NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	224.1
Volume:	232.167
LogP:	0.874
LogD:	0.997
LogS:	-1.169
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.816
Synthetic Accessibility Score:	2.925
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.493
MDCK Permeability:	1.2674436220549978e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.12
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.324
Plasma Protein Binding (PPB):	55.797767639160156%
Volume Distribution (VD):	0.904
Pgp-substrate:	29.365333557128906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.845
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.536

ADMET: Excretion

Clearance (CL):	16.448
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.435
Drug-inuced Liver Injury (DILI):	0.435
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.339
Carcinogencity:	0.081
Eye Corrosion:	0.177
Eye Irritation:	0.797
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC195292

Natural Product ID:	NPC195292
*Common Name:**	(3R,4S)-4-Hydroxy-4-(4-Hydroxy-3-Methoxyphenyl)-3-Methylbutan-2-One
IUPAC Name:	(3R,4S)-4-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-methylbutan-2-one
Synonyms:
Standard InCHIKey:	DCKJTOQHNMSFBW-MADCSZMMSA-N
Standard InCHI:	InChI=1S/C12H16O4/c1-7(8(2)13)12(15)9-4-5-10(14)11(6-9)16-3/h4-7,12,14-15H,1-3H3/t7-,12-/m0/s1
SMILES:	COc1cc(ccc1O)[C@H]([C@H](C(=O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1075681
PubChem CID:	44613161
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO23895	Machilus wangchiana	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[19916529]
NPO23895	Machilus wangchiana	Species	Lauraceae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	43.0	%	PMID[469500]

☑ 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 NPC195292 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	303
0.1-0.2	1261
0.2-0.3	3524
0.3-0.4	9134
0.4-0.5	9727
0.5-0.6	3863
0.6-0.7	8341
0.7-0.8	5922
0.8-0.85	512
0.85-0.9	79
0.9-0.95	19
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC142985
0.976	High Similarity	NPC469480
0.9597	High Similarity	NPC20287
0.9597	High Similarity	NPC20404
0.9597	High Similarity	NPC293641
0.9597	High Similarity	NPC12022
0.952	High Similarity	NPC278308
0.9457	High Similarity	NPC470990
0.937	High Similarity	NPC311419
0.937	High Similarity	NPC244246
0.937	High Similarity	NPC65935
0.937	High Similarity	NPC275724
0.937	High Similarity	NPC215941
0.937	High Similarity	NPC137427
0.937	High Similarity	NPC319282
0.937	High Similarity	NPC123196
0.9274	High Similarity	NPC244876
0.9173	High Similarity	NPC474784
0.912	High Similarity	NPC163083
0.9113	High Similarity	NPC476343
0.9113	High Similarity	NPC201777
0.903	High Similarity	NPC322021
0.9024	High Similarity	NPC299406
0.8976	High Similarity	NPC53305
0.8976	High Similarity	NPC257589
0.8963	High Similarity	NPC470991
0.8906	High Similarity	NPC92207
0.8906	High Similarity	NPC127937
0.8889	High Similarity	NPC114298
0.8871	High Similarity	NPC181969
0.8871	High Similarity	NPC320987
0.8864	High Similarity	NPC327410
0.8864	High Similarity	NPC129889
0.8864	High Similarity	NPC307006
0.8828	High Similarity	NPC280767
0.8824	High Similarity	NPC100675
0.8819	High Similarity	NPC257976
0.8819	High Similarity	NPC164778
0.8819	High Similarity	NPC242372
0.8819	High Similarity	NPC4181
0.8815	High Similarity	NPC325625
0.881	High Similarity	NPC194416
0.881	High Similarity	NPC470804
0.881	High Similarity	NPC177291
0.88	High Similarity	NPC177475
0.88	High Similarity	NPC35071
0.88	High Similarity	NPC148615
0.879	High Similarity	NPC255675
0.8788	High Similarity	NPC50763
0.8769	High Similarity	NPC226661
0.8768	High Similarity	NPC239608
0.8768	High Similarity	NPC46161
0.876	High Similarity	NPC84076
0.876	High Similarity	NPC90128
0.876	High Similarity	NPC303680
0.875	High Similarity	NPC147379
0.875	High Similarity	NPC203351
0.875	High Similarity	NPC312404
0.875	High Similarity	NPC273686
0.8731	High Similarity	NPC152209
0.8731	High Similarity	NPC113295
0.873	High Similarity	NPC158949
0.872	High Similarity	NPC311595
0.872	High Similarity	NPC135961
0.872	High Similarity	NPC24474
0.8714	High Similarity	NPC472333
0.8714	High Similarity	NPC208507
0.871	High Similarity	NPC164386
0.8705	High Similarity	NPC223185
0.8702	High Similarity	NPC304622
0.8692	High Similarity	NPC123228
0.8692	High Similarity	NPC118533
0.8692	High Similarity	NPC123722
0.8692	High Similarity	NPC281020
0.8692	High Similarity	NPC276466
0.8692	High Similarity	NPC5018
0.8692	High Similarity	NPC165045
0.8692	High Similarity	NPC151167
0.8682	High Similarity	NPC148627
0.8672	High Similarity	NPC471693
0.8657	High Similarity	NPC471110
0.8652	High Similarity	NPC1580
0.8647	High Similarity	NPC239302
0.8636	High Similarity	NPC172673
0.8633	High Similarity	NPC27159
0.8629	High Similarity	NPC221049
0.8615	High Similarity	NPC179777
0.8594	High Similarity	NPC209567
0.8594	High Similarity	NPC85488
0.8593	High Similarity	NPC139519
0.8583	High Similarity	NPC98305
0.8583	High Similarity	NPC207613
0.8561	High Similarity	NPC475875
0.855	High Similarity	NPC5428
0.8538	High Similarity	NPC3221
0.8527	High Similarity	NPC165375
0.8527	High Similarity	NPC220598
0.8527	High Similarity	NPC280704
0.8519	High Similarity	NPC68779
0.8519	High Similarity	NPC300776
0.8519	High Similarity	NPC176814
0.8519	High Similarity	NPC4982
0.8519	High Similarity	NPC5310
0.8516	High Similarity	NPC470212
0.8516	High Similarity	NPC324571
0.8516	High Similarity	NPC54872
0.8516	High Similarity	NPC343720
0.8516	High Similarity	NPC312675
0.8516	High Similarity	NPC473853
0.8516	High Similarity	NPC262156
0.8516	High Similarity	NPC113865
0.8516	High Similarity	NPC184651
0.8511	High Similarity	NPC474799
0.8504	High Similarity	NPC265454
0.8504	High Similarity	NPC34634
0.8496	Intermediate Similarity	NPC153739
0.8496	Intermediate Similarity	NPC42300
0.8496	Intermediate Similarity	NPC242807
0.8496	Intermediate Similarity	NPC64201
0.8496	Intermediate Similarity	NPC92164
0.8496	Intermediate Similarity	NPC145305
0.8496	Intermediate Similarity	NPC241522
0.8496	Intermediate Similarity	NPC174495
0.8496	Intermediate Similarity	NPC77040
0.8496	Intermediate Similarity	NPC187998
0.8496	Intermediate Similarity	NPC257582
0.8492	Intermediate Similarity	NPC205502
0.8485	Intermediate Similarity	NPC282703
0.8485	Intermediate Similarity	NPC184733
0.8485	Intermediate Similarity	NPC21867
0.8485	Intermediate Similarity	NPC11258
0.8485	Intermediate Similarity	NPC128208
0.8485	Intermediate Similarity	NPC474178
0.8485	Intermediate Similarity	NPC252307
0.8485	Intermediate Similarity	NPC45774
0.8485	Intermediate Similarity	NPC129570
0.8485	Intermediate Similarity	NPC245826
0.8483	Intermediate Similarity	NPC327225
0.8478	Intermediate Similarity	NPC4796
0.8473	Intermediate Similarity	NPC191037
0.8473	Intermediate Similarity	NPC58607
0.8473	Intermediate Similarity	NPC178284
0.8467	Intermediate Similarity	NPC281780
0.8462	Intermediate Similarity	NPC474903
0.8451	Intermediate Similarity	NPC221383
0.8451	Intermediate Similarity	NPC143892
0.8451	Intermediate Similarity	NPC283081
0.8451	Intermediate Similarity	NPC299090
0.8444	Intermediate Similarity	NPC475468
0.844	Intermediate Similarity	NPC469683
0.8433	Intermediate Similarity	NPC277804
0.8433	Intermediate Similarity	NPC474017
0.8425	Intermediate Similarity	NPC25127
0.8421	Intermediate Similarity	NPC170844
0.8421	Intermediate Similarity	NPC476968
0.8421	Intermediate Similarity	NPC241354
0.8417	Intermediate Similarity	NPC19158
0.8413	Intermediate Similarity	NPC293619
0.8409	Intermediate Similarity	NPC292056
0.8409	Intermediate Similarity	NPC16651
0.8409	Intermediate Similarity	NPC319625
0.8409	Intermediate Similarity	NPC183181
0.8409	Intermediate Similarity	NPC32163
0.8409	Intermediate Similarity	NPC147821
0.8409	Intermediate Similarity	NPC118787
0.8409	Intermediate Similarity	NPC111247
0.8409	Intermediate Similarity	NPC41706
0.8409	Intermediate Similarity	NPC163332
0.8397	Intermediate Similarity	NPC194519
0.8394	Intermediate Similarity	NPC90431
0.8392	Intermediate Similarity	NPC98009
0.8382	Intermediate Similarity	NPC67247
0.838	Intermediate Similarity	NPC30890
0.8374	Intermediate Similarity	NPC257124
0.8374	Intermediate Similarity	NPC139617
0.8374	Intermediate Similarity	NPC156840
0.8374	Intermediate Similarity	NPC78918
0.8374	Intermediate Similarity	NPC8547
0.8374	Intermediate Similarity	NPC173746
0.8372	Intermediate Similarity	NPC49341
0.837	Intermediate Similarity	NPC111888
0.837	Intermediate Similarity	NPC106739
0.8369	Intermediate Similarity	NPC469615
0.8359	Intermediate Similarity	NPC227217
0.8359	Intermediate Similarity	NPC117780
0.8359	Intermediate Similarity	NPC95614
0.8359	Intermediate Similarity	NPC165133
0.8359	Intermediate Similarity	NPC232316
0.8359	Intermediate Similarity	NPC242885
0.8359	Intermediate Similarity	NPC56214
0.8358	Intermediate Similarity	NPC143483
0.8357	Intermediate Similarity	NPC52664
0.8357	Intermediate Similarity	NPC31751
0.8357	Intermediate Similarity	NPC472335
0.8357	Intermediate Similarity	NPC253481
0.8357	Intermediate Similarity	NPC472332
0.8357	Intermediate Similarity	NPC253722
0.8356	Intermediate Similarity	NPC473236
0.8346	Intermediate Similarity	NPC186843
0.8346	Intermediate Similarity	NPC98631

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 NPC195292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	833
0.2-0.3	1748
0.3-0.4	2661
0.4-0.5	1810
0.5-0.6	1028
0.6-0.7	679
0.7-0.8	105
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD3027	Phase 3
0.8374	Intermediate Similarity	NPD228	Approved
0.8244	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD9494	Approved
0.8108	Intermediate Similarity	NPD1934	Approved
0.7933	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1613	Approved
0.7821	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6166	Phase 2
0.7815	Intermediate Similarity	NPD2801	Approved
0.7812	Intermediate Similarity	NPD5283	Phase 1
0.7727	Intermediate Similarity	NPD1357	Approved
0.7724	Intermediate Similarity	NPD4110	Phase 3
0.7724	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD3620	Phase 2
0.7714	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3882	Suspended
0.771	Intermediate Similarity	NPD5536	Phase 2
0.7687	Intermediate Similarity	NPD1511	Approved
0.7664	Intermediate Similarity	NPD5647	Approved
0.7632	Intermediate Similarity	NPD37	Approved
0.7625	Intermediate Similarity	NPD7074	Phase 3
0.7613	Intermediate Similarity	NPD6234	Discontinued
0.761	Intermediate Similarity	NPD3818	Discontinued
0.7584	Intermediate Similarity	NPD1512	Approved
0.7568	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7054	Approved
0.7559	Intermediate Similarity	NPD2684	Approved
0.7554	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD230	Phase 1
0.7535	Intermediate Similarity	NPD447	Suspended
0.7535	Intermediate Similarity	NPD6355	Discontinued
0.7516	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD3022	Approved
0.7484	Intermediate Similarity	NPD4965	Approved
0.7484	Intermediate Similarity	NPD4966	Approved
0.7484	Intermediate Similarity	NPD4967	Phase 2
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7483	Intermediate Similarity	NPD6653	Approved
0.7482	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1651	Approved
0.7462	Intermediate Similarity	NPD7843	Approved
0.7448	Intermediate Similarity	NPD9570	Approved
0.7448	Intermediate Similarity	NPD2935	Discontinued
0.7447	Intermediate Similarity	NPD6798	Discontinued
0.7432	Intermediate Similarity	NPD6190	Approved
0.7426	Intermediate Similarity	NPD3705	Approved
0.7424	Intermediate Similarity	NPD7157	Approved
0.7419	Intermediate Similarity	NPD3817	Phase 2
0.7394	Intermediate Similarity	NPD6233	Phase 2
0.7391	Intermediate Similarity	NPD1283	Approved
0.7391	Intermediate Similarity	NPD7228	Approved
0.7379	Intermediate Similarity	NPD1510	Phase 2
0.7372	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1608	Approved
0.7365	Intermediate Similarity	NPD8166	Discontinued
0.7362	Intermediate Similarity	NPD6797	Phase 2
0.7343	Intermediate Similarity	NPD1240	Approved
0.7343	Intermediate Similarity	NPD826	Approved
0.7343	Intermediate Similarity	NPD825	Approved
0.7343	Intermediate Similarity	NPD4060	Phase 1
0.7343	Intermediate Similarity	NPD943	Approved
0.7329	Intermediate Similarity	NPD7473	Discontinued
0.7317	Intermediate Similarity	NPD7251	Discontinued
0.7297	Intermediate Similarity	NPD3060	Approved
0.7296	Intermediate Similarity	NPD8127	Discontinued
0.7279	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7266	Discontinued
0.7279	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD1241	Discontinued
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2674	Phase 3
0.7273	Intermediate Similarity	NPD4062	Phase 3
0.7255	Intermediate Similarity	NPD3687	Approved
0.7255	Intermediate Similarity	NPD1653	Approved
0.7255	Intermediate Similarity	NPD3686	Approved
0.725	Intermediate Similarity	NPD6232	Discontinued
0.7241	Intermediate Similarity	NPD1607	Approved
0.7234	Intermediate Similarity	NPD2861	Phase 2
0.7233	Intermediate Similarity	NPD5494	Approved
0.723	Intermediate Similarity	NPD1549	Phase 2
0.723	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1558	Phase 1
0.7215	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD290	Approved
0.7203	Intermediate Similarity	NPD3144	Approved
0.7203	Intermediate Similarity	NPD3145	Approved
0.7188	Intermediate Similarity	NPD7199	Phase 2
0.7174	Intermediate Similarity	NPD1281	Approved
0.7174	Intermediate Similarity	NPD1535	Discovery
0.7171	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD258	Approved
0.7163	Intermediate Similarity	NPD257	Approved
0.7162	Intermediate Similarity	NPD6005	Phase 3
0.7162	Intermediate Similarity	NPD6002	Phase 3
0.7162	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6004	Phase 3
0.7162	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7028	Phase 2
0.7154	Intermediate Similarity	NPD9296	Approved
0.7153	Intermediate Similarity	NPD9381	Approved
0.7153	Intermediate Similarity	NPD9384	Approved
0.7153	Intermediate Similarity	NPD17	Approved
0.7153	Intermediate Similarity	NPD1778	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7095	Approved
0.7132	Intermediate Similarity	NPD9545	Approved
0.7122	Intermediate Similarity	NPD1481	Phase 2
0.7118	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2424	Discontinued
0.7108	Intermediate Similarity	NPD7685	Pre-registration
0.7107	Intermediate Similarity	NPD7075	Discontinued
0.7103	Intermediate Similarity	NPD2979	Phase 3
0.7101	Intermediate Similarity	NPD3847	Discontinued
0.7095	Intermediate Similarity	NPD5712	Approved
0.7095	Intermediate Similarity	NPD2438	Suspended
0.7087	Intermediate Similarity	NPD291	Approved
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1358	Approved
0.7071	Intermediate Similarity	NPD2983	Phase 2
0.7071	Intermediate Similarity	NPD9622	Approved
0.7071	Intermediate Similarity	NPD2982	Phase 2
0.7071	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4236	Phase 3
0.7067	Intermediate Similarity	NPD4237	Approved
0.7059	Intermediate Similarity	NPD3146	Approved
0.7059	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD555	Phase 2
0.705	Intermediate Similarity	NPD1091	Approved
0.7048	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5763	Approved
0.7047	Intermediate Similarity	NPD5762	Approved
0.7047	Intermediate Similarity	NPD1375	Discontinued
0.7042	Intermediate Similarity	NPD2798	Approved
0.7037	Intermediate Similarity	NPD6671	Approved
0.7034	Intermediate Similarity	NPD259	Phase 1
0.7034	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5844	Phase 1
0.7029	Intermediate Similarity	NPD2932	Approved
0.7029	Intermediate Similarity	NPD3019	Approved
0.7029	Intermediate Similarity	NPD4626	Approved
0.7027	Intermediate Similarity	NPD2799	Discontinued
0.7025	Intermediate Similarity	NPD2978	Approved
0.7025	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2977	Approved
0.702	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1894	Discontinued
0.7006	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD5958	Discontinued
0.7	Intermediate Similarity	NPD4534	Discontinued
0.7	Intermediate Similarity	NPD9269	Phase 2
0.7	Intermediate Similarity	NPD2981	Phase 2
0.6994	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6799	Approved
0.6993	Remote Similarity	NPD3018	Phase 2
0.6987	Remote Similarity	NPD3455	Phase 2
0.6987	Remote Similarity	NPD824	Approved
0.6986	Remote Similarity	NPD2238	Phase 2
0.6981	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5402	Approved
0.698	Remote Similarity	NPD2796	Approved
0.698	Remote Similarity	NPD2161	Phase 2
0.698	Remote Similarity	NPD2240	Approved
0.698	Remote Similarity	NPD6100	Approved
0.698	Remote Similarity	NPD2239	Approved
0.698	Remote Similarity	NPD6099	Approved
0.6978	Remote Similarity	NPD3496	Discontinued
0.6966	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6801	Discontinued
0.6959	Remote Similarity	NPD4536	Approved
0.6959	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7097	Phase 1
0.6959	Remote Similarity	NPD4538	Approved
0.6957	Remote Similarity	NPD5585	Approved
0.6954	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5177	Phase 3
0.6954	Remote Similarity	NPD6674	Discontinued
0.6948	Remote Similarity	NPD2532	Approved
0.6948	Remote Similarity	NPD2533	Approved
0.6948	Remote Similarity	NPD2534	Approved
0.6948	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4908	Phase 1
0.6939	Remote Similarity	NPD5735	Approved
0.6933	Remote Similarity	NPD3787	Discontinued
0.6929	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1610	Phase 2
0.6928	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9621	Approved
0.6923	Remote Similarity	NPD9620	Approved
0.6923	Remote Similarity	NPD9619	Approved
0.6918	Remote Similarity	NPD1465	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