NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.12
Volume:	249.463
LogP:	1.514
LogD:	1.629
LogS:	-1.732
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.855
Synthetic Accessibility Score:	3.112
Fsp3:	0.462
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:	-4.481
MDCK Permeability:	1.569048072269652e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.25
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.704
Plasma Protein Binding (PPB):	70.8713150024414%
Volume Distribution (VD):	0.68
Pgp-substrate:	16.898317337036133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.686
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.081
CYP3A4-substrate:	0.582

ADMET: Excretion

Clearance (CL):	15.47
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.596
Drug-inuced Liver Injury (DILI):	0.617
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.043
Skin Sensitization:	0.652
Carcinogencity:	0.088
Eye Corrosion:	0.79
Eye Irritation:	0.908
Respiratory Toxicity:	0.187

Download Data

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

Natural Product: NPC142985

Natural Product ID:	NPC142985
*Common Name:**	(3R,4S)-4-(4-Hydroxy-3-Methoxyphenyl)-4-Methoxy-3-Methylbutan-2-One
IUPAC Name:	(3R,4S)-4-(4-hydroxy-3-methoxyphenyl)-4-methoxy-3-methylbutan-2-one
Synonyms:
Standard InCHIKey:	WLUGKAVAULDYKC-SDBXPKJASA-N
Standard InCHI:	InChI=1S/C13H18O4/c1-8(9(2)14)13(17-4)10-5-6-11(15)12(7-10)16-3/h5-8,13,15H,1-4H3/t8-,13-/m0/s1
SMILES:	C[C@@H](C(=O)C)[C@@H](c1ccc(c(c1)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1075663
PubChem CID:	44613168
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	=	67.0	%	PMID[524157]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	47.0	%	PMID[524157]

☑ 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 NPC142985 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	310
0.1-0.2	1291
0.2-0.3	3612
0.3-0.4	9351
0.4-0.5	9397
0.5-0.6	3772
0.6-0.7	7975
0.7-0.8	6229
0.8-0.85	651
0.85-0.9	78
0.9-0.95	28
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC469480
0.9839	High Similarity	NPC195292
0.944	High Similarity	NPC12022
0.944	High Similarity	NPC20287
0.944	High Similarity	NPC293641
0.944	High Similarity	NPC20404
0.9365	High Similarity	NPC278308
0.9308	High Similarity	NPC470990
0.9219	High Similarity	NPC137427
0.9219	High Similarity	NPC244246
0.9219	High Similarity	NPC311419
0.9219	High Similarity	NPC215941
0.9219	High Similarity	NPC123196
0.9219	High Similarity	NPC319282
0.9219	High Similarity	NPC275724
0.9219	High Similarity	NPC65935
0.912	High Similarity	NPC163083
0.912	High Similarity	NPC244876
0.9113	High Similarity	NPC201777
0.903	High Similarity	NPC474784
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
0.896	High Similarity	NPC476343
0.8906	High Similarity	NPC92207
0.8906	High Similarity	NPC127937
0.8889	High Similarity	NPC114298
0.8889	High Similarity	NPC147379
0.8872	High Similarity	NPC152209
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
0.8841	High Similarity	NPC223185
0.8837	High Similarity	NPC281020
0.8828	High Similarity	NPC280767
0.8819	High Similarity	NPC242372
0.8819	High Similarity	NPC164778
0.8819	High Similarity	NPC4181
0.8819	High Similarity	NPC257976
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
0.8786	High Similarity	NPC1580
0.8769	High Similarity	NPC226661
0.8768	High Similarity	NPC239608
0.8768	High Similarity	NPC27159
0.8768	High Similarity	NPC46161
0.876	High Similarity	NPC84076
0.876	High Similarity	NPC90128
0.876	High Similarity	NPC303680
0.875	High Similarity	NPC203351
0.875	High Similarity	NPC312404
0.875	High Similarity	NPC273686
0.873	High Similarity	NPC158949
0.872	High Similarity	NPC135961
0.8714	High Similarity	NPC472333
0.8714	High Similarity	NPC208507
0.8702	High Similarity	NPC304622
0.8692	High Similarity	NPC123228
0.8692	High Similarity	NPC118533
0.8692	High Similarity	NPC123722
0.8692	High Similarity	NPC276466
0.8692	High Similarity	NPC5018
0.8692	High Similarity	NPC165045
0.8692	High Similarity	NPC151167
0.8686	High Similarity	NPC100675
0.8682	High Similarity	NPC148627
0.8672	High Similarity	NPC471693
0.8647	High Similarity	NPC239302
0.8647	High Similarity	NPC50763
0.8636	High Similarity	NPC172673
0.8629	High Similarity	NPC221049
0.8626	High Similarity	NPC45774
0.8626	High Similarity	NPC282703
0.8626	High Similarity	NPC11258
0.8626	High Similarity	NPC21867
0.8626	High Similarity	NPC129570
0.8626	High Similarity	NPC128208
0.8626	High Similarity	NPC184733
0.8615	High Similarity	NPC179777
0.8603	High Similarity	NPC281780
0.8594	High Similarity	NPC209567
0.8593	High Similarity	NPC113295
0.8593	High Similarity	NPC139519
0.8583	High Similarity	NPC98305
0.8571	High Similarity	NPC311595
0.8571	High Similarity	NPC24474
0.856	High Similarity	NPC164386
0.8551	High Similarity	NPC19158
0.855	High Similarity	NPC5428
0.8538	High Similarity	NPC3221
0.8527	High Similarity	NPC165375
0.8527	High Similarity	NPC220598
0.8519	High Similarity	NPC68779
0.8519	High Similarity	NPC300776
0.8519	High Similarity	NPC67247
0.8519	High Similarity	NPC176814
0.8519	High Similarity	NPC4982
0.8519	High Similarity	NPC471110
0.8519	High Similarity	NPC5310
0.8511	High Similarity	NPC474799
0.85	High Similarity	NPC469615
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
0.8489	Intermediate Similarity	NPC472335
0.8489	Intermediate Similarity	NPC253722
0.8489	Intermediate Similarity	NPC253481
0.8489	Intermediate Similarity	NPC472332
0.8489	Intermediate Similarity	NPC31751
0.8485	Intermediate Similarity	NPC474178
0.8485	Intermediate Similarity	NPC252307
0.8485	Intermediate Similarity	NPC245826
0.8483	Intermediate Similarity	NPC327225
0.8478	Intermediate Similarity	NPC289690
0.8478	Intermediate Similarity	NPC4796
0.8478	Intermediate Similarity	NPC288452
0.8473	Intermediate Similarity	NPC58607
0.8473	Intermediate Similarity	NPC191037
0.8473	Intermediate Similarity	NPC178284
0.8462	Intermediate Similarity	NPC474903
0.8462	Intermediate Similarity	NPC125570
0.8451	Intermediate Similarity	NPC283081
0.8451	Intermediate Similarity	NPC30720
0.8451	Intermediate Similarity	NPC221383
0.8451	Intermediate Similarity	NPC143892
0.8451	Intermediate Similarity	NPC299090
0.845	Intermediate Similarity	NPC85488
0.8444	Intermediate Similarity	NPC283823
0.8444	Intermediate Similarity	NPC475468
0.8444	Intermediate Similarity	NPC159418
0.844	Intermediate Similarity	NPC474982
0.844	Intermediate Similarity	NPC469683
0.8438	Intermediate Similarity	NPC207613
0.8433	Intermediate Similarity	NPC161557
0.8433	Intermediate Similarity	NPC158079
0.8433	Intermediate Similarity	NPC228346
0.8433	Intermediate Similarity	NPC27843
0.8433	Intermediate Similarity	NPC40432
0.8433	Intermediate Similarity	NPC7171
0.8433	Intermediate Similarity	NPC277804
0.8433	Intermediate Similarity	NPC115207
0.8433	Intermediate Similarity	NPC474017
0.8429	Intermediate Similarity	NPC106920
0.8429	Intermediate Similarity	NPC273657
0.8429	Intermediate Similarity	NPC285550
0.8425	Intermediate Similarity	NPC25127
0.8421	Intermediate Similarity	NPC170844
0.8421	Intermediate Similarity	NPC475875
0.8421	Intermediate Similarity	NPC476968
0.8421	Intermediate Similarity	NPC241354
0.8413	Intermediate Similarity	NPC293619
0.8409	Intermediate Similarity	NPC292056
0.8409	Intermediate Similarity	NPC16651
0.8409	Intermediate Similarity	NPC319625
0.8409	Intermediate Similarity	NPC118787
0.8409	Intermediate Similarity	NPC183181
0.8409	Intermediate Similarity	NPC32163
0.8409	Intermediate Similarity	NPC147821
0.8409	Intermediate Similarity	NPC111247
0.8409	Intermediate Similarity	NPC41706
0.8409	Intermediate Similarity	NPC163332
0.8397	Intermediate Similarity	NPC194519
0.8397	Intermediate Similarity	NPC173608
0.8394	Intermediate Similarity	NPC90431
0.8394	Intermediate Similarity	NPC471988
0.8392	Intermediate Similarity	NPC98009
0.8385	Intermediate Similarity	NPC280704
0.8382	Intermediate Similarity	NPC37065
0.8382	Intermediate Similarity	NPC106406
0.838	Intermediate Similarity	NPC30890
0.8374	Intermediate Similarity	NPC8547
0.8374	Intermediate Similarity	NPC257124
0.8374	Intermediate Similarity	NPC156840
0.8374	Intermediate Similarity	NPC173746
0.8372	Intermediate Similarity	NPC49341
0.8372	Intermediate Similarity	NPC324571
0.8372	Intermediate Similarity	NPC54872
0.8372	Intermediate Similarity	NPC343720
0.8372	Intermediate Similarity	NPC184651
0.8372	Intermediate Similarity	NPC113865
0.8372	Intermediate Similarity	NPC473853

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 NPC142985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	843
0.2-0.3	1748
0.3-0.4	2666
0.4-0.5	1797
0.5-0.6	1032
0.6-0.7	660
0.7-0.8	110
0.8-0.85	6
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)
0.8231	Intermediate Similarity	NPD1934	Approved
0.8134	Intermediate Similarity	NPD9494	Approved
0.8054	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2801	Approved
0.7842	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1613	Approved
0.7829	Intermediate Similarity	NPD3882	Suspended
0.7821	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6166	Phase 2
0.7812	Intermediate Similarity	NPD5283	Phase 1
0.7808	Intermediate Similarity	NPD1511	Approved
0.7727	Intermediate Similarity	NPD6234	Discontinued
0.7724	Intermediate Similarity	NPD4110	Phase 3
0.7724	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD5536	Phase 2
0.7703	Intermediate Similarity	NPD1512	Approved
0.7687	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD230	Phase 1
0.7632	Intermediate Similarity	NPD37	Approved
0.7625	Intermediate Similarity	NPD7074	Phase 3
0.761	Intermediate Similarity	NPD3818	Discontinued
0.7609	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1357	Approved
0.7589	Intermediate Similarity	NPD3620	Phase 2
0.7589	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7054	Approved
0.7556	Intermediate Similarity	NPD3705	Approved
0.7536	Intermediate Similarity	NPD5647	Approved
0.7535	Intermediate Similarity	NPD447	Suspended
0.7535	Intermediate Similarity	NPD6355	Discontinued
0.7532	Intermediate Similarity	NPD3817	Phase 2
0.7516	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD1510	Phase 2
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	NPD4967	Phase 2
0.7484	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4966	Approved
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7465	Intermediate Similarity	NPD1240	Approved
0.7463	Intermediate Similarity	NPD1651	Approved
0.7448	Intermediate Similarity	NPD2935	Discontinued
0.7447	Intermediate Similarity	NPD6798	Discontinued
0.7438	Intermediate Similarity	NPD7473	Discontinued
0.7432	Intermediate Similarity	NPD6190	Approved
0.7422	Intermediate Similarity	NPD2684	Approved
0.7397	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6233	Phase 2
0.7391	Intermediate Similarity	NPD1283	Approved
0.7391	Intermediate Similarity	NPD7228	Approved
0.7365	Intermediate Similarity	NPD8166	Discontinued
0.7362	Intermediate Similarity	NPD6797	Phase 2
0.7361	Intermediate Similarity	NPD6653	Approved
0.7361	Intermediate Similarity	NPD1607	Approved
0.7358	Intermediate Similarity	NPD6232	Discontinued
0.7357	Intermediate Similarity	NPD2861	Phase 2
0.7347	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1549	Phase 2
0.7343	Intermediate Similarity	NPD826	Approved
0.7343	Intermediate Similarity	NPD825	Approved
0.7343	Intermediate Similarity	NPD4060	Phase 1
0.7343	Intermediate Similarity	NPD1558	Phase 1
0.7343	Intermediate Similarity	NPD943	Approved
0.7342	Intermediate Similarity	NPD5494	Approved
0.7329	Intermediate Similarity	NPD9570	Approved
0.7328	Intermediate Similarity	NPD7843	Approved
0.7317	Intermediate Similarity	NPD7251	Discontinued
0.7293	Intermediate Similarity	NPD7157	Approved
0.7285	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7266	Discontinued
0.7279	Intermediate Similarity	NPD17	Approved
0.7279	Intermediate Similarity	NPD1778	Approved
0.7273	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD4062	Phase 3
0.7273	Intermediate Similarity	NPD1241	Discontinued
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2674	Phase 3
0.7259	Intermediate Similarity	NPD9545	Approved
0.7255	Intermediate Similarity	NPD3686	Approved
0.7255	Intermediate Similarity	NPD3687	Approved
0.7255	Intermediate Similarity	NPD1653	Approved
0.7246	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7075	Discontinued
0.7203	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3144	Approved
0.7203	Intermediate Similarity	NPD3145	Approved
0.7194	Intermediate Similarity	NPD2983	Phase 2
0.7194	Intermediate Similarity	NPD2982	Phase 2
0.719	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8127	Discontinued
0.7188	Intermediate Similarity	NPD7199	Phase 2
0.7181	Intermediate Similarity	NPD3060	Approved
0.7174	Intermediate Similarity	NPD1281	Approved
0.7174	Intermediate Similarity	NPD1535	Discovery
0.7171	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3146	Approved
0.7163	Intermediate Similarity	NPD258	Approved
0.7163	Intermediate Similarity	NPD257	Approved
0.7162	Intermediate Similarity	NPD1375	Discontinued
0.7162	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6004	Phase 3
0.7162	Intermediate Similarity	NPD6002	Phase 3
0.7162	Intermediate Similarity	NPD6005	Phase 3
0.7162	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7028	Phase 2
0.7154	Intermediate Similarity	NPD9296	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7095	Approved
0.7122	Intermediate Similarity	NPD1481	Phase 2
0.7122	Intermediate Similarity	NPD2981	Phase 2
0.7113	Intermediate Similarity	NPD3018	Phase 2
0.7108	Intermediate Similarity	NPD7685	Pre-registration
0.7105	Intermediate Similarity	NPD6799	Approved
0.7103	Intermediate Similarity	NPD2979	Phase 3
0.7101	Intermediate Similarity	NPD3847	Discontinued
0.7099	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6100	Approved
0.7095	Intermediate Similarity	NPD2438	Suspended
0.7095	Intermediate Similarity	NPD2796	Approved
0.7095	Intermediate Similarity	NPD6099	Approved
0.7089	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD290	Approved
0.7077	Intermediate Similarity	NPD1358	Approved
0.7071	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4236	Phase 3
0.7067	Intermediate Similarity	NPD4237	Approved
0.7063	Intermediate Similarity	NPD4908	Phase 1
0.7059	Intermediate Similarity	NPD2532	Approved
0.7059	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD2533	Approved
0.7059	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD555	Phase 2
0.705	Intermediate Similarity	NPD1610	Phase 2
0.705	Intermediate Similarity	NPD1091	Approved
0.7048	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
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	NPD9381	Approved
0.7029	Intermediate Similarity	NPD9384	Approved
0.7029	Intermediate Similarity	NPD4626	Approved
0.7029	Intermediate Similarity	NPD3019	Approved
0.7027	Intermediate Similarity	NPD2799	Discontinued
0.7025	Intermediate Similarity	NPD1465	Phase 2
0.702	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1894	Discontinued
0.7006	Intermediate Similarity	NPD6385	Approved
0.7006	Intermediate Similarity	NPD6559	Discontinued
0.7006	Intermediate Similarity	NPD6386	Approved
0.7	Intermediate Similarity	NPD5958	Discontinued
0.7	Intermediate Similarity	NPD4534	Discontinued
0.7	Intermediate Similarity	NPD9269	Phase 2
0.7	Intermediate Similarity	NPD2424	Discontinued
0.6993	Remote Similarity	NPD4357	Discontinued
0.6987	Remote Similarity	NPD3455	Phase 2
0.6987	Remote Similarity	NPD824	Approved
0.6981	Remote Similarity	NPD5402	Approved
0.698	Remote Similarity	NPD2161	Phase 2
0.698	Remote Similarity	NPD5712	Approved
0.6978	Remote Similarity	NPD3496	Discontinued
0.6975	Remote Similarity	NPD1247	Approved
0.6974	Remote Similarity	NPD2219	Phase 1
0.6966	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6801	Discontinued
0.6959	Remote Similarity	NPD7097	Phase 1
0.6957	Remote Similarity	NPD5585	Approved
0.6957	Remote Similarity	NPD919	Approved
0.6954	Remote Similarity	NPD6674	Discontinued
0.6953	Remote Similarity	NPD291	Approved
0.695	Remote Similarity	NPD9622	Approved
0.6948	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6599	Discontinued
0.6933	Remote Similarity	NPD3787	Discontinued
0.6933	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5763	Approved
0.6933	Remote Similarity	NPD5762	Approved
0.6929	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2977	Approved
0.6918	Remote Similarity	NPD7819	Suspended
0.6918	Remote Similarity	NPD2978	Approved
0.6917	Remote Similarity	NPD9280	Clinical (unspecified phase)

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