NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.14
Volume:	281.368
LogP:	2.1
LogD:	0.89
LogS:	-2.084
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.845
Synthetic Accessibility Score:	4.022
Fsp3:	0.438
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:	-4.567
MDCK Permeability:	2.3430471628671512e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.178
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.98
Plasma Protein Binding (PPB):	82.6939926147461%
Volume Distribution (VD):	1.542
Pgp-substrate:	17.871370315551758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.688
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.327
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.424
CYP3A4-inhibitor:	0.115
CYP3A4-substrate:	0.765

ADMET: Excretion

Clearance (CL):	10.172
Half-life (T1/2):	0.503

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.903
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.78
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.102
Carcinogencity:	0.092
Eye Corrosion:	0.014
Eye Irritation:	0.159
Respiratory Toxicity:	0.739

Download Data

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

Natural Product: NPC474307

Natural Product ID:	NPC474307
*Common Name:**	(2R,4R,6R)-4-Hydroxy-2-Methoxy-6-(1-Phenylallyl)Cyclohexanone
IUPAC Name:	(2R,4R,6R)-4-hydroxy-2-methoxy-6-(1-phenylprop-2-enyl)cyclohexan-1-one
Synonyms:
Standard InCHIKey:	YIXVBISJCATYND-RNLVXLIHSA-N
Standard InCHI:	InChI=1S/C16H20O3/c1-3-13(11-7-5-4-6-8-11)14-9-12(17)10-15(19-2)16(14)18/h3-8,12-15,17H,1,9-10H2,2H3/t12-,13?,14-,15-/m1/s1
SMILES:	C=CC([C@H]1C[C@@H](O)C[C@H](C1=O)OC)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464975
PubChem CID:	11448344
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives

*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	=	2300.0	nM	PMID[448235]

☑ 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 NPC474307 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	189
0.1-0.2	796
0.2-0.3	1850
0.3-0.4	6333
0.4-0.5	12984
0.5-0.6	17621
0.6-0.7	2778
0.7-0.8	140
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8396	Intermediate Similarity	NPC193640
0.8396	Intermediate Similarity	NPC25385
0.8396	Intermediate Similarity	NPC475905
0.82	Intermediate Similarity	NPC141607
0.82	Intermediate Similarity	NPC187725
0.8095	Intermediate Similarity	NPC266343
0.8077	Intermediate Similarity	NPC317280
0.8077	Intermediate Similarity	NPC329387
0.8018	Intermediate Similarity	NPC471189
0.8	Intermediate Similarity	NPC231591
0.7961	Intermediate Similarity	NPC206764
0.7913	Intermediate Similarity	NPC471553
0.7909	Intermediate Similarity	NPC475282
0.7905	Intermediate Similarity	NPC145052
0.7798	Intermediate Similarity	NPC471186
0.7706	Intermediate Similarity	NPC19136
0.7664	Intermediate Similarity	NPC476042
0.7661	Intermediate Similarity	NPC49272
0.7653	Intermediate Similarity	NPC121478
0.7653	Intermediate Similarity	NPC73637
0.7642	Intermediate Similarity	NPC289201
0.7632	Intermediate Similarity	NPC477246
0.7632	Intermediate Similarity	NPC477245
0.7593	Intermediate Similarity	NPC158623
0.7544	Intermediate Similarity	NPC471188
0.7541	Intermediate Similarity	NPC317163
0.7521	Intermediate Similarity	NPC108286
0.75	Intermediate Similarity	NPC476484
0.75	Intermediate Similarity	NPC317645
0.7479	Intermediate Similarity	NPC476645
0.7477	Intermediate Similarity	NPC103048
0.7456	Intermediate Similarity	NPC265513
0.7449	Intermediate Similarity	NPC164449
0.7449	Intermediate Similarity	NPC184030
0.7436	Intermediate Similarity	NPC9274
0.7431	Intermediate Similarity	NPC225079
0.7426	Intermediate Similarity	NPC95965
0.7426	Intermediate Similarity	NPC99482
0.7411	Intermediate Similarity	NPC142326
0.7411	Intermediate Similarity	NPC100767
0.7411	Intermediate Similarity	NPC94751
0.7407	Intermediate Similarity	NPC271475
0.7404	Intermediate Similarity	NPC67585
0.7404	Intermediate Similarity	NPC110420
0.7404	Intermediate Similarity	NPC303967
0.7402	Intermediate Similarity	NPC80599
0.74	Intermediate Similarity	NPC44830
0.7395	Intermediate Similarity	NPC318173
0.7387	Intermediate Similarity	NPC249067
0.7383	Intermediate Similarity	NPC12695
0.7379	Intermediate Similarity	NPC477704
0.7379	Intermediate Similarity	NPC477693
0.7364	Intermediate Similarity	NPC474112
0.7364	Intermediate Similarity	NPC474820
0.7364	Intermediate Similarity	NPC475978
0.7358	Intermediate Similarity	NPC34243
0.7345	Intermediate Similarity	NPC211439
0.7328	Intermediate Similarity	NPC469547
0.7328	Intermediate Similarity	NPC470253
0.7321	Intermediate Similarity	NPC321670
0.7315	Intermediate Similarity	NPC226041
0.7315	Intermediate Similarity	NPC477767
0.7311	Intermediate Similarity	NPC323440
0.7311	Intermediate Similarity	NPC80605
0.7311	Intermediate Similarity	NPC222968
0.7302	Intermediate Similarity	NPC225103
0.7297	Intermediate Similarity	NPC247976
0.7297	Intermediate Similarity	NPC329556
0.7295	Intermediate Similarity	NPC31936
0.7293	Intermediate Similarity	NPC182869
0.7282	Intermediate Similarity	NPC322387
0.7273	Intermediate Similarity	NPC133809
0.7273	Intermediate Similarity	NPC94487
0.7273	Intermediate Similarity	NPC472680
0.7273	Intermediate Similarity	NPC183339
0.7273	Intermediate Similarity	NPC133389
0.7273	Intermediate Similarity	NPC472679
0.7273	Intermediate Similarity	NPC128248
0.7273	Intermediate Similarity	NPC234337
0.7273	Intermediate Similarity	NPC136810
0.7258	Intermediate Similarity	NPC474803
0.7257	Intermediate Similarity	NPC329705
0.7257	Intermediate Similarity	NPC474111
0.7255	Intermediate Similarity	NPC475710
0.7244	Intermediate Similarity	NPC473443
0.7244	Intermediate Similarity	NPC472388
0.7241	Intermediate Similarity	NPC477250
0.7238	Intermediate Similarity	NPC84288
0.7238	Intermediate Similarity	NPC70940
0.7238	Intermediate Similarity	NPC86670
0.7238	Intermediate Similarity	NPC274455
0.7222	Intermediate Similarity	NPC478162
0.7222	Intermediate Similarity	NPC478165
0.7209	Intermediate Similarity	NPC15850
0.7203	Intermediate Similarity	NPC215419
0.72	Intermediate Similarity	NPC470816
0.7182	Intermediate Similarity	NPC221825
0.7177	Intermediate Similarity	NPC138798
0.7172	Intermediate Similarity	NPC272260
0.7156	Intermediate Similarity	NPC324602
0.7155	Intermediate Similarity	NPC477247
0.7154	Intermediate Similarity	NPC369
0.7154	Intermediate Similarity	NPC293831
0.7143	Intermediate Similarity	NPC160382
0.7143	Intermediate Similarity	NPC9796
0.7143	Intermediate Similarity	NPC9822
0.7143	Intermediate Similarity	NPC253681
0.7132	Intermediate Similarity	NPC301946
0.7132	Intermediate Similarity	NPC277053
0.7132	Intermediate Similarity	NPC471162
0.7131	Intermediate Similarity	NPC473243
0.7129	Intermediate Similarity	NPC283012
0.7129	Intermediate Similarity	NPC475199
0.7117	Intermediate Similarity	NPC264728
0.7105	Intermediate Similarity	NPC244933
0.7105	Intermediate Similarity	NPC185763
0.7105	Intermediate Similarity	NPC83409
0.7105	Intermediate Similarity	NPC85560
0.71	Intermediate Similarity	NPC127343
0.71	Intermediate Similarity	NPC477703
0.7097	Intermediate Similarity	NPC182333
0.7097	Intermediate Similarity	NPC273336
0.7094	Intermediate Similarity	NPC292834
0.7091	Intermediate Similarity	NPC210529
0.7091	Intermediate Similarity	NPC160548
0.7091	Intermediate Similarity	NPC175852
0.7087	Intermediate Similarity	NPC195224
0.7087	Intermediate Similarity	NPC477370
0.7083	Intermediate Similarity	NPC470820
0.7083	Intermediate Similarity	NPC108532
0.7083	Intermediate Similarity	NPC325646
0.7083	Intermediate Similarity	NPC28951
0.708	Intermediate Similarity	NPC329282
0.7077	Intermediate Similarity	NPC159811
0.7073	Intermediate Similarity	NPC476234
0.7071	Intermediate Similarity	NPC224544
0.7071	Intermediate Similarity	NPC103488
0.7063	Intermediate Similarity	NPC477363
0.7063	Intermediate Similarity	NPC127975
0.7063	Intermediate Similarity	NPC477366
0.7063	Intermediate Similarity	NPC87985
0.7059	Intermediate Similarity	NPC471912
0.7059	Intermediate Similarity	NPC80895
0.7054	Intermediate Similarity	NPC471334
0.7054	Intermediate Similarity	NPC469519
0.7049	Intermediate Similarity	NPC202015
0.7048	Intermediate Similarity	NPC329064
0.7043	Intermediate Similarity	NPC20485
0.7043	Intermediate Similarity	NPC21929
0.7043	Intermediate Similarity	NPC470007
0.7043	Intermediate Similarity	NPC203732
0.704	Intermediate Similarity	NPC77691
0.704	Intermediate Similarity	NPC469742
0.704	Intermediate Similarity	NPC140118
0.704	Intermediate Similarity	NPC472681
0.704	Intermediate Similarity	NPC12881
0.704	Intermediate Similarity	NPC318067
0.704	Intermediate Similarity	NPC328107
0.7034	Intermediate Similarity	NPC306977
0.7034	Intermediate Similarity	NPC206414
0.7034	Intermediate Similarity	NPC128368
0.7034	Intermediate Similarity	NPC287055
0.7034	Intermediate Similarity	NPC242957
0.7034	Intermediate Similarity	NPC143768
0.7031	Intermediate Similarity	NPC226101
0.7031	Intermediate Similarity	NPC476024
0.7031	Intermediate Similarity	NPC237182
0.7031	Intermediate Similarity	NPC37968
0.7027	Intermediate Similarity	NPC54647
0.7027	Intermediate Similarity	NPC7435
0.7025	Intermediate Similarity	NPC76308
0.7025	Intermediate Similarity	NPC325295
0.7018	Intermediate Similarity	NPC134120
0.7009	Intermediate Similarity	NPC252544
0.7009	Intermediate Similarity	NPC220596
0.7009	Intermediate Similarity	NPC321252
0.7009	Intermediate Similarity	NPC86987
0.7008	Intermediate Similarity	NPC146239
0.7008	Intermediate Similarity	NPC477365
0.7	Intermediate Similarity	NPC209851
0.7	Intermediate Similarity	NPC476976
0.7	Intermediate Similarity	NPC188010
0.7	Intermediate Similarity	NPC62138
0.6992	Remote Similarity	NPC473136
0.6992	Remote Similarity	NPC105709
0.6991	Remote Similarity	NPC274443
0.6984	Remote Similarity	NPC231767
0.6984	Remote Similarity	NPC57607
0.6983	Remote Similarity	NPC64642
0.6983	Remote Similarity	NPC472982
0.6983	Remote Similarity	NPC317305
0.6983	Remote Similarity	NPC149455
0.6977	Remote Similarity	NPC27712
0.6977	Remote Similarity	NPC183722
0.6975	Remote Similarity	NPC241851
0.6975	Remote Similarity	NPC326664
0.6975	Remote Similarity	NPC294458
0.6972	Remote Similarity	NPC172925
0.697	Remote Similarity	NPC298023
0.697	Remote Similarity	NPC23894

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 NPC474307 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	737
0.2-0.3	1272
0.3-0.4	3081
0.4-0.5	2358
0.5-0.6	1300
0.6-0.7	211
0.7-0.8	22
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
0.7798	Intermediate Similarity	NPD5048	Discontinued
0.7727	Intermediate Similarity	NPD6685	Approved
0.7692	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD2629	Approved
0.7615	Intermediate Similarity	NPD5765	Approved
0.75	Intermediate Similarity	NPD2066	Phase 3
0.7456	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD3672	Approved
0.7404	Intermediate Similarity	NPD3673	Approved
0.7387	Intermediate Similarity	NPD1237	Approved
0.7308	Intermediate Similarity	NPD5347	Phase 2
0.7308	Intermediate Similarity	NPD5346	Phase 2
0.7297	Intermediate Similarity	NPD1929	Approved
0.7297	Intermediate Similarity	NPD6647	Phase 2
0.7297	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1930	Approved
0.729	Intermediate Similarity	NPD1693	Approved
0.7241	Intermediate Similarity	NPD6912	Phase 3
0.7238	Intermediate Similarity	NPD1089	Approved
0.7238	Intermediate Similarity	NPD1090	Approved
0.7238	Intermediate Similarity	NPD1086	Approved
0.7222	Intermediate Similarity	NPD1989	Approved
0.7209	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1932	Approved
0.72	Intermediate Similarity	NPD226	Approved
0.7182	Intermediate Similarity	NPD7798	Approved
0.7143	Intermediate Similarity	NPD800	Approved
0.713	Intermediate Similarity	NPD2329	Discontinued
0.7117	Intermediate Similarity	NPD3135	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4793	Discontinued
0.7103	Intermediate Similarity	NPD1088	Approved
0.7091	Intermediate Similarity	NPD9495	Approved
0.708	Intermediate Similarity	NPD5909	Discontinued
0.7034	Intermediate Similarity	NPD7094	Approved
0.7034	Intermediate Similarity	NPD6858	Approved
0.7009	Intermediate Similarity	NPD1239	Approved
0.7	Intermediate Similarity	NPD1564	Approved
0.7	Intermediate Similarity	NPD1566	Phase 3
0.7	Intermediate Similarity	NPD3317	Approved
0.7	Intermediate Similarity	NPD1565	Approved
0.6991	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD1087	Approved
0.6923	Remote Similarity	NPD2067	Discontinued
0.69	Remote Similarity	NPD227	Approved
0.69	Remote Similarity	NPD225	Approved
0.6893	Remote Similarity	NPD9491	Approved
0.6875	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7961	Discontinued
0.6855	Remote Similarity	NPD5305	Approved
0.6855	Remote Similarity	NPD5306	Approved
0.6833	Remote Similarity	NPD2650	Approved
0.6833	Remote Similarity	NPD2652	Approved
0.6829	Remote Similarity	NPD7741	Discontinued
0.6769	Remote Similarity	NPD2613	Approved
0.6757	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6065	Approved
0.6748	Remote Similarity	NPD7610	Discontinued
0.6746	Remote Similarity	NPD2612	Approved
0.6746	Remote Similarity	NPD2609	Approved
0.6746	Remote Similarity	NPD2608	Approved
0.6746	Remote Similarity	NPD4217	Approved
0.6746	Remote Similarity	NPD4806	Approved
0.6746	Remote Similarity	NPD4807	Approved
0.6746	Remote Similarity	NPD3132	Approved
0.6746	Remote Similarity	NPD2610	Approved
0.6746	Remote Similarity	NPD3131	Approved
0.6746	Remote Similarity	NPD2611	Approved
0.6746	Remote Similarity	NPD4215	Approved
0.6746	Remote Similarity	NPD4218	Approved
0.6746	Remote Similarity	NPD4216	Approved
0.6727	Remote Similarity	NPD1563	Approved
0.6723	Remote Similarity	NPD3643	Approved
0.6723	Remote Similarity	NPD3642	Approved
0.6723	Remote Similarity	NPD3644	Approved
0.6721	Remote Similarity	NPD4198	Discontinued
0.6696	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6010	Discontinued
0.6667	Remote Similarity	NPD4136	Approved
0.6667	Remote Similarity	NPD4106	Approved
0.6667	Remote Similarity	NPD4135	Approved
0.664	Remote Similarity	NPD5981	Approved
0.6639	Remote Similarity	NPD1317	Discontinued
0.6636	Remote Similarity	NPD7631	Approved
0.6617	Remote Similarity	NPD2571	Approved
0.6617	Remote Similarity	NPD3614	Approved
0.6617	Remote Similarity	NPD2573	Approved
0.6617	Remote Similarity	NPD2574	Discontinued
0.6617	Remote Similarity	NPD3615	Approved
0.6617	Remote Similarity	NPD2570	Approved
0.6617	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD3089	Approved
0.6617	Remote Similarity	NPD4746	Phase 3
0.6617	Remote Similarity	NPD3616	Approved
0.6617	Remote Similarity	NPD2566	Approved
0.6617	Remote Similarity	NPD3087	Approved
0.6617	Remote Similarity	NPD4745	Approved
0.6617	Remote Similarity	NPD3088	Approved
0.6617	Remote Similarity	NPD3090	Approved
0.6615	Remote Similarity	NPD6085	Phase 2
0.6615	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD3019	Approved
0.6587	Remote Similarity	NPD2932	Approved
0.6583	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3718	Approved
0.6577	Remote Similarity	NPD3719	Approved
0.6562	Remote Similarity	NPD1608	Approved
0.656	Remote Similarity	NPD7009	Phase 2
0.6549	Remote Similarity	NPD3495	Discontinued
0.6545	Remote Similarity	NPD7609	Phase 3
0.6538	Remote Similarity	NPD942	Approved
0.6532	Remote Similarity	NPD4574	Approved
0.6532	Remote Similarity	NPD4576	Approved
0.6525	Remote Similarity	NPD467	Phase 1
0.6525	Remote Similarity	NPD7236	Approved
0.6519	Remote Similarity	NPD6355	Discontinued
0.6519	Remote Similarity	NPD4685	Phase 3
0.6519	Remote Similarity	NPD4686	Approved
0.6519	Remote Similarity	NPD4684	Phase 3
0.6518	Remote Similarity	NPD4814	Discontinued
0.6508	Remote Similarity	NPD4102	Approved
0.6508	Remote Similarity	NPD4105	Approved
0.6505	Remote Similarity	NPD9490	Approved
0.6504	Remote Similarity	NPD1711	Phase 2
0.6491	Remote Similarity	NPD253	Approved
0.6466	Remote Similarity	NPD4719	Phase 2
0.6457	Remote Similarity	NPD5125	Phase 3
0.6457	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5126	Approved
0.6454	Remote Similarity	NPD6190	Approved
0.6441	Remote Similarity	NPD1018	Approved
0.6439	Remote Similarity	NPD5204	Approved
0.6435	Remote Similarity	NPD3020	Approved
0.6435	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1066	Discontinued
0.6429	Remote Similarity	NPD4479	Discontinued
0.6423	Remote Similarity	NPD3598	Phase 3
0.6422	Remote Similarity	NPD531	Approved
0.6406	Remote Similarity	NPD4879	Approved
0.6406	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD5201	Approved
0.6391	Remote Similarity	NPD4617	Approved
0.6391	Remote Similarity	NPD5203	Approved
0.6391	Remote Similarity	NPD4620	Approved
0.6385	Remote Similarity	NPD5159	Phase 2
0.6385	Remote Similarity	NPD5157	Phase 1
0.6385	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD7305	Phase 1
0.6372	Remote Similarity	NPD4094	Approved
0.6371	Remote Similarity	NPD5951	Approved
0.6371	Remote Similarity	NPD690	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6663	Approved
0.6364	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4750	Phase 3
0.6348	Remote Similarity	NPD5926	Approved
0.6339	Remote Similarity	NPD1508	Approved
0.6336	Remote Similarity	NPD5667	Approved
0.6331	Remote Similarity	NPD6099	Approved
0.6331	Remote Similarity	NPD6100	Approved
0.633	Remote Similarity	NPD650	Approved
0.6328	Remote Similarity	NPD17	Approved
0.6328	Remote Similarity	NPD2345	Approved
0.6324	Remote Similarity	NPD5119	Approved
0.6324	Remote Similarity	NPD5121	Approved
0.6324	Remote Similarity	NPD5120	Approved
0.6316	Remote Similarity	NPD5736	Approved
0.6316	Remote Similarity	NPD3664	Approved
0.6316	Remote Similarity	NPD3663	Approved
0.6316	Remote Similarity	NPD3662	Phase 3
0.6316	Remote Similarity	NPD3661	Approved
0.6308	Remote Similarity	NPD6637	Approved
0.6301	Remote Similarity	NPD7239	Suspended
0.6296	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6798	Discontinued
0.6288	Remote Similarity	NPD2159	Approved
0.6288	Remote Similarity	NPD2628	Approved
0.6288	Remote Similarity	NPD2627	Approved
0.6288	Remote Similarity	NPD2625	Approved
0.6288	Remote Similarity	NPD2160	Approved
0.6288	Remote Similarity	NPD2626	Approved
0.6286	Remote Similarity	NPD6005	Phase 3
0.6286	Remote Similarity	NPD6002	Phase 3
0.6286	Remote Similarity	NPD6004	Phase 3
0.6286	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD2182	Approved
0.6281	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3026	Approved
0.6279	Remote Similarity	NPD3023	Approved
0.6273	Remote Similarity	NPD1101	Approved
0.6269	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD2575	Approved
0.6262	Remote Similarity	NPD3971	Phase 1
0.6261	Remote Similarity	NPD4657	Approved
0.6261	Remote Similarity	NPD4655	Approved
0.625	Remote Similarity	NPD5706	Approved
0.625	Remote Similarity	NPD7715	Approved
0.625	Remote Similarity	NPD1651	Approved
0.625	Remote Similarity	NPD5705	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