NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.13
Volume:	278.731
LogP:	1.812
LogD:	2.014
LogS:	-4.005
# 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:	0.903
Synthetic Accessibility Score:	3.254
Fsp3:	0.312
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:	-4.636
MDCK Permeability:	1.9477005480439402e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.072
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.153

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.594
Plasma Protein Binding (PPB):	92.2313003540039%
Volume Distribution (VD):	0.509
Pgp-substrate:	2.6864585876464844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.489
CYP1A2-substrate:	0.758
CYP2C19-inhibitor:	0.312
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.206
CYP2D6-substrate:	0.532
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.472

ADMET: Excretion

Clearance (CL):	8.63
Half-life (T1/2):	0.799

ADMET: Toxicity

hERG Blockers:	0.095
Human Hepatotoxicity (H-HT):	0.501
Drug-inuced Liver Injury (DILI):	0.105
AMES Toxicity:	0.3
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.836
Skin Sensitization:	0.951
Carcinogencity:	0.899
Eye Corrosion:	0.138
Eye Irritation:	0.957
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC114144

Natural Product ID:	NPC114144
*Common Name:**	(1'r)-Candenatenin C
IUPAC Name:	(4R)-4-hydroxy-4-[(E)-3-(2-methoxyphenyl)prop-2-enyl]cyclohex-2-en-1-one
Synonyms:	(1'R)-Candenatenin C
Standard InCHIKey:	WJIWNOUBPSGZMZ-MQDFFIGUSA-N
Standard InCHI:	InChI=1S/C16H18O3/c1-19-15-7-3-2-5-13(15)6-4-10-16(18)11-8-14(17)9-12-16/h2-8,11,18H,9-10,12H2,1H3/b6-4+/t16-/m1/s1
SMILES:	COc1ccccc1/C=C/C[C@]1(O)CCC(=O)C=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078119
PubChem CID:	44254877
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19653666]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	Thai	n.a.	PMID[3430167]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	17800.0	nM	PMID[569910]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	70900.0	nM	PMID[569910]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	48800.0	nM	PMID[569910]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	54200.0	nM	PMID[569910]

☑ 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 NPC114144 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	228
0.1-0.2	1563
0.2-0.3	4257
0.3-0.4	10181
0.4-0.5	8077
0.5-0.6	6111
0.6-0.7	9910
0.7-0.8	2288
0.8-0.85	79
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8938	High Similarity	NPC19290
0.8624	High Similarity	NPC227255
0.8475	Intermediate Similarity	NPC470092
0.8475	Intermediate Similarity	NPC474874
0.8448	Intermediate Similarity	NPC33717
0.8376	Intermediate Similarity	NPC240664
0.8349	Intermediate Similarity	NPC84325
0.8333	Intermediate Similarity	NPC476165
0.8319	Intermediate Similarity	NPC31314
0.8319	Intermediate Similarity	NPC193193
0.8305	Intermediate Similarity	NPC152159
0.8273	Intermediate Similarity	NPC298224
0.8264	Intermediate Similarity	NPC49441
0.8264	Intermediate Similarity	NPC286573
0.8261	Intermediate Similarity	NPC199462
0.8241	Intermediate Similarity	NPC175298
0.8235	Intermediate Similarity	NPC43435
0.822	Intermediate Similarity	NPC469954
0.8198	Intermediate Similarity	NPC38209
0.8198	Intermediate Similarity	NPC2518
0.8197	Intermediate Similarity	NPC242372
0.8197	Intermediate Similarity	NPC257976
0.8197	Intermediate Similarity	NPC4181
0.8197	Intermediate Similarity	NPC164778
0.819	Intermediate Similarity	NPC53953
0.819	Intermediate Similarity	NPC279916
0.8189	Intermediate Similarity	NPC251549
0.8175	Intermediate Similarity	NPC469929
0.8174	Intermediate Similarity	NPC23332
0.816	Intermediate Similarity	NPC201419
0.8158	Intermediate Similarity	NPC234639
0.8145	Intermediate Similarity	NPC179777
0.814	Intermediate Similarity	NPC281513
0.814	Intermediate Similarity	NPC22222
0.8136	Intermediate Similarity	NPC268317
0.813	Intermediate Similarity	NPC4012
0.813	Intermediate Similarity	NPC89630
0.813	Intermediate Similarity	NPC312404
0.813	Intermediate Similarity	NPC273686
0.8125	Intermediate Similarity	NPC327410
0.8125	Intermediate Similarity	NPC288760
0.8115	Intermediate Similarity	NPC114298
0.8099	Intermediate Similarity	NPC131868
0.8099	Intermediate Similarity	NPC158949
0.8095	Intermediate Similarity	NPC238309
0.8087	Intermediate Similarity	NPC473809
0.8087	Intermediate Similarity	NPC183648
0.8083	Intermediate Similarity	NPC264976
0.8083	Intermediate Similarity	NPC61779
0.808	Intermediate Similarity	NPC5018
0.808	Intermediate Similarity	NPC123228
0.808	Intermediate Similarity	NPC95034
0.808	Intermediate Similarity	NPC142087
0.808	Intermediate Similarity	NPC470841
0.808	Intermediate Similarity	NPC123722
0.808	Intermediate Similarity	NPC151167
0.808	Intermediate Similarity	NPC276466
0.808	Intermediate Similarity	NPC121104
0.8067	Intermediate Similarity	NPC183154
0.8067	Intermediate Similarity	NPC263754
0.8067	Intermediate Similarity	NPC45104
0.8065	Intermediate Similarity	NPC4164
0.8053	Intermediate Similarity	NPC69332
0.8053	Intermediate Similarity	NPC95178
0.8053	Intermediate Similarity	NPC29989
0.8053	Intermediate Similarity	NPC113457
0.8051	Intermediate Similarity	NPC188907
0.8049	Intermediate Similarity	NPC182646
0.8047	Intermediate Similarity	NPC118253
0.8047	Intermediate Similarity	NPC309717
0.8047	Intermediate Similarity	NPC189106
0.8047	Intermediate Similarity	NPC66384
0.8047	Intermediate Similarity	NPC128348
0.8047	Intermediate Similarity	NPC312560
0.8047	Intermediate Similarity	NPC112192
0.8047	Intermediate Similarity	NPC164236
0.8033	Intermediate Similarity	NPC251259
0.8031	Intermediate Similarity	NPC196621
0.8031	Intermediate Similarity	NPC247779
0.8031	Intermediate Similarity	NPC245395
0.8031	Intermediate Similarity	NPC172673
0.8031	Intermediate Similarity	NPC146615
0.8017	Intermediate Similarity	NPC54626
0.8017	Intermediate Similarity	NPC168050
0.8017	Intermediate Similarity	NPC470355
0.8	Intermediate Similarity	NPC276014
0.8	Intermediate Similarity	NPC303680
0.8	Intermediate Similarity	NPC171023
0.8	Intermediate Similarity	NPC84076
0.8	Intermediate Similarity	NPC90128
0.7984	Intermediate Similarity	NPC147896
0.7984	Intermediate Similarity	NPC98509
0.7984	Intermediate Similarity	NPC193805
0.7984	Intermediate Similarity	NPC56332
0.7984	Intermediate Similarity	NPC221798
0.7983	Intermediate Similarity	NPC28951
0.7983	Intermediate Similarity	NPC325646
0.7983	Intermediate Similarity	NPC128825
0.7982	Intermediate Similarity	NPC141523
0.7982	Intermediate Similarity	NPC233320
0.7969	Intermediate Similarity	NPC205360
0.7967	Intermediate Similarity	NPC311219
0.7967	Intermediate Similarity	NPC217756
0.7967	Intermediate Similarity	NPC139171
0.7966	Intermediate Similarity	NPC81808
0.7953	Intermediate Similarity	NPC304622
0.7953	Intermediate Similarity	NPC474289
0.7953	Intermediate Similarity	NPC187907
0.7949	Intermediate Similarity	NPC474920
0.7939	Intermediate Similarity	NPC266245
0.7939	Intermediate Similarity	NPC21797
0.7939	Intermediate Similarity	NPC194847
0.7937	Intermediate Similarity	NPC319422
0.7937	Intermediate Similarity	NPC477211
0.7937	Intermediate Similarity	NPC477214
0.7937	Intermediate Similarity	NPC477212
0.7937	Intermediate Similarity	NPC71525
0.7934	Intermediate Similarity	NPC90522
0.7934	Intermediate Similarity	NPC328459
0.7934	Intermediate Similarity	NPC54243
0.7934	Intermediate Similarity	NPC201284
0.7931	Intermediate Similarity	NPC222905
0.7931	Intermediate Similarity	NPC141068
0.7928	Intermediate Similarity	NPC13755
0.7923	Intermediate Similarity	NPC263670
0.7923	Intermediate Similarity	NPC337373
0.7923	Intermediate Similarity	NPC192304
0.7923	Intermediate Similarity	NPC27643
0.7923	Intermediate Similarity	NPC139813
0.7923	Intermediate Similarity	NPC242294
0.7923	Intermediate Similarity	NPC56031
0.7923	Intermediate Similarity	NPC188646
0.7923	Intermediate Similarity	NPC312318
0.7923	Intermediate Similarity	NPC472365
0.7923	Intermediate Similarity	NPC175098
0.792	Intermediate Similarity	NPC224657
0.7917	Intermediate Similarity	NPC217423
0.7917	Intermediate Similarity	NPC280001
0.7913	Intermediate Similarity	NPC224584
0.7907	Intermediate Similarity	NPC329427
0.7907	Intermediate Similarity	NPC262359
0.7907	Intermediate Similarity	NPC64359
0.7907	Intermediate Similarity	NPC475008
0.7907	Intermediate Similarity	NPC186097
0.7907	Intermediate Similarity	NPC475009
0.7907	Intermediate Similarity	NPC317601
0.7907	Intermediate Similarity	NPC308037
0.7907	Intermediate Similarity	NPC239302
0.7903	Intermediate Similarity	NPC473942
0.7903	Intermediate Similarity	NPC18984
0.7903	Intermediate Similarity	NPC93730
0.7903	Intermediate Similarity	NPC229084
0.7903	Intermediate Similarity	NPC160900
0.7903	Intermediate Similarity	NPC106659
0.7899	Intermediate Similarity	NPC51345
0.7899	Intermediate Similarity	NPC296526
0.7899	Intermediate Similarity	NPC23402
0.7895	Intermediate Similarity	NPC470407
0.7895	Intermediate Similarity	NPC1065
0.7895	Intermediate Similarity	NPC477408
0.7895	Intermediate Similarity	NPC326447
0.7895	Intermediate Similarity	NPC70843
0.7891	Intermediate Similarity	NPC327457
0.7891	Intermediate Similarity	NPC7569
0.7891	Intermediate Similarity	NPC2989
0.7891	Intermediate Similarity	NPC86774
0.7886	Intermediate Similarity	NPC201777
0.7881	Intermediate Similarity	NPC141003
0.7881	Intermediate Similarity	NPC90903
0.7881	Intermediate Similarity	NPC109241
0.7881	Intermediate Similarity	NPC35344
0.7879	Intermediate Similarity	NPC130976
0.7879	Intermediate Similarity	NPC309452
0.7874	Intermediate Similarity	NPC80694
0.7874	Intermediate Similarity	NPC186098
0.7874	Intermediate Similarity	NPC2596
0.7874	Intermediate Similarity	NPC2401
0.7869	Intermediate Similarity	NPC72977
0.7863	Intermediate Similarity	NPC57879
0.7863	Intermediate Similarity	NPC286336
0.7857	Intermediate Similarity	NPC472585
0.7851	Intermediate Similarity	NPC212743
0.7851	Intermediate Similarity	NPC94637
0.7851	Intermediate Similarity	NPC32298
0.7846	Intermediate Similarity	NPC470871
0.7846	Intermediate Similarity	NPC257756
0.7846	Intermediate Similarity	NPC129132
0.7846	Intermediate Similarity	NPC87231
0.7846	Intermediate Similarity	NPC205468
0.7846	Intermediate Similarity	NPC212631
0.7845	Intermediate Similarity	NPC471954
0.7845	Intermediate Similarity	NPC75272
0.7845	Intermediate Similarity	NPC88141
0.784	Intermediate Similarity	NPC6888
0.784	Intermediate Similarity	NPC474803
0.784	Intermediate Similarity	NPC276962
0.784	Intermediate Similarity	NPC190086
0.7838	Intermediate Similarity	NPC100870
0.7838	Intermediate Similarity	NPC474308
0.7826	Intermediate Similarity	NPC157473

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 NPC114144 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	971
0.2-0.3	1329
0.3-0.4	2524
0.4-0.5	2057
0.5-0.6	1339
0.6-0.7	591
0.7-0.8	99
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8348	Intermediate Similarity	NPD1241	Discontinued
0.8065	Intermediate Similarity	NPD2797	Approved
0.8	Intermediate Similarity	NPD2798	Approved
0.7983	Intermediate Similarity	NPD9493	Approved
0.7967	Intermediate Similarity	NPD9717	Approved
0.7903	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3134	Approved
0.7891	Intermediate Similarity	NPD3268	Approved
0.7823	Intermediate Similarity	NPD3972	Approved
0.7807	Intermediate Similarity	NPD9697	Approved
0.7778	Intermediate Similarity	NPD1203	Approved
0.7769	Intermediate Similarity	NPD5536	Phase 2
0.7769	Intermediate Similarity	NPD1240	Approved
0.775	Intermediate Similarity	NPD6671	Approved
0.7742	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1778	Approved
0.7724	Intermediate Similarity	NPD4626	Approved
0.7698	Intermediate Similarity	NPD3225	Approved
0.7672	Intermediate Similarity	NPD290	Approved
0.7672	Intermediate Similarity	NPD1358	Approved
0.7669	Intermediate Similarity	NPD2799	Discontinued
0.7661	Intermediate Similarity	NPD3496	Discontinued
0.7661	Intermediate Similarity	NPD3847	Discontinued
0.7652	Intermediate Similarity	NPD1607	Approved
0.7615	Intermediate Similarity	NPD2313	Discontinued
0.7612	Intermediate Similarity	NPD2935	Discontinued
0.7597	Intermediate Similarity	NPD6832	Phase 2
0.7586	Intermediate Similarity	NPD968	Approved
0.7574	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD9545	Approved
0.7561	Intermediate Similarity	NPD1894	Discontinued
0.7559	Intermediate Similarity	NPD1876	Approved
0.7556	Intermediate Similarity	NPD2344	Approved
0.7541	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD4308	Phase 3
0.7519	Intermediate Similarity	NPD9494	Approved
0.7518	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3266	Approved
0.75	Intermediate Similarity	NPD1651	Approved
0.75	Intermediate Similarity	NPD3267	Approved
0.7481	Intermediate Similarity	NPD6798	Discontinued
0.7481	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD422	Phase 1
0.7458	Intermediate Similarity	NPD2684	Approved
0.7444	Intermediate Similarity	NPD447	Suspended
0.7426	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1510	Phase 2
0.7407	Intermediate Similarity	NPD7033	Discontinued
0.7391	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7003	Approved
0.7373	Intermediate Similarity	NPD9267	Approved
0.7373	Intermediate Similarity	NPD9264	Approved
0.7373	Intermediate Similarity	NPD9263	Approved
0.7372	Intermediate Similarity	NPD2424	Discontinued
0.736	Intermediate Similarity	NPD5691	Approved
0.736	Intermediate Similarity	NPD5585	Approved
0.7348	Intermediate Similarity	NPD411	Approved
0.7338	Intermediate Similarity	NPD2309	Approved
0.7323	Intermediate Similarity	NPD1535	Discovery
0.7321	Intermediate Similarity	NPD2934	Approved
0.7321	Intermediate Similarity	NPD2933	Approved
0.7313	Intermediate Similarity	NPD6355	Discontinued
0.7311	Intermediate Similarity	NPD74	Approved
0.7311	Intermediate Similarity	NPD9266	Approved
0.7308	Intermediate Similarity	NPD1019	Discontinued
0.7308	Intermediate Similarity	NPD5647	Approved
0.7299	Intermediate Similarity	NPD2346	Discontinued
0.7287	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD228	Approved
0.7273	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2232	Approved
0.7266	Intermediate Similarity	NPD2230	Approved
0.7266	Intermediate Similarity	NPD2233	Approved
0.7266	Intermediate Similarity	NPD1608	Approved
0.7266	Intermediate Similarity	NPD3750	Approved
0.7266	Intermediate Similarity	NPD1481	Phase 2
0.7257	Intermediate Similarity	NPD2859	Approved
0.7257	Intermediate Similarity	NPD2860	Approved
0.725	Intermediate Similarity	NPD5451	Approved
0.7246	Intermediate Similarity	NPD1549	Phase 2
0.7239	Intermediate Similarity	NPD3140	Approved
0.7239	Intermediate Similarity	NPD3142	Approved
0.7239	Intermediate Similarity	NPD4307	Phase 2
0.7226	Intermediate Similarity	NPD6099	Approved
0.7226	Intermediate Similarity	NPD1551	Phase 2
0.7226	Intermediate Similarity	NPD6100	Approved
0.7226	Intermediate Similarity	NPD2796	Approved
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7843	Approved
0.7213	Intermediate Similarity	NPD5535	Approved
0.7213	Intermediate Similarity	NPD821	Approved
0.7209	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4749	Approved
0.7185	Intermediate Similarity	NPD1933	Approved
0.7185	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD9295	Approved
0.7174	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2668	Approved
0.7165	Intermediate Similarity	NPD2667	Approved
0.7164	Intermediate Similarity	NPD4062	Phase 3
0.7164	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7113	Intermediate Similarity	NPD6799	Approved
0.7105	Intermediate Similarity	NPD844	Approved
0.7103	Intermediate Similarity	NPD7458	Discontinued
0.7101	Intermediate Similarity	NPD4476	Approved
0.7101	Intermediate Similarity	NPD4477	Approved
0.7097	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3764	Approved
0.7083	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD845	Approved
0.708	Intermediate Similarity	NPD7097	Phase 1
0.7077	Intermediate Similarity	NPD4359	Approved
0.7073	Intermediate Similarity	NPD1138	Approved
0.7069	Intermediate Similarity	NPD3020	Approved
0.7068	Intermediate Similarity	NPD2614	Approved
0.7063	Intermediate Similarity	NPD4661	Approved
0.7063	Intermediate Similarity	NPD4662	Approved
0.7059	Intermediate Similarity	NPD4622	Approved
0.7059	Intermediate Similarity	NPD4618	Approved
0.7054	Intermediate Similarity	NPD1091	Approved
0.7054	Intermediate Similarity	NPD1281	Approved
0.7045	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7157	Approved
0.704	Intermediate Similarity	NPD2557	Approved
0.704	Intermediate Similarity	NPD709	Approved
0.7034	Intermediate Similarity	NPD9261	Approved
0.7031	Intermediate Similarity	NPD17	Approved
0.7031	Intermediate Similarity	NPD2932	Approved
0.7029	Intermediate Similarity	NPD3748	Approved
0.7023	Intermediate Similarity	NPD196	Phase 1
0.7016	Intermediate Similarity	NPD5283	Phase 1
0.7015	Intermediate Similarity	NPD7095	Approved
0.7014	Intermediate Similarity	NPD5049	Phase 3
0.7007	Intermediate Similarity	NPD7411	Suspended
0.7007	Intermediate Similarity	NPD6651	Approved
0.7	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1139	Approved
0.6992	Remote Similarity	NPD1137	Approved
0.6986	Remote Similarity	NPD3226	Approved
0.6986	Remote Similarity	NPD2649	Approved
0.6986	Remote Similarity	NPD2651	Approved
0.6985	Remote Similarity	NPD4060	Phase 1
0.6978	Remote Similarity	NPD6032	Approved
0.6975	Remote Similarity	NPD1237	Approved
0.6975	Remote Similarity	NPD5909	Discontinued
0.6972	Remote Similarity	NPD2354	Approved
0.6972	Remote Similarity	NPD111	Approved
0.697	Remote Similarity	NPD6362	Approved
0.697	Remote Similarity	NPD1470	Approved
0.6966	Remote Similarity	NPD5403	Approved
0.6963	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.696	Remote Similarity	NPD9281	Approved
0.6959	Remote Similarity	NPD6844	Discontinued
0.6957	Remote Similarity	NPD5688	Approved
0.6957	Remote Similarity	NPD5689	Approved
0.6949	Remote Similarity	NPD846	Approved
0.6949	Remote Similarity	NPD940	Approved
0.6947	Remote Similarity	NPD6582	Phase 2
0.6947	Remote Similarity	NPD6583	Phase 3
0.694	Remote Similarity	NPD4908	Phase 1
0.6939	Remote Similarity	NPD4380	Phase 2
0.6934	Remote Similarity	NPD1184	Approved
0.6934	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5124	Phase 1
0.6933	Remote Similarity	NPD3882	Suspended
0.6929	Remote Similarity	NPD6005	Phase 3
0.6929	Remote Similarity	NPD6004	Phase 3
0.6929	Remote Similarity	NPD6002	Phase 3
0.6929	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1201	Approved
0.6923	Remote Similarity	NPD7440	Discontinued
0.6923	Remote Similarity	NPD1610	Phase 2
0.6923	Remote Similarity	NPD1238	Approved
0.6913	Remote Similarity	NPD2801	Approved
0.6911	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6387	Discontinued
0.6899	Remote Similarity	NPD3019	Approved
0.6897	Remote Similarity	NPD288	Approved
0.6889	Remote Similarity	NPD5163	Phase 2
0.6889	Remote Similarity	NPD4625	Phase 3
0.6885	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2182	Approved
0.6884	Remote Similarity	NPD6653	Approved
0.6875	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2231	Phase 2
0.687	Remote Similarity	NPD2235	Phase 2
0.687	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.687	Remote Similarity	NPD9296	Approved
0.6866	Remote Similarity	NPD454	Approved
0.6866	Remote Similarity	NPD2861	Phase 2
0.6864	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3887	Approved
0.6846	Remote Similarity	NPD7577	Discontinued

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