NPASS Compound

Structure

NPC472465 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4680 3.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6266 1.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9975 1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9543 1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6974 1.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8564 2.5180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 1.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0032 1.5909 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3090 1.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6485 1.5398 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8074 2.8270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7953 0.6128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9575 0.5888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 12 2 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 10 21 1 0 0 0 0 11 1 1 1 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 13 12 1 6 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 14 20 1 1 0 0 0 15 22 1 0 0 0 0 16 20 1 1 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	358.695
LogP:	0.953
LogD:	2.078
LogS:	-2.541
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	5.419
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.09
MDCK Permeability:	0.00025286502204835415
Pgp-inhibitor:	0.0
Pgp-substrate:	0.161
Human Intestinal Absorption (HIA):	0.201
20% Bioavailability (F20%):	0.916
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.51
Plasma Protein Binding (PPB):	69.6615219116211%
Volume Distribution (VD):	0.788
Pgp-substrate:	24.178268432617188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.397
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.353
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	2.575
Half-life (T1/2):	0.557

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.561
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.324
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.073
Carcinogencity:	0.004
Eye Corrosion:	0.003
Eye Irritation:	0.111
Respiratory Toxicity:	0.387

Download Data

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

Natural Product: NPC472465

Natural Product ID:	NPC472465
*Common Name:**	UKLXBKNTSRRSJH-NBPNWECOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UKLXBKNTSRRSJH-NBPNWECOSA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-11-5-6-14-17(11)18-13(9-16(23)20(14,18)4)12(2)15(22)7-8-19(3,24)10-21/h7-8,11,13-18,21-24H,2,5-6,9-10H2,1,3-4H3/b8-7+/t11-,13+,14+,15?,16-,17-,18+,19?,20+/m1/s1
SMILES:	CC1CCC2C1C3C2(C(CC3C(=C)C(C=CC(C)(CO)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3425780
PubChem CID:	22832652
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001595] Spatane and 4,10-secospatane diterpenoids

*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
NPO5780	Stoechospermum marginatum	Species	Dictyotaceae	Eukaryota	n.a.	At a depth of 510 m, Gulf of Mannar near Mandapam coast (9 16'N, 79 12'E), Tamilnadu, India	2013-May	PMID[25978960]
NPO5780	Stoechospermum marginatum	Species	Dictyotaceae	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	3
MIC	4
Others	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	17.39	ug.mL-1	PMID[515752]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	55.56	ug.mL-1	PMID[515752]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	200.0	ug.mL-1	PMID[515752]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	200.0	ug.mL-1	PMID[515752]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	12.33	mm	PMID[515752]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	12.33	mm	PMID[515752]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12.67	mm	PMID[515752]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	11.67	mm	PMID[515752]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	195.99	ug.mL-1	PMID[515752]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	200.0	ug.mL-1	PMID[515752]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	200.0	ug.mL-1	PMID[515752]

☑ 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 NPC472465 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	197
0.1-0.2	1675
0.2-0.3	8505
0.3-0.4	15779
0.4-0.5	8914
0.5-0.6	6161
0.6-0.7	1358
0.7-0.8	92
0.8-0.85	10
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC310643
0.9048	High Similarity	NPC472466
0.8941	High Similarity	NPC472468
0.8736	High Similarity	NPC472467
0.8481	Intermediate Similarity	NPC126969
0.8289	Intermediate Similarity	NPC224532
0.8193	Intermediate Similarity	NPC472471
0.8101	Intermediate Similarity	NPC14352
0.8101	Intermediate Similarity	NPC234527
0.8077	Intermediate Similarity	NPC254845
0.8049	Intermediate Similarity	NPC475980
0.8	Intermediate Similarity	NPC471659
0.8	Intermediate Similarity	NPC320548
0.8	Intermediate Similarity	NPC309178
0.8	Intermediate Similarity	NPC472473
0.7976	Intermediate Similarity	NPC471661
0.7975	Intermediate Similarity	NPC41886
0.7931	Intermediate Similarity	NPC293287
0.7931	Intermediate Similarity	NPC152808
0.7922	Intermediate Similarity	NPC477791
0.7901	Intermediate Similarity	NPC313185
0.7895	Intermediate Similarity	NPC238352
0.7895	Intermediate Similarity	NPC477009
0.7848	Intermediate Similarity	NPC471781
0.7826	Intermediate Similarity	NPC472469
0.7805	Intermediate Similarity	NPC471658
0.7791	Intermediate Similarity	NPC471340
0.7791	Intermediate Similarity	NPC474634
0.7765	Intermediate Similarity	NPC320525
0.7763	Intermediate Similarity	NPC309300
0.7753	Intermediate Similarity	NPC474668
0.775	Intermediate Similarity	NPC471662
0.775	Intermediate Similarity	NPC471660
0.7727	Intermediate Similarity	NPC261266
0.7692	Intermediate Similarity	NPC136813
0.7692	Intermediate Similarity	NPC97404
0.7692	Intermediate Similarity	NPC73603
0.7692	Intermediate Similarity	NPC41554
0.7683	Intermediate Similarity	NPC23231
0.7683	Intermediate Similarity	NPC60818
0.7674	Intermediate Similarity	NPC50964
0.7662	Intermediate Similarity	NPC19569
0.7647	Intermediate Similarity	NPC472470
0.7647	Intermediate Similarity	NPC324772
0.7632	Intermediate Similarity	NPC474480
0.7595	Intermediate Similarity	NPC167527
0.759	Intermediate Similarity	NPC472472
0.759	Intermediate Similarity	NPC315261
0.7582	Intermediate Similarity	NPC329596
0.7582	Intermediate Similarity	NPC80561
0.7582	Intermediate Similarity	NPC204188
0.7582	Intermediate Similarity	NPC3345
0.7582	Intermediate Similarity	NPC291484
0.7582	Intermediate Similarity	NPC11216
0.7564	Intermediate Similarity	NPC162309
0.7564	Intermediate Similarity	NPC267027
0.7558	Intermediate Similarity	NPC209620
0.7558	Intermediate Similarity	NPC264245
0.7558	Intermediate Similarity	NPC23852
0.7556	Intermediate Similarity	NPC133588
0.7529	Intermediate Similarity	NPC476701
0.7528	Intermediate Similarity	NPC139724
0.7528	Intermediate Similarity	NPC477668
0.7528	Intermediate Similarity	NPC6391
0.7527	Intermediate Similarity	NPC473258
0.75	Intermediate Similarity	NPC476703
0.75	Intermediate Similarity	NPC15152
0.75	Intermediate Similarity	NPC242016
0.75	Intermediate Similarity	NPC185568
0.75	Intermediate Similarity	NPC205845
0.7473	Intermediate Similarity	NPC299527
0.7473	Intermediate Similarity	NPC470361
0.7471	Intermediate Similarity	NPC49964
0.7471	Intermediate Similarity	NPC470614
0.7471	Intermediate Similarity	NPC1272
0.7468	Intermediate Similarity	NPC163290
0.7442	Intermediate Similarity	NPC209944
0.7442	Intermediate Similarity	NPC241290
0.7442	Intermediate Similarity	NPC234193
0.7442	Intermediate Similarity	NPC164840
0.7442	Intermediate Similarity	NPC26117
0.7439	Intermediate Similarity	NPC329763
0.7419	Intermediate Similarity	NPC310013
0.7416	Intermediate Similarity	NPC318390
0.7407	Intermediate Similarity	NPC470041
0.7407	Intermediate Similarity	NPC133873
0.7391	Intermediate Similarity	NPC295668
0.7391	Intermediate Similarity	NPC475751
0.7391	Intermediate Similarity	NPC473956
0.7386	Intermediate Similarity	NPC260852
0.7386	Intermediate Similarity	NPC477667
0.7386	Intermediate Similarity	NPC317458
0.7386	Intermediate Similarity	NPC185605
0.7368	Intermediate Similarity	NPC323153
0.7368	Intermediate Similarity	NPC252809
0.7368	Intermediate Similarity	NPC288970
0.7363	Intermediate Similarity	NPC475664
0.7363	Intermediate Similarity	NPC280556
0.7356	Intermediate Similarity	NPC47761
0.7349	Intermediate Similarity	NPC329090
0.7349	Intermediate Similarity	NPC27395
0.7342	Intermediate Similarity	NPC311736
0.7326	Intermediate Similarity	NPC84694
0.7326	Intermediate Similarity	NPC47982
0.7326	Intermediate Similarity	NPC109546
0.7326	Intermediate Similarity	NPC81306
0.7326	Intermediate Similarity	NPC143182
0.7326	Intermediate Similarity	NPC328714
0.7326	Intermediate Similarity	NPC28862
0.7312	Intermediate Similarity	NPC275671
0.7303	Intermediate Similarity	NPC475798
0.7303	Intermediate Similarity	NPC124172
0.7303	Intermediate Similarity	NPC127606
0.7303	Intermediate Similarity	NPC238485
0.7292	Intermediate Similarity	NPC477226
0.7284	Intermediate Similarity	NPC304690
0.7284	Intermediate Similarity	NPC16964
0.7284	Intermediate Similarity	NPC90115
0.7284	Intermediate Similarity	NPC217570
0.7284	Intermediate Similarity	NPC74722
0.7284	Intermediate Similarity	NPC144647
0.7283	Intermediate Similarity	NPC109744
0.7283	Intermediate Similarity	NPC477215
0.7283	Intermediate Similarity	NPC476388
0.7283	Intermediate Similarity	NPC105495
0.7273	Intermediate Similarity	NPC87489
0.7273	Intermediate Similarity	NPC296701
0.7273	Intermediate Similarity	NPC101462
0.7273	Intermediate Similarity	NPC210346
0.7273	Intermediate Similarity	NPC218616
0.7273	Intermediate Similarity	NPC63111
0.7262	Intermediate Similarity	NPC328104
0.7262	Intermediate Similarity	NPC319090
0.7262	Intermediate Similarity	NPC113639
0.7253	Intermediate Similarity	NPC186145
0.7253	Intermediate Similarity	NPC149224
0.7253	Intermediate Similarity	NPC474657
0.725	Intermediate Similarity	NPC472255
0.725	Intermediate Similarity	NPC472253
0.725	Intermediate Similarity	NPC82337
0.7237	Intermediate Similarity	NPC5698
0.7237	Intermediate Similarity	NPC122239
0.7234	Intermediate Similarity	NPC98193
0.7222	Intermediate Similarity	NPC470360
0.7222	Intermediate Similarity	NPC274448
0.7215	Intermediate Similarity	NPC205618
0.7215	Intermediate Similarity	NPC469326
0.7215	Intermediate Similarity	NPC261782
0.7209	Intermediate Similarity	NPC83351
0.7209	Intermediate Similarity	NPC477522
0.7209	Intermediate Similarity	NPC181838
0.7209	Intermediate Similarity	NPC167891
0.7209	Intermediate Similarity	NPC87604
0.7209	Intermediate Similarity	NPC474216
0.7209	Intermediate Similarity	NPC477514
0.7209	Intermediate Similarity	NPC137345
0.7204	Intermediate Similarity	NPC107189
0.7204	Intermediate Similarity	NPC470832
0.7191	Intermediate Similarity	NPC477818
0.7191	Intermediate Similarity	NPC141941
0.7191	Intermediate Similarity	NPC193870
0.7191	Intermediate Similarity	NPC475789
0.7191	Intermediate Similarity	NPC470384
0.7191	Intermediate Similarity	NPC110778
0.7179	Intermediate Similarity	NPC474155
0.7179	Intermediate Similarity	NPC473508
0.7179	Intermediate Similarity	NPC473759
0.7176	Intermediate Similarity	NPC247325
0.7176	Intermediate Similarity	NPC170148
0.7176	Intermediate Similarity	NPC244488
0.7174	Intermediate Similarity	NPC22376
0.7174	Intermediate Similarity	NPC67872
0.716	Intermediate Similarity	NPC305698
0.7159	Intermediate Similarity	NPC471270
0.7158	Intermediate Similarity	NPC477605
0.7158	Intermediate Similarity	NPC298919
0.7158	Intermediate Similarity	NPC127718
0.7158	Intermediate Similarity	NPC65402
0.7143	Intermediate Similarity	NPC6605
0.7143	Intermediate Similarity	NPC471081
0.7143	Intermediate Similarity	NPC201273
0.7143	Intermediate Similarity	NPC306727
0.7143	Intermediate Similarity	NPC94462
0.7143	Intermediate Similarity	NPC299068
0.7143	Intermediate Similarity	NPC24277
0.7143	Intermediate Similarity	NPC162109
0.7143	Intermediate Similarity	NPC145245
0.7126	Intermediate Similarity	NPC30986
0.7126	Intermediate Similarity	NPC209430
0.7125	Intermediate Similarity	NPC272125
0.7113	Intermediate Similarity	NPC261807
0.7113	Intermediate Similarity	NPC476893
0.7111	Intermediate Similarity	NPC231310
0.7111	Intermediate Similarity	NPC83702
0.7111	Intermediate Similarity	NPC116613
0.7111	Intermediate Similarity	NPC209802
0.7108	Intermediate Similarity	NPC469343
0.7097	Intermediate Similarity	NPC232747
0.7097	Intermediate Similarity	NPC257485
0.7097	Intermediate Similarity	NPC115607

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 NPC472465 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	2288
0.2-0.3	4260
0.3-0.4	1815
0.4-0.5	332
0.5-0.6	218
0.6-0.7	60
0.7-0.8	4
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
0.7647	Intermediate Similarity	NPD6931	Approved
0.7647	Intermediate Similarity	NPD6930	Phase 2
0.7647	Intermediate Similarity	NPD7514	Phase 3
0.764	Intermediate Similarity	NPD7524	Approved
0.759	Intermediate Similarity	NPD6933	Approved
0.7586	Intermediate Similarity	NPD6695	Phase 3
0.7586	Intermediate Similarity	NPD5332	Approved
0.7586	Intermediate Similarity	NPD5331	Approved
0.7558	Intermediate Similarity	NPD4790	Discontinued
0.7529	Intermediate Similarity	NPD6929	Approved
0.75	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7332	Phase 2
0.7412	Intermediate Similarity	NPD7145	Approved
0.7386	Intermediate Similarity	NPD5362	Discontinued
0.7356	Intermediate Similarity	NPD6902	Approved
0.7349	Intermediate Similarity	NPD6926	Approved
0.7349	Intermediate Similarity	NPD6924	Approved
0.7294	Intermediate Similarity	NPD6932	Approved
0.7294	Intermediate Similarity	NPD5776	Phase 2
0.7294	Intermediate Similarity	NPD6925	Approved
0.7253	Intermediate Similarity	NPD7750	Discontinued
0.7241	Intermediate Similarity	NPD4821	Approved
0.7241	Intermediate Similarity	NPD4820	Approved
0.7241	Intermediate Similarity	NPD4822	Approved
0.7241	Intermediate Similarity	NPD4819	Approved
0.7222	Intermediate Similarity	NPD6893	Approved
0.7209	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4268	Approved
0.7011	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4271	Approved
0.6988	Remote Similarity	NPD7144	Approved
0.6988	Remote Similarity	NPD7143	Approved
0.6977	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6898	Phase 1
0.6947	Remote Similarity	NPD7087	Discontinued
0.6941	Remote Similarity	NPD4785	Approved
0.6941	Remote Similarity	NPD4784	Approved
0.6932	Remote Similarity	NPD6683	Phase 2
0.6905	Remote Similarity	NPD7152	Approved
0.6905	Remote Similarity	NPD7150	Approved
0.6905	Remote Similarity	NPD7151	Approved
0.6889	Remote Similarity	NPD4270	Approved
0.6889	Remote Similarity	NPD4269	Approved
0.6882	Remote Similarity	NPD4251	Approved
0.6882	Remote Similarity	NPD4250	Approved
0.6867	Remote Similarity	NPD6922	Approved
0.6867	Remote Similarity	NPD6923	Approved
0.686	Remote Similarity	NPD6942	Approved
0.686	Remote Similarity	NPD7339	Approved
0.6854	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7525	Registered
0.6848	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4249	Approved
0.6771	Remote Similarity	NPD7637	Suspended
0.6706	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD8264	Approved
0.6596	Remote Similarity	NPD5786	Approved
0.6593	Remote Similarity	NPD5369	Approved
0.6495	Remote Similarity	NPD7136	Phase 2
0.6484	Remote Similarity	NPD4748	Discontinued
0.6452	Remote Similarity	NPD7154	Phase 3
0.6437	Remote Similarity	NPD4732	Discontinued
0.642	Remote Similarity	NPD368	Approved
0.6389	Remote Similarity	NPD6371	Approved
0.6383	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4786	Approved
0.6374	Remote Similarity	NPD4195	Approved
0.6311	Remote Similarity	NPD7640	Approved
0.6311	Remote Similarity	NPD7639	Approved
0.6304	Remote Similarity	NPD5368	Approved
0.6292	Remote Similarity	NPD4190	Phase 3
0.6292	Remote Similarity	NPD5275	Approved
0.6224	Remote Similarity	NPD6051	Approved
0.6224	Remote Similarity	NPD4753	Phase 2
0.6214	Remote Similarity	NPD7638	Approved
0.6211	Remote Similarity	NPD3666	Approved
0.6211	Remote Similarity	NPD3665	Phase 1
0.6211	Remote Similarity	NPD3133	Approved
0.619	Remote Similarity	NPD5211	Phase 2
0.6176	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6435	Approved
0.617	Remote Similarity	NPD3667	Approved
0.6168	Remote Similarity	NPD6640	Phase 3
0.6162	Remote Similarity	NPD7838	Discovery
0.614	Remote Similarity	NPD7328	Approved
0.614	Remote Similarity	NPD7327	Approved
0.6126	Remote Similarity	NPD6053	Discontinued
0.6121	Remote Similarity	NPD8033	Approved
0.6111	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7983	Approved
0.6095	Remote Similarity	NPD5344	Discontinued
0.6091	Remote Similarity	NPD4634	Approved
0.6087	Remote Similarity	NPD7516	Approved
0.6078	Remote Similarity	NPD5210	Approved
0.6078	Remote Similarity	NPD4629	Approved
0.6076	Remote Similarity	NPD342	Phase 1
0.6075	Remote Similarity	NPD5141	Approved
0.604	Remote Similarity	NPD4202	Approved
0.604	Remote Similarity	NPD5778	Approved
0.604	Remote Similarity	NPD5779	Approved
0.6034	Remote Similarity	NPD8377	Approved
0.6034	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD4223	Phase 3
0.6	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD5285	Approved
0.5983	Remote Similarity	NPD8335	Approved
0.5983	Remote Similarity	NPD8380	Approved
0.5983	Remote Similarity	NPD7503	Approved
0.5983	Remote Similarity	NPD8378	Approved
0.5983	Remote Similarity	NPD8379	Approved
0.5983	Remote Similarity	NPD8296	Approved
0.598	Remote Similarity	NPD5282	Discontinued
0.5979	Remote Similarity	NPD5329	Approved
0.5963	Remote Similarity	NPD6412	Phase 2
0.5962	Remote Similarity	NPD6083	Phase 2
0.5962	Remote Similarity	NPD4755	Approved
0.5962	Remote Similarity	NPD6084	Phase 2
0.596	Remote Similarity	NPD4518	Approved
0.5943	Remote Similarity	NPD5223	Approved
0.5941	Remote Similarity	NPD6079	Approved
0.5938	Remote Similarity	NPD4788	Approved
0.5929	Remote Similarity	NPD4632	Approved
0.5918	Remote Similarity	NPD5279	Phase 3
0.5918	Remote Similarity	NPD5690	Phase 2
0.5913	Remote Similarity	NPD7115	Discovery
0.5909	Remote Similarity	NPD7320	Approved
0.5905	Remote Similarity	NPD4225	Approved
0.59	Remote Similarity	NPD5328	Approved
0.5888	Remote Similarity	NPD4633	Approved
0.5888	Remote Similarity	NPD5225	Approved
0.5888	Remote Similarity	NPD5224	Approved
0.5888	Remote Similarity	NPD5226	Approved
0.5882	Remote Similarity	NPD6399	Phase 3
0.5876	Remote Similarity	NPD4197	Approved
0.5851	Remote Similarity	NPD7645	Phase 2
0.5849	Remote Similarity	NPD4700	Approved
0.5842	Remote Similarity	NPD6698	Approved
0.5842	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD46	Approved
0.5833	Remote Similarity	NPD5174	Approved
0.5833	Remote Similarity	NPD5175	Approved
0.5802	Remote Similarity	NPD4219	Approved
0.58	Remote Similarity	NPD6903	Approved
0.5794	Remote Similarity	NPD4159	Approved
0.5785	Remote Similarity	NPD7507	Approved
0.5784	Remote Similarity	NPD5281	Approved
0.5784	Remote Similarity	NPD5284	Approved
0.5773	Remote Similarity	NPD6110	Phase 1
0.5769	Remote Similarity	NPD5695	Phase 3
0.5766	Remote Similarity	NPD6881	Approved
0.5766	Remote Similarity	NPD6899	Approved
0.5763	Remote Similarity	NPD7741	Discontinued
0.5763	Remote Similarity	NPD6054	Approved
0.5758	Remote Similarity	NPD4693	Phase 3
0.5758	Remote Similarity	NPD4688	Approved
0.5758	Remote Similarity	NPD4694	Approved
0.5758	Remote Similarity	NPD4689	Approved
0.5758	Remote Similarity	NPD5280	Approved
0.5758	Remote Similarity	NPD4690	Approved
0.5758	Remote Similarity	NPD5205	Approved
0.5758	Remote Similarity	NPD4138	Approved
0.5758	Remote Similarity	NPD3618	Phase 1
0.5755	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5370	Suspended
0.5741	Remote Similarity	NPD7632	Discontinued
0.573	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6675	Approved
0.5727	Remote Similarity	NPD5739	Approved
0.5727	Remote Similarity	NPD7128	Approved
0.5727	Remote Similarity	NPD6402	Approved
0.5714	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5222	Approved
0.5714	Remote Similarity	NPD5221	Approved
0.5714	Remote Similarity	NPD3668	Phase 3
0.5702	Remote Similarity	NPD8297	Approved
0.5701	Remote Similarity	NPD6648	Approved
0.5688	Remote Similarity	NPD4754	Approved
0.5678	Remote Similarity	NPD4522	Approved
0.5676	Remote Similarity	NPD5697	Approved
0.5667	Remote Similarity	NPD6370	Approved
0.5664	Remote Similarity	NPD6420	Discontinued
0.5664	Remote Similarity	NPD7102	Approved
0.5664	Remote Similarity	NPD7290	Approved
0.5664	Remote Similarity	NPD6883	Approved
0.566	Remote Similarity	NPD5173	Approved
0.5645	Remote Similarity	NPD7319	Approved
0.5644	Remote Similarity	NPD4722	Approved
0.5644	Remote Similarity	NPD4723	Approved
0.5641	Remote Similarity	NPD6009	Approved
0.5631	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD6411	Approved
0.563	Remote Similarity	NPD6319	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