NPASS Compound

Structure

NPC181388 OpenBabel07101718232D 35 37 0 0 0 0 0 0 0 0999 V2000 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 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 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 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 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 -2.5000 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 0.0000 -4.0000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 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 -5.5000 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 0.0000 -3.0000 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 -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 0.8660 -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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -1.7321 -0.0000 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 1.7321 -3.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 18 2 0 0 0 0 11 20 1 0 0 0 0 12 21 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 24 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 21 23 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 24 27 1 0 0 0 0 24 31 2 0 0 0 0 25 32 2 0 0 0 0 25 35 1 0 0 0 0 26 28 1 0 0 0 0 26 30 2 0 0 0 0 27 29 2 0 0 0 0 27 30 1 0 0 0 0 28 33 1 0 0 0 0 29 34 1 0 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.24
Volume:	516.717
LogP:	7.297
LogD:	4.6
LogS:	-3.948
# Rotatable Bonds:	9
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.192
Synthetic Accessibility Score:	3.03
Fsp3:	0.333
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:	-4.815
MDCK Permeability:	1.9331640942255035e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.081

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	99.51115417480469%
Volume Distribution (VD):	0.326
Pgp-substrate:	1.202789068222046%

ADMET: Metabolism

CYP1A2-inhibitor:	0.215
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.868
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.86
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	6.506
Half-life (T1/2):	0.094

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.9
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.762
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.068
Respiratory Toxicity:	0.334

Download Data

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

Natural Product: NPC181388

Natural Product ID:	NPC181388
*Common Name:**	6-[(2E)-3,7-Dimethylocta-2,6-Dienyl]-5,7-Dihydroxy-8-(3-Methylbutanoyl)-4-Phenylchromen-2-One
IUPAC Name:	6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-8-(3-methylbutanoyl)-4-phenylchromen-2-one
Synonyms:
Standard InCHIKey:	DDEGGXJLPSRCOB-XSFVSMFZSA-N
Standard InCHI:	InChI=1S/C30H34O5/c1-18(2)10-9-11-20(5)14-15-22-28(33)26-23(21-12-7-6-8-13-21)17-25(32)35-30(26)27(29(22)34)24(31)16-19(3)4/h6-8,10,12-14,17,19,33-34H,9,11,15-16H2,1-5H3/b20-14+
SMILES:	C/C(=CCc1c(O)c(C(=O)CC(C)C)c2c(c1O)c(cc(=O)o2)c1ccccc1)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1277773
PubChem CID:	23250952
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO4756	Mesua elegans	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20943395]
NPO4756	Mesua elegans	Species	Calophyllaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	>	20000.0	nM	PMID[540310]

☑ 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 NPC181388 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	380
0.1-0.2	1619
0.2-0.3	3863
0.3-0.4	9644
0.4-0.5	9034
0.5-0.6	3863
0.6-0.7	6000
0.7-0.8	4585
0.8-0.85	2155
0.85-0.9	1257
0.9-0.95	250
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC1886
0.9928	High Similarity	NPC178627
0.9928	High Similarity	NPC196137
0.9928	High Similarity	NPC469935
0.9857	High Similarity	NPC154217
0.9857	High Similarity	NPC470322
0.9856	High Similarity	NPC188632
0.9856	High Similarity	NPC94794
0.9856	High Similarity	NPC196459
0.9856	High Similarity	NPC470296
0.9856	High Similarity	NPC87609
0.9856	High Similarity	NPC112791
0.9789	High Similarity	NPC469932
0.9784	High Similarity	NPC36181
0.9718	High Similarity	NPC161864
0.9718	High Similarity	NPC469933
0.9718	High Similarity	NPC208303
0.9648	High Similarity	NPC297886
0.9648	High Similarity	NPC140120
0.9648	High Similarity	NPC249942
0.9583	High Similarity	NPC474735
0.9577	High Similarity	NPC57470
0.9568	High Similarity	NPC19476
0.9568	High Similarity	NPC473209
0.9568	High Similarity	NPC241975
0.9517	High Similarity	NPC290671
0.9514	High Similarity	NPC19238
0.951	High Similarity	NPC180477
0.9507	High Similarity	NPC469953
0.9496	High Similarity	NPC219584
0.9496	High Similarity	NPC470083
0.9496	High Similarity	NPC199458
0.9496	High Similarity	NPC183639
0.9456	High Similarity	NPC469934
0.9433	High Similarity	NPC470555
0.9433	High Similarity	NPC282300
0.9429	High Similarity	NPC220062
0.9429	High Similarity	NPC53181
0.9429	High Similarity	NPC55018
0.9429	High Similarity	NPC301217
0.9429	High Similarity	NPC303633
0.9429	High Similarity	NPC217186
0.9429	High Similarity	NPC216978
0.9429	High Similarity	NPC470986
0.9429	High Similarity	NPC96565
0.9424	High Similarity	NPC131782
0.9424	High Similarity	NPC474624
0.9424	High Similarity	NPC138047
0.9384	High Similarity	NPC209142
0.9384	High Similarity	NPC312549
0.9379	High Similarity	NPC104236
0.9379	High Similarity	NPC164205
0.9371	High Similarity	NPC326500
0.9362	High Similarity	NPC159275
0.9362	High Similarity	NPC221173
0.9362	High Similarity	NPC270883
0.9362	High Similarity	NPC261227
0.9362	High Similarity	NPC172986
0.9362	High Similarity	NPC241100
0.9357	High Similarity	NPC201395
0.9315	High Similarity	NPC151973
0.9301	High Similarity	NPC307895
0.9301	High Similarity	NPC11700
0.9301	High Similarity	NPC219915
0.9301	High Similarity	NPC212932
0.9301	High Similarity	NPC470553
0.9301	High Similarity	NPC24821
0.9301	High Similarity	NPC9117
0.9301	High Similarity	NPC293053
0.9301	High Similarity	NPC190637
0.9296	High Similarity	NPC110969
0.9296	High Similarity	NPC205006
0.9296	High Similarity	NPC156590
0.9296	High Similarity	NPC118840
0.9296	High Similarity	NPC64908
0.9296	High Similarity	NPC147688
0.9291	High Similarity	NPC472343
0.9291	High Similarity	NPC78913
0.9291	High Similarity	NPC18260
0.9262	High Similarity	NPC474609
0.9262	High Similarity	NPC78554
0.9262	High Similarity	NPC321372
0.9262	High Similarity	NPC469936
0.9262	High Similarity	NPC475797
0.9262	High Similarity	NPC109967
0.9262	High Similarity	NPC129053
0.9262	High Similarity	NPC474738
0.9236	High Similarity	NPC288910
0.9236	High Similarity	NPC118059
0.9236	High Similarity	NPC133060
0.9236	High Similarity	NPC235217
0.9236	High Similarity	NPC311741
0.9236	High Similarity	NPC473014
0.9236	High Similarity	NPC234629
0.9236	High Similarity	NPC271288
0.9236	High Similarity	NPC273538
0.9236	High Similarity	NPC470554
0.9236	High Similarity	NPC216538
0.9231	High Similarity	NPC299080
0.9231	High Similarity	NPC470556
0.9231	High Similarity	NPC293852
0.9231	High Similarity	NPC226636
0.9231	High Similarity	NPC144499
0.9231	High Similarity	NPC11561
0.9231	High Similarity	NPC266725
0.9231	High Similarity	NPC473042
0.9231	High Similarity	NPC217083
0.9231	High Similarity	NPC214236
0.9231	High Similarity	NPC78803
0.9231	High Similarity	NPC112829
0.9231	High Similarity	NPC62840
0.9231	High Similarity	NPC200694
0.9231	High Similarity	NPC59739
0.9225	High Similarity	NPC235239
0.9225	High Similarity	NPC150522
0.9225	High Similarity	NPC305355
0.9225	High Similarity	NPC69769
0.9225	High Similarity	NPC475680
0.922	High Similarity	NPC470668
0.922	High Similarity	NPC470669
0.9214	High Similarity	NPC13408
0.9195	High Similarity	NPC279218
0.9195	High Similarity	NPC108937
0.9178	High Similarity	NPC145467
0.9172	High Similarity	NPC127059
0.9172	High Similarity	NPC25844
0.9172	High Similarity	NPC470910
0.9172	High Similarity	NPC153758
0.9172	High Similarity	NPC476088
0.9172	High Similarity	NPC477955
0.9172	High Similarity	NPC5820
0.9172	High Similarity	NPC124729
0.9172	High Similarity	NPC220418
0.9172	High Similarity	NPC178343
0.9172	High Similarity	NPC306488
0.9172	High Similarity	NPC285630
0.9172	High Similarity	NPC474161
0.9167	High Similarity	NPC166138
0.9167	High Similarity	NPC18585
0.9167	High Similarity	NPC85162
0.9167	High Similarity	NPC38219
0.9167	High Similarity	NPC77794
0.9167	High Similarity	NPC474939
0.9167	High Similarity	NPC184738
0.9167	High Similarity	NPC106985
0.9167	High Similarity	NPC185276
0.9167	High Similarity	NPC33653
0.9167	High Similarity	NPC470909
0.9167	High Similarity	NPC278249
0.9167	High Similarity	NPC81697
0.9167	High Similarity	NPC107177
0.9167	High Similarity	NPC96216
0.9167	High Similarity	NPC125894
0.9167	High Similarity	NPC223812
0.9161	High Similarity	NPC103362
0.9161	High Similarity	NPC110038
0.9161	High Similarity	NPC248372
0.9161	High Similarity	NPC14871
0.9155	High Similarity	NPC283429
0.9155	High Similarity	NPC240305
0.9149	High Similarity	NPC228661
0.9149	High Similarity	NPC332594
0.9149	High Similarity	NPC103001
0.9122	High Similarity	NPC317715
0.9122	High Similarity	NPC316960
0.9122	High Similarity	NPC309512
0.9122	High Similarity	NPC78835
0.9122	High Similarity	NPC148945
0.9122	High Similarity	NPC204561
0.9116	High Similarity	NPC269420
0.9116	High Similarity	NPC470461
0.911	High Similarity	NPC296998
0.911	High Similarity	NPC177995
0.911	High Similarity	NPC308200
0.911	High Similarity	NPC97716
0.911	High Similarity	NPC237635
0.911	High Similarity	NPC474108
0.911	High Similarity	NPC24673
0.911	High Similarity	NPC14001
0.911	High Similarity	NPC79469
0.911	High Similarity	NPC166757
0.911	High Similarity	NPC283234
0.911	High Similarity	NPC473077
0.911	High Similarity	NPC201731
0.911	High Similarity	NPC104406
0.911	High Similarity	NPC285748
0.9103	High Similarity	NPC319752
0.9103	High Similarity	NPC197252
0.9103	High Similarity	NPC131568
0.9103	High Similarity	NPC257236
0.9103	High Similarity	NPC473015
0.9103	High Similarity	NPC473013
0.9103	High Similarity	NPC278175
0.9103	High Similarity	NPC206212
0.9103	High Similarity	NPC224714
0.9103	High Similarity	NPC236766
0.9103	High Similarity	NPC29577
0.9103	High Similarity	NPC131579
0.9103	High Similarity	NPC71184
0.9097	High Similarity	NPC148757

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 NPC181388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	964
0.2-0.3	1547
0.3-0.4	2564
0.4-0.5	2006
0.5-0.6	1169
0.6-0.7	364
0.7-0.8	122
0.8-0.85	39
0.85-0.9	19
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9236	High Similarity	NPD4378	Clinical (unspecified phase)
0.9103	High Similarity	NPD7410	Clinical (unspecified phase)
0.8947	High Similarity	NPD7075	Discontinued
0.8874	High Similarity	NPD7096	Clinical (unspecified phase)
0.8874	High Similarity	NPD7819	Suspended
0.8867	High Similarity	NPD7411	Suspended
0.8816	High Similarity	NPD8443	Clinical (unspecified phase)
0.875	High Similarity	NPD1550	Clinical (unspecified phase)
0.875	High Similarity	NPD1552	Clinical (unspecified phase)
0.8741	High Similarity	NPD1510	Phase 2
0.8699	High Similarity	NPD3750	Approved
0.869	High Similarity	NPD1549	Phase 2
0.8684	High Similarity	NPD6801	Discontinued
0.8681	High Similarity	NPD2796	Approved
0.8636	High Similarity	NPD7768	Phase 2
0.863	High Similarity	NPD1243	Approved
0.8627	High Similarity	NPD2393	Clinical (unspecified phase)
0.8592	High Similarity	NPD1240	Approved
0.8562	High Similarity	NPD970	Clinical (unspecified phase)
0.8553	High Similarity	NPD4380	Phase 2
0.8523	High Similarity	NPD1511	Approved
0.8523	High Similarity	NPD6799	Approved
0.8503	High Similarity	NPD7421	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD2799	Discontinued
0.8472	Intermediate Similarity	NPD1607	Approved
0.8462	Intermediate Similarity	NPD3749	Approved
0.8451	Intermediate Similarity	NPD2313	Discontinued
0.8451	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1512	Approved
0.8387	Intermediate Similarity	NPD2801	Approved
0.8378	Intermediate Similarity	NPD2800	Approved
0.8356	Intermediate Similarity	NPD3748	Approved
0.8355	Intermediate Similarity	NPD920	Approved
0.8345	Intermediate Similarity	NPD6651	Approved
0.8344	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8323	Intermediate Similarity	NPD1934	Approved
0.8322	Intermediate Similarity	NPD3268	Approved
0.8312	Intermediate Similarity	NPD6599	Discontinued
0.8299	Intermediate Similarity	NPD2935	Discontinued
0.8299	Intermediate Similarity	NPD1551	Phase 2
0.8227	Intermediate Similarity	NPD1203	Approved
0.8227	Intermediate Similarity	NPD2797	Approved
0.8224	Intermediate Similarity	NPD2534	Approved
0.8224	Intermediate Similarity	NPD2533	Approved
0.8224	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD2532	Approved
0.8137	Intermediate Similarity	NPD6232	Discontinued
0.8129	Intermediate Similarity	NPD3226	Approved
0.8121	Intermediate Similarity	NPD5953	Discontinued
0.8117	Intermediate Similarity	NPD5403	Approved
0.811	Intermediate Similarity	NPD7286	Phase 2
0.8079	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6959	Discontinued
0.8071	Intermediate Similarity	NPD422	Phase 1
0.8056	Intermediate Similarity	NPD6832	Phase 2
0.805	Intermediate Similarity	NPD3882	Suspended
0.8027	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD5124	Phase 1
0.8024	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD9717	Approved
0.8	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD2346	Discontinued
0.7987	Intermediate Similarity	NPD5401	Approved
0.7987	Intermediate Similarity	NPD4308	Phase 3
0.7972	Intermediate Similarity	NPD3267	Approved
0.7972	Intermediate Similarity	NPD3266	Approved
0.7952	Intermediate Similarity	NPD7472	Approved
0.7952	Intermediate Similarity	NPD7074	Phase 3
0.795	Intermediate Similarity	NPD919	Approved
0.7939	Intermediate Similarity	NPD3818	Discontinued
0.7937	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6100	Approved
0.7933	Intermediate Similarity	NPD6099	Approved
0.7927	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6166	Phase 2
0.7917	Intermediate Similarity	NPD2798	Approved
0.7902	Intermediate Similarity	NPD3225	Approved
0.7901	Intermediate Similarity	NPD5494	Approved
0.7892	Intermediate Similarity	NPD5844	Phase 1
0.7881	Intermediate Similarity	NPD2344	Approved
0.7875	Intermediate Similarity	NPD5402	Approved
0.7867	Intermediate Similarity	NPD7033	Discontinued
0.7857	Intermediate Similarity	NPD7251	Discontinued
0.7857	Intermediate Similarity	NPD6559	Discontinued
0.7843	Intermediate Similarity	NPD4628	Phase 3
0.7823	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7808	Phase 3
0.7799	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6797	Phase 2
0.7762	Intermediate Similarity	NPD1608	Approved
0.7748	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4307	Phase 2
0.7703	Intermediate Similarity	NPD1296	Phase 2
0.7702	Intermediate Similarity	NPD1465	Phase 2
0.7687	Intermediate Similarity	NPD4908	Phase 1
0.7684	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2309	Approved
0.7673	Intermediate Similarity	NPD7458	Discontinued
0.7654	Intermediate Similarity	NPD4288	Approved
0.76	Intermediate Similarity	NPD943	Approved
0.759	Intermediate Similarity	NPD5711	Approved
0.759	Intermediate Similarity	NPD5710	Approved
0.759	Intermediate Similarity	NPD7229	Phase 3
0.7584	Intermediate Similarity	NPD411	Approved
0.7582	Intermediate Similarity	NPD5404	Approved
0.7582	Intermediate Similarity	NPD5406	Approved
0.7582	Intermediate Similarity	NPD5405	Approved
0.7582	Intermediate Similarity	NPD5408	Approved
0.758	Intermediate Similarity	NPD7390	Discontinued
0.7571	Intermediate Similarity	NPD4363	Phase 3
0.7571	Intermediate Similarity	NPD4360	Phase 2
0.7569	Intermediate Similarity	NPD1610	Phase 2
0.7552	Intermediate Similarity	NPD17	Approved
0.755	Intermediate Similarity	NPD447	Suspended
0.755	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4287	Approved
0.7535	Intermediate Similarity	NPD1548	Phase 1
0.7532	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4361	Phase 2
0.7516	Intermediate Similarity	NPD6585	Discontinued
0.75	Intermediate Similarity	NPD7003	Approved
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1164	Approved
0.7469	Intermediate Similarity	NPD5889	Approved
0.7469	Intermediate Similarity	NPD5890	Approved
0.7467	Intermediate Similarity	NPD3764	Approved
0.7453	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1933	Approved
0.7434	Intermediate Similarity	NPD6355	Discontinued
0.7425	Intermediate Similarity	NPD1247	Approved
0.7413	Intermediate Similarity	NPD9545	Approved
0.74	Intermediate Similarity	NPD4625	Phase 3
0.7394	Intermediate Similarity	NPD9493	Approved
0.7375	Intermediate Similarity	NPD5049	Phase 3
0.736	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7351	Intermediate Similarity	NPD6798	Discontinued
0.7337	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2654	Approved
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.732	Intermediate Similarity	NPD230	Phase 1
0.7315	Intermediate Similarity	NPD1019	Discontinued
0.731	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6004	Phase 3
0.7308	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6002	Phase 3
0.7308	Intermediate Similarity	NPD6005	Phase 3
0.7308	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1481	Phase 2
0.7267	Intermediate Similarity	NPD6273	Approved
0.7255	Intermediate Similarity	NPD4060	Phase 1
0.7247	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4476	Approved
0.7244	Intermediate Similarity	NPD4477	Approved
0.7235	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5535	Approved
0.7233	Intermediate Similarity	NPD2354	Approved
0.7232	Intermediate Similarity	NPD8434	Phase 2
0.723	Intermediate Similarity	NPD4749	Approved
0.7225	Intermediate Similarity	NPD1729	Discontinued
0.7219	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7584	Approved
0.7215	Intermediate Similarity	NPD1652	Phase 2
0.7211	Intermediate Similarity	NPD1201	Approved
0.7211	Intermediate Similarity	NPD1535	Discovery
0.719	Intermediate Similarity	NPD8032	Phase 2
0.7188	Intermediate Similarity	NPD6666	Approved
0.7188	Intermediate Similarity	NPD6667	Approved
0.7181	Intermediate Similarity	NPD1283	Approved
0.7174	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1894	Discontinued
0.7169	Intermediate Similarity	NPD8455	Phase 2
0.7162	Intermediate Similarity	NPD3972	Approved
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6971	Discontinued
0.7133	Intermediate Similarity	NPD1470	Approved
0.7126	Intermediate Similarity	NPD2296	Approved
0.7124	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7177	Discontinued
0.7108	Intermediate Similarity	NPD37	Approved
0.7105	Intermediate Similarity	NPD2614	Approved
0.7101	Intermediate Similarity	NPD6234	Discontinued
0.7091	Intermediate Similarity	NPD6502	Phase 2
0.709	Intermediate Similarity	NPD7585	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