NPASS Compound

Structure

NPC472131 OpenBabel07101718292D 46 50 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 2 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 6.9282 4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 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 6.0622 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 6.0622 2.5000 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 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 13 1 0 0 0 0 5 15 2 0 0 0 0 6 7 1 0 0 0 0 7 40 1 0 0 0 0 8 30 1 0 0 0 0 9 14 2 0 0 0 0 9 42 1 0 0 0 0 10 41 1 0 0 0 0 11 2 1 1 0 0 0 11 12 1 0 0 0 0 11 27 1 0 0 0 0 12 6 1 1 0 0 0 12 14 1 0 0 0 0 13 24 2 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 24 1 0 0 0 0 15 31 1 0 0 0 0 16 8 1 1 0 0 0 16 18 1 0 0 0 0 16 43 1 0 0 0 0 17 10 1 6 0 0 0 17 19 1 0 0 0 0 17 44 1 0 0 0 0 18 20 1 0 0 0 0 18 32 1 6 0 0 0 19 21 1 0 0 0 0 19 33 1 1 0 0 0 20 22 1 0 0 0 0 20 34 1 1 0 0 0 21 23 1 0 0 0 0 21 35 1 6 0 0 0 22 28 1 0 0 0 0 22 36 1 6 0 0 0 23 29 1 0 0 0 0 23 37 1 1 0 0 0 24 45 1 0 0 0 0 25 38 2 0 0 0 0 25 41 1 0 0 0 0 26 39 2 0 0 0 0 26 40 1 0 0 0 0 27 42 1 0 0 0 0 27 46 1 6 0 0 0 28 43 1 0 0 0 0 28 45 1 1 0 0 0 29 44 1 0 0 0 0 29 46 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	656.2
Volume:	598.336
LogP:	0.114
LogD:	-0.042
LogS:	-2.214
# Rotatable Bonds:	10
TPSA:	260.59
# H-Bond Aceptor:	17
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.098
Synthetic Accessibility Score:	5.302
Fsp3:	0.586
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.56
MDCK Permeability:	0.00011661254393402487
Pgp-inhibitor:	0.0
Pgp-substrate:	0.889
Human Intestinal Absorption (HIA):	0.98
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.184
Plasma Protein Binding (PPB):	36.0770378112793%
Volume Distribution (VD):	0.429
Pgp-substrate:	27.531179428100586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.051

ADMET: Excretion

Clearance (CL):	1.084
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.55
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.13
Carcinogencity:	0.532
Eye Corrosion:	0.003
Eye Irritation:	0.063
Respiratory Toxicity:	0.057

Download Data

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

Natural Product: NPC472131

Natural Product ID:	NPC472131
*Common Name:**	FORGYJSGKBVGSV-ANKUWFSSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FORGYJSGKBVGSV-ANKUWFSSSA-N
Standard InCHI:	InChI=1S/C29H36O17/c1-2-11-12-6-7-40-26(39)14(12)9-42-27(11)46-29-23(37)21(35)19(33)17(44-29)10-41-25(38)13-4-3-5-15(31)24(13)45-28-22(36)20(34)18(32)16(8-30)43-28/h2-5,9,11-12,16-23,27-37H,1,6-8,10H2/t11-,12+,16-,17-,18-,19-,20+,21+,22-,23-,27+,28+,29+/m1/s1
SMILES:	C=C[C@H]1[C@@H](OC=C2[C@H]1CCOC2=O)O[C@@H]1O[C@H](COC(=O)c2cccc(c2O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338643
PubChem CID:	n.a.
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:0004165] Phenolic 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
NPO32460	Gentianella azurea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24806310]
NPO32460	Gentianella azurea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25442320]

☑ 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	>	200000.0	nM	PMID[548162]

☑ 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 NPC472131 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	405
0.1-0.2	1622
0.2-0.3	3642
0.3-0.4	8333
0.4-0.5	9225
0.5-0.6	5884
0.6-0.7	7069
0.7-0.8	5381
0.8-0.85	941
0.85-0.9	188
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472130
0.981	High Similarity	NPC472133
0.9748	High Similarity	NPC43434
0.9748	High Similarity	NPC472129
0.9295	High Similarity	NPC472128
0.9295	High Similarity	NPC472127
0.8988	High Similarity	NPC120952
0.8976	High Similarity	NPC180918
0.897	High Similarity	NPC86008
0.8922	High Similarity	NPC163165
0.8909	High Similarity	NPC298847
0.8876	High Similarity	NPC173837
0.8869	High Similarity	NPC198199
0.8869	High Similarity	NPC253685
0.8862	High Similarity	NPC259152
0.8862	High Similarity	NPC3583
0.8855	High Similarity	NPC195257
0.8855	High Similarity	NPC105283
0.8855	High Similarity	NPC209296
0.8848	High Similarity	NPC8856
0.8837	High Similarity	NPC295625
0.8837	High Similarity	NPC470719
0.8837	High Similarity	NPC473554
0.8834	High Similarity	NPC71780
0.8834	High Similarity	NPC217950
0.883	High Similarity	NPC470445
0.883	High Similarity	NPC470449
0.883	High Similarity	NPC470446
0.883	High Similarity	NPC470718
0.883	High Similarity	NPC470447
0.8817	High Similarity	NPC471669
0.8817	High Similarity	NPC89127
0.8817	High Similarity	NPC472992
0.8817	High Similarity	NPC472991
0.8817	High Similarity	NPC219043
0.881	High Similarity	NPC472993
0.881	High Similarity	NPC204693
0.8802	High Similarity	NPC204937
0.8802	High Similarity	NPC285197
0.8802	High Similarity	NPC79056
0.8802	High Similarity	NPC177731
0.8802	High Similarity	NPC149011
0.8802	High Similarity	NPC51326
0.8802	High Similarity	NPC44328
0.8802	High Similarity	NPC105095
0.8802	High Similarity	NPC231194
0.8795	High Similarity	NPC116745
0.8795	High Similarity	NPC45400
0.879	High Similarity	NPC83975
0.8788	High Similarity	NPC99216
0.878	High Similarity	NPC22324
0.8779	High Similarity	NPC249560
0.8779	High Similarity	NPC25946
0.8779	High Similarity	NPC470720
0.8779	High Similarity	NPC21359
0.8779	High Similarity	NPC470713
0.8779	High Similarity	NPC275977
0.8779	High Similarity	NPC470455
0.8779	High Similarity	NPC470717
0.8779	High Similarity	NPC223860
0.8779	High Similarity	NPC470451
0.8779	High Similarity	NPC460984
0.8765	High Similarity	NPC476618
0.8765	High Similarity	NPC476620
0.8765	High Similarity	NPC476619
0.8765	High Similarity	NPC251417
0.8765	High Similarity	NPC89052
0.8765	High Similarity	NPC476621
0.8765	High Similarity	NPC113836
0.8765	High Similarity	NPC476622
0.8765	High Similarity	NPC253521
0.8765	High Similarity	NPC476623
0.8765	High Similarity	NPC37668
0.8757	High Similarity	NPC142996
0.8757	High Similarity	NPC476472
0.8757	High Similarity	NPC473327
0.8757	High Similarity	NPC16194
0.8757	High Similarity	NPC220173
0.8757	High Similarity	NPC294815
0.8757	High Similarity	NPC19108
0.8757	High Similarity	NPC102028
0.875	High Similarity	NPC254540
0.875	High Similarity	NPC60735
0.875	High Similarity	NPC47140
0.875	High Similarity	NPC26230
0.875	High Similarity	NPC172807
0.875	High Similarity	NPC211594
0.875	High Similarity	NPC67134
0.8743	High Similarity	NPC229687
0.8743	High Similarity	NPC658
0.8743	High Similarity	NPC197708
0.8743	High Similarity	NPC43587
0.8743	High Similarity	NPC61791
0.8743	High Similarity	NPC293629
0.8735	High Similarity	NPC99957
0.8735	High Similarity	NPC181616
0.8735	High Similarity	NPC210073
0.8735	High Similarity	NPC115674
0.8728	High Similarity	NPC33083
0.8727	High Similarity	NPC168822
0.8727	High Similarity	NPC127415
0.8727	High Similarity	NPC88043
0.8727	High Similarity	NPC191306
0.8727	High Similarity	NPC270335
0.8721	High Similarity	NPC199172
0.8721	High Similarity	NPC241781
0.8721	High Similarity	NPC162394
0.8721	High Similarity	NPC35924
0.8721	High Similarity	NPC156785
0.872	High Similarity	NPC132737
0.8713	High Similarity	NPC192539
0.8713	High Similarity	NPC473571
0.8713	High Similarity	NPC470443
0.8713	High Similarity	NPC126784
0.8713	High Similarity	NPC471030
0.8713	High Similarity	NPC470444
0.8713	High Similarity	NPC110941
0.8713	High Similarity	NPC241423
0.8713	High Similarity	NPC473682
0.8706	High Similarity	NPC48984
0.8706	High Similarity	NPC61904
0.8706	High Similarity	NPC14187
0.8706	High Similarity	NPC202908
0.8706	High Similarity	NPC144097
0.8706	High Similarity	NPC211532
0.8706	High Similarity	NPC233994
0.8706	High Similarity	NPC255799
0.8706	High Similarity	NPC8573
0.8706	High Similarity	NPC169733
0.8706	High Similarity	NPC292019
0.8706	High Similarity	NPC122467
0.8706	High Similarity	NPC473862
0.8698	High Similarity	NPC88560
0.8698	High Similarity	NPC172033
0.8698	High Similarity	NPC51774
0.8698	High Similarity	NPC208668
0.8698	High Similarity	NPC239549
0.8698	High Similarity	NPC236191
0.8698	High Similarity	NPC175230
0.8698	High Similarity	NPC4390
0.8696	High Similarity	NPC279281
0.8696	High Similarity	NPC191046
0.8696	High Similarity	NPC194095
0.8696	High Similarity	NPC327032
0.8696	High Similarity	NPC230439
0.8696	High Similarity	NPC299761
0.8696	High Similarity	NPC92153
0.869	High Similarity	NPC259896
0.869	High Similarity	NPC254855
0.869	High Similarity	NPC29958
0.869	High Similarity	NPC34287
0.869	High Similarity	NPC255157
0.869	High Similarity	NPC218488
0.869	High Similarity	NPC67326
0.869	High Similarity	NPC136042
0.869	High Similarity	NPC156869
0.869	High Similarity	NPC67105
0.869	High Similarity	NPC155763
0.869	High Similarity	NPC471416
0.869	High Similarity	NPC235260
0.869	High Similarity	NPC20505
0.8683	High Similarity	NPC58716
0.8683	High Similarity	NPC146792
0.8683	High Similarity	NPC45618
0.8683	High Similarity	NPC275454
0.8683	High Similarity	NPC229729
0.8678	High Similarity	NPC72554
0.8678	High Similarity	NPC30011
0.8678	High Similarity	NPC97817
0.8675	High Similarity	NPC22832
0.8675	High Similarity	NPC165720
0.8675	High Similarity	NPC15358
0.8675	High Similarity	NPC311830
0.8675	High Similarity	NPC475366
0.8675	High Similarity	NPC284277
0.8675	High Similarity	NPC475497
0.8671	High Similarity	NPC472722
0.8667	High Similarity	NPC77660
0.8667	High Similarity	NPC189142
0.8663	High Similarity	NPC469371
0.8659	High Similarity	NPC328093
0.8655	High Similarity	NPC267680
0.8655	High Similarity	NPC35167
0.8655	High Similarity	NPC472387
0.8655	High Similarity	NPC217387
0.8655	High Similarity	NPC475261
0.8655	High Similarity	NPC293626
0.8655	High Similarity	NPC196127
0.8655	High Similarity	NPC258044
0.8655	High Similarity	NPC139571
0.8655	High Similarity	NPC217520
0.865	High Similarity	NPC133984
0.8647	High Similarity	NPC237435
0.8647	High Similarity	NPC49344
0.8647	High Similarity	NPC43211
0.8647	High Similarity	NPC223426
0.8647	High Similarity	NPC135277
0.8647	High Similarity	NPC214621
0.8647	High Similarity	NPC169645
0.8647	High Similarity	NPC115760

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 NPC472131 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	934
0.2-0.3	1992
0.3-0.4	2647
0.4-0.5	1857
0.5-0.6	943
0.6-0.7	304
0.7-0.8	106
0.8-0.85	7
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8916	High Similarity	NPD7472	Approved
0.8855	High Similarity	NPD7054	Approved
0.8802	High Similarity	NPD7074	Phase 3
0.8698	High Similarity	NPD7251	Discontinued
0.8647	High Similarity	NPD4338	Clinical (unspecified phase)
0.8647	High Similarity	NPD7808	Phase 3
0.8639	High Similarity	NPD6797	Phase 2
0.8571	High Similarity	NPD3818	Discontinued
0.8488	Intermediate Similarity	NPD8312	Approved
0.8488	Intermediate Similarity	NPD8313	Approved
0.8313	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD7685	Pre-registration
0.816	Intermediate Similarity	NPD1653	Approved
0.8144	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6166	Phase 2
0.8092	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD5402	Approved
0.7964	Intermediate Similarity	NPD1934	Approved
0.7931	Intermediate Similarity	NPD7228	Approved
0.7917	Intermediate Similarity	NPD2801	Approved
0.7898	Intermediate Similarity	NPD447	Suspended
0.787	Intermediate Similarity	NPD3817	Phase 2
0.7857	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD8455	Phase 2
0.7811	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD1465	Phase 2
0.7785	Intermediate Similarity	NPD1933	Approved
0.7771	Intermediate Similarity	NPD5403	Approved
0.7764	Intermediate Similarity	NPD7266	Discontinued
0.7753	Intermediate Similarity	NPD6559	Discontinued
0.7738	Intermediate Similarity	NPD4380	Phase 2
0.7719	Intermediate Similarity	NPD3882	Suspended
0.7697	Intermediate Similarity	NPD1511	Approved
0.7688	Intermediate Similarity	NPD5494	Approved
0.7674	Intermediate Similarity	NPD7075	Discontinued
0.7651	Intermediate Similarity	NPD5401	Approved
0.7622	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1512	Approved
0.7584	Intermediate Similarity	NPD5844	Phase 1
0.7582	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7473	Discontinued
0.7556	Intermediate Similarity	NPD7240	Approved
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.7528	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7783	Phase 2
0.7448	Intermediate Similarity	NPD7435	Discontinued
0.7443	Intermediate Similarity	NPD7199	Phase 2
0.7442	Intermediate Similarity	NPD37	Approved
0.7442	Intermediate Similarity	NPD6801	Discontinued
0.7436	Intermediate Similarity	NPD8151	Discontinued
0.7414	Intermediate Similarity	NPD4967	Phase 2
0.7414	Intermediate Similarity	NPD4965	Approved
0.7414	Intermediate Similarity	NPD4966	Approved
0.7401	Intermediate Similarity	NPD3787	Discontinued
0.7394	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1551	Phase 2
0.7365	Intermediate Similarity	NPD6190	Approved
0.7356	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1091	Approved
0.7351	Intermediate Similarity	NPD8150	Discontinued
0.7346	Intermediate Similarity	NPD230	Phase 1
0.7337	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8319	Approved
0.732	Intermediate Similarity	NPD8320	Phase 1
0.7305	Intermediate Similarity	NPD4628	Phase 3
0.7292	Intermediate Similarity	NPD6776	Approved
0.7292	Intermediate Similarity	NPD6781	Approved
0.7292	Intermediate Similarity	NPD6777	Approved
0.7292	Intermediate Similarity	NPD6779	Approved
0.7292	Intermediate Similarity	NPD6782	Approved
0.7292	Intermediate Similarity	NPD6778	Approved
0.7292	Intermediate Similarity	NPD6780	Approved
0.7289	Intermediate Similarity	NPD1549	Phase 2
0.7283	Intermediate Similarity	NPD7411	Suspended
0.7278	Intermediate Similarity	NPD6799	Approved
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1203	Approved
0.7268	Intermediate Similarity	NPD7698	Approved
0.7268	Intermediate Similarity	NPD7696	Phase 3
0.7268	Intermediate Similarity	NPD7697	Approved
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3226	Approved
0.7263	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6832	Phase 2
0.7247	Intermediate Similarity	NPD6959	Discontinued
0.7229	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7874	Approved
0.7216	Intermediate Similarity	NPD6823	Phase 2
0.7216	Intermediate Similarity	NPD7768	Phase 2
0.7208	Intermediate Similarity	NPD7701	Phase 2
0.7202	Intermediate Similarity	NPD3750	Approved
0.7202	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD9717	Approved
0.7169	Intermediate Similarity	NPD2935	Discontinued
0.7168	Intermediate Similarity	NPD7458	Discontinued
0.7166	Intermediate Similarity	NPD8434	Phase 2
0.716	Intermediate Similarity	NPD2313	Discontinued
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.715	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7136	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.7126	Intermediate Similarity	NPD6599	Discontinued
0.7108	Intermediate Similarity	NPD1510	Phase 2
0.71	Intermediate Similarity	NPD7801	Approved
0.7098	Intermediate Similarity	NPD7699	Phase 2
0.7098	Intermediate Similarity	NPD7700	Phase 2
0.7092	Intermediate Similarity	NPD7680	Approved
0.7081	Intermediate Similarity	NPD9494	Approved
0.7079	Intermediate Similarity	NPD3749	Approved
0.7073	Intermediate Similarity	NPD1613	Approved
0.7073	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2796	Approved
0.7062	Intermediate Similarity	NPD5353	Approved
0.7055	Intermediate Similarity	NPD411	Approved
0.7045	Intermediate Similarity	NPD6844	Discontinued
0.7039	Intermediate Similarity	NPD919	Approved
0.7035	Intermediate Similarity	NPD2533	Approved
0.7035	Intermediate Similarity	NPD2534	Approved
0.7035	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2532	Approved
0.7031	Intermediate Similarity	NPD6534	Approved
0.7031	Intermediate Similarity	NPD6535	Approved
0.7019	Intermediate Similarity	NPD2798	Approved
0.7006	Intermediate Similarity	NPD2799	Discontinued
0.7006	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD3225	Approved
0.6985	Remote Similarity	NPD7584	Approved
0.6979	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6213	Phase 3
0.6979	Remote Similarity	NPD6212	Phase 3
0.6957	Remote Similarity	NPD2797	Approved
0.6951	Remote Similarity	NPD3268	Approved
0.6946	Remote Similarity	NPD7097	Phase 1
0.6941	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1019	Discontinued
0.6905	Remote Similarity	NPD3748	Approved
0.6886	Remote Similarity	NPD6653	Approved
0.6885	Remote Similarity	NPD3926	Phase 2
0.6875	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD1247	Approved
0.6867	Remote Similarity	NPD943	Approved
0.6866	Remote Similarity	NPD7585	Approved
0.6859	Remote Similarity	NPD9493	Approved
0.6848	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7930	Approved
0.6826	Remote Similarity	NPD6355	Discontinued
0.6816	Remote Similarity	NPD7583	Approved
0.6813	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5647	Approved
0.6805	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4308	Phase 3
0.6802	Remote Similarity	NPD8166	Discontinued
0.6798	Remote Similarity	NPD6386	Approved
0.6798	Remote Similarity	NPD6385	Approved
0.6788	Remote Similarity	NPD3027	Phase 3
0.6786	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1608	Approved
0.677	Remote Similarity	NPD9269	Phase 2
0.6768	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1240	Approved
0.6765	Remote Similarity	NPD6100	Approved
0.6765	Remote Similarity	NPD6099	Approved
0.6761	Remote Similarity	NPD920	Approved
0.6757	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4420	Approved
0.6744	Remote Similarity	NPD1652	Phase 2
0.6743	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5124	Phase 1
0.6725	Remote Similarity	NPD6005	Phase 3
0.6725	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6002	Phase 3
0.6725	Remote Similarity	NPD6004	Phase 3
0.672	Remote Similarity	NPD7039	Approved
0.672	Remote Similarity	NPD7038	Approved
0.6717	Remote Similarity	NPD8285	Discontinued
0.6705	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6273	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