NPASS Compound

Structure

NPC474208 OpenBabel07101719522D 25 27 0 0 1 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 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 3.4641 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 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 3 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 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 6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -1.7321 -0.0000 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 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 21 2 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.11
Volume:	337.291
LogP:	1.892
LogD:	2.286
LogS:	-3.56
# Rotatable Bonds:	4
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.822
Synthetic Accessibility Score:	2.936
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	1.5776839063619263e-05
Pgp-inhibitor:	0.298
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	91.76091766357422%
Volume Distribution (VD):	0.607
Pgp-substrate:	15.741199493408203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.129
CYP1A2-substrate:	0.906
CYP2C19-inhibitor:	0.546
CYP2C19-substrate:	0.554
CYP2C9-inhibitor:	0.718
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.205
CYP2D6-substrate:	0.597
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.622

ADMET: Excretion

Clearance (CL):	11.512
Half-life (T1/2):	0.644

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.763
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.806
Maximum Recommended Daily Dose:	0.249
Skin Sensitization:	0.819
Carcinogencity:	0.23
Eye Corrosion:	0.003
Eye Irritation:	0.87
Respiratory Toxicity:	0.647

Download Data

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

Natural Product: NPC474208

Natural Product ID:	NPC474208
*Common Name:**	Hamiltone B
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5,6,7-trimethoxy-2,3-dihydrochromen-4-one
Synonyms:	hamiltone B
Standard InCHIKey:	PYMGYISATWYZMS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O7/c1-22-15-8-14-16(18(24-3)17(15)23-2)12(21)7-13(25-14)9-4-5-10(19)11(20)6-9/h4-6,8,13,19-20H,7H2,1-3H3
SMILES:	COc1cc2OC(CC(=O)c2c(c1OC)OC)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463498
PubChem CID:	9798295
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14552774]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	leaf and stem	n.a.	n.a.	PMID[9584399]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	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
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[481454]
NPT2	Others	Unspecified		Activity	=	76.0	%	PMID[481454]
NPT2	Others	Unspecified		Activity	=	1.0	n.a.	PMID[481454]

☑ 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 NPC474208 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	412
0.1-0.2	1664
0.2-0.3	4454
0.3-0.4	10476
0.4-0.5	7329
0.5-0.6	3431
0.6-0.7	4706
0.7-0.8	5377
0.8-0.85	2537
0.85-0.9	1564
0.9-0.95	642
0.95-1	105

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475267
1.0	High Similarity	NPC48208
1.0	High Similarity	NPC156057
1.0	High Similarity	NPC474836
1.0	High Similarity	NPC162869
0.9933	High Similarity	NPC255106
0.9933	High Similarity	NPC235165
0.9867	High Similarity	NPC472910
0.9867	High Similarity	NPC222814
0.9867	High Similarity	NPC210084
0.9867	High Similarity	NPC96167
0.9867	High Similarity	NPC99597
0.9867	High Similarity	NPC472914
0.9867	High Similarity	NPC472913
0.9867	High Similarity	NPC472911
0.9867	High Similarity	NPC245758
0.9866	High Similarity	NPC37392
0.9801	High Similarity	NPC250214
0.9801	High Similarity	NPC95936
0.98	High Similarity	NPC472916
0.9799	High Similarity	NPC18727
0.9737	High Similarity	NPC263449
0.9735	High Similarity	NPC78225
0.9735	High Similarity	NPC470402
0.9735	High Similarity	NPC469584
0.9735	High Similarity	NPC223787
0.9733	High Similarity	NPC213622
0.9733	High Similarity	NPC472909
0.9733	High Similarity	NPC2928
0.9732	High Similarity	NPC180234
0.9732	High Similarity	NPC236637
0.9732	High Similarity	NPC120537
0.9732	High Similarity	NPC219582
0.9732	High Similarity	NPC302950
0.9732	High Similarity	NPC199100
0.9673	High Similarity	NPC308992
0.9673	High Similarity	NPC266314
0.9671	High Similarity	NPC152904
0.9669	High Similarity	NPC191146
0.9669	High Similarity	NPC195796
0.9669	High Similarity	NPC291878
0.9669	High Similarity	NPC68093
0.9669	High Similarity	NPC278778
0.9669	High Similarity	NPC35038
0.9667	High Similarity	NPC206238
0.9667	High Similarity	NPC472915
0.9667	High Similarity	NPC69394
0.9667	High Similarity	NPC88645
0.9667	High Similarity	NPC145379
0.9667	High Similarity	NPC183878
0.9667	High Similarity	NPC22519
0.9667	High Similarity	NPC292214
0.9667	High Similarity	NPC176775
0.9667	High Similarity	NPC167091
0.9667	High Similarity	NPC231018
0.9667	High Similarity	NPC274327
0.9667	High Similarity	NPC47781
0.9667	High Similarity	NPC160951
0.9667	High Similarity	NPC271779
0.9667	High Similarity	NPC255350
0.9664	High Similarity	NPC204515
0.9664	High Similarity	NPC117579
0.9613	High Similarity	NPC224280
0.9605	High Similarity	NPC36852
0.9605	High Similarity	NPC471479
0.9605	High Similarity	NPC300727
0.9605	High Similarity	NPC472598
0.9605	High Similarity	NPC471515
0.9605	High Similarity	NPC262286
0.9605	High Similarity	NPC291508
0.9605	High Similarity	NPC241904
0.9605	High Similarity	NPC474055
0.9605	High Similarity	NPC27337
0.9605	High Similarity	NPC299520
0.9605	High Similarity	NPC181960
0.9605	High Similarity	NPC129684
0.9603	High Similarity	NPC256612
0.9603	High Similarity	NPC167815
0.9603	High Similarity	NPC196439
0.9603	High Similarity	NPC50715
0.9603	High Similarity	NPC183597
0.9603	High Similarity	NPC227325
0.9603	High Similarity	NPC128863
0.9603	High Similarity	NPC4455
0.9603	High Similarity	NPC20830
0.9603	High Similarity	NPC201136
0.9603	High Similarity	NPC146165
0.9603	High Similarity	NPC470327
0.9603	High Similarity	NPC92659
0.9603	High Similarity	NPC2476
0.9603	High Similarity	NPC138360
0.9603	High Similarity	NPC280339
0.9603	High Similarity	NPC163780
0.9603	High Similarity	NPC477503
0.9603	High Similarity	NPC45849
0.9603	High Similarity	NPC200761
0.96	High Similarity	NPC275836
0.96	High Similarity	NPC477231
0.96	High Similarity	NPC162313
0.96	High Similarity	NPC100887
0.96	High Similarity	NPC39007
0.96	High Similarity	NPC293183
0.96	High Similarity	NPC120163
0.96	High Similarity	NPC472912
0.96	High Similarity	NPC239128
0.96	High Similarity	NPC187498
0.96	High Similarity	NPC71334
0.96	High Similarity	NPC161277
0.96	High Similarity	NPC275722
0.96	High Similarity	NPC301323
0.96	High Similarity	NPC156222
0.96	High Similarity	NPC83508
0.96	High Similarity	NPC198826
0.96	High Similarity	NPC101996
0.96	High Similarity	NPC188203
0.96	High Similarity	NPC131624
0.96	High Similarity	NPC212678
0.96	High Similarity	NPC222830
0.96	High Similarity	NPC257648
0.96	High Similarity	NPC25270
0.96	High Similarity	NPC256283
0.96	High Similarity	NPC57030
0.96	High Similarity	NPC241498
0.9597	High Similarity	NPC62042
0.9597	High Similarity	NPC61620
0.9597	High Similarity	NPC338131
0.9548	High Similarity	NPC475985
0.9542	High Similarity	NPC329091
0.9542	High Similarity	NPC476242
0.9539	High Similarity	NPC320825
0.9539	High Similarity	NPC326037
0.9539	High Similarity	NPC138243
0.9539	High Similarity	NPC472626
0.9539	High Similarity	NPC13858
0.9539	High Similarity	NPC209614
0.9539	High Similarity	NPC303255
0.9539	High Similarity	NPC49824
0.9539	High Similarity	NPC201837
0.9539	High Similarity	NPC274730
0.9539	High Similarity	NPC317383
0.9539	High Similarity	NPC470328
0.9539	High Similarity	NPC471500
0.9536	High Similarity	NPC124714
0.9536	High Similarity	NPC280937
0.9536	High Similarity	NPC250822
0.9536	High Similarity	NPC276409
0.9536	High Similarity	NPC213896
0.9536	High Similarity	NPC192083
0.9536	High Similarity	NPC75279
0.9533	High Similarity	NPC149614
0.9533	High Similarity	NPC251110
0.9533	High Similarity	NPC208043
0.9533	High Similarity	NPC226973
0.9533	High Similarity	NPC31363
0.9533	High Similarity	NPC171010
0.949	High Similarity	NPC14662
0.949	High Similarity	NPC243877
0.9487	High Similarity	NPC326520
0.9487	High Similarity	NPC234052
0.9484	High Similarity	NPC83922
0.9484	High Similarity	NPC472448
0.9484	High Similarity	NPC81679
0.9481	High Similarity	NPC36217
0.9481	High Similarity	NPC56085
0.9481	High Similarity	NPC14353
0.9481	High Similarity	NPC118256
0.9481	High Similarity	NPC204290
0.9481	High Similarity	NPC476980
0.9481	High Similarity	NPC228785
0.9481	High Similarity	NPC282009
0.9481	High Similarity	NPC192686
0.9481	High Similarity	NPC472624
0.9481	High Similarity	NPC119209
0.9481	High Similarity	NPC287328
0.9477	High Similarity	NPC67876
0.9477	High Similarity	NPC227192
0.9477	High Similarity	NPC203891
0.9477	High Similarity	NPC224137
0.9477	High Similarity	NPC101830
0.9477	High Similarity	NPC93376
0.9477	High Similarity	NPC189179
0.9477	High Similarity	NPC75215
0.9477	High Similarity	NPC110070
0.9477	High Similarity	NPC52530
0.9474	High Similarity	NPC31018
0.9474	High Similarity	NPC44079
0.9474	High Similarity	NPC117992
0.9474	High Similarity	NPC26227
0.9474	High Similarity	NPC113906
0.9474	High Similarity	NPC230149
0.9474	High Similarity	NPC321779
0.9474	High Similarity	NPC255807
0.9474	High Similarity	NPC201451
0.9474	High Similarity	NPC208197
0.9474	High Similarity	NPC57674
0.9474	High Similarity	NPC226025
0.9474	High Similarity	NPC152951
0.9474	High Similarity	NPC67396
0.9474	High Similarity	NPC168247
0.947	High Similarity	NPC216769

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 NPC474208 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	947
0.2-0.3	1820
0.3-0.4	2643
0.4-0.5	1726
0.5-0.6	970
0.6-0.7	484
0.7-0.8	132
0.8-0.85	35
0.85-0.9	13
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9732	High Similarity	NPD1934	Approved
0.9667	High Similarity	NPD2801	Approved
0.9536	High Similarity	NPD2393	Clinical (unspecified phase)
0.9241	High Similarity	NPD6168	Clinical (unspecified phase)
0.9241	High Similarity	NPD6166	Phase 2
0.9241	High Similarity	NPD6167	Clinical (unspecified phase)
0.9161	High Similarity	NPD3882	Suspended
0.9067	High Similarity	NPD1511	Approved
0.9012	High Similarity	NPD7074	Phase 3
0.9006	High Similarity	NPD3818	Discontinued
0.8987	High Similarity	NPD5494	Approved
0.8963	High Similarity	NPD4338	Clinical (unspecified phase)
0.8951	High Similarity	NPD7054	Approved
0.8947	High Similarity	NPD1512	Approved
0.8917	High Similarity	NPD4868	Clinical (unspecified phase)
0.8896	High Similarity	NPD7472	Approved
0.8854	High Similarity	NPD3817	Phase 2
0.8792	High Similarity	NPD1550	Clinical (unspecified phase)
0.8792	High Similarity	NPD1552	Clinical (unspecified phase)
0.8733	High Similarity	NPD1549	Phase 2
0.8727	High Similarity	NPD6797	Phase 2
0.8718	High Similarity	NPD4380	Phase 2
0.8675	High Similarity	NPD7251	Discontinued
0.8636	High Similarity	NPD4378	Clinical (unspecified phase)
0.8625	High Similarity	NPD4381	Clinical (unspecified phase)
0.8625	High Similarity	NPD7075	Discontinued
0.8623	High Similarity	NPD7808	Phase 3
0.8553	High Similarity	NPD7096	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD5844	Phase 1
0.8477	Intermediate Similarity	NPD2796	Approved
0.8415	Intermediate Similarity	NPD6232	Discontinued
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8393	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD5402	Approved
0.8373	Intermediate Similarity	NPD7473	Discontinued
0.8333	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD1465	Phase 2
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8274	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1240	Approved
0.8267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1613	Approved
0.8267	Intermediate Similarity	NPD943	Approved
0.8261	Intermediate Similarity	NPD6801	Discontinued
0.8242	Intermediate Similarity	NPD1247	Approved
0.8242	Intermediate Similarity	NPD6959	Discontinued
0.8199	Intermediate Similarity	NPD7411	Suspended
0.8165	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1607	Approved
0.8137	Intermediate Similarity	NPD6599	Discontinued
0.8129	Intermediate Similarity	NPD6559	Discontinued
0.8121	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3027	Phase 3
0.8054	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD2935	Discontinued
0.7974	Intermediate Similarity	NPD230	Phase 1
0.795	Intermediate Similarity	NPD5403	Approved
0.791	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD919	Approved
0.7901	Intermediate Similarity	NPD1653	Approved
0.7898	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD447	Suspended
0.7848	Intermediate Similarity	NPD2800	Approved
0.7844	Intermediate Similarity	NPD3749	Approved
0.784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD2533	Approved
0.7826	Intermediate Similarity	NPD2532	Approved
0.7826	Intermediate Similarity	NPD2534	Approved
0.7826	Intermediate Similarity	NPD5401	Approved
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7799	Intermediate Similarity	NPD3750	Approved
0.7798	Intermediate Similarity	NPD6234	Discontinued
0.7791	Intermediate Similarity	NPD3751	Discontinued
0.7784	Intermediate Similarity	NPD7768	Phase 2
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7765	Intermediate Similarity	NPD3787	Discontinued
0.775	Intermediate Similarity	NPD6190	Approved
0.774	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7199	Phase 2
0.7697	Intermediate Similarity	NPD9494	Approved
0.7658	Intermediate Similarity	NPD6100	Approved
0.7658	Intermediate Similarity	NPD6099	Approved
0.7654	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1933	Approved
0.7622	Intermediate Similarity	NPD920	Approved
0.7616	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2344	Approved
0.7605	Intermediate Similarity	NPD37	Approved
0.7586	Intermediate Similarity	NPD7228	Approved
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4967	Phase 2
0.7574	Intermediate Similarity	NPD4965	Approved
0.7574	Intermediate Similarity	NPD4966	Approved
0.7557	Intermediate Similarity	NPD5953	Discontinued
0.755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7286	Phase 2
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4908	Phase 1
0.753	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD6844	Discontinued
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3748	Approved
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7472	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2861	Phase 2
0.7468	Intermediate Similarity	NPD6651	Approved
0.7436	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD2309	Approved
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7414	Intermediate Similarity	NPD5242	Approved
0.7412	Intermediate Similarity	NPD5353	Approved
0.7407	Intermediate Similarity	NPD1243	Approved
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7394	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6233	Phase 2
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7362	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5711	Approved
0.7356	Intermediate Similarity	NPD5710	Approved
0.7351	Intermediate Similarity	NPD4360	Phase 2
0.7351	Intermediate Similarity	NPD4363	Phase 3
0.7338	Intermediate Similarity	NPD1203	Approved
0.7337	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7390	Discontinued
0.7325	Intermediate Similarity	NPD6798	Discontinued
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7255	Intermediate Similarity	NPD9269	Phase 2
0.7239	Intermediate Similarity	NPD2424	Discontinued
0.7235	Intermediate Similarity	NPD6386	Approved
0.7235	Intermediate Similarity	NPD6385	Approved
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7225	Intermediate Similarity	NPD7698	Approved
0.7225	Intermediate Similarity	NPD7697	Approved
0.7225	Intermediate Similarity	NPD7696	Phase 3
0.7216	Intermediate Similarity	NPD8151	Discontinued
0.7215	Intermediate Similarity	NPD3268	Approved
0.7202	Intermediate Similarity	NPD7584	Approved
0.7195	Intermediate Similarity	NPD1652	Phase 2
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7182	Intermediate Similarity	NPD7549	Discontinued
0.7179	Intermediate Similarity	NPD2798	Approved
0.7178	Intermediate Similarity	NPD7266	Discontinued
0.7175	Intermediate Similarity	NPD2403	Approved
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.7166	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD6535	Approved
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.7159	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.715	Intermediate Similarity	NPD2899	Discontinued
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.7127	Intermediate Similarity	NPD7240	Approved
0.7126	Intermediate Similarity	NPD4357	Discontinued
0.7118	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2797	Approved
0.7097	Intermediate Similarity	NPD4749	Approved
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2654	Approved
0.7086	Intermediate Similarity	NPD5536	Phase 2
0.7083	Intermediate Similarity	NPD4661	Approved
0.7083	Intermediate Similarity	NPD4662	Approved
0.7081	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5124	Phase 1
0.7078	Intermediate Similarity	NPD422	Phase 1
0.7069	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7801	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