NPASS Compound

Structure

NPC126291 OpenBabel07101718322D 40 45 0 0 0 0 0 0 0 0999 V2000 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -4.3301 -1.5000 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 -3.4641 -1.0000 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 -6.0622 0.5000 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 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 -2.5981 0.5000 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 -6.0622 -1.5000 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 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 37 1 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 40 1 0 0 0 0 5 7 2 0 0 0 0 5 17 1 0 0 0 0 6 8 2 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 13 25 2 0 0 0 0 14 24 1 0 0 0 0 14 26 2 0 0 0 0 15 17 2 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 28 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 20 28 2 0 0 0 0 20 30 1 0 0 0 0 21 31 2 0 0 0 0 21 33 1 0 0 0 0 22 32 2 0 0 0 0 22 34 1 0 0 0 0 23 29 2 0 0 0 0 23 35 1 0 0 0 0 24 30 2 0 0 0 0 24 36 1 0 0 0 0 25 27 1 0 0 0 0 25 37 1 0 0 0 0 26 28 1 0 0 0 0 26 38 1 0 0 0 0 29 30 1 0 0 0 0 31 39 1 0 0 0 0 32 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.16
Volume:	544.101
LogP:	6.831
LogD:	3.746
LogS:	-6.612
# Rotatable Bonds:	5
TPSA:	117.84
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.177
Synthetic Accessibility Score:	2.772
Fsp3:	0.125
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.912
MDCK Permeability:	4.02741388825234e-05
Pgp-inhibitor:	0.206
Pgp-substrate:	0.052
Human Intestinal Absorption (HIA):	0.775
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.598

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	74.7582015991211%
Volume Distribution (VD):	0.398
Pgp-substrate:	11.598455429077148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.767
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.597
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.666
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	6.319
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.706
Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.921
Carcinogencity:	0.529
Eye Corrosion:	0.003
Eye Irritation:	0.937
Respiratory Toxicity:	0.275

Download Data

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

Natural Product: NPC126291

Natural Product ID:	NPC126291
*Common Name:**	PHYSWDUDIPIMOO-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PHYSWDUDIPIMOO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H26O8/c1-37-25-13-23(35)29(19-7-5-17-15(27(19)25)9-11-21(33)31(17)39-3)30-20-8-6-18-16(10-12-22(34)32(18)40-4)28(20)26(38-2)14-24(30)36/h5-14,33-36H,1-4H3
SMILES:	COc1cc(O)c(c2c1c1ccc(c(c1cc2)OC)O)c1c(O)cc(c2c1ccc1c2ccc(c1OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581376
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0003007] Phenanthrols

*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
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15686910]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	Fibrous Roots	n.a.	n.a.	PMID[25760525]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31415170]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10780	Bletilla striata	Species	Orchidaceae	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
MIC	8

Activity Type	# Activity
Cell Line	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	1000.0	nM	PMID[558498]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[558497]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[558497]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MIC	=	64.0	ug.mL-1	PMID[558497]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	8.0	ug.mL-1	PMID[558497]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	8.0	ug.mL-1	PMID[558497]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[558497]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	128.0	ug.mL-1	PMID[558497]

☑ 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 NPC126291 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	545
0.1-0.2	2070
0.2-0.3	6069
0.3-0.4	12058
0.4-0.5	5034
0.5-0.6	4280
0.6-0.7	7567
0.7-0.8	4237
0.8-0.85	557
0.85-0.9	187
0.9-0.95	81
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9786	High Similarity	NPC262297
0.9568	High Similarity	NPC183709
0.9429	High Similarity	NPC472087
0.9429	High Similarity	NPC472088
0.9424	High Similarity	NPC308768
0.9424	High Similarity	NPC12668
0.9357	High Similarity	NPC472089
0.9353	High Similarity	NPC218131
0.9353	High Similarity	NPC105847
0.9353	High Similarity	NPC220344
0.9353	High Similarity	NPC243996
0.9353	High Similarity	NPC275061
0.9353	High Similarity	NPC243759
0.9353	High Similarity	NPC132804
0.9348	High Similarity	NPC30632
0.9291	High Similarity	NPC175838
0.9286	High Similarity	NPC472092
0.9286	High Similarity	NPC273623
0.9286	High Similarity	NPC472090
0.9286	High Similarity	NPC472091
0.9281	High Similarity	NPC266006
0.9281	High Similarity	NPC22902
0.9281	High Similarity	NPC56329
0.9281	High Similarity	NPC151656
0.9281	High Similarity	NPC242715
0.9281	High Similarity	NPC200935
0.9281	High Similarity	NPC71465
0.9281	High Similarity	NPC266453
0.9281	High Similarity	NPC230919
0.9281	High Similarity	NPC472646
0.9275	High Similarity	NPC241241
0.9209	High Similarity	NPC472647
0.9209	High Similarity	NPC133463
0.9209	High Similarity	NPC472649
0.9209	High Similarity	NPC202846
0.9209	High Similarity	NPC170328
0.9209	High Similarity	NPC206525
0.9209	High Similarity	NPC472648
0.9209	High Similarity	NPC143139
0.9209	High Similarity	NPC191462
0.9149	High Similarity	NPC295719
0.9149	High Similarity	NPC165026
0.9149	High Similarity	NPC34431
0.9149	High Similarity	NPC73505
0.9137	High Similarity	NPC294884
0.9137	High Similarity	NPC258780
0.9137	High Similarity	NPC158142
0.9137	High Similarity	NPC10314
0.9137	High Similarity	NPC37410
0.9137	High Similarity	NPC200557
0.9137	High Similarity	NPC69029
0.9137	High Similarity	NPC108198
0.9078	High Similarity	NPC29868
0.9078	High Similarity	NPC79622
0.9078	High Similarity	NPC212942
0.9065	High Similarity	NPC160697
0.9065	High Similarity	NPC125649
0.9058	High Similarity	NPC303144
0.9054	High Similarity	NPC476391
0.9007	High Similarity	NPC90615
0.9007	High Similarity	NPC73535
0.9007	High Similarity	NPC272157
0.9007	High Similarity	NPC25111
0.9007	High Similarity	NPC6262
0.9007	High Similarity	NPC201145
0.9	High Similarity	NPC313081
0.898	High Similarity	NPC321657
0.898	High Similarity	NPC318373
0.898	High Similarity	NPC476969
0.8973	High Similarity	NPC174251
0.8973	High Similarity	NPC153182
0.8944	High Similarity	NPC230124
0.8944	High Similarity	NPC184613
0.8944	High Similarity	NPC6300
0.8944	High Similarity	NPC55947
0.8944	High Similarity	NPC114171
0.8936	High Similarity	NPC114155
0.8936	High Similarity	NPC300846
0.8936	High Similarity	NPC205442
0.8936	High Similarity	NPC476639
0.8933	High Similarity	NPC157333
0.8921	High Similarity	NPC228843
0.8919	High Similarity	NPC477612
0.8904	High Similarity	NPC274454
0.8904	High Similarity	NPC215678
0.8889	High Similarity	NPC277784
0.8865	High Similarity	NPC283009
0.8865	High Similarity	NPC111655
0.8865	High Similarity	NPC261873
0.8851	High Similarity	NPC211561
0.8849	High Similarity	NPC282508
0.8849	High Similarity	NPC149337
0.8849	High Similarity	NPC471983
0.8794	High Similarity	NPC209199
0.8794	High Similarity	NPC103967
0.8786	High Similarity	NPC161958
0.8786	High Similarity	NPC14224
0.8777	High Similarity	NPC126836
0.8777	High Similarity	NPC254000
0.8776	High Similarity	NPC233980
0.8776	High Similarity	NPC150714
0.8776	High Similarity	NPC95652
0.8759	High Similarity	NPC470917
0.875	High Similarity	NPC22317
0.875	High Similarity	NPC20520
0.875	High Similarity	NPC61783
0.875	High Similarity	NPC202104
0.8732	High Similarity	NPC256262
0.8723	High Similarity	NPC32778
0.8716	High Similarity	NPC204770
0.8716	High Similarity	NPC263940
0.8716	High Similarity	NPC18185
0.8716	High Similarity	NPC170103
0.8716	High Similarity	NPC474397
0.8716	High Similarity	NPC82917
0.8716	High Similarity	NPC108811
0.8716	High Similarity	NPC202742
0.8716	High Similarity	NPC262911
0.8716	High Similarity	NPC294558
0.8716	High Similarity	NPC236202
0.8716	High Similarity	NPC58190
0.8716	High Similarity	NPC70409
0.8714	High Similarity	NPC15543
0.8699	High Similarity	NPC469630
0.869	High Similarity	NPC265075
0.8675	High Similarity	NPC226809
0.8675	High Similarity	NPC279406
0.8667	High Similarity	NPC205501
0.8667	High Similarity	NPC162976
0.8667	High Similarity	NPC118000
0.8662	High Similarity	NPC141023
0.8662	High Similarity	NPC206737
0.8662	High Similarity	NPC7515
0.8662	High Similarity	NPC469659
0.8662	High Similarity	NPC66840
0.8662	High Similarity	NPC289258
0.8662	High Similarity	NPC256307
0.8662	High Similarity	NPC276026
0.8662	High Similarity	NPC56764
0.8662	High Similarity	NPC188378
0.8662	High Similarity	NPC555
0.8658	High Similarity	NPC227516
0.8658	High Similarity	NPC281549
0.8658	High Similarity	NPC20757
0.8652	High Similarity	NPC218884
0.8649	High Similarity	NPC96576
0.8639	High Similarity	NPC171932
0.8639	High Similarity	NPC304894
0.8639	High Similarity	NPC15659
0.8639	High Similarity	NPC469795
0.8639	High Similarity	NPC473108
0.8639	High Similarity	NPC28440
0.8633	High Similarity	NPC38017
0.8633	High Similarity	NPC23012
0.8633	High Similarity	NPC215300
0.8633	High Similarity	NPC28765
0.8633	High Similarity	NPC154866
0.8621	High Similarity	NPC262189
0.8621	High Similarity	NPC266650
0.8618	High Similarity	NPC224161
0.8611	High Similarity	NPC48956
0.8601	High Similarity	NPC55239
0.8601	High Similarity	NPC180602
0.8601	High Similarity	NPC214853
0.8601	High Similarity	NPC240279
0.8582	High Similarity	NPC471517
0.8582	High Similarity	NPC473309
0.8571	High Similarity	NPC163508
0.8571	High Similarity	NPC173203
0.8571	High Similarity	NPC471518
0.8571	High Similarity	NPC471519
0.8562	High Similarity	NPC46335
0.8561	High Similarity	NPC293054
0.8561	High Similarity	NPC169474
0.8561	High Similarity	NPC21563
0.8561	High Similarity	NPC53781
0.8561	High Similarity	NPC266555
0.8561	High Similarity	NPC471986
0.8561	High Similarity	NPC246620
0.8561	High Similarity	NPC236760
0.8561	High Similarity	NPC124452
0.8561	High Similarity	NPC324112
0.8561	High Similarity	NPC252131
0.8561	High Similarity	NPC74817
0.8561	High Similarity	NPC282000
0.8561	High Similarity	NPC159968
0.8561	High Similarity	NPC82679
0.8561	High Similarity	NPC236791
0.8553	High Similarity	NPC21902
0.8553	High Similarity	NPC157783
0.8552	High Similarity	NPC70682
0.8552	High Similarity	NPC260741
0.8552	High Similarity	NPC22517
0.8552	High Similarity	NPC32630
0.8542	High Similarity	NPC133025
0.8533	High Similarity	NPC329836
0.8531	High Similarity	NPC311256
0.8523	High Similarity	NPC260397
0.8523	High Similarity	NPC112251
0.8521	High Similarity	NPC73656

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 NPC126291 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	460
0.1-0.2	1022
0.2-0.3	1941
0.3-0.4	2808
0.4-0.5	1506
0.5-0.6	902
0.6-0.7	439
0.7-0.8	67
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.831	Intermediate Similarity	NPD3027	Phase 3
0.8112	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6232	Discontinued
0.8056	Intermediate Similarity	NPD4625	Phase 3
0.8042	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1613	Approved
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7473	Discontinued
0.7862	Intermediate Similarity	NPD4908	Phase 1
0.7791	Intermediate Similarity	NPD6959	Discontinued
0.7778	Intermediate Similarity	NPD6234	Discontinued
0.7725	Intermediate Similarity	NPD5844	Phase 1
0.7688	Intermediate Similarity	NPD37	Approved
0.7688	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3018	Phase 2
0.7665	Intermediate Similarity	NPD7228	Approved
0.7597	Intermediate Similarity	NPD6674	Discontinued
0.7558	Intermediate Similarity	NPD8053	Approved
0.7558	Intermediate Similarity	NPD8054	Approved
0.7546	Intermediate Similarity	NPD4965	Approved
0.7546	Intermediate Similarity	NPD4966	Approved
0.7546	Intermediate Similarity	NPD4967	Phase 2
0.7545	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6166	Phase 2
0.7533	Intermediate Similarity	NPD3620	Phase 2
0.7533	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2983	Phase 2
0.7517	Intermediate Similarity	NPD2982	Phase 2
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7484	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2981	Phase 2
0.7442	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1465	Phase 2
0.7423	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4749	Approved
0.7397	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1610	Phase 2
0.7365	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7199	Phase 2
0.7362	Intermediate Similarity	NPD1934	Approved
0.7358	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD5283	Phase 1
0.7338	Intermediate Similarity	NPD228	Approved
0.7326	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2801	Approved
0.7303	Intermediate Similarity	NPD4060	Phase 1
0.7285	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7768	Phase 2
0.7222	Intermediate Similarity	NPD1548	Phase 1
0.7215	Intermediate Similarity	NPD7003	Approved
0.7212	Intermediate Similarity	NPD8455	Phase 2
0.7208	Intermediate Similarity	NPD4097	Suspended
0.7184	Intermediate Similarity	NPD7240	Approved
0.7168	Intermediate Similarity	NPD7074	Phase 3
0.7162	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8099	Discontinued
0.7151	Intermediate Similarity	NPD8251	Approved
0.7151	Intermediate Similarity	NPD8252	Approved
0.7143	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3540	Phase 1
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7123	Intermediate Similarity	NPD4626	Approved
0.7117	Intermediate Similarity	NPD1653	Approved
0.7114	Intermediate Similarity	NPD6696	Suspended
0.711	Intermediate Similarity	NPD8156	Discontinued
0.711	Intermediate Similarity	NPD7054	Approved
0.7102	Intermediate Similarity	NPD8313	Approved
0.7102	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD2861	Phase 2
0.7083	Intermediate Similarity	NPD4055	Discovery
0.7081	Intermediate Similarity	NPD1511	Approved
0.7073	Intermediate Similarity	NPD4005	Discontinued
0.7071	Intermediate Similarity	NPD3022	Approved
0.7071	Intermediate Similarity	NPD3021	Approved
0.707	Intermediate Similarity	NPD3539	Phase 1
0.7069	Intermediate Similarity	NPD7472	Approved
0.7066	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2342	Discontinued
0.7039	Intermediate Similarity	NPD7906	Approved
0.7037	Intermediate Similarity	NPD7447	Phase 1
0.7027	Intermediate Similarity	NPD3705	Approved
0.7025	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3882	Suspended
0.7022	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7819	Suspended
0.7005	Intermediate Similarity	NPD7680	Approved
0.7	Intermediate Similarity	NPD8166	Discontinued
0.7	Intermediate Similarity	NPD8651	Approved
0.6994	Remote Similarity	NPD1512	Approved
0.6994	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6559	Discontinued
0.6982	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7212	Phase 2
0.6975	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7213	Phase 3
0.6975	Remote Similarity	NPD7041	Phase 2
0.6964	Remote Similarity	NPD3817	Phase 2
0.6962	Remote Similarity	NPD6100	Approved
0.6962	Remote Similarity	NPD5408	Approved
0.6962	Remote Similarity	NPD5404	Approved
0.6962	Remote Similarity	NPD5406	Approved
0.6962	Remote Similarity	NPD5405	Approved
0.6962	Remote Similarity	NPD6099	Approved
0.6957	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3818	Discontinued
0.6951	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4750	Phase 3
0.6949	Remote Similarity	NPD7808	Phase 3
0.6949	Remote Similarity	NPD7549	Discontinued
0.6939	Remote Similarity	NPD1651	Approved
0.6933	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6797	Phase 2
0.6923	Remote Similarity	NPD7635	Approved
0.6923	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7229	Phase 3
0.6919	Remote Similarity	NPD3787	Discontinued
0.6918	Remote Similarity	NPD7266	Discontinued
0.6911	Remote Similarity	NPD8151	Discontinued
0.6901	Remote Similarity	NPD5494	Approved
0.6894	Remote Similarity	NPD3750	Approved
0.6893	Remote Similarity	NPD7251	Discontinued
0.6887	Remote Similarity	NPD1283	Approved
0.6882	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8127	Discontinued
0.6859	Remote Similarity	NPD1558	Phase 1
0.6842	Remote Similarity	NPD3094	Phase 2
0.6839	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2533	Approved
0.6829	Remote Similarity	NPD2534	Approved
0.6829	Remote Similarity	NPD2532	Approved
0.6824	Remote Similarity	NPD5691	Approved
0.6818	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4578	Approved
0.6816	Remote Similarity	NPD4577	Approved
0.6816	Remote Similarity	NPD7312	Approved
0.6816	Remote Similarity	NPD7311	Approved
0.6816	Remote Similarity	NPD7310	Approved
0.6816	Remote Similarity	NPD7313	Approved
0.6815	Remote Similarity	NPD5735	Approved
0.6815	Remote Similarity	NPD3657	Discovery
0.681	Remote Similarity	NPD7124	Phase 2
0.68	Remote Similarity	NPD1611	Approved
0.6797	Remote Similarity	NPD4624	Approved
0.6796	Remote Similarity	NPD4663	Approved
0.679	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7411	Suspended
0.6784	Remote Similarity	NPD7075	Discontinued
0.6784	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7831	Phase 2
0.6784	Remote Similarity	NPD7833	Phase 2
0.6778	Remote Similarity	NPD7309	Approved
0.6772	Remote Similarity	NPD1607	Approved
0.677	Remote Similarity	NPD7037	Approved
0.6768	Remote Similarity	NPD4357	Discontinued
0.6766	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7458	Discontinued
0.676	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1398	Phase 1
0.675	Remote Similarity	NPD2438	Suspended
0.675	Remote Similarity	NPD2935	Discontinued
0.6743	Remote Similarity	NPD27	Approved
0.6743	Remote Similarity	NPD2489	Approved
0.6735	Remote Similarity	NPD7340	Approved
0.6731	Remote Similarity	NPD5111	Phase 2
0.6731	Remote Similarity	NPD5109	Approved
0.6731	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5110	Phase 2
0.673	Remote Similarity	NPD4536	Approved
0.673	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4538	Approved
0.6728	Remote Similarity	NPD5177	Phase 3
0.6727	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4678	Approved
0.6726	Remote Similarity	NPD4675	Approved
0.6725	Remote Similarity	NPD6788	Approved
0.6725	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3051	Approved
0.6711	Remote Similarity	NPD1669	Approved
0.6709	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5124	Phase 1
0.6708	Remote Similarity	NPD5763	Approved
0.6708	Remote Similarity	NPD5762	Approved
0.6706	Remote Similarity	NPD5929	Approved
0.6705	Remote Similarity	NPD6746	Phase 2
0.6691	Remote Similarity	NPD940	Approved
0.6691	Remote Similarity	NPD846	Approved
0.669	Remote Similarity	NPD7843	Approved
0.6689	Remote Similarity	NPD1281	Approved
0.6689	Remote Similarity	NPD5536	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