NPASS Compound

Structure

NPC38237 OpenBabel07101718312D 28 31 0 0 1 0 0 0 0 0999 V2000 -4.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2814 2.2669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6487 3.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0451 -0.0320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5687 2.5251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0566 1.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4996 2.8904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1142 0.3333 0.0000 C 0 0 1 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 3.4197 1.5362 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 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 2.6831 1.3090 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 0.9511 1.3090 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 0.0000 1.6180 0.0000 N 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 7 1 0 0 0 0 2 15 1 0 0 0 0 3 15 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 13 15 2 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 16 4 1 6 0 0 0 16 22 1 0 0 0 0 17 5 1 6 0 0 0 17 20 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 13 1 6 0 0 0 19 23 1 0 0 0 0 20 12 1 1 0 0 0 20 24 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 24 2 0 0 0 0 22 26 1 0 0 0 0 23 24 1 0 0 0 0 25 26 2 0 0 0 0 25 27 1 0 0 0 0 26 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	379.29
Volume:	430.631
LogP:	8.574
LogD:	6.041
LogS:	-7.016
# Rotatable Bonds:	5
TPSA:	26.03
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	4.393
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.827
MDCK Permeability:	1.1843163520097733e-05
Pgp-inhibitor:	0.954
Pgp-substrate:	0.189
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.497
Plasma Protein Binding (PPB):	96.47471618652344%
Volume Distribution (VD):	6.493
Pgp-substrate:	3.376147508621216%

ADMET: Metabolism

CYP1A2-inhibitor:	0.278
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.686
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.918
CYP2C9-substrate:	0.743
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.473
CYP3A4-substrate:	0.797

ADMET: Excretion

Clearance (CL):	5.318
Half-life (T1/2):	0.021

ADMET: Toxicity

hERG Blockers:	0.185
Human Hepatotoxicity (H-HT):	0.98
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.531
Rat Oral Acute Toxicity:	0.883
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.785
Carcinogencity:	0.402
Eye Corrosion:	0.004
Eye Irritation:	0.036
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC38237

Natural Product ID:	NPC38237
*Common Name:**	Homopseudopteroxazole
IUPAC Name:	(1S,3aR,4S,6S)-1,4,7-trimethyl-6-(2-methylprop-1-enyl)-9-pentyl-2,3,3a,4,5,6-hexahydro-1H-phenaleno[2,1-d][1,3]oxazole
Synonyms:	Homopseudopteroxazole
Standard InCHIKey:	OZVSXKKOLMOAHF-RAUXBKROSA-N
Standard InCHI:	InChI=1S/C26H37NO/c1-7-8-9-10-21-27-25-18(6)23-19(13-15(2)3)14-17(5)20-12-11-16(4)22(24(20)23)26(25)28-21/h13,16-17,19-20H,7-12,14H2,1-6H3/t16-,17-,19+,20+/m0/s1
SMILES:	CCCCCc1nc2c(o1)c1[C@@H](C)CC[C@H]3c1c(c2C)[C@H](C=C(C)C)C[C@@H]3C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511256
PubChem CID:	3003592
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	West Indian sea	n.a.	PMID[10425124]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10822593]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	West Indian sea	n.a.	PMID[11170678]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828474]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	Colombian	n.a.	PMID[15497938]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17715964]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21978379]

☑ 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	2
MIC	3
Others	1

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	=	80.0	%	PMID[521524]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.5	ug.mL-1	PMID[521524]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	64.0	ug.mL-1	PMID[521525]
NPT4585	Organism	Mycobacterium diernhoferi	Mycobacterium diernhoferi	MIC	>	64.0	ug.mL-1	PMID[521525]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IC50	>	128.0	ug.mL-1	PMID[521525]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	128.0	ug.mL-1	PMID[521525]

☑ 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 NPC38237 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	702
0.1-0.2	2920
0.2-0.3	12531
0.3-0.4	5619
0.4-0.5	16305
0.5-0.6	3910
0.6-0.7	637
0.7-0.8	65
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9235	High Similarity	NPC324361
0.8894	High Similarity	NPC474428
0.7965	Intermediate Similarity	NPC185197
0.7897	Intermediate Similarity	NPC230683
0.7731	Intermediate Similarity	NPC225279
0.7719	Intermediate Similarity	NPC72715
0.7661	Intermediate Similarity	NPC144452
0.7578	Intermediate Similarity	NPC474688
0.7489	Intermediate Similarity	NPC274640
0.7466	Intermediate Similarity	NPC314633
0.7448	Intermediate Similarity	NPC209981
0.7376	Intermediate Similarity	NPC280799
0.7361	Intermediate Similarity	NPC187501
0.7359	Intermediate Similarity	NPC72905
0.7357	Intermediate Similarity	NPC329631
0.7328	Intermediate Similarity	NPC142385
0.7327	Intermediate Similarity	NPC473180
0.7324	Intermediate Similarity	NPC470930
0.7321	Intermediate Similarity	NPC470018
0.7316	Intermediate Similarity	NPC475844
0.7313	Intermediate Similarity	NPC49547
0.7294	Intermediate Similarity	NPC39500
0.7289	Intermediate Similarity	NPC74575
0.7288	Intermediate Similarity	NPC137353
0.7285	Intermediate Similarity	NPC208084
0.7284	Intermediate Similarity	NPC470042
0.7269	Intermediate Similarity	NPC473181
0.724	Intermediate Similarity	NPC131885
0.7235	Intermediate Similarity	NPC199667
0.7232	Intermediate Similarity	NPC51388
0.7207	Intermediate Similarity	NPC288987
0.7177	Intermediate Similarity	NPC475190
0.7162	Intermediate Similarity	NPC184408
0.7136	Intermediate Similarity	NPC11017
0.7119	Intermediate Similarity	NPC282346
0.7118	Intermediate Similarity	NPC474701
0.7117	Intermediate Similarity	NPC293151
0.711	Intermediate Similarity	NPC209769
0.7103	Intermediate Similarity	NPC267423
0.7087	Intermediate Similarity	NPC102593
0.7087	Intermediate Similarity	NPC473186
0.7087	Intermediate Similarity	NPC196718
0.7078	Intermediate Similarity	NPC470020
0.7069	Intermediate Similarity	NPC470017
0.7067	Intermediate Similarity	NPC198503
0.7067	Intermediate Similarity	NPC242928
0.7064	Intermediate Similarity	NPC470280
0.7048	Intermediate Similarity	NPC179287
0.7039	Intermediate Similarity	NPC470022
0.7039	Intermediate Similarity	NPC6786
0.7035	Intermediate Similarity	NPC210434
0.7035	Intermediate Similarity	NPC216612
0.7026	Intermediate Similarity	NPC39370
0.7024	Intermediate Similarity	NPC474798
0.7018	Intermediate Similarity	NPC202503
0.7014	Intermediate Similarity	NPC230403
0.7004	Intermediate Similarity	NPC205372
0.7004	Intermediate Similarity	NPC94842
0.7004	Intermediate Similarity	NPC208522
0.6987	Remote Similarity	NPC140296
0.6987	Remote Similarity	NPC270515
0.6982	Remote Similarity	NPC232225
0.6968	Remote Similarity	NPC220337
0.6955	Remote Similarity	NPC201697
0.6946	Remote Similarity	NPC161801
0.6942	Remote Similarity	NPC472588
0.6926	Remote Similarity	NPC278525
0.6926	Remote Similarity	NPC24019
0.6912	Remote Similarity	NPC286195
0.691	Remote Similarity	NPC22481
0.6909	Remote Similarity	NPC470931
0.6901	Remote Similarity	NPC43787
0.6901	Remote Similarity	NPC205934
0.6895	Remote Similarity	NPC300156
0.6895	Remote Similarity	NPC45190
0.6892	Remote Similarity	NPC146418
0.6885	Remote Similarity	NPC472589
0.688	Remote Similarity	NPC34770
0.6875	Remote Similarity	NPC118228
0.6872	Remote Similarity	NPC244543
0.6869	Remote Similarity	NPC70259
0.6864	Remote Similarity	NPC249583
0.6864	Remote Similarity	NPC4687
0.6861	Remote Similarity	NPC48353
0.6861	Remote Similarity	NPC310211
0.6861	Remote Similarity	NPC308137
0.686	Remote Similarity	NPC473188
0.686	Remote Similarity	NPC67401
0.6858	Remote Similarity	NPC46561
0.6856	Remote Similarity	NPC322482
0.6851	Remote Similarity	NPC108342
0.685	Remote Similarity	NPC118511
0.6849	Remote Similarity	NPC166712
0.6828	Remote Similarity	NPC473179
0.6824	Remote Similarity	NPC475253
0.6822	Remote Similarity	NPC182907
0.6822	Remote Similarity	NPC189903
0.6822	Remote Similarity	NPC477587
0.6822	Remote Similarity	NPC477589
0.6818	Remote Similarity	NPC203373
0.6814	Remote Similarity	NPC169402
0.6806	Remote Similarity	NPC72211
0.6804	Remote Similarity	NPC162484
0.68	Remote Similarity	NPC116238
0.68	Remote Similarity	NPC16066
0.6798	Remote Similarity	NPC323969
0.6798	Remote Similarity	NPC150239
0.6797	Remote Similarity	NPC200888
0.6795	Remote Similarity	NPC233334
0.6793	Remote Similarity	NPC166722
0.6793	Remote Similarity	NPC131486
0.6789	Remote Similarity	NPC476044
0.6774	Remote Similarity	NPC128823
0.6771	Remote Similarity	NPC269367
0.6766	Remote Similarity	NPC473182
0.6765	Remote Similarity	NPC477588
0.6765	Remote Similarity	NPC477590
0.6765	Remote Similarity	NPC477585
0.6765	Remote Similarity	NPC477586
0.6763	Remote Similarity	NPC58209
0.6751	Remote Similarity	NPC472061
0.6742	Remote Similarity	NPC304183
0.6741	Remote Similarity	NPC87413
0.6741	Remote Similarity	NPC9894
0.674	Remote Similarity	NPC314552
0.6738	Remote Similarity	NPC194740
0.6737	Remote Similarity	NPC90875
0.6721	Remote Similarity	NPC133609
0.672	Remote Similarity	NPC132385
0.6719	Remote Similarity	NPC101312
0.6713	Remote Similarity	NPC470023
0.6712	Remote Similarity	NPC193777
0.6712	Remote Similarity	NPC321428
0.6712	Remote Similarity	NPC283117
0.6711	Remote Similarity	NPC247803
0.6711	Remote Similarity	NPC94157
0.6695	Remote Similarity	NPC257851
0.6695	Remote Similarity	NPC41501
0.6682	Remote Similarity	NPC475085
0.6682	Remote Similarity	NPC295898
0.6682	Remote Similarity	NPC470021
0.6682	Remote Similarity	NPC475112
0.6682	Remote Similarity	NPC291535
0.6681	Remote Similarity	NPC473449
0.6681	Remote Similarity	NPC236668
0.6681	Remote Similarity	NPC298436
0.668	Remote Similarity	NPC160100
0.668	Remote Similarity	NPC208364
0.6667	Remote Similarity	NPC210296
0.6653	Remote Similarity	NPC124313
0.6652	Remote Similarity	NPC174760
0.6652	Remote Similarity	NPC469439
0.6652	Remote Similarity	NPC146976
0.6639	Remote Similarity	NPC84164
0.6639	Remote Similarity	NPC207283
0.6638	Remote Similarity	NPC174576
0.6637	Remote Similarity	NPC308943
0.6637	Remote Similarity	NPC222561
0.6636	Remote Similarity	NPC470586
0.6626	Remote Similarity	NPC189079
0.6624	Remote Similarity	NPC478078
0.6624	Remote Similarity	NPC473185
0.6622	Remote Similarity	NPC471304
0.6613	Remote Similarity	NPC478083
0.6613	Remote Similarity	NPC318068
0.6607	Remote Similarity	NPC207873
0.6607	Remote Similarity	NPC90185
0.6607	Remote Similarity	NPC100573
0.6603	Remote Similarity	NPC472168
0.6601	Remote Similarity	NPC227824
0.6598	Remote Similarity	NPC148889
0.6597	Remote Similarity	NPC253675
0.6595	Remote Similarity	NPC251071
0.6593	Remote Similarity	NPC294375
0.6592	Remote Similarity	NPC476106
0.659	Remote Similarity	NPC131017
0.6579	Remote Similarity	NPC55470
0.6574	Remote Similarity	NPC141915
0.6574	Remote Similarity	NPC280964
0.6574	Remote Similarity	NPC114335
0.6571	Remote Similarity	NPC173250
0.6569	Remote Similarity	NPC473187
0.6568	Remote Similarity	NPC209174
0.656	Remote Similarity	NPC129897
0.6558	Remote Similarity	NPC144381
0.6552	Remote Similarity	NPC196449
0.6552	Remote Similarity	NPC314222
0.6546	Remote Similarity	NPC120513
0.6543	Remote Similarity	NPC15406
0.6542	Remote Similarity	NPC206186
0.654	Remote Similarity	NPC472163
0.654	Remote Similarity	NPC477531
0.6538	Remote Similarity	NPC245756
0.6538	Remote Similarity	NPC97746
0.6538	Remote Similarity	NPC312872
0.6533	Remote Similarity	NPC39679
0.653	Remote Similarity	NPC243834
0.653	Remote Similarity	NPC70956
0.6525	Remote Similarity	NPC252251
0.6522	Remote Similarity	NPC223189

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 NPC38237 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	445
0.1-0.2	630
0.2-0.3	1109
0.3-0.4	1886
0.4-0.5	3140
0.5-0.6	1684
0.6-0.7	230
0.7-0.8	26
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
0.7867	Intermediate Similarity	NPD3945	Discontinued
0.7843	Intermediate Similarity	NPD2778	Approved
0.7758	Intermediate Similarity	NPD3250	Phase 1
0.7729	Intermediate Similarity	NPD2779	Approved
0.7713	Intermediate Similarity	NPD2951	Discontinued
0.7671	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1867	Approved
0.7583	Intermediate Similarity	NPD5429	Discontinued
0.7559	Intermediate Similarity	NPD2081	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6974	Phase 3
0.75	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1505	Phase 2
0.7397	Intermediate Similarity	NPD7395	Discontinued
0.7357	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD5443	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5850	Phase 3
0.733	Intermediate Similarity	NPD7180	Phase 3
0.7309	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7853	Phase 2
0.7225	Intermediate Similarity	NPD5924	Discontinued
0.7212	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5512	Phase 3
0.7156	Intermediate Similarity	NPD3392	Approved
0.7118	Intermediate Similarity	NPD1466	Phase 3
0.7118	Intermediate Similarity	NPD1467	Approved
0.7111	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3263	Phase 3
0.7009	Intermediate Similarity	NPD6568	Discontinued
0.7005	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4898	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6716	Phase 1
0.6975	Remote Similarity	NPD5817	Discontinued
0.6972	Remote Similarity	NPD3507	Phase 2
0.6959	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD5479	Discontinued
0.692	Remote Similarity	NPD7022	Phase 2
0.6909	Remote Similarity	NPD6376	Discontinued
0.6909	Remote Similarity	NPD7467	Discontinued
0.6901	Remote Similarity	NPD5857	Phase 3
0.6895	Remote Similarity	NPD6245	Phase 2
0.6892	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6790	Phase 1
0.6878	Remote Similarity	NPD7417	Discontinued
0.6875	Remote Similarity	NPD1638	Discovery
0.6866	Remote Similarity	NPD6321	Discontinued
0.684	Remote Similarity	NPD7994	Phase 2
0.6824	Remote Similarity	NPD7688	Phase 1
0.6795	Remote Similarity	NPD3746	Discontinued
0.6791	Remote Similarity	NPD6550	Discontinued
0.6786	Remote Similarity	NPD7069	Discontinued
0.6786	Remote Similarity	NPD5866	Approved
0.6784	Remote Similarity	NPD4429	Discontinued
0.6783	Remote Similarity	NPD7279	Phase 2
0.6783	Remote Similarity	NPD7278	Phase 2
0.6766	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3925	Approved
0.6751	Remote Similarity	NPD4368	Phase 2
0.675	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD3809	Discontinued
0.674	Remote Similarity	NPD5164	Discontinued
0.6728	Remote Similarity	NPD772	Phase 3
0.6726	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5293	Phase 2
0.6714	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5022	Discontinued
0.6695	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4418	Discontinued
0.6667	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5416	Discontinued
0.6652	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD3257	Approved
0.664	Remote Similarity	NPD7924	Phase 2
0.664	Remote Similarity	NPD7925	Phase 2
0.6638	Remote Similarity	NPD5632	Approved
0.6637	Remote Similarity	NPD7452	Approved
0.6637	Remote Similarity	NPD7222	Phase 2
0.6637	Remote Similarity	NPD7453	Approved
0.6625	Remote Similarity	NPD8016	Phase 3
0.6625	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3258	Approved
0.6607	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD6995	Phase 1
0.659	Remote Similarity	NPD6590	Discontinued
0.6584	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD4952	Phase 3
0.6557	Remote Similarity	NPD5488	Discontinued
0.6556	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD3259	Approved
0.6552	Remote Similarity	NPD4923	Phase 1
0.6547	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.654	Remote Similarity	NPD6962	Phase 2
0.6537	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.653	Remote Similarity	NPD6988	Phase 1
0.6522	Remote Similarity	NPD6719	Approved
0.651	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6242	Discontinued
0.6505	Remote Similarity	NPD6457	Approved
0.65	Remote Similarity	NPD3006	Discontinued
0.6498	Remote Similarity	NPD9243	Approved
0.6498	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4373	Phase 2
0.6483	Remote Similarity	NPD4328	Approved
0.6481	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD5482	Discontinued
0.6478	Remote Similarity	NPD6475	Phase 2
0.6473	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD1955	Discontinued
0.6447	Remote Similarity	NPD4502	Phase 2
0.6444	Remote Similarity	NPD7031	Phase 1
0.6438	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7872	Phase 2
0.6429	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5256	Discontinued
0.6413	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD3477	Phase 2
0.64	Remote Similarity	NPD8463	Approved
0.6396	Remote Similarity	NPD4548	Discontinued
0.6392	Remote Similarity	NPD6456	Discontinued
0.6389	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD2916	Discontinued
0.6382	Remote Similarity	NPD7206	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6037	Discontinued
0.6372	Remote Similarity	NPD4889	Approved
0.6372	Remote Similarity	NPD5601	Phase 2
0.6372	Remote Similarity	NPD7010	Phase 3
0.6372	Remote Similarity	NPD6150	Discontinued
0.6371	Remote Similarity	NPD7426	Phase 1
0.6371	Remote Similarity	NPD8102	Discontinued
0.6368	Remote Similarity	NPD3290	Approved
0.6368	Remote Similarity	NPD3289	Phase 3
0.6368	Remote Similarity	NPD3920	Phase 2
0.6367	Remote Similarity	NPD4322	Discontinued
0.6364	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD2920	Discontinued
0.6349	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5499	Approved
0.6344	Remote Similarity	NPD7043	Discontinued
0.6341	Remote Similarity	NPD7592	Phase 2
0.634	Remote Similarity	NPD7556	Discontinued
0.6338	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5532	Phase 2
0.6325	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD3763	Approved
0.6323	Remote Similarity	NPD6874	Approved
0.6323	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD8311	Discontinued
0.6307	Remote Similarity	NPD4885	Approved
0.6306	Remote Similarity	NPD6162	Approved
0.6306	Remote Similarity	NPD5515	Phase 2
0.6306	Remote Similarity	NPD6161	Approved
0.6305	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5936	Approved
0.6304	Remote Similarity	NPD5939	Approved
0.63	Remote Similarity	NPD5530	Phase 1
0.6298	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8100	Phase 3
0.6284	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD2953	Discontinued
0.6277	Remote Similarity	NPD4927	Discontinued
0.6275	Remote Similarity	NPD6531	Approved
0.6275	Remote Similarity	NPD6530	Approved
0.6273	Remote Similarity	NPD4372	Phase 1
0.6271	Remote Similarity	NPD5506	Approved
0.6271	Remote Similarity	NPD5507	Approved
0.627	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD8149	Discontinued
0.6265	Remote Similarity	NPD8358	Approved
0.6261	Remote Similarity	NPD5914	Approved
0.6256	Remote Similarity	NPD2564	Approved
0.6256	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD2565	Phase 2
0.6255	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5559	Phase 2
0.6245	Remote Similarity	NPD7391	Discontinued
0.624	Remote Similarity	NPD7658	Phase 2
0.6239	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6208	Discontinued

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