NPASS Compound

Structure

CID35598 OpenBabel06191715362D 39 41 0 0 0 0 0 0 0 0999 V2000 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 2.5000 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 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -12.1244 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 -11.2583 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 -10.3923 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 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 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 38 1 0 0 0 0 3 9 1 0 0 0 0 3 18 2 0 0 0 0 4 11 2 0 0 0 0 4 19 1 0 0 0 0 5 14 2 0 0 0 0 5 19 1 0 0 0 0 6 8 2 0 0 0 0 6 20 1 0 0 0 0 7 12 2 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 13 2 0 0 0 0 10 23 1 0 0 0 0 11 26 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 29 1 0 0 0 0 15 19 2 0 0 0 0 15 28 1 0 0 0 0 16 21 2 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 17 39 1 0 0 0 0 20 27 2 0 0 0 0 21 31 1 0 0 0 0 22 25 2 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 23 30 2 0 0 0 0 24 32 2 0 0 0 0 25 33 1 0 0 0 0 26 28 2 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 28 38 1 0 0 0 0 29 36 2 0 0 0 0 29 39 1 0 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.17
Volume:	543.968
LogP:	4.393
LogD:	3.104
LogS:	-3.573
# Rotatable Bonds:	11
TPSA:	153.75
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.107
Synthetic Accessibility Score:	3.01
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.283
MDCK Permeability:	1.2713977412204258e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.097
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.313
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	101.33898162841797%
Volume Distribution (VD):	0.29
Pgp-substrate:	0.4537493586540222%

ADMET: Metabolism

CYP1A2-inhibitor:	0.763
CYP1A2-substrate:	0.651
CYP2C19-inhibitor:	0.766
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.893
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.576
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.503
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	10.78
Half-life (T1/2):	0.965

ADMET: Toxicity

hERG Blockers:	0.126
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.506
AMES Toxicity:	0.682
Rat Oral Acute Toxicity:	0.261
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.968
Carcinogencity:	0.523
Eye Corrosion:	0.003
Eye Irritation:	0.888
Respiratory Toxicity:	0.161

Download Data

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

Natural Product: NPC35598

Natural Product ID:	NPC35598
*Common Name:**	Gemichalcones C
IUPAC Name:	[(Z)-4-[3-[(E)-3-(2,4-dihydroxyphenyl)prop-2-enoyl]-2,6-dihydroxyphenyl]-2-methylbut-2-enyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:	Gemichalcones C
Standard InCHIKey:	OFKHJNZDWNKYOY-DBLNWHOKSA-N
Standard InCHI:	InChI=1S/C30H28O9/c1-18(17-39-29(36)14-5-19-4-11-26(34)28(15-19)38-2)3-9-22-25(33)13-10-23(30(22)37)24(32)12-7-20-6-8-21(31)16-27(20)35/h3-8,10-16,31,33-35,37H,9,17H2,1-2H3/b12-7+,14-5+,18-3-
SMILES:	COc1cc(/C=C/C(=O)OC/C(=CCc2c(O)ccc(c2O)C(=O)/C=C/c2ccc(cc2O)O)/C)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499860
PubChem CID:	10626094
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003509] 3-prenylated chalcones

*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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	heartwood	n.a.	n.a.	PMID[16643064]
NPO28998	Hypericum geminiflorum	Species	Hypericaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[18512985]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	roots	Khon Kaen, Thailand	2009-DEC	PMID[25537111]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28998	Hypericum geminiflorum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28998	Hypericum geminiflorum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5495	Broussonetia papyrifera	Species	Moraceae	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	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	23900.0	nM	PMID[505852]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	37600.0	nM	PMID[505852]
NPT113	Cell Line	RAW264.7	Mus musculus	Ratio CC50/IC50	=	1.6	n.a.	PMID[505852]

☑ 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 NPC35598 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	371
0.1-0.2	1567
0.2-0.3	3851
0.3-0.4	8904
0.4-0.5	9338
0.5-0.6	3342
0.6-0.7	4899
0.7-0.8	5843
0.8-0.85	3273
0.85-0.9	1192
0.9-0.95	112
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC222689
0.9487	High Similarity	NPC471788
0.9404	High Similarity	NPC256406
0.9281	High Similarity	NPC475895
0.9272	High Similarity	NPC171916
0.9272	High Similarity	NPC38545
0.9236	High Similarity	NPC476247
0.9226	High Similarity	NPC291508
0.9221	High Similarity	NPC117992
0.9221	High Similarity	NPC57674
0.9221	High Similarity	NPC230149
0.9221	High Similarity	NPC234255
0.9221	High Similarity	NPC168247
0.9221	High Similarity	NPC152951
0.9216	High Similarity	NPC199773
0.9216	High Similarity	NPC237994
0.9211	High Similarity	NPC472279
0.9205	High Similarity	NPC203747
0.9205	High Similarity	NPC254702
0.9205	High Similarity	NPC238279
0.9205	High Similarity	NPC166036
0.9205	High Similarity	NPC194653
0.9205	High Similarity	NPC203077
0.9205	High Similarity	NPC139364
0.9205	High Similarity	NPC80710
0.9172	High Similarity	NPC142252
0.9167	High Similarity	NPC74178
0.9167	High Similarity	NPC184755
0.9161	High Similarity	NPC278778
0.9161	High Similarity	NPC291878
0.9161	High Similarity	NPC471787
0.9161	High Similarity	NPC195796
0.9161	High Similarity	NPC472455
0.9161	High Similarity	NPC35038
0.9156	High Similarity	NPC33051
0.9156	High Similarity	NPC227337
0.9156	High Similarity	NPC49402
0.9156	High Similarity	NPC273462
0.9156	High Similarity	NPC70433
0.9145	High Similarity	NPC200060
0.9145	High Similarity	NPC139293
0.9145	High Similarity	NPC142876
0.9145	High Similarity	NPC333691
0.9145	High Similarity	NPC69430
0.9145	High Similarity	NPC264289
0.9145	High Similarity	NPC40290
0.9145	High Similarity	NPC264550
0.9145	High Similarity	NPC195763
0.9133	High Similarity	NPC157133
0.913	High Similarity	NPC476365
0.9128	High Similarity	NPC254659
0.9108	High Similarity	NPC292415
0.9108	High Similarity	NPC53889
0.9103	High Similarity	NPC78103
0.9103	High Similarity	NPC472598
0.9103	High Similarity	NPC474055
0.9103	High Similarity	NPC27337
0.9103	High Similarity	NPC52889
0.9097	High Similarity	NPC134287
0.9097	High Similarity	NPC130589
0.9097	High Similarity	NPC477503
0.9097	High Similarity	NPC470327
0.9097	High Similarity	NPC256925
0.9097	High Similarity	NPC39184
0.9097	High Similarity	NPC472280
0.9097	High Similarity	NPC45849
0.9097	High Similarity	NPC200761
0.9091	High Similarity	NPC257648
0.9091	High Similarity	NPC472912
0.9091	High Similarity	NPC471982
0.9091	High Similarity	NPC477231
0.9091	High Similarity	NPC324233
0.9091	High Similarity	NPC323626
0.9074	High Similarity	NPC81332
0.9074	High Similarity	NPC262580
0.9074	High Similarity	NPC289396
0.9074	High Similarity	NPC271848
0.9074	High Similarity	NPC212038
0.9073	High Similarity	NPC12377
0.9067	High Similarity	NPC142165
0.9062	High Similarity	NPC13481
0.9062	High Similarity	NPC207575
0.9051	High Similarity	NPC472634
0.9051	High Similarity	NPC266314
0.9051	High Similarity	NPC471499
0.9051	High Similarity	NPC26326
0.9051	High Similarity	NPC158188
0.9051	High Similarity	NPC473106
0.9051	High Similarity	NPC349525
0.9051	High Similarity	NPC103201
0.9051	High Similarity	NPC112418
0.9045	High Similarity	NPC284127
0.9045	High Similarity	NPC87317
0.9045	High Similarity	NPC476410
0.9045	High Similarity	NPC172202
0.9045	High Similarity	NPC204879
0.9038	High Similarity	NPC227062
0.9038	High Similarity	NPC209614
0.9038	High Similarity	NPC282307
0.9038	High Similarity	NPC470328
0.9038	High Similarity	NPC472626
0.9038	High Similarity	NPC170026
0.9032	High Similarity	NPC124714
0.9032	High Similarity	NPC469550
0.9032	High Similarity	NPC250557
0.9032	High Similarity	NPC192083
0.9032	High Similarity	NPC298802
0.9032	High Similarity	NPC213896
0.9032	High Similarity	NPC18727
0.9026	High Similarity	NPC154345
0.9026	High Similarity	NPC31363
0.9013	High Similarity	NPC188074
0.9013	High Similarity	NPC125449
0.9	High Similarity	NPC119663
0.9	High Similarity	NPC471417
0.8994	High Similarity	NPC471745
0.8994	High Similarity	NPC474034
0.8994	High Similarity	NPC472635
0.8994	High Similarity	NPC474033
0.8987	High Similarity	NPC119209
0.8987	High Similarity	NPC287328
0.8987	High Similarity	NPC470326
0.8987	High Similarity	NPC328102
0.8987	High Similarity	NPC472631
0.8987	High Similarity	NPC282009
0.8987	High Similarity	NPC118256
0.8987	High Similarity	NPC472630
0.8987	High Similarity	NPC36217
0.8987	High Similarity	NPC476980
0.8987	High Similarity	NPC192686
0.8987	High Similarity	NPC471744
0.8987	High Similarity	NPC472624
0.8981	High Similarity	NPC223787
0.8981	High Similarity	NPC38779
0.8981	High Similarity	NPC63454
0.8981	High Similarity	NPC160512
0.8981	High Similarity	NPC156818
0.8981	High Similarity	NPC129684
0.8981	High Similarity	NPC68324
0.8981	High Similarity	NPC289322
0.8981	High Similarity	NPC262286
0.8981	High Similarity	NPC36852
0.8981	High Similarity	NPC108456
0.8981	High Similarity	NPC219867
0.8981	High Similarity	NPC187745
0.8981	High Similarity	NPC161960
0.8981	High Similarity	NPC299520
0.8981	High Similarity	NPC474681
0.8981	High Similarity	NPC218313
0.8981	High Similarity	NPC78225
0.8981	High Similarity	NPC180011
0.8981	High Similarity	NPC183851
0.8981	High Similarity	NPC67876
0.8981	High Similarity	NPC37543
0.8981	High Similarity	NPC178976
0.8981	High Similarity	NPC199463
0.8981	High Similarity	NPC304008
0.8981	High Similarity	NPC114179
0.8974	High Similarity	NPC226025
0.8974	High Similarity	NPC286052
0.8974	High Similarity	NPC321779
0.8974	High Similarity	NPC38898
0.8968	High Similarity	NPC245382
0.8968	High Similarity	NPC60972
0.8968	High Similarity	NPC219582
0.8968	High Similarity	NPC35763
0.8968	High Similarity	NPC149889
0.8968	High Similarity	NPC302950
0.8968	High Similarity	NPC39732
0.8968	High Similarity	NPC100263
0.8968	High Similarity	NPC291802
0.8968	High Similarity	NPC260979
0.8968	High Similarity	NPC121522
0.8968	High Similarity	NPC209487
0.8968	High Similarity	NPC269451
0.8968	High Similarity	NPC289968
0.8968	High Similarity	NPC106976
0.8968	High Similarity	NPC236637
0.8968	High Similarity	NPC216769
0.8968	High Similarity	NPC131266
0.8968	High Similarity	NPC312338
0.8968	High Similarity	NPC181209
0.8968	High Similarity	NPC100971
0.8961	High Similarity	NPC29231
0.8961	High Similarity	NPC3825
0.8961	High Similarity	NPC85131
0.8961	High Similarity	NPC88804
0.8957	High Similarity	NPC476370
0.8957	High Similarity	NPC158226
0.8951	High Similarity	NPC280493
0.8951	High Similarity	NPC475212
0.8947	High Similarity	NPC25844
0.894	High Similarity	NPC207732
0.894	High Similarity	NPC38065
0.894	High Similarity	NPC242893
0.894	High Similarity	NPC105213
0.8938	High Similarity	NPC124038
0.8938	High Similarity	NPC234004
0.8933	High Similarity	NPC284556
0.8933	High Similarity	NPC301178

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 NPC35598 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	946
0.2-0.3	1679
0.3-0.4	2552
0.4-0.5	1871
0.5-0.6	1086
0.6-0.7	487
0.7-0.8	148
0.8-0.85	43
0.85-0.9	16
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9032	High Similarity	NPD2393	Clinical (unspecified phase)
0.8994	High Similarity	NPD6232	Discontinued
0.8968	High Similarity	NPD1934	Approved
0.8944	High Similarity	NPD7473	Discontinued
0.8917	High Similarity	NPD4868	Clinical (unspecified phase)
0.8882	High Similarity	NPD6166	Phase 2
0.8882	High Similarity	NPD6167	Clinical (unspecified phase)
0.8882	High Similarity	NPD6168	Clinical (unspecified phase)
0.8861	High Similarity	NPD7075	Discontinued
0.8854	High Similarity	NPD3817	Phase 2
0.8797	High Similarity	NPD3882	Suspended
0.879	High Similarity	NPD2801	Approved
0.8782	High Similarity	NPD7411	Suspended
0.8718	High Similarity	NPD4380	Phase 2
0.8671	High Similarity	NPD7819	Suspended
0.8671	High Similarity	NPD7096	Clinical (unspecified phase)
0.8659	High Similarity	NPD3818	Discontinued
0.8608	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD1511	Approved
0.8554	High Similarity	NPD7074	Phase 3
0.8526	High Similarity	NPD6980	Clinical (unspecified phase)
0.8516	High Similarity	NPD7410	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD5844	Phase 1
0.8494	Intermediate Similarity	NPD7054	Approved
0.8462	Intermediate Similarity	NPD1512	Approved
0.8452	Intermediate Similarity	NPD6799	Approved
0.8443	Intermediate Similarity	NPD7472	Approved
0.8424	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8402	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD2935	Discontinued
0.8333	Intermediate Similarity	NPD7768	Phase 2
0.8312	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5494	Approved
0.8284	Intermediate Similarity	NPD6797	Phase 2
0.8282	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1240	Approved
0.8267	Intermediate Similarity	NPD943	Approved
0.825	Intermediate Similarity	NPD6599	Discontinued
0.8247	Intermediate Similarity	NPD1549	Phase 2
0.8235	Intermediate Similarity	NPD6559	Discontinued
0.8235	Intermediate Similarity	NPD7251	Discontinued
0.8232	Intermediate Similarity	NPD919	Approved
0.8218	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD1465	Phase 2
0.8187	Intermediate Similarity	NPD7808	Phase 3
0.8182	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1607	Approved
0.8133	Intermediate Similarity	NPD6959	Discontinued
0.8129	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2796	Approved
0.8101	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD230	Phase 1
0.8063	Intermediate Similarity	NPD5403	Approved
0.8059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD2534	Approved
0.805	Intermediate Similarity	NPD2533	Approved
0.805	Intermediate Similarity	NPD2532	Approved
0.8049	Intermediate Similarity	NPD5402	Approved
0.8024	Intermediate Similarity	NPD7199	Phase 2
0.8012	Intermediate Similarity	NPD6234	Discontinued
0.7952	Intermediate Similarity	NPD3749	Approved
0.7937	Intermediate Similarity	NPD5401	Approved
0.7929	Intermediate Similarity	NPD3926	Phase 2
0.7929	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD3750	Approved
0.7885	Intermediate Similarity	NPD1551	Phase 2
0.7862	Intermediate Similarity	NPD6190	Approved
0.7861	Intermediate Similarity	NPD5953	Discontinued
0.7857	Intermediate Similarity	NPD447	Suspended
0.7853	Intermediate Similarity	NPD3226	Approved
0.7841	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2799	Discontinued
0.7818	Intermediate Similarity	NPD37	Approved
0.7811	Intermediate Similarity	NPD1247	Approved
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7799	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4965	Approved
0.7784	Intermediate Similarity	NPD4967	Phase 2
0.7784	Intermediate Similarity	NPD4966	Approved
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7390	Discontinued
0.7747	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7458	Discontinued
0.7742	Intermediate Similarity	NPD1933	Approved
0.7736	Intermediate Similarity	NPD1243	Approved
0.773	Intermediate Similarity	NPD920	Approved
0.7717	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3027	Phase 3
0.7702	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD9494	Approved
0.7692	Intermediate Similarity	NPD6651	Approved
0.7688	Intermediate Similarity	NPD7228	Approved
0.7667	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2313	Discontinued
0.7658	Intermediate Similarity	NPD5404	Approved
0.7658	Intermediate Similarity	NPD5406	Approved
0.7658	Intermediate Similarity	NPD5405	Approved
0.7658	Intermediate Similarity	NPD5408	Approved
0.7647	Intermediate Similarity	NPD6832	Phase 2
0.7644	Intermediate Similarity	NPD7286	Phase 2
0.7627	Intermediate Similarity	NPD8312	Approved
0.7627	Intermediate Similarity	NPD8313	Approved
0.761	Intermediate Similarity	NPD2346	Discontinued
0.7607	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3748	Approved
0.7595	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD8151	Discontinued
0.7576	Intermediate Similarity	NPD1653	Approved
0.7566	Intermediate Similarity	NPD1203	Approved
0.7564	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1613	Approved
0.7548	Intermediate Similarity	NPD6798	Discontinued
0.7532	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2800	Approved
0.7514	Intermediate Similarity	NPD5242	Approved
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD8150	Discontinued
0.7483	Intermediate Similarity	NPD9269	Phase 2
0.7469	Intermediate Similarity	NPD8166	Discontinued
0.7469	Intermediate Similarity	NPD7003	Approved
0.7469	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5710	Approved
0.7457	Intermediate Similarity	NPD5711	Approved
0.7436	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7435	Discontinued
0.7405	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2798	Approved
0.7394	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD9717	Approved
0.7356	Intermediate Similarity	NPD7229	Phase 3
0.7342	Intermediate Similarity	NPD4060	Phase 1
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.734	Intermediate Similarity	NPD6777	Approved
0.7337	Intermediate Similarity	NPD6385	Approved
0.7337	Intermediate Similarity	NPD6386	Approved
0.7325	Intermediate Similarity	NPD3764	Approved
0.7325	Intermediate Similarity	NPD3268	Approved
0.7317	Intermediate Similarity	NPD2309	Approved
0.731	Intermediate Similarity	NPD5353	Approved
0.7308	Intermediate Similarity	NPD4908	Phase 1
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7299	Intermediate Similarity	NPD8127	Discontinued
0.7288	Intermediate Similarity	NPD3751	Discontinued
0.7284	Intermediate Similarity	NPD7266	Discontinued
0.7278	Intermediate Similarity	NPD6233	Phase 2
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD9545	Approved
0.7267	Intermediate Similarity	NPD7033	Discontinued
0.7251	Intermediate Similarity	NPD8455	Phase 2
0.7248	Intermediate Similarity	NPD9493	Approved
0.7226	Intermediate Similarity	NPD1470	Approved
0.7226	Intermediate Similarity	NPD1164	Approved
0.7226	Intermediate Similarity	NPD2797	Approved
0.7222	Intermediate Similarity	NPD7240	Approved
0.7222	Intermediate Similarity	NPD6099	Approved
0.7222	Intermediate Similarity	NPD6100	Approved
0.7219	Intermediate Similarity	NPD9268	Approved
0.7219	Intermediate Similarity	NPD3455	Phase 2
0.7215	Intermediate Similarity	NPD411	Approved
0.72	Intermediate Similarity	NPD5536	Phase 2
0.7198	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7177	Discontinued
0.719	Intermediate Similarity	NPD1201	Approved
0.719	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7179	Intermediate Similarity	NPD7874	Approved
0.7179	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD5049	Phase 3
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6273	Approved
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7697	Approved
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.7127	Intermediate Similarity	NPD7038	Approved
0.7127	Intermediate Similarity	NPD7039	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