NPASS Compound

Structure

NPC31097 OpenBabel07101718292D 39 45 0 0 1 0 0 0 0 0999 V2000 -1.3383 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6766 1.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2939 2.9114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0522 -1.6202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -0.6420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7029 -2.1908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6906 -2.0344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0736 -1.4137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0490 -1.1008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9780 2.8251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9780 2.8251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9780 0.4109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4320 -0.4801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9780 0.4109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4197 -0.3236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 2.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6851 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 0.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6851 2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5761 0.6640 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 2.1180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 1.1180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 3.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -0.3820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 2.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 30 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 19 2 0 0 0 0 12 21 2 0 0 0 0 13 22 2 0 0 0 0 14 23 2 0 0 0 0 15 16 2 0 0 0 0 15 30 1 0 0 0 0 16 34 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 18 32 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 20 26 2 0 0 0 0 21 23 1 0 0 0 0 21 32 1 0 0 0 0 22 33 1 0 0 0 0 23 36 1 0 0 0 0 24 28 1 0 0 0 0 24 34 1 0 0 0 0 25 18 1 6 0 0 0 25 27 1 0 0 0 0 25 35 1 0 0 0 0 26 30 1 0 0 0 0 26 33 1 0 0 0 0 27 34 1 0 0 0 0 27 37 2 0 0 0 0 28 35 1 0 0 0 0 28 38 2 0 0 0 0 29 32 1 6 0 0 0 29 35 1 0 0 0 0 29 36 1 0 0 0 0 31 36 1 0 0 0 0 32 39 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.25
Volume:	540.853
LogP:	5.482
LogD:	4.285
LogS:	-5.638
# Rotatable Bonds:	2
TPSA:	79.88
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	4.818
Fsp3:	0.312
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.34
MDCK Permeability:	2.663271880010143e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.093
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.796

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	98.8159408569336%
Volume Distribution (VD):	1.087
Pgp-substrate:	1.112882137298584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.961
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.968
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.903
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.979
CYP3A4-substrate:	0.938

ADMET: Excretion

Clearance (CL):	2.869
Half-life (T1/2):	0.111

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.852
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.417
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.893
Carcinogencity:	0.897
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC31097

Natural Product ID:	NPC31097
*Common Name:**	Okaramine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XOYCJCSLHCTYSV-HTFKTHENSA-N
Standard InCHI:	InChI=1S/C32H32N4O3/c1-6-31(4,5)36-23-14-10-8-12-21(23)32(39)18-25-27(37)34-16-15-30(2,3)26-20(19-11-7-9-13-22(19)33-26)17-24(34)28(38)35(25)29(32)36/h6-17,25,29,33,39H,1,18H2,2-5H3/b16-15-,24-17-/t25-,29-,32-/m1/s1
SMILES:	C=CC(N1c2ccccc2[C@]2([C@@H]1N1[C@H](C2)C(=O)N2C(=Cc3c4ccccc4[nH]c3C(C=C2)(C)C)C1=O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509244
PubChem CID:	5387493
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075772]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16155971]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19824618]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21667999]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[324959]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	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
LD50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3978	Organism	Bombyx mori	Bombyx mori	LD50	=	8.0	ug	PMID[481411]
NPT3978	Organism	Bombyx mori	Bombyx mori	LD50	=	8.0	mg.kg-1	PMID[481412]

☑ 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 NPC31097 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	409
0.1-0.2	2007
0.2-0.3	12142
0.3-0.4	19174
0.4-0.5	3837
0.5-0.6	2786
0.6-0.7	1933
0.7-0.8	394
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9949	High Similarity	NPC474896
0.9798	High Similarity	NPC272174
0.8869	High Similarity	NPC14812
0.8227	Intermediate Similarity	NPC477177
0.8182	Intermediate Similarity	NPC470730
0.8182	Intermediate Similarity	NPC477176
0.8182	Intermediate Similarity	NPC477175
0.8182	Intermediate Similarity	NPC470729
0.8145	Intermediate Similarity	NPC474877
0.8145	Intermediate Similarity	NPC475969
0.8145	Intermediate Similarity	NPC475859
0.8108	Intermediate Similarity	NPC165743
0.8072	Intermediate Similarity	NPC63279
0.8036	Intermediate Similarity	NPC297642
0.7963	Intermediate Similarity	NPC470731
0.7963	Intermediate Similarity	NPC470732
0.7857	Intermediate Similarity	NPC471944
0.7767	Intermediate Similarity	NPC162860
0.7757	Intermediate Similarity	NPC54420
0.7719	Intermediate Similarity	NPC325976
0.7714	Intermediate Similarity	NPC171317
0.7689	Intermediate Similarity	NPC476491
0.7673	Intermediate Similarity	NPC91179
0.7659	Intermediate Similarity	NPC94752
0.7653	Intermediate Similarity	NPC471436
0.7647	Intermediate Similarity	NPC477714
0.7634	Intermediate Similarity	NPC476817
0.7621	Intermediate Similarity	NPC326363
0.7602	Intermediate Similarity	NPC477715
0.76	Intermediate Similarity	NPC161861
0.7591	Intermediate Similarity	NPC478157
0.7561	Intermediate Similarity	NPC472294
0.7523	Intermediate Similarity	NPC478158
0.7522	Intermediate Similarity	NPC19170
0.75	Intermediate Similarity	NPC473376
0.7489	Intermediate Similarity	NPC473310
0.7488	Intermediate Similarity	NPC141612
0.7488	Intermediate Similarity	NPC135601
0.7488	Intermediate Similarity	NPC17273
0.7477	Intermediate Similarity	NPC322064
0.7452	Intermediate Similarity	NPC17059
0.7442	Intermediate Similarity	NPC300183
0.7434	Intermediate Similarity	NPC312942
0.7434	Intermediate Similarity	NPC327095
0.7427	Intermediate Similarity	NPC470205
0.7424	Intermediate Similarity	NPC191382
0.7424	Intermediate Similarity	NPC297862
0.7424	Intermediate Similarity	NPC56109
0.7424	Intermediate Similarity	NPC33949
0.7418	Intermediate Similarity	NPC232130
0.7416	Intermediate Similarity	NPC213629
0.7411	Intermediate Similarity	NPC281049
0.7401	Intermediate Similarity	NPC40455
0.7391	Intermediate Similarity	NPC69843
0.7391	Intermediate Similarity	NPC228835
0.7383	Intermediate Similarity	NPC131887
0.7376	Intermediate Similarity	NPC82370
0.7371	Intermediate Similarity	NPC472539
0.7371	Intermediate Similarity	NPC472540
0.7371	Intermediate Similarity	NPC470787
0.7364	Intermediate Similarity	NPC107077
0.7364	Intermediate Similarity	NPC223791
0.7357	Intermediate Similarity	NPC155444
0.7356	Intermediate Similarity	NPC133003
0.7354	Intermediate Similarity	NPC477979
0.7352	Intermediate Similarity	NPC166492
0.7352	Intermediate Similarity	NPC270918
0.7352	Intermediate Similarity	NPC473362
0.735	Intermediate Similarity	NPC28945
0.7349	Intermediate Similarity	NPC293917
0.7342	Intermediate Similarity	NPC75634
0.7336	Intermediate Similarity	NPC24370
0.7336	Intermediate Similarity	NPC141454
0.7336	Intermediate Similarity	NPC319232
0.7336	Intermediate Similarity	NPC472542
0.7336	Intermediate Similarity	NPC472541
0.7333	Intermediate Similarity	NPC303658
0.7328	Intermediate Similarity	NPC89987
0.7325	Intermediate Similarity	NPC229893
0.7319	Intermediate Similarity	NPC470784
0.7318	Intermediate Similarity	NPC71238
0.7318	Intermediate Similarity	NPC270241
0.7314	Intermediate Similarity	NPC314882
0.7309	Intermediate Similarity	NPC54744
0.7306	Intermediate Similarity	NPC277350
0.7297	Intermediate Similarity	NPC54981
0.7297	Intermediate Similarity	NPC320968
0.7296	Intermediate Similarity	NPC284888
0.7296	Intermediate Similarity	NPC220852
0.7294	Intermediate Similarity	NPC476098
0.7294	Intermediate Similarity	NPC165599
0.7289	Intermediate Similarity	NPC472285
0.7289	Intermediate Similarity	NPC305984
0.7282	Intermediate Similarity	NPC11126
0.7282	Intermediate Similarity	NPC219336
0.7281	Intermediate Similarity	NPC253987
0.7281	Intermediate Similarity	NPC475506
0.7277	Intermediate Similarity	NPC285343
0.7273	Intermediate Similarity	NPC194740
0.7273	Intermediate Similarity	NPC471155
0.7269	Intermediate Similarity	NPC100321
0.7261	Intermediate Similarity	NPC214142
0.7261	Intermediate Similarity	NPC909
0.7261	Intermediate Similarity	NPC475338
0.7257	Intermediate Similarity	NPC475736
0.7252	Intermediate Similarity	NPC475422
0.7249	Intermediate Similarity	NPC64216
0.7248	Intermediate Similarity	NPC155143
0.7246	Intermediate Similarity	NPC470785
0.7246	Intermediate Similarity	NPC41679
0.7235	Intermediate Similarity	NPC252338
0.7233	Intermediate Similarity	NPC15573
0.7233	Intermediate Similarity	NPC183662
0.7233	Intermediate Similarity	NPC217372
0.723	Intermediate Similarity	NPC471386
0.7229	Intermediate Similarity	NPC475258
0.7229	Intermediate Similarity	NPC261251
0.7229	Intermediate Similarity	NPC124920
0.7229	Intermediate Similarity	NPC315467
0.7229	Intermediate Similarity	NPC34580
0.7229	Intermediate Similarity	NPC118559
0.7229	Intermediate Similarity	NPC304307
0.7227	Intermediate Similarity	NPC225400
0.7222	Intermediate Similarity	NPC473640
0.7217	Intermediate Similarity	NPC324091
0.7215	Intermediate Similarity	NPC98715
0.7215	Intermediate Similarity	NPC317701
0.7203	Intermediate Similarity	NPC184680
0.7203	Intermediate Similarity	NPC184225
0.7202	Intermediate Similarity	NPC153400
0.72	Intermediate Similarity	NPC250835
0.7198	Intermediate Similarity	NPC100547
0.7195	Intermediate Similarity	NPC470786
0.7195	Intermediate Similarity	NPC244741
0.7195	Intermediate Similarity	NPC478006
0.7195	Intermediate Similarity	NPC472538
0.7188	Intermediate Similarity	NPC153980
0.7188	Intermediate Similarity	NPC471193
0.7188	Intermediate Similarity	NPC6865
0.7188	Intermediate Similarity	NPC471194
0.7186	Intermediate Similarity	NPC299594
0.7183	Intermediate Similarity	NPC473763
0.7183	Intermediate Similarity	NPC117244
0.717	Intermediate Similarity	NPC321708
0.717	Intermediate Similarity	NPC221873
0.7167	Intermediate Similarity	NPC322135
0.7167	Intermediate Similarity	NPC223409
0.7167	Intermediate Similarity	NPC95240
0.7163	Intermediate Similarity	NPC195239
0.7163	Intermediate Similarity	NPC16659
0.7163	Intermediate Similarity	NPC157828
0.7162	Intermediate Similarity	NPC87755
0.7156	Intermediate Similarity	NPC478077
0.7156	Intermediate Similarity	NPC214428
0.7155	Intermediate Similarity	NPC171393
0.7155	Intermediate Similarity	NPC295452
0.7155	Intermediate Similarity	NPC6215
0.715	Intermediate Similarity	NPC471122
0.7149	Intermediate Similarity	NPC471191
0.7149	Intermediate Similarity	NPC323752
0.7143	Intermediate Similarity	NPC265576
0.7143	Intermediate Similarity	NPC476818
0.7143	Intermediate Similarity	NPC72956
0.7137	Intermediate Similarity	NPC14288
0.7137	Intermediate Similarity	NPC312645
0.7131	Intermediate Similarity	NPC478010
0.7131	Intermediate Similarity	NPC478009
0.713	Intermediate Similarity	NPC11445
0.713	Intermediate Similarity	NPC220851
0.7129	Intermediate Similarity	NPC476118
0.7126	Intermediate Similarity	NPC321939
0.7125	Intermediate Similarity	NPC477108
0.7125	Intermediate Similarity	NPC477109
0.7125	Intermediate Similarity	NPC477107
0.7117	Intermediate Similarity	NPC225821
0.7117	Intermediate Similarity	NPC243850
0.7117	Intermediate Similarity	NPC46225
0.7115	Intermediate Similarity	NPC265710
0.7111	Intermediate Similarity	NPC75726
0.7111	Intermediate Similarity	NPC31385
0.7111	Intermediate Similarity	NPC110602
0.7109	Intermediate Similarity	NPC307396
0.7106	Intermediate Similarity	NPC63031
0.7106	Intermediate Similarity	NPC321592
0.7106	Intermediate Similarity	NPC54803
0.7105	Intermediate Similarity	NPC264285
0.7103	Intermediate Similarity	NPC276430
0.7097	Intermediate Similarity	NPC227582
0.7094	Intermediate Similarity	NPC471124
0.7093	Intermediate Similarity	NPC183407
0.7093	Intermediate Similarity	NPC36405
0.7093	Intermediate Similarity	NPC469928
0.7089	Intermediate Similarity	NPC473666
0.7085	Intermediate Similarity	NPC258062
0.7085	Intermediate Similarity	NPC127677
0.7083	Intermediate Similarity	NPC473312
0.7083	Intermediate Similarity	NPC17487
0.7083	Intermediate Similarity	NPC201831
0.7081	Intermediate Similarity	NPC469896
0.708	Intermediate Similarity	NPC31700

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 NPC31097 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	521
0.2-0.3	738
0.3-0.4	1674
0.4-0.5	2419
0.5-0.6	2465
0.6-0.7	1032
0.7-0.8	81
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7757	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD8094	Discontinued
0.7674	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD8093	Discontinued
0.7656	Intermediate Similarity	NPD7619	Phase 3
0.7656	Intermediate Similarity	NPD7618	Phase 3
0.7619	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7603	Discontinued
0.7534	Intermediate Similarity	NPD7470	Discontinued
0.7523	Intermediate Similarity	NPD7817	Phase 1
0.7512	Intermediate Similarity	NPD8322	Phase 2
0.7429	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7781	Approved
0.7424	Intermediate Similarity	NPD7780	Approved
0.7419	Intermediate Similarity	NPD8114	Approved
0.7419	Intermediate Similarity	NPD8115	Approved
0.7409	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7666	Phase 3
0.7397	Intermediate Similarity	NPD7665	Phase 2
0.7397	Intermediate Similarity	NPD6376	Discontinued
0.7391	Intermediate Similarity	NPD7824	Approved
0.738	Intermediate Similarity	NPD6165	Phase 2
0.738	Intermediate Similarity	NPD6164	Phase 2
0.7371	Intermediate Similarity	NPD7791	Approved
0.7371	Intermediate Similarity	NPD7789	Approved
0.7371	Intermediate Similarity	NPD7952	Approved
0.7371	Intermediate Similarity	NPD7790	Approved
0.7371	Intermediate Similarity	NPD7953	Approved
0.7371	Intermediate Similarity	NPD7951	Approved
0.7371	Intermediate Similarity	NPD7950	Approved
0.7361	Intermediate Similarity	NPD7727	Phase 2
0.7361	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6999	Discontinued
0.7349	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD8289	Discontinued
0.7304	Intermediate Similarity	NPD7731	Approved
0.7304	Intermediate Similarity	NPD7730	Approved
0.7277	Intermediate Similarity	NPD7970	Approved
0.7277	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5426	Phase 3
0.7252	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7716	Approved
0.7249	Intermediate Similarity	NPD7717	Approved
0.7227	Intermediate Similarity	NPD7001	Phase 3
0.722	Intermediate Similarity	NPD5065	Approved
0.7217	Intermediate Similarity	NPD7271	Approved
0.7212	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8098	Approved
0.7163	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2509	Approved
0.7162	Intermediate Similarity	NPD2510	Approved
0.7143	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6176	Phase 1
0.7129	Intermediate Similarity	NPD5138	Approved
0.7129	Intermediate Similarity	NPD5140	Approved
0.7111	Intermediate Similarity	NPD8097	Phase 3
0.7111	Intermediate Similarity	NPD8096	Phase 3
0.7106	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5901	Discontinued
0.7104	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD8240	Discontinued
0.7095	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7944	Discontinued
0.7061	Intermediate Similarity	NPD2813	Phase 3
0.7061	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7711	Discontinued
0.7023	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5003	Discontinued
0.7014	Intermediate Similarity	NPD5596	Phase 2
0.7004	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7568	Phase 1
0.6996	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6665	Discontinued
0.6985	Remote Similarity	NPD2882	Phase 1
0.6982	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4499	Approved
0.697	Remote Similarity	NPD8349	Phase 1
0.6962	Remote Similarity	NPD4885	Approved
0.696	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD6249	Phase 2
0.6955	Remote Similarity	NPD6248	Phase 2
0.6941	Remote Similarity	NPD6664	Approved
0.6933	Remote Similarity	NPD2916	Discontinued
0.6933	Remote Similarity	NPD2442	Approved
0.6933	Remote Similarity	NPD2443	Approved
0.6933	Remote Similarity	NPD7415	Suspended
0.693	Remote Similarity	NPD4334	Discontinued
0.693	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.693	Remote Similarity	NPD3243	Approved
0.6927	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4602	Approved
0.6926	Remote Similarity	NPD7168	Phase 3
0.692	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.692	Remote Similarity	NPD7688	Phase 1
0.6919	Remote Similarity	NPD6595	Phase 3
0.6913	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6995	Phase 1
0.6909	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5017	Discontinued
0.6886	Remote Similarity	NPD3917	Approved
0.6886	Remote Similarity	NPD3918	Approved
0.6886	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7921	Approved
0.6884	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4948	Discontinued
0.688	Remote Similarity	NPD6752	Phase 1
0.688	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6753	Phase 1
0.6878	Remote Similarity	NPD7308	Discontinued
0.6875	Remote Similarity	NPD8283	Approved
0.6875	Remote Similarity	NPD8272	Phase 2
0.6875	Remote Similarity	NPD56	Approved
0.6875	Remote Similarity	NPD8282	Approved
0.6872	Remote Similarity	NPD8386	Phase 2
0.6872	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3389	Approved
0.687	Remote Similarity	NPD7543	Phase 2
0.687	Remote Similarity	NPD3393	Approved
0.687	Remote Similarity	NPD4558	Phase 2
0.687	Remote Similarity	NPD3394	Approved
0.6869	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6557	Phase 2
0.6866	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7948	Phase 1
0.6864	Remote Similarity	NPD2880	Discontinued
0.686	Remote Similarity	NPD2844	Phase 3
0.6858	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5807	Phase 2
0.6857	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD2094	Phase 2
0.6854	Remote Similarity	NPD2092	Phase 2
0.6854	Remote Similarity	NPD2095	Phase 2
0.6847	Remote Similarity	NPD4501	Approved
0.6847	Remote Similarity	NPD484	Approved
0.6847	Remote Similarity	NPD4500	Approved
0.6847	Remote Similarity	NPD4601	Approved
0.6847	Remote Similarity	NPD4600	Approved
0.6844	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3915	Approved
0.684	Remote Similarity	NPD6452	Discontinued
0.6838	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8356	Approved
0.6837	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.683	Remote Similarity	NPD5487	Phase 1
0.6827	Remote Similarity	NPD1325	Approved
0.6827	Remote Similarity	NPD1326	Approved
0.6822	Remote Similarity	NPD2091	Phase 2
0.6822	Remote Similarity	NPD2096	Phase 2
0.682	Remote Similarity	NPD1043	Phase 3
0.6816	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6158	Phase 2
0.6814	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.681	Remote Similarity	NPD482	Approved
0.681	Remote Similarity	NPD6492	Phase 2
0.6808	Remote Similarity	NPD3178	Discontinued
0.6798	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD8430	Approved
0.6793	Remote Similarity	NPD7694	Discontinued
0.679	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.679	Remote Similarity	NPD8016	Phase 3
0.6789	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5199	Approved
0.6781	Remote Similarity	NPD5198	Approved
0.678	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8364	Approved
0.677	Remote Similarity	NPD8363	Approved
0.6769	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD8256	Approved
0.6767	Remote Similarity	NPD8257	Approved
0.6765	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7767	Approved
0.6761	Remote Similarity	NPD5473	Discontinued
0.6759	Remote Similarity	NPD5809	Phase 3
0.6759	Remote Similarity	NPD3315	Phase 3
0.6758	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4315	Phase 2
0.6754	Remote Similarity	NPD2408	Discontinued
0.6743	Remote Similarity	NPD3439	Approved
0.6741	Remote Similarity	NPD5552	Discontinued
0.6739	Remote Similarity	NPD7657	Approved
0.6739	Remote Similarity	NPD7656	Approved
0.6739	Remote Similarity	NPD4852	Phase 2
0.6738	Remote Similarity	NPD7878	Phase 2
0.6737	Remote Similarity	NPD6850	Phase 2
0.6737	Remote Similarity	NPD6849	Phase 2
0.6737	Remote Similarity	NPD6829	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