NPASS Compound

Structure

CID296044 OpenBabel06191716102D 24 27 0 0 0 0 0 0 0 0999 V2000 4.3388 -2.8630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1304 -1.3637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6350 -0.5371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6622 -2.2061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6714 -0.5528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6986 -2.2218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3503 0.0367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5117 0.5095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8596 -2.4171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2032 -1.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3609 -0.9270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6721 0.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -1.4477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7154 -2.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6827 -0.9454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5329 -1.4293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5435 -2.3987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8277 0.4911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0105 -0.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7312 -3.8505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8193 1.4571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8234 -1.4513 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3790 -2.8714 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 23 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 10 2 0 0 0 0 6 10 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 11 16 2 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.07
Volume:	320.541
LogP:	4.24
LogD:	3.676
LogS:	-4.322
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.577
Synthetic Accessibility Score:	2.45
Fsp3:	0.053
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.864
MDCK Permeability:	3.0308605346363038e-05
Pgp-inhibitor:	0.07
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.348
Plasma Protein Binding (PPB):	97.98348236083984%
Volume Distribution (VD):	0.552
Pgp-substrate:	2.281383991241455%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.139
CYP2C19-inhibitor:	0.774
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.69
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.081

ADMET: Excretion

Clearance (CL):	4.989
Half-life (T1/2):	0.532

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.5
AMES Toxicity:	0.237
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.363
Skin Sensitization:	0.945
Carcinogencity:	0.077
Eye Corrosion:	0.017
Eye Irritation:	0.958
Respiratory Toxicity:	0.385

Download Data

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

Natural Product: NPC296044

Natural Product ID:	NPC296044
*Common Name:**	Haemodorone
IUPAC Name:	n.a.
Synonyms:	haemodorone
Standard InCHIKey:	GVBJAQUCCACYEW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H12O5/c1-23-17-14(20)9-13-15-12(18(21)24-19(13)22)8-7-11(16(15)17)10-5-3-2-4-6-10/h2-9,20H,1H3
SMILES:	COc1c(O)cc2c3c1c(ccc3C(=O)OC2=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551732
PubChem CID:	44179579
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0001871] Naphthalenecarboxylic acids and derivatives [CHEMONTID:0003071] 1,8-naphthalic anhydrides

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	Eukaryota	n.a.	La Banderita, Tucumn, Argentina	2005-DEC	PMID[19239238]
NPO6823	Haemodorum simplex	Species	Haemodoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19419186]
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	Eukaryota	n.a.	La Banderita, Tucumn, Argentina	n.a.	PMID[20384357]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5095	Digitalis ferruginea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6654	Eucalyptus phellandra	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5095	Digitalis ferruginea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4260	Stelletta maxima	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5095	Digitalis ferruginea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7281	Veltheimia capensis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6654	Eucalyptus phellandra	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5785	Corymbium villosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6998	Lecanora polytropa	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7742	Eucalyptus caesia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6104	Solidago elongata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6823	Haemodorum simplex	Species	Haemodoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2101	Incisitermes immigrans	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5396	Clibadium laxum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	26000.0	nM	PMID[499846]

☑ 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 NPC296044 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	400
0.1-0.2	1820
0.2-0.3	3860
0.3-0.4	9326
0.4-0.5	8766
0.5-0.6	3384
0.6-0.7	6099
0.7-0.8	7630
0.8-0.85	1272
0.85-0.9	132
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC167098
0.953	High Similarity	NPC300983
0.9226	High Similarity	NPC202495
0.9226	High Similarity	NPC143328
0.9161	High Similarity	NPC109765
0.9097	High Similarity	NPC472835
0.9026	High Similarity	NPC302783
0.9026	High Similarity	NPC473201
0.9026	High Similarity	NPC124842
0.902	High Similarity	NPC261322
0.8917	High Similarity	NPC288353
0.891	High Similarity	NPC62051
0.8903	High Similarity	NPC118332
0.8903	High Similarity	NPC306011
0.8903	High Similarity	NPC472838
0.8903	High Similarity	NPC78505
0.8896	High Similarity	NPC472837
0.8896	High Similarity	NPC303989
0.8882	High Similarity	NPC26386
0.8874	High Similarity	NPC50954
0.8846	High Similarity	NPC137125
0.8846	High Similarity	NPC295646
0.8846	High Similarity	NPC3744
0.8824	High Similarity	NPC58752
0.8824	High Similarity	NPC39361
0.882	High Similarity	NPC477689
0.8816	High Similarity	NPC260152
0.8816	High Similarity	NPC275278
0.8805	High Similarity	NPC37502
0.8805	High Similarity	NPC267627
0.8805	High Similarity	NPC40702
0.8782	High Similarity	NPC70320
0.878	High Similarity	NPC52598
0.8766	High Similarity	NPC470757
0.8758	High Similarity	NPC22130
0.8758	High Similarity	NPC116838
0.8758	High Similarity	NPC144843
0.875	High Similarity	NPC24627
0.875	High Similarity	NPC53889
0.8742	High Similarity	NPC178976
0.8742	High Similarity	NPC247713
0.8735	High Similarity	NPC193377
0.8734	High Similarity	NPC80489
0.872	High Similarity	NPC165979
0.872	High Similarity	NPC163130
0.8718	High Similarity	NPC58310
0.8718	High Similarity	NPC295977
0.8712	High Similarity	NPC263212
0.8704	High Similarity	NPC45943
0.8704	High Similarity	NPC67959
0.8696	High Similarity	NPC131905
0.8696	High Similarity	NPC469889
0.8696	High Similarity	NPC311740
0.8693	High Similarity	NPC113397
0.8693	High Similarity	NPC300603
0.8693	High Similarity	NPC91694
0.8688	High Similarity	NPC87317
0.8688	High Similarity	NPC245891
0.8688	High Similarity	NPC45846
0.8688	High Similarity	NPC104876
0.8684	High Similarity	NPC192597
0.8684	High Similarity	NPC176030
0.8684	High Similarity	NPC141817
0.8684	High Similarity	NPC229218
0.8684	High Similarity	NPC169214
0.8683	High Similarity	NPC196771
0.8679	High Similarity	NPC227062
0.8679	High Similarity	NPC213401
0.8679	High Similarity	NPC279605
0.8679	High Similarity	NPC5379
0.8679	High Similarity	NPC14561
0.8679	High Similarity	NPC77807
0.8675	High Similarity	NPC290664
0.8675	High Similarity	NPC326065
0.8667	High Similarity	NPC109827
0.8667	High Similarity	NPC313304
0.8667	High Similarity	NPC124470
0.8662	High Similarity	NPC144283
0.8662	High Similarity	NPC75377
0.8662	High Similarity	NPC118427
0.8662	High Similarity	NPC267091
0.8659	High Similarity	NPC234331
0.8659	High Similarity	NPC469521
0.865	High Similarity	NPC471788
0.8645	High Similarity	NPC52692
0.8645	High Similarity	NPC58373
0.8642	High Similarity	NPC469472
0.8642	High Similarity	NPC198796
0.8636	High Similarity	NPC73416
0.8636	High Similarity	NPC160777
0.8636	High Similarity	NPC75295
0.8634	High Similarity	NPC47623
0.8634	High Similarity	NPC84571
0.8631	High Similarity	NPC47191
0.8625	High Similarity	NPC68324
0.8625	High Similarity	NPC114179
0.8625	High Similarity	NPC289322
0.8625	High Similarity	NPC160512
0.8625	High Similarity	NPC156818
0.8625	High Similarity	NPC199463
0.8625	High Similarity	NPC37543
0.8625	High Similarity	NPC38779
0.8618	High Similarity	NPC91546
0.8616	High Similarity	NPC38898
0.8614	High Similarity	NPC158226
0.8608	High Similarity	NPC164912
0.8606	High Similarity	NPC117911
0.8605	High Similarity	NPC205721
0.8599	High Similarity	NPC31132
0.8599	High Similarity	NPC243891
0.8598	High Similarity	NPC29160
0.859	High Similarity	NPC98809
0.859	High Similarity	NPC476394
0.858	High Similarity	NPC216916
0.8571	High Similarity	NPC79736
0.8571	High Similarity	NPC125713
0.8571	High Similarity	NPC315157
0.8571	High Similarity	NPC309169
0.8571	High Similarity	NPC67629
0.8571	High Similarity	NPC196941
0.8571	High Similarity	NPC308006
0.8571	High Similarity	NPC471305
0.8563	High Similarity	NPC199357
0.8563	High Similarity	NPC316539
0.8562	High Similarity	NPC250436
0.8562	High Similarity	NPC104983
0.8562	High Similarity	NPC300845
0.8562	High Similarity	NPC291948
0.8562	High Similarity	NPC88803
0.8553	High Similarity	NPC107109
0.8553	High Similarity	NPC178134
0.8545	High Similarity	NPC177362
0.8529	High Similarity	NPC475996
0.8528	High Similarity	NPC294965
0.8528	High Similarity	NPC473445
0.8528	High Similarity	NPC42797
0.8526	High Similarity	NPC155910
0.8526	High Similarity	NPC119767
0.8526	High Similarity	NPC17042
0.8521	High Similarity	NPC267549
0.8521	High Similarity	NPC207467
0.8519	High Similarity	NPC24164
0.8519	High Similarity	NPC141574
0.8519	High Similarity	NPC21046
0.8516	High Similarity	NPC258856
0.8509	High Similarity	NPC35598
0.8509	High Similarity	NPC222689
0.8503	High Similarity	NPC474075
0.8503	High Similarity	NPC312006
0.8503	High Similarity	NPC471921
0.8503	High Similarity	NPC114550
0.8503	High Similarity	NPC471920
0.8503	High Similarity	NPC471922
0.8503	High Similarity	NPC20114
0.8503	High Similarity	NPC292712
0.8503	High Similarity	NPC4200
0.8503	High Similarity	NPC129930
0.85	High Similarity	NPC20541
0.85	High Similarity	NPC268008
0.8494	Intermediate Similarity	NPC266545
0.8494	Intermediate Similarity	NPC99613
0.8494	Intermediate Similarity	NPC202428
0.8494	Intermediate Similarity	NPC49487
0.8491	Intermediate Similarity	NPC474656
0.8491	Intermediate Similarity	NPC131121
0.8491	Intermediate Similarity	NPC180388
0.8491	Intermediate Similarity	NPC149889
0.8491	Intermediate Similarity	NPC312338
0.8485	Intermediate Similarity	NPC37870
0.8485	Intermediate Similarity	NPC174734
0.8485	Intermediate Similarity	NPC474042
0.8485	Intermediate Similarity	NPC200726
0.8485	Intermediate Similarity	NPC43319
0.8476	Intermediate Similarity	NPC291977
0.8476	Intermediate Similarity	NPC236132
0.8476	Intermediate Similarity	NPC223006
0.8476	Intermediate Similarity	NPC272750
0.8476	Intermediate Similarity	NPC134047
0.8476	Intermediate Similarity	NPC270837
0.8476	Intermediate Similarity	NPC173729
0.8471	Intermediate Similarity	NPC472839
0.8471	Intermediate Similarity	NPC475848
0.8471	Intermediate Similarity	NPC473785
0.8471	Intermediate Similarity	NPC474306
0.8462	Intermediate Similarity	NPC475054
0.8462	Intermediate Similarity	NPC472723
0.8462	Intermediate Similarity	NPC474991
0.8456	Intermediate Similarity	NPC283823
0.8456	Intermediate Similarity	NPC159418
0.8452	Intermediate Similarity	NPC472836
0.8447	Intermediate Similarity	NPC239113
0.8447	Intermediate Similarity	NPC478223
0.8447	Intermediate Similarity	NPC318432
0.8447	Intermediate Similarity	NPC472453
0.8447	Intermediate Similarity	NPC115123
0.8443	Intermediate Similarity	NPC180768
0.8439	Intermediate Similarity	NPC105591
0.8438	Intermediate Similarity	NPC54179
0.8438	Intermediate Similarity	NPC116850
0.8438	Intermediate Similarity	NPC197188

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 NPC296044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	984
0.2-0.3	1596
0.3-0.4	2591
0.4-0.5	1875
0.5-0.6	1040
0.6-0.7	502
0.7-0.8	161
0.8-0.85	12
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8875	High Similarity	NPD6232	Discontinued
0.8834	High Similarity	NPD5844	Phase 1
0.8712	High Similarity	NPD7473	Discontinued
0.8562	High Similarity	NPD4868	Clinical (unspecified phase)
0.8553	High Similarity	NPD1465	Phase 2
0.8538	High Similarity	NPD8397	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD3226	Approved
0.8194	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD1934	Approved
0.8141	Intermediate Similarity	NPD7003	Approved
0.8101	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2346	Discontinued
0.8046	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4628	Phase 3
0.7988	Intermediate Similarity	NPD6166	Phase 2
0.7988	Intermediate Similarity	NPD2801	Approved
0.7988	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6959	Discontinued
0.7904	Intermediate Similarity	NPD6234	Discontinued
0.7895	Intermediate Similarity	NPD3764	Approved
0.7879	Intermediate Similarity	NPD7819	Suspended
0.7866	Intermediate Similarity	NPD7411	Suspended
0.7853	Intermediate Similarity	NPD7458	Discontinued
0.7844	Intermediate Similarity	NPD3749	Approved
0.7829	Intermediate Similarity	NPD8312	Approved
0.7829	Intermediate Similarity	NPD8313	Approved
0.7826	Intermediate Similarity	NPD2533	Approved
0.7826	Intermediate Similarity	NPD2532	Approved
0.7826	Intermediate Similarity	NPD2534	Approved
0.7821	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4380	Phase 2
0.7799	Intermediate Similarity	NPD3750	Approved
0.7791	Intermediate Similarity	NPD7177	Discontinued
0.7791	Intermediate Similarity	NPD7228	Approved
0.7784	Intermediate Similarity	NPD3882	Suspended
0.7778	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5408	Approved
0.7771	Intermediate Similarity	NPD5404	Approved
0.7771	Intermediate Similarity	NPD5406	Approved
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7771	Intermediate Similarity	NPD5405	Approved
0.7764	Intermediate Similarity	NPD1511	Approved
0.7751	Intermediate Similarity	NPD5494	Approved
0.7742	Intermediate Similarity	NPD230	Phase 1
0.7738	Intermediate Similarity	NPD7075	Discontinued
0.7733	Intermediate Similarity	NPD1283	Approved
0.773	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3817	Phase 2
0.7716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7685	Pre-registration
0.7711	Intermediate Similarity	NPD37	Approved
0.7701	Intermediate Similarity	NPD7074	Phase 3
0.7697	Intermediate Similarity	NPD9494	Approved
0.7688	Intermediate Similarity	NPD3818	Discontinued
0.7679	Intermediate Similarity	NPD4967	Phase 2
0.7679	Intermediate Similarity	NPD4965	Approved
0.7679	Intermediate Similarity	NPD4966	Approved
0.7679	Intermediate Similarity	NPD7768	Phase 2
0.7673	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1512	Approved
0.7665	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7054	Approved
0.764	Intermediate Similarity	NPD6190	Approved
0.7619	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6559	Discontinued
0.7602	Intermediate Similarity	NPD7199	Phase 2
0.76	Intermediate Similarity	NPD7472	Approved
0.7598	Intermediate Similarity	NPD8150	Discontinued
0.7578	Intermediate Similarity	NPD8166	Discontinued
0.7533	Intermediate Similarity	NPD1281	Approved
0.7516	Intermediate Similarity	NPD447	Suspended
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7485	Intermediate Similarity	NPD6599	Discontinued
0.7484	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3748	Approved
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7468	Intermediate Similarity	NPD1607	Approved
0.7458	Intermediate Similarity	NPD6797	Phase 2
0.7456	Intermediate Similarity	NPD8455	Phase 2
0.7455	Intermediate Similarity	NPD6273	Approved
0.7452	Intermediate Similarity	NPD2979	Phase 3
0.7452	Intermediate Similarity	NPD4060	Phase 1
0.744	Intermediate Similarity	NPD6386	Approved
0.744	Intermediate Similarity	NPD6385	Approved
0.7439	Intermediate Similarity	NPD7390	Discontinued
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.7434	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7251	Discontinued
0.7407	Intermediate Similarity	NPD7435	Discontinued
0.74	Intermediate Similarity	NPD4626	Approved
0.7396	Intermediate Similarity	NPD6801	Discontinued
0.7391	Intermediate Similarity	NPD2344	Approved
0.7391	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3751	Discontinued
0.7384	Intermediate Similarity	NPD919	Approved
0.7375	Intermediate Similarity	NPD1510	Phase 2
0.7374	Intermediate Similarity	NPD7808	Phase 3
0.7368	Intermediate Similarity	NPD1608	Approved
0.7362	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5711	Approved
0.7356	Intermediate Similarity	NPD7229	Phase 3
0.7356	Intermediate Similarity	NPD5710	Approved
0.7346	Intermediate Similarity	NPD1549	Phase 2
0.7342	Intermediate Similarity	NPD1240	Approved
0.7342	Intermediate Similarity	NPD943	Approved
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6777	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.7338	Intermediate Similarity	NPD1470	Approved
0.7333	Intermediate Similarity	NPD6799	Approved
0.7329	Intermediate Similarity	NPD2438	Suspended
0.7325	Intermediate Similarity	NPD6798	Discontinued
0.732	Intermediate Similarity	NPD7783	Phase 2
0.732	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7038	Approved
0.7318	Intermediate Similarity	NPD7240	Approved
0.7318	Intermediate Similarity	NPD7039	Approved
0.7308	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6674	Discontinued
0.7299	Intermediate Similarity	NPD1247	Approved
0.7296	Intermediate Similarity	NPD1933	Approved
0.7284	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7266	Discontinued
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD9545	Approved
0.7247	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1613	Approved
0.7233	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1551	Phase 2
0.7219	Intermediate Similarity	NPD1651	Approved
0.7219	Intermediate Similarity	NPD5691	Approved
0.7216	Intermediate Similarity	NPD5242	Approved
0.7216	Intermediate Similarity	NPD3926	Phase 2
0.7213	Intermediate Similarity	NPD8434	Phase 2
0.7212	Intermediate Similarity	NPD2309	Approved
0.7209	Intermediate Similarity	NPD5402	Approved
0.719	Intermediate Similarity	NPD1201	Approved
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7179	Intermediate Similarity	NPD7874	Approved
0.7179	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD17	Approved
0.716	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3787	Discontinued
0.7158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD7697	Approved
0.7135	Intermediate Similarity	NPD7698	Approved
0.7117	Intermediate Similarity	NPD6099	Approved
0.7117	Intermediate Similarity	NPD6100	Approved
0.7117	Intermediate Similarity	NPD2531	Phase 2
0.7107	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3268	Approved
0.7107	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD920	Approved
0.7095	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6823	Phase 2
0.7081	Intermediate Similarity	NPD6355	Discontinued
0.7078	Intermediate Similarity	NPD1611	Approved
0.7077	Intermediate Similarity	NPD7701	Phase 2
0.7074	Intermediate Similarity	NPD6534	Approved
0.7074	Intermediate Similarity	NPD6535	Approved
0.7063	Intermediate Similarity	NPD6233	Phase 2
0.7059	Intermediate Similarity	NPD1653	Approved
0.7051	Intermediate Similarity	NPD3225	Approved
0.7048	Intermediate Similarity	NPD4110	Phase 3
0.7048	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7680	Approved
0.7044	Intermediate Similarity	NPD7095	Approved
0.7044	Intermediate Similarity	NPD7008	Discontinued
0.7035	Intermediate Similarity	NPD6873	Phase 2
0.7019	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3620	Phase 2
0.7019	Intermediate Similarity	NPD4307	Phase 2
0.7018	Intermediate Similarity	NPD3455	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data