NPASS Compound

Structure

NPC474110 OpenBabel07101718202D 38 41 0 0 0 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 6.0622 -1.5000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 3.4641 1.0000 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 1.7321 0.0000 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 -1.7321 -2.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 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 0.8660 -1.5000 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 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 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 1 17 2 0 0 0 0 2 7 2 0 0 0 0 2 17 1 0 0 0 0 3 10 1 0 0 0 0 3 17 1 0 0 0 0 4 11 1 0 0 0 0 4 18 1 0 0 0 0 5 12 2 0 0 0 0 5 18 1 0 0 0 0 6 19 2 0 0 0 0 7 19 1 0 0 0 0 8 9 2 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 27 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 20 2 0 0 0 0 14 28 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 29 2 0 0 0 0 16 30 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 25 1 0 0 0 0 21 28 2 0 0 0 0 22 23 1 0 0 0 0 22 26 2 0 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 24 30 2 0 0 0 0 25 33 2 0 0 0 0 26 34 1 0 0 0 0 27 35 2 0 0 0 0 28 36 1 0 0 0 0 29 37 1 0 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.16
Volume:	526.622
LogP:	5.522
LogD:	3.649
LogS:	-4.627
# Rotatable Bonds:	9
TPSA:	155.52
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	2.712
Fsp3:	0.133
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.446
MDCK Permeability:	7.712812475801911e-06
Pgp-inhibitor:	0.129
Pgp-substrate:	0.057
Human Intestinal Absorption (HIA):	0.967
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	98.2752914428711%
Volume Distribution (VD):	0.378
Pgp-substrate:	1.1249245405197144%

ADMET: Metabolism

CYP1A2-inhibitor:	0.877
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.93
CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.893
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.658
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.655
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	12.853
Half-life (T1/2):	0.86

ADMET: Toxicity

hERG Blockers:	0.129
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.653
AMES Toxicity:	0.639
Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.492
Skin Sensitization:	0.946
Carcinogencity:	0.163
Eye Corrosion:	0.003
Eye Irritation:	0.906
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC474110

Natural Product ID:	NPC474110
*Common Name:**	Rhuschalcone V
IUPAC Name:	1-[5-[5-[3-(2,4-dihydroxyphenyl)-3-oxopropyl]-2-hydroxyphenyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
Synonyms:	rhuschalcone V
Standard InCHIKey:	HMJSJJJZMSTJLO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H26O8/c31-19-6-1-17(2-7-19)3-10-27(35)24-15-23(29(37)16-30(24)38)22-13-18(5-12-26(22)34)4-11-25(33)21-9-8-20(32)14-28(21)36/h1-2,5-9,12-16,31-32,34,36-38H,3-4,10-11H2
SMILES:	C1=CC(=CC=C1CCC(=O)C2=C(C=C(C(=C2)C3=C(C=CC(=C3)CCC(=O)C4=C(C=C(C=C4)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462034
PubChem CID:	44566750
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
NPO32638	rhus pyroides	Species	Anacardiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[12762790]

☑ 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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	ED50	=	25.0	ug ml-1	PMID[523402]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	25.0	ug ml-1	PMID[523402]

☑ 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 NPC474110 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	415
0.1-0.2	1726
0.2-0.3	4019
0.3-0.4	11402
0.4-0.5	7625
0.5-0.6	5187
0.6-0.7	6111
0.7-0.8	5119
0.8-0.85	892
0.85-0.9	163
0.9-0.95	35
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC44960
0.9209	High Similarity	NPC227841
0.9149	High Similarity	NPC37709
0.9091	High Similarity	NPC474998
0.9084	High Similarity	NPC100067
0.9084	High Similarity	NPC169250
0.9084	High Similarity	NPC190043
0.9084	High Similarity	NPC98254
0.9084	High Similarity	NPC105157
0.9084	High Similarity	NPC23126
0.9084	High Similarity	NPC72158
0.9084	High Similarity	NPC162612
0.9084	High Similarity	NPC30501
0.9084	High Similarity	NPC103356
0.9084	High Similarity	NPC266689
0.9078	High Similarity	NPC85393
0.9078	High Similarity	NPC271944
0.9078	High Similarity	NPC110882
0.9071	High Similarity	NPC10764
0.9015	High Similarity	NPC221777
0.9015	High Similarity	NPC21305
0.9015	High Similarity	NPC473017
0.9014	High Similarity	NPC290194
0.9008	High Similarity	NPC267846
0.9008	High Similarity	NPC62952
0.9	High Similarity	NPC293545
0.9	High Similarity	NPC474203
0.9	High Similarity	NPC295712
0.9	High Similarity	NPC296752
0.9	High Similarity	NPC313047
0.9	High Similarity	NPC451542
0.9	High Similarity	NPC174905
0.8993	High Similarity	NPC246638
0.8963	High Similarity	NPC40524
0.8963	High Similarity	NPC139074
0.8963	High Similarity	NPC213485
0.8939	High Similarity	NPC116513
0.8913	High Similarity	NPC473622
0.8897	High Similarity	NPC67322
0.8897	High Similarity	NPC282780
0.8897	High Similarity	NPC35
0.8897	High Similarity	NPC138299
0.8897	High Similarity	NPC166480
0.8897	High Similarity	NPC222713
0.8897	High Similarity	NPC111112
0.8889	High Similarity	NPC175738
0.8849	High Similarity	NPC138099
0.8849	High Similarity	NPC242994
0.8846	High Similarity	NPC32032
0.8846	High Similarity	NPC133909
0.8832	High Similarity	NPC283590
0.8832	High Similarity	NPC70859
0.8832	High Similarity	NPC61153
0.8832	High Similarity	NPC130899
0.8819	High Similarity	NPC152233
0.8815	High Similarity	NPC475042
0.8794	High Similarity	NPC19631
0.8794	High Similarity	NPC257644
0.8794	High Similarity	NPC26238
0.8794	High Similarity	NPC239136
0.8786	High Similarity	NPC169452
0.8786	High Similarity	NPC181560
0.8786	High Similarity	NPC275903
0.8777	High Similarity	NPC20210
0.8776	High Similarity	NPC303485
0.8776	High Similarity	NPC290830
0.8776	High Similarity	NPC71061
0.8776	High Similarity	NPC194593
0.8776	High Similarity	NPC72425
0.8769	High Similarity	NPC19174
0.8769	High Similarity	NPC224273
0.8769	High Similarity	NPC115159
0.8769	High Similarity	NPC143427
0.8769	High Similarity	NPC45438
0.8769	High Similarity	NPC196976
0.8769	High Similarity	NPC242895
0.8769	High Similarity	NPC267552
0.8769	High Similarity	NPC73532
0.8769	High Similarity	NPC156139
0.8768	High Similarity	NPC191976
0.8759	High Similarity	NPC44437
0.8759	High Similarity	NPC477221
0.8759	High Similarity	NPC475088
0.875	High Similarity	NPC261271
0.875	High Similarity	NPC475348
0.8741	High Similarity	NPC282957
0.8741	High Similarity	NPC12402
0.8741	High Similarity	NPC194949
0.8732	High Similarity	NPC471682
0.8722	High Similarity	NPC8745
0.8716	High Similarity	NPC52611
0.8716	High Similarity	NPC14606
0.8716	High Similarity	NPC186227
0.8716	High Similarity	NPC182555
0.8716	High Similarity	NPC159707
0.8716	High Similarity	NPC265624
0.8716	High Similarity	NPC248739
0.8716	High Similarity	NPC121649
0.8716	High Similarity	NPC134171
0.8716	High Similarity	NPC205026
0.8716	High Similarity	NPC100049
0.8716	High Similarity	NPC150908
0.8716	High Similarity	NPC66441
0.8716	High Similarity	NPC300668
0.8716	High Similarity	NPC215203
0.8716	High Similarity	NPC158027
0.8714	High Similarity	NPC112789
0.8714	High Similarity	NPC19622
0.8712	High Similarity	NPC13238
0.8707	High Similarity	NPC43345
0.8705	High Similarity	NPC62272
0.8705	High Similarity	NPC53206
0.8705	High Similarity	NPC471905
0.8705	High Similarity	NPC53414
0.8702	High Similarity	NPC91105
0.8702	High Similarity	NPC309765
0.8692	High Similarity	NPC297186
0.8686	High Similarity	NPC267205
0.8667	High Similarity	NPC92624
0.8667	High Similarity	NPC476119
0.8662	High Similarity	NPC137649
0.8662	High Similarity	NPC193555
0.8649	High Similarity	NPC324447
0.8647	High Similarity	NPC10926
0.8647	High Similarity	NPC475733
0.8639	High Similarity	NPC476551
0.8639	High Similarity	NPC476552
0.8639	High Similarity	NPC476553
0.8636	High Similarity	NPC65761
0.8636	High Similarity	NPC472029
0.8633	High Similarity	NPC264112
0.8633	High Similarity	NPC194764
0.8633	High Similarity	NPC65005
0.8633	High Similarity	NPC254847
0.863	High Similarity	NPC288840
0.863	High Similarity	NPC291746
0.8626	High Similarity	NPC303737
0.8626	High Similarity	NPC215392
0.8615	High Similarity	NPC159525
0.8611	High Similarity	NPC471473
0.8611	High Similarity	NPC471524
0.8611	High Similarity	NPC471683
0.8611	High Similarity	NPC471523
0.8603	High Similarity	NPC259942
0.8591	High Similarity	NPC66508
0.8591	High Similarity	NPC226656
0.8591	High Similarity	NPC79375
0.8591	High Similarity	NPC254351
0.8591	High Similarity	NPC37253
0.8582	High Similarity	NPC251681
0.8582	High Similarity	NPC190457
0.8582	High Similarity	NPC143438
0.8582	High Similarity	NPC243528
0.8561	High Similarity	NPC470210
0.8552	High Similarity	NPC25844
0.855	High Similarity	NPC229649
0.855	High Similarity	NPC149246
0.8543	High Similarity	NPC51760
0.8543	High Similarity	NPC324736
0.854	High Similarity	NPC275504
0.854	High Similarity	NPC474517
0.854	High Similarity	NPC72669
0.8538	High Similarity	NPC188814
0.8538	High Similarity	NPC195262
0.8538	High Similarity	NPC158222
0.8533	High Similarity	NPC69531
0.8533	High Similarity	NPC54830
0.8533	High Similarity	NPC32867
0.8533	High Similarity	NPC56049
0.8531	High Similarity	NPC135524
0.8531	High Similarity	NPC469404
0.8531	High Similarity	NPC474961
0.8531	High Similarity	NPC14871
0.8529	High Similarity	NPC102829
0.8529	High Similarity	NPC120488
0.8529	High Similarity	NPC109123
0.85	High Similarity	NPC118919
0.85	High Similarity	NPC131039
0.8487	Intermediate Similarity	NPC472052
0.8487	Intermediate Similarity	NPC472060
0.8487	Intermediate Similarity	NPC470342
0.8483	Intermediate Similarity	NPC278175
0.8483	Intermediate Similarity	NPC257236
0.8477	Intermediate Similarity	NPC208258
0.8477	Intermediate Similarity	NPC475184
0.8467	Intermediate Similarity	NPC66029
0.8462	Intermediate Similarity	NPC215311
0.8462	Intermediate Similarity	NPC219917
0.8462	Intermediate Similarity	NPC259166
0.8462	Intermediate Similarity	NPC204985
0.8462	Intermediate Similarity	NPC305845
0.8462	Intermediate Similarity	NPC48624
0.8462	Intermediate Similarity	NPC11056
0.8462	Intermediate Similarity	NPC204045
0.8462	Intermediate Similarity	NPC213659
0.8462	Intermediate Similarity	NPC290550
0.8462	Intermediate Similarity	NPC144118
0.8462	Intermediate Similarity	NPC80962
0.8462	Intermediate Similarity	NPC326109
0.8462	Intermediate Similarity	NPC172250

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 NPC474110 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	965
0.2-0.3	1439
0.3-0.4	2894
0.4-0.5	2098
0.5-0.6	973
0.6-0.7	285
0.7-0.8	101
0.8-0.85	13
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9209	High Similarity	NPD7390	Discontinued
0.8705	High Similarity	NPD5405	Approved
0.8705	High Similarity	NPD5406	Approved
0.8705	High Similarity	NPD5408	Approved
0.8705	High Similarity	NPD5404	Approved
0.8633	High Similarity	NPD1509	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD943	Approved
0.8322	Intermediate Similarity	NPD4380	Phase 2
0.8269	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1510	Phase 2
0.8231	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6959	Discontinued
0.817	Intermediate Similarity	NPD7768	Phase 2
0.8146	Intermediate Similarity	NPD7411	Suspended
0.8102	Intermediate Similarity	NPD1164	Approved
0.8102	Intermediate Similarity	NPD1470	Approved
0.8085	Intermediate Similarity	NPD1240	Approved
0.8074	Intermediate Similarity	NPD1201	Approved
0.8	Intermediate Similarity	NPD3749	Approved
0.7987	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1607	Approved
0.7945	Intermediate Similarity	NPD1549	Phase 2
0.7911	Intermediate Similarity	NPD6232	Discontinued
0.7877	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7473	Discontinued
0.7862	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7819	Suspended
0.7806	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7718	Intermediate Similarity	NPD3750	Approved
0.7687	Intermediate Similarity	NPD2935	Discontinued
0.7687	Intermediate Similarity	NPD2796	Approved
0.7682	Intermediate Similarity	NPD1511	Approved
0.7593	Intermediate Similarity	NPD6166	Phase 2
0.7593	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1512	Approved
0.758	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2800	Approved
0.7533	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2344	Approved
0.7516	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD1934	Approved
0.7484	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6651	Approved
0.7468	Intermediate Similarity	NPD2801	Approved
0.7455	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3764	Approved
0.7383	Intermediate Similarity	NPD3748	Approved
0.7383	Intermediate Similarity	NPD2799	Discontinued
0.7372	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7003	Approved
0.7351	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5844	Phase 1
0.7346	Intermediate Similarity	NPD5494	Approved
0.7338	Intermediate Similarity	NPD6799	Approved
0.7329	Intermediate Similarity	NPD2313	Discontinued
0.7325	Intermediate Similarity	NPD3226	Approved
0.7321	Intermediate Similarity	NPD6559	Discontinued
0.732	Intermediate Similarity	NPD2309	Approved
0.7303	Intermediate Similarity	NPD1243	Approved
0.7293	Intermediate Similarity	NPD9266	Approved
0.7293	Intermediate Similarity	NPD74	Approved
0.7292	Intermediate Similarity	NPD2798	Approved
0.729	Intermediate Similarity	NPD2534	Approved
0.729	Intermediate Similarity	NPD2532	Approved
0.729	Intermediate Similarity	NPD2533	Approved
0.7289	Intermediate Similarity	NPD3818	Discontinued
0.7278	Intermediate Similarity	NPD6599	Discontinued
0.7273	Intermediate Similarity	NPD3300	Phase 2
0.7267	Intermediate Similarity	NPD3882	Suspended
0.7262	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD9269	Phase 2
0.7219	Intermediate Similarity	NPD1551	Phase 2
0.7218	Intermediate Similarity	NPD9264	Approved
0.7218	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9267	Approved
0.7218	Intermediate Similarity	NPD9263	Approved
0.7215	Intermediate Similarity	NPD7458	Discontinued
0.7214	Intermediate Similarity	NPD9268	Approved
0.7211	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3817	Phase 2
0.7202	Intermediate Similarity	NPD7074	Phase 3
0.7197	Intermediate Similarity	NPD5403	Approved
0.7197	Intermediate Similarity	NPD920	Approved
0.7179	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD6020	Phase 2
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD3400	Discontinued
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD9493	Approved
0.7103	Intermediate Similarity	NPD1203	Approved
0.7101	Intermediate Similarity	NPD7472	Approved
0.7099	Intermediate Similarity	NPD846	Approved
0.7099	Intermediate Similarity	NPD940	Approved
0.7099	Intermediate Similarity	NPD5402	Approved
0.7089	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4908	Phase 1
0.707	Intermediate Similarity	NPD5401	Approved
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.7059	Intermediate Similarity	NPD6797	Phase 2
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3019	Approved
0.7041	Intermediate Similarity	NPD7286	Phase 2
0.7039	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8312	Approved
0.7035	Intermediate Similarity	NPD8313	Approved
0.7029	Intermediate Similarity	NPD4287	Approved
0.7018	Intermediate Similarity	NPD7251	Discontinued
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD9281	Approved
0.6977	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7808	Phase 3
0.6954	Remote Similarity	NPD230	Phase 1
0.6933	Remote Similarity	NPD8455	Phase 2
0.6923	Remote Similarity	NPD2932	Approved
0.6917	Remote Similarity	NPD9261	Approved
0.6914	Remote Similarity	NPD8150	Discontinued
0.6901	Remote Similarity	NPD9545	Approved
0.6897	Remote Similarity	NPD3972	Approved
0.6894	Remote Similarity	NPD1242	Phase 1
0.6889	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6100	Approved
0.6883	Remote Similarity	NPD6099	Approved
0.6879	Remote Similarity	NPD6190	Approved
0.6872	Remote Similarity	NPD6535	Approved
0.6872	Remote Similarity	NPD4363	Phase 3
0.6872	Remote Similarity	NPD4360	Phase 2
0.6872	Remote Similarity	NPD6534	Approved
0.6867	Remote Similarity	NPD3268	Approved
0.6861	Remote Similarity	NPD4750	Phase 3
0.6857	Remote Similarity	NPD5951	Approved
0.6855	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6832	Phase 2
0.6845	Remote Similarity	NPD8151	Discontinued
0.6838	Remote Similarity	NPD2342	Discontinued
0.6828	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3020	Approved
0.6815	Remote Similarity	NPD4628	Phase 3
0.6815	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4288	Approved
0.6788	Remote Similarity	NPD2296	Approved
0.6786	Remote Similarity	NPD1247	Approved
0.6784	Remote Similarity	NPD7177	Discontinued
0.6781	Remote Similarity	NPD9717	Approved
0.6776	Remote Similarity	NPD6782	Approved
0.6776	Remote Similarity	NPD6776	Approved
0.6776	Remote Similarity	NPD6779	Approved
0.6776	Remote Similarity	NPD6778	Approved
0.6776	Remote Similarity	NPD6777	Approved
0.6776	Remote Similarity	NPD6780	Approved
0.6776	Remote Similarity	NPD6781	Approved
0.6766	Remote Similarity	NPD919	Approved
0.6758	Remote Similarity	NPD7700	Phase 2
0.6758	Remote Similarity	NPD7699	Phase 2
0.6757	Remote Similarity	NPD2797	Approved
0.6752	Remote Similarity	NPD2654	Approved
0.6746	Remote Similarity	NPD5710	Approved
0.6746	Remote Similarity	NPD7229	Phase 3
0.6746	Remote Similarity	NPD5711	Approved
0.6731	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7870	Phase 2
0.672	Remote Similarity	NPD7871	Phase 2
0.6718	Remote Similarity	NPD2859	Approved
0.6718	Remote Similarity	NPD2860	Approved
0.6712	Remote Similarity	NPD1610	Phase 2
0.671	Remote Similarity	NPD4308	Phase 3
0.6709	Remote Similarity	NPD8166	Discontinued
0.6689	Remote Similarity	NPD7008	Discontinued
0.6689	Remote Similarity	NPD4625	Phase 3
0.6686	Remote Similarity	NPD3751	Discontinued
0.6685	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1930	Approved
0.6667	Remote Similarity	NPD1929	Approved
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD7698	Approved
0.6648	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4361	Phase 2
0.6647	Remote Similarity	NPD3787	Discontinued
0.6644	Remote Similarity	NPD3023	Approved
0.6644	Remote Similarity	NPD3026	Approved
0.6641	Remote Similarity	NPD2934	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