NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	434.14
Volume:	433.341
LogP:	5.005
LogD:	2.444
LogS:	-4.403
# Rotatable Bonds:	0
TPSA:	117.2
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.286
Synthetic Accessibility Score:	3.644
Fsp3:	0.28
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.002
MDCK Permeability:	1.3276645404403098e-05
Pgp-inhibitor:	0.114
Pgp-substrate:	0.227
Human Intestinal Absorption (HIA):	0.487
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	88.93620300292969%
Volume Distribution (VD):	0.714
Pgp-substrate:	12.7501802444458%

ADMET: Metabolism

CYP1A2-inhibitor:	0.579
CYP1A2-substrate:	0.765
CYP2C19-inhibitor:	0.153
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.74
CYP2C9-substrate:	0.911
CYP2D6-inhibitor:	0.125
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	1.292
Half-life (T1/2):	0.353

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.397
Rat Oral Acute Toxicity:	0.215
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.881
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.508
Respiratory Toxicity:	0.117

Download Data

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

Natural Product: NPC476637

Natural Product ID:	NPC476637
*Common Name:**	Artelastoxanthone
IUPAC Name:	5,9,11,14-tetrahydroxy-3,3-dimethyl-6-prop-1-en-2-yl-6,7-dihydrochromeno[7,6-c]xanthen-8-one
Synonyms:	artelastoxanthone
Standard InCHIKey:	UIBUSXFOXNXBAR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H22O7/c1-10(2)13-9-14-21(29)18-15(27)7-11(26)8-16(18)31-23(14)19-17(13)22(30)24-12(20(19)28)5-6-25(3,4)32-24/h5-8,13,26-28,30H,1,9H2,2-4H3
SMILES:	CC(=C)C1CC2=C(C3=C1C(=C4C(=C3O)C=CC(O4)(C)C)O)OC5=CC(=CC(=C5C2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	5326337
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

*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
NPO2376	Artocarpus elasticus	Species	Moraceae	Eukaryota	roots	Ping-Tung Hsien, Taiwan	2002-AUG	PMID[16309328]
NPO2376	Artocarpus elasticus	Species	Moraceae	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	4

Activity Type	# Activity
Cell Line	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	10	ug/ml	PMID[16309328]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	3.9	ug/ml	PMID[16309328]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.1	ug/ml	PMID[16309328]
NPT2	Others	Unspecified		ED50	=	3.2	ug/ml	PMID[16309328]

☑ 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 NPC476637 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	478
0.1-0.2	1941
0.2-0.3	4319
0.3-0.4	10836
0.4-0.5	7276
0.5-0.6	3670
0.6-0.7	5230
0.7-0.8	5278
0.8-0.85	2283
0.85-0.9	1087
0.9-0.95	264
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
0.9812	High Similarity	NPC101107
0.981	High Similarity	NPC156432
0.975	High Similarity	NPC475805
0.9625	High Similarity	NPC37870
0.9565	High Similarity	NPC126204
0.9503	High Similarity	NPC472449
0.95	High Similarity	NPC189473
0.95	High Similarity	NPC207690
0.95	High Similarity	NPC23298
0.9497	High Similarity	NPC278427
0.9441	High Similarity	NPC303174
0.9441	High Similarity	NPC472450
0.9441	High Similarity	NPC239752
0.9441	High Similarity	NPC275780
0.9383	High Similarity	NPC43319
0.9383	High Similarity	NPC39091
0.9383	High Similarity	NPC272502
0.9379	High Similarity	NPC270837
0.9375	High Similarity	NPC259456
0.9367	High Similarity	NPC276444
0.9367	High Similarity	NPC471985
0.9325	High Similarity	NPC218226
0.9317	High Similarity	NPC294965
0.9317	High Similarity	NPC25152
0.9317	High Similarity	NPC229632
0.9317	High Similarity	NPC329760
0.9313	High Similarity	NPC471973
0.9313	High Similarity	NPC139036
0.9313	High Similarity	NPC204290
0.9308	High Similarity	NPC476630
0.9308	High Similarity	NPC218871
0.9268	High Similarity	NPC188079
0.9259	High Similarity	NPC236521
0.9259	High Similarity	NPC236132
0.9259	High Similarity	NPC248638
0.9259	High Similarity	NPC152659
0.9259	High Similarity	NPC186686
0.9259	High Similarity	NPC146134
0.9255	High Similarity	NPC167678
0.9255	High Similarity	NPC61010
0.9255	High Similarity	NPC66288
0.9255	High Similarity	NPC29876
0.925	High Similarity	NPC474290
0.925	High Similarity	NPC197856
0.925	High Similarity	NPC100123
0.925	High Similarity	NPC280680
0.9241	High Similarity	NPC170492
0.9222	High Similarity	NPC216307
0.9207	High Similarity	NPC476306
0.9198	High Similarity	NPC261470
0.9198	High Similarity	NPC474150
0.9198	High Similarity	NPC83922
0.9198	High Similarity	NPC194427
0.9198	High Similarity	NPC472448
0.9198	High Similarity	NPC206605
0.9198	High Similarity	NPC78332
0.9198	High Similarity	NPC474162
0.9193	High Similarity	NPC119224
0.9193	High Similarity	NPC56085
0.9193	High Similarity	NPC14353
0.9193	High Similarity	NPC476980
0.9193	High Similarity	NPC200746
0.9193	High Similarity	NPC476280
0.9193	High Similarity	NPC320359
0.9193	High Similarity	NPC228785
0.9187	High Similarity	NPC136674
0.9162	High Similarity	NPC227906
0.9146	High Similarity	NPC120593
0.9141	High Similarity	NPC12461
0.9141	High Similarity	NPC306321
0.9141	High Similarity	NPC220313
0.9141	High Similarity	NPC303460
0.9136	High Similarity	NPC40491
0.9136	High Similarity	NPC40037
0.9136	High Similarity	NPC198829
0.9136	High Similarity	NPC278052
0.913	High Similarity	NPC74178
0.913	High Similarity	NPC476242
0.913	High Similarity	NPC46736
0.913	High Similarity	NPC184755
0.9125	High Similarity	NPC68093
0.9125	High Similarity	NPC142339
0.9125	High Similarity	NPC191146
0.9125	High Similarity	NPC274730
0.9091	High Similarity	NPC6588
0.9091	High Similarity	NPC477154
0.9091	High Similarity	NPC117854
0.9091	High Similarity	NPC474024
0.9085	High Similarity	NPC50960
0.9085	High Similarity	NPC25361
0.9085	High Similarity	NPC130920
0.9085	High Similarity	NPC85057
0.9085	High Similarity	NPC293319
0.908	High Similarity	NPC52204
0.908	High Similarity	NPC470694
0.9074	High Similarity	NPC36217
0.9074	High Similarity	NPC297212
0.9074	High Similarity	NPC45146
0.9074	High Similarity	NPC474960
0.9074	High Similarity	NPC119209
0.9074	High Similarity	NPC235018
0.9074	High Similarity	NPC118256
0.9074	High Similarity	NPC192686
0.9074	High Similarity	NPC80375
0.9068	High Similarity	NPC300727
0.9068	High Similarity	NPC236796
0.9068	High Similarity	NPC241904
0.9068	High Similarity	NPC273843
0.9068	High Similarity	NPC474681
0.9068	High Similarity	NPC78225
0.9068	High Similarity	NPC165977
0.9068	High Similarity	NPC218313
0.9068	High Similarity	NPC476981
0.9068	High Similarity	NPC217677
0.9068	High Similarity	NPC237418
0.9062	High Similarity	NPC166054
0.9062	High Similarity	NPC472280
0.9062	High Similarity	NPC234255
0.9062	High Similarity	NPC55662
0.9057	High Similarity	NPC237994
0.9057	High Similarity	NPC471982
0.9057	High Similarity	NPC249570
0.9051	High Similarity	NPC88804
0.9051	High Similarity	NPC3825
0.9042	High Similarity	NPC4200
0.903	High Similarity	NPC170245
0.9024	High Similarity	NPC197168
0.9024	High Similarity	NPC7483
0.9018	High Similarity	NPC474187
0.9018	High Similarity	NPC32694
0.9018	High Similarity	NPC311740
0.9018	High Similarity	NPC474038
0.9018	High Similarity	NPC266314
0.9018	High Similarity	NPC472906
0.9018	High Similarity	NPC234644
0.9018	High Similarity	NPC258331
0.9012	High Similarity	NPC235448
0.9012	High Similarity	NPC204879
0.9012	High Similarity	NPC85121
0.9012	High Similarity	NPC469658
0.9006	High Similarity	NPC472455
0.9006	High Similarity	NPC282307
0.9006	High Similarity	NPC470762
0.9006	High Similarity	NPC474167
0.9006	High Similarity	NPC133970
0.9006	High Similarity	NPC5322
0.9006	High Similarity	NPC170026
0.9006	High Similarity	NPC13779
0.9006	High Similarity	NPC138243
0.9006	High Similarity	NPC472907
0.9006	High Similarity	NPC475799
0.9006	High Similarity	NPC6633
0.9	High Similarity	NPC22519
0.9	High Similarity	NPC178964
0.9	High Similarity	NPC69394
0.9	High Similarity	NPC231018
0.9	High Similarity	NPC176775
0.9	High Similarity	NPC145379
0.9	High Similarity	NPC274327
0.9	High Similarity	NPC255350
0.9	High Similarity	NPC280530
0.9	High Similarity	NPC47781
0.9	High Similarity	NPC183878
0.9	High Similarity	NPC89474
0.9	High Similarity	NPC472905
0.9	High Similarity	NPC95842
0.9	High Similarity	NPC160951
0.9	High Similarity	NPC476631
0.8994	High Similarity	NPC154345
0.8982	High Similarity	NPC124470
0.8982	High Similarity	NPC109827
0.897	High Similarity	NPC26386
0.897	High Similarity	NPC326520
0.897	High Similarity	NPC259757
0.8963	High Similarity	NPC201800
0.8963	High Similarity	NPC8300
0.8957	High Similarity	NPC475784
0.8957	High Similarity	NPC246478
0.8957	High Similarity	NPC474287
0.8957	High Similarity	NPC188433
0.8957	High Similarity	NPC84571
0.8957	High Similarity	NPC475886
0.8951	High Similarity	NPC469584
0.8951	High Similarity	NPC36852
0.8951	High Similarity	NPC472913
0.8951	High Similarity	NPC472910
0.8951	High Similarity	NPC27337
0.8951	High Similarity	NPC472911
0.8951	High Similarity	NPC473272
0.8951	High Similarity	NPC223787
0.8951	High Similarity	NPC52889
0.8951	High Similarity	NPC472914
0.8951	High Similarity	NPC284820
0.8951	High Similarity	NPC245758
0.8951	High Similarity	NPC96167
0.8951	High Similarity	NPC222814
0.8951	High Similarity	NPC472963
0.8951	High Similarity	NPC262286
0.8944	High Similarity	NPC213622
0.8944	High Similarity	NPC201136

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 NPC476637 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	430
0.1-0.2	1022
0.2-0.3	1759
0.3-0.4	2733
0.4-0.5	1771
0.5-0.6	888
0.6-0.7	378
0.7-0.8	131
0.8-0.85	26
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD2801	Approved
0.8765	High Similarity	NPD2393	Clinical (unspecified phase)
0.8704	High Similarity	NPD1934	Approved
0.8671	High Similarity	NPD1511	Approved
0.858	High Similarity	NPD7473	Discontinued
0.8562	High Similarity	NPD1512	Approved
0.8521	High Similarity	NPD6168	Clinical (unspecified phase)
0.8521	High Similarity	NPD6167	Clinical (unspecified phase)
0.8521	High Similarity	NPD6166	Phase 2
0.8512	High Similarity	NPD6232	Discontinued
0.8503	High Similarity	NPD5494	Approved
0.848	Intermediate Similarity	NPD5844	Phase 1
0.8385	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD7054	Approved
0.8343	Intermediate Similarity	NPD6959	Discontinued
0.8324	Intermediate Similarity	NPD7074	Phase 3
0.8324	Intermediate Similarity	NPD7472	Approved
0.8323	Intermediate Similarity	NPD3882	Suspended
0.8272	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD3817	Phase 2
0.8242	Intermediate Similarity	NPD4380	Phase 2
0.8208	Intermediate Similarity	NPD3818	Discontinued
0.8182	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6797	Phase 2
0.8125	Intermediate Similarity	NPD7251	Discontinued
0.8111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD1465	Phase 2
0.8079	Intermediate Similarity	NPD7808	Phase 3
0.8047	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7075	Discontinued
0.7901	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7390	Discontinued
0.784	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD5402	Approved
0.7831	Intermediate Similarity	NPD2532	Approved
0.7831	Intermediate Similarity	NPD2534	Approved
0.7831	Intermediate Similarity	NPD2533	Approved
0.7826	Intermediate Similarity	NPD1510	Phase 2
0.7826	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6801	Discontinued
0.7816	Intermediate Similarity	NPD1247	Approved
0.7812	Intermediate Similarity	NPD1607	Approved
0.7811	Intermediate Similarity	NPD6599	Discontinued
0.7791	Intermediate Similarity	NPD1549	Phase 2
0.7778	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD2796	Approved
0.7778	Intermediate Similarity	NPD6099	Approved
0.7765	Intermediate Similarity	NPD7411	Suspended
0.7751	Intermediate Similarity	NPD3226	Approved
0.7746	Intermediate Similarity	NPD3749	Approved
0.7744	Intermediate Similarity	NPD2800	Approved
0.7722	Intermediate Similarity	NPD6559	Discontinued
0.7716	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3748	Approved
0.7688	Intermediate Similarity	NPD1240	Approved
0.7688	Intermediate Similarity	NPD943	Approved
0.7684	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2935	Discontinued
0.7667	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6799	Approved
0.7622	Intermediate Similarity	NPD2346	Discontinued
0.7609	Intermediate Similarity	NPD8150	Discontinued
0.76	Intermediate Similarity	NPD6234	Discontinued
0.76	Intermediate Similarity	NPD919	Approved
0.7598	Intermediate Similarity	NPD3751	Discontinued
0.759	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7768	Phase 2
0.7554	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8312	Approved
0.7541	Intermediate Similarity	NPD8313	Approved
0.7539	Intermediate Similarity	NPD6777	Approved
0.7539	Intermediate Similarity	NPD6776	Approved
0.7539	Intermediate Similarity	NPD6780	Approved
0.7539	Intermediate Similarity	NPD6781	Approved
0.7539	Intermediate Similarity	NPD6782	Approved
0.7539	Intermediate Similarity	NPD6779	Approved
0.7539	Intermediate Similarity	NPD6778	Approved
0.7529	Intermediate Similarity	NPD5403	Approved
0.7528	Intermediate Similarity	NPD3926	Phase 2
0.7515	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD7228	Approved
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD3787	Discontinued
0.7448	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7435	Discontinued
0.7414	Intermediate Similarity	NPD37	Approved
0.7412	Intermediate Similarity	NPD5401	Approved
0.7394	Intermediate Similarity	NPD2799	Discontinued
0.7391	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4965	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7381	Intermediate Similarity	NPD4628	Phase 3
0.7378	Intermediate Similarity	NPD6651	Approved
0.7362	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1613	Approved
0.7349	Intermediate Similarity	NPD1551	Phase 2
0.7337	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7783	Phase 2
0.7333	Intermediate Similarity	NPD7697	Approved
0.7333	Intermediate Similarity	NPD7696	Phase 3
0.7333	Intermediate Similarity	NPD7698	Approved
0.7326	Intermediate Similarity	NPD8434	Phase 2
0.7326	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1243	Approved
0.7317	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD7870	Phase 2
0.7296	Intermediate Similarity	NPD7871	Phase 2
0.7294	Intermediate Similarity	NPD3300	Phase 2
0.7284	Intermediate Similarity	NPD3027	Phase 3
0.7282	Intermediate Similarity	NPD6823	Phase 2
0.7278	Intermediate Similarity	NPD5710	Approved
0.7278	Intermediate Similarity	NPD5711	Approved
0.7277	Intermediate Similarity	NPD6535	Approved
0.7277	Intermediate Similarity	NPD6534	Approved
0.7273	Intermediate Similarity	NPD7701	Phase 2
0.725	Intermediate Similarity	NPD7801	Approved
0.7246	Intermediate Similarity	NPD5404	Approved
0.7246	Intermediate Similarity	NPD5406	Approved
0.7246	Intermediate Similarity	NPD5408	Approved
0.7246	Intermediate Similarity	NPD5405	Approved
0.7241	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7458	Discontinued
0.7239	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2313	Discontinued
0.7236	Intermediate Similarity	NPD8151	Discontinued
0.7233	Intermediate Similarity	NPD4749	Approved
0.7225	Intermediate Similarity	NPD920	Approved
0.7212	Intermediate Similarity	NPD230	Phase 1
0.7202	Intermediate Similarity	NPD2344	Approved
0.72	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7874	Approved
0.7188	Intermediate Similarity	NPD4360	Phase 2
0.7188	Intermediate Similarity	NPD4363	Phase 3
0.7184	Intermediate Similarity	NPD1653	Approved
0.7176	Intermediate Similarity	NPD7003	Approved
0.7165	Intermediate Similarity	NPD7699	Phase 2
0.7165	Intermediate Similarity	NPD7700	Phase 2
0.7151	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7135	Intermediate Similarity	NPD4288	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4908	Phase 1
0.7112	Intermediate Similarity	NPD7549	Discontinued
0.711	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1201	Approved
0.7099	Intermediate Similarity	NPD2798	Approved
0.7097	Intermediate Similarity	NPD5953	Discontinued
0.7093	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7229	Phase 3
0.7083	Intermediate Similarity	NPD4308	Phase 3
0.7081	Intermediate Similarity	NPD7286	Phase 2
0.7076	Intermediate Similarity	NPD8166	Discontinued
0.7059	Intermediate Similarity	NPD7240	Approved
0.7048	Intermediate Similarity	NPD4060	Phase 1
0.7037	Intermediate Similarity	NPD1470	Approved
0.7037	Intermediate Similarity	NPD2797	Approved
0.7035	Intermediate Similarity	NPD2309	Approved
0.7035	Intermediate Similarity	NPD6190	Approved
0.703	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6674	Discontinued
0.7011	Intermediate Similarity	NPD2403	Approved
0.7006	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1933	Approved
0.7006	Intermediate Similarity	NPD5124	Phase 1
0.7005	Intermediate Similarity	NPD4111	Phase 1
0.7005	Intermediate Similarity	NPD4665	Approved
0.6977	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4361	Phase 2
0.6965	Remote Similarity	NPD7584	Approved
0.6959	Remote Similarity	NPD6213	Phase 3
0.6959	Remote Similarity	NPD6212	Phase 3
0.6959	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1608	Approved
0.6951	Remote Similarity	NPD9494	Approved
0.695	Remote Similarity	NPD8320	Phase 1
0.695	Remote Similarity	NPD8319	Approved
0.694	Remote Similarity	NPD8127	Discontinued
0.6938	Remote Similarity	NPD7907	Approved
0.6935	Remote Similarity	NPD7177	Discontinued
0.6933	Remote Similarity	NPD1203	Approved
0.6919	Remote Similarity	NPD5698	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data