NPASS Compound

Structure

CID117048 OpenBabel06191715472D 31 34 0 0 1 0 0 0 0 0999 V2000 -2.5214 -4.5059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7593 -4.5064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8906 -2.7415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4248 -3.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3238 0.1006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6400 -2.9802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2496 -1.7546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5209 -2.4713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6798 -0.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6804 1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5200 1.4547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6807 -0.9693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3600 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6801 1.9404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6402 -3.9975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8550 -2.6404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5206 -1.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6800 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6805 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8400 1.4550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3602 -0.9689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5198 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5201 0.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 0.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8401 0.4851 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8399 1.4553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2414 -1.4773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8397 2.4553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3595 -0.0006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5199 1.4557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 29 1 0 0 0 0 6 8 1 0 0 0 0 6 15 2 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 2 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 21 2 0 0 0 0 13 23 1 0 0 0 0 14 26 1 0 0 0 0 14 30 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 25 26 1 1 0 0 0 25 31 1 0 0 0 0 26 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.21
Volume:	446.886
LogP:	6.704
LogD:	4.201
LogS:	-4.028
# Rotatable Bonds:	5
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.654
Synthetic Accessibility Score:	3.998
Fsp3:	0.385
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.749
MDCK Permeability:	1.5421295756823383e-05
Pgp-inhibitor:	0.899
Pgp-substrate:	0.833
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.867
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	84.6327133178711%
Volume Distribution (VD):	4.369
Pgp-substrate:	14.64578914642334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.525
CYP1A2-substrate:	0.476
CYP2C19-inhibitor:	0.929
CYP2C19-substrate:	0.666
CYP2C9-inhibitor:	0.841
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.648
CYP2D6-substrate:	0.85
CYP3A4-inhibitor:	0.705
CYP3A4-substrate:	0.548

ADMET: Excretion

Clearance (CL):	14.979
Half-life (T1/2):	0.051

ADMET: Toxicity

hERG Blockers:	0.249
Human Hepatotoxicity (H-HT):	0.828
Drug-inuced Liver Injury (DILI):	0.164
AMES Toxicity:	0.315
Rat Oral Acute Toxicity:	0.732
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.34
Carcinogencity:	0.249
Eye Corrosion:	0.003
Eye Irritation:	0.485
Respiratory Toxicity:	0.865

Download Data

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

Natural Product: NPC117048

Natural Product ID:	NPC117048
*Common Name:**	Erystagallin A
IUPAC Name:	(6aS,11aS)-9-methoxy-2,10-bis(3-methylbut-2-enyl)-6,11a-dihydro-[1]benzofuro[3,2-c]chromene-3,6a-diol
Synonyms:
Standard InCHIKey:	OOAXWUFECWLVEQ-IZZNHLLZSA-N
Standard InCHI:	InChI=1S/C26H30O5/c1-15(2)6-8-17-12-19-23(13-21(17)27)30-14-26(28)20-10-11-22(29-5)18(9-7-16(3)4)24(20)31-25(19)26/h6-7,10-13,25,27-28H,8-9,14H2,1-5H3/t25-,26+/m0/s1
SMILES:	COc1ccc2c(c1CC=C(C)C)O[C@@H]1[C@@]2(O)COc2c1cc(CC=C(C)C)c(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088462
PubChem CID:	10410005
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13146	Pertusaria albescens	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16356	Crocynia membranacea	Species	Crocyniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14662	Lomatia longifolia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5160	Pandanus veitchi	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17390	Dysidea robusta	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16070	Indigofera oblongifolia	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	7
Ki	1
Others	2

Activity Type	# Activity
Cell Line	4
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	20800.0	nM	PMID[453601]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	30000.0	nM	PMID[453601]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	30000.0	nM	PMID[453601]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	2040.0	nM	PMID[453602]
NPT345	Individual Protein	Sialidase	Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)	IC50	=	27740.0	nM	PMID[453602]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	1800.0	nM	PMID[453602]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Inhibition	=	91.0	%	PMID[453602]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Inhibition	=	9.0	%	PMID[453602]

☑ 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 NPC117048 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	395
0.1-0.2	1441
0.2-0.3	3848
0.3-0.4	11124
0.4-0.5	7598
0.5-0.6	3902
0.6-0.7	7288
0.7-0.8	5598
0.8-0.85	1084
0.85-0.9	271
0.9-0.95	112
0.95-1	36

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC124085
0.9921	High Similarity	NPC85435
0.9845	High Similarity	NPC262585
0.9845	High Similarity	NPC3049
0.9845	High Similarity	NPC18189
0.9845	High Similarity	NPC20829
0.9769	High Similarity	NPC474687
0.9764	High Similarity	NPC162801
0.9695	High Similarity	NPC475836
0.9688	High Similarity	NPC13005
0.9612	High Similarity	NPC92805
0.9609	High Similarity	NPC118114
0.9609	High Similarity	NPC228369
0.9609	High Similarity	NPC196765
0.9609	High Similarity	NPC129106
0.9609	High Similarity	NPC476166
0.9609	High Similarity	NPC206224
0.9609	High Similarity	NPC17343
0.9609	High Similarity	NPC280653
0.9609	High Similarity	NPC236014
0.9609	High Similarity	NPC12875
0.9609	High Similarity	NPC150011
0.9609	High Similarity	NPC129784
0.9609	High Similarity	NPC103799
0.9609	High Similarity	NPC207892
0.9609	High Similarity	NPC300875
0.9609	High Similarity	NPC268917
0.9609	High Similarity	NPC164574
0.9538	High Similarity	NPC115335
0.9538	High Similarity	NPC97834
0.9538	High Similarity	NPC225696
0.9538	High Similarity	NPC296915
0.9538	High Similarity	NPC198154
0.9538	High Similarity	NPC223008
0.9531	High Similarity	NPC27187
0.9531	High Similarity	NPC470225
0.9528	High Similarity	NPC222572
0.9528	High Similarity	NPC87224
0.9457	High Similarity	NPC271945
0.9457	High Similarity	NPC181497
0.9375	High Similarity	NPC274717
0.9375	High Similarity	NPC47283
0.9375	High Similarity	NPC38664
0.9375	High Similarity	NPC39064
0.9375	High Similarity	NPC53986
0.9313	High Similarity	NPC215037
0.9308	High Similarity	NPC68205
0.9308	High Similarity	NPC244888
0.9308	High Similarity	NPC211413
0.9308	High Similarity	NPC118683
0.9308	High Similarity	NPC164804
0.9308	High Similarity	NPC293203
0.9302	High Similarity	NPC93962
0.9291	High Similarity	NPC188022
0.9291	High Similarity	NPC102540
0.9291	High Similarity	NPC17809
0.9291	High Similarity	NPC285040
0.9291	High Similarity	NPC103420
0.9219	High Similarity	NPC26879
0.9219	High Similarity	NPC276212
0.9219	High Similarity	NPC262573
0.9219	High Similarity	NPC471215
0.9219	High Similarity	NPC283049
0.9219	High Similarity	NPC230479
0.9219	High Similarity	NPC50315
0.9213	High Similarity	NPC197351
0.9213	High Similarity	NPC86502
0.9213	High Similarity	NPC134195
0.9213	High Similarity	NPC106914
0.9213	High Similarity	NPC246648
0.9197	High Similarity	NPC12641
0.9197	High Similarity	NPC93323
0.9197	High Similarity	NPC45257
0.9197	High Similarity	NPC280092
0.9185	High Similarity	NPC309124
0.9185	High Similarity	NPC184797
0.9173	High Similarity	NPC151224
0.9173	High Similarity	NPC473413
0.9167	High Similarity	NPC77196
0.9154	High Similarity	NPC134360
0.9147	High Similarity	NPC149796
0.9141	High Similarity	NPC278552
0.9141	High Similarity	NPC207179
0.9141	High Similarity	NPC167571
0.9137	High Similarity	NPC21776
0.9137	High Similarity	NPC16269
0.9134	High Similarity	NPC76465
0.9134	High Similarity	NPC38761
0.913	High Similarity	NPC469557
0.9124	High Similarity	NPC102044
0.9124	High Similarity	NPC47633
0.9124	High Similarity	NPC85264
0.9118	High Similarity	NPC87725
0.9118	High Similarity	NPC5155
0.9118	High Similarity	NPC263261
0.9111	High Similarity	NPC236306
0.9111	High Similarity	NPC260741
0.9111	High Similarity	NPC473739
0.9111	High Similarity	NPC232164
0.9111	High Similarity	NPC32630
0.9111	High Similarity	NPC70682
0.9104	High Similarity	NPC470802
0.9104	High Similarity	NPC227503
0.9104	High Similarity	NPC230734
0.9104	High Similarity	NPC474639
0.9104	High Similarity	NPC126101
0.9062	High Similarity	NPC256015
0.9062	High Similarity	NPC294156
0.9058	High Similarity	NPC63879
0.9058	High Similarity	NPC475492
0.9055	High Similarity	NPC36016
0.9055	High Similarity	NPC100099
0.9051	High Similarity	NPC59841
0.9051	High Similarity	NPC475891
0.9051	High Similarity	NPC2613
0.9051	High Similarity	NPC472353
0.9051	High Similarity	NPC204347
0.9051	High Similarity	NPC107161
0.9044	High Similarity	NPC27495
0.9037	High Similarity	NPC477938
0.903	High Similarity	NPC112939
0.903	High Similarity	NPC474206
0.903	High Similarity	NPC112246
0.903	High Similarity	NPC470356
0.903	High Similarity	NPC164787
0.903	High Similarity	NPC61946
0.903	High Similarity	NPC94750
0.903	High Similarity	NPC121812
0.9023	High Similarity	NPC11060
0.9	High Similarity	NPC101376
0.8992	High Similarity	NPC81641
0.8986	High Similarity	NPC81638
0.8984	High Similarity	NPC474160
0.8978	High Similarity	NPC265075
0.8978	High Similarity	NPC35216
0.8978	High Similarity	NPC100482
0.8978	High Similarity	NPC277331
0.8978	High Similarity	NPC247291
0.8976	High Similarity	NPC97432
0.8976	High Similarity	NPC190454
0.8963	High Similarity	NPC16435
0.8963	High Similarity	NPC269091
0.8963	High Similarity	NPC265433
0.8963	High Similarity	NPC270456
0.8963	High Similarity	NPC248727
0.8963	High Similarity	NPC234952
0.8963	High Similarity	NPC162659
0.8963	High Similarity	NPC302701
0.8963	High Similarity	NPC306441
0.8963	High Similarity	NPC327735
0.8955	High Similarity	NPC473107
0.8929	High Similarity	NPC233980
0.8929	High Similarity	NPC260397
0.8921	High Similarity	NPC50250
0.8921	High Similarity	NPC473108
0.8906	High Similarity	NPC150026
0.8905	High Similarity	NPC160283
0.8905	High Similarity	NPC254759
0.8905	High Similarity	NPC259519
0.8897	High Similarity	NPC102904
0.8897	High Similarity	NPC326797
0.8897	High Similarity	NPC107551
0.8897	High Similarity	NPC176051
0.8897	High Similarity	NPC211549
0.8897	High Similarity	NPC474282
0.8897	High Similarity	NPC103976
0.8889	High Similarity	NPC125579
0.8889	High Similarity	NPC234333
0.8889	High Similarity	NPC260898
0.8889	High Similarity	NPC47398
0.8881	High Similarity	NPC263064
0.8865	High Similarity	NPC474397
0.8857	High Similarity	NPC181615
0.8849	High Similarity	NPC184607
0.8849	High Similarity	NPC474104
0.8841	High Similarity	NPC471389
0.8841	High Similarity	NPC108674
0.8832	High Similarity	NPC25966
0.8832	High Similarity	NPC319647
0.8832	High Similarity	NPC471388
0.8832	High Similarity	NPC292882
0.8832	High Similarity	NPC245207
0.8832	High Similarity	NPC127218
0.8828	High Similarity	NPC54972
0.8828	High Similarity	NPC193364
0.8824	High Similarity	NPC54743
0.8824	High Similarity	NPC29799
0.8824	High Similarity	NPC78047
0.8824	High Similarity	NPC471522
0.8824	High Similarity	NPC156502
0.8824	High Similarity	NPC263367
0.8824	High Similarity	NPC472800
0.8824	High Similarity	NPC177160
0.8824	High Similarity	NPC173660
0.8824	High Similarity	NPC209985
0.8824	High Similarity	NPC10737
0.8824	High Similarity	NPC477939
0.8819	High Similarity	NPC93398
0.8819	High Similarity	NPC160196
0.8819	High Similarity	NPC258979

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 NPC117048 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	856
0.2-0.3	1671
0.3-0.4	2689
0.4-0.5	1774
0.5-0.6	987
0.6-0.7	685
0.7-0.8	144
0.8-0.85	5
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9084	High Similarity	NPD4907	Clinical (unspecified phase)
0.8931	High Similarity	NPD4908	Phase 1
0.8828	High Similarity	NPD1610	Phase 2
0.8806	High Similarity	NPD1613	Approved
0.8806	High Similarity	NPD1612	Clinical (unspecified phase)
0.8647	High Similarity	NPD1529	Clinical (unspecified phase)
0.8582	High Similarity	NPD4625	Phase 3
0.8571	High Similarity	NPD1530	Clinical (unspecified phase)
0.8516	High Similarity	NPD1548	Phase 1
0.8444	Intermediate Similarity	NPD3027	Phase 3
0.8433	Intermediate Similarity	NPD2861	Phase 2
0.8271	Intermediate Similarity	NPD4749	Approved
0.8248	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD5588	Approved
0.8138	Intermediate Similarity	NPD5058	Phase 3
0.8085	Intermediate Similarity	NPD4536	Approved
0.8085	Intermediate Similarity	NPD4538	Approved
0.8085	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD8651	Approved
0.8071	Intermediate Similarity	NPD5124	Phase 1
0.8071	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD4060	Phase 1
0.7985	Intermediate Similarity	NPD1091	Approved
0.7922	Intermediate Similarity	NPD7075	Discontinued
0.7905	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD5960	Phase 3
0.7895	Intermediate Similarity	NPD1934	Approved
0.7862	Intermediate Similarity	NPD2424	Discontinued
0.7857	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7212	Phase 2
0.7838	Intermediate Similarity	NPD7213	Phase 3
0.7808	Intermediate Similarity	NPD1652	Phase 2
0.7793	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7447	Phase 1
0.7755	Intermediate Similarity	NPD7466	Approved
0.774	Intermediate Similarity	NPD1549	Phase 2
0.7734	Intermediate Similarity	NPD2684	Approved
0.7727	Intermediate Similarity	NPD6671	Approved
0.7727	Intermediate Similarity	NPD7157	Approved
0.7721	Intermediate Similarity	NPD422	Phase 1
0.7712	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6355	Discontinued
0.7692	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD6696	Suspended
0.7669	Intermediate Similarity	NPD6559	Discontinued
0.7656	Intermediate Similarity	NPD290	Approved
0.7643	Intermediate Similarity	NPD6234	Discontinued
0.7634	Intermediate Similarity	NPD7843	Approved
0.7628	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6798	Discontinued
0.7603	Intermediate Similarity	NPD6099	Approved
0.7603	Intermediate Similarity	NPD6100	Approved
0.7597	Intermediate Similarity	NPD6072	Discontinued
0.7595	Intermediate Similarity	NPD5494	Approved
0.7593	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5125	Phase 3
0.7574	Intermediate Similarity	NPD5126	Approved
0.7571	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6674	Discontinued
0.755	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6801	Discontinued
0.7548	Intermediate Similarity	NPD37	Approved
0.7534	Intermediate Similarity	NPD7033	Discontinued
0.7518	Intermediate Similarity	NPD3018	Phase 2
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4535	Phase 3
0.7517	Intermediate Similarity	NPD3750	Approved
0.7516	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4966	Approved
0.7516	Intermediate Similarity	NPD6166	Phase 2
0.7516	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD1653	Approved
0.7516	Intermediate Similarity	NPD3882	Suspended
0.7516	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7768	Phase 2
0.7516	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7484	Intermediate Similarity	NPD7411	Suspended
0.7483	Intermediate Similarity	NPD2796	Approved
0.7466	Intermediate Similarity	NPD7097	Phase 1
0.7448	Intermediate Similarity	NPD5735	Approved
0.7445	Intermediate Similarity	NPD6516	Phase 2
0.7445	Intermediate Similarity	NPD5846	Approved
0.7442	Intermediate Similarity	NPD968	Approved
0.7438	Intermediate Similarity	NPD7199	Phase 2
0.7438	Intermediate Similarity	NPD6959	Discontinued
0.7432	Intermediate Similarity	NPD6002	Phase 3
0.7432	Intermediate Similarity	NPD6004	Phase 3
0.7432	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5763	Approved
0.7432	Intermediate Similarity	NPD5762	Approved
0.7432	Intermediate Similarity	NPD6005	Phase 3
0.7432	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6233	Phase 2
0.7423	Intermediate Similarity	NPD7228	Approved
0.7423	Intermediate Similarity	NPD3818	Discontinued
0.7415	Intermediate Similarity	NPD1510	Phase 2
0.7413	Intermediate Similarity	NPD7095	Approved
0.7402	Intermediate Similarity	NPD846	Approved
0.7402	Intermediate Similarity	NPD940	Approved
0.74	Intermediate Similarity	NPD3892	Phase 2
0.74	Intermediate Similarity	NPD4628	Phase 3
0.7391	Intermediate Similarity	NPD7229	Phase 3
0.7389	Intermediate Similarity	NPD5929	Approved
0.7379	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6799	Approved
0.7368	Intermediate Similarity	NPD1511	Approved
0.7357	Intermediate Similarity	NPD2983	Phase 2
0.7357	Intermediate Similarity	NPD6582	Phase 2
0.7357	Intermediate Similarity	NPD2982	Phase 2
0.7357	Intermediate Similarity	NPD6583	Phase 3
0.7346	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD2800	Approved
0.7324	Intermediate Similarity	NPD6584	Phase 3
0.732	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5283	Phase 1
0.7308	Intermediate Similarity	NPD6599	Discontinued
0.7301	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD2981	Phase 2
0.7273	Intermediate Similarity	NPD7054	Approved
0.7273	Intermediate Similarity	NPD1512	Approved
0.726	Intermediate Similarity	NPD2238	Phase 2
0.726	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3620	Phase 2
0.726	Intermediate Similarity	NPD1240	Approved
0.7254	Intermediate Similarity	NPD2797	Approved
0.725	Intermediate Similarity	NPD3749	Approved
0.7239	Intermediate Similarity	NPD5535	Approved
0.7237	Intermediate Similarity	NPD2677	Approved
0.7234	Intermediate Similarity	NPD5327	Phase 3
0.7233	Intermediate Similarity	NPD3817	Phase 2
0.7229	Intermediate Similarity	NPD7472	Approved
0.7226	Intermediate Similarity	NPD5403	Approved
0.7215	Intermediate Similarity	NPD4433	Discontinued
0.7214	Intermediate Similarity	NPD3705	Approved
0.7211	Intermediate Similarity	NPD4340	Discontinued
0.7208	Intermediate Similarity	NPD2533	Approved
0.7208	Intermediate Similarity	NPD2532	Approved
0.7208	Intermediate Similarity	NPD2534	Approved
0.7203	Intermediate Similarity	NPD3691	Phase 2
0.7203	Intermediate Similarity	NPD3690	Phase 2
0.72	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6667	Approved
0.719	Intermediate Similarity	NPD3122	Phase 3
0.719	Intermediate Similarity	NPD6666	Approved
0.7186	Intermediate Similarity	NPD6797	Phase 2
0.7185	Intermediate Similarity	NPD1398	Phase 1
0.7181	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3748	Approved
0.7178	Intermediate Similarity	NPD3787	Discontinued
0.7178	Intermediate Similarity	NPD6232	Discontinued
0.7174	Intermediate Similarity	NPD7741	Discontinued
0.7171	Intermediate Similarity	NPD6331	Phase 2
0.7164	Intermediate Similarity	NPD228	Approved
0.7162	Intermediate Similarity	NPD6353	Approved
0.7162	Intermediate Similarity	NPD4097	Suspended
0.7162	Intermediate Similarity	NPD1607	Approved
0.7153	Intermediate Similarity	NPD7340	Approved
0.7143	Intermediate Similarity	NPD4750	Phase 3
0.7143	Intermediate Similarity	NPD7041	Phase 2
0.7143	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7251	Discontinued
0.7134	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1551	Phase 2
0.7133	Intermediate Similarity	NPD3094	Phase 2
0.7133	Intermediate Similarity	NPD2935	Discontinued
0.7125	Intermediate Similarity	NPD5402	Approved
0.7125	Intermediate Similarity	NPD2415	Discontinued
0.7125	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3268	Approved
0.7114	Intermediate Similarity	NPD2200	Suspended
0.7109	Intermediate Similarity	NPD3020	Approved
0.7101	Intermediate Similarity	NPD7808	Phase 3
0.7101	Intermediate Similarity	NPD7549	Discontinued
0.7101	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5401	Approved
0.7093	Intermediate Similarity	NPD7906	Approved
0.7089	Intermediate Similarity	NPD4675	Approved
0.7089	Intermediate Similarity	NPD4678	Approved
0.7086	Intermediate Similarity	NPD7266	Discontinued
0.7083	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4062	Phase 3
0.7071	Intermediate Similarity	NPD4626	Approved
0.7063	Intermediate Similarity	NPD1465	Phase 2
0.7063	Intermediate Similarity	NPD3225	Approved
0.7059	Intermediate Similarity	NPD4577	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