NPASS Compound

Structure

NPC203817 OpenBabel07101719522D 22 22 0 0 0 0 0 0 0 0999 V2000 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 9.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 7.5000 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 0.8660 4.5000 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 -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 1.7321 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 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 0.0000 2.0000 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 -0.0000 0.0000 C 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 22 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 14 18 1 0 0 0 0 14 19 2 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.17
Volume:	330.67
LogP:	5.021
LogD:	4.068
LogS:	-3.293
# Rotatable Bonds:	7
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.58
Synthetic Accessibility Score:	2.726
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.731
MDCK Permeability:	2.276018676639069e-05
Pgp-inhibitor:	0.481
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	99.32530975341797%
Volume Distribution (VD):	0.652
Pgp-substrate:	1.4711925983428955%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.424
CYP2C19-inhibitor:	0.944
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.94
CYP2D6-substrate:	0.668
CYP3A4-inhibitor:	0.608
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	10.367
Half-life (T1/2):	0.392

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.53
Drug-inuced Liver Injury (DILI):	0.237
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.316
Skin Sensitization:	0.887
Carcinogencity:	0.082
Eye Corrosion:	0.009
Eye Irritation:	0.957
Respiratory Toxicity:	0.88

Download Data

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

Natural Product: NPC203817

Natural Product ID:	NPC203817
*Common Name:**	2',6'-Dihydroxy-4'-Geranyloxyacetophenone
IUPAC Name:	1-[4-[(2E)-3,7-dimethylocta-2,6-dienoxy]-2,6-dihydroxyphenyl]ethanone
Synonyms:
Standard InCHIKey:	LBLRLPQWUQITCP-MDWZMJQESA-N
Standard InCHI:	InChI=1S/C18H24O4/c1-12(2)6-5-7-13(3)8-9-22-15-10-16(20)18(14(4)19)17(21)11-15/h6,8,10-11,20-21H,5,7,9H2,1-4H3/b13-8+
SMILES:	CC(=CCC/C(=C/COc1cc(c(C(=O)C)c(c1)O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401606
PubChem CID:	10859675
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575945]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163582]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20244	Melicope semecarpifolia	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	6
Others	2

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	34000.0	nM	PMID[551591]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	48000.0	nM	PMID[551591]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	40000.0	nM	PMID[551591]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	35000.0	nM	PMID[551591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29000.0	nM	PMID[551591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34000.0	nM	PMID[551591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	80.0	%	PMID[551591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	15.0	%	PMID[551591]

☑ 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 NPC203817 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	321
0.1-0.2	1499
0.2-0.3	4554
0.3-0.4	10885
0.4-0.5	7263
0.5-0.6	3989
0.6-0.7	5871
0.7-0.8	5359
0.8-0.85	1707
0.85-0.9	869
0.9-0.95	363
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9844	High Similarity	NPC144027
0.9844	High Similarity	NPC236974
0.9692	High Similarity	NPC470398
0.9692	High Similarity	NPC240147
0.9692	High Similarity	NPC156910
0.9692	High Similarity	NPC187826
0.9692	High Similarity	NPC470397
0.9692	High Similarity	NPC121243
0.9688	High Similarity	NPC10971
0.9618	High Similarity	NPC188879
0.9612	High Similarity	NPC223457
0.9609	High Similarity	NPC475589
0.9609	High Similarity	NPC31872
0.9609	High Similarity	NPC473584
0.9545	High Similarity	NPC470399
0.9545	High Similarity	NPC124269
0.9542	High Similarity	NPC240593
0.9542	High Similarity	NPC174999
0.9535	High Similarity	NPC25937
0.9531	High Similarity	NPC270369
0.9531	High Similarity	NPC5515
0.9524	High Similarity	NPC128428
0.9524	High Similarity	NPC305518
0.9474	High Similarity	NPC23257
0.9474	High Similarity	NPC140890
0.9474	High Similarity	NPC139554
0.9466	High Similarity	NPC60667
0.9403	High Similarity	NPC16455
0.9403	High Similarity	NPC284550
0.9403	High Similarity	NPC188243
0.9403	High Similarity	NPC471587
0.9403	High Similarity	NPC6407
0.9403	High Similarity	NPC307990
0.9403	High Similarity	NPC129853
0.9403	High Similarity	NPC110228
0.9403	High Similarity	NPC76445
0.9398	High Similarity	NPC131130
0.9398	High Similarity	NPC280284
0.9398	High Similarity	NPC188947
0.9398	High Similarity	NPC99333
0.9394	High Similarity	NPC13408
0.9394	High Similarity	NPC231772
0.9394	High Similarity	NPC127447
0.9394	High Similarity	NPC29353
0.9394	High Similarity	NPC124784
0.9394	High Similarity	NPC47815
0.9394	High Similarity	NPC234133
0.9394	High Similarity	NPC473887
0.9394	High Similarity	NPC194281
0.9389	High Similarity	NPC125920
0.9375	High Similarity	NPC69235
0.9375	High Similarity	NPC212379
0.9333	High Similarity	NPC258630
0.9333	High Similarity	NPC17170
0.9333	High Similarity	NPC156190
0.9333	High Similarity	NPC279650
0.9333	High Similarity	NPC166689
0.9333	High Similarity	NPC96408
0.9328	High Similarity	NPC265871
0.9328	High Similarity	NPC310135
0.9328	High Similarity	NPC150648
0.9328	High Similarity	NPC222342
0.9328	High Similarity	NPC225153
0.9328	High Similarity	NPC274784
0.9328	High Similarity	NPC329203
0.9328	High Similarity	NPC20709
0.9323	High Similarity	NPC266597
0.9323	High Similarity	NPC290291
0.9323	High Similarity	NPC275055
0.9323	High Similarity	NPC250266
0.9313	High Similarity	NPC18877
0.9313	High Similarity	NPC204960
0.9313	High Similarity	NPC192304
0.9313	High Similarity	NPC139813
0.9313	High Similarity	NPC20560
0.9313	High Similarity	NPC159623
0.9313	High Similarity	NPC56031
0.9313	High Similarity	NPC337373
0.9313	High Similarity	NPC188646
0.9313	High Similarity	NPC108113
0.9313	High Similarity	NPC175098
0.9313	High Similarity	NPC144051
0.9313	High Similarity	NPC472365
0.9313	High Similarity	NPC28753
0.9313	High Similarity	NPC263670
0.9313	High Similarity	NPC294593
0.9313	High Similarity	NPC242294
0.9313	High Similarity	NPC312318
0.9313	High Similarity	NPC82225
0.9313	High Similarity	NPC93756
0.9302	High Similarity	NPC84772
0.9297	High Similarity	NPC473907
0.9297	High Similarity	NPC80694
0.9297	High Similarity	NPC186098
0.9265	High Similarity	NPC328164
0.9265	High Similarity	NPC265040
0.9265	High Similarity	NPC306829
0.9265	High Similarity	NPC166482
0.9265	High Similarity	NPC194432
0.9265	High Similarity	NPC76372
0.9265	High Similarity	NPC161506
0.9265	High Similarity	NPC148757
0.9265	High Similarity	NPC125855
0.9265	High Similarity	NPC296917
0.9265	High Similarity	NPC66515
0.9265	High Similarity	NPC228504
0.9265	High Similarity	NPC182852
0.9265	High Similarity	NPC78
0.9265	High Similarity	NPC220998
0.9265	High Similarity	NPC64915
0.9265	High Similarity	NPC167624
0.9265	High Similarity	NPC107572
0.9265	High Similarity	NPC227579
0.9265	High Similarity	NPC223500
0.9265	High Similarity	NPC324134
0.9265	High Similarity	NPC177354
0.9265	High Similarity	NPC166934
0.9265	High Similarity	NPC1089
0.9265	High Similarity	NPC37496
0.9265	High Similarity	NPC40833
0.9265	High Similarity	NPC324436
0.9265	High Similarity	NPC76338
0.9265	High Similarity	NPC325346
0.9265	High Similarity	NPC32739
0.9265	High Similarity	NPC10937
0.9259	High Similarity	NPC241100
0.9259	High Similarity	NPC159275
0.9254	High Similarity	NPC470672
0.9254	High Similarity	NPC470669
0.9254	High Similarity	NPC470668
0.9254	High Similarity	NPC470671
0.9254	High Similarity	NPC474504
0.9254	High Similarity	NPC118813
0.9254	High Similarity	NPC474487
0.9242	High Similarity	NPC286336
0.9242	High Similarity	NPC164136
0.9237	High Similarity	NPC212631
0.9237	High Similarity	NPC129132
0.9237	High Similarity	NPC205468
0.9237	High Similarity	NPC87231
0.9237	High Similarity	NPC257756
0.9231	High Similarity	NPC324482
0.9225	High Similarity	NPC187907
0.9225	High Similarity	NPC230818
0.9225	High Similarity	NPC473894
0.9219	High Similarity	NPC475496
0.9219	High Similarity	NPC49852
0.9197	High Similarity	NPC164980
0.9197	High Similarity	NPC149026
0.9197	High Similarity	NPC150408
0.9197	High Similarity	NPC185276
0.9197	High Similarity	NPC75049
0.9197	High Similarity	NPC143896
0.9197	High Similarity	NPC81697
0.9197	High Similarity	NPC223812
0.9197	High Similarity	NPC107177
0.9197	High Similarity	NPC39329
0.9197	High Similarity	NPC214166
0.9197	High Similarity	NPC169591
0.9197	High Similarity	NPC310130
0.9197	High Similarity	NPC316816
0.9197	High Similarity	NPC125894
0.9197	High Similarity	NPC77794
0.9197	High Similarity	NPC85162
0.9197	High Similarity	NPC68104
0.9197	High Similarity	NPC221432
0.9197	High Similarity	NPC91560
0.9197	High Similarity	NPC175504
0.9197	High Similarity	NPC257097
0.9197	High Similarity	NPC278249
0.9197	High Similarity	NPC478086
0.9191	High Similarity	NPC110038
0.9191	High Similarity	NPC324386
0.9191	High Similarity	NPC4743
0.9191	High Similarity	NPC3188
0.9191	High Similarity	NPC171870
0.9191	High Similarity	NPC282300
0.9191	High Similarity	NPC262094
0.9191	High Similarity	NPC90582
0.9191	High Similarity	NPC96692
0.9191	High Similarity	NPC213322
0.9191	High Similarity	NPC110969
0.9191	High Similarity	NPC248372
0.9191	High Similarity	NPC312391
0.9185	High Similarity	NPC217186
0.9185	High Similarity	NPC152042
0.9185	High Similarity	NPC216978
0.9185	High Similarity	NPC261234
0.9185	High Similarity	NPC241838
0.9185	High Similarity	NPC37206
0.9185	High Similarity	NPC220062
0.9185	High Similarity	NPC18260
0.9185	High Similarity	NPC230902
0.9185	High Similarity	NPC143799
0.9185	High Similarity	NPC55018
0.9185	High Similarity	NPC78913
0.9185	High Similarity	NPC301217
0.9185	High Similarity	NPC471697
0.9185	High Similarity	NPC303633
0.9185	High Similarity	NPC96565

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 NPC203817 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	980
0.2-0.3	1789
0.3-0.4	2603
0.4-0.5	1760
0.5-0.6	1139
0.6-0.7	416
0.7-0.8	133
0.8-0.85	31
0.85-0.9	10
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9179	High Similarity	NPD1550	Clinical (unspecified phase)
0.9179	High Similarity	NPD1552	Clinical (unspecified phase)
0.9111	High Similarity	NPD1549	Phase 2
0.9015	High Similarity	NPD1240	Approved
0.8993	High Similarity	NPD4378	Clinical (unspecified phase)
0.8889	High Similarity	NPD1510	Phase 2
0.8881	High Similarity	NPD1607	Approved
0.8824	High Similarity	NPD2796	Approved
0.8786	High Similarity	NPD6799	Approved
0.8723	High Similarity	NPD7410	Clinical (unspecified phase)
0.8696	High Similarity	NPD970	Clinical (unspecified phase)
0.863	High Similarity	NPD2393	Clinical (unspecified phase)
0.8621	High Similarity	NPD7411	Suspended
0.8582	High Similarity	NPD6859	Clinical (unspecified phase)
0.8571	High Similarity	NPD8443	Clinical (unspecified phase)
0.8562	High Similarity	NPD1934	Approved
0.8521	High Similarity	NPD1511	Approved
0.8514	High Similarity	NPD3882	Suspended
0.8503	High Similarity	NPD2801	Approved
0.85	High Similarity	NPD2800	Approved
0.8467	Intermediate Similarity	NPD6651	Approved
0.8456	Intermediate Similarity	NPD7075	Discontinued
0.8425	Intermediate Similarity	NPD6599	Discontinued
0.8425	Intermediate Similarity	NPD4380	Phase 2
0.8417	Intermediate Similarity	NPD1551	Phase 2
0.8403	Intermediate Similarity	NPD1512	Approved
0.8378	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8311	Intermediate Similarity	NPD6801	Discontinued
0.831	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD9717	Approved
0.8239	Intermediate Similarity	NPD2654	Approved
0.8239	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD3817	Phase 2
0.8182	Intermediate Similarity	NPD3750	Approved
0.817	Intermediate Similarity	NPD6959	Discontinued
0.8146	Intermediate Similarity	NPD7768	Phase 2
0.8129	Intermediate Similarity	NPD6166	Phase 2
0.8129	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD1243	Approved
0.8095	Intermediate Similarity	NPD5403	Approved
0.8074	Intermediate Similarity	NPD1203	Approved
0.8045	Intermediate Similarity	NPD422	Phase 1
0.8029	Intermediate Similarity	NPD6832	Phase 2
0.8015	Intermediate Similarity	NPD9545	Approved
0.7975	Intermediate Similarity	NPD7054	Approved
0.7975	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD3749	Approved
0.7973	Intermediate Similarity	NPD920	Approved
0.7972	Intermediate Similarity	NPD2344	Approved
0.7959	Intermediate Similarity	NPD5401	Approved
0.7945	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7074	Phase 3
0.7925	Intermediate Similarity	NPD7472	Approved
0.7911	Intermediate Similarity	NPD3818	Discontinued
0.7908	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD6099	Approved
0.7902	Intermediate Similarity	NPD2935	Discontinued
0.7902	Intermediate Similarity	NPD6100	Approved
0.7879	Intermediate Similarity	NPD1548	Phase 1
0.7875	Intermediate Similarity	NPD6797	Phase 2
0.7875	Intermediate Similarity	NPD5953	Discontinued
0.7872	Intermediate Similarity	NPD230	Phase 1
0.7863	Intermediate Similarity	NPD9493	Approved
0.7862	Intermediate Similarity	NPD7286	Phase 2
0.7838	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD3748	Approved
0.7832	Intermediate Similarity	NPD2799	Discontinued
0.7826	Intermediate Similarity	NPD7251	Discontinued
0.7808	Intermediate Similarity	NPD4628	Phase 3
0.7778	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7808	Phase 3
0.777	Intermediate Similarity	NPD4908	Phase 1
0.7769	Intermediate Similarity	NPD1241	Discontinued
0.7756	Intermediate Similarity	NPD5494	Approved
0.7755	Intermediate Similarity	NPD2309	Approved
0.7754	Intermediate Similarity	NPD1019	Discontinued
0.7727	Intermediate Similarity	NPD5402	Approved
0.7708	Intermediate Similarity	NPD7033	Discontinued
0.7687	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD943	Approved
0.7669	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD3268	Approved
0.766	Intermediate Similarity	NPD411	Approved
0.766	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6232	Discontinued
0.7647	Intermediate Similarity	NPD1610	Phase 2
0.7625	Intermediate Similarity	NPD7473	Discontinued
0.7622	Intermediate Similarity	NPD447	Suspended
0.7607	Intermediate Similarity	NPD6559	Discontinued
0.7593	Intermediate Similarity	NPD1729	Discontinued
0.7586	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD919	Approved
0.7554	Intermediate Similarity	NPD2797	Approved
0.7547	Intermediate Similarity	NPD5711	Approved
0.7547	Intermediate Similarity	NPD5710	Approved
0.7535	Intermediate Similarity	NPD2313	Discontinued
0.7535	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6104	Discontinued
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7484	Intermediate Similarity	NPD1247	Approved
0.7482	Intermediate Similarity	NPD3225	Approved
0.7466	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD3972	Approved
0.7439	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3140	Approved
0.7431	Intermediate Similarity	NPD3142	Approved
0.7423	Intermediate Similarity	NPD5844	Phase 1
0.7417	Intermediate Similarity	NPD7390	Discontinued
0.741	Intermediate Similarity	NPD4749	Approved
0.7403	Intermediate Similarity	NPD3226	Approved
0.7379	Intermediate Similarity	NPD1933	Approved
0.7372	Intermediate Similarity	NPD1778	Approved
0.7347	Intermediate Similarity	NPD4308	Phase 3
0.7346	Intermediate Similarity	NPD2403	Approved
0.7338	Intermediate Similarity	NPD1608	Approved
0.7326	Intermediate Similarity	NPD4363	Phase 3
0.7326	Intermediate Similarity	NPD4360	Phase 2
0.7325	Intermediate Similarity	NPD1465	Phase 2
0.7324	Intermediate Similarity	NPD9494	Approved
0.7308	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3266	Approved
0.7305	Intermediate Similarity	NPD3267	Approved
0.7299	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6798	Discontinued
0.7292	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4361	Phase 2
0.7283	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1652	Phase 2
0.7255	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9266	Approved
0.7252	Intermediate Similarity	NPD74	Approved
0.7248	Intermediate Similarity	NPD2346	Discontinued
0.7241	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1894	Discontinued
0.7214	Intermediate Similarity	NPD1481	Phase 2
0.7203	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3496	Discontinued
0.7192	Intermediate Similarity	NPD1613	Approved
0.7192	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD940	Approved
0.7188	Intermediate Similarity	NPD846	Approved
0.7186	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD9263	Approved
0.7176	Intermediate Similarity	NPD9267	Approved
0.7176	Intermediate Similarity	NPD9264	Approved
0.7176	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4288	Approved
0.717	Intermediate Similarity	NPD2296	Approved
0.7153	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4661	Approved
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD1535	Discovery
0.7143	Intermediate Similarity	NPD4662	Approved
0.7134	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6002	Phase 3
0.7133	Intermediate Similarity	NPD5647	Approved
0.7133	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6004	Phase 3
0.7133	Intermediate Similarity	NPD6005	Phase 3
0.7123	Intermediate Similarity	NPD6233	Phase 2
0.7122	Intermediate Similarity	NPD17	Approved
0.7121	Intermediate Similarity	NPD2684	Approved
0.7103	Intermediate Similarity	NPD3027	Phase 3
0.7103	Intermediate Similarity	NPD4625	Phase 3
0.7092	Intermediate Similarity	NPD9269	Phase 2
0.7086	Intermediate Similarity	NPD2424	Discontinued
0.7078	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4307	Phase 2
0.707	Intermediate Similarity	NPD7458	Discontinued
0.7059	Intermediate Similarity	NPD3887	Approved
0.7059	Intermediate Similarity	NPD2354	Approved
0.7055	Intermediate Similarity	NPD7199	Phase 2
0.7055	Intermediate Similarity	NPD3764	Approved
0.705	Intermediate Similarity	NPD9268	Approved
0.7048	Intermediate Similarity	NPD3751	Discontinued
0.7045	Intermediate Similarity	NPD290	Approved
0.7044	Intermediate Similarity	NPD6279	Approved
0.7044	Intermediate Similarity	NPD6844	Discontinued
0.7044	Intermediate Similarity	NPD6280	Approved
0.7037	Intermediate Similarity	NPD7843	Approved
0.7022	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1091	Approved
0.7021	Intermediate Similarity	NPD1201	Approved
0.702	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1471	Phase 3

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