NPASS Compound

Structure

NPC260266 OpenBabel07101718312D 35 39 0 0 1 0 0 0 0 0999 V2000 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 2 2 0 0 0 0 1 8 1 0 0 0 0 2 11 1 0 0 0 0 3 8 2 0 0 0 0 3 12 1 0 0 0 0 4 9 2 0 0 0 0 4 13 1 0 0 0 0 5 9 1 0 0 0 0 5 16 2 0 0 0 0 6 14 2 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 34 1 0 0 0 0 9 25 1 0 0 0 0 10 17 1 0 0 0 0 10 20 1 0 0 0 0 11 12 2 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 18 2 0 0 0 0 13 28 1 0 0 0 0 14 17 1 0 0 0 0 14 29 1 0 0 0 0 15 19 2 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 16 34 1 0 0 0 0 17 24 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 19 24 1 0 0 0 0 20 31 2 0 0 0 0 21 22 1 0 0 0 0 21 32 2 0 0 0 0 22 23 1 0 0 0 0 22 33 1 6 0 0 0 23 8 1 1 0 0 0 23 35 1 0 0 0 0 24 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.07
Volume:	445.933
LogP:	1.658
LogD:	0.562
LogS:	-4.206
# Rotatable Bonds:	2
TPSA:	198.12
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	4.06
Fsp3:	0.083
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.285
MDCK Permeability:	3.985930106864544e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.881
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	92.56260681152344%
Volume Distribution (VD):	0.441
Pgp-substrate:	4.704848766326904%

ADMET: Metabolism

CYP1A2-inhibitor:	0.202
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.688
CYP2C9-substrate:	0.65
CYP2D6-inhibitor:	0.126
CYP2D6-substrate:	0.194
CYP3A4-inhibitor:	0.148
CYP3A4-substrate:	0.1

ADMET: Excretion

Clearance (CL):	3.305
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.155
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.334
Rat Oral Acute Toxicity:	0.459
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.926
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.908
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC260266

Natural Product ID:	NPC260266
*Common Name:**	ITLIIDFSTPOGDA-XZOQPEGZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ITLIIDFSTPOGDA-XZOQPEGZSA-N
Standard InCHI:	InChI=1S/C24H16O11/c25-9-4-13(28)18-16(5-9)34-7-10(20(18)31)17-14(29)6-15(30)19-21(32)22(33)23(35-24(17)19)8-1-2-11(26)12(27)3-8/h1-7,22-23,25-30,33H/t22-,23+/m0/s1
SMILES:	c1cc(c(cc1[C@@H]1[C@H](C(=O)c2c(cc(c(c3coc4cc(cc(c4c3=O)O)O)c2O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3422284
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0003530] Pyranoisoflavonoids

*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
NPO5259	Garcinia buchananii	Species	Clusiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[25625705]
NPO5259	Garcinia buchananii	Species	Clusiaceae	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
EC50	1
Others	4

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.	EC50	=	17500.0	nM	PMID[532914]
NPT35	Others	n.a.	Activity	=	2.92	mmolequiv/mmol	PMID[532914]
NPT35	Others	n.a.	Activity	=	1.48	mmolequiv/mmol	PMID[532914]
NPT35	Others	n.a.	Activity	=	6.96	mmolequiv/mmol	PMID[532914]
NPT35	Others	n.a.	Activity	=	4.38	mmolequiv/mmol	PMID[532914]

☑ 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 NPC260266 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	526
0.1-0.2	1987
0.2-0.3	4844
0.3-0.4	10608
0.4-0.5	7096
0.5-0.6	3901
0.6-0.7	5314
0.7-0.8	4677
0.8-0.85	2058
0.85-0.9	1474
0.9-0.95	209
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9682	High Similarity	NPC289771
0.9568	High Similarity	NPC257667
0.9568	High Similarity	NPC186847
0.9568	High Similarity	NPC472454
0.9565	High Similarity	NPC107627
0.9557	High Similarity	NPC142252
0.9554	High Similarity	NPC117418
0.9554	High Similarity	NPC53545
0.9503	High Similarity	NPC295082
0.9503	High Similarity	NPC243877
0.95	High Similarity	NPC72787
0.95	High Similarity	NPC7688
0.95	High Similarity	NPC7154
0.95	High Similarity	NPC36916
0.95	High Similarity	NPC36
0.95	High Similarity	NPC125039
0.95	High Similarity	NPC58223
0.9497	High Similarity	NPC476247
0.9448	High Similarity	NPC271848
0.9448	High Similarity	NPC262580
0.9448	High Similarity	NPC212038
0.9448	High Similarity	NPC289396
0.9448	High Similarity	NPC81332
0.9444	High Similarity	NPC475212
0.9441	High Similarity	NPC171985
0.9441	High Similarity	NPC320741
0.9437	High Similarity	NPC472625
0.9434	High Similarity	NPC113163
0.9434	High Similarity	NPC66618
0.9434	High Similarity	NPC84324
0.9434	High Similarity	NPC305987
0.9434	High Similarity	NPC288131
0.9434	High Similarity	NPC471499
0.9434	High Similarity	NPC26326
0.9434	High Similarity	NPC165970
0.943	High Similarity	NPC22192
0.9387	High Similarity	NPC102277
0.9387	High Similarity	NPC279209
0.9383	High Similarity	NPC14662
0.9379	High Similarity	NPC471788
0.9375	High Similarity	NPC219927
0.9371	High Similarity	NPC470326
0.9371	High Similarity	NPC282009
0.9371	High Similarity	NPC287328
0.9371	High Similarity	NPC101731
0.9321	High Similarity	NPC471213
0.9321	High Similarity	NPC207575
0.9321	High Similarity	NPC224851
0.9321	High Similarity	NPC13481
0.9313	High Similarity	NPC474038
0.9313	High Similarity	NPC228383
0.9313	High Similarity	NPC158188
0.9308	High Similarity	NPC284127
0.9308	High Similarity	NPC123544
0.9308	High Similarity	NPC172202
0.9308	High Similarity	NPC476410
0.9304	High Similarity	NPC78492
0.9304	High Similarity	NPC208152
0.9299	High Similarity	NPC27532
0.9299	High Similarity	NPC244250
0.9299	High Similarity	NPC20907
0.9299	High Similarity	NPC268193
0.9299	High Similarity	NPC246328
0.9299	High Similarity	NPC325028
0.9299	High Similarity	NPC256346
0.9277	High Similarity	NPC144097
0.9277	High Similarity	NPC61904
0.9259	High Similarity	NPC470457
0.9259	High Similarity	NPC62261
0.9255	High Similarity	NPC220912
0.9255	High Similarity	NPC474034
0.9255	High Similarity	NPC474033
0.9255	High Similarity	NPC477841
0.925	High Similarity	NPC118256
0.925	High Similarity	NPC475784
0.925	High Similarity	NPC119209
0.925	High Similarity	NPC192686
0.9245	High Similarity	NPC474055
0.9245	High Similarity	NPC183851
0.9245	High Similarity	NPC472598
0.9245	High Similarity	NPC63454
0.9245	High Similarity	NPC291508
0.9245	High Similarity	NPC52530
0.9241	High Similarity	NPC304745
0.9241	High Similarity	NPC321779
0.9241	High Similarity	NPC111341
0.9236	High Similarity	NPC240476
0.9236	High Similarity	NPC9743
0.9236	High Similarity	NPC246162
0.9236	High Similarity	NPC19721
0.9236	High Similarity	NPC36835
0.9236	High Similarity	NPC61506
0.9236	High Similarity	NPC260491
0.9222	High Similarity	NPC35167
0.9222	High Similarity	NPC253521
0.9222	High Similarity	NPC37668
0.9222	High Similarity	NPC113836
0.9217	High Similarity	NPC294629
0.9217	High Similarity	NPC223426
0.9217	High Similarity	NPC34267
0.9217	High Similarity	NPC214621
0.9217	High Similarity	NPC81042
0.9207	High Similarity	NPC177480
0.9198	High Similarity	NPC124038
0.9198	High Similarity	NPC63438
0.9198	High Similarity	NPC470459
0.9193	High Similarity	NPC308992
0.9193	High Similarity	NPC134783
0.9193	High Similarity	NPC472632
0.9193	High Similarity	NPC472634
0.9187	High Similarity	NPC204879
0.9182	High Similarity	NPC278778
0.9182	High Similarity	NPC474638
0.9182	High Similarity	NPC320825
0.9182	High Similarity	NPC13858
0.9182	High Similarity	NPC326037
0.9182	High Similarity	NPC201837
0.9182	High Similarity	NPC291878
0.9182	High Similarity	NPC195796
0.9182	High Similarity	NPC471500
0.9182	High Similarity	NPC35038
0.9182	High Similarity	NPC250922
0.9177	High Similarity	NPC213896
0.9177	High Similarity	NPC109594
0.9177	High Similarity	NPC326592
0.9177	High Similarity	NPC192083
0.9177	High Similarity	NPC112701
0.9177	High Similarity	NPC141212
0.9172	High Similarity	NPC289774
0.9172	High Similarity	NPC477897
0.9172	High Similarity	NPC209846
0.9172	High Similarity	NPC227485
0.9172	High Similarity	NPC328740
0.9167	High Similarity	NPC324742
0.9152	High Similarity	NPC74559
0.9152	High Similarity	NPC150767
0.9152	High Similarity	NPC78734
0.9152	High Similarity	NPC218488
0.9146	High Similarity	NPC8965
0.9146	High Similarity	NPC470456
0.9146	High Similarity	NPC158761
0.9141	High Similarity	NPC50960
0.9141	High Similarity	NPC277205
0.9141	High Similarity	NPC477840
0.9136	High Similarity	NPC211107
0.9136	High Similarity	NPC472635
0.9136	High Similarity	NPC474150
0.9136	High Similarity	NPC83922
0.9136	High Similarity	NPC474162
0.9136	High Similarity	NPC472448
0.913	High Similarity	NPC472631
0.913	High Similarity	NPC472630
0.913	High Similarity	NPC24164
0.913	High Similarity	NPC263449
0.913	High Similarity	NPC470183
0.913	High Similarity	NPC174953
0.913	High Similarity	NPC328102
0.9125	High Similarity	NPC218313
0.9125	High Similarity	NPC471479
0.9125	High Similarity	NPC68324
0.9125	High Similarity	NPC474681
0.9125	High Similarity	NPC156818
0.9125	High Similarity	NPC473272
0.9125	High Similarity	NPC67876
0.9125	High Similarity	NPC471209
0.9125	High Similarity	NPC38779
0.9125	High Similarity	NPC284820
0.9125	High Similarity	NPC52889
0.9125	High Similarity	NPC160512
0.9125	High Similarity	NPC114179
0.9125	High Similarity	NPC471515
0.9125	High Similarity	NPC289322
0.9125	High Similarity	NPC27337
0.9119	High Similarity	NPC152951
0.9119	High Similarity	NPC48579
0.9119	High Similarity	NPC57674
0.9119	High Similarity	NPC470327
0.9119	High Similarity	NPC477503
0.9119	High Similarity	NPC259710
0.9119	High Similarity	NPC217706
0.9119	High Similarity	NPC133392
0.9119	High Similarity	NPC168247
0.9119	High Similarity	NPC117992
0.9119	High Similarity	NPC207809
0.9119	High Similarity	NPC304207
0.9119	High Similarity	NPC45849
0.9119	High Similarity	NPC200761
0.9119	High Similarity	NPC230149
0.9114	High Similarity	NPC10807
0.9114	High Similarity	NPC56232
0.9114	High Similarity	NPC150123
0.9114	High Similarity	NPC157784
0.9114	High Similarity	NPC323626
0.9114	High Similarity	NPC324233
0.9114	High Similarity	NPC37684
0.9114	High Similarity	NPC35567
0.9114	High Similarity	NPC243171
0.9114	High Similarity	NPC171651
0.9114	High Similarity	NPC244583
0.9114	High Similarity	NPC63187

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 NPC260266 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	475
0.1-0.2	980
0.2-0.3	2016
0.3-0.4	2621
0.4-0.5	1685
0.5-0.6	915
0.6-0.7	298
0.7-0.8	107
0.8-0.85	27
0.85-0.9	22
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.95	High Similarity	NPD6167	Clinical (unspecified phase)
0.95	High Similarity	NPD6166	Phase 2
0.95	High Similarity	NPD6168	Clinical (unspecified phase)
0.9177	High Similarity	NPD2393	Clinical (unspecified phase)
0.9108	High Similarity	NPD4380	Phase 2
0.9062	High Similarity	NPD4868	Clinical (unspecified phase)
0.8994	High Similarity	NPD1934	Approved
0.8982	High Similarity	NPD7993	Clinical (unspecified phase)
0.8982	High Similarity	NPD6797	Phase 2
0.8929	High Similarity	NPD7251	Discontinued
0.8916	High Similarity	NPD3818	Discontinued
0.8876	High Similarity	NPD4338	Clinical (unspecified phase)
0.8862	High Similarity	NPD7054	Approved
0.8854	High Similarity	NPD1512	Approved
0.8827	High Similarity	NPD3882	Suspended
0.882	High Similarity	NPD2801	Approved
0.881	High Similarity	NPD7472	Approved
0.881	High Similarity	NPD7074	Phase 3
0.8773	High Similarity	NPD7075	Discontinued
0.8773	High Similarity	NPD4381	Clinical (unspecified phase)
0.8765	High Similarity	NPD7808	Phase 3
0.875	High Similarity	NPD7804	Clinical (unspecified phase)
0.8726	High Similarity	NPD1511	Approved
0.8671	High Similarity	NPD4378	Clinical (unspecified phase)
0.865	High Similarity	NPD3817	Phase 2
0.8642	High Similarity	NPD6801	Discontinued
0.8589	High Similarity	NPD7096	Clinical (unspecified phase)
0.8554	High Similarity	NPD5494	Approved
0.8553	High Similarity	NPD7410	Clinical (unspecified phase)
0.8537	High Similarity	NPD8443	Clinical (unspecified phase)
0.8537	High Similarity	NPD5402	Approved
0.8503	High Similarity	NPD6959	Discontinued
0.8466	Intermediate Similarity	NPD7411	Suspended
0.8421	Intermediate Similarity	NPD5844	Phase 1
0.8408	Intermediate Similarity	NPD1549	Phase 2
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD5403	Approved
0.8304	Intermediate Similarity	NPD7473	Discontinued
0.8276	Intermediate Similarity	NPD6559	Discontinued
0.8253	Intermediate Similarity	NPD7819	Suspended
0.8246	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1510	Phase 2
0.821	Intermediate Similarity	NPD5401	Approved
0.8165	Intermediate Similarity	NPD2796	Approved
0.8148	Intermediate Similarity	NPD6799	Approved
0.8144	Intermediate Similarity	NPD1465	Phase 2
0.807	Intermediate Similarity	NPD1247	Approved
0.8066	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD3751	Discontinued
0.7978	Intermediate Similarity	NPD8313	Approved
0.7978	Intermediate Similarity	NPD8312	Approved
0.7977	Intermediate Similarity	NPD3926	Phase 2
0.7964	Intermediate Similarity	NPD6599	Discontinued
0.7962	Intermediate Similarity	NPD1613	Approved
0.7962	Intermediate Similarity	NPD943	Approved
0.7962	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD919	Approved
0.7941	Intermediate Similarity	NPD7768	Phase 2
0.7919	Intermediate Similarity	NPD3787	Discontinued
0.7914	Intermediate Similarity	NPD6190	Approved
0.7895	Intermediate Similarity	NPD3749	Approved
0.7892	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1240	Approved
0.7791	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6777	Approved
0.7766	Intermediate Similarity	NPD6781	Approved
0.7766	Intermediate Similarity	NPD6779	Approved
0.7766	Intermediate Similarity	NPD6776	Approved
0.7766	Intermediate Similarity	NPD6782	Approved
0.7766	Intermediate Similarity	NPD6780	Approved
0.7766	Intermediate Similarity	NPD6778	Approved
0.775	Intermediate Similarity	NPD1607	Approved
0.7747	Intermediate Similarity	NPD8150	Discontinued
0.7744	Intermediate Similarity	NPD3750	Approved
0.7707	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7435	Discontinued
0.7643	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7228	Approved
0.7633	Intermediate Similarity	NPD1653	Approved
0.7629	Intermediate Similarity	NPD8151	Discontinued
0.7607	Intermediate Similarity	NPD2935	Discontinued
0.7605	Intermediate Similarity	NPD7390	Discontinued
0.7604	Intermediate Similarity	NPD7870	Phase 2
0.7604	Intermediate Similarity	NPD7871	Phase 2
0.7588	Intermediate Similarity	NPD3226	Approved
0.7579	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD230	Phase 1
0.7576	Intermediate Similarity	NPD2800	Approved
0.7574	Intermediate Similarity	NPD920	Approved
0.7571	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2532	Approved
0.756	Intermediate Similarity	NPD2533	Approved
0.756	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2534	Approved
0.7557	Intermediate Similarity	NPD7199	Phase 2
0.7552	Intermediate Similarity	NPD7697	Approved
0.7552	Intermediate Similarity	NPD7696	Phase 3
0.7552	Intermediate Similarity	NPD7698	Approved
0.7547	Intermediate Similarity	NPD3027	Phase 3
0.7543	Intermediate Similarity	NPD6234	Discontinued
0.753	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8455	Phase 2
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD6535	Approved
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7485	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7685	Pre-registration
0.7459	Intermediate Similarity	NPD8434	Phase 2
0.7457	Intermediate Similarity	NPD37	Approved
0.7456	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3748	Approved
0.7436	Intermediate Similarity	NPD7584	Approved
0.7432	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4965	Approved
0.7429	Intermediate Similarity	NPD4967	Phase 2
0.7429	Intermediate Similarity	NPD4966	Approved
0.7425	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7874	Approved
0.7411	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4360	Phase 2
0.7407	Intermediate Similarity	NPD4363	Phase 3
0.7403	Intermediate Similarity	NPD7286	Phase 2
0.7382	Intermediate Similarity	NPD7699	Phase 2
0.7382	Intermediate Similarity	NPD7700	Phase 2
0.7375	Intermediate Similarity	NPD4908	Phase 1
0.7374	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7801	Approved
0.7374	Intermediate Similarity	NPD7783	Phase 2
0.7365	Intermediate Similarity	NPD1243	Approved
0.7362	Intermediate Similarity	NPD447	Suspended
0.7349	Intermediate Similarity	NPD2346	Discontinued
0.7349	Intermediate Similarity	NPD2344	Approved
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.732	Intermediate Similarity	NPD6823	Phase 2
0.7317	Intermediate Similarity	NPD6651	Approved
0.7294	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6798	Discontinued
0.7261	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6844	Discontinued
0.7245	Intermediate Similarity	NPD8320	Phase 1
0.7245	Intermediate Similarity	NPD8319	Approved
0.7205	Intermediate Similarity	NPD9494	Approved
0.7189	Intermediate Similarity	NPD7240	Approved
0.7186	Intermediate Similarity	NPD6099	Approved
0.7186	Intermediate Similarity	NPD6100	Approved
0.7184	Intermediate Similarity	NPD7458	Discontinued
0.7176	Intermediate Similarity	NPD2309	Approved
0.7152	Intermediate Similarity	NPD1933	Approved
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7136	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7127	Intermediate Similarity	NPD5711	Approved
0.7127	Intermediate Similarity	NPD5710	Approved
0.7127	Intermediate Similarity	NPD7229	Phase 3
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.7118	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2424	Discontinued
0.7083	Intermediate Similarity	NPD5405	Approved
0.7083	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5406	Approved
0.7083	Intermediate Similarity	NPD6213	Phase 3
0.7083	Intermediate Similarity	NPD5404	Approved
0.7083	Intermediate Similarity	NPD5408	Approved
0.7083	Intermediate Similarity	NPD6212	Phase 3
0.7081	Intermediate Similarity	NPD1203	Approved
0.7072	Intermediate Similarity	NPD8127	Discontinued
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7549	Discontinued
0.7055	Intermediate Similarity	NPD6832	Phase 2
0.705	Intermediate Similarity	NPD7585	Approved
0.7044	Intermediate Similarity	NPD1610	Phase 2
0.7039	Intermediate Similarity	NPD4111	Phase 1
0.7039	Intermediate Similarity	NPD4665	Approved
0.7016	Intermediate Similarity	NPD4287	Approved
0.701	Intermediate Similarity	NPD4361	Phase 2
0.701	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1548	Phase 1
0.7005	Intermediate Similarity	NPD2494	Approved
0.7005	Intermediate Similarity	NPD2493	Approved
0.7005	Intermediate Similarity	NPD3452	Approved
0.7005	Intermediate Similarity	NPD3450	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