NPASS Compound

Structure

NPC70859 OpenBabel07101719252D 30 31 0 0 1 0 0 0 0 0999 V2000 -0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -0.8660 -3.5000 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 3.4641 -3.0000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 -1.7321 -0.0000 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 -0.8660 -4.5000 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 3.4641 -2.0000 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 5.1962 -3.0000 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 2.5981 -0.5000 0.0000 C 0 0 1 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 0.0000 0.0000 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 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 -0.0000 1.0000 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 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 9 1 0 0 0 0 5 15 2 0 0 0 0 6 12 1 0 0 0 0 6 16 2 0 0 0 0 7 10 1 0 0 0 0 7 17 2 0 0 0 0 8 11 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 18 23 1 0 0 0 0 19 26 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 25 1 0 0 0 0 22 27 1 1 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	786.29
Volume:	766.701
LogP:	5.282
LogD:	2.572
LogS:	-3.58
# Rotatable Bonds:	5
TPSA:	185.74
# H-Bond Aceptor:	14
# H-Bond Donor:	3
# Rings:	9
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	6.385
Fsp3:	0.512
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.987
MDCK Permeability:	3.8789366954006255e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.422

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	95.5250015258789%
Volume Distribution (VD):	0.579
Pgp-substrate:	5.819576740264893%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.872
CYP2C19-inhibitor:	0.084
CYP2C19-substrate:	0.291
CYP2C9-inhibitor:	0.565
CYP2C9-substrate:	0.161
CYP2D6-inhibitor:	0.067
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.379
CYP3A4-substrate:	0.803

ADMET: Excretion

Clearance (CL):	4.486
Half-life (T1/2):	0.157

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.891
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.927
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.93
Carcinogencity:	0.943
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.394

Download Data

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

Natural Product: NPC70859

Natural Product ID:	NPC70859
*Common Name:**	Lespeflorin C6
IUPAC Name:	(2S)-1-[2,4-dihydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]-2-hydroxy-3-(4-hydroxyphenyl)propan-1-one
Synonyms:	Lespeflorin C6
Standard InCHIKey:	VMDPAFNBQPVUSZ-QFIPXVFZSA-N
Standard InCHI:	InChI=1S/C25H30O5/c1-15(2)5-9-18-14-21(24(29)20(23(18)28)12-6-16(3)4)25(30)22(27)13-17-7-10-19(26)11-8-17/h5-8,10-11,14,22,26-29H,9,12-13H2,1-4H3/t22-/m0/s1
SMILES:	CC(=CCc1cc(c(c(CC=C(C)C)c1O)O)C(=O)[C@H](Cc1ccc(cc1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560044
PubChem CID:	25243325
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
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	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	=	22000.0	nM	PMID[465158]

☑ 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 NPC70859 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	315
0.1-0.2	1296
0.2-0.3	3331
0.3-0.4	8993
0.4-0.5	10495
0.5-0.6	4335
0.6-0.7	6643
0.7-0.8	5705
0.8-0.85	1163
0.85-0.9	361
0.9-0.95	43
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC283590
1.0	High Similarity	NPC130899
1.0	High Similarity	NPC61153
0.9844	High Similarity	NPC213485
0.9844	High Similarity	NPC40524
0.9844	High Similarity	NPC139074
0.9688	High Similarity	NPC475042
0.9531	High Similarity	NPC102829
0.9531	High Similarity	NPC120488
0.9412	High Similarity	NPC148545
0.938	High Similarity	NPC474998
0.9375	High Similarity	NPC100067
0.9375	High Similarity	NPC162612
0.9375	High Similarity	NPC169250
0.9375	High Similarity	NPC103356
0.9375	High Similarity	NPC105157
0.9375	High Similarity	NPC98254
0.9375	High Similarity	NPC23126
0.9375	High Similarity	NPC190043
0.9375	High Similarity	NPC266689
0.9375	High Similarity	NPC72158
0.9375	High Similarity	NPC30501
0.9343	High Similarity	NPC301751
0.9343	High Similarity	NPC245482
0.9302	High Similarity	NPC221777
0.9302	High Similarity	NPC473017
0.9302	High Similarity	NPC21305
0.9297	High Similarity	NPC267846
0.9297	High Similarity	NPC62952
0.9231	High Similarity	NPC476119
0.9225	High Similarity	NPC116513
0.9197	High Similarity	NPC321980
0.9197	High Similarity	NPC470087
0.9104	High Similarity	NPC470210
0.9091	High Similarity	NPC275504
0.9065	High Similarity	NPC117836
0.9065	High Similarity	NPC471906
0.9065	High Similarity	NPC475705
0.9065	High Similarity	NPC51887
0.9065	High Similarity	NPC476178
0.9058	High Similarity	NPC470089
0.9051	High Similarity	NPC470211
0.9044	High Similarity	NPC175552
0.903	High Similarity	NPC282780
0.903	High Similarity	NPC166480
0.8984	High Similarity	NPC91105
0.8984	High Similarity	NPC32032
0.8984	High Similarity	NPC133909
0.8984	High Similarity	NPC309765
0.8951	High Similarity	NPC61258
0.8936	High Similarity	NPC316769
0.8923	High Similarity	NPC475733
0.8921	High Similarity	NPC469404
0.8921	High Similarity	NPC135524
0.8921	High Similarity	NPC474961
0.8915	High Similarity	NPC65761
0.8915	High Similarity	NPC472029
0.8906	High Similarity	NPC73532
0.8906	High Similarity	NPC156139
0.8906	High Similarity	NPC19174
0.8906	High Similarity	NPC215392
0.8906	High Similarity	NPC267552
0.8906	High Similarity	NPC303737
0.8906	High Similarity	NPC115159
0.8906	High Similarity	NPC143427
0.8906	High Similarity	NPC196976
0.8906	High Similarity	NPC45438
0.8906	High Similarity	NPC242895
0.8906	High Similarity	NPC224273
0.8897	High Similarity	NPC264112
0.8897	High Similarity	NPC131039
0.8897	High Similarity	NPC194764
0.8897	High Similarity	NPC65005
0.8881	High Similarity	NPC478190
0.8881	High Similarity	NPC175738
0.8873	High Similarity	NPC51070
0.8873	High Similarity	NPC222298
0.8865	High Similarity	NPC328623
0.8855	High Similarity	NPC8745
0.8849	High Similarity	NPC326109
0.8849	High Similarity	NPC144118
0.8849	High Similarity	NPC213659
0.8849	High Similarity	NPC48624
0.8849	High Similarity	NPC204045
0.8849	High Similarity	NPC259166
0.8849	High Similarity	NPC219917
0.8849	High Similarity	NPC305845
0.8849	High Similarity	NPC204985
0.8849	High Similarity	NPC172250
0.8849	High Similarity	NPC80962
0.8849	High Similarity	NPC215311
0.8846	High Similarity	NPC13238
0.8841	High Similarity	NPC19622
0.8841	High Similarity	NPC21350
0.8841	High Similarity	NPC112789
0.8832	High Similarity	NPC150399
0.8832	High Similarity	NPC274109
0.8832	High Similarity	NPC477244
0.8832	High Similarity	NPC168105
0.8832	High Similarity	NPC25287
0.8832	High Similarity	NPC66349
0.8832	High Similarity	NPC186838
0.8832	High Similarity	NPC249606
0.8832	High Similarity	NPC170742
0.8832	High Similarity	NPC44960
0.8832	High Similarity	NPC477242
0.8832	High Similarity	NPC477243
0.8832	High Similarity	NPC41461
0.8832	High Similarity	NPC1486
0.8832	High Similarity	NPC12165
0.8832	High Similarity	NPC98115
0.8832	High Similarity	NPC474110
0.8828	High Similarity	NPC171651
0.8828	High Similarity	NPC149246
0.8828	High Similarity	NPC297186
0.8828	High Similarity	NPC35567
0.8828	High Similarity	NPC243171
0.8803	High Similarity	NPC472629
0.8797	High Similarity	NPC92624
0.8797	High Similarity	NPC109123
0.8794	High Similarity	NPC244691
0.8786	High Similarity	NPC26051
0.8786	High Similarity	NPC137649
0.8786	High Similarity	NPC55832
0.8786	High Similarity	NPC268204
0.8786	High Similarity	NPC52789
0.8779	High Similarity	NPC10926
0.8777	High Similarity	NPC283429
0.8777	High Similarity	NPC295384
0.8777	High Similarity	NPC275903
0.8777	High Similarity	NPC477956
0.8768	High Similarity	NPC317119
0.8768	High Similarity	NPC153979
0.8768	High Similarity	NPC472419
0.8767	High Similarity	NPC293286
0.8759	High Similarity	NPC278476
0.8759	High Similarity	NPC254412
0.8759	High Similarity	NPC156092
0.8759	High Similarity	NPC13575
0.8759	High Similarity	NPC262038
0.8759	High Similarity	NPC84699
0.8759	High Similarity	NPC319910
0.8759	High Similarity	NPC262039
0.875	High Similarity	NPC89442
0.875	High Similarity	NPC470461
0.875	High Similarity	NPC159525
0.875	High Similarity	NPC475088
0.8732	High Similarity	NPC216538
0.8732	High Similarity	NPC470890
0.8732	High Similarity	NPC273538
0.8732	High Similarity	NPC87486
0.8732	High Similarity	NPC224714
0.8732	High Similarity	NPC124780
0.8731	High Similarity	NPC259942
0.8731	High Similarity	NPC147757
0.8714	High Similarity	NPC253822
0.8714	High Similarity	NPC11056
0.8714	High Similarity	NPC101366
0.8705	High Similarity	NPC138099
0.8705	High Similarity	NPC242994
0.8705	High Similarity	NPC471620
0.8705	High Similarity	NPC190457
0.8699	High Similarity	NPC217149
0.8699	High Similarity	NPC138288
0.8699	High Similarity	NPC216035
0.8696	High Similarity	NPC213603
0.869	High Similarity	NPC105136
0.8686	High Similarity	NPC103842
0.8686	High Similarity	NPC164136
0.8686	High Similarity	NPC286336
0.8682	High Similarity	NPC229649
0.8682	High Similarity	NPC146642
0.8681	High Similarity	NPC470460
0.8681	High Similarity	NPC168085
0.8672	High Similarity	NPC473767
0.8672	High Similarity	NPC188814
0.8672	High Similarity	NPC158222
0.8672	High Similarity	NPC195262
0.8672	High Similarity	NPC161617
0.8671	High Similarity	NPC306488
0.8671	High Similarity	NPC470458
0.8671	High Similarity	NPC178343
0.8671	High Similarity	NPC124729
0.8671	High Similarity	NPC5820
0.8667	High Similarity	NPC198249
0.8662	High Similarity	NPC164980
0.8662	High Similarity	NPC68104
0.8662	High Similarity	NPC310130
0.8662	High Similarity	NPC175504
0.8662	High Similarity	NPC91560
0.8662	High Similarity	NPC212932
0.8662	High Similarity	NPC24821
0.8662	High Similarity	NPC75049
0.8662	High Similarity	NPC257097
0.8662	High Similarity	NPC150408
0.8662	High Similarity	NPC9117
0.8662	High Similarity	NPC39329
0.8662	High Similarity	NPC169591
0.8662	High Similarity	NPC190637
0.8662	High Similarity	NPC221432

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 NPC70859 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	892
0.2-0.3	1488
0.3-0.4	2715
0.4-0.5	2174
0.5-0.6	1107
0.6-0.7	367
0.7-0.8	117
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8732	High Similarity	NPD4378	Clinical (unspecified phase)
0.8562	High Similarity	NPD4380	Phase 2
0.8489	Intermediate Similarity	NPD1510	Phase 2
0.8489	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1240	Approved
0.8467	Intermediate Similarity	NPD943	Approved
0.8345	Intermediate Similarity	NPD1607	Approved
0.8344	Intermediate Similarity	NPD7075	Discontinued
0.831	Intermediate Similarity	NPD1549	Phase 2
0.8276	Intermediate Similarity	NPD7390	Discontinued
0.8267	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD6801	Discontinued
0.8169	Intermediate Similarity	NPD2796	Approved
0.8099	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD2935	Discontinued
0.8027	Intermediate Similarity	NPD6799	Approved
0.8013	Intermediate Similarity	NPD7411	Suspended
0.7987	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1934	Approved
0.7956	Intermediate Similarity	NPD1164	Approved
0.7922	Intermediate Similarity	NPD3882	Suspended
0.7911	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6166	Phase 2
0.7908	Intermediate Similarity	NPD7819	Suspended
0.7829	Intermediate Similarity	NPD6599	Discontinued
0.7826	Intermediate Similarity	NPD1470	Approved
0.78	Intermediate Similarity	NPD1512	Approved
0.7794	Intermediate Similarity	NPD1201	Approved
0.7793	Intermediate Similarity	NPD5406	Approved
0.7793	Intermediate Similarity	NPD5405	Approved
0.7793	Intermediate Similarity	NPD5408	Approved
0.7793	Intermediate Similarity	NPD5404	Approved
0.7722	Intermediate Similarity	NPD6959	Discontinued
0.7708	Intermediate Similarity	NPD6651	Approved
0.7704	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7768	Phase 2
0.7688	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2801	Approved
0.7667	Intermediate Similarity	NPD1511	Approved
0.7635	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD2800	Approved
0.7632	Intermediate Similarity	NPD5403	Approved
0.7628	Intermediate Similarity	NPD3817	Phase 2
0.7616	Intermediate Similarity	NPD2534	Approved
0.7616	Intermediate Similarity	NPD2532	Approved
0.7616	Intermediate Similarity	NPD2533	Approved
0.7593	Intermediate Similarity	NPD3818	Discontinued
0.7568	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6232	Discontinued
0.7561	Intermediate Similarity	NPD6797	Phase 2
0.7551	Intermediate Similarity	NPD1551	Phase 2
0.7547	Intermediate Similarity	NPD5494	Approved
0.7531	Intermediate Similarity	NPD7473	Discontinued
0.7516	Intermediate Similarity	NPD5402	Approved
0.7516	Intermediate Similarity	NPD920	Approved
0.7515	Intermediate Similarity	NPD7251	Discontinued
0.7515	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD1237	Approved
0.7483	Intermediate Similarity	NPD2799	Discontinued
0.7481	Intermediate Similarity	NPD9493	Approved
0.747	Intermediate Similarity	NPD7808	Phase 3
0.7467	Intermediate Similarity	NPD3750	Approved
0.7455	Intermediate Similarity	NPD5953	Discontinued
0.7439	Intermediate Similarity	NPD7286	Phase 2
0.7439	Intermediate Similarity	NPD7054	Approved
0.7431	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD74	Approved
0.7405	Intermediate Similarity	NPD9266	Approved
0.74	Intermediate Similarity	NPD1243	Approved
0.7397	Intermediate Similarity	NPD230	Phase 1
0.7394	Intermediate Similarity	NPD7472	Approved
0.7386	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2344	Approved
0.7372	Intermediate Similarity	NPD9545	Approved
0.7368	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD9269	Phase 2
0.7353	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4628	Phase 3
0.7351	Intermediate Similarity	NPD3400	Discontinued
0.7344	Intermediate Similarity	NPD940	Approved
0.7344	Intermediate Similarity	NPD846	Approved
0.7333	Intermediate Similarity	NPD5844	Phase 1
0.7328	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD9264	Approved
0.7328	Intermediate Similarity	NPD9263	Approved
0.7328	Intermediate Similarity	NPD9267	Approved
0.7319	Intermediate Similarity	NPD9268	Approved
0.7312	Intermediate Similarity	NPD3749	Approved
0.731	Intermediate Similarity	NPD2313	Discontinued
0.7303	Intermediate Similarity	NPD6190	Approved
0.7284	Intermediate Similarity	NPD1247	Approved
0.7273	Intermediate Similarity	NPD2798	Approved
0.7267	Intermediate Similarity	NPD919	Approved
0.7255	Intermediate Similarity	NPD3300	Phase 2
0.7246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1203	Approved
0.7193	Intermediate Similarity	NPD8150	Discontinued
0.719	Intermediate Similarity	NPD2309	Approved
0.7172	Intermediate Similarity	NPD6832	Phase 2
0.7163	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD4363	Phase 3
0.7133	Intermediate Similarity	NPD3748	Approved
0.7126	Intermediate Similarity	NPD6020	Phase 2
0.7113	Intermediate Similarity	NPD3972	Approved
0.7091	Intermediate Similarity	NPD3926	Phase 2
0.7089	Intermediate Similarity	NPD3226	Approved
0.7089	Intermediate Similarity	NPD7458	Discontinued
0.708	Intermediate Similarity	NPD9281	Approved
0.7075	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD2654	Approved
0.7045	Intermediate Similarity	NPD6535	Approved
0.7045	Intermediate Similarity	NPD6534	Approved
0.7039	Intermediate Similarity	NPD2346	Discontinued
0.7034	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5710	Approved
0.703	Intermediate Similarity	NPD5711	Approved
0.7023	Intermediate Similarity	NPD9261	Approved
0.702	Intermediate Similarity	NPD7033	Discontinued
0.7007	Intermediate Similarity	NPD3027	Phase 3
0.7	Intermediate Similarity	NPD1242	Phase 1
0.6993	Remote Similarity	NPD9717	Approved
0.6963	Remote Similarity	NPD4750	Phase 3
0.6962	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD2859	Approved
0.6953	Remote Similarity	NPD2860	Approved
0.6944	Remote Similarity	NPD6778	Approved
0.6944	Remote Similarity	NPD6780	Approved
0.6944	Remote Similarity	NPD6777	Approved
0.6944	Remote Similarity	NPD6779	Approved
0.6944	Remote Similarity	NPD6776	Approved
0.6944	Remote Similarity	NPD6782	Approved
0.6944	Remote Similarity	NPD6781	Approved
0.6939	Remote Similarity	NPD4908	Phase 1
0.6933	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7699	Phase 2
0.6927	Remote Similarity	NPD7700	Phase 2
0.6923	Remote Similarity	NPD3020	Approved
0.6917	Remote Similarity	NPD5048	Discontinued
0.6913	Remote Similarity	NPD520	Approved
0.691	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4361	Phase 2
0.6908	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7003	Approved
0.6901	Remote Similarity	NPD3019	Approved
0.6901	Remote Similarity	NPD2932	Approved
0.6894	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1729	Discontinued
0.6875	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2934	Approved
0.6875	Remote Similarity	NPD2933	Approved
0.6864	Remote Similarity	NPD3751	Discontinued
0.6863	Remote Similarity	NPD6099	Approved
0.6863	Remote Similarity	NPD6100	Approved
0.6846	Remote Similarity	NPD3268	Approved
0.6846	Remote Similarity	NPD6798	Discontinued
0.6831	Remote Similarity	NPD7696	Phase 3
0.6831	Remote Similarity	NPD7435	Discontinued
0.6831	Remote Similarity	NPD7697	Approved
0.6831	Remote Similarity	NPD7698	Approved
0.6821	Remote Similarity	NPD5124	Phase 1
0.6821	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6355	Discontinued
0.6818	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1471	Phase 3
0.6811	Remote Similarity	NPD7584	Approved
0.6806	Remote Similarity	NPD1610	Phase 2
0.68	Remote Similarity	NPD6407	Approved
0.68	Remote Similarity	NPD6405	Approved
0.68	Remote Similarity	NPD8434	Phase 2
0.6797	Remote Similarity	NPD4308	Phase 3
0.6795	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7870	Phase 2
0.6793	Remote Similarity	NPD8320	Phase 1
0.6793	Remote Similarity	NPD8319	Approved
0.6793	Remote Similarity	NPD7871	Phase 2
0.6781	Remote Similarity	NPD1876	Approved
0.6774	Remote Similarity	NPD2424	Discontinued
0.6767	Remote Similarity	NPD1929	Approved
0.6767	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1930	Approved
0.6765	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD36	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