NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	386.1
Volume:	375.4
LogP:	2.742
LogD:	2.576
LogS:	-3.81
# Rotatable Bonds:	6
TPSA:	129.59
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.507
Synthetic Accessibility Score:	2.873
Fsp3:	0.15
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:	-5.012
MDCK Permeability:	7.64369178796187e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.318
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	98.21924591064453%
Volume Distribution (VD):	0.301
Pgp-substrate:	2.0074753761291504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.755
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.213
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.087
CYP2D6-substrate:	0.243
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	7.634
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.695
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.301
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.048
Carcinogencity:	0.062
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.353

Download Data

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

Natural Product: NPC476642

Natural Product ID:	NPC476642
*Common Name:**	Terphenolide
IUPAC Name:	2-[3-[2-hydroxy-4-(4-hydroxyphenyl)-3,6-dimethoxyphenyl]-5-oxo-2H-furan-2-yl]acetic acid
Synonyms:	Terphenolide
Standard InCHIKey:	LZDLOICWXKFSMI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O8/c1-26-15-7-12(10-3-5-11(21)6-4-10)20(27-2)19(25)18(15)13-8-17(24)28-14(13)9-16(22)23/h3-8,14,21,25H,9H2,1-2H3,(H,22,23)
SMILES:	COC1=C(C(=C(C(=C1)C2=CC=C(C=C2)O)OC)O)C3=CC(=O)OC3CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45782753
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO33649	Aspergillus sp. YXf3	Species	Aspergillaceae	Eukaryota	isolated from a healthy leaf of Ginkgo biloba	the campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	5790	nM	PMID[22196792]

☑ 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 NPC476642 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	350
0.1-0.2	1394
0.2-0.3	3321
0.3-0.4	8029
0.4-0.5	10364
0.5-0.6	3768
0.6-0.7	5414
0.7-0.8	8242
0.8-0.85	1608
0.85-0.9	201
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.915	High Similarity	NPC7178
0.915	High Similarity	NPC62903
0.9108	High Similarity	NPC55121
0.9108	High Similarity	NPC174311
0.9091	High Similarity	NPC142479
0.9091	High Similarity	NPC155015
0.9062	High Similarity	NPC476279
0.8961	High Similarity	NPC476154
0.8947	High Similarity	NPC125570
0.894	High Similarity	NPC208507
0.894	High Similarity	NPC472333
0.8896	High Similarity	NPC95498
0.8896	High Similarity	NPC246566
0.8896	High Similarity	NPC476434
0.8868	High Similarity	NPC476200
0.8868	High Similarity	NPC192258
0.8846	High Similarity	NPC125709
0.8846	High Similarity	NPC292385
0.8839	High Similarity	NPC199773
0.8839	High Similarity	NPC473236
0.8839	High Similarity	NPC289968
0.8831	High Similarity	NPC225129
0.8824	High Similarity	NPC113790
0.88	High Similarity	NPC477696
0.88	High Similarity	NPC273657
0.88	High Similarity	NPC106920
0.88	High Similarity	NPC477697
0.88	High Similarity	NPC470811
0.879	High Similarity	NPC227062
0.8758	High Similarity	NPC139839
0.8742	High Similarity	NPC16353
0.8733	High Similarity	NPC472335
0.8733	High Similarity	NPC472332
0.8718	High Similarity	NPC178574
0.8718	High Similarity	NPC65591
0.871	High Similarity	NPC164527
0.871	High Similarity	NPC213382
0.8701	High Similarity	NPC55327
0.8701	High Similarity	NPC474393
0.8701	High Similarity	NPC474347
0.8693	High Similarity	NPC275125
0.8693	High Similarity	NPC170239
0.8693	High Similarity	NPC97937
0.8684	High Similarity	NPC223185
0.8679	High Similarity	NPC45846
0.8671	High Similarity	NPC150227
0.8667	High Similarity	NPC19158
0.8667	High Similarity	NPC470991
0.8662	High Similarity	NPC298802
0.8662	High Similarity	NPC136757
0.8654	High Similarity	NPC477699
0.8645	High Similarity	NPC285527
0.8645	High Similarity	NPC106334
0.8645	High Similarity	NPC470916
0.8634	High Similarity	NPC42797
0.8634	High Similarity	NPC473445
0.8627	High Similarity	NPC474799
0.8625	High Similarity	NPC130955
0.8625	High Similarity	NPC301089
0.8625	High Similarity	NPC292415
0.8618	High Similarity	NPC87883
0.8618	High Similarity	NPC27159
0.8616	High Similarity	NPC162869
0.8616	High Similarity	NPC143328
0.8616	High Similarity	NPC36077
0.8616	High Similarity	NPC474836
0.8616	High Similarity	NPC475267
0.8616	High Similarity	NPC77679
0.8616	High Similarity	NPC156057
0.8616	High Similarity	NPC190020
0.8616	High Similarity	NPC474208
0.8616	High Similarity	NPC84935
0.8616	High Similarity	NPC48208
0.8609	High Similarity	NPC469564
0.8608	High Similarity	NPC238834
0.8608	High Similarity	NPC16082
0.8608	High Similarity	NPC286052
0.8608	High Similarity	NPC79998
0.8608	High Similarity	NPC199926
0.8608	High Similarity	NPC82592
0.8599	High Similarity	NPC295646
0.8589	High Similarity	NPC472452
0.8589	High Similarity	NPC20216
0.8581	High Similarity	NPC30688
0.8581	High Similarity	NPC176903
0.858	High Similarity	NPC156082
0.858	High Similarity	NPC477689
0.858	High Similarity	NPC291977
0.8571	High Similarity	NPC473106
0.8571	High Similarity	NPC283081
0.8571	High Similarity	NPC178129
0.8571	High Similarity	NPC221383
0.8571	High Similarity	NPC143892
0.8571	High Similarity	NPC112418
0.8571	High Similarity	NPC349525
0.8571	High Similarity	NPC299090
0.8571	High Similarity	NPC103201
0.8563	High Similarity	NPC196771
0.8562	High Similarity	NPC238381
0.8562	High Similarity	NPC83763
0.8562	High Similarity	NPC36354
0.8562	High Similarity	NPC168616
0.8562	High Similarity	NPC125617
0.8562	High Similarity	NPC474982
0.8553	High Similarity	NPC7439
0.8553	High Similarity	NPC469474
0.8553	High Similarity	NPC34245
0.8553	High Similarity	NPC110067
0.8553	High Similarity	NPC54928
0.8553	High Similarity	NPC256555
0.8553	High Similarity	NPC477616
0.8553	High Similarity	NPC91492
0.8553	High Similarity	NPC255106
0.8553	High Similarity	NPC235165
0.8545	High Similarity	NPC124470
0.8545	High Similarity	NPC109827
0.8545	High Similarity	NPC17219
0.8544	High Similarity	NPC124714
0.8544	High Similarity	NPC477299
0.8544	High Similarity	NPC281477
0.8544	High Similarity	NPC25127
0.8544	High Similarity	NPC250557
0.8544	High Similarity	NPC287504
0.8544	High Similarity	NPC18727
0.8543	High Similarity	NPC100675
0.8537	High Similarity	NPC311912
0.8535	High Similarity	NPC204350
0.8535	High Similarity	NPC93498
0.8535	High Similarity	NPC56184
0.8535	High Similarity	NPC75695
0.8535	High Similarity	NPC163883
0.8528	High Similarity	NPC112981
0.8526	High Similarity	NPC21184
0.8526	High Similarity	NPC102003
0.8526	High Similarity	NPC92722
0.8526	High Similarity	NPC205727
0.8526	High Similarity	NPC120426
0.8526	High Similarity	NPC294522
0.8519	High Similarity	NPC84515
0.8519	High Similarity	NPC312056
0.8519	High Similarity	NPC471745
0.8516	High Similarity	NPC1580
0.8516	High Similarity	NPC102934
0.8516	High Similarity	NPC252402
0.8514	High Similarity	NPC106406
0.8512	High Similarity	NPC297807
0.8509	High Similarity	NPC24627
0.8509	High Similarity	NPC53889
0.8509	High Similarity	NPC471744
0.8506	High Similarity	NPC474054
0.8503	High Similarity	NPC139350
0.85	High Similarity	NPC99597
0.85	High Similarity	NPC469584
0.85	High Similarity	NPC472910
0.85	High Similarity	NPC35598
0.85	High Similarity	NPC472913
0.85	High Similarity	NPC245758
0.85	High Similarity	NPC222814
0.85	High Similarity	NPC96167
0.85	High Similarity	NPC472911
0.85	High Similarity	NPC223787
0.85	High Similarity	NPC210084
0.85	High Similarity	NPC108456
0.85	High Similarity	NPC470402
0.85	High Similarity	NPC222689
0.85	High Similarity	NPC472914
0.8494	Intermediate Similarity	NPC247964
0.8494	Intermediate Similarity	NPC158226
0.8491	Intermediate Similarity	NPC280339
0.8491	Intermediate Similarity	NPC213622
0.8491	Intermediate Similarity	NPC183597
0.8491	Intermediate Similarity	NPC167815
0.8491	Intermediate Similarity	NPC196439
0.8491	Intermediate Similarity	NPC138360
0.8491	Intermediate Similarity	NPC4455
0.8491	Intermediate Similarity	NPC201136
0.8491	Intermediate Similarity	NPC163780
0.8491	Intermediate Similarity	NPC37392
0.8491	Intermediate Similarity	NPC50715
0.8491	Intermediate Similarity	NPC146165
0.8491	Intermediate Similarity	NPC92659
0.8491	Intermediate Similarity	NPC227325
0.8491	Intermediate Similarity	NPC128863
0.8491	Intermediate Similarity	NPC2476
0.8491	Intermediate Similarity	NPC476065
0.8485	Intermediate Similarity	NPC117911
0.8485	Intermediate Similarity	NPC88557
0.8481	Intermediate Similarity	NPC146277
0.8481	Intermediate Similarity	NPC291802
0.8481	Intermediate Similarity	NPC75069
0.8481	Intermediate Similarity	NPC181209
0.8481	Intermediate Similarity	NPC131266
0.8481	Intermediate Similarity	NPC149735
0.8481	Intermediate Similarity	NPC19380
0.8481	Intermediate Similarity	NPC216769
0.8481	Intermediate Similarity	NPC245382
0.8481	Intermediate Similarity	NPC474656
0.8481	Intermediate Similarity	NPC475141
0.8481	Intermediate Similarity	NPC121522
0.8481	Intermediate Similarity	NPC35763

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 NPC476642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	861
0.2-0.3	1776
0.3-0.4	2600
0.4-0.5	1855
0.5-0.6	1041
0.6-0.7	551
0.7-0.8	154
0.8-0.85	17
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD6232	Discontinued
0.8481	Intermediate Similarity	NPD1934	Approved
0.8447	Intermediate Similarity	NPD6234	Discontinued
0.8428	Intermediate Similarity	NPD2801	Approved
0.8373	Intermediate Similarity	NPD5844	Phase 1
0.8364	Intermediate Similarity	NPD7473	Discontinued
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD3817	Phase 2
0.825	Intermediate Similarity	NPD37	Approved
0.821	Intermediate Similarity	NPD4967	Phase 2
0.821	Intermediate Similarity	NPD4966	Approved
0.821	Intermediate Similarity	NPD3882	Suspended
0.821	Intermediate Similarity	NPD4965	Approved
0.8204	Intermediate Similarity	NPD3818	Discontinued
0.8193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6166	Phase 2
0.8193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD3027	Phase 3
0.8107	Intermediate Similarity	NPD7074	Phase 3
0.8095	Intermediate Similarity	NPD7228	Approved
0.8047	Intermediate Similarity	NPD7054	Approved
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD1653	Approved
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD1465	Phase 2
0.7975	Intermediate Similarity	NPD1511	Approved
0.7952	Intermediate Similarity	NPD5494	Approved
0.7939	Intermediate Similarity	NPD7075	Discontinued
0.7927	Intermediate Similarity	NPD5402	Approved
0.7925	Intermediate Similarity	NPD2533	Approved
0.7925	Intermediate Similarity	NPD2532	Approved
0.7925	Intermediate Similarity	NPD2534	Approved
0.7904	Intermediate Similarity	NPD7199	Phase 2
0.7901	Intermediate Similarity	NPD4380	Phase 2
0.7901	Intermediate Similarity	NPD6599	Discontinued
0.7895	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1613	Approved
0.7875	Intermediate Similarity	NPD1512	Approved
0.7862	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6797	Phase 2
0.7848	Intermediate Similarity	NPD6190	Approved
0.7829	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7251	Discontinued
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.7771	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7808	Phase 3
0.7758	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7819	Suspended
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.775	Intermediate Similarity	NPD6799	Approved
0.7748	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD230	Phase 1
0.7725	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6801	Discontinued
0.7692	Intermediate Similarity	NPD6959	Discontinued
0.7682	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1607	Approved
0.7673	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7768	Phase 2
0.7613	Intermediate Similarity	NPD6355	Discontinued
0.7607	Intermediate Similarity	NPD5403	Approved
0.76	Intermediate Similarity	NPD7240	Approved
0.7595	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1510	Phase 2
0.7574	Intermediate Similarity	NPD919	Approved
0.7562	Intermediate Similarity	NPD3750	Approved
0.7562	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4110	Phase 3
0.7548	Intermediate Similarity	NPD1240	Approved
0.7547	Intermediate Similarity	NPD1549	Phase 2
0.7533	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7411	Suspended
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7485	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD5401	Approved
0.7485	Intermediate Similarity	NPD8127	Discontinued
0.7484	Intermediate Similarity	NPD7266	Discontinued
0.7484	Intermediate Similarity	NPD6233	Phase 2
0.7457	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD943	Approved
0.7429	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2438	Suspended
0.7421	Intermediate Similarity	NPD2796	Approved
0.7419	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6798	Discontinued
0.7401	Intermediate Similarity	NPD7685	Pre-registration
0.7374	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3751	Discontinued
0.7358	Intermediate Similarity	NPD7033	Discontinued
0.7346	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3787	Discontinued
0.7341	Intermediate Similarity	NPD5710	Approved
0.7341	Intermediate Similarity	NPD5711	Approved
0.7338	Intermediate Similarity	NPD2861	Phase 2
0.7338	Intermediate Similarity	NPD3018	Phase 2
0.7333	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6746	Phase 2
0.7325	Intermediate Similarity	NPD4060	Phase 1
0.732	Intermediate Similarity	NPD2797	Approved
0.7317	Intermediate Similarity	NPD4357	Discontinued
0.7312	Intermediate Similarity	NPD6100	Approved
0.7312	Intermediate Similarity	NPD6099	Approved
0.731	Intermediate Similarity	NPD3749	Approved
0.7305	Intermediate Similarity	NPD3226	Approved
0.7299	Intermediate Similarity	NPD5242	Approved
0.729	Intermediate Similarity	NPD4908	Phase 1
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7273	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7549	Discontinued
0.7255	Intermediate Similarity	NPD1283	Approved
0.725	Intermediate Similarity	NPD3748	Approved
0.7244	Intermediate Similarity	NPD4625	Phase 3
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7239	Intermediate Similarity	NPD8166	Discontinued
0.7235	Intermediate Similarity	NPD8455	Phase 2
0.7222	Intermediate Similarity	NPD8312	Approved
0.7222	Intermediate Similarity	NPD8313	Approved
0.7219	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2979	Phase 3
0.7211	Intermediate Similarity	NPD7680	Approved
0.7202	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8434	Phase 2
0.7197	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3268	Approved
0.719	Intermediate Similarity	NPD2983	Phase 2
0.719	Intermediate Similarity	NPD2982	Phase 2
0.7186	Intermediate Similarity	NPD920	Approved
0.7179	Intermediate Similarity	NPD6832	Phase 2
0.7178	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1652	Phase 2
0.7171	Intermediate Similarity	NPD1610	Phase 2
0.717	Intermediate Similarity	NPD1933	Approved
0.716	Intermediate Similarity	NPD2346	Discontinued
0.7152	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7124	Intermediate Similarity	NPD2981	Phase 2
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7435	Discontinued
0.7115	Intermediate Similarity	NPD9494	Approved
0.7113	Intermediate Similarity	NPD8151	Discontinued
0.7108	Intermediate Similarity	NPD7390	Discontinued
0.7105	Intermediate Similarity	NPD3496	Discontinued
0.7104	Intermediate Similarity	NPD8150	Discontinued
0.7099	Intermediate Similarity	NPD5405	Approved
0.7099	Intermediate Similarity	NPD5404	Approved
0.7099	Intermediate Similarity	NPD5408	Approved
0.7099	Intermediate Similarity	NPD5406	Approved
0.7097	Intermediate Similarity	NPD1203	Approved
0.7093	Intermediate Similarity	NPD5353	Approved
0.7086	Intermediate Similarity	NPD5691	Approved
0.7078	Intermediate Similarity	NPD4749	Approved
0.7073	Intermediate Similarity	NPD1243	Approved
0.7073	Intermediate Similarity	NPD2800	Approved
0.7067	Intermediate Similarity	NPD5536	Phase 2
0.7066	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5124	Phase 1
0.7063	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1535	Discovery
0.7059	Intermediate Similarity	NPD1281	Approved
0.7056	Intermediate Similarity	NPD5953	Discontinued
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD5762	Approved
0.7055	Intermediate Similarity	NPD5763	Approved
0.7055	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6005	Phase 3
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7053	Intermediate Similarity	NPD6778	Approved
0.7053	Intermediate Similarity	NPD6776	Approved
0.7053	Intermediate Similarity	NPD6780	Approved
0.7053	Intermediate Similarity	NPD6781	Approved
0.7053	Intermediate Similarity	NPD6782	Approved
0.7053	Intermediate Similarity	NPD6779	Approved
0.7053	Intermediate Similarity	NPD6777	Approved
0.7048	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4062	Phase 3
0.7041	Intermediate Similarity	NPD7783	Phase 2
0.7041	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1778	Approved
0.7037	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4308	Phase 3
0.703	Intermediate Similarity	NPD7003	Approved
0.7027	Intermediate Similarity	NPD5283	Phase 1

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