NPASS Compound

Structure

NPC126204 OpenBabel07101719252D 37 41 0 0 1 0 0 0 0 0999 V2000 0.4684 -4.4126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2258 -4.7727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3331 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1991 -0.5000 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 0.0526 -2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6906 -3.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4670 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6010 -1.0000 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 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 5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4827 -4.1036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3331 -1.0000 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 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 1 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 2.1421 1.7695 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 5.0029 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 5.8690 -1.0000 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 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 0.5878 -0.8090 0.0000 C 0 0 1 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 2.8544 2.4713 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 5.8690 -2.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 14 2 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 16 1 0 0 0 0 10 30 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 19 2 0 0 0 0 13 22 1 0 0 0 0 16 19 1 0 0 0 0 16 26 2 0 0 0 0 17 27 1 0 0 0 0 17 28 2 0 0 0 0 18 23 1 0 0 0 0 18 30 1 6 0 0 0 19 31 1 0 0 0 0 20 24 1 0 0 0 0 20 32 1 0 0 0 0 21 29 2 0 0 0 0 21 33 1 0 0 0 0 22 25 2 0 0 0 0 22 36 1 0 0 0 0 23 24 2 0 0 0 0 23 29 1 0 0 0 0 24 28 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 26 34 1 0 0 0 0 27 35 2 0 0 0 0 28 36 1 0 0 0 0 29 37 1 0 0 0 0 30 5 1 6 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.21
Volume:	519.821
LogP:	7.462
LogD:	3.635
LogS:	-2.546
# Rotatable Bonds:	5
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	4.44
Fsp3:	0.367
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.009
MDCK Permeability:	1.1754954357456882e-05
Pgp-inhibitor:	0.839
Pgp-substrate:	0.952
Human Intestinal Absorption (HIA):	0.765
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	92.84473419189453%
Volume Distribution (VD):	0.922
Pgp-substrate:	10.98277759552002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.31
CYP1A2-substrate:	0.225
CYP2C19-inhibitor:	0.639
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.76
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.431
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.118
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	4.016
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.943
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.39
Rat Oral Acute Toxicity:	0.649
Maximum Recommended Daily Dose:	0.606
Skin Sensitization:	0.748
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.763
Respiratory Toxicity:	0.186

Download Data

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

Natural Product: NPC126204

Natural Product ID:	NPC126204
*Common Name:**	Artorigidin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NNOHQDGLBSBWNG-YVGXBJCXSA-N
Standard InCHI:	InChI=1S/C30H32O7/c1-14(2)7-6-10-30(5)18-11-17-27(35)25-22(13-19(31)16(26(25)34)9-8-15(3)4)36-28(17)24-20(32)12-21(33)29(37-30)23(18)24/h7-8,12-13,18,31-34H,6,9-11H2,1-5H3/t18-,30+/m0/s1
SMILES:	CC(=CCC[C@@]1(C)Oc2c3[C@@H]1Cc1c(=O)c4c(oc1c3c(cc2O)O)cc(c(c4O)CC=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094757
PubChem CID:	46834558
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
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	3.4	nM	PMID[511227]

☑ 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 NPC126204 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	464
0.1-0.2	1930
0.2-0.3	4062
0.3-0.4	10447
0.4-0.5	7854
0.5-0.6	3726
0.6-0.7	5157
0.7-0.8	5448
0.8-0.85	2202
0.85-0.9	1071
0.9-0.95	282
0.95-1	54

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC101107
0.9688	High Similarity	NPC475805
0.9682	High Similarity	NPC278427
0.9565	High Similarity	NPC476637
0.95	High Similarity	NPC156432
0.9441	High Similarity	NPC39091
0.9441	High Similarity	NPC37870
0.9437	High Similarity	NPC189473
0.9437	High Similarity	NPC23298
0.9379	High Similarity	NPC472450
0.9379	High Similarity	NPC239752
0.9379	High Similarity	NPC275780
0.9375	High Similarity	NPC25152
0.9371	High Similarity	NPC320359
0.9333	High Similarity	NPC227906
0.9321	High Similarity	NPC472449
0.9321	High Similarity	NPC170245
0.9317	High Similarity	NPC236521
0.9317	High Similarity	NPC152659
0.9317	High Similarity	NPC236132
0.9317	High Similarity	NPC270837
0.9317	High Similarity	NPC207690
0.9317	High Similarity	NPC248638
0.9313	High Similarity	NPC40491
0.9313	High Similarity	NPC61010
0.9313	High Similarity	NPC278052
0.9308	High Similarity	NPC100123
0.9264	High Similarity	NPC218226
0.9259	High Similarity	NPC326520
0.9255	High Similarity	NPC229632
0.9255	High Similarity	NPC329760
0.9255	High Similarity	NPC294965
0.925	High Similarity	NPC56085
0.925	High Similarity	NPC228785
0.925	High Similarity	NPC139036
0.925	High Similarity	NPC471973
0.925	High Similarity	NPC204290
0.925	High Similarity	NPC119224
0.925	High Similarity	NPC200746
0.925	High Similarity	NPC14353
0.9245	High Similarity	NPC476630
0.9245	High Similarity	NPC218871
0.9245	High Similarity	NPC236796
0.9236	High Similarity	NPC249570
0.9202	High Similarity	NPC43319
0.9198	High Similarity	NPC475985
0.9198	High Similarity	NPC7483
0.9198	High Similarity	NPC186686
0.9198	High Similarity	NPC146134
0.9193	High Similarity	NPC259456
0.9193	High Similarity	NPC167678
0.9193	High Similarity	NPC29876
0.9193	High Similarity	NPC66288
0.9187	High Similarity	NPC474290
0.9187	High Similarity	NPC197856
0.9187	High Similarity	NPC476242
0.9182	High Similarity	NPC274730
0.9182	High Similarity	NPC142339
0.9182	High Similarity	NPC13779
0.9182	High Similarity	NPC475799
0.9182	High Similarity	NPC276444
0.9182	High Similarity	NPC471985
0.9177	High Similarity	NPC476631
0.9146	High Similarity	NPC477154
0.9146	High Similarity	NPC6588
0.9146	High Similarity	NPC117854
0.9141	High Similarity	NPC293319
0.9141	High Similarity	NPC303174
0.9136	High Similarity	NPC474162
0.9136	High Similarity	NPC474150
0.9136	High Similarity	NPC83922
0.9136	High Similarity	NPC472448
0.9136	High Similarity	NPC81679
0.913	High Similarity	NPC476280
0.913	High Similarity	NPC476980
0.913	High Similarity	NPC474287
0.913	High Similarity	NPC475886
0.9125	High Similarity	NPC217677
0.9125	High Similarity	NPC273843
0.9125	High Similarity	NPC241904
0.9125	High Similarity	NPC300727
0.9125	High Similarity	NPC165977
0.9125	High Similarity	NPC136674
0.9114	High Similarity	NPC471982
0.9091	High Similarity	NPC188079
0.9085	High Similarity	NPC472452
0.908	High Similarity	NPC273959
0.908	High Similarity	NPC303460
0.908	High Similarity	NPC306321
0.908	High Similarity	NPC220313
0.9074	High Similarity	NPC474186
0.9074	High Similarity	NPC474351
0.9074	High Similarity	NPC475883
0.9074	High Similarity	NPC474187
0.9068	High Similarity	NPC46736
0.9068	High Similarity	NPC280680
0.9068	High Similarity	NPC469658
0.9062	High Similarity	NPC68093
0.9062	High Similarity	NPC472907
0.9062	High Similarity	NPC470762
0.9062	High Similarity	NPC474167
0.9062	High Similarity	NPC191146
0.9062	High Similarity	NPC138243
0.9059	High Similarity	NPC150977
0.9057	High Similarity	NPC170492
0.9057	High Similarity	NPC89474
0.9048	High Similarity	NPC216307
0.9042	High Similarity	NPC310794
0.9036	High Similarity	NPC472276
0.903	High Similarity	NPC478060
0.903	High Similarity	NPC470377
0.903	High Similarity	NPC474024
0.903	High Similarity	NPC478059
0.903	High Similarity	NPC471975
0.903	High Similarity	NPC470374
0.903	High Similarity	NPC476306
0.9024	High Similarity	NPC473286
0.9024	High Similarity	NPC25361
0.9024	High Similarity	NPC39306
0.9018	High Similarity	NPC470694
0.9018	High Similarity	NPC52204
0.9018	High Similarity	NPC78332
0.9018	High Similarity	NPC472402
0.9018	High Similarity	NPC206605
0.9018	High Similarity	NPC261470
0.9018	High Similarity	NPC201800
0.9012	High Similarity	NPC118256
0.9012	High Similarity	NPC297212
0.9012	High Similarity	NPC45146
0.9012	High Similarity	NPC328102
0.9012	High Similarity	NPC119209
0.9012	High Similarity	NPC474960
0.9012	High Similarity	NPC246478
0.9012	High Similarity	NPC235018
0.9012	High Similarity	NPC80375
0.9012	High Similarity	NPC472624
0.9012	High Similarity	NPC192686
0.9012	High Similarity	NPC36217
0.9006	High Similarity	NPC36852
0.9006	High Similarity	NPC472963
0.9006	High Similarity	NPC237418
0.9006	High Similarity	NPC469584
0.9006	High Similarity	NPC223787
0.9006	High Similarity	NPC52889
0.9006	High Similarity	NPC476981
0.9006	High Similarity	NPC262286
0.9006	High Similarity	NPC78225
0.9006	High Similarity	NPC474681
0.9006	High Similarity	NPC218313
0.9	High Similarity	NPC472280
0.9	High Similarity	NPC234255
0.8994	High Similarity	NPC237994
0.8994	High Similarity	NPC23553
0.8994	High Similarity	NPC77179
0.8987	High Similarity	NPC88804
0.8987	High Similarity	NPC3825
0.8982	High Similarity	NPC475825
0.8982	High Similarity	NPC223375
0.8976	High Similarity	NPC165456
0.8976	High Similarity	NPC288813
0.897	High Similarity	NPC272502
0.897	High Similarity	NPC235610
0.897	High Similarity	NPC120593
0.897	High Similarity	NPC173292
0.897	High Similarity	NPC470462
0.8963	High Similarity	NPC41301
0.8963	High Similarity	NPC12461
0.8963	High Similarity	NPC133065
0.8963	High Similarity	NPC197168
0.8957	High Similarity	NPC474038
0.8957	High Similarity	NPC471212
0.8957	High Similarity	NPC258331
0.8957	High Similarity	NPC266314
0.8957	High Similarity	NPC471210
0.8957	High Similarity	NPC198829
0.8957	High Similarity	NPC32694
0.8957	High Similarity	NPC234644
0.8957	High Similarity	NPC471211
0.8957	High Similarity	NPC472906
0.8951	High Similarity	NPC85121
0.8951	High Similarity	NPC74178
0.8951	High Similarity	NPC184755
0.8951	High Similarity	NPC204879
0.8951	High Similarity	NPC210459
0.8951	High Similarity	NPC235448
0.8947	High Similarity	NPC246153
0.8944	High Similarity	NPC6633
0.8944	High Similarity	NPC209614
0.8944	High Similarity	NPC470328
0.8944	High Similarity	NPC472455
0.8944	High Similarity	NPC472626
0.8944	High Similarity	NPC133970
0.8944	High Similarity	NPC5322
0.8941	High Similarity	NPC476273
0.8938	High Similarity	NPC276409
0.8938	High Similarity	NPC472905
0.8938	High Similarity	NPC274327
0.8938	High Similarity	NPC69394
0.8938	High Similarity	NPC145379
0.8938	High Similarity	NPC255350

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 NPC126204 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	1011
0.2-0.3	1768
0.3-0.4	2764
0.4-0.5	1778
0.5-0.6	882
0.6-0.7	373
0.7-0.8	133
0.8-0.85	21
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8938	High Similarity	NPD2801	Approved
0.8704	High Similarity	NPD2393	Clinical (unspecified phase)
0.8667	High Similarity	NPD5494	Approved
0.8642	High Similarity	NPD1934	Approved
0.8608	High Similarity	NPD1511	Approved
0.8521	High Similarity	NPD7473	Discontinued
0.85	High Similarity	NPD1512	Approved
0.8485	Intermediate Similarity	NPD3882	Suspended
0.8363	Intermediate Similarity	NPD3818	Discontinued
0.8353	Intermediate Similarity	NPD6166	Phase 2
0.8353	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD7054	Approved
0.8314	Intermediate Similarity	NPD5844	Phase 1
0.8266	Intermediate Similarity	NPD7472	Approved
0.8266	Intermediate Similarity	NPD7074	Phase 3
0.821	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD3817	Phase 2
0.8182	Intermediate Similarity	NPD4380	Phase 2
0.8176	Intermediate Similarity	NPD6959	Discontinued
0.8144	Intermediate Similarity	NPD1465	Phase 2
0.8144	Intermediate Similarity	NPD7819	Suspended
0.8125	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7251	Discontinued
0.8047	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7808	Phase 3
0.8012	Intermediate Similarity	NPD2800	Approved
0.8011	Intermediate Similarity	NPD6797	Phase 2
0.8	Intermediate Similarity	NPD7075	Discontinued
0.7988	Intermediate Similarity	NPD2533	Approved
0.7988	Intermediate Similarity	NPD2534	Approved
0.7988	Intermediate Similarity	NPD2532	Approved
0.7965	Intermediate Similarity	NPD1247	Approved
0.7963	Intermediate Similarity	NPD3750	Approved
0.7956	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3749	Approved
0.7895	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD6099	Approved
0.7826	Intermediate Similarity	NPD6100	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6801	Discontinued
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7764	Intermediate Similarity	NPD1510	Phase 2
0.7746	Intermediate Similarity	NPD919	Approved
0.774	Intermediate Similarity	NPD7228	Approved
0.773	Intermediate Similarity	NPD1549	Phase 2
0.7716	Intermediate Similarity	NPD2796	Approved
0.7711	Intermediate Similarity	NPD7390	Discontinued
0.7706	Intermediate Similarity	NPD7411	Suspended
0.7676	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5402	Approved
0.767	Intermediate Similarity	NPD3926	Phase 2
0.7661	Intermediate Similarity	NPD37	Approved
0.7657	Intermediate Similarity	NPD7199	Phase 2
0.7654	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3748	Approved
0.7647	Intermediate Similarity	NPD6599	Discontinued
0.764	Intermediate Similarity	NPD1607	Approved
0.7636	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7768	Phase 2
0.763	Intermediate Similarity	NPD4967	Phase 2
0.763	Intermediate Similarity	NPD4965	Approved
0.763	Intermediate Similarity	NPD4966	Approved
0.7625	Intermediate Similarity	NPD943	Approved
0.7625	Intermediate Similarity	NPD1240	Approved
0.7611	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2935	Discontinued
0.7605	Intermediate Similarity	NPD6799	Approved
0.7588	Intermediate Similarity	NPD3226	Approved
0.7576	Intermediate Similarity	NPD1243	Approved
0.7571	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8434	Phase 2
0.7532	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6651	Approved
0.7528	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7456	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2346	Discontinued
0.7444	Intermediate Similarity	NPD3751	Discontinued
0.7439	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5711	Approved
0.7416	Intermediate Similarity	NPD5710	Approved
0.7391	Intermediate Similarity	NPD8313	Approved
0.7391	Intermediate Similarity	NPD8312	Approved
0.7368	Intermediate Similarity	NPD920	Approved
0.7368	Intermediate Similarity	NPD5403	Approved
0.7349	Intermediate Similarity	NPD2344	Approved
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.7329	Intermediate Similarity	NPD4625	Phase 3
0.7318	Intermediate Similarity	NPD7229	Phase 3
0.7318	Intermediate Similarity	NPD3787	Discontinued
0.7306	Intermediate Similarity	NPD6779	Approved
0.7306	Intermediate Similarity	NPD6782	Approved
0.7306	Intermediate Similarity	NPD6777	Approved
0.7306	Intermediate Similarity	NPD6776	Approved
0.7306	Intermediate Similarity	NPD6780	Approved
0.7306	Intermediate Similarity	NPD6778	Approved
0.7306	Intermediate Similarity	NPD6781	Approved
0.7301	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1613	Approved
0.7294	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7240	Approved
0.7283	Intermediate Similarity	NPD7685	Pre-registration
0.7282	Intermediate Similarity	NPD7435	Discontinued
0.7262	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD230	Phase 1
0.7256	Intermediate Similarity	NPD447	Suspended
0.7251	Intermediate Similarity	NPD5401	Approved
0.7251	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD2403	Approved
0.7235	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3300	Phase 2
0.7222	Intermediate Similarity	NPD3027	Phase 3
0.7219	Intermediate Similarity	NPD4628	Phase 3
0.72	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7783	Phase 2
0.7194	Intermediate Similarity	NPD7697	Approved
0.7194	Intermediate Similarity	NPD7696	Phase 3
0.7194	Intermediate Similarity	NPD7698	Approved
0.7186	Intermediate Similarity	NPD8151	Discontinued
0.7186	Intermediate Similarity	NPD1551	Phase 2
0.7178	Intermediate Similarity	NPD2313	Discontinued
0.7178	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2309	Approved
0.717	Intermediate Similarity	NPD4749	Approved
0.7166	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7870	Phase 2
0.7157	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7136	Intermediate Similarity	NPD7907	Approved
0.7136	Intermediate Similarity	NPD7701	Phase 2
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7126	Intermediate Similarity	NPD1653	Approved
0.7125	Intermediate Similarity	NPD6696	Suspended
0.7122	Intermediate Similarity	NPD4665	Approved
0.7122	Intermediate Similarity	NPD4111	Phase 1
0.712	Intermediate Similarity	NPD7286	Phase 2
0.7114	Intermediate Similarity	NPD7801	Approved
0.7098	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4361	Phase 2
0.7086	Intermediate Similarity	NPD7458	Discontinued
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5405	Approved
0.7083	Intermediate Similarity	NPD5404	Approved
0.7083	Intermediate Similarity	NPD5408	Approved
0.7083	Intermediate Similarity	NPD5406	Approved
0.7079	Intermediate Similarity	NPD4288	Approved
0.7073	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3268	Approved
0.7072	Intermediate Similarity	NPD8127	Discontinued
0.7065	Intermediate Similarity	NPD7874	Approved
0.7065	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6674	Discontinued
0.7055	Intermediate Similarity	NPD4908	Phase 1
0.7052	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6535	Approved
0.7047	Intermediate Similarity	NPD6534	Approved
0.7045	Intermediate Similarity	NPD7028	Phase 2
0.7044	Intermediate Similarity	NPD1201	Approved
0.7043	Intermediate Similarity	NPD5953	Discontinued
0.7041	Intermediate Similarity	NPD1471	Phase 3
0.7037	Intermediate Similarity	NPD2798	Approved
0.7026	Intermediate Similarity	NPD7699	Phase 2
0.7026	Intermediate Similarity	NPD7700	Phase 2
0.7022	Intermediate Similarity	NPD5760	Phase 2
0.7022	Intermediate Similarity	NPD5761	Phase 2
0.7018	Intermediate Similarity	NPD8166	Discontinued
0.7016	Intermediate Similarity	NPD4287	Approved
0.7005	Intermediate Similarity	NPD2494	Approved
0.7005	Intermediate Similarity	NPD2493	Approved
0.7	Intermediate Similarity	NPD7584	Approved
0.699	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4060	Phase 1
0.6985	Remote Similarity	NPD4582	Approved
0.6985	Remote Similarity	NPD4583	Approved
0.6977	Remote Similarity	NPD6190	Approved
0.6975	Remote Similarity	NPD2797	Approved
0.6975	Remote Similarity	NPD1470	Approved
0.697	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3764	Approved
0.6968	Remote Similarity	NPD7549	Discontinued
0.6957	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1933	Approved
0.6935	Remote Similarity	NPD4002	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