NPASS Compound

Structure

CID301178 OpenBabel06191716112D 21 22 0 0 0 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 6.0622 -1.5000 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 2.5981 -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 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 0.0000 -0.0000 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 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 6 2 0 0 0 0 2 10 1 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 13 18 2 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	291.039
LogP:	2.469
LogD:	2.579
LogS:	-2.763
# Rotatable Bonds:	4
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.457
Synthetic Accessibility Score:	2.174
Fsp3:	0.062
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:	-4.828
MDCK Permeability:	1.2880562280770391e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.088
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.217

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	98.60253143310547%
Volume Distribution (VD):	0.469
Pgp-substrate:	1.4336161613464355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.803
CYP2C19-inhibitor:	0.335
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.58
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.471
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.848
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	15.217
Half-life (T1/2):	0.932

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.763
AMES Toxicity:	0.811
Rat Oral Acute Toxicity:	0.773
Maximum Recommended Daily Dose:	0.824
Skin Sensitization:	0.952
Carcinogencity:	0.636
Eye Corrosion:	0.018
Eye Irritation:	0.958
Respiratory Toxicity:	0.639

Download Data

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

Natural Product: NPC301178

Natural Product ID:	NPC301178
*Common Name:**	Sappanchalcone
IUPAC Name:	(E)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)prop-2-en-1-one
Synonyms:	Sappanchalcone
Standard InCHIKey:	JVGNTXGHBHMJDO-QHHAFSJGSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-21-16-9-11(17)4-5-12(16)13(18)6-2-10-3-7-14(19)15(20)8-10/h2-9,17,19-20H,1H3/b6-2+
SMILES:	COc1cc(O)ccc1C(=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476986
PubChem CID:	5319493
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO32846	heamatoxylon campechianum	Species	n.a.	n.a.	stems	XiShuangBanNa, Yunnan Province, China	2005-Sep	PMID[18610999]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[19420770]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23127886]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234407]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	seeds	Nanning, Guangxi Province, China	2013-APR	PMID[26398312]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2554	Biancaea sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2554	Biancaea sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2554	Biancaea sappan	Species	Fabaceae	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	9

Activity Type	# Activity
Individual Protein	7
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	Inhibition	=	33.3	%	PMID[512052]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	Inhibition	=	83.5	%	PMID[512052]
NPT1479	Individual Protein	Stem cell growth factor receptor	Homo sapiens	Inhibition	=	44.7	%	PMID[512052]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	Inhibition	=	26.7	%	PMID[512052]
NPT1480	Individual Protein	Fibroblast growth factor receptor 1	Homo sapiens	Inhibition	=	86.9	%	PMID[512052]
NPT1481	Individual Protein	Fibroblast growth factor receptor 2	Homo sapiens	Inhibition	=	48.5	%	PMID[512052]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	Inhibition	=	64.3	%	PMID[512052]
NPT35	Others	n.a.		Activity	=	1.93	MU	PMID[512053]
NPT35	Others	n.a.		Activity	=	1.82	MU	PMID[512053]
NPT2	Others	Unspecified		IC50	=	32200.0	nM	PMID[512054]

☑ 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 NPC301178 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	385
0.1-0.2	1703
0.2-0.3	4787
0.3-0.4	11422
0.4-0.5	6014
0.5-0.6	3602
0.6-0.7	4962
0.7-0.8	5993
0.8-0.85	2375
0.85-0.9	1213
0.9-0.95	221
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC284556
0.9926	High Similarity	NPC471417
0.9781	High Similarity	NPC287722
0.9781	High Similarity	NPC254659
0.971	High Similarity	NPC142165
0.9638	High Similarity	NPC119663
0.9635	High Similarity	NPC110419
0.9574	High Similarity	NPC254702
0.9574	High Similarity	NPC194653
0.9574	High Similarity	NPC80710
0.9574	High Similarity	NPC139364
0.9574	High Similarity	NPC203747
0.9568	High Similarity	NPC242893
0.9568	High Similarity	NPC38065
0.9565	High Similarity	NPC312256
0.9507	High Similarity	NPC264550
0.9507	High Similarity	NPC92722
0.9507	High Similarity	NPC200060
0.9507	High Similarity	NPC40290
0.9507	High Similarity	NPC195763
0.9507	High Similarity	NPC38545
0.9507	High Similarity	NPC171916
0.9507	High Similarity	NPC264289
0.9507	High Similarity	NPC142876
0.9507	High Similarity	NPC102003
0.9507	High Similarity	NPC333691
0.9507	High Similarity	NPC69430
0.9507	High Similarity	NPC139293
0.9504	High Similarity	NPC95864
0.9504	High Similarity	NPC108406
0.9485	High Similarity	NPC472364
0.9485	High Similarity	NPC473391
0.9441	High Similarity	NPC472279
0.9441	High Similarity	NPC10467
0.9441	High Similarity	NPC85131
0.9437	High Similarity	NPC238279
0.9437	High Similarity	NPC131451
0.9437	High Similarity	NPC166036
0.9437	High Similarity	NPC287395
0.9437	High Similarity	NPC183655
0.9437	High Similarity	NPC15329
0.9437	High Similarity	NPC203077
0.9433	High Similarity	NPC12377
0.9429	High Similarity	NPC207732
0.9429	High Similarity	NPC105213
0.942	High Similarity	NPC50823
0.9375	High Similarity	NPC31363
0.9375	High Similarity	NPC256406
0.9375	High Similarity	NPC260895
0.9371	High Similarity	NPC183950
0.9371	High Similarity	NPC137062
0.9371	High Similarity	NPC270465
0.9371	High Similarity	NPC87125
0.9371	High Similarity	NPC52005
0.9371	High Similarity	NPC287101
0.9371	High Similarity	NPC105512
0.9371	High Similarity	NPC223579
0.9366	High Similarity	NPC119660
0.9366	High Similarity	NPC188074
0.9366	High Similarity	NPC93034
0.9366	High Similarity	NPC125449
0.9362	High Similarity	NPC70136
0.9362	High Similarity	NPC157133
0.9333	High Similarity	NPC129132
0.9333	High Similarity	NPC257756
0.9333	High Similarity	NPC87231
0.9333	High Similarity	NPC212631
0.9333	High Similarity	NPC205468
0.931	High Similarity	NPC39732
0.931	High Similarity	NPC324233
0.931	High Similarity	NPC35763
0.931	High Similarity	NPC323626
0.931	High Similarity	NPC257648
0.931	High Similarity	NPC245382
0.931	High Similarity	NPC100263
0.931	High Similarity	NPC121522
0.931	High Similarity	NPC55205
0.931	High Similarity	NPC100971
0.931	High Similarity	NPC216769
0.931	High Similarity	NPC304954
0.931	High Similarity	NPC131266
0.931	High Similarity	NPC60972
0.931	High Similarity	NPC209487
0.931	High Similarity	NPC477231
0.931	High Similarity	NPC269451
0.931	High Similarity	NPC181209
0.931	High Similarity	NPC291802
0.9306	High Similarity	NPC188871
0.9306	High Similarity	NPC184136
0.9306	High Similarity	NPC286342
0.9306	High Similarity	NPC29231
0.9306	High Similarity	NPC149127
0.9301	High Similarity	NPC218490
0.9301	High Similarity	NPC3036
0.9301	High Similarity	NPC119059
0.9301	High Similarity	NPC120464
0.9296	High Similarity	NPC165389
0.9291	High Similarity	NPC279121
0.9275	High Similarity	NPC44573
0.9265	High Similarity	NPC472365
0.9265	High Similarity	NPC312318
0.9265	High Similarity	NPC188646
0.9265	High Similarity	NPC242294
0.9265	High Similarity	NPC56031
0.9265	High Similarity	NPC175098
0.9265	High Similarity	NPC263670
0.9265	High Similarity	NPC192304
0.9265	High Similarity	NPC139813
0.9265	High Similarity	NPC337373
0.9259	High Similarity	NPC308037
0.9259	High Similarity	NPC64359
0.9259	High Similarity	NPC262359
0.9247	High Similarity	NPC469550
0.9247	High Similarity	NPC124714
0.9241	High Similarity	NPC252933
0.9241	High Similarity	NPC154345
0.9241	High Similarity	NPC45291
0.9241	High Similarity	NPC200740
0.9241	High Similarity	NPC19980
0.9241	High Similarity	NPC54394
0.9241	High Similarity	NPC125062
0.9236	High Similarity	NPC1612
0.9236	High Similarity	NPC183959
0.9236	High Similarity	NPC177298
0.9236	High Similarity	NPC48479
0.9231	High Similarity	NPC12200
0.9231	High Similarity	NPC168803
0.9231	High Similarity	NPC74881
0.9231	High Similarity	NPC86847
0.9231	High Similarity	NPC51443
0.9231	High Similarity	NPC140840
0.922	High Similarity	NPC175013
0.9197	High Similarity	NPC286336
0.9184	High Similarity	NPC117992
0.9184	High Similarity	NPC230149
0.9184	High Similarity	NPC234255
0.9184	High Similarity	NPC152951
0.9184	High Similarity	NPC256612
0.9184	High Similarity	NPC168247
0.9184	High Similarity	NPC39184
0.9184	High Similarity	NPC57674
0.9184	High Similarity	NPC20830
0.9184	High Similarity	NPC38898
0.9184	High Similarity	NPC2928
0.9178	High Similarity	NPC222830
0.9178	High Similarity	NPC239128
0.9178	High Similarity	NPC293183
0.9178	High Similarity	NPC187498
0.9178	High Similarity	NPC219582
0.9178	High Similarity	NPC162313
0.9178	High Similarity	NPC236637
0.9178	High Similarity	NPC260979
0.9178	High Similarity	NPC156222
0.9178	High Similarity	NPC83508
0.9178	High Similarity	NPC302950
0.9178	High Similarity	NPC275836
0.9178	High Similarity	NPC301323
0.9178	High Similarity	NPC198826
0.9178	High Similarity	NPC82325
0.9178	High Similarity	NPC212678
0.9178	High Similarity	NPC279989
0.9178	High Similarity	NPC241498
0.9178	High Similarity	NPC275722
0.9178	High Similarity	NPC57030
0.9178	High Similarity	NPC120163
0.9178	High Similarity	NPC131624
0.9178	High Similarity	NPC25270
0.9178	High Similarity	NPC100887
0.9178	High Similarity	NPC256283
0.9178	High Similarity	NPC71334
0.9178	High Similarity	NPC188203
0.9178	High Similarity	NPC472912
0.9172	High Similarity	NPC62042
0.9172	High Similarity	NPC156953
0.9172	High Similarity	NPC3825
0.9172	High Similarity	NPC88804
0.9167	High Similarity	NPC474903
0.9167	High Similarity	NPC294852
0.9167	High Similarity	NPC43669
0.9167	High Similarity	NPC12367
0.9167	High Similarity	NPC188679
0.9167	High Similarity	NPC272721
0.9167	High Similarity	NPC195202
0.9167	High Similarity	NPC118726
0.9167	High Similarity	NPC19545
0.9167	High Similarity	NPC196277
0.9167	High Similarity	NPC321011
0.9161	High Similarity	NPC143903
0.9161	High Similarity	NPC179271
0.9161	High Similarity	NPC138978
0.9161	High Similarity	NPC20791
0.9161	High Similarity	NPC226987
0.9149	High Similarity	NPC299154
0.9149	High Similarity	NPC49108
0.9143	High Similarity	NPC109232
0.9137	High Similarity	NPC7013
0.9137	High Similarity	NPC116632
0.9137	High Similarity	NPC209560
0.9137	High Similarity	NPC162680
0.9137	High Similarity	NPC303644

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 NPC301178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	977
0.2-0.3	1667
0.3-0.4	2707
0.4-0.5	1759
0.5-0.6	1070
0.6-0.7	435
0.7-0.8	136
0.8-0.85	25
0.85-0.9	14
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9291	High Similarity	NPD1511	Approved
0.9178	High Similarity	NPD1934	Approved
0.9161	High Similarity	NPD1512	Approved
0.9122	High Similarity	NPD3882	Suspended
0.9118	High Similarity	NPD1240	Approved
0.9116	High Similarity	NPD2393	Clinical (unspecified phase)
0.9116	High Similarity	NPD2801	Approved
0.8993	High Similarity	NPD1510	Phase 2
0.8986	High Similarity	NPD1607	Approved
0.8978	High Similarity	NPD943	Approved
0.8671	High Similarity	NPD1549	Phase 2
0.8601	High Similarity	NPD1550	Clinical (unspecified phase)
0.8601	High Similarity	NPD1552	Clinical (unspecified phase)
0.859	High Similarity	NPD6166	Phase 2
0.859	High Similarity	NPD6167	Clinical (unspecified phase)
0.859	High Similarity	NPD6168	Clinical (unspecified phase)
0.8571	High Similarity	NPD4378	Clinical (unspecified phase)
0.8553	High Similarity	NPD3817	Phase 2
0.8542	High Similarity	NPD970	Clinical (unspecified phase)
0.8533	High Similarity	NPD4380	Phase 2
0.8503	High Similarity	NPD6799	Approved
0.8481	Intermediate Similarity	NPD3818	Discontinued
0.8428	Intermediate Similarity	NPD7054	Approved
0.8403	Intermediate Similarity	NPD2796	Approved
0.838	Intermediate Similarity	NPD230	Phase 1
0.8377	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD7472	Approved
0.8375	Intermediate Similarity	NPD7074	Phase 3
0.8344	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6797	Phase 2
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8322	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD7473	Discontinued
0.8276	Intermediate Similarity	NPD2935	Discontinued
0.8272	Intermediate Similarity	NPD7251	Discontinued
0.8247	Intermediate Similarity	NPD7819	Suspended
0.8247	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD6599	Discontinued
0.8151	Intermediate Similarity	NPD1551	Phase 2
0.8117	Intermediate Similarity	NPD7411	Suspended
0.811	Intermediate Similarity	NPD7808	Phase 3
0.811	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD5494	Approved
0.8092	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD9494	Approved
0.8077	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6801	Discontinued
0.8058	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD3750	Approved
0.8013	Intermediate Similarity	NPD1465	Phase 2
0.7972	Intermediate Similarity	NPD3027	Phase 3
0.7959	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3926	Phase 2
0.7945	Intermediate Similarity	NPD6651	Approved
0.7925	Intermediate Similarity	NPD919	Approved
0.7917	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD447	Suspended
0.7867	Intermediate Similarity	NPD2800	Approved
0.7862	Intermediate Similarity	NPD3749	Approved
0.7857	Intermediate Similarity	NPD5403	Approved
0.7857	Intermediate Similarity	NPD9269	Phase 2
0.7852	Intermediate Similarity	NPD2344	Approved
0.7848	Intermediate Similarity	NPD5402	Approved
0.7843	Intermediate Similarity	NPD5401	Approved
0.7843	Intermediate Similarity	NPD2533	Approved
0.7843	Intermediate Similarity	NPD2532	Approved
0.7843	Intermediate Similarity	NPD2534	Approved
0.7832	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1247	Approved
0.7826	Intermediate Similarity	NPD6959	Discontinued
0.7817	Intermediate Similarity	NPD1203	Approved
0.7808	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1613	Approved
0.7799	Intermediate Similarity	NPD7768	Phase 2
0.7791	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD5844	Phase 1
0.7748	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1243	Approved
0.7725	Intermediate Similarity	NPD6559	Discontinued
0.7718	Intermediate Similarity	NPD3748	Approved
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7662	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2309	Approved
0.7639	Intermediate Similarity	NPD2798	Approved
0.7635	Intermediate Similarity	NPD1933	Approved
0.7632	Intermediate Similarity	NPD2654	Approved
0.7628	Intermediate Similarity	NPD920	Approved
0.7609	Intermediate Similarity	NPD9493	Approved
0.7606	Intermediate Similarity	NPD9717	Approved
0.76	Intermediate Similarity	NPD2799	Discontinued
0.7597	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD9268	Approved
0.756	Intermediate Similarity	NPD5953	Discontinued
0.7554	Intermediate Similarity	NPD5536	Phase 2
0.755	Intermediate Similarity	NPD6099	Approved
0.755	Intermediate Similarity	NPD6100	Approved
0.7548	Intermediate Similarity	NPD7390	Discontinued
0.7534	Intermediate Similarity	NPD6832	Phase 2
0.7532	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD6190	Approved
0.7517	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3972	Approved
0.7466	Intermediate Similarity	NPD3018	Phase 2
0.7448	Intermediate Similarity	NPD1470	Approved
0.744	Intermediate Similarity	NPD7286	Phase 2
0.7436	Intermediate Similarity	NPD4357	Discontinued
0.7432	Intermediate Similarity	NPD411	Approved
0.7432	Intermediate Similarity	NPD2313	Discontinued
0.7414	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD422	Phase 1
0.7413	Intermediate Similarity	NPD1201	Approved
0.7413	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7199	Phase 2
0.7386	Intermediate Similarity	NPD2346	Discontinued
0.7381	Intermediate Similarity	NPD3751	Discontinued
0.7378	Intermediate Similarity	NPD6234	Discontinued
0.7376	Intermediate Similarity	NPD1548	Phase 1
0.7372	Intermediate Similarity	NPD228	Approved
0.7368	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1608	Approved
0.7355	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2982	Phase 2
0.731	Intermediate Similarity	NPD2983	Phase 2
0.7305	Intermediate Similarity	NPD5242	Approved
0.7305	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4908	Phase 1
0.7292	Intermediate Similarity	NPD1610	Phase 2
0.7284	Intermediate Similarity	NPD37	Approved
0.7278	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1876	Approved
0.7255	Intermediate Similarity	NPD4308	Phase 3
0.725	Intermediate Similarity	NPD1653	Approved
0.7246	Intermediate Similarity	NPD5711	Approved
0.7246	Intermediate Similarity	NPD5710	Approved
0.7241	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2981	Phase 2
0.7234	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6385	Approved
0.7222	Intermediate Similarity	NPD6386	Approved
0.7211	Intermediate Similarity	NPD1164	Approved
0.7209	Intermediate Similarity	NPD7685	Pre-registration
0.7208	Intermediate Similarity	NPD5406	Approved
0.7208	Intermediate Similarity	NPD5408	Approved
0.7208	Intermediate Similarity	NPD5405	Approved
0.7208	Intermediate Similarity	NPD5404	Approved
0.7205	Intermediate Similarity	NPD7458	Discontinued
0.72	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3268	Approved
0.72	Intermediate Similarity	NPD3764	Approved
0.7195	Intermediate Similarity	NPD5353	Approved
0.7153	Intermediate Similarity	NPD17	Approved
0.7152	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD4967	Phase 2
0.7152	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7143	Intermediate Similarity	NPD3225	Approved
0.7099	Intermediate Similarity	NPD3455	Phase 2
0.7095	Intermediate Similarity	NPD2797	Approved
0.7091	Intermediate Similarity	NPD4288	Approved
0.7091	Intermediate Similarity	NPD2296	Approved
0.7089	Intermediate Similarity	NPD2354	Approved
0.7076	Intermediate Similarity	NPD7228	Approved
0.7072	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7266	Discontinued
0.7051	Intermediate Similarity	NPD1471	Phase 3
0.7047	Intermediate Similarity	NPD1019	Discontinued
0.7029	Intermediate Similarity	NPD9266	Approved
0.7029	Intermediate Similarity	NPD74	Approved
0.7027	Intermediate Similarity	NPD1283	Approved
0.7025	Intermediate Similarity	NPD7003	Approved
0.7025	Intermediate Similarity	NPD8166	Discontinued
0.7021	Intermediate Similarity	NPD5283	Phase 1
0.702	Intermediate Similarity	NPD4625	Phase 3
0.7006	Intermediate Similarity	NPD6971	Discontinued
0.6994	Remote Similarity	NPD824	Approved
0.6994	Remote Similarity	NPD1729	Discontinued
0.6993	Remote Similarity	NPD4307	Phase 2
0.698	Remote Similarity	NPD3266	Approved
0.698	Remote Similarity	NPD3267	Approved
0.6978	Remote Similarity	NPD3021	Approved
0.6978	Remote Similarity	NPD3022	Approved
0.6974	Remote Similarity	NPD6798	Discontinued
0.6974	Remote Similarity	NPD1296	Phase 2
0.697	Remote Similarity	NPD6844	Discontinued
0.6966	Remote Similarity	NPD1651	Approved
0.6961	Remote Similarity	NPD4363	Phase 3
0.6961	Remote Similarity	NPD4360	Phase 2

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