NPASS Compound

Structure

CID222572 OpenBabel06191716012D 22 24 0 0 1 0 0 0 0 0999 V2000 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 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 -0.5000 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 -0.5000 -0.8660 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 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 -0.8660 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 1.7321 -0.0000 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 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 4 1 0 0 0 0 2 11 2 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 17 1 0 0 0 0 10 22 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 6 0 0 0 16 21 1 0 0 0 0 17 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.12
Volume:	305.051
LogP:	2.25
LogD:	2.463
LogS:	-3.32
# Rotatable Bonds:	3
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.809
Synthetic Accessibility Score:	3.426
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.622
MDCK Permeability:	1.2467227861634456e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.842
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	93.12151336669922%
Volume Distribution (VD):	0.794
Pgp-substrate:	9.76740550994873%

ADMET: Metabolism

CYP1A2-inhibitor:	0.57
CYP1A2-substrate:	0.502
CYP2C19-inhibitor:	0.298
CYP2C19-substrate:	0.22
CYP2C9-inhibitor:	0.375
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.644
CYP2D6-substrate:	0.865
CYP3A4-inhibitor:	0.859
CYP3A4-substrate:	0.528

ADMET: Excretion

Clearance (CL):	13.716
Half-life (T1/2):	0.774

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.112
AMES Toxicity:	0.691
Rat Oral Acute Toxicity:	0.342
Maximum Recommended Daily Dose:	0.683
Skin Sensitization:	0.925
Carcinogencity:	0.356
Eye Corrosion:	0.003
Eye Irritation:	0.699
Respiratory Toxicity:	0.407

Download Data

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

Natural Product: NPC222572

Natural Product ID:	NPC222572
*Common Name:**	3'-Deoxy-O-Methylsappanol
IUPAC Name:	(3R,4S)-3-[(4-hydroxyphenyl)methyl]-4-methoxy-2,4-dihydrochromene-3,7-diol
Synonyms:
Standard InCHIKey:	NRDMATSOBGRQDO-DLBZAZTESA-N
Standard InCHI:	InChI=1S/C17H18O5/c1-21-16-14-7-6-13(19)8-15(14)22-10-17(16,20)9-11-2-4-12(18)5-3-11/h2-8,16,18-20H,9-10H2,1H3/t16-,17+/m0/s1
SMILES:	CO[C@H]1c2ccc(cc2OC[C@]1(O)Cc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518739
PubChem CID:	13846680
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans

*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]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	6

Activity Type	# Activity
Individual Protein	6

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	=	0.0	%	PMID[476792]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	Inhibition	=	3.1	%	PMID[476792]
NPT1479	Individual Protein	Stem cell growth factor receptor	Homo sapiens	Inhibition	=	19.8	%	PMID[476792]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	Inhibition	=	2.8	%	PMID[476792]
NPT1480	Individual Protein	Fibroblast growth factor receptor 1	Homo sapiens	Inhibition	=	13.8	%	PMID[476792]
NPT1481	Individual Protein	Fibroblast growth factor receptor 2	Homo sapiens	Inhibition	=	0.0	%	PMID[476792]

☑ 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 NPC222572 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	383
0.1-0.2	1497
0.2-0.3	4626
0.3-0.4	12182
0.4-0.5	5847
0.5-0.6	4264
0.6-0.7	6854
0.7-0.8	5561
0.8-0.85	978
0.85-0.9	369
0.9-0.95	126
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC87224
0.96	High Similarity	NPC103799
0.96	High Similarity	NPC162801
0.959	High Similarity	NPC207179
0.959	High Similarity	NPC167571
0.959	High Similarity	NPC278552
0.9587	High Similarity	NPC76465
0.9587	High Similarity	NPC38761
0.9528	High Similarity	NPC117048
0.9528	High Similarity	NPC124085
0.9504	High Similarity	NPC100099
0.9504	High Similarity	NPC36016
0.9453	High Similarity	NPC151224
0.9449	High Similarity	NPC215037
0.9449	High Similarity	NPC85435
0.9449	High Similarity	NPC92805
0.9431	High Similarity	NPC188022
0.9431	High Similarity	NPC103420
0.9431	High Similarity	NPC285040
0.9431	High Similarity	NPC17809
0.9431	High Similarity	NPC102540
0.9421	High Similarity	NPC97432
0.9421	High Similarity	NPC190454
0.938	High Similarity	NPC474639
0.938	High Similarity	NPC262585
0.938	High Similarity	NPC3049
0.938	High Similarity	NPC18189
0.938	High Similarity	NPC230734
0.938	High Similarity	NPC20829
0.938	High Similarity	NPC227503
0.936	High Similarity	NPC274717
0.9355	High Similarity	NPC276212
0.9355	High Similarity	NPC283049
0.9355	High Similarity	NPC26879
0.9355	High Similarity	NPC230479
0.9355	High Similarity	NPC50315
0.935	High Similarity	NPC246648
0.935	High Similarity	NPC86502
0.935	High Similarity	NPC106914
0.935	High Similarity	NPC134195
0.935	High Similarity	NPC197351
0.9308	High Similarity	NPC474687
0.9302	High Similarity	NPC112939
0.9302	High Similarity	NPC61946
0.9302	High Similarity	NPC470356
0.9302	High Similarity	NPC112246
0.9302	High Similarity	NPC474206
0.9302	High Similarity	NPC94750
0.9302	High Similarity	NPC121812
0.9302	High Similarity	NPC164787
0.9297	High Similarity	NPC11060
0.928	High Similarity	NPC149796
0.9268	High Similarity	NPC474160
0.9262	High Similarity	NPC54972
0.9256	High Similarity	NPC258979
0.9256	High Similarity	NPC8283
0.9256	High Similarity	NPC93398
0.9237	High Similarity	NPC475836
0.9231	High Similarity	NPC306441
0.9231	High Similarity	NPC16435
0.9231	High Similarity	NPC269091
0.9231	High Similarity	NPC302701
0.9219	High Similarity	NPC13005
0.9206	High Similarity	NPC39064
0.9206	High Similarity	NPC47283
0.9206	High Similarity	NPC53986
0.9206	High Similarity	NPC38664
0.9174	High Similarity	NPC172253
0.9174	High Similarity	NPC59561
0.916	High Similarity	NPC176051
0.916	High Similarity	NPC262328
0.916	High Similarity	NPC103976
0.916	High Similarity	NPC211549
0.916	High Similarity	NPC87777
0.916	High Similarity	NPC102904
0.916	High Similarity	NPC326797
0.916	High Similarity	NPC474282
0.916	High Similarity	NPC107551
0.9154	High Similarity	NPC234333
0.9154	High Similarity	NPC260898
0.9154	High Similarity	NPC47398
0.9154	High Similarity	NPC473413
0.9147	High Similarity	NPC263064
0.9141	High Similarity	NPC228369
0.9141	High Similarity	NPC68205
0.9141	High Similarity	NPC150011
0.9141	High Similarity	NPC118683
0.9141	High Similarity	NPC12875
0.9141	High Similarity	NPC207892
0.9141	High Similarity	NPC476166
0.9141	High Similarity	NPC236014
0.9141	High Similarity	NPC129784
0.9141	High Similarity	NPC17343
0.9141	High Similarity	NPC129106
0.9141	High Similarity	NPC293203
0.9141	High Similarity	NPC164804
0.9141	High Similarity	NPC280653
0.9141	High Similarity	NPC268917
0.9141	High Similarity	NPC206224
0.9141	High Similarity	NPC244888
0.9141	High Similarity	NPC164574
0.9141	High Similarity	NPC211413
0.9141	High Similarity	NPC118114
0.9141	High Similarity	NPC300875
0.9141	High Similarity	NPC196765
0.9134	High Similarity	NPC134360
0.9134	High Similarity	NPC93962
0.9084	High Similarity	NPC234952
0.9084	High Similarity	NPC265433
0.9084	High Similarity	NPC162659
0.9084	High Similarity	NPC270456
0.9084	High Similarity	NPC470802
0.9084	High Similarity	NPC248727
0.9077	High Similarity	NPC225696
0.9077	High Similarity	NPC198154
0.9077	High Similarity	NPC317380
0.9077	High Similarity	NPC223008
0.9077	High Similarity	NPC115335
0.9077	High Similarity	NPC97834
0.9077	High Similarity	NPC296915
0.907	High Similarity	NPC219876
0.907	High Similarity	NPC127624
0.907	High Similarity	NPC261619
0.907	High Similarity	NPC78770
0.907	High Similarity	NPC126029
0.907	High Similarity	NPC86655
0.907	High Similarity	NPC15658
0.907	High Similarity	NPC202762
0.907	High Similarity	NPC61477
0.907	High Similarity	NPC185604
0.9062	High Similarity	NPC27187
0.9062	High Similarity	NPC470225
0.9048	High Similarity	NPC262573
0.9048	High Similarity	NPC471215
0.9023	High Similarity	NPC309124
0.9023	High Similarity	NPC184797
0.9016	High Similarity	NPC295259
0.9015	High Similarity	NPC276490
0.9008	High Similarity	NPC195022
0.9	High Similarity	NPC229442
0.9	High Similarity	NPC77196
0.9	High Similarity	NPC475840
0.9	High Similarity	NPC168059
0.8992	High Similarity	NPC271945
0.8992	High Similarity	NPC220825
0.8992	High Similarity	NPC268266
0.8992	High Similarity	NPC268342
0.8992	High Similarity	NPC42760
0.8992	High Similarity	NPC181497
0.8963	High Similarity	NPC81638
0.8955	High Similarity	NPC471389
0.8955	High Similarity	NPC210192
0.8952	High Similarity	NPC193364
0.8947	High Similarity	NPC471388
0.8947	High Similarity	NPC473739
0.8947	High Similarity	NPC260741
0.8947	High Similarity	NPC232164
0.8947	High Similarity	NPC127218
0.8947	High Similarity	NPC32630
0.8947	High Similarity	NPC319647
0.8947	High Similarity	NPC25966
0.8947	High Similarity	NPC70682
0.8947	High Similarity	NPC236306
0.8947	High Similarity	NPC245207
0.8939	High Similarity	NPC472336
0.8939	High Similarity	NPC173660
0.8939	High Similarity	NPC472334
0.8934	High Similarity	NPC74821
0.8931	High Similarity	NPC170694
0.8926	High Similarity	NPC229147
0.8926	High Similarity	NPC54507
0.8926	High Similarity	NPC85292
0.8923	High Similarity	NPC201587
0.8923	High Similarity	NPC253105
0.8906	High Similarity	NPC31707
0.8906	High Similarity	NPC226331
0.8906	High Similarity	NPC46274
0.8897	High Similarity	NPC475492
0.8889	High Similarity	NPC84207
0.8889	High Similarity	NPC230718
0.8889	High Similarity	NPC472353
0.8889	High Similarity	NPC139976
0.8889	High Similarity	NPC59841
0.8889	High Similarity	NPC5253
0.8889	High Similarity	NPC204347
0.8889	High Similarity	NPC294156
0.8889	High Similarity	NPC49542
0.8889	High Similarity	NPC256015
0.8889	High Similarity	NPC107161
0.8889	High Similarity	NPC159132
0.8889	High Similarity	NPC128337
0.8889	High Similarity	NPC475891
0.8889	High Similarity	NPC2613
0.8881	High Similarity	NPC27495
0.8881	High Similarity	NPC22317
0.8872	High Similarity	NPC134260
0.8864	High Similarity	NPC472337
0.8846	High Similarity	NPC472597
0.8843	High Similarity	NPC464
0.8843	High Similarity	NPC185541

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 NPC222572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	860
0.2-0.3	1785
0.3-0.4	2672
0.4-0.5	1689
0.5-0.6	958
0.6-0.7	687
0.7-0.8	154
0.8-0.85	13
0.85-0.9	3
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.907	High Similarity	NPD1612	Clinical (unspecified phase)
0.907	High Similarity	NPD1613	Approved
0.9055	High Similarity	NPD4908	Phase 1
0.8952	High Similarity	NPD1610	Phase 2
0.8934	High Similarity	NPD1548	Phase 1
0.8915	High Similarity	NPD4907	Clinical (unspecified phase)
0.8906	High Similarity	NPD1529	Clinical (unspecified phase)
0.8828	High Similarity	NPD1530	Clinical (unspecified phase)
0.8692	High Similarity	NPD3027	Phase 3
0.8409	Intermediate Similarity	NPD4625	Phase 3
0.8397	Intermediate Similarity	NPD2861	Phase 2
0.8372	Intermediate Similarity	NPD4749	Approved
0.8359	Intermediate Similarity	NPD1091	Approved
0.8209	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD7213	Phase 3
0.8169	Intermediate Similarity	NPD7212	Phase 2
0.8162	Intermediate Similarity	NPD5124	Phase 1
0.8162	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1652	Phase 2
0.8129	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD2684	Approved
0.8095	Intermediate Similarity	NPD1934	Approved
0.8077	Intermediate Similarity	NPD422	Phase 1
0.8071	Intermediate Similarity	NPD1549	Phase 2
0.8043	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD4536	Approved
0.8043	Intermediate Similarity	NPD4538	Approved
0.8041	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD290	Approved
0.8014	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7843	Approved
0.7986	Intermediate Similarity	NPD7447	Phase 1
0.7959	Intermediate Similarity	NPD4380	Phase 2
0.7953	Intermediate Similarity	NPD6671	Approved
0.7941	Intermediate Similarity	NPD6798	Discontinued
0.7895	Intermediate Similarity	NPD8651	Approved
0.7881	Intermediate Similarity	NPD7075	Discontinued
0.7881	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5588	Approved
0.7857	Intermediate Similarity	NPD5960	Phase 3
0.7847	Intermediate Similarity	NPD5058	Phase 3
0.7826	Intermediate Similarity	NPD4060	Phase 1
0.7815	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7157	Approved
0.7805	Intermediate Similarity	NPD968	Approved
0.78	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD5846	Approved
0.7786	Intermediate Similarity	NPD6516	Phase 2
0.7785	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD940	Approved
0.7769	Intermediate Similarity	NPD846	Approved
0.7754	Intermediate Similarity	NPD6233	Phase 2
0.773	Intermediate Similarity	NPD7033	Discontinued
0.7721	Intermediate Similarity	NPD3018	Phase 2
0.7703	Intermediate Similarity	NPD1653	Approved
0.7692	Intermediate Similarity	NPD6166	Phase 2
0.7692	Intermediate Similarity	NPD2424	Discontinued
0.7692	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6582	Phase 2
0.7687	Intermediate Similarity	NPD6583	Phase 3
0.7682	Intermediate Similarity	NPD2801	Approved
0.7676	Intermediate Similarity	NPD6099	Approved
0.7676	Intermediate Similarity	NPD6100	Approved
0.7676	Intermediate Similarity	NPD2796	Approved
0.7671	Intermediate Similarity	NPD6799	Approved
0.766	Intermediate Similarity	NPD7097	Phase 1
0.7643	Intermediate Similarity	NPD6355	Discontinued
0.7632	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6801	Discontinued
0.7606	Intermediate Similarity	NPD1510	Phase 2
0.7586	Intermediate Similarity	NPD7466	Approved
0.7586	Intermediate Similarity	NPD3750	Approved
0.7578	Intermediate Similarity	NPD5535	Approved
0.7571	Intermediate Similarity	NPD1240	Approved
0.7556	Intermediate Similarity	NPD2983	Phase 2
0.7556	Intermediate Similarity	NPD2982	Phase 2
0.7551	Intermediate Similarity	NPD1511	Approved
0.755	Intermediate Similarity	NPD7411	Suspended
0.7547	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6584	Phase 3
0.7518	Intermediate Similarity	NPD4340	Discontinued
0.7517	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD7074	Phase 3
0.7483	Intermediate Similarity	NPD6599	Discontinued
0.7482	Intermediate Similarity	NPD7095	Approved
0.7481	Intermediate Similarity	NPD2981	Phase 2
0.7468	Intermediate Similarity	NPD3882	Suspended
0.7466	Intermediate Similarity	NPD4535	Phase 3
0.7466	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4628	Phase 3
0.7465	Intermediate Similarity	NPD1607	Approved
0.745	Intermediate Similarity	NPD1512	Approved
0.7447	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD2797	Approved
0.7438	Intermediate Similarity	NPD7054	Approved
0.7434	Intermediate Similarity	NPD6072	Discontinued
0.7426	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6559	Discontinued
0.7403	Intermediate Similarity	NPD3817	Phase 2
0.7397	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6674	Discontinued
0.7391	Intermediate Similarity	NPD7472	Approved
0.7385	Intermediate Similarity	NPD5283	Phase 1
0.7383	Intermediate Similarity	NPD5401	Approved
0.7376	Intermediate Similarity	NPD4062	Phase 3
0.7375	Intermediate Similarity	NPD3818	Discontinued
0.7372	Intermediate Similarity	NPD3225	Approved
0.7372	Intermediate Similarity	NPD6234	Discontinued
0.7364	Intermediate Similarity	NPD228	Approved
0.7355	Intermediate Similarity	NPD2859	Approved
0.7355	Intermediate Similarity	NPD2860	Approved
0.7355	Intermediate Similarity	NPD7768	Phase 2
0.7347	Intermediate Similarity	NPD3892	Phase 2
0.7346	Intermediate Similarity	NPD6797	Phase 2
0.7344	Intermediate Similarity	NPD5451	Approved
0.7338	Intermediate Similarity	NPD7819	Suspended
0.7338	Intermediate Similarity	NPD8455	Phase 2
0.7329	Intermediate Similarity	NPD5844	Phase 1
0.7324	Intermediate Similarity	NPD2238	Phase 2
0.731	Intermediate Similarity	NPD1551	Phase 2
0.7308	Intermediate Similarity	NPD821	Approved
0.7305	Intermediate Similarity	NPD3268	Approved
0.7303	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7251	Discontinued
0.7297	Intermediate Similarity	NPD2677	Approved
0.7292	Intermediate Similarity	NPD2200	Suspended
0.729	Intermediate Similarity	NPD5402	Approved
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7278	Intermediate Similarity	NPD6959	Discontinued
0.7273	Intermediate Similarity	NPD5735	Approved
0.7273	Intermediate Similarity	NPD2557	Approved
0.7273	Intermediate Similarity	NPD2933	Approved
0.7273	Intermediate Similarity	NPD2934	Approved
0.7273	Intermediate Similarity	NPD37	Approved
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7266	Discontinued
0.726	Intermediate Similarity	NPD5762	Approved
0.726	Intermediate Similarity	NPD5763	Approved
0.726	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1242	Phase 1
0.7256	Intermediate Similarity	NPD7808	Phase 3
0.7255	Intermediate Similarity	NPD4678	Approved
0.7255	Intermediate Similarity	NPD4675	Approved
0.7248	Intermediate Similarity	NPD3122	Phase 3
0.7246	Intermediate Similarity	NPD6696	Suspended
0.7244	Intermediate Similarity	NPD4965	Approved
0.7244	Intermediate Similarity	NPD4967	Phase 2
0.7244	Intermediate Similarity	NPD4966	Approved
0.7241	Intermediate Similarity	NPD3748	Approved
0.7239	Intermediate Similarity	NPD6581	Approved
0.7239	Intermediate Similarity	NPD6580	Approved
0.7239	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3179	Approved
0.7234	Intermediate Similarity	NPD3180	Approved
0.7233	Intermediate Similarity	NPD3787	Discontinued
0.7222	Intermediate Similarity	NPD3052	Approved
0.7222	Intermediate Similarity	NPD3054	Approved
0.7218	Intermediate Similarity	NPD3596	Phase 2
0.7215	Intermediate Similarity	NPD5494	Approved
0.7209	Intermediate Similarity	NPD4750	Phase 3
0.7206	Intermediate Similarity	NPD3496	Discontinued
0.7203	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1558	Phase 1
0.7197	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6032	Approved
0.7188	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3020	Approved
0.7174	Intermediate Similarity	NPD3685	Discontinued
0.7174	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5061	Approved
0.7162	Intermediate Similarity	NPD5062	Approved
0.7162	Intermediate Similarity	NPD5177	Phase 3
0.7161	Intermediate Similarity	NPD4433	Discontinued
0.716	Intermediate Similarity	NPD7228	Approved
0.7153	Intermediate Similarity	NPD1535	Discovery
0.7152	Intermediate Similarity	NPD3536	Discontinued
0.7152	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD3690	Phase 2
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3540	Phase 1
0.7143	Intermediate Similarity	NPD3691	Phase 2
0.7133	Intermediate Similarity	NPD7477	Discontinued
0.7132	Intermediate Similarity	NPD5125	Phase 3
0.7132	Intermediate Similarity	NPD5126	Approved
0.7123	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5929	Approved
0.7115	Intermediate Similarity	NPD1465	Phase 2
0.7111	Intermediate Similarity	NPD1894	Discontinued
0.7105	Intermediate Similarity	NPD7314	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