NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.09
Volume:	238.27
LogP:	0.859
LogD:	0.503
LogS:	-0.886
# Rotatable Bonds:	3
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.764
Synthetic Accessibility Score:	3.529
Fsp3:	0.308
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:	-5.082
MDCK Permeability:	1.7363523511448875e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.097
Human Intestinal Absorption (HIA):	0.403
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983
Plasma Protein Binding (PPB):	85.78684997558594%
Volume Distribution (VD):	1.456
Pgp-substrate:	12.185769081115723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.128
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.271
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.867
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	4.201
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.154
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.781
Skin Sensitization:	0.884
Carcinogencity:	0.049
Eye Corrosion:	0.011
Eye Irritation:	0.822
Respiratory Toxicity:	0.541

Download Data

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

Natural Product: NPC242913

Natural Product ID:	NPC242913
*Common Name:**	Goniodiol
IUPAC Name:	(2R)-2-[(1R,2R)-1,2-dihydroxy-2-phenylethyl]-2,3-dihydropyran-6-one
Synonyms:	Goniodiol
Standard InCHIKey:	RTNQVKQMVIXUPZ-RTXFEEFZSA-N
Standard InCHI:	InChI=1S/C13H14O4/c14-11-8-4-7-10(17-11)13(16)12(15)9-5-2-1-3-6-9/h1-6,8,10,12-13,15-16H,7H2/t10-,12-,13+/m1/s1
SMILES:	c1ccc(cc1)[C@H]([C@H]([C@H]1CC=CC(=O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490371
PubChem CID:	180702
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713398]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[1479382]
NPO21404	Anagallis monelli	Species	Primulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17329877]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791471]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791473]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614426]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322367]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917277]
NPO26455	Merwilla natalensis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20329	Gymnacranthera paniculata	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27877	Eliokarmos thyrsoides	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7589	Baccharis spartioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5379	Cortinarius sanguineus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21404	Anagallis monelli	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13768	Swertia marginata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15053	Menispermum cocculus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14597	Prociphilus tessellatus	Species	Pemphigidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26455	Merwilla natalensis	Species	Hyacinthaceae	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
ED50	5
IC50	1
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.22	10'-1 ug/ml	PMID[542335]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	8.27	ug ml-1	PMID[542335]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.45	ug ml-1	PMID[542335]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.12	ug ml-1	PMID[542336]
NPT140	Organism	Artemia	Artemia	LC50	>	500.0	ug.mL-1	PMID[542335]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.51	uM	PMID[542337]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	19480.0	nM	PMID[542337]

☑ 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 NPC242913 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	212
0.1-0.2	938
0.2-0.3	3023
0.3-0.4	8074
0.4-0.5	11380
0.5-0.6	13224
0.6-0.7	5199
0.7-0.8	576
0.8-0.85	39
0.85-0.9	13
0.9-0.95	10
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC280616
1.0	High Similarity	NPC171831
0.9796	High Similarity	NPC37115
0.9796	High Similarity	NPC136962
0.9596	High Similarity	NPC474376
0.9596	High Similarity	NPC472316
0.9596	High Similarity	NPC475203
0.9596	High Similarity	NPC472315
0.95	High Similarity	NPC277788
0.932	High Similarity	NPC234376
0.9231	High Similarity	NPC265002
0.91	High Similarity	NPC91820
0.91	High Similarity	NPC82426
0.899	High Similarity	NPC98911
0.899	High Similarity	NPC472318
0.8911	High Similarity	NPC234305
0.8854	High Similarity	NPC472319
0.8824	High Similarity	NPC85977
0.8774	High Similarity	NPC185840
0.875	High Similarity	NPC472314
0.875	High Similarity	NPC475465
0.8738	High Similarity	NPC472919
0.8598	High Similarity	NPC158282
0.8302	Intermediate Similarity	NPC477251
0.83	Intermediate Similarity	NPC23453
0.8273	Intermediate Similarity	NPC172525
0.8257	Intermediate Similarity	NPC474314
0.819	Intermediate Similarity	NPC160382
0.8163	Intermediate Similarity	NPC304760
0.812	Intermediate Similarity	NPC471466
0.8108	Intermediate Similarity	NPC474363
0.8108	Intermediate Similarity	NPC87069
0.81	Intermediate Similarity	NPC119631
0.8091	Intermediate Similarity	NPC477250
0.8081	Intermediate Similarity	NPC173443
0.8056	Intermediate Similarity	NPC20485
0.8021	Intermediate Similarity	NPC308619
0.8021	Intermediate Similarity	NPC324835
0.8021	Intermediate Similarity	NPC127491
0.8018	Intermediate Similarity	NPC272524
0.8	Intermediate Similarity	NPC240108
0.8	Intermediate Similarity	NPC183700
0.8	Intermediate Similarity	NPC323007
0.8	Intermediate Similarity	NPC213156
0.7983	Intermediate Similarity	NPC79608
0.7982	Intermediate Similarity	NPC184633
0.7982	Intermediate Similarity	NPC114741
0.7982	Intermediate Similarity	NPC182549
0.7981	Intermediate Similarity	NPC210529
0.7981	Intermediate Similarity	NPC160548
0.7981	Intermediate Similarity	NPC175852
0.7981	Intermediate Similarity	NPC154517
0.7965	Intermediate Similarity	NPC473507
0.7905	Intermediate Similarity	NPC80115
0.789	Intermediate Similarity	NPC156648
0.7879	Intermediate Similarity	NPC96625
0.7879	Intermediate Similarity	NPC169050
0.7879	Intermediate Similarity	NPC286608
0.7876	Intermediate Similarity	NPC217472
0.787	Intermediate Similarity	NPC152384
0.787	Intermediate Similarity	NPC37714
0.787	Intermediate Similarity	NPC127676
0.7863	Intermediate Similarity	NPC476872
0.7863	Intermediate Similarity	NPC229600
0.7857	Intermediate Similarity	NPC58616
0.785	Intermediate Similarity	NPC304638
0.7838	Intermediate Similarity	NPC43584
0.7838	Intermediate Similarity	NPC476003
0.7838	Intermediate Similarity	NPC63345
0.7833	Intermediate Similarity	NPC476033
0.7818	Intermediate Similarity	NPC281604
0.7818	Intermediate Similarity	NPC206341
0.7812	Intermediate Similarity	NPC117180
0.781	Intermediate Similarity	NPC135951
0.7807	Intermediate Similarity	NPC210531
0.7797	Intermediate Similarity	NPC475328
0.7797	Intermediate Similarity	NPC11724
0.7788	Intermediate Similarity	NPC474641
0.7788	Intermediate Similarity	NPC308744
0.7778	Intermediate Similarity	NPC148060
0.7768	Intermediate Similarity	NPC470825
0.7768	Intermediate Similarity	NPC139946
0.7759	Intermediate Similarity	NPC309434
0.7755	Intermediate Similarity	NPC304538
0.7732	Intermediate Similarity	NPC329319
0.7732	Intermediate Similarity	NPC103326
0.7732	Intermediate Similarity	NPC87299
0.7732	Intermediate Similarity	NPC99394
0.7731	Intermediate Similarity	NPC52097
0.7731	Intermediate Similarity	NPC327070
0.7727	Intermediate Similarity	NPC260952
0.7719	Intermediate Similarity	NPC474685
0.7719	Intermediate Similarity	NPC306740
0.7712	Intermediate Similarity	NPC470849
0.7712	Intermediate Similarity	NPC470848
0.7706	Intermediate Similarity	NPC269457
0.7705	Intermediate Similarity	NPC288416
0.7705	Intermediate Similarity	NPC473993
0.77	Intermediate Similarity	NPC89377
0.7699	Intermediate Similarity	NPC474176
0.7692	Intermediate Similarity	NPC141791
0.7692	Intermediate Similarity	NPC263386
0.7679	Intermediate Similarity	NPC260818
0.7679	Intermediate Similarity	NPC133308
0.7679	Intermediate Similarity	NPC474157
0.7672	Intermediate Similarity	NPC122117
0.7672	Intermediate Similarity	NPC65791
0.7664	Intermediate Similarity	NPC253746
0.7664	Intermediate Similarity	NPC42211
0.7664	Intermediate Similarity	NPC469481
0.7658	Intermediate Similarity	NPC469636
0.7658	Intermediate Similarity	NPC474364
0.7652	Intermediate Similarity	NPC233669
0.7632	Intermediate Similarity	NPC95381
0.7629	Intermediate Similarity	NPC89950
0.7623	Intermediate Similarity	NPC61181
0.7615	Intermediate Similarity	NPC249067
0.7611	Intermediate Similarity	NPC321852
0.7607	Intermediate Similarity	NPC203124
0.7607	Intermediate Similarity	NPC275519
0.7593	Intermediate Similarity	NPC154905
0.7593	Intermediate Similarity	NPC60373
0.7593	Intermediate Similarity	NPC94343
0.7589	Intermediate Similarity	NPC471954
0.7589	Intermediate Similarity	NPC79543
0.7589	Intermediate Similarity	NPC474148
0.7589	Intermediate Similarity	NPC75272
0.7589	Intermediate Similarity	NPC276061
0.7586	Intermediate Similarity	NPC470820
0.7586	Intermediate Similarity	NPC281277
0.7583	Intermediate Similarity	NPC223351
0.7583	Intermediate Similarity	NPC325301
0.7573	Intermediate Similarity	NPC317645
0.757	Intermediate Similarity	NPC171843
0.757	Intermediate Similarity	NPC118343
0.7565	Intermediate Similarity	NPC469509
0.7565	Intermediate Similarity	NPC261453
0.7565	Intermediate Similarity	NPC33749
0.7565	Intermediate Similarity	NPC328593
0.7565	Intermediate Similarity	NPC41851
0.7561	Intermediate Similarity	NPC103533
0.7561	Intermediate Similarity	NPC472707
0.7549	Intermediate Similarity	NPC220893
0.7547	Intermediate Similarity	NPC92754
0.7547	Intermediate Similarity	NPC249912
0.7547	Intermediate Similarity	NPC276775
0.7547	Intermediate Similarity	NPC289201
0.7547	Intermediate Similarity	NPC325499
0.7544	Intermediate Similarity	NPC131530
0.7542	Intermediate Similarity	NPC470214
0.7542	Intermediate Similarity	NPC470215
0.7542	Intermediate Similarity	NPC109371
0.7541	Intermediate Similarity	NPC83218
0.7541	Intermediate Similarity	NPC126991
0.7524	Intermediate Similarity	NPC5472
0.7523	Intermediate Similarity	NPC301943
0.7523	Intermediate Similarity	NPC474365
0.7522	Intermediate Similarity	NPC264784
0.7522	Intermediate Similarity	NPC30563
0.7521	Intermediate Similarity	NPC224208
0.7521	Intermediate Similarity	NPC138798
0.7521	Intermediate Similarity	NPC474275
0.752	Intermediate Similarity	NPC289415
0.752	Intermediate Similarity	NPC17567
0.752	Intermediate Similarity	NPC319995
0.75	Intermediate Similarity	NPC85493
0.75	Intermediate Similarity	NPC301857
0.75	Intermediate Similarity	NPC149691
0.75	Intermediate Similarity	NPC176228
0.75	Intermediate Similarity	NPC83628
0.75	Intermediate Similarity	NPC99482
0.75	Intermediate Similarity	NPC474967
0.75	Intermediate Similarity	NPC146540
0.75	Intermediate Similarity	NPC265407
0.75	Intermediate Similarity	NPC471616
0.75	Intermediate Similarity	NPC147654
0.75	Intermediate Similarity	NPC40178
0.75	Intermediate Similarity	NPC77273
0.748	Intermediate Similarity	NPC471157
0.748	Intermediate Similarity	NPC477280
0.748	Intermediate Similarity	NPC19719
0.748	Intermediate Similarity	NPC136608
0.748	Intermediate Similarity	NPC252114
0.748	Intermediate Similarity	NPC477281
0.748	Intermediate Similarity	NPC38420
0.748	Intermediate Similarity	NPC114096
0.7479	Intermediate Similarity	NPC193193
0.7478	Intermediate Similarity	NPC120217
0.7478	Intermediate Similarity	NPC153053
0.7477	Intermediate Similarity	NPC51174
0.7477	Intermediate Similarity	NPC135464
0.7477	Intermediate Similarity	NPC35448
0.7477	Intermediate Similarity	NPC225060
0.7477	Intermediate Similarity	NPC92623
0.7477	Intermediate Similarity	NPC262826
0.7477	Intermediate Similarity	NPC78701
0.7476	Intermediate Similarity	NPC185501
0.746	Intermediate Similarity	NPC478255
0.746	Intermediate Similarity	NPC29734
0.746	Intermediate Similarity	NPC108553

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 NPC242913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	689
0.2-0.3	1474
0.3-0.4	2872
0.4-0.5	2240
0.5-0.6	1271
0.6-0.7	390
0.7-0.8	25
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8214	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD969	Suspended
0.7981	Intermediate Similarity	NPD9495	Approved
0.7879	Intermediate Similarity	NPD1282	Approved
0.7719	Intermediate Similarity	NPD2629	Approved
0.7719	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD6647	Phase 2
0.7652	Intermediate Similarity	NPD4198	Discontinued
0.7615	Intermediate Similarity	NPD1237	Approved
0.757	Intermediate Similarity	NPD1238	Approved
0.7549	Intermediate Similarity	NPD689	Discontinued
0.7434	Intermediate Similarity	NPD2067	Discontinued
0.7411	Intermediate Similarity	NPD1358	Approved
0.7396	Intermediate Similarity	NPD9294	Approved
0.7368	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD9256	Approved
0.7308	Intermediate Similarity	NPD9258	Approved
0.7297	Intermediate Similarity	NPD5909	Discontinued
0.7257	Intermediate Similarity	NPD290	Approved
0.7232	Intermediate Similarity	NPD5048	Discontinued
0.7207	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2182	Approved
0.7193	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5126	Approved
0.719	Intermediate Similarity	NPD5125	Phase 3
0.7188	Intermediate Similarity	NPD9716	Approved
0.7165	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD164	Approved
0.7105	Intermediate Similarity	NPD9532	Phase 3
0.7103	Intermediate Similarity	NPD1202	Approved
0.708	Intermediate Similarity	NPD9697	Approved
0.7068	Intermediate Similarity	NPD7266	Discontinued
0.7049	Intermediate Similarity	NPD5305	Approved
0.7049	Intermediate Similarity	NPD5306	Approved
0.7043	Intermediate Similarity	NPD2684	Approved
0.7031	Intermediate Similarity	NPD5454	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9545	Approved
0.7018	Intermediate Similarity	NPD3134	Approved
0.7	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD5926	Approved
0.6992	Remote Similarity	NPD4136	Approved
0.6992	Remote Similarity	NPD4106	Approved
0.6992	Remote Similarity	NPD4135	Approved
0.6961	Remote Similarity	NPD9491	Approved
0.6949	Remote Similarity	NPD7843	Approved
0.6944	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7798	Approved
0.6937	Remote Similarity	NPD2066	Phase 3
0.6935	Remote Similarity	NPD1091	Approved
0.6935	Remote Similarity	NPD4806	Approved
0.6935	Remote Similarity	NPD422	Phase 1
0.6935	Remote Similarity	NPD4807	Approved
0.6923	Remote Similarity	NPD9257	Approved
0.6923	Remote Similarity	NPD9259	Approved
0.6912	Remote Similarity	NPD4628	Phase 3
0.6891	Remote Similarity	NPD6010	Discontinued
0.6885	Remote Similarity	NPD7741	Discontinued
0.687	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6685	Approved
0.6855	Remote Similarity	NPD3496	Discontinued
0.685	Remote Similarity	NPD2628	Approved
0.685	Remote Similarity	NPD2625	Approved
0.685	Remote Similarity	NPD2159	Approved
0.685	Remote Similarity	NPD2626	Approved
0.685	Remote Similarity	NPD2160	Approved
0.685	Remote Similarity	NPD2627	Approved
0.685	Remote Similarity	NPD2797	Approved
0.6846	Remote Similarity	NPD6798	Discontinued
0.6838	Remote Similarity	NPD9713	Approved
0.6838	Remote Similarity	NPD1652	Phase 2
0.6829	Remote Similarity	NPD4102	Approved
0.6829	Remote Similarity	NPD4105	Approved
0.6825	Remote Similarity	NPD7876	Discontinued
0.6818	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5124	Phase 1
0.6818	Remote Similarity	NPD4340	Discontinued
0.6796	Remote Similarity	NPD3971	Phase 1
0.6794	Remote Similarity	NPD6233	Phase 2
0.6792	Remote Similarity	NPD531	Approved
0.6777	Remote Similarity	NPD7157	Approved
0.6772	Remote Similarity	NPD3225	Approved
0.6769	Remote Similarity	NPD7008	Discontinued
0.6767	Remote Similarity	NPD6653	Approved
0.6765	Remote Similarity	NPD226	Approved
0.6759	Remote Similarity	NPD1239	Approved
0.6754	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5765	Approved
0.6754	Remote Similarity	NPD1929	Approved
0.6754	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD1930	Approved
0.675	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1894	Discontinued
0.6746	Remote Similarity	NPD9717	Approved
0.6744	Remote Similarity	NPD5204	Approved
0.6742	Remote Similarity	NPD4060	Phase 1
0.6739	Remote Similarity	NPD6190	Approved
0.6729	Remote Similarity	NPD800	Approved
0.6726	Remote Similarity	NPD2555	Approved
0.6726	Remote Similarity	NPD2549	Approved
0.6726	Remote Similarity	NPD2550	Approved
0.6726	Remote Similarity	NPD2558	Approved
0.6726	Remote Similarity	NPD2552	Approved
0.6726	Remote Similarity	NPD2553	Approved
0.6724	Remote Similarity	NPD968	Approved
0.6723	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5292	Approved
0.6721	Remote Similarity	NPD5291	Approved
0.6719	Remote Similarity	NPD1203	Approved
0.6718	Remote Similarity	NPD3268	Approved
0.6696	Remote Similarity	NPD9612	Approved
0.6696	Remote Similarity	NPD9609	Approved
0.6696	Remote Similarity	NPD9611	Approved
0.6695	Remote Similarity	NPD5235	Approved
0.6695	Remote Similarity	NPD5237	Approved
0.6695	Remote Similarity	NPD5236	Approved
0.6695	Remote Similarity	NPD5239	Approved
0.6695	Remote Similarity	NPD5240	Approved
0.6694	Remote Similarity	NPD5951	Approved
0.6692	Remote Similarity	NPD4617	Approved
0.6692	Remote Similarity	NPD6355	Discontinued
0.6692	Remote Similarity	NPD4620	Approved
0.6692	Remote Similarity	NPD5201	Approved
0.6692	Remote Similarity	NPD5203	Approved
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD6287	Discontinued
0.6667	Remote Similarity	NPD9267	Approved
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9264	Approved
0.6667	Remote Similarity	NPD1090	Approved
0.6667	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1086	Approved
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD9263	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD1989	Approved
0.6667	Remote Similarity	NPD4189	Approved
0.6667	Remote Similarity	NPD4188	Approved
0.6667	Remote Similarity	NPD4480	Approved
0.6667	Remote Similarity	NPD1089	Approved
0.6667	Remote Similarity	NPD5535	Approved
0.6642	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.664	Remote Similarity	NPD4626	Approved
0.6639	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD2201	Approved
0.6637	Remote Similarity	NPD9712	Approved
0.662	Remote Similarity	NPD5403	Approved
0.6619	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3662	Phase 3
0.6615	Remote Similarity	NPD3663	Approved
0.6615	Remote Similarity	NPD3664	Approved
0.6615	Remote Similarity	NPD3661	Approved
0.6612	Remote Similarity	NPD1241	Discontinued
0.661	Remote Similarity	NPD74	Approved
0.661	Remote Similarity	NPD9266	Approved
0.6596	Remote Similarity	NPD5401	Approved
0.6591	Remote Similarity	NPD1048	Approved
0.6591	Remote Similarity	NPD2313	Discontinued
0.6591	Remote Similarity	NPD3764	Approved
0.6587	Remote Similarity	NPD3847	Discontinued
0.6583	Remote Similarity	NPD228	Approved
0.6583	Remote Similarity	NPD6912	Phase 3
0.6577	Remote Similarity	NPD1693	Approved
0.6577	Remote Similarity	NPD2933	Approved
0.6577	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2934	Approved
0.6573	Remote Similarity	NPD1653	Approved
0.6569	Remote Similarity	NPD9490	Approved
0.6569	Remote Similarity	NPD5762	Approved
0.6569	Remote Similarity	NPD5763	Approved
0.6567	Remote Similarity	NPD230	Phase 1
0.6565	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.656	Remote Similarity	NPD5691	Approved
0.6552	Remote Similarity	NPD3048	Approved
0.6552	Remote Similarity	NPD3046	Approved
0.6552	Remote Similarity	NPD3047	Approved
0.6549	Remote Similarity	NPD9710	Approved
0.6549	Remote Similarity	NPD9711	Approved
0.6547	Remote Similarity	NPD8166	Discontinued
0.6545	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1088	Approved
0.6544	Remote Similarity	NPD4308	Phase 3
0.6542	Remote Similarity	NPD4793	Discontinued
0.6535	Remote Similarity	NPD1535	Discovery
0.6525	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD291	Approved
0.6522	Remote Similarity	NPD1932	Approved
0.6522	Remote Similarity	NPD854	Approved
0.6522	Remote Similarity	NPD855	Approved
0.6522	Remote Similarity	NPD2424	Discontinued
0.6515	Remote Similarity	NPD3027	Phase 3
0.6515	Remote Similarity	NPD7095	Approved
0.6514	Remote Similarity	NPD3673	Approved
0.6514	Remote Similarity	NPD3672	Approved
0.6512	Remote Similarity	NPD5667	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data