NPASS Compound

Structure

NPC472471 OpenBabel07101718292D 25 27 0 0 1 0 0 0 0 0999 V2000 -1.4680 3.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7953 0.6128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4677 0.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7985 -0.6984 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 -1.7953 0.6128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 1.5909 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 -2.5385 -0.0563 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 -1.2601 2.2601 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 3.0032 1.5909 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 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 -3.4895 0.2527 0.0000 C 0 0 0 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 3.9543 1.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6974 1.2308 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 1 13 2 0 0 0 0 3 15 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 11 2 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 14 2 1 1 0 0 0 14 19 1 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 16 13 1 6 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 1 0 0 0 18 22 1 1 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 20 22 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.25
Volume:	381.86
LogP:	3.538
LogD:	3.934
LogS:	-3.994
# Rotatable Bonds:	6
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	4.978
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.449
MDCK Permeability:	5.7945035223383456e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.139
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.287
Plasma Protein Binding (PPB):	80.29045867919922%
Volume Distribution (VD):	1.041
Pgp-substrate:	18.31916046142578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.231
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.703
CYP2C9-inhibitor:	0.12
CYP2C9-substrate:	0.325
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.609
CYP3A4-substrate:	0.312

ADMET: Excretion

Clearance (CL):	4.551
Half-life (T1/2):	0.719

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.74
Drug-inuced Liver Injury (DILI):	0.795
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.347
Skin Sensitization:	0.083
Carcinogencity:	0.014
Eye Corrosion:	0.111
Eye Irritation:	0.459
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC472471

Natural Product ID:	NPC472471
*Common Name:**	ZEEQHLSDIXVRQY-AWSVRUDUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZEEQHLSDIXVRQY-AWSVRUDUSA-N
Standard InCHI:	InChI=1S/C22H34O3/c1-13(8-7-11-21(4,5)24)16-12-18(25-15(3)23)22(6)17-10-9-14(2)19(17)20(16)22/h7,11,14,16-20,24H,1,8-10,12H2,2-6H3/b11-7+/t14-,16+,17+,18-,19-,20+,22+/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]([C@@H]2[C@@]1(C)[C@H]1CC[C@H]([C@@H]21)C)C(=C)C/C=C/C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3425791
PubChem CID:	n.a.
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	5
MIC	4
Others	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
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	=	64.67	ug.mL-1	PMID[565036]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	44.58	ug.mL-1	PMID[565036]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	400.0	ug.mL-1	PMID[565036]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	16.0	mm	PMID[565036]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	15.33	mm	PMID[565036]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	15.33	mm	PMID[565036]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	13.33	mm	PMID[565036]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39.85	ug.mL-1	PMID[565036]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	47.12	ug.mL-1	PMID[565036]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	48.47	ug.mL-1	PMID[565036]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	200.0	ug.mL-1	PMID[565036]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	200.0	ug.mL-1	PMID[565036]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	200.0	ug.mL-1	PMID[565036]

☑ 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 NPC472471 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	184
0.1-0.2	1451
0.2-0.3	9499
0.3-0.4	14817
0.4-0.5	8123
0.5-0.6	6789
0.6-0.7	1723
0.7-0.8	98
0.8-0.85	5
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC472473
0.8929	High Similarity	NPC472466
0.8861	High Similarity	NPC472470
0.8831	High Similarity	NPC472472
0.8831	High Similarity	NPC310643
0.8824	High Similarity	NPC472468
0.8621	High Similarity	NPC472467
0.8533	High Similarity	NPC22301
0.8481	Intermediate Similarity	NPC476439
0.8462	Intermediate Similarity	NPC113639
0.8193	Intermediate Similarity	NPC472465
0.8125	Intermediate Similarity	NPC476317
0.8111	Intermediate Similarity	NPC472469
0.8025	Intermediate Similarity	NPC186109
0.7952	Intermediate Similarity	NPC80622
0.7931	Intermediate Similarity	NPC45957
0.7931	Intermediate Similarity	NPC471657
0.7882	Intermediate Similarity	NPC477667
0.7816	Intermediate Similarity	NPC477668
0.775	Intermediate Similarity	NPC234527
0.775	Intermediate Similarity	NPC14352
0.7692	Intermediate Similarity	NPC224532
0.7654	Intermediate Similarity	NPC309178
0.7654	Intermediate Similarity	NPC471659
0.7647	Intermediate Similarity	NPC471661
0.7625	Intermediate Similarity	NPC471660
0.7614	Intermediate Similarity	NPC137253
0.7609	Intermediate Similarity	NPC90453
0.7582	Intermediate Similarity	NPC177641
0.7564	Intermediate Similarity	NPC477791
0.7561	Intermediate Similarity	NPC313185
0.7532	Intermediate Similarity	NPC238352
0.7532	Intermediate Similarity	NPC477009
0.7531	Intermediate Similarity	NPC329763
0.75	Intermediate Similarity	NPC474694
0.75	Intermediate Similarity	NPC474005
0.75	Intermediate Similarity	NPC475860
0.75	Intermediate Similarity	NPC473659
0.75	Intermediate Similarity	NPC474480
0.747	Intermediate Similarity	NPC471658
0.7447	Intermediate Similarity	NPC322063
0.7439	Intermediate Similarity	NPC475517
0.7439	Intermediate Similarity	NPC474524
0.7419	Intermediate Similarity	NPC281775
0.7412	Intermediate Similarity	NPC242767
0.7412	Intermediate Similarity	NPC325869
0.7407	Intermediate Similarity	NPC471662
0.7403	Intermediate Similarity	NPC309300
0.7403	Intermediate Similarity	NPC287744
0.7403	Intermediate Similarity	NPC140233
0.7396	Intermediate Similarity	NPC290802
0.7386	Intermediate Similarity	NPC474693
0.7381	Intermediate Similarity	NPC40049
0.7368	Intermediate Similarity	NPC15152
0.7368	Intermediate Similarity	NPC475894
0.7368	Intermediate Similarity	NPC107243
0.7363	Intermediate Similarity	NPC232747
0.7342	Intermediate Similarity	NPC136813
0.7333	Intermediate Similarity	NPC128644
0.7317	Intermediate Similarity	NPC470237
0.7312	Intermediate Similarity	NPC37816
0.7308	Intermediate Similarity	NPC19569
0.7303	Intermediate Similarity	NPC245434
0.7294	Intermediate Similarity	NPC323249
0.7294	Intermediate Similarity	NPC27949
0.7294	Intermediate Similarity	NPC39547
0.7294	Intermediate Similarity	NPC260814
0.7284	Intermediate Similarity	NPC4299
0.7284	Intermediate Similarity	NPC254845
0.7273	Intermediate Similarity	NPC23748
0.7273	Intermediate Similarity	NPC474809
0.7273	Intermediate Similarity	NPC49208
0.7273	Intermediate Similarity	NPC30502
0.7262	Intermediate Similarity	NPC279537
0.7262	Intermediate Similarity	NPC126969
0.725	Intermediate Similarity	NPC167527
0.7241	Intermediate Similarity	NPC47031
0.7241	Intermediate Similarity	NPC316844
0.7241	Intermediate Similarity	NPC88735
0.7241	Intermediate Similarity	NPC170303
0.7237	Intermediate Similarity	NPC162109
0.7237	Intermediate Similarity	NPC323153
0.7237	Intermediate Similarity	NPC252809
0.7234	Intermediate Similarity	NPC7165
0.7215	Intermediate Similarity	NPC162309
0.7209	Intermediate Similarity	NPC44083
0.7209	Intermediate Similarity	NPC201225
0.7209	Intermediate Similarity	NPC153987
0.7209	Intermediate Similarity	NPC226226
0.7209	Intermediate Similarity	NPC55304
0.7204	Intermediate Similarity	NPC290651
0.7204	Intermediate Similarity	NPC45269
0.7195	Intermediate Similarity	NPC472254
0.7191	Intermediate Similarity	NPC306951
0.7191	Intermediate Similarity	NPC222634
0.7191	Intermediate Similarity	NPC165064
0.7188	Intermediate Similarity	NPC477949
0.7188	Intermediate Similarity	NPC57416
0.7188	Intermediate Similarity	NPC231751
0.7179	Intermediate Similarity	NPC469723
0.7174	Intermediate Similarity	NPC2983
0.7174	Intermediate Similarity	NPC310236
0.7174	Intermediate Similarity	NPC477215
0.7174	Intermediate Similarity	NPC476388
0.7174	Intermediate Similarity	NPC473647
0.7174	Intermediate Similarity	NPC155479
0.7172	Intermediate Similarity	NPC183570
0.7172	Intermediate Similarity	NPC280566
0.716	Intermediate Similarity	NPC101622
0.7159	Intermediate Similarity	NPC7414
0.7159	Intermediate Similarity	NPC256112
0.7159	Intermediate Similarity	NPC145963
0.7158	Intermediate Similarity	NPC476488
0.7158	Intermediate Similarity	NPC84383
0.7158	Intermediate Similarity	NPC476487
0.7143	Intermediate Similarity	NPC210346
0.7143	Intermediate Similarity	NPC316629
0.7143	Intermediate Similarity	NPC474832
0.7143	Intermediate Similarity	NPC25177
0.7143	Intermediate Similarity	NPC268829
0.7143	Intermediate Similarity	NPC222875
0.7143	Intermediate Similarity	NPC247701
0.7143	Intermediate Similarity	NPC295110
0.7143	Intermediate Similarity	NPC167877
0.7143	Intermediate Similarity	NPC166857
0.7128	Intermediate Similarity	NPC38232
0.7126	Intermediate Similarity	NPC233332
0.7125	Intermediate Similarity	NPC472266
0.7111	Intermediate Similarity	NPC287015
0.7111	Intermediate Similarity	NPC269638
0.7111	Intermediate Similarity	NPC146850
0.7108	Intermediate Similarity	NPC107783
0.7108	Intermediate Similarity	NPC92909
0.7105	Intermediate Similarity	NPC5698
0.71	Intermediate Similarity	NPC272632
0.7097	Intermediate Similarity	NPC37607
0.7097	Intermediate Similarity	NPC301969
0.7093	Intermediate Similarity	NPC470944
0.7083	Intermediate Similarity	NPC113433
0.7079	Intermediate Similarity	NPC471340
0.7079	Intermediate Similarity	NPC311070
0.7079	Intermediate Similarity	NPC476927
0.7073	Intermediate Similarity	NPC133873
0.7071	Intermediate Similarity	NPC118405
0.7065	Intermediate Similarity	NPC473879
0.7065	Intermediate Similarity	NPC249889
0.7065	Intermediate Similarity	NPC28227
0.7065	Intermediate Similarity	NPC193843
0.7065	Intermediate Similarity	NPC294480
0.7053	Intermediate Similarity	NPC201725
0.7053	Intermediate Similarity	NPC474922
0.7045	Intermediate Similarity	NPC325031
0.7045	Intermediate Similarity	NPC264245
0.7045	Intermediate Similarity	NPC59994
0.7045	Intermediate Similarity	NPC112868
0.7045	Intermediate Similarity	NPC78677
0.7041	Intermediate Similarity	NPC472826
0.7033	Intermediate Similarity	NPC474970
0.7033	Intermediate Similarity	NPC261253
0.7033	Intermediate Similarity	NPC474045
0.7033	Intermediate Similarity	NPC286153
0.7021	Intermediate Similarity	NPC221282
0.7021	Intermediate Similarity	NPC249034
0.7021	Intermediate Similarity	NPC234335
0.7011	Intermediate Similarity	NPC471537
0.7011	Intermediate Similarity	NPC170561
0.7011	Intermediate Similarity	NPC469690
0.7011	Intermediate Similarity	NPC100906
0.701	Intermediate Similarity	NPC469432
0.7	Intermediate Similarity	NPC102048
0.7	Intermediate Similarity	NPC196471
0.7	Intermediate Similarity	NPC37005
0.7	Intermediate Similarity	NPC10232
0.7	Intermediate Similarity	NPC100391
0.7	Intermediate Similarity	NPC16887
0.7	Intermediate Similarity	NPC189588
0.7	Intermediate Similarity	NPC53011
0.7	Intermediate Similarity	NPC154893
0.7	Intermediate Similarity	NPC187302
0.7	Intermediate Similarity	NPC471301
0.7	Intermediate Similarity	NPC160583
0.7	Intermediate Similarity	NPC474047
0.7	Intermediate Similarity	NPC97487
0.699	Remote Similarity	NPC475941
0.699	Remote Similarity	NPC474901
0.6989	Remote Similarity	NPC472240
0.6989	Remote Similarity	NPC146554
0.6989	Remote Similarity	NPC177141
0.6989	Remote Similarity	NPC262858
0.6989	Remote Similarity	NPC170775
0.6979	Remote Similarity	NPC67584
0.6979	Remote Similarity	NPC20546
0.6977	Remote Similarity	NPC283619
0.6977	Remote Similarity	NPC107668
0.6977	Remote Similarity	NPC84360
0.697	Remote Similarity	NPC477950
0.697	Remote Similarity	NPC99411
0.6966	Remote Similarity	NPC218616
0.6966	Remote Similarity	NPC296701
0.6966	Remote Similarity	NPC20262

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 NPC472471 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	2020
0.2-0.3	4372
0.3-0.4	1888
0.4-0.5	374
0.5-0.6	271
0.6-0.7	50
0.7-0.8	12
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
0.7882	Intermediate Similarity	NPD5332	Approved
0.7882	Intermediate Similarity	NPD5331	Approved
0.7882	Intermediate Similarity	NPD5362	Discontinued
0.7857	Intermediate Similarity	NPD4790	Discontinued
0.7701	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4822	Approved
0.7529	Intermediate Similarity	NPD4820	Approved
0.7529	Intermediate Similarity	NPD4821	Approved
0.7529	Intermediate Similarity	NPD4819	Approved
0.7529	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6051	Approved
0.7294	Intermediate Similarity	NPD4268	Approved
0.7294	Intermediate Similarity	NPD4271	Approved
0.7159	Intermediate Similarity	NPD4269	Approved
0.7159	Intermediate Similarity	NPD4270	Approved
0.7143	Intermediate Similarity	NPD4250	Approved
0.7143	Intermediate Similarity	NPD4251	Approved
0.7097	Intermediate Similarity	NPD5785	Approved
0.7079	Intermediate Similarity	NPD7154	Phase 3
0.7065	Intermediate Similarity	NPD6903	Approved
0.7045	Intermediate Similarity	NPD5369	Approved
0.7033	Intermediate Similarity	NPD5786	Approved
0.7033	Intermediate Similarity	NPD4249	Approved
0.7021	Intermediate Similarity	NPD7637	Suspended
0.6966	Remote Similarity	NPD6435	Approved
0.6932	Remote Similarity	NPD4252	Approved
0.6923	Remote Similarity	NPD5363	Approved
0.6889	Remote Similarity	NPD6695	Phase 3
0.6848	Remote Similarity	NPD7334	Approved
0.6848	Remote Similarity	NPD5330	Approved
0.6848	Remote Similarity	NPD6684	Approved
0.6848	Remote Similarity	NPD7146	Approved
0.6848	Remote Similarity	NPD7521	Approved
0.6848	Remote Similarity	NPD6409	Approved
0.6824	Remote Similarity	NPD6926	Approved
0.6824	Remote Similarity	NPD6924	Approved
0.6813	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6930	Phase 2
0.6742	Remote Similarity	NPD6931	Approved
0.6742	Remote Similarity	NPD7514	Phase 3
0.6742	Remote Similarity	NPD5368	Approved
0.6705	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7640	Approved
0.67	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6633	Remote Similarity	NPD5695	Phase 3
0.663	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4195	Approved
0.6629	Remote Similarity	NPD6929	Approved
0.6628	Remote Similarity	NPD4784	Approved
0.6628	Remote Similarity	NPD4785	Approved
0.66	Remote Similarity	NPD7638	Approved
0.6598	Remote Similarity	NPD6399	Phase 3
0.6596	Remote Similarity	NPD7750	Discontinued
0.6596	Remote Similarity	NPD7524	Approved
0.6596	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4243	Approved
0.6571	Remote Similarity	NPD7320	Approved
0.6562	Remote Similarity	NPD5207	Approved
0.6556	Remote Similarity	NPD7332	Phase 2
0.6517	Remote Similarity	NPD7145	Approved
0.6484	Remote Similarity	NPD6902	Approved
0.6477	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7144	Approved
0.6471	Remote Similarity	NPD7143	Approved
0.6465	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6673	Approved
0.6458	Remote Similarity	NPD6080	Approved
0.6458	Remote Similarity	NPD6904	Approved
0.6436	Remote Similarity	NPD5696	Approved
0.6415	Remote Similarity	NPD6899	Approved
0.6415	Remote Similarity	NPD6881	Approved
0.6413	Remote Similarity	NPD5209	Approved
0.6404	Remote Similarity	NPD5776	Phase 2
0.6404	Remote Similarity	NPD6925	Approved
0.6404	Remote Similarity	NPD6932	Approved
0.64	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7151	Approved
0.6395	Remote Similarity	NPD7152	Approved
0.6395	Remote Similarity	NPD7150	Approved
0.6383	Remote Similarity	NPD6893	Approved
0.6381	Remote Similarity	NPD5739	Approved
0.6381	Remote Similarity	NPD6402	Approved
0.6381	Remote Similarity	NPD7128	Approved
0.6381	Remote Similarity	NPD6675	Approved
0.6374	Remote Similarity	NPD7525	Registered
0.6364	Remote Similarity	NPD7339	Approved
0.6364	Remote Similarity	NPD8039	Approved
0.6364	Remote Similarity	NPD6942	Approved
0.6354	Remote Similarity	NPD5208	Approved
0.6354	Remote Similarity	NPD6672	Approved
0.6354	Remote Similarity	NPD5737	Approved
0.6353	Remote Similarity	NPD6922	Approved
0.6353	Remote Similarity	NPD6923	Approved
0.6341	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6053	Discontinued
0.6327	Remote Similarity	NPD6050	Approved
0.6327	Remote Similarity	NPD5694	Approved
0.6327	Remote Similarity	NPD5284	Approved
0.6327	Remote Similarity	NPD7087	Discontinued
0.6327	Remote Similarity	NPD5281	Approved
0.6327	Remote Similarity	NPD5693	Phase 1
0.6321	Remote Similarity	NPD5697	Approved
0.6296	Remote Similarity	NPD7290	Approved
0.6296	Remote Similarity	NPD6883	Approved
0.6296	Remote Similarity	NPD6371	Approved
0.6296	Remote Similarity	NPD7102	Approved
0.6289	Remote Similarity	NPD1695	Approved
0.6277	Remote Similarity	NPD3133	Approved
0.6277	Remote Similarity	NPD4786	Approved
0.6277	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD3666	Approved
0.6277	Remote Similarity	NPD3665	Phase 1
0.6263	Remote Similarity	NPD5778	Approved
0.6263	Remote Similarity	NPD5779	Approved
0.6262	Remote Similarity	NPD6011	Approved
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6239	Remote Similarity	NPD6869	Approved
0.6237	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4223	Phase 3
0.6237	Remote Similarity	NPD4221	Approved
0.6224	Remote Similarity	NPD5692	Phase 3
0.6211	Remote Similarity	NPD1694	Approved
0.6211	Remote Similarity	NPD5329	Approved
0.6204	Remote Similarity	NPD6014	Approved
0.6204	Remote Similarity	NPD6013	Approved
0.6204	Remote Similarity	NPD6372	Approved
0.6204	Remote Similarity	NPD6373	Approved
0.6204	Remote Similarity	NPD6012	Approved
0.62	Remote Similarity	NPD6001	Approved
0.62	Remote Similarity	NPD5707	Approved
0.6196	Remote Similarity	NPD7509	Discontinued
0.6195	Remote Similarity	NPD7328	Approved
0.6195	Remote Similarity	NPD7327	Approved
0.6182	Remote Similarity	NPD8297	Approved
0.6182	Remote Similarity	NPD6882	Approved
0.618	Remote Similarity	NPD4190	Phase 3
0.618	Remote Similarity	NPD8264	Approved
0.618	Remote Similarity	NPD5275	Approved
0.6168	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5701	Approved
0.6162	Remote Similarity	NPD6411	Approved
0.6146	Remote Similarity	NPD5690	Phase 2
0.614	Remote Similarity	NPD7516	Approved
0.6139	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6898	Phase 1
0.6122	Remote Similarity	NPD4753	Phase 2
0.6122	Remote Similarity	NPD5370	Suspended
0.6117	Remote Similarity	NPD4225	Approved
0.6106	Remote Similarity	NPD7115	Discovery
0.6105	Remote Similarity	NPD4197	Approved
0.61	Remote Similarity	NPD4202	Approved
0.6098	Remote Similarity	NPD4191	Approved
0.6098	Remote Similarity	NPD368	Approved
0.6098	Remote Similarity	NPD4192	Approved
0.6098	Remote Similarity	NPD4194	Approved
0.6098	Remote Similarity	NPD4193	Approved
0.6095	Remote Similarity	NPD5211	Phase 2
0.6095	Remote Similarity	NPD7632	Discontinued
0.6091	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8294	Approved
0.6087	Remote Similarity	NPD8377	Approved
0.6087	Remote Similarity	NPD6683	Phase 2
0.6075	Remote Similarity	NPD6008	Approved
0.6064	Remote Similarity	NPD3667	Approved
0.6061	Remote Similarity	NPD7838	Discovery
0.6058	Remote Similarity	NPD6648	Approved
0.6042	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD8378	Approved
0.6034	Remote Similarity	NPD8033	Approved
0.6034	Remote Similarity	NPD7503	Approved
0.6034	Remote Similarity	NPD8296	Approved
0.6034	Remote Similarity	NPD8380	Approved
0.6034	Remote Similarity	NPD8335	Approved
0.6034	Remote Similarity	NPD8379	Approved
0.6022	Remote Similarity	NPD4748	Discontinued
0.602	Remote Similarity	NPD4518	Approved
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5344	Discontinued
0.6	Remote Similarity	NPD6420	Discontinued
0.6	Remote Similarity	NPD7983	Approved
0.6	Remote Similarity	NPD4788	Approved
0.6	Remote Similarity	NPD8035	Phase 2
0.6	Remote Similarity	NPD8034	Phase 2
0.5981	Remote Similarity	NPD5141	Approved
0.598	Remote Similarity	NPD4629	Approved
0.598	Remote Similarity	NPD5210	Approved
0.5979	Remote Similarity	NPD4694	Approved
0.5979	Remote Similarity	NPD5279	Phase 3

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