NPASS Compound

Structure

NPC472647 OpenBabel07101718222D 37 42 0 0 0 0 0 0 0 0999 V2000 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 5.1962 -3.0000 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 -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 -1.7321 -0.0000 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 4.3301 -4.5000 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 2.5981 -4.5000 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 1.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 3.4641 -5.0000 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 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 2.5981 -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 2.5981 -3.5000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 3.4641 1.0000 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 2.5981 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 3.4641 -6.0000 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 1 35 1 0 0 0 0 2 36 1 0 0 0 0 3 37 1 0 0 0 0 4 5 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 8 2 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 7 19 2 0 0 0 0 8 22 1 0 0 0 0 9 21 2 0 0 0 0 10 16 2 0 0 0 0 10 19 1 0 0 0 0 11 18 2 0 0 0 0 11 20 1 0 0 0 0 12 17 2 0 0 0 0 12 25 1 0 0 0 0 13 20 2 0 0 0 0 13 26 1 0 0 0 0 14 23 2 0 0 0 0 14 24 1 0 0 0 0 15 27 2 0 0 0 0 15 28 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 29 1 0 0 0 0 19 35 1 0 0 0 0 20 36 1 0 0 0 0 21 31 1 0 0 0 0 22 30 2 0 0 0 0 22 31 1 0 0 0 0 23 29 1 0 0 0 0 24 25 2 0 0 0 0 24 30 1 0 0 0 0 25 32 1 0 0 0 0 26 29 2 0 0 0 0 26 33 1 0 0 0 0 27 30 1 0 0 0 0 27 34 1 0 0 0 0 28 31 2 0 0 0 0 28 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.17
Volume:	511.861
LogP:	7.267
LogD:	3.949
LogS:	-7.89
# Rotatable Bonds:	4
TPSA:	88.38
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	2.804
Fsp3:	0.161
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.64
MDCK Permeability:	1.3907697393733542e-05
Pgp-inhibitor:	0.636
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.676
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	95.34969329833984%
Volume Distribution (VD):	0.592
Pgp-substrate:	1.5129085779190063%

ADMET: Metabolism

CYP1A2-inhibitor:	0.866
CYP1A2-substrate:	0.878
CYP2C19-inhibitor:	0.894
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.577
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.087
CYP2D6-substrate:	0.962
CYP3A4-inhibitor:	0.238
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	5.894
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.137
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.478
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.856
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.885
Respiratory Toxicity:	0.39

Download Data

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

Natural Product: NPC472647

Natural Product ID:	NPC472647
*Common Name:**	RTUIXFQVMUYSJQ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RTUIXFQVMUYSJQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C31H26O6/c1-35-19-7-9-21-16(10-19)6-8-22-30(27(34)15-28(37-3)31(21)22)24-14-23-17(12-25(24)32)4-5-18-11-20(36-2)13-26(33)29(18)23/h6-15,32-34H,4-5H2,1-3H3
SMILES:	COC1=CC2=C(C=C1)C3=C(C=C(C(=C3C=C2)C4=C(C=C5CCC6=C(C5=C4)C(=CC(=C6)OC)O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581373
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
MIC	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[549480]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MIC	=	64.0	ug.mL-1	PMID[549480]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	8.0	ug.mL-1	PMID[549480]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	16.0	ug.mL-1	PMID[549480]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[549480]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	128.0	ug.mL-1	PMID[549480]

☑ 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 NPC472647 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	484
0.1-0.2	2009
0.2-0.3	4963
0.3-0.4	12570
0.4-0.5	5312
0.5-0.6	4422
0.6-0.7	8224
0.7-0.8	3995
0.8-0.85	497
0.85-0.9	152
0.9-0.95	39
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC191462
1.0	High Similarity	NPC133463
1.0	High Similarity	NPC472648
1.0	High Similarity	NPC472649
1.0	High Similarity	NPC206525
1.0	High Similarity	NPC170328
0.9923	High Similarity	NPC472646
0.9923	High Similarity	NPC71465
0.9922	High Similarity	NPC37410
0.9922	High Similarity	NPC258780
0.9773	High Similarity	NPC273623
0.9612	High Similarity	NPC282508
0.9535	High Similarity	NPC254000
0.938	High Similarity	NPC215300
0.938	High Similarity	NPC38017
0.9308	High Similarity	NPC471518
0.9308	High Similarity	NPC471519
0.9302	High Similarity	NPC53781
0.9225	High Similarity	NPC170485
0.9209	High Similarity	NPC126291
0.9197	High Similarity	NPC183709
0.9185	High Similarity	NPC266006
0.9167	High Similarity	NPC471517
0.9167	High Similarity	NPC473309
0.9154	High Similarity	NPC473221
0.9147	High Similarity	NPC113495
0.9147	High Similarity	NPC105031
0.9147	High Similarity	NPC105718
0.9147	High Similarity	NPC278955
0.9143	High Similarity	NPC262297
0.9077	High Similarity	NPC82299
0.9071	High Similarity	NPC274454
0.9071	High Similarity	NPC215678
0.907	High Similarity	NPC228503
0.907	High Similarity	NPC138248
0.9051	High Similarity	NPC308768
0.9051	High Similarity	NPC12668
0.9037	High Similarity	NPC472370
0.9007	High Similarity	NPC174251
0.9007	High Similarity	NPC153182
0.8978	High Similarity	NPC218131
0.8978	High Similarity	NPC105847
0.8978	High Similarity	NPC243996
0.8978	High Similarity	NPC243759
0.8978	High Similarity	NPC132804
0.8978	High Similarity	NPC220344
0.8978	High Similarity	NPC275061
0.8921	High Similarity	NPC175838
0.8905	High Similarity	NPC230919
0.8905	High Similarity	NPC266453
0.8905	High Similarity	NPC200935
0.8905	High Similarity	NPC56329
0.8905	High Similarity	NPC22902
0.8905	High Similarity	NPC151656
0.8905	High Similarity	NPC242715
0.8889	High Similarity	NPC469610
0.8881	High Similarity	NPC8899
0.8881	High Similarity	NPC160623
0.8849	High Similarity	NPC472089
0.8837	High Similarity	NPC476633
0.8832	High Similarity	NPC202846
0.8832	High Similarity	NPC143139
0.8832	High Similarity	NPC30632
0.8832	High Similarity	NPC141717
0.8832	High Similarity	NPC205442
0.8828	High Similarity	NPC476391
0.8819	High Similarity	NPC118000
0.8819	High Similarity	NPC205501
0.8819	High Similarity	NPC162976
0.8815	High Similarity	NPC303144
0.8815	High Similarity	NPC469611
0.8803	High Similarity	NPC14468
0.8786	High Similarity	NPC472088
0.8786	High Similarity	NPC472087
0.8777	High Similarity	NPC295719
0.8777	High Similarity	NPC165026
0.8777	High Similarity	NPC73505
0.8777	High Similarity	NPC34431
0.876	High Similarity	NPC102639
0.8759	High Similarity	NPC11727
0.8759	High Similarity	NPC200557
0.8759	High Similarity	NPC241241
0.8759	High Similarity	NPC15109
0.8759	High Similarity	NPC10314
0.8759	High Similarity	NPC158142
0.8759	High Similarity	NPC111655
0.8759	High Similarity	NPC69029
0.8759	High Similarity	NPC108198
0.8759	High Similarity	NPC125579
0.8759	High Similarity	NPC294884
0.8741	High Similarity	NPC149337
0.8741	High Similarity	NPC471983
0.8731	High Similarity	NPC16577
0.8705	High Similarity	NPC212942
0.8705	High Similarity	NPC29868
0.8705	High Similarity	NPC79622
0.8699	High Similarity	NPC120633
0.8699	High Similarity	NPC473018
0.8696	High Similarity	NPC471522
0.8686	High Similarity	NPC71372
0.8686	High Similarity	NPC160697
0.8686	High Similarity	NPC125649
0.8686	High Similarity	NPC473107
0.8682	High Similarity	NPC103916
0.8643	High Similarity	NPC174787
0.8643	High Similarity	NPC213607
0.8643	High Similarity	NPC472090
0.8643	High Similarity	NPC472092
0.8643	High Similarity	NPC182509
0.8643	High Similarity	NPC20520
0.8643	High Similarity	NPC472091
0.8643	High Similarity	NPC61783
0.8633	High Similarity	NPC90615
0.8633	High Similarity	NPC470308
0.8633	High Similarity	NPC272157
0.8633	High Similarity	NPC470307
0.8633	High Similarity	NPC201145
0.8633	High Similarity	NPC25111
0.8633	High Similarity	NPC73535
0.8633	High Similarity	NPC6262
0.8626	High Similarity	NPC77789
0.8626	High Similarity	NPC18128
0.8623	High Similarity	NPC313081
0.8611	High Similarity	NPC112819
0.8611	High Similarity	NPC133209
0.8611	High Similarity	NPC6702
0.8611	High Similarity	NPC111134
0.8605	High Similarity	NPC184302
0.8603	High Similarity	NPC238168
0.8603	High Similarity	NPC472590
0.8603	High Similarity	NPC237424
0.8603	High Similarity	NPC15543
0.8593	High Similarity	NPC222108
0.8593	High Similarity	NPC96719
0.8582	High Similarity	NPC46978
0.8582	High Similarity	NPC265075
0.8571	High Similarity	NPC184613
0.8571	High Similarity	NPC293801
0.8571	High Similarity	NPC55947
0.8562	High Similarity	NPC218801
0.8561	High Similarity	NPC300846
0.8561	High Similarity	NPC476639
0.8561	High Similarity	NPC114155
0.8551	High Similarity	NPC476617
0.8551	High Similarity	NPC476615
0.8551	High Similarity	NPC476616
0.854	High Similarity	NPC218884
0.854	High Similarity	NPC228843
0.8531	High Similarity	NPC36732
0.8529	High Similarity	NPC472369
0.8527	High Similarity	NPC190514
0.8527	High Similarity	NPC131118
0.8527	High Similarity	NPC63010
0.8521	High Similarity	NPC186033
0.8519	High Similarity	NPC38664
0.8519	High Similarity	NPC53986
0.8507	High Similarity	NPC9292
0.8507	High Similarity	NPC145659
0.8493	Intermediate Similarity	NPC122980
0.8493	Intermediate Similarity	NPC177172
0.8493	Intermediate Similarity	NPC107862
0.8493	Intermediate Similarity	NPC148516
0.8493	Intermediate Similarity	NPC180605
0.8489	Intermediate Similarity	NPC261873
0.8489	Intermediate Similarity	NPC283009
0.8478	Intermediate Similarity	NPC77196
0.8473	Intermediate Similarity	NPC277798
0.8473	Intermediate Similarity	NPC100108
0.8473	Intermediate Similarity	NPC129176
0.8472	Intermediate Similarity	NPC149633
0.8467	Intermediate Similarity	NPC211413
0.8467	Intermediate Similarity	NPC68205
0.8467	Intermediate Similarity	NPC164804
0.8467	Intermediate Similarity	NPC244888
0.8467	Intermediate Similarity	NPC293203
0.8467	Intermediate Similarity	NPC118683
0.8462	Intermediate Similarity	NPC173203
0.8462	Intermediate Similarity	NPC163508
0.8456	Intermediate Similarity	NPC93962
0.8456	Intermediate Similarity	NPC134360
0.8451	Intermediate Similarity	NPC100482
0.8451	Intermediate Similarity	NPC277331
0.845	Intermediate Similarity	NPC299180
0.845	Intermediate Similarity	NPC221549
0.845	Intermediate Similarity	NPC195466
0.845	Intermediate Similarity	NPC474933
0.845	Intermediate Similarity	NPC50521
0.845	Intermediate Similarity	NPC69261
0.845	Intermediate Similarity	NPC244816
0.845	Intermediate Similarity	NPC33270
0.8444	Intermediate Similarity	NPC471986
0.844	Intermediate Similarity	NPC32630
0.844	Intermediate Similarity	NPC230124
0.844	Intermediate Similarity	NPC114171
0.844	Intermediate Similarity	NPC6300
0.8433	Intermediate Similarity	NPC133407
0.8433	Intermediate Similarity	NPC28476
0.8421	Intermediate Similarity	NPC472052
0.8421	Intermediate Similarity	NPC470342
0.8421	Intermediate Similarity	NPC472060

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 NPC472647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	1034
0.2-0.3	1556
0.3-0.4	2816
0.4-0.5	1713
0.5-0.6	989
0.6-0.7	518
0.7-0.8	94
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8731	High Similarity	NPD4625	Phase 3
0.8667	High Similarity	NPD4907	Clinical (unspecified phase)
0.8519	High Similarity	NPD4908	Phase 1
0.8129	Intermediate Similarity	NPD6959	Discontinued
0.8015	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD4749	Approved
0.8	Intermediate Similarity	NPD1610	Phase 2
0.7973	Intermediate Similarity	NPD7390	Discontinued
0.7971	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3027	Phase 3
0.7872	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6232	Discontinued
0.7836	Intermediate Similarity	NPD1548	Phase 1
0.7823	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4097	Suspended
0.777	Intermediate Similarity	NPD7003	Approved
0.7762	Intermediate Similarity	NPD1613	Approved
0.7762	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD4626	Approved
0.7702	Intermediate Similarity	NPD7473	Discontinued
0.7674	Intermediate Similarity	NPD2342	Discontinued
0.766	Intermediate Similarity	NPD2861	Phase 2
0.7643	Intermediate Similarity	NPD7768	Phase 2
0.7607	Intermediate Similarity	NPD5844	Phase 1
0.7571	Intermediate Similarity	NPD6696	Suspended
0.7566	Intermediate Similarity	NPD7447	Phase 1
0.7557	Intermediate Similarity	NPD4750	Phase 3
0.7519	Intermediate Similarity	NPD7635	Approved
0.7518	Intermediate Similarity	NPD1651	Approved
0.7517	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6099	Approved
0.75	Intermediate Similarity	NPD7041	Phase 2
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD7213	Phase 3
0.75	Intermediate Similarity	NPD7212	Phase 2
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7452	Intermediate Similarity	NPD37	Approved
0.7451	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1283	Approved
0.7423	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3750	Approved
0.7413	Intermediate Similarity	NPD3018	Phase 2
0.7407	Intermediate Similarity	NPD7229	Phase 3
0.7391	Intermediate Similarity	NPD5691	Approved
0.7379	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1611	Approved
0.7351	Intermediate Similarity	NPD6674	Discontinued
0.7343	Intermediate Similarity	NPD4624	Approved
0.7338	Intermediate Similarity	NPD2532	Approved
0.7338	Intermediate Similarity	NPD2534	Approved
0.7338	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2533	Approved
0.7329	Intermediate Similarity	NPD6234	Discontinued
0.7312	Intermediate Similarity	NPD4967	Phase 2
0.7312	Intermediate Similarity	NPD4966	Approved
0.7312	Intermediate Similarity	NPD4965	Approved
0.7303	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1607	Approved
0.7296	Intermediate Similarity	NPD7819	Suspended
0.7296	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD940	Approved
0.7287	Intermediate Similarity	NPD846	Approved
0.7285	Intermediate Similarity	NPD7037	Approved
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7261	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2982	Phase 2
0.7254	Intermediate Similarity	NPD1669	Approved
0.7254	Intermediate Similarity	NPD2983	Phase 2
0.7234	Intermediate Similarity	NPD1281	Approved
0.7234	Intermediate Similarity	NPD422	Phase 1
0.723	Intermediate Similarity	NPD5124	Phase 1
0.723	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7228	Approved
0.7226	Intermediate Similarity	NPD6671	Approved
0.7222	Intermediate Similarity	NPD6584	Phase 3
0.7215	Intermediate Similarity	NPD4380	Phase 2
0.7214	Intermediate Similarity	NPD2286	Discontinued
0.7209	Intermediate Similarity	NPD1242	Phase 1
0.7206	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5283	Phase 1
0.7206	Intermediate Similarity	NPD1398	Phase 1
0.72	Intermediate Similarity	NPD1510	Phase 2
0.72	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3892	Phase 2
0.7188	Intermediate Similarity	NPD8455	Phase 2
0.7183	Intermediate Similarity	NPD2981	Phase 2
0.7178	Intermediate Similarity	NPD6746	Phase 2
0.7174	Intermediate Similarity	NPD7340	Approved
0.7171	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7411	Suspended
0.7168	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5451	Approved
0.7162	Intermediate Similarity	NPD3620	Phase 2
0.7162	Intermediate Similarity	NPD1240	Approved
0.7162	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2979	Phase 3
0.7162	Intermediate Similarity	NPD2238	Phase 2
0.716	Intermediate Similarity	NPD3749	Approved
0.7153	Intermediate Similarity	NPD3094	Phase 2
0.7135	Intermediate Similarity	NPD8054	Approved
0.7135	Intermediate Similarity	NPD8053	Approved
0.7133	Intermediate Similarity	NPD5327	Phase 3
0.7115	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5735	Approved
0.7108	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6166	Phase 2
0.7101	Intermediate Similarity	NPD709	Approved
0.7099	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3748	Approved
0.7086	Intermediate Similarity	NPD4108	Discontinued
0.7083	Intermediate Similarity	NPD8651	Approved
0.7078	Intermediate Similarity	NPD7466	Approved
0.7076	Intermediate Similarity	NPD8313	Approved
0.7076	Intermediate Similarity	NPD8312	Approved
0.7071	Intermediate Similarity	NPD3091	Approved
0.7063	Intermediate Similarity	NPD2232	Approved
0.7063	Intermediate Similarity	NPD2233	Approved
0.7063	Intermediate Similarity	NPD2230	Approved
0.7059	Intermediate Similarity	NPD6559	Discontinued
0.7047	Intermediate Similarity	NPD4140	Approved
0.7044	Intermediate Similarity	NPD7458	Discontinued
0.7044	Intermediate Similarity	NPD3226	Approved
0.703	Intermediate Similarity	NPD7199	Phase 2
0.7024	Intermediate Similarity	NPD7177	Discontinued
0.7019	Intermediate Similarity	NPD1934	Approved
0.7014	Intermediate Similarity	NPD6582	Phase 2
0.7014	Intermediate Similarity	NPD6583	Phase 3
0.7013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3020	Approved
0.6993	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3092	Approved
0.6993	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3787	Discontinued
0.6975	Remote Similarity	NPD2801	Approved
0.6975	Remote Similarity	NPD5929	Approved
0.6957	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6353	Approved
0.6948	Remote Similarity	NPD1549	Phase 2
0.6946	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1511	Approved
0.6937	Remote Similarity	NPD4005	Discontinued
0.6934	Remote Similarity	NPD228	Approved
0.6928	Remote Similarity	NPD2438	Suspended
0.6923	Remote Similarity	NPD8099	Discontinued
0.6923	Remote Similarity	NPD8252	Approved
0.6923	Remote Similarity	NPD8251	Approved
0.6918	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3022	Approved
0.6912	Remote Similarity	NPD3021	Approved
0.6908	Remote Similarity	NPD4538	Approved
0.6908	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4536	Approved
0.6906	Remote Similarity	NPD497	Approved
0.6901	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD844	Approved
0.6899	Remote Similarity	NPD2859	Approved
0.6899	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2860	Approved
0.6893	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5535	Approved
0.6883	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5762	Approved
0.6883	Remote Similarity	NPD2346	Discontinued
0.6883	Remote Similarity	NPD3540	Phase 1
0.6883	Remote Similarity	NPD5763	Approved
0.6882	Remote Similarity	NPD8156	Discontinued
0.6875	Remote Similarity	NPD3705	Approved
0.6871	Remote Similarity	NPD1465	Phase 2
0.686	Remote Similarity	NPD7240	Approved
0.6855	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1512	Approved
0.6855	Remote Similarity	NPD6090	Discontinued
0.6855	Remote Similarity	NPD4319	Phase 2
0.6853	Remote Similarity	NPD4059	Approved
0.6853	Remote Similarity	NPD5125	Phase 3
0.6853	Remote Similarity	NPD5126	Approved
0.6853	Remote Similarity	NPD3095	Discontinued
0.6853	Remote Similarity	NPD3019	Approved
0.6848	Remote Similarity	NPD7075	Discontinued
0.6848	Remote Similarity	NPD4055	Discovery
0.6846	Remote Similarity	NPD7095	Approved
0.6846	Remote Similarity	NPD288	Approved
0.6845	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD496	Approved
0.6835	Remote Similarity	NPD495	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