NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1072.27
Volume:	1000.521
LogP:	2.117
LogD:	1.031
LogS:	-4.925
# Rotatable Bonds:	28
TPSA:	347.2
# H-Bond Aceptor:	27
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	27

MedChem Properties

QED Drug-Likeness Score:	0.106
Synthetic Accessibility Score:	5.763
Fsp3:	0.469
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.122
MDCK Permeability:	0.0003107957309111953
Pgp-inhibitor:	0.997
Pgp-substrate:	0.907
Human Intestinal Absorption (HIA):	0.994
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	42.493797302246094%
Volume Distribution (VD):	0.503
Pgp-substrate:	17.483753204345703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.852
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	0.835
Half-life (T1/2):	0.749

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.999
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.654
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.872
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC477165

Natural Product ID:	NPC477165
*Common Name:**	Isoorientin 6'-O-Glucoside Peracetate
IUPAC Name:	[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[5,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-4-oxochromen-6-yl]oxan-2-yl]methoxy]oxan-2-yl]methyl acetate
Synonyms:	Isoorientin 6'-O-Glucoside Peracetate
Standard InCHIKey:	NFJLYZJRENZWOI-FYKFRPLHSA-N
Standard InCHI:	InChI=1S/C49H52O27/c1-19(50)62-17-38-42(68-24(6)55)46(71-27(9)58)48(73-29(11)60)49(76-38)63-18-37-41(67-23(5)54)45(70-26(8)57)47(72-28(10)59)44(75-37)40-36(66-22(4)53)16-35-39(43(40)69-25(7)56)31(61)15-33(74-35)30-12-13-32(64-20(2)51)34(14-30)65-21(3)52/h12-16,37-38,41-42,44-49H,17-18H2,1-11H3/t37-,38-,41-,42-,44+,45+,46+,47+,48-,49-/m1/s1
SMILES:	CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)C3=C(C=C4C(=C3OC(=O)C)C(=O)C=C(O4)C5=CC(=C(C=C5)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44566601
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-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
NPO16297	Gentiana arisanensis	Species	Gentianaceae	Eukaryota	Whole Plant	Yu Shieh, Chiayi Hsieh, Taiwan	1994-APR	PMID[9287421]
NPO16297	Gentiana arisanensis	Species	Gentianaceae	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
Others	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	79.9	%	PMID[9287421]
NPT2	Others	Unspecified		Activity	=	80.5	%	PMID[9287421]

☑ 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 NPC477165 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	514
0.1-0.2	1951
0.2-0.3	4478
0.3-0.4	9866
0.4-0.5	8456
0.5-0.6	4729
0.6-0.7	5976
0.7-0.8	5380
0.8-0.85	872
0.85-0.9	427
0.9-0.95	46
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC414831
0.9627	High Similarity	NPC476180
0.9568	High Similarity	NPC475434
0.9557	High Similarity	NPC477164
0.9503	High Similarity	NPC475214
0.9222	High Similarity	NPC255799
0.9217	High Similarity	NPC25724
0.9217	High Similarity	NPC208668
0.9202	High Similarity	NPC15358
0.9202	High Similarity	NPC475366
0.9202	High Similarity	NPC284277
0.9202	High Similarity	NPC475369
0.9202	High Similarity	NPC475497
0.9193	High Similarity	NPC321478
0.9167	High Similarity	NPC120952
0.9157	High Similarity	NPC256760
0.9136	High Similarity	NPC473516
0.9136	High Similarity	NPC34376
0.9125	High Similarity	NPC155063
0.9107	High Similarity	NPC473862
0.9096	High Similarity	NPC150767
0.9096	High Similarity	NPC78734
0.9096	High Similarity	NPC218488
0.9068	High Similarity	NPC117478
0.9053	High Similarity	NPC475261
0.9053	High Similarity	NPC173837
0.9048	High Similarity	NPC198199
0.9042	High Similarity	NPC475155
0.9042	High Similarity	NPC180918
0.9036	High Similarity	NPC293629
0.9036	High Similarity	NPC195257
0.9036	High Similarity	NPC86008
0.9036	High Similarity	NPC61791
0.9036	High Similarity	NPC209296
0.9018	High Similarity	NPC182045
0.9	High Similarity	NPC473895
0.8994	High Similarity	NPC471669
0.8994	High Similarity	NPC48984
0.8994	High Similarity	NPC89127
0.8982	High Similarity	NPC177731
0.8982	High Similarity	NPC231194
0.8982	High Similarity	NPC194483
0.8982	High Similarity	NPC105095
0.8982	High Similarity	NPC79056
0.8982	High Similarity	NPC293004
0.8982	High Similarity	NPC44328
0.8982	High Similarity	NPC51326
0.8982	High Similarity	NPC52353
0.8976	High Similarity	NPC477502
0.8957	High Similarity	NPC110349
0.8953	High Similarity	NPC25946
0.8953	High Similarity	NPC470713
0.8953	High Similarity	NPC470455
0.8953	High Similarity	NPC470720
0.8953	High Similarity	NPC21359
0.8953	High Similarity	NPC460984
0.8953	High Similarity	NPC470717
0.8953	High Similarity	NPC148710
0.8953	High Similarity	NPC470451
0.8944	High Similarity	NPC471746
0.8941	High Similarity	NPC89052
0.8941	High Similarity	NPC251417
0.8938	High Similarity	NPC40033
0.8935	High Similarity	NPC473327
0.8935	High Similarity	NPC476472
0.8935	High Similarity	NPC294629
0.8935	High Similarity	NPC19108
0.8935	High Similarity	NPC294815
0.8935	High Similarity	NPC16194
0.8935	High Similarity	NPC220173
0.8935	High Similarity	NPC102028
0.8929	High Similarity	NPC9002
0.8929	High Similarity	NPC475669
0.8929	High Similarity	NPC257011
0.8929	High Similarity	NPC137871
0.8929	High Similarity	NPC472386
0.8929	High Similarity	NPC288152
0.8924	High Similarity	NPC476342
0.8922	High Similarity	NPC105283
0.8922	High Similarity	NPC43587
0.8916	High Similarity	NPC236934
0.8916	High Similarity	NPC8856
0.8916	High Similarity	NPC210073
0.8916	High Similarity	NPC5778
0.8916	High Similarity	NPC115674
0.8909	High Similarity	NPC124155
0.8909	High Similarity	NPC88023
0.8909	High Similarity	NPC257566
0.8909	High Similarity	NPC243930
0.8909	High Similarity	NPC309025
0.8902	High Similarity	NPC295625
0.8902	High Similarity	NPC470719
0.8902	High Similarity	NPC473554
0.8896	High Similarity	NPC113055
0.8895	High Similarity	NPC470446
0.8895	High Similarity	NPC470445
0.8895	High Similarity	NPC470449
0.8895	High Similarity	NPC470718
0.8895	High Similarity	NPC470447
0.8895	High Similarity	NPC35924
0.8895	High Similarity	NPC199172
0.8895	High Similarity	NPC162394
0.8895	High Similarity	NPC241781
0.8895	High Similarity	NPC156785
0.8889	High Similarity	NPC192539
0.8889	High Similarity	NPC472726
0.8889	High Similarity	NPC472725
0.8889	High Similarity	NPC471030
0.8882	High Similarity	NPC219043
0.8882	High Similarity	NPC122467
0.8882	High Similarity	NPC202908
0.8882	High Similarity	NPC14187
0.8882	High Similarity	NPC292019
0.8876	High Similarity	NPC204693
0.8876	High Similarity	NPC472993
0.8869	High Similarity	NPC285197
0.8869	High Similarity	NPC210808
0.8869	High Similarity	NPC67105
0.8869	High Similarity	NPC199079
0.8869	High Similarity	NPC76047
0.8868	High Similarity	NPC164299
0.8862	High Similarity	NPC229729
0.8862	High Similarity	NPC135345
0.8855	High Similarity	NPC22832
0.8855	High Similarity	NPC311830
0.8851	High Similarity	NPC64755
0.8848	High Similarity	NPC44947
0.8848	High Similarity	NPC125991
0.8848	High Similarity	NPC298171
0.8844	High Similarity	NPC223860
0.8844	High Similarity	NPC275977
0.8844	High Similarity	NPC249560
0.8837	High Similarity	NPC469371
0.883	High Similarity	NPC472387
0.883	High Similarity	NPC241196
0.883	High Similarity	NPC477895
0.8827	High Similarity	NPC222185
0.8824	High Similarity	NPC108202
0.8824	High Similarity	NPC253685
0.8824	High Similarity	NPC469601
0.8824	High Similarity	NPC142996
0.882	High Similarity	NPC68882
0.8817	High Similarity	NPC155877
0.8817	High Similarity	NPC203259
0.8817	High Similarity	NPC172807
0.8817	High Similarity	NPC211594
0.8817	High Similarity	NPC153755
0.8817	High Similarity	NPC156977
0.8817	High Similarity	NPC3583
0.8817	High Similarity	NPC134532
0.8817	High Similarity	NPC471725
0.8817	High Similarity	NPC60735
0.8817	High Similarity	NPC259152
0.8817	High Similarity	NPC67134
0.8817	High Similarity	NPC267254
0.8817	High Similarity	NPC261254
0.8817	High Similarity	NPC26230
0.8817	High Similarity	NPC254540
0.8817	High Similarity	NPC33054
0.8817	High Similarity	NPC471748
0.8817	High Similarity	NPC47140
0.8817	High Similarity	NPC176740
0.881	High Similarity	NPC5319
0.881	High Similarity	NPC229687
0.881	High Similarity	NPC472381
0.881	High Similarity	NPC227508
0.881	High Similarity	NPC472383
0.8807	High Similarity	NPC264302
0.8802	High Similarity	NPC298666
0.8802	High Similarity	NPC262222
0.8802	High Similarity	NPC68592
0.8795	High Similarity	NPC191306
0.8795	High Similarity	NPC19709
0.8795	High Similarity	NPC222936
0.8795	High Similarity	NPC284960
0.8795	High Similarity	NPC270335
0.8795	High Similarity	NPC29830
0.8793	High Similarity	NPC474093
0.8793	High Similarity	NPC104910
0.8793	High Similarity	NPC33083
0.8788	High Similarity	NPC47923
0.8788	High Similarity	NPC165549
0.8788	High Similarity	NPC101636
0.8786	High Similarity	NPC473883
0.8786	High Similarity	NPC132111
0.878	High Similarity	NPC43761
0.8779	High Similarity	NPC473571
0.8779	High Similarity	NPC473682
0.8779	High Similarity	NPC470444
0.8779	High Similarity	NPC470443
0.8779	High Similarity	NPC110941
0.8779	High Similarity	NPC126784
0.8779	High Similarity	NPC241423
0.8773	High Similarity	NPC295613
0.8773	High Similarity	NPC473657
0.8772	High Similarity	NPC472384
0.8772	High Similarity	NPC472382
0.8772	High Similarity	NPC169733
0.8772	High Similarity	NPC472380
0.8765	High Similarity	NPC4390

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 NPC477165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	430
0.1-0.2	1002
0.2-0.3	2018
0.3-0.4	2718
0.4-0.5	1828
0.5-0.6	783
0.6-0.7	244
0.7-0.8	113
0.8-0.85	7
0.85-0.9	4
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9096	High Similarity	NPD7472	Approved
0.9048	High Similarity	NPD7808	Phase 3
0.9036	High Similarity	NPD7054	Approved
0.8982	High Similarity	NPD7074	Phase 3
0.8876	High Similarity	NPD7251	Discontinued
0.8817	High Similarity	NPD6797	Phase 2
0.881	High Similarity	NPD7804	Clinical (unspecified phase)
0.8614	High Similarity	NPD5494	Approved
0.8605	High Similarity	NPD4338	Clinical (unspecified phase)
0.8598	High Similarity	NPD3817	Phase 2
0.8529	High Similarity	NPD3818	Discontinued
0.8494	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7819	Suspended
0.8412	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD6166	Phase 2
0.8412	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD1934	Approved
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7075	Discontinued
0.8225	Intermediate Similarity	NPD919	Approved
0.8161	Intermediate Similarity	NPD5844	Phase 1
0.8144	Intermediate Similarity	NPD6801	Discontinued
0.8133	Intermediate Similarity	NPD4380	Phase 2
0.8125	Intermediate Similarity	NPD6559	Discontinued
0.8113	Intermediate Similarity	NPD2796	Approved
0.8107	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD2801	Approved
0.8084	Intermediate Similarity	NPD7411	Suspended
0.8068	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7473	Discontinued
0.8034	Intermediate Similarity	NPD8313	Approved
0.8034	Intermediate Similarity	NPD8312	Approved
0.7988	Intermediate Similarity	NPD8455	Phase 2
0.7977	Intermediate Similarity	NPD6232	Discontinued
0.7939	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6959	Discontinued
0.7912	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6799	Approved
0.7879	Intermediate Similarity	NPD1511	Approved
0.7862	Intermediate Similarity	NPD1933	Approved
0.7844	Intermediate Similarity	NPD920	Approved
0.7836	Intermediate Similarity	NPD5402	Approved
0.7816	Intermediate Similarity	NPD1247	Approved
0.7797	Intermediate Similarity	NPD7228	Approved
0.7791	Intermediate Similarity	NPD3882	Suspended
0.7784	Intermediate Similarity	NPD1512	Approved
0.7778	Intermediate Similarity	NPD1465	Phase 2
0.7772	Intermediate Similarity	NPD8151	Discontinued
0.7744	Intermediate Similarity	NPD1243	Approved
0.7738	Intermediate Similarity	NPD5403	Approved
0.773	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5401	Approved
0.7725	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7240	Approved
0.7714	Intermediate Similarity	NPD7199	Phase 2
0.7711	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6599	Discontinued
0.7692	Intermediate Similarity	NPD1653	Approved
0.7688	Intermediate Similarity	NPD7768	Phase 2
0.7683	Intermediate Similarity	NPD1549	Phase 2
0.7627	Intermediate Similarity	NPD3926	Phase 2
0.7627	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7685	Pre-registration
0.7616	Intermediate Similarity	NPD37	Approved
0.7607	Intermediate Similarity	NPD3748	Approved
0.7602	Intermediate Similarity	NPD7783	Phase 2
0.7602	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4965	Approved
0.7586	Intermediate Similarity	NPD4967	Phase 2
0.7586	Intermediate Similarity	NPD4966	Approved
0.756	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD1510	Phase 2
0.7453	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7458	Discontinued
0.7425	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7698	Approved
0.7423	Intermediate Similarity	NPD7696	Phase 3
0.7423	Intermediate Similarity	NPD7435	Discontinued
0.7423	Intermediate Similarity	NPD7697	Approved
0.7398	Intermediate Similarity	NPD7584	Approved
0.7389	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3750	Approved
0.7374	Intermediate Similarity	NPD3787	Discontinued
0.7365	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2935	Discontinued
0.7345	Intermediate Similarity	NPD3749	Approved
0.7341	Intermediate Similarity	NPD3226	Approved
0.733	Intermediate Similarity	NPD5353	Approved
0.7317	Intermediate Similarity	NPD447	Suspended
0.7317	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2533	Approved
0.731	Intermediate Similarity	NPD2534	Approved
0.731	Intermediate Similarity	NPD2532	Approved
0.731	Intermediate Similarity	NPD7583	Approved
0.7308	Intermediate Similarity	NPD3751	Discontinued
0.7306	Intermediate Similarity	NPD8285	Discontinued
0.7305	Intermediate Similarity	NPD7266	Discontinued
0.7296	Intermediate Similarity	NPD7871	Phase 2
0.7296	Intermediate Similarity	NPD7870	Phase 2
0.7292	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7874	Approved
0.7286	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7701	Phase 2
0.7273	Intermediate Similarity	NPD7585	Approved
0.7268	Intermediate Similarity	NPD6777	Approved
0.7268	Intermediate Similarity	NPD6781	Approved
0.7268	Intermediate Similarity	NPD6779	Approved
0.7268	Intermediate Similarity	NPD6776	Approved
0.7268	Intermediate Similarity	NPD6778	Approved
0.7268	Intermediate Similarity	NPD6780	Approved
0.7268	Intermediate Similarity	NPD6782	Approved
0.7256	Intermediate Similarity	NPD1240	Approved
0.7239	Intermediate Similarity	NPD2313	Discontinued
0.7238	Intermediate Similarity	NPD5242	Approved
0.7222	Intermediate Similarity	NPD8127	Discontinued
0.7208	Intermediate Similarity	NPD8320	Phase 1
0.7208	Intermediate Similarity	NPD8319	Approved
0.7202	Intermediate Similarity	NPD2346	Discontinued
0.7194	Intermediate Similarity	NPD5006	Approved
0.7194	Intermediate Similarity	NPD5005	Approved
0.7189	Intermediate Similarity	NPD5953	Discontinued
0.7186	Intermediate Similarity	NPD2799	Discontinued
0.7179	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4628	Phase 3
0.7174	Intermediate Similarity	NPD7286	Phase 2
0.7169	Intermediate Similarity	NPD1607	Approved
0.7165	Intermediate Similarity	NPD7699	Phase 2
0.7165	Intermediate Similarity	NPD7700	Phase 2
0.7159	Intermediate Similarity	NPD6385	Approved
0.7159	Intermediate Similarity	NPD6386	Approved
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7118	Intermediate Similarity	NPD6674	Discontinued
0.7108	Intermediate Similarity	NPD5124	Phase 1
0.7108	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6823	Phase 2
0.7079	Intermediate Similarity	NPD7801	Approved
0.7077	Intermediate Similarity	NPD4420	Approved
0.7071	Intermediate Similarity	NPD7680	Approved
0.7062	Intermediate Similarity	NPD5889	Approved
0.7062	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5890	Approved
0.7048	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1613	Approved
0.7041	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3267	Approved
0.7037	Intermediate Similarity	NPD3266	Approved
0.7027	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7097	Phase 1
0.7018	Intermediate Similarity	NPD2800	Approved
0.7011	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6535	Approved
0.701	Intermediate Similarity	NPD6534	Approved
0.7006	Intermediate Similarity	NPD230	Phase 1
0.6995	Remote Similarity	NPD7229	Phase 3
0.6994	Remote Similarity	NPD2798	Approved
0.6982	Remote Similarity	NPD7033	Discontinued
0.6977	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6651	Approved
0.6954	Remote Similarity	NPD7390	Discontinued
0.6949	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4307	Phase 2
0.6946	Remote Similarity	NPD943	Approved
0.6938	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7549	Discontinued
0.6928	Remote Similarity	NPD3268	Approved
0.6928	Remote Similarity	NPD1296	Phase 2
0.6923	Remote Similarity	NPD4360	Phase 2
0.6923	Remote Similarity	NPD4363	Phase 3
0.6919	Remote Similarity	NPD1652	Phase 2
0.691	Remote Similarity	NPD6585	Discontinued
0.6909	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5710	Approved
0.6902	Remote Similarity	NPD5711	Approved
0.6893	Remote Similarity	NPD7930	Approved
0.689	Remote Similarity	NPD1019	Discontinued
0.6875	Remote Similarity	NPD17	Approved
0.6867	Remote Similarity	NPD3027	Phase 3
0.6848	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6100	Approved
0.6842	Remote Similarity	NPD2438	Suspended
0.6842	Remote Similarity	NPD6099	Approved
0.6839	Remote Similarity	NPD6190	Approved
0.6839	Remote Similarity	NPD3887	Approved
0.6833	Remote Similarity	NPD6844	Discontinued

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