NPASS Compound

Structure

NPC472273 OpenBabel07101718302D 35 39 0 0 1 0 0 0 0 0999 V2000 -3.6133 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1236 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6359 0.9373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9338 0.7771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7472 0.1459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.1459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1236 1.9462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0288 1.1931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8838 2.8046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6118 3.2400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9483 1.5861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8587 2.5821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3709 1.2261 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1236 1.2261 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7472 2.3062 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7472 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3709 1.9462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4185 4.2212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7472 3.3062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 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 -0.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 5 1 0 0 0 0 5 16 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 17 1 0 0 0 0 8 18 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 4 1 1 0 0 0 13 14 1 0 0 0 0 14 11 1 1 0 0 0 15 12 1 1 0 0 0 15 19 1 0 0 0 0 15 34 1 0 0 0 0 16 24 1 6 0 0 0 16 26 1 0 0 0 0 17 24 1 6 0 0 0 17 25 1 0 0 0 0 18 26 1 1 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 6 0 0 0 20 21 1 0 0 0 0 20 31 1 1 0 0 0 21 22 1 0 0 0 0 21 32 1 6 0 0 0 22 34 1 0 0 0 0 22 35 1 1 0 0 0 23 25 1 0 0 0 0 23 33 2 0 0 0 0 23 35 1 0 0 0 0 24 1 1 6 0 0 0 25 2 1 1 0 0 0 26 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.28
Volume:	491.945
LogP:	0.94
LogD:	1.317
LogS:	-3.264
# Rotatable Bonds:	5
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	6.229
Fsp3:	0.962
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.735
MDCK Permeability:	9.297427459387109e-05
Pgp-inhibitor:	0.954
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.923
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.856

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	56.640567779541016%
Volume Distribution (VD):	0.446
Pgp-substrate:	21.74198341369629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.42
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.326
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	1.874
Half-life (T1/2):	0.726

ADMET: Toxicity

hERG Blockers:	0.132
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.71
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.909
Carcinogencity:	0.775
Eye Corrosion:	0.005
Eye Irritation:	0.039
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC472273

Natural Product ID:	NPC472273
*Common Name:**	ARWPYXKMKHEJGV-PJJQXYIRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ARWPYXKMKHEJGV-PJJQXYIRSA-N
Standard InCHI:	InChI=1S/C26H42O9/c1-24-6-3-7-25(2,23(33)35-22-21(32)20(31)19(30)15(12-28)34-22)17(24)8-18(29)26-9-13(4-5-16(24)26)14(10-26)11-27/h13-22,27-32H,3-12H2,1-2H3/t13-,14-,15-,16+,17+,18+,19-,20+,21-,22+,24+,25-,26-/m1/s1
SMILES:	CC12CCCC(C1CC(C34C2CCC(C3)C(C4)CO)O)(C)C(=O)OC5C(C(C(C(O5)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357410
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6333	Annona glabra	Species	Annonaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	30000.0	nM	PMID[469581]

☑ 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 NPC472273 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	456
0.1-0.2	3432
0.2-0.3	8215
0.3-0.4	12852
0.4-0.5	7237
0.5-0.6	4671
0.6-0.7	3207
0.7-0.8	2315
0.8-0.85	205
0.85-0.9	92
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9184	High Similarity	NPC203974
0.914	High Similarity	NPC215570
0.9091	High Similarity	NPC469826
0.9072	High Similarity	NPC34562
0.9	High Similarity	NPC236753
0.9	High Similarity	NPC228190
0.898	High Similarity	NPC469827
0.8958	High Similarity	NPC41843
0.8947	High Similarity	NPC471241
0.8866	High Similarity	NPC477172
0.8842	High Similarity	NPC475765
0.8842	High Similarity	NPC475785
0.883	High Similarity	NPC151214
0.883	High Similarity	NPC191915
0.8824	High Similarity	NPC469824
0.8812	High Similarity	NPC208333
0.8812	High Similarity	NPC469825
0.8812	High Similarity	NPC227879
0.8788	High Similarity	NPC470167
0.8776	High Similarity	NPC470172
0.8763	High Similarity	NPC20028
0.8738	High Similarity	NPC477489
0.8737	High Similarity	NPC94582
0.8737	High Similarity	NPC57964
0.8713	High Similarity	NPC230888
0.8713	High Similarity	NPC472079
0.8713	High Similarity	NPC88744
0.87	High Similarity	NPC215408
0.8687	High Similarity	NPC473406
0.8687	High Similarity	NPC107385
0.8646	High Similarity	NPC252056
0.8646	High Similarity	NPC203434
0.8646	High Similarity	NPC237071
0.8646	High Similarity	NPC296936
0.8646	High Similarity	NPC238796
0.8627	High Similarity	NPC91583
0.8627	High Similarity	NPC473844
0.8627	High Similarity	NPC240125
0.8627	High Similarity	NPC51947
0.8617	High Similarity	NPC475878
0.8614	High Similarity	NPC126753
0.8587	High Similarity	NPC43912
0.8587	High Similarity	NPC140446
0.8586	High Similarity	NPC471254
0.8586	High Similarity	NPC94919
0.8586	High Similarity	NPC80191
0.8586	High Similarity	NPC310031
0.8571	High Similarity	NPC290612
0.8571	High Similarity	NPC79193
0.8557	High Similarity	NPC470591
0.8529	High Similarity	NPC202898
0.8529	High Similarity	NPC92890
0.8529	High Similarity	NPC475319
0.8515	High Similarity	NPC166079
0.8511	High Similarity	NPC77756
0.85	High Similarity	NPC471253
0.8495	Intermediate Similarity	NPC281004
0.8462	Intermediate Similarity	NPC272242
0.8462	Intermediate Similarity	NPC240734
0.8462	Intermediate Similarity	NPC275668
0.8462	Intermediate Similarity	NPC1876
0.8462	Intermediate Similarity	NPC473062
0.8462	Intermediate Similarity	NPC91838
0.8462	Intermediate Similarity	NPC11035
0.8462	Intermediate Similarity	NPC204392
0.8454	Intermediate Similarity	NPC193785
0.8447	Intermediate Similarity	NPC220836
0.8447	Intermediate Similarity	NPC473817
0.8447	Intermediate Similarity	NPC273002
0.8447	Intermediate Similarity	NPC92297
0.8447	Intermediate Similarity	NPC233433
0.8447	Intermediate Similarity	NPC94086
0.8416	Intermediate Similarity	NPC100078
0.8411	Intermediate Similarity	NPC179429
0.8404	Intermediate Similarity	NPC82955
0.8404	Intermediate Similarity	NPC131466
0.8404	Intermediate Similarity	NPC102725
0.8404	Intermediate Similarity	NPC473472
0.84	Intermediate Similarity	NPC213528
0.84	Intermediate Similarity	NPC244969
0.8381	Intermediate Similarity	NPC477492
0.8381	Intermediate Similarity	NPC243572
0.8381	Intermediate Similarity	NPC470543
0.8367	Intermediate Similarity	NPC210157
0.8365	Intermediate Similarity	NPC470622
0.8365	Intermediate Similarity	NPC471431
0.8351	Intermediate Similarity	NPC305808
0.8333	Intermediate Similarity	NPC306776
0.8333	Intermediate Similarity	NPC161035
0.8333	Intermediate Similarity	NPC119628
0.8333	Intermediate Similarity	NPC158051
0.8333	Intermediate Similarity	NPC158367
0.8316	Intermediate Similarity	NPC65550
0.8316	Intermediate Similarity	NPC223143
0.8316	Intermediate Similarity	NPC279329
0.8316	Intermediate Similarity	NPC473542
0.8316	Intermediate Similarity	NPC18536
0.8316	Intermediate Similarity	NPC50443
0.8302	Intermediate Similarity	NPC73986
0.8302	Intermediate Similarity	NPC146563
0.8302	Intermediate Similarity	NPC102619
0.83	Intermediate Similarity	NPC178853
0.83	Intermediate Similarity	NPC475574
0.83	Intermediate Similarity	NPC108227
0.83	Intermediate Similarity	NPC476512
0.83	Intermediate Similarity	NPC476838
0.83	Intermediate Similarity	NPC472081
0.83	Intermediate Similarity	NPC476839
0.8286	Intermediate Similarity	NPC263827
0.8286	Intermediate Similarity	NPC250481
0.8286	Intermediate Similarity	NPC285410
0.8283	Intermediate Similarity	NPC157739
0.828	Intermediate Similarity	NPC472272
0.828	Intermediate Similarity	NPC471410
0.828	Intermediate Similarity	NPC471411
0.8269	Intermediate Similarity	NPC477070
0.8269	Intermediate Similarity	NPC477069
0.8269	Intermediate Similarity	NPC8431
0.8265	Intermediate Similarity	NPC476728
0.8252	Intermediate Similarity	NPC475630
0.8252	Intermediate Similarity	NPC287269
0.8252	Intermediate Similarity	NPC138219
0.8252	Intermediate Similarity	NPC475234
0.8252	Intermediate Similarity	NPC40716
0.8242	Intermediate Similarity	NPC121121
0.8241	Intermediate Similarity	NPC473304
0.8229	Intermediate Similarity	NPC5632
0.8229	Intermediate Similarity	NPC476668
0.8229	Intermediate Similarity	NPC473637
0.8229	Intermediate Similarity	NPC204881
0.8229	Intermediate Similarity	NPC149966
0.8229	Intermediate Similarity	NPC307167
0.8229	Intermediate Similarity	NPC36372
0.8229	Intermediate Similarity	NPC293609
0.8229	Intermediate Similarity	NPC210759
0.8229	Intermediate Similarity	NPC229801
0.8229	Intermediate Similarity	NPC473830
0.8224	Intermediate Similarity	NPC469821
0.8224	Intermediate Similarity	NPC54395
0.8224	Intermediate Similarity	NPC472274
0.8218	Intermediate Similarity	NPC80640
0.8218	Intermediate Similarity	NPC134967
0.8218	Intermediate Similarity	NPC114700
0.8218	Intermediate Similarity	NPC310138
0.8218	Intermediate Similarity	NPC470029
0.8208	Intermediate Similarity	NPC157571
0.8208	Intermediate Similarity	NPC477253
0.82	Intermediate Similarity	NPC470030
0.82	Intermediate Similarity	NPC317019
0.82	Intermediate Similarity	NPC80417
0.8191	Intermediate Similarity	NPC239938
0.8191	Intermediate Similarity	NPC252714
0.819	Intermediate Similarity	NPC129340
0.8182	Intermediate Similarity	NPC471770
0.8182	Intermediate Similarity	NPC74466
0.8182	Intermediate Similarity	NPC470632
0.8182	Intermediate Similarity	NPC472145
0.8182	Intermediate Similarity	NPC278939
0.8182	Intermediate Similarity	NPC473555
0.8173	Intermediate Similarity	NPC473688
0.8173	Intermediate Similarity	NPC207693
0.8173	Intermediate Similarity	NPC471626
0.8173	Intermediate Similarity	NPC195708
0.8173	Intermediate Similarity	NPC262567
0.8173	Intermediate Similarity	NPC224414
0.8173	Intermediate Similarity	NPC231566
0.8163	Intermediate Similarity	NPC287354
0.8163	Intermediate Similarity	NPC62407
0.8152	Intermediate Similarity	NPC474346
0.8152	Intermediate Similarity	NPC475820
0.8152	Intermediate Similarity	NPC213737
0.8152	Intermediate Similarity	NPC474284
0.8152	Intermediate Similarity	NPC474253
0.8148	Intermediate Similarity	NPC469823
0.8148	Intermediate Similarity	NPC469820
0.8148	Intermediate Similarity	NPC88945
0.8148	Intermediate Similarity	NPC137414
0.8144	Intermediate Similarity	NPC476669
0.8144	Intermediate Similarity	NPC311246
0.8144	Intermediate Similarity	NPC137004
0.8144	Intermediate Similarity	NPC172838
0.8144	Intermediate Similarity	NPC277774
0.8144	Intermediate Similarity	NPC88962
0.8144	Intermediate Similarity	NPC473726
0.8144	Intermediate Similarity	NPC149400
0.8144	Intermediate Similarity	NPC167644
0.8144	Intermediate Similarity	NPC144790
0.8144	Intermediate Similarity	NPC476189
0.8137	Intermediate Similarity	NPC97260
0.8137	Intermediate Similarity	NPC139181
0.8137	Intermediate Similarity	NPC476837
0.8131	Intermediate Similarity	NPC97002
0.8119	Intermediate Similarity	NPC478181
0.8113	Intermediate Similarity	NPC274833
0.8113	Intermediate Similarity	NPC477073
0.8111	Intermediate Similarity	NPC80891
0.8111	Intermediate Similarity	NPC201276
0.8108	Intermediate Similarity	NPC470478
0.81	Intermediate Similarity	NPC472144
0.8095	Intermediate Similarity	NPC87393

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 NPC472273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	488
0.1-0.2	3537
0.2-0.3	3390
0.3-0.4	967
0.4-0.5	371
0.5-0.6	236
0.6-0.7	123
0.7-0.8	36
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8788	High Similarity	NPD8170	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6115	Approved
0.8	Intermediate Similarity	NPD6114	Approved
0.8	Intermediate Similarity	NPD6118	Approved
0.8	Intermediate Similarity	NPD6697	Approved
0.7963	Intermediate Similarity	NPD8133	Approved
0.7959	Intermediate Similarity	NPD8171	Discontinued
0.7889	Intermediate Similarity	NPD6116	Phase 1
0.7826	Intermediate Similarity	NPD7507	Approved
0.7818	Intermediate Similarity	NPD6940	Discontinued
0.7778	Intermediate Similarity	NPD6117	Approved
0.7757	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7319	Approved
0.7556	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD3703	Phase 2
0.7447	Intermediate Similarity	NPD6928	Phase 2
0.7407	Intermediate Similarity	NPD6412	Phase 2
0.735	Intermediate Similarity	NPD8328	Phase 3
0.725	Intermediate Similarity	NPD7736	Approved
0.7217	Intermediate Similarity	NPD7328	Approved
0.7217	Intermediate Similarity	NPD7327	Approved
0.7216	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3669	Approved
0.7188	Intermediate Similarity	NPD1780	Approved
0.7188	Intermediate Similarity	NPD1779	Approved
0.7182	Intermediate Similarity	NPD6686	Approved
0.7157	Intermediate Similarity	NPD8034	Phase 2
0.7157	Intermediate Similarity	NPD8035	Phase 2
0.7155	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3702	Approved
0.7094	Intermediate Similarity	NPD8294	Approved
0.7094	Intermediate Similarity	NPD8377	Approved
0.7071	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD8379	Approved
0.7034	Intermediate Similarity	NPD8378	Approved
0.7034	Intermediate Similarity	NPD8033	Approved
0.7034	Intermediate Similarity	NPD8296	Approved
0.7034	Intermediate Similarity	NPD8380	Approved
0.7034	Intermediate Similarity	NPD8335	Approved
0.7027	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD8293	Discontinued
0.6975	Remote Similarity	NPD6370	Approved
0.693	Remote Similarity	NPD6882	Approved
0.6923	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7492	Approved
0.6838	Remote Similarity	NPD6009	Approved
0.6807	Remote Similarity	NPD6059	Approved
0.6807	Remote Similarity	NPD6054	Approved
0.6807	Remote Similarity	NPD6319	Approved
0.6803	Remote Similarity	NPD6616	Approved
0.6789	Remote Similarity	NPD1700	Approved
0.6783	Remote Similarity	NPD8297	Approved
0.6774	Remote Similarity	NPD6081	Approved
0.6774	Remote Similarity	NPD5777	Approved
0.6757	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7503	Approved
0.6748	Remote Similarity	NPD7078	Approved
0.6724	Remote Similarity	NPD4632	Approved
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD4245	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD1811	Approved
0.6632	Remote Similarity	NPD1810	Approved
0.663	Remote Similarity	NPD5360	Phase 3
0.663	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6016	Approved
0.6612	Remote Similarity	NPD6015	Approved
0.6606	Remote Similarity	NPD7638	Approved
0.6593	Remote Similarity	NPD4224	Phase 2
0.6579	Remote Similarity	NPD7320	Approved
0.6579	Remote Similarity	NPD6881	Approved
0.6579	Remote Similarity	NPD6899	Approved
0.6559	Remote Similarity	NPD3698	Phase 2
0.6557	Remote Similarity	NPD5988	Approved
0.6552	Remote Similarity	NPD6649	Approved
0.6552	Remote Similarity	NPD6650	Approved
0.6545	Remote Similarity	NPD7639	Approved
0.6545	Remote Similarity	NPD8418	Phase 2
0.6545	Remote Similarity	NPD7640	Approved
0.6522	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5697	Approved
0.6491	Remote Similarity	NPD5701	Approved
0.6484	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7991	Discontinued
0.6475	Remote Similarity	NPD8513	Phase 3
0.6475	Remote Similarity	NPD6921	Approved
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD8515	Approved
0.6466	Remote Similarity	NPD6883	Approved
0.6466	Remote Similarity	NPD7290	Approved
0.6466	Remote Similarity	NPD7102	Approved
0.6449	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD8084	Approved
0.6429	Remote Similarity	NPD7632	Discontinued
0.6429	Remote Similarity	NPD8083	Approved
0.6429	Remote Similarity	NPD8082	Approved
0.6429	Remote Similarity	NPD8138	Approved
0.6429	Remote Similarity	NPD8085	Approved
0.6429	Remote Similarity	NPD8139	Approved
0.6429	Remote Similarity	NPD8086	Approved
0.641	Remote Similarity	NPD6869	Approved
0.641	Remote Similarity	NPD8130	Phase 1
0.641	Remote Similarity	NPD6617	Approved
0.641	Remote Similarity	NPD6847	Approved
0.6379	Remote Similarity	NPD6014	Approved
0.6379	Remote Similarity	NPD6012	Approved
0.6379	Remote Similarity	NPD6013	Approved
0.6372	Remote Similarity	NPD8276	Approved
0.6372	Remote Similarity	NPD8275	Approved
0.6371	Remote Similarity	NPD7604	Phase 2
0.6371	Remote Similarity	NPD6067	Discontinued
0.6364	Remote Similarity	NPD3671	Phase 1
0.6341	Remote Similarity	NPD5983	Phase 2
0.6325	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5328	Approved
0.6316	Remote Similarity	NPD8081	Approved
0.6316	Remote Similarity	NPD2686	Approved
0.6316	Remote Similarity	NPD2687	Approved
0.6316	Remote Similarity	NPD2254	Approved
0.63	Remote Similarity	NPD7329	Approved
0.6299	Remote Similarity	NPD6033	Approved
0.6293	Remote Similarity	NPD6011	Approved
0.6293	Remote Similarity	NPD8174	Phase 2
0.6281	Remote Similarity	NPD7115	Discovery
0.6271	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6336	Discontinued
0.6261	Remote Similarity	NPD8393	Approved
0.6261	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD4758	Discontinued
0.6239	Remote Similarity	NPD7748	Approved
0.6216	Remote Similarity	NPD7902	Approved
0.6216	Remote Similarity	NPD4755	Approved
0.6207	Remote Similarity	NPD8140	Approved
0.6207	Remote Similarity	NPD8307	Discontinued
0.6204	Remote Similarity	NPD6079	Approved
0.6204	Remote Similarity	NPD7515	Phase 2
0.62	Remote Similarity	NPD4238	Approved
0.62	Remote Similarity	NPD5364	Discontinued
0.62	Remote Similarity	NPD4802	Phase 2
0.6186	Remote Similarity	NPD4634	Approved
0.6106	Remote Similarity	NPD4700	Approved
0.6106	Remote Similarity	NPD5286	Approved
0.6106	Remote Similarity	NPD5285	Approved
0.6106	Remote Similarity	NPD4696	Approved
0.6102	Remote Similarity	NPD8306	Approved
0.6102	Remote Similarity	NPD8305	Approved
0.6071	Remote Similarity	NPD6084	Phase 2
0.6071	Remote Similarity	NPD6083	Phase 2
0.6068	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6274	Approved
0.605	Remote Similarity	NPD8087	Discontinued
0.6048	Remote Similarity	NPD7101	Approved
0.6048	Remote Similarity	NPD7100	Approved
0.6033	Remote Similarity	NPD8298	Phase 2
0.6022	Remote Similarity	NPD7909	Approved
0.6022	Remote Similarity	NPD371	Approved
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD896	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD898	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD897	Approved
0.6	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD4786	Approved
0.5983	Remote Similarity	NPD6920	Discontinued
0.5983	Remote Similarity	NPD4767	Approved
0.5983	Remote Similarity	NPD4768	Approved
0.5982	Remote Similarity	NPD5221	Approved
0.5982	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4697	Phase 3
0.5982	Remote Similarity	NPD5222	Approved
0.5979	Remote Similarity	NPD4787	Phase 1
0.5968	Remote Similarity	NPD6335	Approved
0.5952	Remote Similarity	NPD6908	Approved
0.5952	Remote Similarity	NPD6909	Approved
0.5948	Remote Similarity	NPD5174	Approved
0.5948	Remote Similarity	NPD5175	Approved
0.5946	Remote Similarity	NPD7900	Approved
0.5946	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD6868	Approved
0.5929	Remote Similarity	NPD5173	Approved
0.5926	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7525	Registered
0.5913	Remote Similarity	NPD5223	Approved
0.5909	Remote Similarity	NPD6411	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