NPASS Compound

Structure

NPC102003 OpenBabel07101718272D 25 26 0 0 0 0 0 0 0 0999 V2000 3.4641 0.0000 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 -1.7321 -0.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -4.3301 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -5.1962 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 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 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 -0.5000 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 -6.0622 1.5000 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 2.5981 -0.5000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 2 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.11
Volume:	343.211
LogP:	2.624
LogD:	2.51
LogS:	-3.115
# Rotatable Bonds:	6
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.419
Synthetic Accessibility Score:	2.428
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.887
MDCK Permeability:	1.3689988918486051e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	98.0571060180664%
Volume Distribution (VD):	0.432
Pgp-substrate:	6.055263996124268%

ADMET: Metabolism

CYP1A2-inhibitor:	0.891
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.111
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.395
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.124
CYP2D6-substrate:	0.763
CYP3A4-inhibitor:	0.57
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	13.118
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.177
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.759
AMES Toxicity:	0.43
Rat Oral Acute Toxicity:	0.805
Maximum Recommended Daily Dose:	0.721
Skin Sensitization:	0.947
Carcinogencity:	0.409
Eye Corrosion:	0.004
Eye Irritation:	0.934
Respiratory Toxicity:	0.835

Download Data

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

Natural Product: NPC102003

Natural Product ID:	NPC102003
*Common Name:**	Hamilcone
IUPAC Name:	(E)-3-(3,4-dihydroxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one
Synonyms:	hamilcone
Standard InCHIKey:	ZORDSTUSHFTNGS-FNORWQNLSA-N
Standard InCHI:	InChI=1S/C18H18O7/c1-23-15-9-14(22)16(18(25-3)17(15)24-2)12(20)7-5-10-4-6-11(19)13(21)8-10/h4-9,19,21-22H,1-3H3/b7-5+
SMILES:	COc1cc(O)c(c(c1OC)OC)C(=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465364
PubChem CID:	10688914
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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	=	8.0	ug.mL-1	PMID[458200]
NPT2	Others	Unspecified		Activity	=	47.0	%	PMID[458200]
NPT2	Others	Unspecified		Activity	=	0.6	n.a.	PMID[458200]

☑ 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 NPC102003 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	410
0.1-0.2	1807
0.2-0.3	5002
0.3-0.4	11375
0.4-0.5	5949
0.5-0.6	3623
0.6-0.7	4982
0.7-0.8	5835
0.8-0.85	2210
0.85-0.9	1125
0.9-0.95	345
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC92722
0.993	High Similarity	NPC15329
0.993	High Similarity	NPC131451
0.9859	High Similarity	NPC93034
0.9859	High Similarity	NPC119660
0.979	High Similarity	NPC287395
0.979	High Similarity	NPC183655
0.9789	High Similarity	NPC165389
0.9726	High Similarity	NPC124714
0.966	High Similarity	NPC20830
0.966	High Similarity	NPC256612
0.9658	High Similarity	NPC245382
0.9658	High Similarity	NPC209487
0.9658	High Similarity	NPC216769
0.9658	High Similarity	NPC100263
0.9658	High Similarity	NPC100971
0.9658	High Similarity	NPC35763
0.9658	High Similarity	NPC269451
0.9658	High Similarity	NPC291802
0.9658	High Similarity	NPC121522
0.9658	High Similarity	NPC181209
0.9658	High Similarity	NPC131266
0.9648	High Similarity	NPC142165
0.9595	High Similarity	NPC472916
0.9592	High Similarity	NPC183878
0.9592	High Similarity	NPC145379
0.9592	High Similarity	NPC160951
0.9592	High Similarity	NPC176775
0.9592	High Similarity	NPC255350
0.9592	High Similarity	NPC231018
0.9592	High Similarity	NPC47781
0.9592	High Similarity	NPC250557
0.9592	High Similarity	NPC274327
0.9592	High Similarity	NPC22519
0.9592	High Similarity	NPC69394
0.9589	High Similarity	NPC19980
0.9589	High Similarity	NPC45291
0.9589	High Similarity	NPC262623
0.9577	High Similarity	NPC119663
0.9577	High Similarity	NPC471417
0.9577	High Similarity	NPC254659
0.9527	High Similarity	NPC2476
0.9527	High Similarity	NPC138360
0.9527	High Similarity	NPC280339
0.9527	High Similarity	NPC39184
0.9527	High Similarity	NPC130589
0.9527	High Similarity	NPC4455
0.9527	High Similarity	NPC163780
0.9527	High Similarity	NPC50715
0.9527	High Similarity	NPC227325
0.9527	High Similarity	NPC183597
0.9527	High Similarity	NPC128863
0.9527	High Similarity	NPC2928
0.9527	High Similarity	NPC134287
0.9527	High Similarity	NPC201136
0.9527	High Similarity	NPC146165
0.9527	High Similarity	NPC213622
0.9527	High Similarity	NPC196439
0.9527	High Similarity	NPC167815
0.9527	High Similarity	NPC92659
0.9527	High Similarity	NPC208197
0.9524	High Similarity	NPC256283
0.9524	High Similarity	NPC239128
0.9524	High Similarity	NPC71334
0.9524	High Similarity	NPC120163
0.9524	High Similarity	NPC187498
0.9524	High Similarity	NPC222830
0.9524	High Similarity	NPC39732
0.9524	High Similarity	NPC188203
0.9524	High Similarity	NPC275836
0.9524	High Similarity	NPC275722
0.9524	High Similarity	NPC241498
0.9524	High Similarity	NPC60972
0.9524	High Similarity	NPC100887
0.9524	High Similarity	NPC131624
0.9524	High Similarity	NPC198826
0.9524	High Similarity	NPC293183
0.9524	High Similarity	NPC83508
0.9524	High Similarity	NPC212678
0.9524	High Similarity	NPC57030
0.9524	High Similarity	NPC301323
0.9524	High Similarity	NPC162313
0.9524	High Similarity	NPC25270
0.9524	High Similarity	NPC156222
0.9521	High Similarity	NPC10467
0.9521	High Similarity	NPC239363
0.9521	High Similarity	NPC156953
0.9521	High Similarity	NPC472279
0.9514	High Similarity	NPC226987
0.9514	High Similarity	NPC143903
0.951	High Similarity	NPC207732
0.9507	High Similarity	NPC301178
0.9507	High Similarity	NPC284556
0.9507	High Similarity	NPC312256
0.9467	High Similarity	NPC195832
0.9463	High Similarity	NPC49824
0.9459	High Similarity	NPC271779
0.9459	High Similarity	NPC292214
0.9459	High Similarity	NPC472915
0.9459	High Similarity	NPC88645
0.9459	High Similarity	NPC167091
0.9459	High Similarity	NPC276409
0.9459	High Similarity	NPC206238
0.9459	High Similarity	NPC250822
0.9459	High Similarity	NPC75279
0.9456	High Similarity	NPC226973
0.9456	High Similarity	NPC208043
0.9456	High Similarity	NPC308451
0.9452	High Similarity	NPC40290
0.9452	High Similarity	NPC195763
0.9452	High Similarity	NPC69430
0.9452	High Similarity	NPC264289
0.9452	High Similarity	NPC200060
0.9452	High Similarity	NPC264550
0.9452	High Similarity	NPC333691
0.9452	High Similarity	NPC139293
0.9452	High Similarity	NPC142876
0.9441	High Similarity	NPC287722
0.9437	High Similarity	NPC58229
0.9437	High Similarity	NPC110419
0.9404	High Similarity	NPC476980
0.94	High Similarity	NPC472911
0.94	High Similarity	NPC110070
0.94	High Similarity	NPC470402
0.94	High Similarity	NPC48208
0.94	High Similarity	NPC245758
0.94	High Similarity	NPC224137
0.94	High Similarity	NPC156057
0.94	High Similarity	NPC262286
0.94	High Similarity	NPC210084
0.94	High Similarity	NPC36852
0.94	High Similarity	NPC75215
0.94	High Similarity	NPC78225
0.94	High Similarity	NPC203891
0.94	High Similarity	NPC99597
0.94	High Similarity	NPC475267
0.94	High Similarity	NPC474208
0.94	High Similarity	NPC472910
0.94	High Similarity	NPC227192
0.94	High Similarity	NPC162869
0.94	High Similarity	NPC189179
0.94	High Similarity	NPC472913
0.94	High Similarity	NPC472914
0.94	High Similarity	NPC101830
0.94	High Similarity	NPC474836
0.94	High Similarity	NPC222814
0.94	High Similarity	NPC78103
0.94	High Similarity	NPC96167
0.94	High Similarity	NPC93376
0.9396	High Similarity	NPC44079
0.9396	High Similarity	NPC201451
0.9396	High Similarity	NPC26227
0.9392	High Similarity	NPC257648
0.9392	High Similarity	NPC199100
0.9392	High Similarity	NPC120537
0.9392	High Similarity	NPC101996
0.9392	High Similarity	NPC39007
0.9392	High Similarity	NPC477231
0.9392	High Similarity	NPC180234
0.9392	High Similarity	NPC142540
0.9392	High Similarity	NPC161277
0.9388	High Similarity	NPC306821
0.9388	High Similarity	NPC45873
0.9388	High Similarity	NPC184136
0.9384	High Similarity	NPC139364
0.9384	High Similarity	NPC80710
0.9384	High Similarity	NPC194653
0.9384	High Similarity	NPC218490
0.9384	High Similarity	NPC254702
0.9384	High Similarity	NPC203747
0.9366	High Similarity	NPC50823
0.9342	High Similarity	NPC258331
0.9338	High Similarity	NPC204854
0.9338	High Similarity	NPC105242
0.9338	High Similarity	NPC9609
0.9338	High Similarity	NPC4481
0.9338	High Similarity	NPC261004
0.9338	High Similarity	NPC19687
0.9338	High Similarity	NPC193842
0.9338	High Similarity	NPC143828
0.9338	High Similarity	NPC18772
0.9338	High Similarity	NPC22472
0.9338	High Similarity	NPC152166
0.9338	High Similarity	NPC176300
0.9338	High Similarity	NPC191459
0.9338	High Similarity	NPC288669
0.9338	High Similarity	NPC130894
0.9338	High Similarity	NPC7846
0.9338	High Similarity	NPC300943
0.9338	High Similarity	NPC115798
0.9338	High Similarity	NPC18607
0.9338	High Similarity	NPC253634
0.9338	High Similarity	NPC25495
0.9333	High Similarity	NPC98661
0.9333	High Similarity	NPC235165
0.9333	High Similarity	NPC191146
0.9333	High Similarity	NPC255106
0.9333	High Similarity	NPC245546
0.9333	High Similarity	NPC474520
0.9333	High Similarity	NPC474167

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 NPC102003 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	986
0.2-0.3	1811
0.3-0.4	2736
0.4-0.5	1665
0.5-0.6	1020
0.6-0.7	383
0.7-0.8	127
0.8-0.85	26
0.85-0.9	14
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9592	High Similarity	NPD2801	Approved
0.9205	High Similarity	NPD3882	Suspended
0.9133	High Similarity	NPD1934	Approved
0.898	High Similarity	NPD1511	Approved
0.8947	High Similarity	NPD2393	Clinical (unspecified phase)
0.8859	High Similarity	NPD1512	Approved
0.8688	High Similarity	NPD3818	Discontinued
0.8679	High Similarity	NPD6167	Clinical (unspecified phase)
0.8679	High Similarity	NPD6168	Clinical (unspecified phase)
0.8679	High Similarity	NPD6166	Phase 2
0.8671	High Similarity	NPD943	Approved
0.8671	High Similarity	NPD1240	Approved
0.8645	High Similarity	NPD3817	Phase 2
0.8562	High Similarity	NPD1510	Phase 2
0.8553	High Similarity	NPD6232	Discontinued
0.8552	High Similarity	NPD1607	Approved
0.8544	High Similarity	NPD5494	Approved
0.8537	High Similarity	NPD4338	Clinical (unspecified phase)
0.8519	High Similarity	NPD7054	Approved
0.8509	High Similarity	NPD7473	Discontinued
0.8506	High Similarity	NPD4380	Phase 2
0.8471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7472	Approved
0.8466	Intermediate Similarity	NPD7074	Phase 3
0.8421	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD2935	Discontinued
0.8355	Intermediate Similarity	NPD6799	Approved
0.8303	Intermediate Similarity	NPD6797	Phase 2
0.8267	Intermediate Similarity	NPD1549	Phase 2
0.8253	Intermediate Similarity	NPD7251	Discontinued
0.8231	Intermediate Similarity	NPD230	Phase 1
0.8204	Intermediate Similarity	NPD7808	Phase 3
0.82	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7075	Discontinued
0.8187	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5402	Approved
0.8148	Intermediate Similarity	NPD1247	Approved
0.8146	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2796	Approved
0.8113	Intermediate Similarity	NPD1465	Phase 2
0.8113	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD3027	Phase 3
0.8077	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5844	Phase 1
0.8069	Intermediate Similarity	NPD9494	Approved
0.8065	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3926	Phase 2
0.8042	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD7819	Suspended
0.7987	Intermediate Similarity	NPD447	Suspended
0.7976	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6801	Discontinued
0.7922	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7411	Suspended
0.784	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2532	Approved
0.7834	Intermediate Similarity	NPD2534	Approved
0.7834	Intermediate Similarity	NPD2533	Approved
0.7816	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD1551	Phase 2
0.777	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6190	Approved
0.7751	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2800	Approved
0.7736	Intermediate Similarity	NPD5403	Approved
0.7724	Intermediate Similarity	NPD9269	Phase 2
0.7719	Intermediate Similarity	NPD6559	Discontinued
0.7712	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6959	Discontinued
0.7703	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6651	Approved
0.7692	Intermediate Similarity	NPD3750	Approved
0.7682	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1613	Approved
0.7667	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD3749	Approved
0.7613	Intermediate Similarity	NPD2344	Approved
0.761	Intermediate Similarity	NPD5401	Approved
0.759	Intermediate Similarity	NPD6234	Discontinued
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7578	Intermediate Similarity	NPD1653	Approved
0.7576	Intermediate Similarity	NPD7768	Phase 2
0.7574	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD5536	Phase 2
0.7547	Intermediate Similarity	NPD4357	Discontinued
0.7543	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1933	Approved
0.7516	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD920	Approved
0.7515	Intermediate Similarity	NPD5242	Approved
0.75	Intermediate Similarity	NPD37	Approved
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7467	Intermediate Similarity	NPD3018	Phase 2
0.7457	Intermediate Similarity	NPD5953	Discontinued
0.745	Intermediate Similarity	NPD1203	Approved
0.7448	Intermediate Similarity	NPD9268	Approved
0.7442	Intermediate Similarity	NPD7286	Phase 2
0.7439	Intermediate Similarity	NPD6385	Approved
0.7439	Intermediate Similarity	NPD6386	Approved
0.7438	Intermediate Similarity	NPD7390	Discontinued
0.7432	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3226	Approved
0.7421	Intermediate Similarity	NPD2309	Approved
0.7414	Intermediate Similarity	NPD7685	Pre-registration
0.741	Intermediate Similarity	NPD5353	Approved
0.7405	Intermediate Similarity	NPD2654	Approved
0.7405	Intermediate Similarity	NPD1243	Approved
0.74	Intermediate Similarity	NPD2798	Approved
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3748	Approved
0.7365	Intermediate Similarity	NPD4966	Approved
0.7365	Intermediate Similarity	NPD4965	Approved
0.7365	Intermediate Similarity	NPD4967	Phase 2
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.7325	Intermediate Similarity	NPD6100	Approved
0.7325	Intermediate Similarity	NPD6099	Approved
0.732	Intermediate Similarity	NPD2313	Discontinued
0.7315	Intermediate Similarity	NPD2982	Phase 2
0.7315	Intermediate Similarity	NPD2983	Phase 2
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6832	Phase 2
0.729	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD2346	Discontinued
0.7267	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD228	Approved
0.7251	Intermediate Similarity	NPD5711	Approved
0.7251	Intermediate Similarity	NPD5710	Approved
0.7248	Intermediate Similarity	NPD3972	Approved
0.7248	Intermediate Similarity	NPD9717	Approved
0.7248	Intermediate Similarity	NPD2981	Phase 2
0.7243	Intermediate Similarity	NPD6782	Approved
0.7243	Intermediate Similarity	NPD6780	Approved
0.7243	Intermediate Similarity	NPD6778	Approved
0.7243	Intermediate Similarity	NPD6776	Approved
0.7243	Intermediate Similarity	NPD6777	Approved
0.7243	Intermediate Similarity	NPD6781	Approved
0.7243	Intermediate Similarity	NPD6779	Approved
0.7241	Intermediate Similarity	NPD9493	Approved
0.7231	Intermediate Similarity	NPD2899	Discontinued
0.7219	Intermediate Similarity	NPD1470	Approved
0.7186	Intermediate Similarity	NPD6844	Discontinued
0.7175	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9545	Approved
0.7128	Intermediate Similarity	NPD7435	Discontinued
0.7111	Intermediate Similarity	NPD8434	Phase 2
0.7111	Intermediate Similarity	NPD8150	Discontinued
0.7108	Intermediate Similarity	NPD824	Approved
0.7108	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD411	Approved
0.7078	Intermediate Similarity	NPD4908	Phase 1
0.7069	Intermediate Similarity	NPD2403	Approved
0.7067	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1201	Approved
0.7067	Intermediate Similarity	NPD422	Phase 1
0.7063	Intermediate Similarity	NPD7266	Discontinued
0.7051	Intermediate Similarity	NPD6233	Phase 2
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7037	Intermediate Similarity	NPD7696	Phase 3
0.7037	Intermediate Similarity	NPD7698	Approved
0.7037	Intermediate Similarity	NPD7697	Approved
0.7034	Intermediate Similarity	NPD5283	Phase 1
0.7031	Intermediate Similarity	NPD8151	Discontinued
0.7027	Intermediate Similarity	NPD1548	Phase 1
0.702	Intermediate Similarity	NPD1608	Approved
0.7007	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3455	Phase 2
0.7	Intermediate Similarity	NPD7871	Phase 2
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD7870	Phase 2
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5406	Approved
0.6989	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3764	Approved
0.6987	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3268	Approved
0.6984	Remote Similarity	NPD6823	Phase 2
0.6979	Remote Similarity	NPD7701	Phase 2
0.6973	Remote Similarity	NPD6535	Approved
0.6973	Remote Similarity	NPD6534	Approved
0.6957	Remote Similarity	NPD3540	Phase 1
0.6954	Remote Similarity	NPD1610	Phase 2
0.6937	Remote Similarity	NPD4308	Phase 3
0.6937	Remote Similarity	NPD7033	Discontinued
0.6928	Remote Similarity	NPD1876	Approved
0.6928	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1481	Phase 2
0.6907	Remote Similarity	NPD7875	Clinical (unspecified phase)

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