NPASS Compound

Structure

CID164912 OpenBabel06191715532D 24 26 0 0 0 0 0 0 0 0999 V2000 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 4.3301 0.5000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 2.5981 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 17 2 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	325.865
LogP:	2.679
LogD:	2.471
LogS:	-4.971
# Rotatable Bonds:	4
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	2.465
Fsp3:	0.222
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:	-4.819
MDCK Permeability:	2.1218864276306704e-05
Pgp-inhibitor:	0.533
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.797

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.224
Plasma Protein Binding (PPB):	94.66246795654297%
Volume Distribution (VD):	0.498
Pgp-substrate:	5.714331150054932%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.18
CYP2C9-inhibitor:	0.578
CYP2C9-substrate:	0.659
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.354
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.448

ADMET: Excretion

Clearance (CL):	7.757
Half-life (T1/2):	0.108

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.877
AMES Toxicity:	0.848
Rat Oral Acute Toxicity:	0.427
Maximum Recommended Daily Dose:	0.085
Skin Sensitization:	0.108
Carcinogencity:	0.946
Eye Corrosion:	0.003
Eye Irritation:	0.882
Respiratory Toxicity:	0.147

Download Data

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

Natural Product: NPC164912

Natural Product ID:	NPC164912
*Common Name:**	6-Hydroxy-1,5-Dimethoxy-2-(Methoxymethyl)Anthraquinone
IUPAC Name:	2-hydroxy-1,5-dimethoxy-6-(methoxymethyl)anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	HEVJQUHAJKODII-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-22-8-9-4-5-10-13(17(9)23-2)15(20)11-6-7-12(19)18(24-3)14(11)16(10)21/h4-7,19H,8H2,1-3H3
SMILES:	COCc1ccc2c(c1OC)C(=O)c1c(C2=O)c(OC)c(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227461
PubChem CID:	16203753
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	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
Others	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[463312]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	10.1	%	PMID[463312]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	100.0	%	PMID[463312]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	75.6	%	PMID[463312]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	29.4	%	PMID[463312]

☑ 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 NPC164912 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	397
0.1-0.2	1732
0.2-0.3	4019
0.3-0.4	10574
0.4-0.5	7543
0.5-0.6	3385
0.6-0.7	5884
0.7-0.8	6904
0.8-0.85	1895
0.85-0.9	325
0.9-0.95	31
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC118427
0.9527	High Similarity	NPC144283
0.9527	High Similarity	NPC473201
0.9527	High Similarity	NPC302783
0.9517	High Similarity	NPC160777
0.9517	High Similarity	NPC73416
0.947	High Similarity	NPC178976
0.947	High Similarity	NPC199463
0.947	High Similarity	NPC37543
0.9404	High Similarity	NPC77807
0.9404	High Similarity	NPC5379
0.9404	High Similarity	NPC14561
0.9404	High Similarity	NPC279605
0.9333	High Similarity	NPC312338
0.9333	High Similarity	NPC149889
0.9286	High Similarity	NPC311740
0.9272	High Similarity	NPC107109
0.9252	High Similarity	NPC478019
0.9231	High Similarity	NPC26386
0.9221	High Similarity	NPC84571
0.9178	High Similarity	NPC192597
0.9178	High Similarity	NPC169214
0.9178	High Similarity	NPC229218
0.9178	High Similarity	NPC141817
0.9178	High Similarity	NPC176030
0.915	High Similarity	NPC213401
0.9145	High Similarity	NPC93552
0.911	High Similarity	NPC84273
0.9103	High Similarity	NPC223336
0.9079	High Similarity	NPC137125
0.9079	High Similarity	NPC3744
0.906	High Similarity	NPC39361
0.9054	High Similarity	NPC309169
0.9054	High Similarity	NPC196941
0.9048	High Similarity	NPC11314
0.902	High Similarity	NPC474000
0.902	High Similarity	NPC475770
0.9013	High Similarity	NPC75377
0.9013	High Similarity	NPC256406
0.9013	High Similarity	NPC306011
0.9013	High Similarity	NPC472838
0.9013	High Similarity	NPC70320
0.9013	High Similarity	NPC78505
0.9	High Similarity	NPC52692
0.9	High Similarity	NPC58373
0.8987	High Similarity	NPC303174
0.8947	High Similarity	NPC470568
0.8947	High Similarity	NPC58310
0.8947	High Similarity	NPC255641
0.8947	High Similarity	NPC85131
0.8947	High Similarity	NPC290954
0.8947	High Similarity	NPC295977
0.8947	High Similarity	NPC472279
0.8947	High Similarity	NPC280295
0.8926	High Similarity	NPC300603
0.8926	High Similarity	NPC91694
0.8924	High Similarity	NPC101769
0.891	High Similarity	NPC104876
0.891	High Similarity	NPC245891
0.8889	High Similarity	NPC470569
0.8882	High Similarity	NPC134293
0.8882	High Similarity	NPC40290
0.8882	High Similarity	NPC264289
0.8882	High Similarity	NPC69430
0.8882	High Similarity	NPC139293
0.8882	High Similarity	NPC195763
0.8882	High Similarity	NPC37220
0.8882	High Similarity	NPC264550
0.8882	High Similarity	NPC142876
0.8882	High Similarity	NPC200060
0.8882	High Similarity	NPC171916
0.8882	High Similarity	NPC333691
0.8882	High Similarity	NPC38545
0.8874	High Similarity	NPC56433
0.8874	High Similarity	NPC312929
0.8874	High Similarity	NPC126767
0.8874	High Similarity	NPC190648
0.8874	High Similarity	NPC289042
0.8874	High Similarity	NPC118027
0.8874	High Similarity	NPC245584
0.8854	High Similarity	NPC36217
0.8854	High Similarity	NPC185617
0.8846	High Similarity	NPC222689
0.8846	High Similarity	NPC136674
0.8846	High Similarity	NPC35598
0.8839	High Similarity	NPC134287
0.8839	High Similarity	NPC117992
0.8839	High Similarity	NPC230149
0.8839	High Similarity	NPC152951
0.8839	High Similarity	NPC168247
0.8839	High Similarity	NPC57674
0.8839	High Similarity	NPC39184
0.8839	High Similarity	NPC130589
0.8831	High Similarity	NPC40356
0.8831	High Similarity	NPC154683
0.8831	High Similarity	NPC474993
0.8828	High Similarity	NPC258502
0.8827	High Similarity	NPC158226
0.8824	High Similarity	NPC147735
0.882	High Similarity	NPC163130
0.882	High Similarity	NPC165979
0.8816	High Similarity	NPC254702
0.8816	High Similarity	NPC139364
0.8816	High Similarity	NPC55327
0.8816	High Similarity	NPC203747
0.8816	High Similarity	NPC203077
0.8816	High Similarity	NPC166036
0.8816	High Similarity	NPC194653
0.8816	High Similarity	NPC80710
0.8816	High Similarity	NPC238279
0.8812	High Similarity	NPC43319
0.8808	High Similarity	NPC300540
0.8805	High Similarity	NPC270837
0.8805	High Similarity	NPC236132
0.88	High Similarity	NPC142165
0.88	High Similarity	NPC21599
0.88	High Similarity	NPC193703
0.8792	High Similarity	NPC69755
0.879	High Similarity	NPC85121
0.879	High Similarity	NPC235448
0.879	High Similarity	NPC477410
0.8782	High Similarity	NPC472455
0.8776	High Similarity	NPC61398
0.8776	High Similarity	NPC416
0.8774	High Similarity	NPC33051
0.8774	High Similarity	NPC124714
0.8774	High Similarity	NPC273462
0.8774	High Similarity	NPC227337
0.8774	High Similarity	NPC70433
0.8774	High Similarity	NPC208806
0.8774	High Similarity	NPC49402
0.8774	High Similarity	NPC472905
0.8774	High Similarity	NPC127172
0.8773	High Similarity	NPC199357
0.8767	High Similarity	NPC324929
0.8758	High Similarity	NPC218226
0.8758	High Similarity	NPC234331
0.8758	High Similarity	NPC261322
0.875	High Similarity	NPC125449
0.875	High Similarity	NPC188074
0.8742	High Similarity	NPC201800
0.8742	High Similarity	NPC34482
0.8742	High Similarity	NPC49282
0.8742	High Similarity	NPC294965
0.8742	High Similarity	NPC157133
0.8742	High Similarity	NPC225351
0.8734	High Similarity	NPC472902
0.8734	High Similarity	NPC228785
0.8734	High Similarity	NPC155302
0.8734	High Similarity	NPC474960
0.8734	High Similarity	NPC471973
0.8734	High Similarity	NPC161947
0.8734	High Similarity	NPC56085
0.8734	High Similarity	NPC14353
0.8733	High Similarity	NPC50954
0.8733	High Similarity	NPC46161
0.8733	High Similarity	NPC254659
0.8733	High Similarity	NPC66593
0.8733	High Similarity	NPC239608
0.8733	High Similarity	NPC53016
0.8726	High Similarity	NPC291508
0.8726	High Similarity	NPC304008
0.8726	High Similarity	NPC472963
0.8726	High Similarity	NPC78103
0.8726	High Similarity	NPC299520
0.8726	High Similarity	NPC219867
0.8726	High Similarity	NPC161960
0.8726	High Similarity	NPC129684
0.8726	High Similarity	NPC187745
0.8726	High Similarity	NPC180011
0.8726	High Similarity	NPC143328
0.8718	High Similarity	NPC226656
0.8718	High Similarity	NPC66508
0.8718	High Similarity	NPC472280
0.8718	High Similarity	NPC256925
0.8718	High Similarity	NPC38898
0.8718	High Similarity	NPC234255
0.8718	High Similarity	NPC234485
0.8716	High Similarity	NPC1268
0.871	High Similarity	NPC291802
0.871	High Similarity	NPC295646
0.871	High Similarity	NPC257648
0.871	High Similarity	NPC35763
0.871	High Similarity	NPC237994
0.871	High Similarity	NPC121522
0.871	High Similarity	NPC323626
0.871	High Similarity	NPC131266
0.871	High Similarity	NPC100263
0.871	High Similarity	NPC477231
0.871	High Similarity	NPC216769
0.871	High Similarity	NPC100971
0.871	High Similarity	NPC269451
0.871	High Similarity	NPC245382
0.871	High Similarity	NPC324233
0.871	High Similarity	NPC181209
0.871	High Similarity	NPC209487
0.8704	High Similarity	NPC99613
0.8704	High Similarity	NPC49487
0.8701	High Similarity	NPC294646
0.8699	High Similarity	NPC88065

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 NPC164912 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	1014
0.2-0.3	1506
0.3-0.4	2652
0.4-0.5	1866
0.5-0.6	1060
0.6-0.7	496
0.7-0.8	169
0.8-0.85	19
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8861	High Similarity	NPD6232	Discontinued
0.8812	High Similarity	NPD7473	Discontinued
0.8535	High Similarity	NPD2393	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD1934	Approved
0.8428	Intermediate Similarity	NPD3882	Suspended
0.8418	Intermediate Similarity	NPD2801	Approved
0.8267	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2935	Discontinued
0.8198	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5844	Phase 1
0.8113	Intermediate Similarity	NPD4380	Phase 2
0.8084	Intermediate Similarity	NPD3818	Discontinued
0.8077	Intermediate Similarity	NPD1511	Approved
0.8075	Intermediate Similarity	NPD7819	Suspended
0.805	Intermediate Similarity	NPD3226	Approved
0.8049	Intermediate Similarity	NPD5494	Approved
0.8039	Intermediate Similarity	NPD2346	Discontinued
0.8027	Intermediate Similarity	NPD9494	Approved
0.8026	Intermediate Similarity	NPD1510	Phase 2
0.8025	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1512	Approved
0.7937	Intermediate Similarity	NPD7458	Discontinued
0.7927	Intermediate Similarity	NPD7075	Discontinued
0.7914	Intermediate Similarity	NPD3817	Phase 2
0.7911	Intermediate Similarity	NPD2533	Approved
0.7911	Intermediate Similarity	NPD2534	Approved
0.7911	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD2532	Approved
0.7898	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1470	Approved
0.7882	Intermediate Similarity	NPD7074	Phase 3
0.7881	Intermediate Similarity	NPD1240	Approved
0.7877	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7054	Approved
0.7806	Intermediate Similarity	NPD2344	Approved
0.7805	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2799	Discontinued
0.7778	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD7472	Approved
0.7771	Intermediate Similarity	NPD7003	Approved
0.7756	Intermediate Similarity	NPD1549	Phase 2
0.7744	Intermediate Similarity	NPD1465	Phase 2
0.7742	Intermediate Similarity	NPD5404	Approved
0.7742	Intermediate Similarity	NPD5408	Approved
0.7742	Intermediate Similarity	NPD5405	Approved
0.7742	Intermediate Similarity	NPD5406	Approved
0.7736	Intermediate Similarity	NPD7390	Discontinued
0.773	Intermediate Similarity	NPD7411	Suspended
0.7716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD447	Suspended
0.7707	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6801	Discontinued
0.7677	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6234	Discontinued
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7644	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6797	Phase 2
0.7628	Intermediate Similarity	NPD2796	Approved
0.7625	Intermediate Similarity	NPD6799	Approved
0.7619	Intermediate Similarity	NPD1201	Approved
0.7614	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2309	Approved
0.7605	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2798	Approved
0.76	Intermediate Similarity	NPD8312	Approved
0.76	Intermediate Similarity	NPD8313	Approved
0.7596	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6781	Approved
0.7596	Intermediate Similarity	NPD6776	Approved
0.7596	Intermediate Similarity	NPD6778	Approved
0.7596	Intermediate Similarity	NPD6777	Approved
0.7596	Intermediate Similarity	NPD6779	Approved
0.7596	Intermediate Similarity	NPD6782	Approved
0.7596	Intermediate Similarity	NPD6780	Approved
0.7593	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD3926	Phase 2
0.7586	Intermediate Similarity	NPD7251	Discontinued
0.7586	Intermediate Similarity	NPD6559	Discontinued
0.7576	Intermediate Similarity	NPD37	Approved
0.7571	Intermediate Similarity	NPD8150	Discontinued
0.7568	Intermediate Similarity	NPD3972	Approved
0.7547	Intermediate Similarity	NPD8166	Discontinued
0.7545	Intermediate Similarity	NPD7768	Phase 2
0.7544	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7808	Phase 3
0.7534	Intermediate Similarity	NPD1651	Approved
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3749	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7473	Intermediate Similarity	NPD7435	Discontinued
0.7471	Intermediate Similarity	NPD1247	Approved
0.7468	Intermediate Similarity	NPD1471	Phase 3
0.7467	Intermediate Similarity	NPD1283	Approved
0.7456	Intermediate Similarity	NPD919	Approved
0.744	Intermediate Similarity	NPD4965	Approved
0.744	Intermediate Similarity	NPD4966	Approved
0.744	Intermediate Similarity	NPD4967	Phase 2
0.7438	Intermediate Similarity	NPD3750	Approved
0.7419	Intermediate Similarity	NPD4060	Phase 1
0.7419	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3620	Phase 2
0.7414	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5536	Phase 2
0.738	Intermediate Similarity	NPD7697	Approved
0.738	Intermediate Similarity	NPD7696	Phase 3
0.738	Intermediate Similarity	NPD7698	Approved
0.7372	Intermediate Similarity	NPD230	Phase 1
0.7368	Intermediate Similarity	NPD8151	Discontinued
0.7368	Intermediate Similarity	NPD7199	Phase 2
0.7365	Intermediate Similarity	NPD4626	Approved
0.7356	Intermediate Similarity	NPD7228	Approved
0.7356	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD1876	Approved
0.734	Intermediate Similarity	NPD7871	Phase 2
0.734	Intermediate Similarity	NPD7870	Phase 2
0.7338	Intermediate Similarity	NPD3027	Phase 3
0.7329	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5710	Approved
0.7326	Intermediate Similarity	NPD5711	Approved
0.7322	Intermediate Similarity	NPD6534	Approved
0.7322	Intermediate Similarity	NPD6535	Approved
0.7317	Intermediate Similarity	NPD6273	Approved
0.7316	Intermediate Similarity	NPD7701	Phase 2
0.7303	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1203	Approved
0.7296	Intermediate Similarity	NPD2438	Suspended
0.7296	Intermediate Similarity	NPD1551	Phase 2
0.7284	Intermediate Similarity	NPD6190	Approved
0.7283	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5402	Approved
0.7278	Intermediate Similarity	NPD5978	Approved
0.7278	Intermediate Similarity	NPD5977	Approved
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7268	Intermediate Similarity	NPD6213	Phase 3
0.7268	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6212	Phase 3
0.7267	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2800	Approved
0.7267	Intermediate Similarity	NPD1281	Approved
0.724	Intermediate Similarity	NPD7874	Approved
0.724	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6823	Phase 2
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.7232	Intermediate Similarity	NPD5953	Discontinued
0.7215	Intermediate Similarity	NPD6651	Approved
0.7204	Intermediate Similarity	NPD7700	Phase 2
0.7204	Intermediate Similarity	NPD7699	Phase 2
0.7202	Intermediate Similarity	NPD7801	Approved
0.7197	Intermediate Similarity	NPD2979	Phase 3
0.7191	Intermediate Similarity	NPD7685	Pre-registration
0.719	Intermediate Similarity	NPD1164	Approved
0.7188	Intermediate Similarity	NPD6099	Approved
0.7188	Intermediate Similarity	NPD6100	Approved
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7181	Intermediate Similarity	NPD5691	Approved
0.7179	Intermediate Similarity	NPD6798	Discontinued
0.7179	Intermediate Similarity	NPD3764	Approved
0.7179	Intermediate Similarity	NPD411	Approved
0.7179	Intermediate Similarity	NPD3268	Approved
0.7171	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5403	Approved
0.7159	Intermediate Similarity	NPD7177	Discontinued
0.7152	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7028	Phase 2
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3300	Phase 2
0.7126	Intermediate Similarity	NPD3787	Discontinued
0.7125	Intermediate Similarity	NPD3748	Approved
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.7115	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD9717	Approved
0.7103	Intermediate Similarity	NPD228	Approved
0.7095	Intermediate Similarity	NPD9493	Approved
0.7089	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1613	Approved
0.7078	Intermediate Similarity	NPD2797	Approved
0.7076	Intermediate Similarity	NPD2296	Approved
0.7069	Intermediate Similarity	NPD8127	Discontinued
0.7068	Intermediate Similarity	NPD8319	Approved
0.7068	Intermediate Similarity	NPD8320	Phase 1
0.7066	Intermediate Similarity	NPD920	Approved
0.7056	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6674	Discontinued
0.7051	Intermediate Similarity	NPD1529	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