similarity	NPC115021
0.7083	Intermediate Similarity	NPC475657
0.7079	Intermediate Similarity	NPC223904
0.7079	Intermediate Similarity	NPC195424
0.7075	Intermediate Similarity	NPC285956
0.7071	Intermediate Similarity	NPC98868
0.7065	Intermediate Similarity	NPC21471
0.7065	Intermediate Similarity	NPC245434
0.7065	Intermediate Similarity	NPC235792
0.7065	Intermediate Similarity	NPC33570
0.7065	Intermediate Similarity	NPC189311
0.7059	Intermediate Similarity	NPC135703
0.7059	Intermediate Similarity	NPC121099
0.7053	Intermediate Similarity	NPC8062
0.7053	Intermediate Similarity	NPC51486
0.7053	Intermediate Similarity	NPC472307
0.7053	Intermediate Similarity	NPC51653
0.7053	Intermediate Similarity	NPC253144
0.7048	Intermediate Similarity	NPC470496
0.7045	Intermediate Similarity	NPC299235
0.7045	Intermediate Similarity	NPC474341
0.7045	Intermediate Similarity	NPC471220
0.7045	Intermediate Similarity	NPC128276
0.7041	Intermediate Similarity	NPC240673
0.7041	Intermediate Similarity	NPC17578
0.7041	Intermediate Similarity	NPC242848
0.7041	Intermediate Similarity	NPC307164
0.7033	Intermediate Similarity	NPC475989
0.7033	Intermediate Similarity	NPC108045
0.7033	Intermediate Similarity	NPC54468
0.7033	Intermediate Similarity	NPC318468
0.7033	Intermediate Similarity	NPC475622
0.7021	Intermediate Similarity	NPC471956
0.7011	Intermediate Similarity	NPC474447
0.7011	Intermediate Similarity	NPC123360
0.701	Intermediate Similarity	NPC471720
0.701	Intermediate Similarity	NPC167219
0.701	Intermediate Similarity	NPC96541
0.701	Intermediate Similarity	NPC53685
0.701	Intermediate Similarity	NPC84893
0.701	Intermediate Similarity	NPC474555
0.7	Intermediate Similarity	NPC25684
0.7	Intermediate Similarity	NPC229584
0.7	Intermediate Similarity	NPC301477
0.7	Intermediate Similarity	NPC141810
0.7	Intermediate Similarity	NPC281949
0.7	Intermediate Similarity	NPC476988
0.7	Intermediate Similarity	NPC14203
0.6989	Remote Similarity	NPC469676
0.6989	Remote Similarity	NPC250981
0.6989	Remote Similarity	NPC470051
0.6989	Remote Similarity	NPC198314
0.6989	Remote Similarity	NPC304558
0.6989	Remote Similarity	NPC470050
0.6979	Remote Similarity	NPC221282
0.6979	Remote Similarity	NPC286341
0.6979	Remote Similarity	NPC191339
0.6979	Remote Similarity	NPC190442
0.6977	Remote Similarity	NPC469641
0.6977	Remote Similarity	NPC476355
0.6977	Remote Similarity	NPC140287
0.6977	Remote Similarity	NPC469643
0.697	Remote Similarity	NPC202705
0.697	Remote Similarity	NPC170143
0.697	Remote Similarity	NPC477949
0.697	Remote Similarity	NPC475709
0.697	Remote Similarity	NPC108475
0.697	Remote Similarity	NPC213947
0.6966	Remote Similarity	NPC268502
0.6966	Remote Similarity	NPC254996
0.6961	Remote Similarity	NPC475526
0.6961	Remote Similarity	NPC473283
0.6961	Remote Similarity	NPC329345
0.6957	Remote Similarity	NPC115786
0.6957	Remote Similarity	NPC159635
0.6957	Remote Similarity	NPC71626
0.6957	Remote Similarity	NPC238197
0.6957	Remote Similarity	NPC149869
0.6957	Remote Similarity	NPC156485
0.6957	Remote Similarity	NPC470918
0.6947	Remote Similarity	NPC474844
0.6947	Remote Similarity	NPC168679
0.6947	Remote Similarity	NPC12872
0.6941	Remote Similarity	NPC129665
0.6941	Remote Similarity	NPC163003
0.6939	Remote Similarity	NPC476487
0.6939	Remote Similarity	NPC476488
0.6939	Remote Similarity	NPC209355
0.6932	Remote Similarity	NPC476028
0.6932	Remote Similarity	NPC141789
0.6932	Remote Similarity	NPC103987
0.6932	Remote Similarity	NPC97516
0.6932	Remote Similarity	NPC187568
0.6932	Remote Similarity	NPC476794
0.6932	Remote Similarity	NPC57744
0.6932	Remote Similarity	NPC476325
0.6932	Remote Similarity	NPC476264
0.6932	Remote Similarity	NPC171204
0.6932	Remote Similarity	NPC470240
0.6932	Remote Similarity	NPC53581
0.6932	Remote Similarity	NPC41780
0.6931	Remote Similarity	NPC477950
0.6931	Remote Similarity	NPC310981
0.6923	Remote Similarity	NPC475936
0.6923	Remote Similarity	NPC475690
0.6923	Remote Similarity	NPC89555
0.6923	Remote Similarity	NPC476958
0.6923	Remote Similarity	NPC173609
0.6923	Remote Similarity	NPC178676
0.6916	Remote Similarity	NPC69291
0.6915	Remote Similarity	NPC24728
0.6915	Remote Similarity	NPC171722
0.6915	Remote Similarity	NPC312561
0.6915	Remote Similarity	NPC167877
0.6915	Remote Similarity	NPC478144
0.6907	Remote Similarity	NPC229976
0.6907	Remote Similarity	NPC60386
0.6907	Remote Similarity	NPC476597
0.6907	Remote Similarity	NPC473273
0.6907	Remote Similarity	NPC473263
0.6907	Remote Similarity	NPC476598
0.6907	Remote Similarity	NPC139692
0.6907	Remote Similarity	NPC473234
0.6907	Remote Similarity	NPC308656
0.69	Remote Similarity	NPC54843
0.69	Remote Similarity	NPC471610

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 NPC477575 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	2447
0.2-0.3	4144
0.3-0.4	1643
0.4-0.5	495
0.5-0.6	157
0.6-0.7	25
0.7-0.8	0
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
0.7111	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5785	Approved
0.6882	Remote Similarity	NPD1694	Approved
0.6848	Remote Similarity	NPD5362	Discontinued
0.6842	Remote Similarity	NPD6903	Approved
0.6804	Remote Similarity	NPD7637	Suspended
0.6768	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4269	Approved
0.6739	Remote Similarity	NPD4270	Approved
0.6739	Remote Similarity	NPD5209	Approved
0.6705	Remote Similarity	NPD8039	Approved
0.6702	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7154	Phase 3
0.6633	Remote Similarity	NPD6411	Approved
0.6632	Remote Similarity	NPD5330	Approved
0.6632	Remote Similarity	NPD6684	Approved
0.6632	Remote Similarity	NPD7521	Approved
0.6632	Remote Similarity	NPD7334	Approved
0.6632	Remote Similarity	NPD7146	Approved
0.6632	Remote Similarity	NPD6409	Approved
0.6632	Remote Similarity	NPD5786	Approved
0.663	Remote Similarity	NPD5369	Approved
0.6606	Remote Similarity	NPD6053	Discontinued
0.6569	Remote Similarity	NPD4225	Approved
0.6566	Remote Similarity	NPD5779	Approved
0.6566	Remote Similarity	NPD5778	Approved
0.6566	Remote Similarity	NPD6399	Phase 3
0.6526	Remote Similarity	NPD5363	Approved
0.6522	Remote Similarity	NPD4252	Approved
0.6522	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7115	Discovery
0.6495	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5737	Approved
0.6495	Remote Similarity	NPD6672	Approved
0.6489	Remote Similarity	NPD5332	Approved
0.6489	Remote Similarity	NPD5331	Approved
0.6465	Remote Similarity	NPD5693	Phase 1
0.6452	Remote Similarity	NPD4790	Discontinued
0.6429	Remote Similarity	NPD6051	Approved
0.6429	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6101	Approved
0.6429	Remote Similarity	NPD1695	Approved
0.6408	Remote Similarity	NPD7638	Approved
0.6383	Remote Similarity	NPD6435	Approved
0.6364	Remote Similarity	NPD6698	Approved
0.6364	Remote Similarity	NPD46	Approved
0.6346	Remote Similarity	NPD7639	Approved
0.6346	Remote Similarity	NPD7640	Approved
0.6344	Remote Similarity	NPD4822	Approved
0.6344	Remote Similarity	NPD4819	Approved
0.6344	Remote Similarity	NPD4821	Approved
0.6344	Remote Similarity	NPD4820	Approved
0.6304	Remote Similarity	NPD4268	Approved
0.6304	Remote Similarity	NPD4271	Approved
0.6296	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4249	Approved
0.6275	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3668	Phase 3
0.6226	Remote Similarity	NPD7632	Discontinued
0.6224	Remote Similarity	NPD4250	Approved
0.6224	Remote Similarity	NPD4251	Approved
0.6211	Remote Similarity	NPD3667	Approved
0.6186	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5282	Discontinued
0.617	Remote Similarity	NPD5368	Approved
0.6154	Remote Similarity	NPD6083	Phase 2
0.6154	Remote Similarity	NPD6084	Phase 2
0.6147	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7983	Approved
0.6126	Remote Similarity	NPD6371	Approved
0.6122	Remote Similarity	NPD6098	Approved
0.6117	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6673	Approved
0.61	Remote Similarity	NPD6904	Approved
0.61	Remote Similarity	NPD6080	Approved
0.6095	Remote Similarity	NPD5696	Approved
0.6091	Remote Similarity	NPD6686	Approved
0.6091	Remote Similarity	NPD7320	Approved
0.6082	Remote Similarity	NPD4786	Approved
0.6058	Remote Similarity	NPD7839	Suspended
0.6055	Remote Similarity	NPD6008	Approved
0.6047	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5207	Approved
0.604	Remote Similarity	NPD5692	Phase 3
0.6036	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5208	Approved
0.6	Remote Similarity	NPD5777	Approved
0.5982	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5694	Approved
0.598	Remote Similarity	NPD8034	Phase 2
0.598	Remote Similarity	NPD6050	Approved
0.598	Remote Similarity	NPD8035	Phase 2
0.5918	Remote Similarity	NPD3665	Phase 1
0.5918	Remote Similarity	NPD3133	Approved
0.5918	Remote Similarity	NPD3666	Approved
0.5909	Remote Similarity	NPD5739	Approved
0.5909	Remote Similarity	NPD7128	Approved
0.5909	Remote Similarity	NPD6402	Approved
0.5909	Remote Similarity	NPD6675	Approved
0.5865	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6001	Approved
0.5865	Remote Similarity	NPD7900	Approved
0.5865	Remote Similarity	NPD7748	Approved
0.5859	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5697	Approved
0.5856	Remote Similarity	NPD5701	Approved
0.5843	Remote Similarity	NPD229	Approved
0.5825	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD6695	Phase 3
0.581	Remote Similarity	NPD5654	Approved
0.5806	Remote Similarity	NPD7319	Approved
0.5804	Remote Similarity	NPD6881	Approved
0.5804	Remote Similarity	NPD6899	Approved
0.58	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.58	Remote Similarity	NPD3618	Phase 1
0.58	Remote Similarity	NPD6422	Discontinued
0.58	Remote Similarity	NPD5279	Phase 3
0.5789	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3617	Approved
0.5784	Remote Similarity	NPD4753	Phase 2
0.5784	Remote Similarity	NPD5370	Suspended
0.5758	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6014	Approved
0.5752	Remote Similarity	NPD6012	Approved
0.5752	Remote Similarity	NPD6373	Approved
0.5752	Remote Similarity	NPD6013	Approved
0.5752	Remote Similarity	NPD6372	Approved
0.575	Remote Similarity	NPD8513	Phase 3
0.5747	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6883	Approved
0.5702	Remote Similarity	NPD7290	Approved
0.5702	Remote Similarity	NPD7102	Approved
0.5701	Remote Similarity	NPD7902	Approved
0.5701	Remote Similarity	NPD5959	Approved
0.5691	Remote Similarity	NPD7507	Approved
0.5673	Remote Similarity	NPD5281	Approved
0.5673	Remote Similarity	NPD7515	Phase 2
0.5673	Remote Similarity	NPD5284	Approved
0.5664	Remote Similarity	NPD6011	Approved
0.5652	Remote Similarity	NPD6869	Approved
0.5652	Remote Similarity	NPD8130	Phase 1
0.5652	Remote Similarity	NPD6847	Approved
0.5652	Remote Similarity	NPD6617	Approved
0.5652	Remote Similarity	NPD6649	Approved
0.5652	Remote Similarity	NPD6650	Approved
0.5647	Remote Similarity	NPD3198	Approved
0.5638	Remote Similarity	NPD3702	Approved
0.5631	Remote Similarity	NPD5328	Approved
0.5625	Remote Similarity	NPD4238	Approved
0.5625	Remote Similarity	NPD4802	Phase 2
0.562	Remote Similarity	NPD8516	Approved
0.562	Remote Similarity	NPD8517	Approved
0.562	Remote Similarity	NPD8515	Approved
0.5612	Remote Similarity	NPD4692	Approved
0.5612	Remote Similarity	NPD4139	Approved
0.5604	Remote Similarity	NPD4137	Phase 3
0.5603	Remote Similarity	NPD8297	Approved
0.5603	Remote Similarity	NPD6882	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