NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	440.18
Volume:	447.17
LogP:	5.38
LogD:	3.181
LogS:	-2.81
# Rotatable Bonds:	4
TPSA:	98.36
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	3.758
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.803
MDCK Permeability:	1.0394605851615779e-05
Pgp-inhibitor:	0.731
Pgp-substrate:	0.815
Human Intestinal Absorption (HIA):	0.161
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	81.33702850341797%
Volume Distribution (VD):	0.996
Pgp-substrate:	19.632884979248047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.192
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.29
CYP2C19-substrate:	0.387
CYP2C9-inhibitor:	0.729
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.22
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.273
CYP3A4-substrate:	0.301

ADMET: Excretion

Clearance (CL):	5.488
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.899
Drug-inuced Liver Injury (DILI):	0.235
AMES Toxicity:	0.152
Rat Oral Acute Toxicity:	0.527
Maximum Recommended Daily Dose:	0.569
Skin Sensitization:	0.299
Carcinogencity:	0.058
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.498

Download Data

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

Natural Product: NPC477154

Natural Product ID:	NPC477154
*Common Name:**	11-hydroxy-3-O-methyl-1-isomangostin
IUPAC Name:	3,9-dihydroxy-5,10-dimethoxy-2,2-dimethyl-11-(3-methylbut-2-enyl)-3,4-dihydropyrano[2,3-a]xanthen-12-one
Synonyms:
Standard InCHIKey:	GPNDGLHOWXPANW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H28O7/c1-12(2)7-8-13-20-17(10-15(26)23(13)30-6)31-18-11-16(29-5)14-9-19(27)25(3,4)32-24(14)21(18)22(20)28/h7,10-11,19,26-27H,8-9H2,1-6H3
SMILES:	CC(=CCC1=C(C(=CC2=C1C(=O)C3=C4C(=C(C=C3O2)OC)CC(C(O4)(C)C)O)O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46880202
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003519] 8-prenylated xanthones

*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
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18464091]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558747]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	stem bark	Pangradin village, Jasinga, West Java, Indonesia	2005-AUG	PMID[19839614]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20817450]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[24555285]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6249	Garcinia mangostana	Species	Clusiaceae	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	1
IC50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10	nM	PMID[19839614]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	IC50	>	20000	nM	PMID[19839614]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	20000	nM	PMID[19839614]

☑ 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 NPC477154 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	443
0.1-0.2	1750
0.2-0.3	3877
0.3-0.4	9897
0.4-0.5	8586
0.5-0.6	3620
0.6-0.7	5007
0.7-0.8	5076
0.8-0.85	2447
0.85-0.9	1447
0.9-0.95	491
0.95-1	56

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC117854
1.0	High Similarity	NPC6588
0.9809	High Similarity	NPC248638
0.9809	High Similarity	NPC152659
0.9809	High Similarity	NPC236521
0.9745	High Similarity	NPC25152
0.9686	High Similarity	NPC170245
0.9684	High Similarity	NPC7483
0.9682	High Similarity	NPC61010
0.9625	High Similarity	NPC474024
0.9623	High Similarity	NPC472450
0.9623	High Similarity	NPC239752
0.9623	High Similarity	NPC275780
0.9623	High Similarity	NPC326520
0.9623	High Similarity	NPC293319
0.9618	High Similarity	NPC200746
0.9618	High Similarity	NPC174953
0.9618	High Similarity	NPC228785
0.9618	High Similarity	NPC56085
0.9618	High Similarity	NPC14353
0.9563	High Similarity	NPC39091
0.9563	High Similarity	NPC472449
0.956	High Similarity	NPC189473
0.956	High Similarity	NPC146134
0.956	High Similarity	NPC23298
0.956	High Similarity	NPC475985
0.956	High Similarity	NPC186686
0.9557	High Similarity	NPC472632
0.9557	High Similarity	NPC474186
0.9557	High Similarity	NPC278052
0.9557	High Similarity	NPC40491
0.9557	High Similarity	NPC134783
0.9554	High Similarity	NPC329091
0.9554	High Similarity	NPC100123
0.9554	High Similarity	NPC473990
0.9554	High Similarity	NPC476242
0.95	High Similarity	NPC62261
0.95	High Similarity	NPC224280
0.9497	High Similarity	NPC52204
0.9497	High Similarity	NPC474034
0.9497	High Similarity	NPC220912
0.9497	High Similarity	NPC229632
0.9497	High Similarity	NPC474033
0.9494	High Similarity	NPC475886
0.9494	High Similarity	NPC320359
0.9494	High Similarity	NPC474287
0.9494	High Similarity	NPC36217
0.949	High Similarity	NPC241904
0.949	High Similarity	NPC217677
0.949	High Similarity	NPC165977
0.949	High Similarity	NPC300727
0.949	High Similarity	NPC223787
0.9444	High Similarity	NPC326877
0.9441	High Similarity	NPC120593
0.9441	High Similarity	NPC37870
0.9441	High Similarity	NPC43319
0.9437	High Similarity	NPC273959
0.9437	High Similarity	NPC197168
0.9437	High Similarity	NPC41301
0.9437	High Similarity	NPC220313
0.9437	High Similarity	NPC236132
0.9434	High Similarity	NPC474038
0.9434	High Similarity	NPC471212
0.9434	High Similarity	NPC474187
0.9434	High Similarity	NPC228383
0.9434	High Similarity	NPC471210
0.9434	High Similarity	NPC474351
0.9434	High Similarity	NPC471211
0.9434	High Similarity	NPC475883
0.943	High Similarity	NPC250214
0.943	High Similarity	NPC95936
0.9427	High Similarity	NPC142339
0.9427	High Similarity	NPC274730
0.9387	High Similarity	NPC103307
0.9383	High Similarity	NPC218226
0.9379	High Similarity	NPC25361
0.9379	High Similarity	NPC473286
0.9379	High Similarity	NPC234052
0.9379	High Similarity	NPC475888
0.9375	High Similarity	NPC329760
0.9375	High Similarity	NPC472448
0.9375	High Similarity	NPC474162
0.9375	High Similarity	NPC472964
0.9375	High Similarity	NPC83922
0.9375	High Similarity	NPC211107
0.9375	High Similarity	NPC201800
0.9375	High Similarity	NPC474150
0.9371	High Similarity	NPC471973
0.9371	High Similarity	NPC204290
0.9371	High Similarity	NPC471976
0.9371	High Similarity	NPC475784
0.9371	High Similarity	NPC119209
0.9371	High Similarity	NPC139036
0.9371	High Similarity	NPC472630
0.9371	High Similarity	NPC118256
0.9371	High Similarity	NPC472902
0.9371	High Similarity	NPC192686
0.9371	High Similarity	NPC472631
0.9371	High Similarity	NPC321399
0.9367	High Similarity	NPC469584
0.9367	High Similarity	NPC162869
0.9367	High Similarity	NPC156057
0.9367	High Similarity	NPC48208
0.9367	High Similarity	NPC472598
0.9367	High Similarity	NPC136674
0.9367	High Similarity	NPC78225
0.9367	High Similarity	NPC475267
0.9367	High Similarity	NPC474208
0.9367	High Similarity	NPC27337
0.9367	High Similarity	NPC474055
0.9367	High Similarity	NPC262286
0.9367	High Similarity	NPC236796
0.9367	High Similarity	NPC36852
0.9367	High Similarity	NPC474836
0.9367	High Similarity	NPC471209
0.9363	High Similarity	NPC477503
0.9363	High Similarity	NPC470327
0.9363	High Similarity	NPC45849
0.9363	High Similarity	NPC200761
0.9329	High Similarity	NPC121333
0.9325	High Similarity	NPC177480
0.9325	High Similarity	NPC152477
0.9321	High Similarity	NPC471213
0.9321	High Similarity	NPC128293
0.9321	High Similarity	NPC173292
0.9321	High Similarity	NPC477517
0.9317	High Similarity	NPC124038
0.9317	High Similarity	NPC474240
0.9317	High Similarity	NPC270837
0.9317	High Similarity	NPC472625
0.9317	High Similarity	NPC207690
0.9313	High Similarity	NPC472634
0.9313	High Similarity	NPC32694
0.9313	High Similarity	NPC3629
0.9313	High Similarity	NPC173137
0.9313	High Similarity	NPC29876
0.9313	High Similarity	NPC26326
0.9313	High Similarity	NPC167678
0.9313	High Similarity	NPC266314
0.9308	High Similarity	NPC85121
0.9308	High Similarity	NPC210459
0.9308	High Similarity	NPC474290
0.9304	High Similarity	NPC255106
0.9304	High Similarity	NPC138243
0.9304	High Similarity	NPC195796
0.9304	High Similarity	NPC68093
0.9304	High Similarity	NPC35038
0.9304	High Similarity	NPC278778
0.9304	High Similarity	NPC235165
0.9304	High Similarity	NPC209614
0.9304	High Similarity	NPC191146
0.9304	High Similarity	NPC24640
0.9304	High Similarity	NPC291878
0.9304	High Similarity	NPC470328
0.9304	High Similarity	NPC472626
0.9299	High Similarity	NPC74924
0.9299	High Similarity	NPC89474
0.9286	High Similarity	NPC150977
0.9268	High Similarity	NPC74559
0.9268	High Similarity	NPC472276
0.9264	High Similarity	NPC158761
0.9264	High Similarity	NPC225419
0.9264	High Similarity	NPC8965
0.9264	High Similarity	NPC14662
0.9259	High Similarity	NPC470457
0.9259	High Similarity	NPC50960
0.9255	High Similarity	NPC476247
0.9255	High Similarity	NPC472635
0.9255	High Similarity	NPC261470
0.9255	High Similarity	NPC472402
0.9255	High Similarity	NPC473961
0.9255	High Similarity	NPC294965
0.9255	High Similarity	NPC81679
0.925	High Similarity	NPC470326
0.925	High Similarity	NPC80375
0.925	High Similarity	NPC474960
0.925	High Similarity	NPC235018
0.925	High Similarity	NPC155302
0.925	High Similarity	NPC45146
0.925	High Similarity	NPC161947
0.925	High Similarity	NPC282009
0.925	High Similarity	NPC119224
0.925	High Similarity	NPC472624
0.925	High Similarity	NPC299436
0.925	High Similarity	NPC476980
0.925	High Similarity	NPC263449
0.925	High Similarity	NPC287328
0.9245	High Similarity	NPC473272
0.9245	High Similarity	NPC472911
0.9245	High Similarity	NPC472913
0.9245	High Similarity	NPC284820
0.9245	High Similarity	NPC96167
0.9245	High Similarity	NPC472914
0.9245	High Similarity	NPC210084
0.9245	High Similarity	NPC222814
0.9245	High Similarity	NPC472910
0.9245	High Similarity	NPC245758
0.9245	High Similarity	NPC99597
0.9245	High Similarity	NPC291508
0.9245	High Similarity	NPC470402

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 NPC477154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	971
0.2-0.3	1882
0.3-0.4	2631
0.4-0.5	1793
0.5-0.6	904
0.6-0.7	397
0.7-0.8	130
0.8-0.85	32
0.85-0.9	16
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9177	High Similarity	NPD2393	Clinical (unspecified phase)
0.9114	High Similarity	NPD1934	Approved
0.9057	High Similarity	NPD2801	Approved
0.9024	High Similarity	NPD6168	Clinical (unspecified phase)
0.9024	High Similarity	NPD6166	Phase 2
0.9024	High Similarity	NPD6167	Clinical (unspecified phase)
0.9012	High Similarity	NPD5494	Approved
0.881	High Similarity	NPD7074	Phase 3
0.875	High Similarity	NPD5844	Phase 1
0.875	High Similarity	NPD7054	Approved
0.8698	High Similarity	NPD7472	Approved
0.8655	High Similarity	NPD4338	Clinical (unspecified phase)
0.8634	High Similarity	NPD4380	Phase 2
0.8614	High Similarity	NPD6959	Discontinued
0.8598	High Similarity	NPD3882	Suspended
0.8598	High Similarity	NPD4868	Clinical (unspecified phase)
0.858	High Similarity	NPD3818	Discontinued
0.8538	High Similarity	NPD6797	Phase 2
0.8491	Intermediate Similarity	NPD1511	Approved
0.8488	Intermediate Similarity	NPD7251	Discontinued
0.8476	Intermediate Similarity	NPD1465	Phase 2
0.8452	Intermediate Similarity	NPD6232	Discontinued
0.8439	Intermediate Similarity	NPD7808	Phase 3
0.8412	Intermediate Similarity	NPD7473	Discontinued
0.8385	Intermediate Similarity	NPD1512	Approved
0.8364	Intermediate Similarity	NPD7819	Suspended
0.8324	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8314	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3817	Phase 2
0.8313	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1549	Phase 2
0.8098	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5402	Approved
0.8084	Intermediate Similarity	NPD6801	Discontinued
0.8066	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7411	Suspended
0.7988	Intermediate Similarity	NPD2533	Approved
0.7988	Intermediate Similarity	NPD2534	Approved
0.7988	Intermediate Similarity	NPD2532	Approved
0.7966	Intermediate Similarity	NPD6559	Discontinued
0.7965	Intermediate Similarity	NPD1247	Approved
0.7943	Intermediate Similarity	NPD7228	Approved
0.7943	Intermediate Similarity	NPD3751	Discontinued
0.7937	Intermediate Similarity	NPD2796	Approved
0.7919	Intermediate Similarity	NPD3787	Discontinued
0.7895	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD1510	Phase 2
0.7849	Intermediate Similarity	NPD6234	Discontinued
0.7848	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1613	Approved
0.784	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6799	Approved
0.7791	Intermediate Similarity	NPD2800	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8312	Approved
0.7778	Intermediate Similarity	NPD8313	Approved
0.7766	Intermediate Similarity	NPD6781	Approved
0.7766	Intermediate Similarity	NPD6777	Approved
0.7766	Intermediate Similarity	NPD6779	Approved
0.7766	Intermediate Similarity	NPD6776	Approved
0.7766	Intermediate Similarity	NPD6782	Approved
0.7766	Intermediate Similarity	NPD6780	Approved
0.7766	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6778	Approved
0.7765	Intermediate Similarity	NPD37	Approved
0.7751	Intermediate Similarity	NPD6599	Discontinued
0.7744	Intermediate Similarity	NPD3750	Approved
0.7736	Intermediate Similarity	NPD943	Approved
0.7736	Intermediate Similarity	NPD1240	Approved
0.7733	Intermediate Similarity	NPD4966	Approved
0.7733	Intermediate Similarity	NPD4967	Phase 2
0.7733	Intermediate Similarity	NPD7768	Phase 2
0.7733	Intermediate Similarity	NPD4965	Approved
0.7716	Intermediate Similarity	NPD2935	Discontinued
0.7679	Intermediate Similarity	NPD5403	Approved
0.767	Intermediate Similarity	NPD3926	Phase 2
0.7658	Intermediate Similarity	NPD3027	Phase 3
0.7657	Intermediate Similarity	NPD7199	Phase 2
0.7654	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD8150	Discontinued
0.7644	Intermediate Similarity	NPD7698	Approved
0.7644	Intermediate Similarity	NPD7696	Phase 3
0.7644	Intermediate Similarity	NPD7697	Approved
0.7644	Intermediate Similarity	NPD919	Approved
0.7644	Intermediate Similarity	NPD7435	Discontinued
0.7643	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD7783	Phase 2
0.7641	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1607	Approved
0.7629	Intermediate Similarity	NPD8151	Discontinued
0.7607	Intermediate Similarity	NPD6099	Approved
0.7607	Intermediate Similarity	NPD6100	Approved
0.7605	Intermediate Similarity	NPD7390	Discontinued
0.7595	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD3226	Approved
0.7578	Intermediate Similarity	NPD230	Phase 1
0.7577	Intermediate Similarity	NPD7701	Phase 2
0.7561	Intermediate Similarity	NPD2346	Discontinued
0.756	Intermediate Similarity	NPD5401	Approved
0.756	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD1653	Approved
0.7514	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD5710	Approved
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD6823	Phase 2
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.7485	Intermediate Similarity	NPD6190	Approved
0.7474	Intermediate Similarity	NPD7700	Phase 2
0.7474	Intermediate Similarity	NPD7699	Phase 2
0.7473	Intermediate Similarity	NPD7685	Pre-registration
0.7473	Intermediate Similarity	NPD7240	Approved
0.7472	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8434	Phase 2
0.7439	Intermediate Similarity	NPD3748	Approved
0.7432	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7874	Approved
0.7411	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4360	Phase 2
0.7407	Intermediate Similarity	NPD4363	Phase 3
0.7391	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7801	Approved
0.7368	Intermediate Similarity	NPD920	Approved
0.7368	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD447	Suspended
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.7329	Intermediate Similarity	NPD4625	Phase 3
0.7322	Intermediate Similarity	NPD5953	Discontinued
0.7321	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6651	Approved
0.7308	Intermediate Similarity	NPD7286	Phase 2
0.7289	Intermediate Similarity	NPD1551	Phase 2
0.7284	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4908	Phase 1
0.7262	Intermediate Similarity	NPD1243	Approved
0.7262	Intermediate Similarity	NPD6674	Discontinued
0.7259	Intermediate Similarity	NPD7584	Approved
0.7257	Intermediate Similarity	NPD6844	Discontinued
0.7251	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2344	Approved
0.724	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8455	Phase 2
0.7206	Intermediate Similarity	NPD4111	Phase 1
0.7206	Intermediate Similarity	NPD4665	Approved
0.7205	Intermediate Similarity	NPD9494	Approved
0.7202	Intermediate Similarity	NPD2424	Discontinued
0.7193	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2494	Approved
0.7179	Intermediate Similarity	NPD2493	Approved
0.7178	Intermediate Similarity	NPD2313	Discontinued
0.7173	Intermediate Similarity	NPD6212	Phase 3
0.7173	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6213	Phase 3
0.7165	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD8320	Phase 1
0.7157	Intermediate Similarity	NPD8319	Approved
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1933	Approved
0.7136	Intermediate Similarity	NPD7907	Approved
0.7135	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.7102	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2861	Phase 2
0.7092	Intermediate Similarity	NPD3452	Approved
0.7092	Intermediate Similarity	NPD3450	Approved
0.7091	Intermediate Similarity	NPD4060	Phase 1
0.7088	Intermediate Similarity	NPD5242	Approved
0.7079	Intermediate Similarity	NPD5353	Approved
0.7076	Intermediate Similarity	NPD2309	Approved
0.7073	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8127	Discontinued
0.7071	Intermediate Similarity	NPD4583	Approved
0.7071	Intermediate Similarity	NPD4582	Approved
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7549	Discontinued
0.7053	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2403	Approved
0.7044	Intermediate Similarity	NPD1610	Phase 2
0.7044	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7266	Discontinued
0.7022	Intermediate Similarity	NPD5760	Phase 2
0.7022	Intermediate Similarity	NPD5761	Phase 2

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