NPASS Compound

Structure

NPC475924 OpenBabel07101718182D 29 33 0 0 1 0 0 0 0 0999 V2000 4.2072 -3.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4530 -1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -3.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5870 -1.7872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6092 -1.7872 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.7431 -1.2872 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.5870 -2.7872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7210 -3.2872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8549 -2.7872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3523 -1.1180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9456 -0.2045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4752 -3.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 -1.7872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8549 -1.7872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3190 -1.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4530 -3.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 -4.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9889 -3.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -4.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0522 1.6202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -2.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 -2.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 -1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9889 -1.2872 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 18 1 0 0 0 0 3 4 2 0 0 0 0 3 25 1 0 0 0 0 4 6 1 0 0 0 0 4 13 1 0 0 0 0 5 2 1 1 0 0 0 5 8 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 14 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 6 0 0 0 9 10 1 0 0 0 0 9 20 1 1 0 0 0 10 15 1 0 0 0 0 10 21 1 6 0 0 0 11 12 1 0 0 0 0 11 27 1 1 0 0 0 12 17 1 1 0 0 0 12 27 1 0 0 0 0 13 22 2 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 14 28 1 1 0 0 0 15 26 1 0 0 0 0 15 28 1 1 0 0 0 16 17 1 1 0 0 0 16 23 1 0 0 0 0 16 29 1 0 0 0 0 17 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.11
Volume:	360.016
LogP:	-0.896
LogD:	-0.678
LogS:	-1.619
# Rotatable Bonds:	5
TPSA:	180.2
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.223
Synthetic Accessibility Score:	5.655
Fsp3:	0.824
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.198
MDCK Permeability:	0.00015823330613784492
Pgp-inhibitor:	0.001
Pgp-substrate:	0.274
Human Intestinal Absorption (HIA):	0.879
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	24.26806640625%
Volume Distribution (VD):	0.405
Pgp-substrate:	56.70124435424805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.211
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.436
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	1.25
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.92
Drug-inuced Liver Injury (DILI):	0.825
AMES Toxicity:	0.49
Rat Oral Acute Toxicity:	0.283
Maximum Recommended Daily Dose:	0.108
Skin Sensitization:	0.139
Carcinogencity:	0.331
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC475924

Natural Product ID:	NPC475924
*Common Name:**	Citrifolinin B Epimer A
IUPAC Name:	methyl (1aS,3'R,5S,6R,6aS)-3'-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[1b,5,5a,6a-tetrahydro-1aH-oxireno[3,4]cyclopenta[1,3-d]pyran-6,2'-oxirane]-2-carboxylate
Synonyms:
Standard InCHIKey:	UXNDFLAYYHSFII-KCYIWOEQSA-N
Standard InCHI:	InChI=1S/C17H22O12/c1-24-13(22)4-3-25-14(7-6(4)11-12(27-11)17(7)16(23)29-17)28-15-10(21)9(20)8(19)5(2-18)26-15/h3,5-12,14-16,18-21,23H,2H2,1H3/t5-,6?,7?,8-,9+,10-,11+,12+,14+,15+,16-,17-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C(C3C2[C@@]2(O[C@H]2O)[C@@H]2[C@H]3O2)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518691
PubChem CID:	11015261
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	>	30000.0	nM	PMID[511899]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30000.0	nM	PMID[511899]

☑ 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 NPC475924 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	280
0.1-0.2	1864
0.2-0.3	6206
0.3-0.4	12015
0.4-0.5	11078
0.5-0.6	7534
0.6-0.7	3382
0.7-0.8	311
0.8-0.85	10
0.85-0.9	10
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475851
0.9806	High Similarity	NPC193741
0.9515	High Similarity	NPC197813
0.9515	High Similarity	NPC80338
0.9515	High Similarity	NPC148270
0.9417	High Similarity	NPC170432
0.9231	High Similarity	NPC127235
0.9223	High Similarity	NPC475928
0.9223	High Similarity	NPC37240
0.9126	High Similarity	NPC177013
0.9126	High Similarity	NPC4899
0.9126	High Similarity	NPC35185
0.9126	High Similarity	NPC474730
0.9057	High Similarity	NPC110701
0.8846	High Similarity	NPC287539
0.8846	High Similarity	NPC3488
0.8762	High Similarity	NPC106668
0.8679	High Similarity	NPC27687
0.8462	Intermediate Similarity	NPC161293
0.8462	Intermediate Similarity	NPC284063
0.8381	Intermediate Similarity	NPC86843
0.8365	Intermediate Similarity	NPC6765
0.8365	Intermediate Similarity	NPC93869
0.8333	Intermediate Similarity	NPC329834
0.8288	Intermediate Similarity	NPC139838
0.8288	Intermediate Similarity	NPC59489
0.8269	Intermediate Similarity	NPC274588
0.8241	Intermediate Similarity	NPC304163
0.8241	Intermediate Similarity	NPC80144
0.8224	Intermediate Similarity	NPC186861
0.8224	Intermediate Similarity	NPC471381
0.8148	Intermediate Similarity	NPC67296
0.8148	Intermediate Similarity	NPC476228
0.8148	Intermediate Similarity	NPC216911
0.8131	Intermediate Similarity	NPC49833
0.8131	Intermediate Similarity	NPC45125
0.8131	Intermediate Similarity	NPC249171
0.8131	Intermediate Similarity	NPC37866
0.8113	Intermediate Similarity	NPC170527
0.8095	Intermediate Similarity	NPC63897
0.8077	Intermediate Similarity	NPC66504
0.8056	Intermediate Similarity	NPC476211
0.8056	Intermediate Similarity	NPC476320
0.8037	Intermediate Similarity	NPC236580
0.8037	Intermediate Similarity	NPC471150
0.8037	Intermediate Similarity	NPC304445
0.8018	Intermediate Similarity	NPC54737
0.8	Intermediate Similarity	NPC473148
0.7982	Intermediate Similarity	NPC476230
0.7982	Intermediate Similarity	NPC27474
0.7905	Intermediate Similarity	NPC235051
0.7895	Intermediate Similarity	NPC50223
0.787	Intermediate Similarity	NPC58267
0.787	Intermediate Similarity	NPC263674
0.787	Intermediate Similarity	NPC261372
0.7857	Intermediate Similarity	NPC41681
0.7857	Intermediate Similarity	NPC44004
0.785	Intermediate Similarity	NPC472873
0.7838	Intermediate Similarity	NPC329704
0.7818	Intermediate Similarity	NPC298255
0.7818	Intermediate Similarity	NPC28304
0.781	Intermediate Similarity	NPC231710
0.781	Intermediate Similarity	NPC270908
0.781	Intermediate Similarity	NPC120021
0.781	Intermediate Similarity	NPC216826
0.781	Intermediate Similarity	NPC246173
0.781	Intermediate Similarity	NPC470573
0.781	Intermediate Similarity	NPC65665
0.7778	Intermediate Similarity	NPC474297
0.7748	Intermediate Similarity	NPC13171
0.7748	Intermediate Similarity	NPC195510
0.7748	Intermediate Similarity	NPC261117
0.7748	Intermediate Similarity	NPC310804
0.7739	Intermediate Similarity	NPC41551
0.7736	Intermediate Similarity	NPC70251
0.7736	Intermediate Similarity	NPC473150
0.7736	Intermediate Similarity	NPC475881
0.7736	Intermediate Similarity	NPC274274
0.7736	Intermediate Similarity	NPC294643
0.7727	Intermediate Similarity	NPC306344
0.7727	Intermediate Similarity	NPC22149
0.7727	Intermediate Similarity	NPC255677
0.7714	Intermediate Similarity	NPC22918
0.7714	Intermediate Similarity	NPC50464
0.7712	Intermediate Similarity	NPC277583
0.7706	Intermediate Similarity	NPC472290
0.7692	Intermediate Similarity	NPC31349
0.7686	Intermediate Similarity	NPC473228
0.7686	Intermediate Similarity	NPC470829
0.7685	Intermediate Similarity	NPC476053
0.7685	Intermediate Similarity	NPC167893
0.7642	Intermediate Similarity	NPC117596
0.7619	Intermediate Similarity	NPC213634
0.7619	Intermediate Similarity	NPC148534
0.7611	Intermediate Similarity	NPC86095
0.7596	Intermediate Similarity	NPC470657
0.7593	Intermediate Similarity	NPC71589
0.7589	Intermediate Similarity	NPC222062
0.7589	Intermediate Similarity	NPC250545
0.7583	Intermediate Similarity	NPC13710
0.7583	Intermediate Similarity	NPC475401
0.7576	Intermediate Similarity	NPC48414
0.7576	Intermediate Similarity	NPC5153
0.757	Intermediate Similarity	NPC472126
0.757	Intermediate Similarity	NPC472124
0.757	Intermediate Similarity	NPC472125
0.757	Intermediate Similarity	NPC155215
0.7568	Intermediate Similarity	NPC473146
0.7563	Intermediate Similarity	NPC170692
0.7563	Intermediate Similarity	NPC255450
0.7547	Intermediate Similarity	NPC93190
0.7524	Intermediate Similarity	NPC258501
0.7522	Intermediate Similarity	NPC118761
0.7522	Intermediate Similarity	NPC234304
0.7522	Intermediate Similarity	NPC284929
0.7522	Intermediate Similarity	NPC197541
0.7522	Intermediate Similarity	NPC267869
0.7521	Intermediate Similarity	NPC477092
0.7519	Intermediate Similarity	NPC158350
0.75	Intermediate Similarity	NPC212486
0.75	Intermediate Similarity	NPC475305
0.75	Intermediate Similarity	NPC61201
0.75	Intermediate Similarity	NPC258216
0.75	Intermediate Similarity	NPC208307
0.7479	Intermediate Similarity	NPC305044
0.7479	Intermediate Similarity	NPC265290
0.7477	Intermediate Similarity	NPC216284
0.7477	Intermediate Similarity	NPC472015
0.7477	Intermediate Similarity	NPC474213
0.7477	Intermediate Similarity	NPC307699
0.7463	Intermediate Similarity	NPC471172
0.7455	Intermediate Similarity	NPC241911
0.7434	Intermediate Similarity	NPC471599
0.7422	Intermediate Similarity	NPC155529
0.7411	Intermediate Similarity	NPC244878
0.7407	Intermediate Similarity	NPC470379
0.7407	Intermediate Similarity	NPC470373
0.7407	Intermediate Similarity	NPC194854
0.7407	Intermediate Similarity	NPC48813
0.7407	Intermediate Similarity	NPC276298
0.7395	Intermediate Similarity	NPC287075
0.7395	Intermediate Similarity	NPC101965
0.7395	Intermediate Similarity	NPC101400
0.7391	Intermediate Similarity	NPC243998
0.7391	Intermediate Similarity	NPC223450
0.7387	Intermediate Similarity	NPC181151
0.7383	Intermediate Similarity	NPC472872
0.7383	Intermediate Similarity	NPC92974
0.7383	Intermediate Similarity	NPC215556
0.7373	Intermediate Similarity	NPC474750
0.7368	Intermediate Similarity	NPC474783
0.7368	Intermediate Similarity	NPC260809
0.7368	Intermediate Similarity	NPC123505
0.7364	Intermediate Similarity	NPC14961
0.7364	Intermediate Similarity	NPC101051
0.7364	Intermediate Similarity	NPC163228
0.7364	Intermediate Similarity	NPC270013
0.7358	Intermediate Similarity	NPC186148
0.7353	Intermediate Similarity	NPC16729
0.7353	Intermediate Similarity	NPC475462
0.735	Intermediate Similarity	NPC77089
0.7348	Intermediate Similarity	NPC75616
0.7345	Intermediate Similarity	NPC471767
0.7345	Intermediate Similarity	NPC473332
0.7345	Intermediate Similarity	NPC20673
0.7345	Intermediate Similarity	NPC219038
0.7344	Intermediate Similarity	NPC173347
0.7333	Intermediate Similarity	NPC47958
0.7333	Intermediate Similarity	NPC304509
0.7333	Intermediate Similarity	NPC121816
0.7333	Intermediate Similarity	NPC149725
0.7328	Intermediate Similarity	NPC254538
0.7328	Intermediate Similarity	NPC474285
0.7321	Intermediate Similarity	NPC473307
0.7321	Intermediate Similarity	NPC151093
0.7317	Intermediate Similarity	NPC142882
0.7315	Intermediate Similarity	NPC206614
0.7315	Intermediate Similarity	NPC474323
0.7311	Intermediate Similarity	NPC98038
0.7311	Intermediate Similarity	NPC313921
0.7308	Intermediate Similarity	NPC471234
0.7304	Intermediate Similarity	NPC169843
0.7297	Intermediate Similarity	NPC476009
0.7297	Intermediate Similarity	NPC476315
0.7297	Intermediate Similarity	NPC306041
0.729	Intermediate Similarity	NPC58219
0.729	Intermediate Similarity	NPC177629
0.729	Intermediate Similarity	NPC79549
0.7287	Intermediate Similarity	NPC42206
0.7287	Intermediate Similarity	NPC471855
0.7281	Intermediate Similarity	NPC250594
0.7281	Intermediate Similarity	NPC475956
0.7281	Intermediate Similarity	NPC200672
0.7281	Intermediate Similarity	NPC252242
0.7281	Intermediate Similarity	NPC214714
0.728	Intermediate Similarity	NPC27363
0.7273	Intermediate Similarity	NPC190294
0.7273	Intermediate Similarity	NPC88945
0.7273	Intermediate Similarity	NPC474035
0.7273	Intermediate Similarity	NPC81386

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 NPC475924 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	2414
0.2-0.3	3849
0.3-0.4	1771
0.4-0.5	503
0.5-0.6	270
0.6-0.7	65
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7167	Intermediate Similarity	NPD6053	Discontinued
0.7165	Intermediate Similarity	NPD7507	Approved
0.7119	Intermediate Similarity	NPD6686	Approved
0.7107	Intermediate Similarity	NPD8133	Approved
0.7	Intermediate Similarity	NPD7319	Approved
0.7	Intermediate Similarity	NPD6698	Approved
0.7	Intermediate Similarity	NPD46	Approved
0.6984	Remote Similarity	NPD7503	Approved
0.685	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6412	Phase 2
0.675	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6371	Approved
0.6719	Remote Similarity	NPD8517	Approved
0.6719	Remote Similarity	NPD8033	Approved
0.6719	Remote Similarity	NPD8516	Approved
0.6719	Remote Similarity	NPD8515	Approved
0.6614	Remote Similarity	NPD7328	Approved
0.6614	Remote Similarity	NPD7327	Approved
0.6607	Remote Similarity	NPD1695	Approved
0.6583	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7516	Approved
0.6545	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7736	Approved
0.6538	Remote Similarity	NPD6370	Approved
0.6512	Remote Similarity	NPD6319	Approved
0.6512	Remote Similarity	NPD8377	Approved
0.6512	Remote Similarity	NPD8294	Approved
0.6489	Remote Similarity	NPD7642	Approved
0.6489	Remote Similarity	NPD7829	Approved
0.6489	Remote Similarity	NPD7830	Approved
0.6466	Remote Similarity	NPD8293	Discontinued
0.6462	Remote Similarity	NPD8380	Approved
0.6462	Remote Similarity	NPD8296	Approved
0.6462	Remote Similarity	NPD8335	Approved
0.6462	Remote Similarity	NPD8378	Approved
0.6462	Remote Similarity	NPD8379	Approved
0.6439	Remote Similarity	NPD7492	Approved
0.6406	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6009	Approved
0.6406	Remote Similarity	NPD7115	Discovery
0.6404	Remote Similarity	NPD7838	Discovery
0.6391	Remote Similarity	NPD6616	Approved
0.6385	Remote Similarity	NPD6054	Approved
0.6371	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6882	Approved
0.6343	Remote Similarity	NPD7078	Approved
0.6339	Remote Similarity	NPD4249	Approved
0.6336	Remote Similarity	NPD6015	Approved
0.6336	Remote Similarity	NPD6016	Approved
0.6333	Remote Similarity	NPD5344	Discontinued
0.632	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD4632	Approved
0.6288	Remote Similarity	NPD8080	Discontinued
0.6288	Remote Similarity	NPD5988	Approved
0.6283	Remote Similarity	NPD4251	Approved
0.6283	Remote Similarity	NPD4250	Approved
0.6273	Remote Similarity	NPD6435	Approved
0.6269	Remote Similarity	NPD8451	Approved
0.626	Remote Similarity	NPD6059	Approved
0.626	Remote Similarity	NPD6008	Approved
0.6231	Remote Similarity	NPD7641	Discontinued
0.6222	Remote Similarity	NPD8448	Approved
0.6222	Remote Similarity	NPD8074	Phase 3
0.622	Remote Similarity	NPD8297	Approved
0.6212	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7983	Approved
0.6179	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.616	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6650	Approved
0.6142	Remote Similarity	NPD6649	Approved
0.6119	Remote Similarity	NPD8328	Phase 3
0.6111	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6372	Approved
0.6111	Remote Similarity	NPD6373	Approved
0.6091	Remote Similarity	NPD5368	Approved
0.6087	Remote Similarity	NPD8391	Approved
0.6087	Remote Similarity	NPD8392	Approved
0.6087	Remote Similarity	NPD8390	Approved
0.608	Remote Similarity	NPD5697	Approved
0.608	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD8340	Approved
0.6074	Remote Similarity	NPD8299	Approved
0.6074	Remote Similarity	NPD8341	Approved
0.6074	Remote Similarity	NPD8342	Approved
0.6071	Remote Similarity	NPD7154	Phase 3
0.6056	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.605	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6881	Approved
0.6032	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD7685	Pre-registration
0.5984	Remote Similarity	NPD6014	Approved
0.5984	Remote Similarity	NPD6012	Approved
0.5984	Remote Similarity	NPD6648	Approved
0.5984	Remote Similarity	NPD6013	Approved
0.5983	Remote Similarity	NPD5785	Approved
0.597	Remote Similarity	NPD8266	Approved
0.597	Remote Similarity	NPD8269	Approved
0.597	Remote Similarity	NPD8444	Approved
0.597	Remote Similarity	NPD5983	Phase 2
0.597	Remote Similarity	NPD8267	Approved
0.597	Remote Similarity	NPD8268	Approved
0.5966	Remote Similarity	NPD5282	Discontinued
0.5965	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5701	Approved
0.5946	Remote Similarity	NPD4822	Approved
0.5946	Remote Similarity	NPD4821	Approved
0.5946	Remote Similarity	NPD4820	Approved
0.5946	Remote Similarity	NPD4819	Approved
0.5946	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7290	Approved
0.5938	Remote Similarity	NPD7102	Approved
0.5938	Remote Similarity	NPD4634	Approved
0.5938	Remote Similarity	NPD6883	Approved
0.5929	Remote Similarity	NPD7260	Phase 2
0.5929	Remote Similarity	NPD5362	Discontinued
0.5913	Remote Similarity	NPD5786	Approved
0.5906	Remote Similarity	NPD6011	Approved
0.5906	Remote Similarity	NPD7320	Approved
0.5902	Remote Similarity	NPD4225	Approved
0.5902	Remote Similarity	NPD7638	Approved
0.5893	Remote Similarity	NPD5369	Approved
0.5891	Remote Similarity	NPD6847	Approved
0.5891	Remote Similarity	NPD8130	Phase 1
0.5891	Remote Similarity	NPD6869	Approved
0.5891	Remote Similarity	NPD6617	Approved
0.5887	Remote Similarity	NPD8086	Approved
0.5887	Remote Similarity	NPD8082	Approved
0.5887	Remote Similarity	NPD8139	Approved
0.5887	Remote Similarity	NPD8085	Approved
0.5887	Remote Similarity	NPD8083	Approved
0.5887	Remote Similarity	NPD8138	Approved
0.5887	Remote Similarity	NPD8084	Approved
0.5882	Remote Similarity	NPD5779	Approved
0.5882	Remote Similarity	NPD5778	Approved
0.5868	Remote Similarity	NPD7839	Suspended
0.5854	Remote Similarity	NPD7640	Approved
0.5854	Remote Similarity	NPD7639	Approved
0.584	Remote Similarity	NPD8276	Approved
0.584	Remote Similarity	NPD8275	Approved
0.5827	Remote Similarity	NPD8337	Approved
0.5827	Remote Similarity	NPD6033	Approved
0.5827	Remote Similarity	NPD8336	Approved
0.5826	Remote Similarity	NPD5363	Approved
0.582	Remote Similarity	NPD6083	Phase 2
0.582	Remote Similarity	NPD6084	Phase 2
0.5806	Remote Similarity	NPD1700	Approved
0.5797	Remote Similarity	NPD6336	Discontinued
0.5794	Remote Similarity	NPD8081	Approved
0.5789	Remote Similarity	NPD4788	Approved
0.5785	Remote Similarity	NPD5695	Phase 3
0.5775	Remote Similarity	NPD6845	Suspended
0.5772	Remote Similarity	NPD5696	Approved
0.5766	Remote Similarity	NPD4271	Approved
0.5766	Remote Similarity	NPD4802	Phase 2
0.5766	Remote Similarity	NPD6067	Discontinued
0.5766	Remote Similarity	NPD4238	Approved
0.5766	Remote Similarity	NPD4268	Approved
0.5763	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD6101	Approved
0.576	Remote Similarity	NPD5211	Phase 2
0.575	Remote Similarity	NPD6399	Phase 3
0.5748	Remote Similarity	NPD8393	Approved
0.5745	Remote Similarity	NPD5956	Approved
0.5735	Remote Similarity	NPD6921	Approved
0.5726	Remote Similarity	NPD5285	Approved
0.5726	Remote Similarity	NPD5286	Approved
0.5726	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD6274	Approved
0.5702	Remote Similarity	NPD4269	Approved
0.5702	Remote Similarity	NPD4270	Approved
0.5691	Remote Similarity	NPD4755	Approved
0.5669	Remote Similarity	NPD5141	Approved
0.5667	Remote Similarity	NPD6411	Approved
0.5667	Remote Similarity	NPD8035	Phase 2
0.5667	Remote Similarity	NPD8034	Phase 2
0.5664	Remote Similarity	NPD8338	Approved
0.5652	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD3669	Approved
0.5649	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD5226	Approved
0.5635	Remote Similarity	NPD5224	Approved
0.5635	Remote Similarity	NPD5225	Approved
0.5635	Remote Similarity	NPD4633	Approved
0.5614	Remote Similarity	NPD1779	Approved
0.5614	Remote Similarity	NPD1780	Approved
0.5603	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.56	Remote Similarity	NPD4700	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