NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	208.11
Volume:	217.457
LogP:	2.103
LogD:	2.098
LogS:	-2.433
# Rotatable Bonds:	1
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	3.155
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.576
MDCK Permeability:	2.343209234823007e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.888
Plasma Protein Binding (PPB):	84.78006744384766%
Volume Distribution (VD):	1.427
Pgp-substrate:	10.37944507598877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.583
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.675
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.439

ADMET: Excretion

Clearance (CL):	13.238
Half-life (T1/2):	0.845

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.562
Drug-inuced Liver Injury (DILI):	0.229
AMES Toxicity:	0.217
Rat Oral Acute Toxicity:	0.196
Maximum Recommended Daily Dose:	0.089
Skin Sensitization:	0.743
Carcinogencity:	0.665
Eye Corrosion:	0.004
Eye Irritation:	0.55
Respiratory Toxicity:	0.417

Download Data

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

Natural Product: NPC293801

Natural Product ID:	NPC293801
*Common Name:**	6-Methoxy-3,7-Dimethylisochroman-8-Ol
IUPAC Name:	6-methoxy-3,7-dimethyl-3,4-dihydro-1H-isochromen-8-ol
Synonyms:
Standard InCHIKey:	OQMJILQCXYKZEM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H16O3/c1-7-4-9-5-11(14-3)8(2)12(13)10(9)6-15-7/h5,7,13H,4,6H2,1-3H3
SMILES:	CC1Cc2cc(c(C)c(c2CO1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2261570
PubChem CID:	50969
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-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
NPO21988	Penicillium steckii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21988	Penicillium steckii	Species	Aspergillaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	33113.11	nM	PMID[512645]

☑ 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 NPC293801 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	392
0.1-0.2	1729
0.2-0.3	4538
0.3-0.4	12801
0.4-0.5	5492
0.5-0.6	4390
0.6-0.7	8301
0.7-0.8	4236
0.8-0.85	610
0.85-0.9	191
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9746	High Similarity	NPC57199
0.9344	High Similarity	NPC105031
0.9328	High Similarity	NPC3239
0.9328	High Similarity	NPC282255
0.92	High Similarity	NPC474494
0.92	High Similarity	NPC25729
0.9055	High Similarity	NPC160623
0.904	High Similarity	NPC53781
0.8992	High Similarity	NPC473107
0.8984	High Similarity	NPC472798
0.8968	High Similarity	NPC38017
0.8968	High Similarity	NPC215300
0.896	High Similarity	NPC170485
0.896	High Similarity	NPC82299
0.8952	High Similarity	NPC228503
0.8952	High Similarity	NPC138248
0.8934	High Similarity	NPC102639
0.8915	High Similarity	NPC24913
0.8915	High Similarity	NPC177712
0.8898	High Similarity	NPC472795
0.8898	High Similarity	NPC16577
0.8898	High Similarity	NPC472797
0.8898	High Similarity	NPC472796
0.8889	High Similarity	NPC473221
0.888	High Similarity	NPC105718
0.888	High Similarity	NPC278955
0.8872	High Similarity	NPC265075
0.8862	High Similarity	NPC476633
0.8819	High Similarity	NPC38604
0.8819	High Similarity	NPC211179
0.88	High Similarity	NPC197351
0.88	High Similarity	NPC106914
0.88	High Similarity	NPC246648
0.88	High Similarity	NPC134195
0.88	High Similarity	NPC86502
0.879	High Similarity	NPC74137
0.877	High Similarity	NPC184302
0.876	High Similarity	NPC282508
0.874	High Similarity	NPC473134
0.874	High Similarity	NPC186889
0.873	High Similarity	NPC188022
0.873	High Similarity	NPC131397
0.873	High Similarity	NPC113495
0.873	High Similarity	NPC102540
0.873	High Similarity	NPC17809
0.873	High Similarity	NPC470726
0.873	High Similarity	NPC285040
0.873	High Similarity	NPC103420
0.873	High Similarity	NPC476254
0.8722	High Similarity	NPC32630
0.872	High Similarity	NPC96940
0.8712	High Similarity	NPC472800
0.8689	High Similarity	NPC190514
0.8689	High Similarity	NPC131118
0.8689	High Similarity	NPC63010
0.8682	High Similarity	NPC254000
0.8682	High Similarity	NPC470727
0.8682	High Similarity	NPC27187
0.8682	High Similarity	NPC470225
0.8678	High Similarity	NPC150624
0.8678	High Similarity	NPC141090
0.8676	High Similarity	NPC473845
0.8672	High Similarity	NPC53986
0.8672	High Similarity	NPC274717
0.8672	High Similarity	NPC38664
0.8661	High Similarity	NPC470724
0.8661	High Similarity	NPC276212
0.8644	High Similarity	NPC168657
0.8644	High Similarity	NPC224870
0.864	High Similarity	NPC100099
0.864	High Similarity	NPC77789
0.864	High Similarity	NPC120638
0.864	High Similarity	NPC36016
0.864	High Similarity	NPC18128
0.8636	High Similarity	NPC37410
0.8629	High Similarity	NPC218753
0.8626	High Similarity	NPC469610
0.8615	High Similarity	NPC300875
0.8615	High Similarity	NPC15543
0.8615	High Similarity	NPC118114
0.8615	High Similarity	NPC236014
0.8615	High Similarity	NPC280653
0.8615	High Similarity	NPC228369
0.8615	High Similarity	NPC129106
0.8615	High Similarity	NPC206224
0.8615	High Similarity	NPC476166
0.8615	High Similarity	NPC164574
0.8615	High Similarity	NPC268917
0.8615	High Similarity	NPC17343
0.8615	High Similarity	NPC12875
0.8615	High Similarity	NPC181497
0.8615	High Similarity	NPC196765
0.8615	High Similarity	NPC8899
0.8615	High Similarity	NPC271945
0.8615	High Similarity	NPC150011
0.8615	High Similarity	NPC129784
0.8615	High Similarity	NPC207892
0.8607	High Similarity	NPC50521
0.8607	High Similarity	NPC221549
0.8607	High Similarity	NPC195466
0.8607	High Similarity	NPC69261
0.8607	High Similarity	NPC33270
0.8607	High Similarity	NPC474933
0.8607	High Similarity	NPC244816
0.8605	High Similarity	NPC222108
0.8605	High Similarity	NPC93962
0.8605	High Similarity	NPC96719
0.8595	High Similarity	NPC808
0.8594	High Similarity	NPC149796
0.8594	High Similarity	NPC46978
0.8583	High Similarity	NPC263753
0.8583	High Similarity	NPC76119
0.8583	High Similarity	NPC124030
0.8583	High Similarity	NPC4286
0.8571	High Similarity	NPC191462
0.8571	High Similarity	NPC472647
0.8571	High Similarity	NPC133463
0.8571	High Similarity	NPC206525
0.8571	High Similarity	NPC170328
0.8571	High Similarity	NPC126101
0.8571	High Similarity	NPC234952
0.8571	High Similarity	NPC76465
0.8571	High Similarity	NPC38761
0.8571	High Similarity	NPC472648
0.8571	High Similarity	NPC472649
0.8571	High Similarity	NPC327735
0.856	High Similarity	NPC193364
0.856	High Similarity	NPC212965
0.8551	High Similarity	NPC233980
0.8551	High Similarity	NPC471608
0.8551	High Similarity	NPC274454
0.8551	High Similarity	NPC215678
0.855	High Similarity	NPC469611
0.855	High Similarity	NPC13005
0.8548	High Similarity	NPC258979
0.8548	High Similarity	NPC93398
0.8548	High Similarity	NPC8283
0.8527	High Similarity	NPC223912
0.8525	High Similarity	NPC85292
0.8525	High Similarity	NPC229147
0.8525	High Similarity	NPC203113
0.8525	High Similarity	NPC54507
0.8516	High Similarity	NPC50315
0.8516	High Similarity	NPC230479
0.8516	High Similarity	NPC283049
0.8516	High Similarity	NPC26879
0.8512	High Similarity	NPC276737
0.8512	High Similarity	NPC22610
0.8507	High Similarity	NPC242715
0.8507	High Similarity	NPC266006
0.8507	High Similarity	NPC56329
0.8507	High Similarity	NPC71465
0.8507	High Similarity	NPC472646
0.8507	High Similarity	NPC22902
0.8504	High Similarity	NPC270030
0.85	High Similarity	NPC473521
0.8496	Intermediate Similarity	NPC258780
0.8496	Intermediate Similarity	NPC473413
0.8489	Intermediate Similarity	NPC174251
0.8489	Intermediate Similarity	NPC153182
0.8489	Intermediate Similarity	NPC474397
0.8485	Intermediate Similarity	NPC85435
0.848	Intermediate Similarity	NPC100108
0.848	Intermediate Similarity	NPC277798
0.848	Intermediate Similarity	NPC129176
0.8473	Intermediate Similarity	NPC211413
0.8473	Intermediate Similarity	NPC68205
0.8473	Intermediate Similarity	NPC164804
0.8473	Intermediate Similarity	NPC293203
0.8473	Intermediate Similarity	NPC118683
0.8473	Intermediate Similarity	NPC244888
0.8473	Intermediate Similarity	NPC103799
0.8473	Intermediate Similarity	NPC469907
0.8468	Intermediate Similarity	NPC85895
0.8468	Intermediate Similarity	NPC137294
0.8462	Intermediate Similarity	NPC471519
0.8462	Intermediate Similarity	NPC471518
0.8456	Intermediate Similarity	NPC71046
0.845	Intermediate Similarity	NPC469386
0.8444	Intermediate Similarity	NPC243996
0.8444	Intermediate Similarity	NPC132804
0.8444	Intermediate Similarity	NPC220344
0.8444	Intermediate Similarity	NPC470209
0.8444	Intermediate Similarity	NPC275061
0.8443	Intermediate Similarity	NPC464
0.8443	Intermediate Similarity	NPC167934
0.8443	Intermediate Similarity	NPC185541
0.8443	Intermediate Similarity	NPC53906
0.8438	Intermediate Similarity	NPC476653
0.8433	Intermediate Similarity	NPC30632
0.8433	Intermediate Similarity	NPC470802
0.8421	Intermediate Similarity	NPC198154
0.8421	Intermediate Similarity	NPC115335
0.8421	Intermediate Similarity	NPC124085
0.8421	Intermediate Similarity	NPC223008
0.8421	Intermediate Similarity	NPC296915
0.8421	Intermediate Similarity	NPC117048
0.8421	Intermediate Similarity	NPC209199
0.8421	Intermediate Similarity	NPC125649
0.8421	Intermediate Similarity	NPC225696

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 NPC293801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	1030
0.2-0.3	1770
0.3-0.4	2760
0.4-0.5	1593
0.5-0.6	935
0.6-0.7	602
0.7-0.8	96
0.8-0.85	12
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8898	High Similarity	NPD4625	Phase 3
0.872	High Similarity	NPD4749	Approved
0.8682	High Similarity	NPD6410	Clinical (unspecified phase)
0.8661	High Similarity	NPD6917	Clinical (unspecified phase)
0.856	High Similarity	NPD1610	Phase 2
0.8538	High Similarity	NPD4907	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD4908	Phase 1
0.824	Intermediate Similarity	NPD1548	Phase 1
0.8134	Intermediate Similarity	NPD1613	Approved
0.8134	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD4626	Approved
0.8099	Intermediate Similarity	NPD4750	Phase 3
0.8077	Intermediate Similarity	NPD6696	Suspended
0.8058	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD3027	Phase 3
0.8031	Intermediate Similarity	NPD5691	Approved
0.803	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD2861	Phase 2
0.8	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD1398	Phase 1
0.7971	Intermediate Similarity	NPD6100	Approved
0.7971	Intermediate Similarity	NPD6099	Approved
0.797	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD422	Phase 1
0.7815	Intermediate Similarity	NPD940	Approved
0.7815	Intermediate Similarity	NPD846	Approved
0.7795	Intermediate Similarity	NPD7340	Approved
0.7778	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD2534	Approved
0.7778	Intermediate Similarity	NPD2532	Approved
0.7754	Intermediate Similarity	NPD4097	Suspended
0.7746	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD4060	Phase 1
0.773	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6671	Approved
0.7681	Intermediate Similarity	NPD5124	Phase 1
0.7681	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6959	Discontinued
0.7615	Intermediate Similarity	NPD1651	Approved
0.7552	Intermediate Similarity	NPD6674	Discontinued
0.7537	Intermediate Similarity	NPD1283	Approved
0.75	Intermediate Similarity	NPD1607	Approved
0.7483	Intermediate Similarity	NPD7819	Suspended
0.7483	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2238	Phase 2
0.7482	Intermediate Similarity	NPD3620	Phase 2
0.7464	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD5327	Phase 3
0.7444	Intermediate Similarity	NPD1091	Approved
0.7438	Intermediate Similarity	NPD1242	Phase 1
0.7429	Intermediate Similarity	NPD5735	Approved
0.7424	Intermediate Similarity	NPD1778	Approved
0.7417	Intermediate Similarity	NPD37	Approved
0.7413	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8651	Approved
0.7403	Intermediate Similarity	NPD6234	Discontinued
0.7402	Intermediate Similarity	NPD228	Approved
0.7395	Intermediate Similarity	NPD844	Approved
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4965	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7379	Intermediate Similarity	NPD3892	Phase 2
0.7372	Intermediate Similarity	NPD3018	Phase 2
0.7361	Intermediate Similarity	NPD1549	Phase 2
0.736	Intermediate Similarity	NPD290	Approved
0.7358	Intermediate Similarity	NPD5844	Phase 1
0.7357	Intermediate Similarity	NPD4140	Approved
0.7357	Intermediate Similarity	NPD1240	Approved
0.7347	Intermediate Similarity	NPD7212	Phase 2
0.7347	Intermediate Similarity	NPD7041	Phase 2
0.7347	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7213	Phase 3
0.7344	Intermediate Similarity	NPD7635	Approved
0.7338	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1669	Approved
0.7333	Intermediate Similarity	NPD288	Approved
0.732	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3705	Approved
0.7313	Intermediate Similarity	NPD1611	Approved
0.7313	Intermediate Similarity	NPD1281	Approved
0.7302	Intermediate Similarity	NPD2684	Approved
0.7299	Intermediate Similarity	NPD4624	Approved
0.7297	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7447	Phase 1
0.7292	Intermediate Similarity	NPD5762	Approved
0.7292	Intermediate Similarity	NPD5763	Approved
0.7285	Intermediate Similarity	NPD4380	Phase 2
0.7273	Intermediate Similarity	NPD3091	Approved
0.7273	Intermediate Similarity	NPD1510	Phase 2
0.7261	Intermediate Similarity	NPD5711	Approved
0.7261	Intermediate Similarity	NPD6232	Discontinued
0.7261	Intermediate Similarity	NPD5710	Approved
0.726	Intermediate Similarity	NPD3750	Approved
0.7254	Intermediate Similarity	NPD6353	Approved
0.7254	Intermediate Similarity	NPD2157	Approved
0.725	Intermediate Similarity	NPD1809	Phase 2
0.7222	Intermediate Similarity	NPD2342	Discontinued
0.7206	Intermediate Similarity	NPD2982	Phase 2
0.7206	Intermediate Similarity	NPD2983	Phase 2
0.7192	Intermediate Similarity	NPD1652	Phase 2
0.719	Intermediate Similarity	NPD1934	Approved
0.7188	Intermediate Similarity	NPD7228	Approved
0.7185	Intermediate Similarity	NPD3092	Approved
0.7181	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7157	Approved
0.7176	Intermediate Similarity	NPD709	Approved
0.7174	Intermediate Similarity	NPD6584	Phase 3
0.7174	Intermediate Similarity	NPD3691	Phase 2
0.7174	Intermediate Similarity	NPD3690	Phase 2
0.7172	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5283	Phase 1
0.7153	Intermediate Similarity	NPD4108	Discontinued
0.7153	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1653	Approved
0.7143	Intermediate Similarity	NPD968	Approved
0.7133	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2230	Approved
0.7132	Intermediate Similarity	NPD2981	Phase 2
0.7132	Intermediate Similarity	NPD2232	Approved
0.7132	Intermediate Similarity	NPD2233	Approved
0.7125	Intermediate Similarity	NPD7473	Discontinued
0.7124	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1712	Approved
0.7115	Intermediate Similarity	NPD7075	Discontinued
0.7113	Intermediate Similarity	NPD2979	Phase 3
0.7105	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1551	Phase 2
0.7103	Intermediate Similarity	NPD2438	Suspended
0.7103	Intermediate Similarity	NPD2796	Approved
0.7103	Intermediate Similarity	NPD2935	Discontinued
0.7101	Intermediate Similarity	NPD3094	Phase 2
0.7083	Intermediate Similarity	NPD4536	Approved
0.7083	Intermediate Similarity	NPD4538	Approved
0.7083	Intermediate Similarity	NPD845	Approved
0.7083	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD821	Approved
0.7077	Intermediate Similarity	NPD7843	Approved
0.7073	Intermediate Similarity	NPD3020	Approved
0.707	Intermediate Similarity	NPD5709	Phase 3
0.7068	Intermediate Similarity	NPD7644	Approved
0.7051	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7768	Phase 2
0.7044	Intermediate Similarity	NPD7229	Phase 3
0.7037	Intermediate Similarity	NPD5125	Phase 3
0.7037	Intermediate Similarity	NPD5126	Approved
0.7032	Intermediate Similarity	NPD5929	Approved
0.7032	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7466	Approved
0.7025	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4666	Phase 3
0.702	Intermediate Similarity	NPD6090	Discontinued
0.7016	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7411	Suspended
0.7012	Intermediate Similarity	NPD6559	Discontinued
0.7007	Intermediate Similarity	NPD1608	Approved
0.7007	Intermediate Similarity	NPD2424	Discontinued
0.7007	Intermediate Similarity	NPD7037	Approved
0.7	Intermediate Similarity	NPD5736	Approved
0.6993	Remote Similarity	NPD4005	Discontinued
0.6986	Remote Similarity	NPD4477	Approved
0.6986	Remote Similarity	NPD4476	Approved
0.6985	Remote Similarity	NPD3496	Discontinued
0.698	Remote Similarity	NPD2677	Approved
0.6972	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2860	Approved
0.6967	Remote Similarity	NPD2859	Approved
0.6966	Remote Similarity	NPD2200	Suspended
0.6963	Remote Similarity	NPD1357	Approved
0.6963	Remote Similarity	NPD3443	Approved
0.6963	Remote Similarity	NPD3444	Approved
0.6963	Remote Similarity	NPD3445	Approved
0.6959	Remote Similarity	NPD2800	Approved
0.6957	Remote Similarity	NPD6583	Phase 3
0.6957	Remote Similarity	NPD6582	Phase 2
0.6954	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.695	Remote Similarity	NPD600	Approved
0.695	Remote Similarity	NPD596	Approved
0.6947	Remote Similarity	NPD1138	Approved
0.6939	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6004	Phase 3
0.6939	Remote Similarity	NPD6005	Phase 3
0.6939	Remote Similarity	NPD6002	Phase 3
0.6939	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6667	Approved
0.6933	Remote Similarity	NPD6666	Approved
0.6918	Remote Similarity	NPD5960	Phase 3
0.6918	Remote Similarity	NPD3748	Approved
0.6918	Remote Similarity	NPD5588	Approved
0.6913	Remote Similarity	NPD7003	Approved
0.6913	Remote Similarity	NPD4628	Phase 3
0.6912	Remote Similarity	NPD2667	Approved
0.6912	Remote Similarity	NPD3095	Discontinued
0.6912	Remote Similarity	NPD2668	Approved
0.6897	Remote Similarity	NPD6651	Approved
0.6894	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7741	Discontinued
0.6887	Remote Similarity	NPD7390	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data