NPASS Compound

Structure

CID118427 OpenBabel06191715472D 23 25 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 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 -3.4641 -2.0000 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 -1.7321 -0.0000 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 -3.4641 -3.0000 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 -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 4 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 22 1 0 0 0 0 8 14 2 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 19 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 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	308.569
LogP:	2.919
LogD:	2.366
LogS:	-4.341
# Rotatable Bonds:	3
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	2.471
Fsp3:	0.176
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:	-4.938
MDCK Permeability:	1.592242369952146e-05
Pgp-inhibitor:	0.558
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.157
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	98.08692932128906%
Volume Distribution (VD):	0.441
Pgp-substrate:	3.1724777221679688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.88
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.577
CYP2C9-substrate:	0.185
CYP2D6-inhibitor:	0.103
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.467
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	7.52
Half-life (T1/2):	0.177

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.897
Rat Oral Acute Toxicity:	0.243
Maximum Recommended Daily Dose:	0.299
Skin Sensitization:	0.441
Carcinogencity:	0.948
Eye Corrosion:	0.003
Eye Irritation:	0.914
Respiratory Toxicity:	0.077

Download Data

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

Natural Product: NPC118427

Natural Product ID:	NPC118427
*Common Name:**	5,15-Di-O-Methyl Morindol
IUPAC Name:	1,6-dihydroxy-5-methoxy-2-(methoxymethyl)anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	KKHLOCIPXRSWKM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-22-7-8-3-4-9-12(14(8)19)15(20)10-5-6-11(18)17(23-2)13(10)16(9)21/h3-6,18-19H,7H2,1-2H3
SMILES:	COCc1ccc2c(c1O)C(=O)c1ccc(c(c1C2=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445667
PubChem CID:	11674044
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[521578]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	13.7	%	PMID[521578]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	45.1	%	PMID[521578]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	69.3	%	PMID[521578]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	95.1	%	PMID[521578]

☑ 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 NPC118427 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	NPC164912
0.9592	High Similarity	NPC302783
0.9592	High Similarity	NPC473201
0.9583	High Similarity	NPC73416
0.9583	High Similarity	NPC160777
0.9533	High Similarity	NPC178976
0.9467	High Similarity	NPC77807
0.9467	High Similarity	NPC5379
0.9467	High Similarity	NPC14561
0.9459	High Similarity	NPC144283
0.9404	High Similarity	NPC37543
0.9404	High Similarity	NPC199463
0.9396	High Similarity	NPC149889
0.9396	High Similarity	NPC312338
0.9346	High Similarity	NPC311740
0.9338	High Similarity	NPC279605
0.9333	High Similarity	NPC107109
0.9281	High Similarity	NPC84571
0.9184	High Similarity	NPC478019
0.9172	High Similarity	NPC84273
0.9167	High Similarity	NPC223336
0.9167	High Similarity	NPC26386
0.911	High Similarity	NPC192597
0.911	High Similarity	NPC176030
0.911	High Similarity	NPC169214
0.911	High Similarity	NPC229218
0.911	High Similarity	NPC141817
0.9085	High Similarity	NPC213401
0.9079	High Similarity	NPC93552
0.9073	High Similarity	NPC78505
0.906	High Similarity	NPC58373
0.9013	High Similarity	NPC137125
0.9013	High Similarity	NPC3744
0.9007	High Similarity	NPC290954
0.9007	High Similarity	NPC280295
0.9007	High Similarity	NPC255641
0.8993	High Similarity	NPC39361
0.8986	High Similarity	NPC196941
0.8986	High Similarity	NPC309169
0.8981	High Similarity	NPC101769
0.898	High Similarity	NPC11314
0.8968	High Similarity	NPC245891
0.8968	High Similarity	NPC104876
0.8954	High Similarity	NPC475770
0.8954	High Similarity	NPC474000
0.8947	High Similarity	NPC306011
0.8947	High Similarity	NPC75377
0.8947	High Similarity	NPC472838
0.8947	High Similarity	NPC70320
0.8947	High Similarity	NPC256406
0.894	High Similarity	NPC37220
0.894	High Similarity	NPC69430
0.894	High Similarity	NPC142876
0.894	High Similarity	NPC40290
0.894	High Similarity	NPC264550
0.894	High Similarity	NPC139293
0.894	High Similarity	NPC134293
0.894	High Similarity	NPC195763
0.894	High Similarity	NPC264289
0.894	High Similarity	NPC333691
0.894	High Similarity	NPC200060
0.8933	High Similarity	NPC52692
0.8933	High Similarity	NPC312929
0.8933	High Similarity	NPC126767
0.8933	High Similarity	NPC190648
0.8933	High Similarity	NPC289042
0.8933	High Similarity	NPC245584
0.8933	High Similarity	NPC118027
0.8933	High Similarity	NPC56433
0.8924	High Similarity	NPC303174
0.8896	High Similarity	NPC39184
0.8889	High Similarity	NPC258502
0.8882	High Similarity	NPC147735
0.8882	High Similarity	NPC58310
0.8882	High Similarity	NPC470568
0.8882	High Similarity	NPC472279
0.8882	High Similarity	NPC85131
0.8882	High Similarity	NPC295977
0.8875	High Similarity	NPC163130
0.8875	High Similarity	NPC165979
0.8874	High Similarity	NPC254702
0.8874	High Similarity	NPC139364
0.8874	High Similarity	NPC194653
0.8874	High Similarity	NPC80710
0.8874	High Similarity	NPC203747
0.8867	High Similarity	NPC300540
0.8859	High Similarity	NPC142165
0.8859	High Similarity	NPC300603
0.8859	High Similarity	NPC21599
0.8859	High Similarity	NPC193703
0.8859	High Similarity	NPC91694
0.8851	High Similarity	NPC69755
0.8836	High Similarity	NPC61398
0.8836	High Similarity	NPC416
0.8831	High Similarity	NPC208806
0.8828	High Similarity	NPC324929
0.8824	High Similarity	NPC470569
0.8816	High Similarity	NPC171916
0.8816	High Similarity	NPC38545
0.8812	High Similarity	NPC234331
0.8808	High Similarity	NPC188074
0.8808	High Similarity	NPC125449
0.8797	High Similarity	NPC294965
0.8792	High Similarity	NPC254659
0.8792	High Similarity	NPC66593
0.879	High Similarity	NPC36217
0.879	High Similarity	NPC185617
0.8782	High Similarity	NPC35598
0.8782	High Similarity	NPC222689
0.8782	High Similarity	NPC136674
0.8776	High Similarity	NPC1268
0.8774	High Similarity	NPC168247
0.8774	High Similarity	NPC57674
0.8774	High Similarity	NPC134287
0.8774	High Similarity	NPC152951
0.8774	High Similarity	NPC130589
0.8774	High Similarity	NPC230149
0.8774	High Similarity	NPC117992
0.8774	High Similarity	NPC38898
0.8766	High Similarity	NPC269451
0.8766	High Similarity	NPC131266
0.8766	High Similarity	NPC474993
0.8766	High Similarity	NPC245382
0.8766	High Similarity	NPC35763
0.8766	High Similarity	NPC216769
0.8766	High Similarity	NPC291802
0.8766	High Similarity	NPC100971
0.8766	High Similarity	NPC181209
0.8766	High Similarity	NPC295646
0.8766	High Similarity	NPC40356
0.8766	High Similarity	NPC121522
0.8766	High Similarity	NPC100263
0.8766	High Similarity	NPC209487
0.8766	High Similarity	NPC154683
0.8765	High Similarity	NPC158226
0.8758	High Similarity	NPC294646
0.875	High Similarity	NPC43319
0.875	High Similarity	NPC29160
0.875	High Similarity	NPC203077
0.875	High Similarity	NPC294226
0.875	High Similarity	NPC166036
0.875	High Similarity	NPC238279
0.875	High Similarity	NPC55327
0.8742	High Similarity	NPC12377
0.8742	High Similarity	NPC236132
0.8742	High Similarity	NPC270837
0.8733	High Similarity	NPC19896
0.8733	High Similarity	NPC48762
0.8726	High Similarity	NPC477410
0.8726	High Similarity	NPC235448
0.8726	High Similarity	NPC85121
0.8718	High Similarity	NPC288353
0.8718	High Similarity	NPC472455
0.8712	High Similarity	NPC199357
0.871	High Similarity	NPC33051
0.871	High Similarity	NPC70433
0.871	High Similarity	NPC227337
0.871	High Similarity	NPC273462
0.871	High Similarity	NPC469550
0.871	High Similarity	NPC124714
0.871	High Similarity	NPC49402
0.871	High Similarity	NPC472905
0.871	High Similarity	NPC127172
0.8701	High Similarity	NPC31363
0.8701	High Similarity	NPC45291
0.8701	High Similarity	NPC19980
0.8696	High Similarity	NPC218226
0.8693	High Similarity	NPC472837
0.8693	High Similarity	NPC261322
0.8684	High Similarity	NPC77598
0.8679	High Similarity	NPC201800
0.8675	High Similarity	NPC49282
0.8675	High Similarity	NPC34482
0.8675	High Similarity	NPC157133
0.8675	High Similarity	NPC225351
0.8671	High Similarity	NPC14353
0.8671	High Similarity	NPC56085
0.8671	High Similarity	NPC472902
0.8671	High Similarity	NPC228785
0.8671	High Similarity	NPC155302
0.8671	High Similarity	NPC471973
0.8671	High Similarity	NPC161947
0.8671	High Similarity	NPC474960
0.8667	High Similarity	NPC239608
0.8667	High Similarity	NPC46161
0.8667	High Similarity	NPC53016
0.8667	High Similarity	NPC287722
0.8667	High Similarity	NPC50954
0.8662	High Similarity	NPC129684
0.8662	High Similarity	NPC304008
0.8662	High Similarity	NPC167098
0.8662	High Similarity	NPC187745
0.8662	High Similarity	NPC299520
0.8662	High Similarity	NPC219867
0.8662	High Similarity	NPC296044
0.8662	High Similarity	NPC78103
0.8662	High Similarity	NPC161960
0.8662	High Similarity	NPC180011
0.8662	High Similarity	NPC143328
0.8662	High Similarity	NPC291508

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 NPC118427 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
0.8797	High Similarity	NPD6232	Discontinued
0.875	High Similarity	NPD7473	Discontinued
0.8526	High Similarity	NPD1934	Approved
0.8471	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD3882	Suspended
0.8354	Intermediate Similarity	NPD2801	Approved
0.8322	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD2935	Discontinued
0.814	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1511	Approved
0.8121	Intermediate Similarity	NPD6166	Phase 2
0.8121	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD3226	Approved
0.8092	Intermediate Similarity	NPD2346	Discontinued
0.8084	Intermediate Similarity	NPD5844	Phase 1
0.8082	Intermediate Similarity	NPD9494	Approved
0.8079	Intermediate Similarity	NPD1510	Phase 2
0.8067	Intermediate Similarity	NPD1607	Approved
0.8054	Intermediate Similarity	NPD943	Approved
0.805	Intermediate Similarity	NPD4380	Phase 2
0.8025	Intermediate Similarity	NPD1512	Approved
0.8024	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD7819	Suspended
0.7988	Intermediate Similarity	NPD5494	Approved
0.7962	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD1470	Approved
0.7939	Intermediate Similarity	NPD6959	Discontinued
0.7933	Intermediate Similarity	NPD1240	Approved
0.7914	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7458	Discontinued
0.7866	Intermediate Similarity	NPD7075	Discontinued
0.7857	Intermediate Similarity	NPD2344	Approved
0.7853	Intermediate Similarity	NPD3817	Phase 2
0.7848	Intermediate Similarity	NPD2533	Approved
0.7848	Intermediate Similarity	NPD2532	Approved
0.7848	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2534	Approved
0.7841	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7074	Phase 3
0.7808	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1549	Phase 2
0.7791	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1465	Phase 2
0.7765	Intermediate Similarity	NPD7054	Approved
0.7763	Intermediate Similarity	NPD447	Suspended
0.7744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2799	Discontinued
0.7727	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7472	Approved
0.7716	Intermediate Similarity	NPD6599	Discontinued
0.7707	Intermediate Similarity	NPD7003	Approved
0.7692	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5408	Approved
0.7677	Intermediate Similarity	NPD5406	Approved
0.7677	Intermediate Similarity	NPD5404	Approved
0.7677	Intermediate Similarity	NPD5405	Approved
0.7673	Intermediate Similarity	NPD7390	Discontinued
0.7671	Intermediate Similarity	NPD1201	Approved
0.7669	Intermediate Similarity	NPD7411	Suspended
0.7658	Intermediate Similarity	NPD2309	Approved
0.7654	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6801	Discontinued
0.7605	Intermediate Similarity	NPD6234	Discontinued
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7586	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6797	Phase 2
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.7564	Intermediate Similarity	NPD2796	Approved
0.7562	Intermediate Similarity	NPD6799	Approved
0.7557	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3749	Approved
0.7545	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD8313	Approved
0.7543	Intermediate Similarity	NPD8312	Approved
0.7541	Intermediate Similarity	NPD6781	Approved
0.7541	Intermediate Similarity	NPD6780	Approved
0.7541	Intermediate Similarity	NPD6777	Approved
0.7541	Intermediate Similarity	NPD6779	Approved
0.7541	Intermediate Similarity	NPD6782	Approved
0.7541	Intermediate Similarity	NPD6776	Approved
0.7541	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6778	Approved
0.7533	Intermediate Similarity	NPD2798	Approved
0.7532	Intermediate Similarity	NPD1933	Approved
0.7531	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7251	Discontinued
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.7529	Intermediate Similarity	NPD3926	Phase 2
0.7517	Intermediate Similarity	NPD1283	Approved
0.7516	Intermediate Similarity	NPD1471	Phase 3
0.7515	Intermediate Similarity	NPD1247	Approved
0.7515	Intermediate Similarity	NPD37	Approved
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD3972	Approved
0.7486	Intermediate Similarity	NPD7808	Phase 3
0.7485	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7768	Phase 2
0.7484	Intermediate Similarity	NPD8166	Discontinued
0.7484	Intermediate Similarity	NPD3750	Approved
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1651	Approved
0.7453	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7435	Discontinued
0.7419	Intermediate Similarity	NPD230	Phase 1
0.74	Intermediate Similarity	NPD1876	Approved
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7379	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3620	Phase 2
0.7355	Intermediate Similarity	NPD4060	Phase 1
0.7355	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1203	Approved
0.7342	Intermediate Similarity	NPD1551	Phase 2
0.7329	Intermediate Similarity	NPD5536	Phase 2
0.7326	Intermediate Similarity	NPD7696	Phase 3
0.7326	Intermediate Similarity	NPD7697	Approved
0.7326	Intermediate Similarity	NPD7698	Approved
0.7316	Intermediate Similarity	NPD8151	Discontinued
0.7315	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1281	Approved
0.7312	Intermediate Similarity	NPD2800	Approved
0.731	Intermediate Similarity	NPD7199	Phase 2
0.7299	Intermediate Similarity	NPD7228	Approved
0.7297	Intermediate Similarity	NPD4626	Approved
0.7287	Intermediate Similarity	NPD7870	Phase 2
0.7287	Intermediate Similarity	NPD7871	Phase 2
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7273	Intermediate Similarity	NPD3027	Phase 3
0.7268	Intermediate Similarity	NPD6534	Approved
0.7268	Intermediate Similarity	NPD6535	Approved
0.7267	Intermediate Similarity	NPD5710	Approved
0.7267	Intermediate Similarity	NPD5711	Approved
0.7263	Intermediate Similarity	NPD7701	Phase 2
0.7256	Intermediate Similarity	NPD6273	Approved
0.7247	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1164	Approved
0.7233	Intermediate Similarity	NPD2438	Suspended
0.7226	Intermediate Similarity	NPD411	Approved
0.7226	Intermediate Similarity	NPD3764	Approved
0.7225	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6190	Approved
0.7219	Intermediate Similarity	NPD5978	Approved
0.7219	Intermediate Similarity	NPD5977	Approved
0.7219	Intermediate Similarity	NPD5402	Approved
0.7213	Intermediate Similarity	NPD6212	Phase 3
0.7213	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6213	Phase 3
0.7208	Intermediate Similarity	NPD6832	Phase 2
0.7197	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7874	Approved
0.7188	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6823	Phase 2
0.7175	Intermediate Similarity	NPD5953	Discontinued
0.717	Intermediate Similarity	NPD3748	Approved
0.7153	Intermediate Similarity	NPD228	Approved
0.7152	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD6651	Approved
0.7151	Intermediate Similarity	NPD7700	Phase 2
0.7151	Intermediate Similarity	NPD7699	Phase 2
0.715	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD9493	Approved
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7134	Intermediate Similarity	NPD1613	Approved
0.7134	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2979	Phase 3
0.7127	Intermediate Similarity	NPD8434	Phase 2
0.7125	Intermediate Similarity	NPD6100	Approved
0.7125	Intermediate Similarity	NPD6099	Approved
0.7118	Intermediate Similarity	NPD2296	Approved
0.7115	Intermediate Similarity	NPD3268	Approved
0.7115	Intermediate Similarity	NPD6798	Discontinued
0.7114	Intermediate Similarity	NPD5691	Approved
0.7108	Intermediate Similarity	NPD920	Approved
0.7108	Intermediate Similarity	NPD5403	Approved
0.7105	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7177	Discontinued
0.7097	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5401	Approved
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7028	Phase 2
0.7073	Intermediate Similarity	NPD3300	Phase 2
0.7069	Intermediate Similarity	NPD3787	Discontinued
0.7055	Intermediate Similarity	NPD5283	Phase 1
0.7051	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4307	Phase 2
0.7016	Intermediate Similarity	NPD8320	Phase 1
0.7016	Intermediate Similarity	NPD8319	Approved
0.7013	Intermediate Similarity	NPD2797	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