NPASS Compound

Structure

CID116513 OpenBabel06191715472D 35 36 0 0 0 0 0 0 0 0999 V2000 -11.2583 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 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 -2.5981 -0.5000 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 -4.3301 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 -4.3301 -0.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -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 1.7321 1.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 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 0.0000 -0.0000 0.0000 C 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 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 20 2 0 0 0 0 8 21 1 0 0 0 0 9 21 2 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 22 2 0 0 0 0 12 15 2 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 18 28 1 0 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 24 26 2 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 27 30 1 0 0 0 0 27 33 2 0 0 0 0 28 30 2 0 0 0 0 28 34 1 0 0 0 0 29 30 1 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.27
Volume:	527.91
LogP:	7.232
LogD:	4.925
LogS:	-1.952
# Rotatable Bonds:	12
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.19
Synthetic Accessibility Score:	3.051
Fsp3:	0.367
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.111
MDCK Permeability:	2.3453969333786517e-05
Pgp-inhibitor:	0.405
Pgp-substrate:	0.052
Human Intestinal Absorption (HIA):	0.127
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	98.67034912109375%
Volume Distribution (VD):	0.445
Pgp-substrate:	0.47194749116897583%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.889
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.964
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.562
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	6.969
Half-life (T1/2):	0.719

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.408
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.96
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.915
Respiratory Toxicity:	0.151

Download Data

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

Natural Product: NPC116513

Natural Product ID:	NPC116513
*Common Name:**	Bipinnatone A
IUPAC Name:	3-[4-hydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]phenyl]-1-(2,4,6-trihydroxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	SJBBGMVJNAOUOI-VLURGLOZSA-N
Standard InCHI:	InChI=1S/C30H38O5/c1-20(2)7-5-8-21(3)9-6-10-22(4)11-14-24-17-23(12-15-26(24)32)13-16-27(33)30-28(34)18-25(31)19-29(30)35/h7,9,11-12,15,17-19,31-32,34-35H,5-6,8,10,13-14,16H2,1-4H3/b21-9+,22-11+
SMILES:	C/C(=CCc1cc(CCC(=O)c2c(O)cc(cc2O)O)ccc1O)/CC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525006
PubChem CID:	25016410
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003473] 2'-Hydroxy-dihydrochalcones

*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
NPO19134	Boronia bipinnata	Species	Rutaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18662038]
NPO19134	Boronia bipinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	64000.0	nM	PMID[449798]

☑ 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 NPC116513 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	313
0.1-0.2	1473
0.2-0.3	3568
0.3-0.4	11110
0.4-0.5	8256
0.5-0.6	5198
0.6-0.7	6837
0.7-0.8	4515
0.8-0.85	928
0.85-0.9	372
0.9-0.95	103
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC267846
0.9835	High Similarity	NPC190043
0.9835	High Similarity	NPC266689
0.9835	High Similarity	NPC169250
0.9835	High Similarity	NPC23126
0.9835	High Similarity	NPC105157
0.9835	High Similarity	NPC72158
0.9835	High Similarity	NPC162612
0.9835	High Similarity	NPC30501
0.9835	High Similarity	NPC98254
0.9835	High Similarity	NPC103356
0.9835	High Similarity	NPC100067
0.9754	High Similarity	NPC473017
0.9754	High Similarity	NPC221777
0.9754	High Similarity	NPC21305
0.9752	High Similarity	NPC62952
0.9675	High Similarity	NPC474998
0.9583	High Similarity	NPC91105
0.952	High Similarity	NPC475042
0.9504	High Similarity	NPC65761
0.9504	High Similarity	NPC472029
0.95	High Similarity	NPC215392
0.95	High Similarity	NPC242895
0.95	High Similarity	NPC196976
0.9421	High Similarity	NPC32032
0.9421	High Similarity	NPC133909
0.9421	High Similarity	NPC309765
0.9417	High Similarity	NPC149246
0.937	High Similarity	NPC139074
0.937	High Similarity	NPC213485
0.937	High Similarity	NPC40524
0.9365	High Similarity	NPC275504
0.936	High Similarity	NPC476119
0.935	High Similarity	NPC475733
0.9339	High Similarity	NPC19174
0.9339	High Similarity	NPC143427
0.9339	High Similarity	NPC73532
0.9339	High Similarity	NPC156139
0.9339	High Similarity	NPC45438
0.9339	High Similarity	NPC267552
0.9339	High Similarity	NPC115159
0.9339	High Similarity	NPC303737
0.9339	High Similarity	NPC224273
0.9297	High Similarity	NPC166480
0.9297	High Similarity	NPC475088
0.9297	High Similarity	NPC282780
0.9291	High Similarity	NPC175738
0.9286	High Similarity	NPC259942
0.9256	High Similarity	NPC297186
0.9256	High Similarity	NPC229649
0.925	High Similarity	NPC195262
0.925	High Similarity	NPC188814
0.9225	High Similarity	NPC470210
0.9225	High Similarity	NPC130899
0.9225	High Similarity	NPC61153
0.9225	High Similarity	NPC70859
0.9225	High Similarity	NPC283590
0.9206	High Similarity	NPC92624
0.918	High Similarity	NPC226275
0.9174	High Similarity	NPC294037
0.9174	High Similarity	NPC159525
0.9167	High Similarity	NPC209486
0.9167	High Similarity	NPC40649
0.9154	High Similarity	NPC131039
0.9154	High Similarity	NPC264112
0.9154	High Similarity	NPC194764
0.9154	High Similarity	NPC191976
0.9154	High Similarity	NPC13575
0.9154	High Similarity	NPC65005
0.912	High Similarity	NPC8745
0.912	High Similarity	NPC328983
0.9113	High Similarity	NPC13238
0.9106	High Similarity	NPC232708
0.9098	High Similarity	NPC146642
0.9091	High Similarity	NPC158222
0.9091	High Similarity	NPC161617
0.9084	High Similarity	NPC1486
0.9084	High Similarity	NPC186838
0.9084	High Similarity	NPC274109
0.9084	High Similarity	NPC66349
0.9084	High Similarity	NPC150399
0.9084	High Similarity	NPC41461
0.9084	High Similarity	NPC168105
0.9084	High Similarity	NPC477244
0.9084	High Similarity	NPC25287
0.9084	High Similarity	NPC98115
0.9084	High Similarity	NPC477242
0.9084	High Similarity	NPC249606
0.9084	High Similarity	NPC477243
0.9084	High Similarity	NPC12165
0.9083	High Similarity	NPC121259
0.9077	High Similarity	NPC103842
0.9055	High Similarity	NPC109123
0.9048	High Similarity	NPC316625
0.9048	High Similarity	NPC329205
0.904	High Similarity	NPC10926
0.9015	High Similarity	NPC317119
0.9015	High Similarity	NPC472419
0.9015	High Similarity	NPC153979
0.9015	High Similarity	NPC473622
0.9008	High Similarity	NPC118919
0.9008	High Similarity	NPC156092
0.9	High Similarity	NPC294593
0.9	High Similarity	NPC159623
0.9	High Similarity	NPC28753
0.9	High Similarity	NPC18877
0.9	High Similarity	NPC20560
0.9	High Similarity	NPC204960
0.9	High Similarity	NPC82225
0.9	High Similarity	NPC144051
0.8968	High Similarity	NPC473691
0.8947	High Similarity	NPC112789
0.8947	High Similarity	NPC243528
0.8947	High Similarity	NPC242994
0.8947	High Similarity	NPC138099
0.8947	High Similarity	NPC19622
0.8947	High Similarity	NPC251681
0.8947	High Similarity	NPC21350
0.8939	High Similarity	NPC474110
0.8939	High Similarity	NPC44960
0.8931	High Similarity	NPC286336
0.8923	High Similarity	NPC267205
0.8906	High Similarity	NPC120488
0.8906	High Similarity	NPC102829
0.8889	High Similarity	NPC477454
0.8881	High Similarity	NPC181560
0.8881	High Similarity	NPC275903
0.8881	High Similarity	NPC301217
0.8881	High Similarity	NPC470211
0.8881	High Similarity	NPC55018
0.8881	High Similarity	NPC96565
0.8881	High Similarity	NPC169452
0.8881	High Similarity	NPC477956
0.8881	High Similarity	NPC220062
0.8881	High Similarity	NPC472366
0.8881	High Similarity	NPC470986
0.8881	High Similarity	NPC303633
0.8881	High Similarity	NPC216978
0.8855	High Similarity	NPC242294
0.8855	High Similarity	NPC263670
0.8855	High Similarity	NPC16197
0.8855	High Similarity	NPC472365
0.8855	High Similarity	NPC312318
0.8855	High Similarity	NPC337373
0.8855	High Similarity	NPC192304
0.8855	High Similarity	NPC27643
0.8855	High Similarity	NPC139813
0.8855	High Similarity	NPC175098
0.8855	High Similarity	NPC188646
0.8855	High Similarity	NPC56031
0.8846	High Similarity	NPC262359
0.8846	High Similarity	NPC475008
0.8846	High Similarity	NPC186097
0.8846	High Similarity	NPC475009
0.8837	High Similarity	NPC17840
0.8837	High Similarity	NPC233056
0.8837	High Similarity	NPC247477
0.8837	High Similarity	NPC244441
0.8833	High Similarity	NPC118288
0.8833	High Similarity	NPC276111
0.8828	High Similarity	NPC470981
0.8824	High Similarity	NPC297600
0.8815	High Similarity	NPC172250
0.8815	High Similarity	NPC241100
0.8815	High Similarity	NPC159275
0.8815	High Similarity	NPC261227
0.8815	High Similarity	NPC215311
0.8815	High Similarity	NPC144118
0.8815	High Similarity	NPC80962
0.8815	High Similarity	NPC213659
0.8815	High Similarity	NPC11056
0.8815	High Similarity	NPC48624
0.8815	High Similarity	NPC326109
0.8815	High Similarity	NPC69769
0.8815	High Similarity	NPC219917
0.8815	High Similarity	NPC172986
0.8815	High Similarity	NPC235239
0.8815	High Similarity	NPC204985
0.8815	High Similarity	NPC270883
0.8815	High Similarity	NPC259166
0.8806	High Similarity	NPC201395
0.8806	High Similarity	NPC471620
0.8806	High Similarity	NPC472903
0.88	High Similarity	NPC66252
0.8797	High Similarity	NPC53206
0.8797	High Similarity	NPC53001
0.8797	High Similarity	NPC471905
0.8797	High Similarity	NPC290030
0.8797	High Similarity	NPC213603
0.8797	High Similarity	NPC53414
0.879	High Similarity	NPC248363
0.8779	High Similarity	NPC180261
0.8779	High Similarity	NPC212631
0.8779	High Similarity	NPC205468
0.8779	High Similarity	NPC257756
0.8779	High Similarity	NPC215875
0.8779	High Similarity	NPC87231
0.8779	High Similarity	NPC129132
0.8779	High Similarity	NPC37299
0.8779	High Similarity	NPC15834

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 NPC116513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	951
0.2-0.3	1347
0.3-0.4	2736
0.4-0.5	2178
0.5-0.6	1159
0.6-0.7	361
0.7-0.8	104
0.8-0.85	14
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8722	High Similarity	NPD1509	Clinical (unspecified phase)
0.8702	High Similarity	NPD943	Approved
0.8702	High Similarity	NPD1240	Approved
0.8571	High Similarity	NPD1607	Approved
0.8561	High Similarity	NPD4378	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD7390	Discontinued
0.8444	Intermediate Similarity	NPD1510	Phase 2
0.8429	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD1549	Phase 2
0.8168	Intermediate Similarity	NPD1164	Approved
0.8163	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD6651	Approved
0.814	Intermediate Similarity	NPD1201	Approved
0.8138	Intermediate Similarity	NPD4380	Phase 2
0.8095	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD7411	Suspended
0.8054	Intermediate Similarity	NPD7075	Discontinued
0.8047	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD1470	Approved
0.7986	Intermediate Similarity	NPD2796	Approved
0.7986	Intermediate Similarity	NPD5404	Approved
0.7986	Intermediate Similarity	NPD5408	Approved
0.7986	Intermediate Similarity	NPD5405	Approved
0.7986	Intermediate Similarity	NPD5406	Approved
0.7986	Intermediate Similarity	NPD2935	Discontinued
0.7973	Intermediate Similarity	NPD7819	Suspended
0.7973	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6799	Approved
0.7847	Intermediate Similarity	NPD1511	Approved
0.7833	Intermediate Similarity	NPD940	Approved
0.7833	Intermediate Similarity	NPD846	Approved
0.7817	Intermediate Similarity	NPD2800	Approved
0.7785	Intermediate Similarity	NPD6801	Discontinued
0.7785	Intermediate Similarity	NPD1934	Approved
0.7748	Intermediate Similarity	NPD7768	Phase 2
0.7746	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD9266	Approved
0.7742	Intermediate Similarity	NPD74	Approved
0.774	Intermediate Similarity	NPD1512	Approved
0.7737	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2801	Approved
0.7692	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7473	Discontinued
0.7674	Intermediate Similarity	NPD9493	Approved
0.7661	Intermediate Similarity	NPD9264	Approved
0.7661	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD9263	Approved
0.7661	Intermediate Similarity	NPD9267	Approved
0.766	Intermediate Similarity	NPD2799	Discontinued
0.7651	Intermediate Similarity	NPD6599	Discontinued
0.7639	Intermediate Similarity	NPD3750	Approved
0.7632	Intermediate Similarity	NPD3882	Suspended
0.7628	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6232	Discontinued
0.7595	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1243	Approved
0.7552	Intermediate Similarity	NPD2344	Approved
0.7551	Intermediate Similarity	NPD2532	Approved
0.7551	Intermediate Similarity	NPD2533	Approved
0.7551	Intermediate Similarity	NPD2534	Approved
0.7548	Intermediate Similarity	NPD6959	Discontinued
0.7538	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.7484	Intermediate Similarity	NPD7286	Phase 2
0.7483	Intermediate Similarity	NPD1551	Phase 2
0.7468	Intermediate Similarity	NPD3749	Approved
0.7445	Intermediate Similarity	NPD2798	Approved
0.7424	Intermediate Similarity	NPD9545	Approved
0.7417	Intermediate Similarity	NPD2860	Approved
0.7417	Intermediate Similarity	NPD2859	Approved
0.7407	Intermediate Similarity	NPD9269	Phase 2
0.7405	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6166	Phase 2
0.7405	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5953	Discontinued
0.7385	Intermediate Similarity	NPD9281	Approved
0.7368	Intermediate Similarity	NPD9268	Approved
0.7357	Intermediate Similarity	NPD2313	Discontinued
0.7347	Intermediate Similarity	NPD2309	Approved
0.7339	Intermediate Similarity	NPD9261	Approved
0.7338	Intermediate Similarity	NPD3817	Phase 2
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD2933	Approved
0.7333	Intermediate Similarity	NPD2934	Approved
0.7333	Intermediate Similarity	NPD920	Approved
0.7329	Intermediate Similarity	NPD7074	Phase 3
0.7329	Intermediate Similarity	NPD2654	Approved
0.7317	Intermediate Similarity	NPD1242	Phase 1
0.7315	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3748	Approved
0.7279	Intermediate Similarity	NPD9717	Approved
0.7279	Intermediate Similarity	NPD3972	Approved
0.7267	Intermediate Similarity	NPD6020	Phase 2
0.7267	Intermediate Similarity	NPD7054	Approved
0.7266	Intermediate Similarity	NPD4750	Phase 3
0.7261	Intermediate Similarity	NPD5494	Approved
0.7241	Intermediate Similarity	NPD6099	Approved
0.7241	Intermediate Similarity	NPD6100	Approved
0.7236	Intermediate Similarity	NPD3020	Approved
0.7234	Intermediate Similarity	NPD3268	Approved
0.7234	Intermediate Similarity	NPD3764	Approved
0.7222	Intermediate Similarity	NPD7472	Approved
0.7219	Intermediate Similarity	NPD5403	Approved
0.7205	Intermediate Similarity	NPD3818	Discontinued
0.7203	Intermediate Similarity	NPD230	Phase 1
0.72	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3019	Approved
0.7185	Intermediate Similarity	NPD2932	Approved
0.7181	Intermediate Similarity	NPD3300	Phase 2
0.7134	Intermediate Similarity	NPD7251	Discontinued
0.7134	Intermediate Similarity	NPD6559	Discontinued
0.7124	Intermediate Similarity	NPD3226	Approved
0.7124	Intermediate Similarity	NPD7458	Discontinued
0.7122	Intermediate Similarity	NPD2797	Approved
0.7113	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7808	Phase 3
0.7086	Intermediate Similarity	NPD5401	Approved
0.708	Intermediate Similarity	NPD422	Phase 1
0.708	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2346	Discontinued
0.7073	Intermediate Similarity	NPD6797	Phase 2
0.707	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4628	Phase 3
0.7047	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3400	Discontinued
0.7008	Intermediate Similarity	NPD1237	Approved
0.7006	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1809	Phase 2
0.6981	Remote Similarity	NPD919	Approved
0.6972	Remote Similarity	NPD4908	Phase 1
0.6967	Remote Similarity	NPD845	Approved
0.6957	Remote Similarity	NPD5710	Approved
0.6957	Remote Similarity	NPD5711	Approved
0.6951	Remote Similarity	NPD5844	Phase 1
0.6944	Remote Similarity	NPD520	Approved
0.6939	Remote Similarity	NPD7033	Discontinued
0.6939	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4308	Phase 3
0.6933	Remote Similarity	NPD7003	Approved
0.6929	Remote Similarity	NPD1930	Approved
0.6929	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1929	Approved
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3926	Phase 2
0.6912	Remote Similarity	NPD1548	Phase 1
0.6909	Remote Similarity	NPD1729	Discontinued
0.6899	Remote Similarity	NPD5402	Approved
0.6897	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1247	Approved
0.6886	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4363	Phase 3
0.6879	Remote Similarity	NPD3266	Approved
0.6879	Remote Similarity	NPD4360	Phase 2
0.6879	Remote Similarity	NPD3267	Approved
0.687	Remote Similarity	NPD3022	Approved
0.687	Remote Similarity	NPD3021	Approved
0.6866	Remote Similarity	NPD5951	Approved
0.6842	Remote Similarity	NPD7635	Approved
0.6839	Remote Similarity	NPD4361	Phase 2
0.6839	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1610	Phase 2
0.6822	Remote Similarity	NPD5048	Discontinued
0.6809	Remote Similarity	NPD3225	Approved
0.6809	Remote Similarity	NPD1876	Approved
0.6806	Remote Similarity	NPD4625	Phase 3
0.6792	Remote Similarity	NPD2296	Approved
0.6788	Remote Similarity	NPD1759	Phase 1
0.6786	Remote Similarity	NPD1608	Approved
0.678	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3023	Approved
0.6763	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3026	Approved
0.6759	Remote Similarity	NPD1296	Phase 2
0.6759	Remote Similarity	NPD411	Approved
0.6739	Remote Similarity	NPD3025	Approved
0.6739	Remote Similarity	NPD1651	Approved
0.6739	Remote Similarity	NPD3024	Approved
0.6738	Remote Similarity	NPD1755	Approved
0.6735	Remote Similarity	NPD447	Suspended
0.6735	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5124	Phase 1
0.6735	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1933	Approved
0.6733	Remote Similarity	NPD1471	Phase 3
0.673	Remote Similarity	NPD1465	Phase 2
0.6726	Remote Similarity	NPD6104	Discontinued
0.6725	Remote Similarity	NPD8150	Discontinued
0.672	Remote Similarity	NPD844	Approved
0.6715	Remote Similarity	NPD1758	Phase 1

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