NPASS Compound

Structure

NPC475805 OpenBabel07101718182D 32 37 0 0 1 0 0 0 0 0999 V2000 -8.1010 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6010 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7957 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1554 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3766 2.0438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.1421 1.7695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6849 1.6163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6010 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8544 2.4713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1579 2.1547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6010 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 24 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 16 2 0 0 0 0 10 21 1 0 0 0 0 11 20 1 0 0 0 0 11 22 2 0 0 0 0 12 17 1 0 0 0 0 12 25 1 0 0 0 0 13 18 1 0 0 0 0 13 26 1 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 15 23 2 0 0 0 0 15 28 1 0 0 0 0 16 31 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 20 29 2 0 0 0 0 21 30 1 0 0 0 0 22 30 1 0 0 0 0 23 32 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.14
Volume:	427.421
LogP:	5.981
LogD:	3.742
LogS:	-3.421
# Rotatable Bonds:	0
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.475
Synthetic Accessibility Score:	4.116
Fsp3:	0.32
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:	-5.054
MDCK Permeability:	1.6099074855446815e-05
Pgp-inhibitor:	0.658
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.297
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	99.83378601074219%
Volume Distribution (VD):	0.388
Pgp-substrate:	1.9570671319961548%

ADMET: Metabolism

CYP1A2-inhibitor:	0.431
CYP1A2-substrate:	0.51
CYP2C19-inhibitor:	0.201
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.863
CYP2D6-inhibitor:	0.161
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.183
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	1.725
Half-life (T1/2):	0.157

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.947
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.449
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.169
Carcinogencity:	0.806
Eye Corrosion:	0.003
Eye Irritation:	0.196
Respiratory Toxicity:	0.595

Download Data

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

Natural Product: NPC475805

Natural Product ID:	NPC475805
*Common Name:**	Cycloartobiloxanthone
IUPAC Name:	n.a.
Synonyms:	Cycloartobiloxanthone
Standard InCHIKey:	OCZFLOUWXXGBPC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H22O7/c1-24(2)6-5-10-16(31-24)9-14(27)19-20(29)11-7-12-17-18(22(11)30-21(10)19)13(26)8-15(28)23(17)32-25(12,3)4/h5-6,8-9,12,26-28H,7H2,1-4H3
SMILES:	Oc1cc(O)c2c3c1c1oc4c5C=CC(Oc5cc(c4c(=O)c1CC3C(O2)(C)C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516519
PubChem CID:	10342859
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:0003521] Pyranoxanthones

*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
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384315]
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	Stems	n.a.	n.a.	PMID[29227656]

☑ 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	3
IC50	2

Activity Type	# Activity
Cell Line	3
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	7.2	ug ml-1	PMID[567374]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	7.7	ug ml-1	PMID[567374]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	IC50	>	10000.0	nM	PMID[567375]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	3.7	nM	PMID[567375]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	10000.0	nM	PMID[567375]

☑ 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 NPC475805 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	476
0.1-0.2	2041
0.2-0.3	4399
0.3-0.4	11407
0.4-0.5	6755
0.5-0.6	3914
0.6-0.7	5419
0.7-0.8	5397
0.8-0.85	1947
0.85-0.9	803
0.9-0.95	127
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC101107
0.975	High Similarity	NPC476637
0.9688	High Similarity	NPC126204
0.9686	High Similarity	NPC156432
0.9383	High Similarity	NPC472449
0.9383	High Similarity	NPC37870
0.9379	High Similarity	NPC189473
0.9379	High Similarity	NPC23298
0.9375	High Similarity	NPC278427
0.9321	High Similarity	NPC239752
0.9321	High Similarity	NPC275780
0.9321	High Similarity	NPC472450
0.9264	High Similarity	NPC39091
0.9259	High Similarity	NPC207690
0.9259	High Similarity	NPC146134
0.9255	High Similarity	NPC259456
0.9245	High Similarity	NPC471985
0.9245	High Similarity	NPC276444
0.9202	High Similarity	NPC303174
0.9198	High Similarity	NPC261470
0.9198	High Similarity	NPC229632
0.9198	High Similarity	NPC329760
0.9198	High Similarity	NPC25152
0.9193	High Similarity	NPC471973
0.9193	High Similarity	NPC204290
0.9193	High Similarity	NPC139036
0.9187	High Similarity	NPC476630
0.9187	High Similarity	NPC218871
0.9162	High Similarity	NPC227906
0.9152	High Similarity	NPC188079
0.9146	High Similarity	NPC170245
0.9146	High Similarity	NPC43319
0.9146	High Similarity	NPC272502
0.9141	High Similarity	NPC186686
0.9141	High Similarity	NPC306321
0.9141	High Similarity	NPC270837
0.9141	High Similarity	NPC236521
0.9141	High Similarity	NPC152659
0.9141	High Similarity	NPC248638
0.9141	High Similarity	NPC303460
0.9136	High Similarity	NPC29876
0.9136	High Similarity	NPC167678
0.9136	High Similarity	NPC40037
0.9136	High Similarity	NPC61010
0.913	High Similarity	NPC474290
0.913	High Similarity	NPC100123
0.913	High Similarity	NPC197856
0.913	High Similarity	NPC280680
0.9119	High Similarity	NPC170492
0.9096	High Similarity	NPC472276
0.9091	High Similarity	NPC218226
0.9091	High Similarity	NPC476306
0.9085	High Similarity	NPC326520
0.9085	High Similarity	NPC50960
0.908	High Similarity	NPC78332
0.908	High Similarity	NPC52204
0.908	High Similarity	NPC294965
0.908	High Similarity	NPC474162
0.908	High Similarity	NPC474150
0.908	High Similarity	NPC472402
0.908	High Similarity	NPC83922
0.908	High Similarity	NPC194427
0.908	High Similarity	NPC206605
0.908	High Similarity	NPC472448
0.9074	High Similarity	NPC476980
0.9074	High Similarity	NPC14353
0.9074	High Similarity	NPC228785
0.9074	High Similarity	NPC200746
0.9074	High Similarity	NPC320359
0.9074	High Similarity	NPC80375
0.9074	High Similarity	NPC56085
0.9074	High Similarity	NPC476280
0.9068	High Similarity	NPC136674
0.9062	High Similarity	NPC166054
0.9062	High Similarity	NPC55662
0.9036	High Similarity	NPC165456
0.903	High Similarity	NPC472452
0.903	High Similarity	NPC120593
0.9024	High Similarity	NPC475985
0.9024	High Similarity	NPC236132
0.9024	High Similarity	NPC220313
0.9024	High Similarity	NPC12461
0.9018	High Similarity	NPC66288
0.9018	High Similarity	NPC40491
0.9018	High Similarity	NPC278052
0.9018	High Similarity	NPC198829
0.9012	High Similarity	NPC476242
0.9012	High Similarity	NPC46736
0.9012	High Similarity	NPC74178
0.9012	High Similarity	NPC184755
0.9006	High Similarity	NPC68093
0.9006	High Similarity	NPC142339
0.9006	High Similarity	NPC274730
0.9006	High Similarity	NPC191146
0.8994	High Similarity	NPC216307
0.8988	High Similarity	NPC310794
0.8976	High Similarity	NPC477154
0.8976	High Similarity	NPC6588
0.8976	High Similarity	NPC117854
0.897	High Similarity	NPC130920
0.897	High Similarity	NPC85057
0.897	High Similarity	NPC293319
0.8963	High Similarity	NPC81679
0.8957	High Similarity	NPC472624
0.8957	High Similarity	NPC188433
0.8957	High Similarity	NPC297212
0.8957	High Similarity	NPC118256
0.8957	High Similarity	NPC192686
0.8957	High Similarity	NPC36217
0.8957	High Similarity	NPC119224
0.8957	High Similarity	NPC119209
0.8957	High Similarity	NPC235018
0.8957	High Similarity	NPC45146
0.8957	High Similarity	NPC328102
0.8957	High Similarity	NPC474960
0.8951	High Similarity	NPC78225
0.8951	High Similarity	NPC217677
0.8951	High Similarity	NPC237418
0.8951	High Similarity	NPC273843
0.8951	High Similarity	NPC218313
0.8951	High Similarity	NPC241904
0.8951	High Similarity	NPC476981
0.8951	High Similarity	NPC236796
0.8951	High Similarity	NPC300727
0.8951	High Similarity	NPC165977
0.8951	High Similarity	NPC474681
0.8944	High Similarity	NPC200246
0.8944	High Similarity	NPC472280
0.8944	High Similarity	NPC234255
0.8938	High Similarity	NPC237994
0.8938	High Similarity	NPC471982
0.8938	High Similarity	NPC249570
0.8931	High Similarity	NPC88804
0.8931	High Similarity	NPC3825
0.8929	High Similarity	NPC223375
0.8929	High Similarity	NPC475825
0.8929	High Similarity	NPC4200
0.8922	High Similarity	NPC288813
0.8922	High Similarity	NPC177480
0.8916	High Similarity	NPC173292
0.8916	High Similarity	NPC235610
0.8909	High Similarity	NPC7483
0.8909	High Similarity	NPC273959
0.8902	High Similarity	NPC32694
0.8902	High Similarity	NPC258331
0.8902	High Similarity	NPC234644
0.8902	High Similarity	NPC474038
0.8902	High Similarity	NPC472906
0.8902	High Similarity	NPC266314
0.8902	High Similarity	NPC474187
0.8902	High Similarity	NPC57715
0.8896	High Similarity	NPC204879
0.8896	High Similarity	NPC469658
0.8896	High Similarity	NPC235448
0.8895	High Similarity	NPC150977
0.8889	High Similarity	NPC470600
0.8889	High Similarity	NPC472455
0.8889	High Similarity	NPC282307
0.8889	High Similarity	NPC170026
0.8889	High Similarity	NPC472907
0.8889	High Similarity	NPC475799
0.8889	High Similarity	NPC474167
0.8889	High Similarity	NPC133970
0.8889	High Similarity	NPC5322
0.8889	High Similarity	NPC138243
0.8889	High Similarity	NPC13779
0.8889	High Similarity	NPC6633
0.8889	High Similarity	NPC470762
0.8882	High Similarity	NPC255350
0.8882	High Similarity	NPC22519
0.8882	High Similarity	NPC472905
0.8882	High Similarity	NPC183878
0.8882	High Similarity	NPC145379
0.8882	High Similarity	NPC95842
0.8882	High Similarity	NPC178964
0.8882	High Similarity	NPC280530
0.8882	High Similarity	NPC69394
0.8882	High Similarity	NPC231018
0.8882	High Similarity	NPC274327
0.8882	High Similarity	NPC47781
0.8882	High Similarity	NPC89474
0.8882	High Similarity	NPC176775
0.8882	High Similarity	NPC160951
0.8882	High Similarity	NPC476631
0.8875	High Similarity	NPC154345
0.8862	High Similarity	NPC150131
0.8862	High Similarity	NPC8965
0.8862	High Similarity	NPC474024
0.8855	High Similarity	NPC259757
0.8855	High Similarity	NPC473286
0.8855	High Similarity	NPC25361
0.8848	High Similarity	NPC8300
0.8848	High Similarity	NPC472635
0.8848	High Similarity	NPC201800
0.8848	High Similarity	NPC470694
0.8844	High Similarity	NPC476170
0.8841	High Similarity	NPC161947
0.8841	High Similarity	NPC475886
0.8841	High Similarity	NPC155302
0.8841	High Similarity	NPC475784

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 NPC475805 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	414
0.1-0.2	1034
0.2-0.3	1830
0.3-0.4	2826
0.4-0.5	1714
0.5-0.6	872
0.6-0.7	309
0.7-0.8	124
0.8-0.85	23
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8882	High Similarity	NPD2801	Approved
0.865	High Similarity	NPD2393	Clinical (unspecified phase)
0.8614	High Similarity	NPD5494	Approved
0.8589	High Similarity	NPD1934	Approved
0.8553	High Similarity	NPD1511	Approved
0.8447	Intermediate Similarity	NPD1512	Approved
0.8434	Intermediate Similarity	NPD3882	Suspended
0.8412	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD6166	Phase 2
0.8412	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD7473	Discontinued
0.8314	Intermediate Similarity	NPD3818	Discontinued
0.8294	Intermediate Similarity	NPD6232	Discontinued
0.8272	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD7054	Approved
0.8266	Intermediate Similarity	NPD5844	Phase 1
0.8235	Intermediate Similarity	NPD6959	Discontinued
0.8218	Intermediate Similarity	NPD7074	Phase 3
0.8218	Intermediate Similarity	NPD7472	Approved
0.816	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD3817	Phase 2
0.8133	Intermediate Similarity	NPD4380	Phase 2
0.8095	Intermediate Similarity	NPD1465	Phase 2
0.8079	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD6797	Phase 2
0.8023	Intermediate Similarity	NPD7251	Discontinued
0.7988	Intermediate Similarity	NPD7819	Suspended
0.7978	Intermediate Similarity	NPD7808	Phase 3
0.7963	Intermediate Similarity	NPD2800	Approved
0.7941	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1247	Approved
0.7914	Intermediate Similarity	NPD3750	Approved
0.7912	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD3749	Approved
0.7849	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7075	Discontinued
0.7831	Intermediate Similarity	NPD2532	Approved
0.7831	Intermediate Similarity	NPD2534	Approved
0.7831	Intermediate Similarity	NPD2533	Approved
0.7824	Intermediate Similarity	NPD6801	Discontinued
0.7791	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5402	Approved
0.773	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6559	Discontinued
0.7716	Intermediate Similarity	NPD1510	Phase 2
0.7701	Intermediate Similarity	NPD6234	Discontinued
0.7701	Intermediate Similarity	NPD919	Approved
0.7683	Intermediate Similarity	NPD1549	Phase 2
0.7669	Intermediate Similarity	NPD2796	Approved
0.7665	Intermediate Similarity	NPD7390	Discontinued
0.7661	Intermediate Similarity	NPD7411	Suspended
0.765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD3926	Phase 2
0.7614	Intermediate Similarity	NPD7199	Phase 2
0.7607	Intermediate Similarity	NPD3748	Approved
0.7602	Intermediate Similarity	NPD6599	Discontinued
0.7598	Intermediate Similarity	NPD7228	Approved
0.7593	Intermediate Similarity	NPD1607	Approved
0.7584	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD943	Approved
0.7578	Intermediate Similarity	NPD1240	Approved
0.7569	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2935	Discontinued
0.7561	Intermediate Similarity	NPD6099	Approved
0.7561	Intermediate Similarity	NPD6100	Approved
0.756	Intermediate Similarity	NPD6799	Approved
0.7544	Intermediate Similarity	NPD3226	Approved
0.7528	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4965	Approved
0.7486	Intermediate Similarity	NPD4966	Approved
0.7486	Intermediate Similarity	NPD4967	Phase 2
0.7486	Intermediate Similarity	NPD7768	Phase 2
0.7438	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD920	Approved
0.7427	Intermediate Similarity	NPD5403	Approved
0.7425	Intermediate Similarity	NPD1243	Approved
0.7419	Intermediate Similarity	NPD8434	Phase 2
0.7419	Intermediate Similarity	NPD8150	Discontinued
0.741	Intermediate Similarity	NPD2346	Discontinued
0.7394	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6651	Approved
0.7375	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD3787	Discontinued
0.7358	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6777	Approved
0.7358	Intermediate Similarity	NPD6778	Approved
0.7358	Intermediate Similarity	NPD6776	Approved
0.7358	Intermediate Similarity	NPD6779	Approved
0.7358	Intermediate Similarity	NPD6782	Approved
0.7358	Intermediate Similarity	NPD6781	Approved
0.7358	Intermediate Similarity	NPD6780	Approved
0.7351	Intermediate Similarity	NPD8312	Approved
0.7351	Intermediate Similarity	NPD8313	Approved
0.731	Intermediate Similarity	NPD5401	Approved
0.731	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2344	Approved
0.7289	Intermediate Similarity	NPD2799	Discontinued
0.7284	Intermediate Similarity	NPD4625	Phase 3
0.7278	Intermediate Similarity	NPD5711	Approved
0.7278	Intermediate Similarity	NPD5710	Approved
0.7256	Intermediate Similarity	NPD1613	Approved
0.7256	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7435	Discontinued
0.7219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD447	Suspended
0.7209	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD2403	Approved
0.7193	Intermediate Similarity	NPD3300	Phase 2
0.7193	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7229	Phase 3
0.7178	Intermediate Similarity	NPD3027	Phase 3
0.7176	Intermediate Similarity	NPD4628	Phase 3
0.7164	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7783	Phase 2
0.7157	Intermediate Similarity	NPD7697	Approved
0.7157	Intermediate Similarity	NPD7698	Approved
0.7157	Intermediate Similarity	NPD7696	Phase 3
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7151	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7135	Intermediate Similarity	NPD2309	Approved
0.7134	Intermediate Similarity	NPD2313	Discontinued
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7871	Phase 2
0.7121	Intermediate Similarity	NPD7870	Phase 2
0.7108	Intermediate Similarity	NPD230	Phase 1
0.7107	Intermediate Similarity	NPD6823	Phase 2
0.71	Intermediate Similarity	NPD7701	Phase 2
0.7098	Intermediate Similarity	NPD6534	Approved
0.7098	Intermediate Similarity	NPD6535	Approved
0.7098	Intermediate Similarity	NPD4360	Phase 2
0.7098	Intermediate Similarity	NPD4363	Phase 3
0.7087	Intermediate Similarity	NPD4665	Approved
0.7087	Intermediate Similarity	NPD4111	Phase 1
0.7086	Intermediate Similarity	NPD1653	Approved
0.7081	Intermediate Similarity	NPD7286	Phase 2
0.7079	Intermediate Similarity	NPD7801	Approved
0.7065	Intermediate Similarity	NPD8151	Discontinued
0.7062	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4361	Phase 2
0.7045	Intermediate Similarity	NPD7458	Discontinued
0.7045	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5406	Approved
0.7041	Intermediate Similarity	NPD5404	Approved
0.7041	Intermediate Similarity	NPD5405	Approved
0.7041	Intermediate Similarity	NPD5408	Approved
0.7039	Intermediate Similarity	NPD4288	Approved
0.703	Intermediate Similarity	NPD3268	Approved
0.703	Intermediate Similarity	NPD7874	Approved
0.703	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7549	Discontinued
0.7019	Intermediate Similarity	NPD4749	Approved
0.7019	Intermediate Similarity	NPD7907	Approved
0.7012	Intermediate Similarity	NPD4908	Phase 1
0.7011	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7028	Phase 2
0.7005	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD1201	Approved
0.7	Intermediate Similarity	NPD1471	Phase 3
0.6994	Remote Similarity	NPD2798	Approved
0.699	Remote Similarity	NPD7699	Phase 2
0.699	Remote Similarity	NPD7700	Phase 2
0.6979	Remote Similarity	NPD4287	Approved
0.6977	Remote Similarity	NPD8166	Discontinued
0.6977	Remote Similarity	NPD7003	Approved
0.6975	Remote Similarity	NPD6696	Suspended
0.697	Remote Similarity	NPD2494	Approved
0.697	Remote Similarity	NPD2493	Approved
0.695	Remote Similarity	NPD4583	Approved
0.695	Remote Similarity	NPD4582	Approved
0.6947	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4060	Phase 1
0.694	Remote Similarity	NPD8127	Discontinued
0.6939	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6190	Approved
0.6933	Remote Similarity	NPD2797	Approved
0.6933	Remote Similarity	NPD1470	Approved
0.6928	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5124	Phase 1
0.6905	Remote Similarity	NPD1933	Approved
0.6905	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4004	Approved
0.69	Remote Similarity	NPD4002	Approved
0.6889	Remote Similarity	NPD5761	Phase 2
0.6889	Remote Similarity	NPD5760	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