NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.14
Volume:	266.759
LogP:	1.992
LogD:	2.081
LogS:	-2.165
# Rotatable Bonds:	6
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.845
Synthetic Accessibility Score:	3.126
Fsp3:	0.5
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:	-4.456
MDCK Permeability:	1.8957081920234486e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.233
Plasma Protein Binding (PPB):	78.3779296875%
Volume Distribution (VD):	1.029
Pgp-substrate:	12.055452346801758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.134
CYP1A2-substrate:	0.91
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.74
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.831
CYP3A4-inhibitor:	0.125
CYP3A4-substrate:	0.543

ADMET: Excretion

Clearance (CL):	15.681
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.527
Drug-inuced Liver Injury (DILI):	0.657
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.589
Carcinogencity:	0.089
Eye Corrosion:	0.414
Eye Irritation:	0.921
Respiratory Toxicity:	0.154

Download Data

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

Natural Product: NPC469480

Natural Product ID:	NPC469480
*Common Name:**	(3R,4S)-4-Ethoxy-4-(4-Hydroxy-3-Methoxyphenyl)-3-Methylbutan-2-One
IUPAC Name:	(3R,4S)-4-ethoxy-4-(4-hydroxy-3-methoxyphenyl)-3-methylbutan-2-one
Synonyms:
Standard InCHIKey:	YYHIZXWYZAXQKD-XPTSAGLGSA-N
Standard InCHI:	InChI=1S/C14H20O4/c1-5-18-14(9(2)10(3)15)11-6-7-12(16)13(8-11)17-4/h6-9,14,16H,5H2,1-4H3/t9-,14-/m0/s1
SMILES:	CCOC(C1=CC(=C(C=C1)O)OC)C(C)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079840
PubChem CID:	44613296
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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	42.0	%	PMID[495143]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	54.0	%	PMID[495143]

☑ 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 NPC469480 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	312
0.1-0.2	1219
0.2-0.3	3334
0.3-0.4	8419
0.4-0.5	10432
0.5-0.6	3570
0.6-0.7	7665
0.7-0.8	6838
0.8-0.85	761
0.85-0.9	115
0.9-0.95	29
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC142985
0.976	High Similarity	NPC195292
0.9365	High Similarity	NPC12022
0.9365	High Similarity	NPC20404
0.9365	High Similarity	NPC20287
0.9365	High Similarity	NPC293641
0.9291	High Similarity	NPC278308
0.9237	High Similarity	NPC470990
0.9147	High Similarity	NPC311419
0.9147	High Similarity	NPC123196
0.9147	High Similarity	NPC215941
0.9147	High Similarity	NPC137427
0.9147	High Similarity	NPC244246
0.9147	High Similarity	NPC319282
0.9147	High Similarity	NPC275724
0.9147	High Similarity	NPC65935
0.9048	High Similarity	NPC244876
0.9048	High Similarity	NPC163083
0.904	High Similarity	NPC201777
0.8963	High Similarity	NPC474784
0.8963	High Similarity	NPC322021
0.8963	High Similarity	NPC147379
0.8952	High Similarity	NPC299406
0.8913	High Similarity	NPC223185
0.8906	High Similarity	NPC257589
0.8906	High Similarity	NPC280767
0.8906	High Similarity	NPC53305
0.8897	High Similarity	NPC470991
0.8889	High Similarity	NPC470804
0.8889	High Similarity	NPC476343
0.8857	High Similarity	NPC1580
0.8846	High Similarity	NPC226661
0.8841	High Similarity	NPC27159
0.8837	High Similarity	NPC92207
0.8837	High Similarity	NPC127937
0.8819	High Similarity	NPC114298
0.8806	High Similarity	NPC152209
0.88	High Similarity	NPC181969
0.88	High Similarity	NPC320987
0.8797	High Similarity	NPC129889
0.8797	High Similarity	NPC307006
0.8797	High Similarity	NPC327410
0.8786	High Similarity	NPC472333
0.8786	High Similarity	NPC208507
0.8769	High Similarity	NPC281020
0.8759	High Similarity	NPC100675
0.875	High Similarity	NPC257976
0.875	High Similarity	NPC4181
0.875	High Similarity	NPC242372
0.875	High Similarity	NPC325625
0.875	High Similarity	NPC164778
0.874	High Similarity	NPC177291
0.874	High Similarity	NPC194416
0.873	High Similarity	NPC177475
0.873	High Similarity	NPC35071
0.873	High Similarity	NPC148615
0.872	High Similarity	NPC255675
0.8705	High Similarity	NPC239608
0.8705	High Similarity	NPC46161
0.8702	High Similarity	NPC282703
0.8702	High Similarity	NPC21867
0.8702	High Similarity	NPC129570
0.8702	High Similarity	NPC45774
0.8702	High Similarity	NPC11258
0.8702	High Similarity	NPC184733
0.8702	High Similarity	NPC128208
0.8692	High Similarity	NPC84076
0.8692	High Similarity	NPC90128
0.8692	High Similarity	NPC303680
0.8686	High Similarity	NPC203351
0.8682	High Similarity	NPC273686
0.8682	High Similarity	NPC312404
0.8676	High Similarity	NPC281780
0.8672	High Similarity	NPC209567
0.8661	High Similarity	NPC158949
0.8651	High Similarity	NPC135961
0.8636	High Similarity	NPC304622
0.8626	High Similarity	NPC165045
0.8626	High Similarity	NPC5018
0.8626	High Similarity	NPC118533
0.8626	High Similarity	NPC276466
0.8626	High Similarity	NPC123228
0.8626	High Similarity	NPC123722
0.8626	High Similarity	NPC151167
0.8615	High Similarity	NPC3221
0.8615	High Similarity	NPC148627
0.8605	High Similarity	NPC471693
0.8593	High Similarity	NPC471110
0.8593	High Similarity	NPC4982
0.8593	High Similarity	NPC5310
0.8593	High Similarity	NPC300776
0.8593	High Similarity	NPC176814
0.8593	High Similarity	NPC68779
0.8593	High Similarity	NPC67247
0.8582	High Similarity	NPC50763
0.8582	High Similarity	NPC239302
0.8571	High Similarity	NPC174495
0.8571	High Similarity	NPC241522
0.8571	High Similarity	NPC172673
0.8571	High Similarity	NPC92164
0.8571	High Similarity	NPC64201
0.8571	High Similarity	NPC145305
0.8571	High Similarity	NPC42300
0.8571	High Similarity	NPC469615
0.8571	High Similarity	NPC242807
0.8571	High Similarity	NPC187998
0.8571	High Similarity	NPC153739
0.8571	High Similarity	NPC257582
0.8571	High Similarity	NPC77040
0.8561	High Similarity	NPC253722
0.8561	High Similarity	NPC31751
0.8561	High Similarity	NPC472335
0.8561	High Similarity	NPC474178
0.8561	High Similarity	NPC253481
0.8561	High Similarity	NPC252307
0.8561	High Similarity	NPC245826
0.8561	High Similarity	NPC472332
0.856	High Similarity	NPC221049
0.8552	High Similarity	NPC327225
0.8551	High Similarity	NPC288452
0.8551	High Similarity	NPC289690
0.855	High Similarity	NPC179777
0.855	High Similarity	NPC58607
0.855	High Similarity	NPC191037
0.855	High Similarity	NPC178284
0.8531	High Similarity	NPC125570
0.8529	High Similarity	NPC139519
0.8529	High Similarity	NPC113295
0.8521	High Similarity	NPC221383
0.8521	High Similarity	NPC143892
0.8521	High Similarity	NPC299090
0.8521	High Similarity	NPC283081
0.8521	High Similarity	NPC30720
0.8519	High Similarity	NPC475468
0.8516	High Similarity	NPC98305
0.8511	High Similarity	NPC469683
0.8507	High Similarity	NPC27843
0.8507	High Similarity	NPC115207
0.8507	High Similarity	NPC161557
0.8507	High Similarity	NPC158079
0.8507	High Similarity	NPC40432
0.8507	High Similarity	NPC228346
0.8507	High Similarity	NPC277804
0.8507	High Similarity	NPC7171
0.8504	High Similarity	NPC311595
0.8504	High Similarity	NPC24474
0.85	High Similarity	NPC273657
0.85	High Similarity	NPC106920
0.85	High Similarity	NPC285550
0.8496	Intermediate Similarity	NPC241354
0.8496	Intermediate Similarity	NPC475875
0.8493	Intermediate Similarity	NPC25127
0.8492	Intermediate Similarity	NPC164386
0.8489	Intermediate Similarity	NPC19158
0.8485	Intermediate Similarity	NPC111247
0.8485	Intermediate Similarity	NPC118787
0.8485	Intermediate Similarity	NPC163332
0.8485	Intermediate Similarity	NPC292056
0.8485	Intermediate Similarity	NPC319625
0.8485	Intermediate Similarity	NPC183181
0.8485	Intermediate Similarity	NPC5428
0.8485	Intermediate Similarity	NPC147821
0.8485	Intermediate Similarity	NPC41706
0.8473	Intermediate Similarity	NPC194519
0.8467	Intermediate Similarity	NPC90431
0.8467	Intermediate Similarity	NPC471988
0.8462	Intermediate Similarity	NPC220598
0.8462	Intermediate Similarity	NPC165375
0.8462	Intermediate Similarity	NPC98009
0.8456	Intermediate Similarity	NPC106406
0.8456	Intermediate Similarity	NPC37065
0.8451	Intermediate Similarity	NPC474799
0.8451	Intermediate Similarity	NPC30890
0.8444	Intermediate Similarity	NPC181049
0.8444	Intermediate Similarity	NPC207400
0.844	Intermediate Similarity	NPC183824
0.8425	Intermediate Similarity	NPC473236
0.8425	Intermediate Similarity	NPC205502
0.8421	Intermediate Similarity	NPC470084
0.8417	Intermediate Similarity	NPC4796
0.8406	Intermediate Similarity	NPC308976
0.8403	Intermediate Similarity	NPC474903
0.8397	Intermediate Similarity	NPC109822
0.8397	Intermediate Similarity	NPC94276
0.8392	Intermediate Similarity	NPC85734
0.8392	Intermediate Similarity	NPC32058
0.8385	Intermediate Similarity	NPC85488
0.8382	Intermediate Similarity	NPC159418
0.8382	Intermediate Similarity	NPC283823
0.8382	Intermediate Similarity	NPC158331
0.838	Intermediate Similarity	NPC474982
0.838	Intermediate Similarity	NPC258671
0.838	Intermediate Similarity	NPC53884
0.8378	Intermediate Similarity	NPC317383
0.8372	Intermediate Similarity	NPC207613
0.837	Intermediate Similarity	NPC474017
0.8369	Intermediate Similarity	NPC477697
0.8369	Intermediate Similarity	NPC470811
0.8369	Intermediate Similarity	NPC477696
0.8367	Intermediate Similarity	NPC287504

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 NPC469480 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	824
0.2-0.3	1726
0.3-0.4	2630
0.4-0.5	1838
0.5-0.6	1025
0.6-0.7	687
0.7-0.8	140
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
0.8358	Intermediate Similarity	NPD3027	Phase 3
0.8306	Intermediate Similarity	NPD228	Approved
0.8299	Intermediate Similarity	NPD1934	Approved
0.8182	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD9494	Approved
0.8	Intermediate Similarity	NPD2801	Approved
0.7914	Intermediate Similarity	NPD1613	Approved
0.7914	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3882	Suspended
0.7885	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6166	Phase 2
0.7877	Intermediate Similarity	NPD1511	Approved
0.7793	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4110	Phase 3
0.7792	Intermediate Similarity	NPD6234	Discontinued
0.777	Intermediate Similarity	NPD1512	Approved
0.7755	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD5283	Phase 1
0.773	Intermediate Similarity	NPD230	Phase 1
0.7688	Intermediate Similarity	NPD7074	Phase 3
0.7681	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3818	Discontinued
0.7652	Intermediate Similarity	NPD5536	Phase 2
0.763	Intermediate Similarity	NPD3705	Approved
0.7625	Intermediate Similarity	NPD7054	Approved
0.7609	Intermediate Similarity	NPD5647	Approved
0.7606	Intermediate Similarity	NPD6355	Discontinued
0.7606	Intermediate Similarity	NPD447	Suspended
0.7597	Intermediate Similarity	NPD3817	Phase 2
0.7582	Intermediate Similarity	NPD37	Approved
0.7578	Intermediate Similarity	NPD7472	Approved
0.7574	Intermediate Similarity	NPD1608	Approved
0.7566	Intermediate Similarity	NPD4380	Phase 2
0.7551	Intermediate Similarity	NPD4628	Phase 3
0.7548	Intermediate Similarity	NPD4965	Approved
0.7548	Intermediate Similarity	NPD4966	Approved
0.7548	Intermediate Similarity	NPD4967	Phase 2
0.7548	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD1357	Approved
0.7535	Intermediate Similarity	NPD3620	Phase 2
0.7535	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD2684	Approved
0.75	Intermediate Similarity	NPD6190	Approved
0.7466	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6233	Phase 2
0.7453	Intermediate Similarity	NPD7228	Approved
0.7448	Intermediate Similarity	NPD1510	Phase 2
0.7442	Intermediate Similarity	NPD3022	Approved
0.7442	Intermediate Similarity	NPD3021	Approved
0.7432	Intermediate Similarity	NPD8166	Discontinued
0.7431	Intermediate Similarity	NPD6653	Approved
0.7429	Intermediate Similarity	NPD2861	Phase 2
0.7423	Intermediate Similarity	NPD6797	Phase 2
0.7415	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1549	Phase 2
0.7413	Intermediate Similarity	NPD4060	Phase 1
0.7413	Intermediate Similarity	NPD826	Approved
0.7413	Intermediate Similarity	NPD1240	Approved
0.7413	Intermediate Similarity	NPD825	Approved
0.7413	Intermediate Similarity	NPD1558	Phase 1
0.7407	Intermediate Similarity	NPD1651	Approved
0.7405	Intermediate Similarity	NPD5494	Approved
0.7405	Intermediate Similarity	NPD7843	Approved
0.7397	Intermediate Similarity	NPD2935	Discontinued
0.7391	Intermediate Similarity	NPD7473	Discontinued
0.7378	Intermediate Similarity	NPD7251	Discontinued
0.7368	Intermediate Similarity	NPD7157	Approved
0.7353	Intermediate Similarity	NPD17	Approved
0.7353	Intermediate Similarity	NPD1778	Approved
0.7351	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1241	Discontinued
0.7347	Intermediate Similarity	NPD7266	Discontinued
0.7343	Intermediate Similarity	NPD4062	Phase 3
0.7338	Intermediate Similarity	NPD1283	Approved
0.7333	Intermediate Similarity	NPD9545	Approved
0.7333	Intermediate Similarity	NPD7808	Phase 3
0.7333	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3686	Approved
0.732	Intermediate Similarity	NPD3687	Approved
0.732	Intermediate Similarity	NPD1653	Approved
0.7312	Intermediate Similarity	NPD6232	Discontinued
0.731	Intermediate Similarity	NPD1607	Approved
0.7305	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD943	Approved
0.7279	Intermediate Similarity	NPD9570	Approved
0.7278	Intermediate Similarity	NPD7075	Discontinued
0.7278	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8127	Discontinued
0.725	Intermediate Similarity	NPD7199	Phase 2
0.7246	Intermediate Similarity	NPD1535	Discovery
0.7237	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3146	Approved
0.723	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1375	Discontinued
0.723	Intermediate Similarity	NPD6005	Phase 3
0.723	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6004	Phase 3
0.723	Intermediate Similarity	NPD6002	Phase 3
0.7222	Intermediate Similarity	NPD2674	Phase 3
0.7211	Intermediate Similarity	NPD7033	Discontinued
0.7203	Intermediate Similarity	NPD7095	Approved
0.7197	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1481	Phase 2
0.7172	Intermediate Similarity	NPD2979	Phase 3
0.7171	Intermediate Similarity	NPD6799	Approved
0.7169	Intermediate Similarity	NPD7685	Pre-registration
0.7162	Intermediate Similarity	NPD2796	Approved
0.7162	Intermediate Similarity	NPD2438	Suspended
0.7162	Intermediate Similarity	NPD6100	Approved
0.7162	Intermediate Similarity	NPD6099	Approved
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD290	Approved
0.7154	Intermediate Similarity	NPD1358	Approved
0.7153	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3145	Approved
0.7153	Intermediate Similarity	NPD3144	Approved
0.7152	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2983	Phase 2
0.7143	Intermediate Similarity	NPD2982	Phase 2
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4237	Approved
0.7133	Intermediate Similarity	NPD3060	Approved
0.7133	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4908	Phase 1
0.7133	Intermediate Similarity	NPD4236	Phase 3
0.7124	Intermediate Similarity	NPD2532	Approved
0.7124	Intermediate Similarity	NPD2534	Approved
0.7124	Intermediate Similarity	NPD2533	Approved
0.7123	Intermediate Similarity	NPD555	Phase 2
0.7122	Intermediate Similarity	NPD1281	Approved
0.7122	Intermediate Similarity	NPD1610	Phase 2
0.7122	Intermediate Similarity	NPD1091	Approved
0.7115	Intermediate Similarity	NPD7028	Phase 2
0.7113	Intermediate Similarity	NPD257	Approved
0.7113	Intermediate Similarity	NPD258	Approved
0.7111	Intermediate Similarity	NPD6671	Approved
0.7108	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9296	Approved
0.7095	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2799	Discontinued
0.7091	Intermediate Similarity	NPD5844	Phase 1
0.7089	Intermediate Similarity	NPD1465	Phase 2
0.708	Intermediate Similarity	NPD1894	Discontinued
0.7071	Intermediate Similarity	NPD2981	Phase 2
0.707	Intermediate Similarity	NPD6385	Approved
0.707	Intermediate Similarity	NPD6386	Approved
0.7067	Intermediate Similarity	NPD5958	Discontinued
0.7067	Intermediate Similarity	NPD4534	Discontinued
0.7067	Intermediate Similarity	NPD2424	Discontinued
0.7066	Intermediate Similarity	NPD6559	Discontinued
0.7063	Intermediate Similarity	NPD3018	Phase 2
0.7051	Intermediate Similarity	NPD3455	Phase 2
0.705	Intermediate Similarity	NPD3496	Discontinued
0.705	Intermediate Similarity	NPD3847	Discontinued
0.7047	Intermediate Similarity	NPD2161	Phase 2
0.7047	Intermediate Similarity	NPD5712	Approved
0.7044	Intermediate Similarity	NPD5402	Approved
0.7037	Intermediate Similarity	NPD1247	Approved
0.7034	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD291	Approved
0.7029	Intermediate Similarity	NPD5585	Approved
0.7027	Intermediate Similarity	NPD7097	Phase 1
0.7025	Intermediate Similarity	NPD6801	Discontinued
0.7021	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6674	Discontinued
0.7019	Intermediate Similarity	NPD919	Approved
0.7013	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6599	Discontinued
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5763	Approved
0.7	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3787	Discontinued
0.6993	Remote Similarity	NPD2798	Approved
0.6988	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD259	Phase 1
0.6981	Remote Similarity	NPD7819	Suspended
0.6978	Remote Similarity	NPD3019	Approved
0.6978	Remote Similarity	NPD4626	Approved
0.6978	Remote Similarity	NPD9381	Approved
0.6978	Remote Similarity	NPD9384	Approved
0.6978	Remote Similarity	NPD2932	Approved
0.6974	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD8651	Approved
0.6964	Remote Similarity	NPD7240	Approved
0.6957	Remote Similarity	NPD1548	Phase 1
0.695	Remote Similarity	NPD9269	Phase 2
0.695	Remote Similarity	NPD9717	Approved
0.6948	Remote Similarity	NPD4357	Discontinued
0.6947	Remote Similarity	NPD968	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