NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.08
Volume:	197.524
LogP:	1.758
LogD:	1.387
LogS:	-1.961
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	3.281
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.529
MDCK Permeability:	1.9206752767786384e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.71

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	86.02323913574219%
Volume Distribution (VD):	1.707
Pgp-substrate:	13.342327117919922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.58
CYP1A2-substrate:	0.588
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.512
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.185
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.746
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	14.388
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.747
Maximum Recommended Daily Dose:	0.435
Skin Sensitization:	0.917
Carcinogencity:	0.743
Eye Corrosion:	0.026
Eye Irritation:	0.672
Respiratory Toxicity:	0.879

Download Data

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

Natural Product: NPC154256

Natural Product ID:	NPC154256
*Common Name:**	(2S)-2-(Hydroxymethyl)-2-Methylchromen-6-Ol
IUPAC Name:	(2S)-2-(hydroxymethyl)-2-methylchromen-6-ol
Synonyms:
Standard InCHIKey:	LTKJWSBGTNWRNP-NSHDSACASA-N
Standard InCHI:	InChI=1S/C11H12O3/c1-11(7-12)5-4-8-6-9(13)2-3-10(8)14-11/h2-6,12-13H,7H2,1H3/t11-/m0/s1
SMILES:	OC[C@]1(C)C=Cc2c(O1)ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL232615
PubChem CID:	44431346
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

*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
NPO21659	Daedalea quercina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11014261]
NPO21268	Heliotropium ramosissimum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21268	Heliotropium ramosissimum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22868	Pulsatilla dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21659	Daedalea quercina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22868	Pulsatilla dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13371	Paepalanthus ramosus	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20036	Mallotus pallidus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18205	Brevibacterium iodinum	Species	Brevibacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20918	Pseudotsuga menziesii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20795	Melicope melanophloia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21268	Heliotropium ramosissimum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25850	Urochloa ruziziensis	Species	Poaceae	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	5

Activity Type	# Activity
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	4700.0	nM	PMID[514878]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	630.0	nM	PMID[514878]
NPT4734	Individual Protein	Dehydrogenase/reductase SDR family member 9	Homo sapiens	IC50	=	114000.0	nM	PMID[514878]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	21000.0	nM	PMID[514878]
NPT2	Others	Unspecified		IC50	=	68000.0	nM	PMID[514878]

☑ 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 NPC154256 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	319
0.1-0.2	1623
0.2-0.3	5665
0.3-0.4	13284
0.4-0.5	4303
0.5-0.6	6365
0.6-0.7	8636
0.7-0.8	2276
0.8-0.85	195
0.85-0.9	17
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC290470
0.9386	High Similarity	NPC473875
0.9273	High Similarity	NPC474920
0.9052	High Similarity	NPC475529
0.9027	High Similarity	NPC301321
0.9027	High Similarity	NPC473718
0.8983	High Similarity	NPC474130
0.8957	High Similarity	NPC283616
0.8909	High Similarity	NPC241549
0.8898	High Similarity	NPC204535
0.8898	High Similarity	NPC46586
0.8879	High Similarity	NPC32152
0.8818	High Similarity	NPC233320
0.8818	High Similarity	NPC194034
0.8814	High Similarity	NPC476165
0.8803	High Similarity	NPC474131
0.8803	High Similarity	NPC232295
0.8718	High Similarity	NPC471449
0.8621	High Similarity	NPC69539
0.8559	High Similarity	NPC51341
0.8548	High Similarity	NPC97326
0.8547	High Similarity	NPC187993
0.8547	High Similarity	NPC238176
0.8545	High Similarity	NPC130817
0.8509	High Similarity	NPC275627
0.8509	High Similarity	NPC195873
0.85	High Similarity	NPC212965
0.8487	Intermediate Similarity	NPC14177
0.8468	Intermediate Similarity	NPC40377
0.8462	Intermediate Similarity	NPC163398
0.8455	Intermediate Similarity	NPC476006
0.8448	Intermediate Similarity	NPC470837
0.8448	Intermediate Similarity	NPC161696
0.843	Intermediate Similarity	NPC120638
0.8421	Intermediate Similarity	NPC46844
0.8417	Intermediate Similarity	NPC96423
0.8413	Intermediate Similarity	NPC82503
0.8407	Intermediate Similarity	NPC169450
0.8374	Intermediate Similarity	NPC476254
0.8374	Intermediate Similarity	NPC131397
0.8361	Intermediate Similarity	NPC261992
0.8348	Intermediate Similarity	NPC55300
0.8348	Intermediate Similarity	NPC139617
0.8348	Intermediate Similarity	NPC78918
0.832	Intermediate Similarity	NPC19694
0.8319	Intermediate Similarity	NPC329980
0.8293	Intermediate Similarity	NPC190086
0.8293	Intermediate Similarity	NPC74478
0.8293	Intermediate Similarity	NPC147896
0.8293	Intermediate Similarity	NPC276962
0.8291	Intermediate Similarity	NPC87563
0.8279	Intermediate Similarity	NPC188997
0.8279	Intermediate Similarity	NPC302211
0.8276	Intermediate Similarity	NPC98372
0.8276	Intermediate Similarity	NPC165646
0.8264	Intermediate Similarity	NPC45663
0.825	Intermediate Similarity	NPC85895
0.825	Intermediate Similarity	NPC163036
0.825	Intermediate Similarity	NPC137294
0.824	Intermediate Similarity	NPC216836
0.8217	Intermediate Similarity	NPC106215
0.8214	Intermediate Similarity	NPC108875
0.8214	Intermediate Similarity	NPC474603
0.8214	Intermediate Similarity	NPC38079
0.8214	Intermediate Similarity	NPC12987
0.8211	Intermediate Similarity	NPC248786
0.8198	Intermediate Similarity	NPC51633
0.8197	Intermediate Similarity	NPC48623
0.8197	Intermediate Similarity	NPC290451
0.8197	Intermediate Similarity	NPC168707
0.8197	Intermediate Similarity	NPC127389
0.819	Intermediate Similarity	NPC266932
0.819	Intermediate Similarity	NPC156840
0.819	Intermediate Similarity	NPC8547
0.819	Intermediate Similarity	NPC173746
0.819	Intermediate Similarity	NPC257124
0.8189	Intermediate Similarity	NPC220935
0.8189	Intermediate Similarity	NPC475880
0.8175	Intermediate Similarity	NPC63179
0.8174	Intermediate Similarity	NPC473524
0.8174	Intermediate Similarity	NPC36108
0.8174	Intermediate Similarity	NPC246358
0.8174	Intermediate Similarity	NPC233731
0.8174	Intermediate Similarity	NPC7097
0.8167	Intermediate Similarity	NPC212743
0.816	Intermediate Similarity	NPC58607
0.816	Intermediate Similarity	NPC178284
0.816	Intermediate Similarity	NPC191037
0.8158	Intermediate Similarity	NPC227894
0.8154	Intermediate Similarity	NPC472337
0.8151	Intermediate Similarity	NPC221049
0.8145	Intermediate Similarity	NPC293701
0.8145	Intermediate Similarity	NPC48990
0.8145	Intermediate Similarity	NPC114901
0.8145	Intermediate Similarity	NPC61685
0.8145	Intermediate Similarity	NPC109822
0.8145	Intermediate Similarity	NPC94276
0.8145	Intermediate Similarity	NPC248557
0.8142	Intermediate Similarity	NPC8302
0.8142	Intermediate Similarity	NPC470393
0.813	Intermediate Similarity	NPC194626
0.8125	Intermediate Similarity	NPC192596
0.8125	Intermediate Similarity	NPC153019
0.8115	Intermediate Similarity	NPC307253
0.8115	Intermediate Similarity	NPC218753
0.811	Intermediate Similarity	NPC45824
0.811	Intermediate Similarity	NPC59654
0.811	Intermediate Similarity	NPC271832
0.811	Intermediate Similarity	NPC158477
0.8108	Intermediate Similarity	NPC130103
0.8103	Intermediate Similarity	NPC137685
0.8099	Intermediate Similarity	NPC320987
0.8099	Intermediate Similarity	NPC181969
0.8095	Intermediate Similarity	NPC319625
0.8095	Intermediate Similarity	NPC183181
0.8095	Intermediate Similarity	NPC111247
0.8095	Intermediate Similarity	NPC163332
0.8095	Intermediate Similarity	NPC118787
0.8095	Intermediate Similarity	NPC50368
0.8095	Intermediate Similarity	NPC95034
0.8095	Intermediate Similarity	NPC142087
0.8095	Intermediate Similarity	NPC292056
0.8095	Intermediate Similarity	NPC41706
0.8095	Intermediate Similarity	NPC147821
0.8092	Intermediate Similarity	NPC472336
0.8092	Intermediate Similarity	NPC475628
0.8092	Intermediate Similarity	NPC472334
0.8091	Intermediate Similarity	NPC88420
0.8091	Intermediate Similarity	NPC475078
0.8087	Intermediate Similarity	NPC75440
0.8083	Intermediate Similarity	NPC164386
0.8083	Intermediate Similarity	NPC86947
0.808	Intermediate Similarity	NPC194519
0.8062	Intermediate Similarity	NPC161203
0.8062	Intermediate Similarity	NPC329427
0.8062	Intermediate Similarity	NPC317601
0.8056	Intermediate Similarity	NPC29373
0.8051	Intermediate Similarity	NPC301735
0.8049	Intermediate Similarity	NPC226712
0.8049	Intermediate Similarity	NPC285289
0.8049	Intermediate Similarity	NPC470804
0.8047	Intermediate Similarity	NPC229231
0.8047	Intermediate Similarity	NPC214860
0.8047	Intermediate Similarity	NPC11089
0.8033	Intermediate Similarity	NPC35071
0.8033	Intermediate Similarity	NPC148615
0.8033	Intermediate Similarity	NPC177475
0.8018	Intermediate Similarity	NPC100870
0.8017	Intermediate Similarity	NPC139047
0.8017	Intermediate Similarity	NPC255675
0.8015	Intermediate Similarity	NPC476018
0.8015	Intermediate Similarity	NPC327382
0.8015	Intermediate Similarity	NPC475029
0.8015	Intermediate Similarity	NPC134968
0.8	Intermediate Similarity	NPC258171
0.8	Intermediate Similarity	NPC183446
0.8	Intermediate Similarity	NPC229442
0.8	Intermediate Similarity	NPC474352
0.8	Intermediate Similarity	NPC94236
0.8	Intermediate Similarity	NPC211352
0.8	Intermediate Similarity	NPC474237
0.8	Intermediate Similarity	NPC251306
0.8	Intermediate Similarity	NPC270030
0.8	Intermediate Similarity	NPC168059
0.8	Intermediate Similarity	NPC37196
0.7984	Intermediate Similarity	NPC166168
0.7984	Intermediate Similarity	NPC135414
0.7984	Intermediate Similarity	NPC270326
0.7984	Intermediate Similarity	NPC474143
0.7984	Intermediate Similarity	NPC209567
0.7984	Intermediate Similarity	NPC85488
0.7984	Intermediate Similarity	NPC474246
0.7984	Intermediate Similarity	NPC74137
0.7984	Intermediate Similarity	NPC474864
0.7984	Intermediate Similarity	NPC246967
0.7984	Intermediate Similarity	NPC71090
0.797	Intermediate Similarity	NPC13067
0.797	Intermediate Similarity	NPC19869
0.7969	Intermediate Similarity	NPC5851
0.7969	Intermediate Similarity	NPC86030
0.7969	Intermediate Similarity	NPC210655
0.7967	Intermediate Similarity	NPC207613
0.7967	Intermediate Similarity	NPC100108
0.7967	Intermediate Similarity	NPC277798
0.7967	Intermediate Similarity	NPC129176
0.7967	Intermediate Similarity	NPC212559
0.7966	Intermediate Similarity	NPC115379
0.7966	Intermediate Similarity	NPC228452
0.7965	Intermediate Similarity	NPC305205
0.7955	Intermediate Similarity	NPC104167
0.7955	Intermediate Similarity	NPC476698
0.7953	Intermediate Similarity	NPC473993
0.7953	Intermediate Similarity	NPC469386
0.7951	Intermediate Similarity	NPC24474
0.7951	Intermediate Similarity	NPC311595
0.7951	Intermediate Similarity	NPC135961
0.7946	Intermediate Similarity	NPC174911
0.7939	Intermediate Similarity	NPC310854
0.7937	Intermediate Similarity	NPC278552
0.7937	Intermediate Similarity	NPC470510

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 NPC154256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	975
0.2-0.3	1820
0.3-0.4	2714
0.4-0.5	1565
0.5-0.6	1043
0.6-0.7	617
0.7-0.8	110
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.886	High Similarity	NPD6671	Approved
0.8818	High Similarity	NPD290	Approved
0.8727	High Similarity	NPD968	Approved
0.8246	Intermediate Similarity	NPD2684	Approved
0.819	Intermediate Similarity	NPD228	Approved
0.8115	Intermediate Similarity	NPD3496	Discontinued
0.8049	Intermediate Similarity	NPD1091	Approved
0.7966	Intermediate Similarity	NPD7843	Approved
0.7953	Intermediate Similarity	NPD2861	Phase 2
0.7923	Intermediate Similarity	NPD1613	Approved
0.7923	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7157	Approved
0.7899	Intermediate Similarity	NPD1398	Phase 1
0.787	Intermediate Similarity	NPD9365	Approved
0.7869	Intermediate Similarity	NPD1548	Phase 1
0.7788	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD4060	Phase 1
0.7752	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1778	Approved
0.7717	Intermediate Similarity	NPD6696	Suspended
0.7705	Intermediate Similarity	NPD7340	Approved
0.7698	Intermediate Similarity	NPD2235	Phase 2
0.7698	Intermediate Similarity	NPD2231	Phase 2
0.7685	Intermediate Similarity	NPD9295	Approved
0.7674	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD4749	Approved
0.7634	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7565	Intermediate Similarity	NPD291	Approved
0.7557	Intermediate Similarity	NPD3027	Phase 3
0.7521	Intermediate Similarity	NPD821	Approved
0.7521	Intermediate Similarity	NPD9697	Approved
0.752	Intermediate Similarity	NPD1357	Approved
0.7481	Intermediate Similarity	NPD596	Approved
0.7481	Intermediate Similarity	NPD600	Approved
0.748	Intermediate Similarity	NPD422	Phase 1
0.748	Intermediate Similarity	NPD1611	Approved
0.7462	Intermediate Similarity	NPD6584	Phase 3
0.746	Intermediate Similarity	NPD5846	Approved
0.746	Intermediate Similarity	NPD6516	Phase 2
0.7442	Intermediate Similarity	NPD8651	Approved
0.744	Intermediate Similarity	NPD1182	Approved
0.7434	Intermediate Similarity	NPD844	Approved
0.7424	Intermediate Similarity	NPD4625	Phase 3
0.7422	Intermediate Similarity	NPD2233	Approved
0.7422	Intermediate Similarity	NPD2230	Approved
0.7422	Intermediate Similarity	NPD2232	Approved
0.7413	Intermediate Similarity	NPD1653	Approved
0.7407	Intermediate Similarity	NPD6653	Approved
0.7385	Intermediate Similarity	NPD1794	Approved
0.7381	Intermediate Similarity	NPD5585	Approved
0.7368	Intermediate Similarity	NPD288	Approved
0.7364	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4908	Phase 1
0.7345	Intermediate Similarity	NPD9296	Approved
0.7344	Intermediate Similarity	NPD1535	Discovery
0.7339	Intermediate Similarity	NPD709	Approved
0.7319	Intermediate Similarity	NPD5762	Approved
0.7319	Intermediate Similarity	NPD5763	Approved
0.7317	Intermediate Similarity	NPD5283	Phase 1
0.7313	Intermediate Similarity	NPD6233	Phase 2
0.7313	Intermediate Similarity	NPD840	Approved
0.7313	Intermediate Similarity	NPD839	Approved
0.7299	Intermediate Similarity	NPD2154	Approved
0.7299	Intermediate Similarity	NPD2156	Approved
0.7299	Intermediate Similarity	NPD2155	Approved
0.7293	Intermediate Similarity	NPD7095	Approved
0.7287	Intermediate Similarity	NPD1481	Phase 2
0.7273	Intermediate Similarity	NPD1712	Approved
0.7266	Intermediate Similarity	NPD2424	Discontinued
0.7259	Intermediate Similarity	NPD1558	Phase 1
0.725	Intermediate Similarity	NPD1358	Approved
0.7246	Intermediate Similarity	NPD6032	Approved
0.7239	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7985	Registered
0.7239	Intermediate Similarity	NPD6798	Discontinued
0.7234	Intermediate Similarity	NPD2677	Approved
0.7231	Intermediate Similarity	NPD6582	Phase 2
0.7231	Intermediate Similarity	NPD6583	Phase 3
0.7214	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD776	Approved
0.7206	Intermediate Similarity	NPD5735	Approved
0.7206	Intermediate Similarity	NPD447	Suspended
0.7206	Intermediate Similarity	NPD6355	Discontinued
0.72	Intermediate Similarity	NPD2557	Approved
0.7197	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3690	Phase 2
0.7197	Intermediate Similarity	NPD558	Phase 2
0.7197	Intermediate Similarity	NPD3691	Phase 2
0.7188	Intermediate Similarity	NPD4626	Approved
0.7177	Intermediate Similarity	NPD1241	Discontinued
0.7154	Intermediate Similarity	NPD1840	Phase 2
0.7154	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD9501	Approved
0.7143	Intermediate Similarity	NPD2237	Approved
0.7132	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3620	Phase 2
0.7132	Intermediate Similarity	NPD2238	Phase 2
0.7121	Intermediate Similarity	NPD3827	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD987	Approved
0.7121	Intermediate Similarity	NPD1820	Approved
0.7121	Intermediate Similarity	NPD1818	Approved
0.7121	Intermediate Similarity	NPD1817	Approved
0.7121	Intermediate Similarity	NPD1819	Approved
0.7121	Intermediate Similarity	NPD2797	Approved
0.7111	Intermediate Similarity	NPD1048	Approved
0.7109	Intermediate Similarity	NPD6382	Discontinued
0.7109	Intermediate Similarity	NPD3443	Approved
0.7109	Intermediate Similarity	NPD3445	Approved
0.7109	Intermediate Similarity	NPD5691	Approved
0.7109	Intermediate Similarity	NPD3444	Approved
0.7107	Intermediate Similarity	NPD9552	Approved
0.7101	Intermediate Similarity	NPD4536	Approved
0.7101	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4538	Approved
0.7099	Intermediate Similarity	NPD4359	Approved
0.7097	Intermediate Similarity	NPD7635	Approved
0.7092	Intermediate Similarity	NPD1652	Phase 2
0.7083	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3163	Approved
0.7059	Intermediate Similarity	NPD3162	Approved
0.705	Intermediate Similarity	NPD7033	Discontinued
0.7047	Intermediate Similarity	NPD2801	Approved
0.7047	Intermediate Similarity	NPD5929	Approved
0.7045	Intermediate Similarity	NPD3225	Approved
0.7043	Intermediate Similarity	NPD2934	Approved
0.7043	Intermediate Similarity	NPD2933	Approved
0.704	Intermediate Similarity	NPD594	Approved
0.704	Intermediate Similarity	NPD592	Approved
0.7031	Intermediate Similarity	NPD1894	Discontinued
0.7025	Intermediate Similarity	NPD3134	Approved
0.7023	Intermediate Similarity	NPD9717	Approved
0.7014	Intermediate Similarity	NPD1774	Approved
0.7007	Intermediate Similarity	NPD4140	Approved
0.7007	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2935	Discontinued
0.7	Intermediate Similarity	NPD111	Approved
0.6992	Remote Similarity	NPD3021	Approved
0.6992	Remote Similarity	NPD1203	Approved
0.6992	Remote Similarity	NPD556	Approved
0.6992	Remote Similarity	NPD3022	Approved
0.6985	Remote Similarity	NPD1336	Approved
0.6983	Remote Similarity	NPD2860	Approved
0.6983	Remote Similarity	NPD2859	Approved
0.6978	Remote Similarity	NPD7097	Phase 1
0.6977	Remote Similarity	NPD3049	Approved
0.6972	Remote Similarity	NPD5177	Phase 3
0.697	Remote Similarity	NPD3685	Discontinued
0.697	Remote Similarity	NPD5327	Phase 3
0.6963	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.696	Remote Similarity	NPD5535	Approved
0.6957	Remote Similarity	NPD845	Approved
0.6953	Remote Similarity	NPD7644	Approved
0.6953	Remote Similarity	NPD5536	Phase 2
0.6949	Remote Similarity	NPD3020	Approved
0.6947	Remote Similarity	NPD3705	Approved
0.694	Remote Similarity	NPD5647	Approved
0.6934	Remote Similarity	NPD7477	Discontinued
0.6934	Remote Similarity	NPD1423	Approved
0.6934	Remote Similarity	NPD2674	Phase 3
0.6934	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4062	Phase 3
0.6929	Remote Similarity	NPD5588	Approved
0.6929	Remote Similarity	NPD5960	Phase 3
0.6923	Remote Similarity	NPD2667	Approved
0.6923	Remote Similarity	NPD2668	Approved
0.6923	Remote Similarity	NPD2556	Approved
0.6923	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD17	Approved
0.6923	Remote Similarity	NPD2554	Approved
0.6918	Remote Similarity	NPD6090	Discontinued
0.6918	Remote Similarity	NPD2676	Approved
0.6918	Remote Similarity	NPD2675	Approved
0.6917	Remote Similarity	NPD2922	Phase 1
0.6912	Remote Similarity	NPD3179	Approved
0.6912	Remote Similarity	NPD3166	Approved
0.6912	Remote Similarity	NPD3164	Approved
0.6912	Remote Similarity	NPD3165	Approved
0.6912	Remote Similarity	NPD3180	Approved
0.6912	Remote Similarity	NPD3167	Approved
0.6906	Remote Similarity	NPD6353	Approved
0.6906	Remote Similarity	NPD2157	Approved
0.6897	Remote Similarity	NPD1511	Approved
0.6897	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1242	Phase 1
0.6889	Remote Similarity	NPD3018	Phase 2
0.6887	Remote Similarity	NPD5402	Approved
0.6879	Remote Similarity	NPD6100	Approved
0.6879	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6099	Approved
0.6875	Remote Similarity	NPD3596	Phase 2
0.6875	Remote Similarity	NPD3692	Discontinued
0.6867	Remote Similarity	NPD1934	Approved
0.6866	Remote Similarity	NPD4098	Discontinued
0.6861	Remote Similarity	NPD411	Approved
0.6861	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6859	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