NPASS Compound

Structure

NPC472470 OpenBabel07101718292D 28 30 0 0 1 0 0 0 0 0999 V2000 -2.5385 0.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2327 0.4164 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 -1.4680 -3.2382 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 2.7953 -0.6128 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 -3.6974 -1.2308 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 -2.5388 0.0000 C 0 0 0 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 -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 -4.1132 -3.1871 0.0000 C 0 0 0 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 -2.9543 -1.9000 0.0000 C 0 0 3 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 1.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3212 -4.1653 0.0000 O 0 0 0 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 -3.1622 -2.8781 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 1 0 0 0 0 2 13 1 0 0 0 0 4 15 2 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 24 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 14 3 1 6 0 0 0 14 22 1 0 0 0 0 16 25 2 0 0 0 0 16 27 1 0 0 0 0 17 26 2 0 0 0 0 17 28 1 0 0 0 0 18 27 1 0 0 0 0 19 15 1 1 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 20 24 1 6 0 0 0 21 24 1 6 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.26
Volume:	422.606
LogP:	4.212
LogD:	4.359
LogS:	-4.175
# Rotatable Bonds:	8
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	4.991
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.616
MDCK Permeability:	6.338238745229319e-05
Pgp-inhibitor:	0.962
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.086

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	86.74393463134766%
Volume Distribution (VD):	1.772
Pgp-substrate:	9.262968063354492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.148
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.383
CYP3A4-substrate:	0.514

ADMET: Excretion

Clearance (CL):	3.238
Half-life (T1/2):	0.482

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.933
Drug-inuced Liver Injury (DILI):	0.895
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.084
Carcinogencity:	0.01
Eye Corrosion:	0.007
Eye Irritation:	0.075
Respiratory Toxicity:	0.175

Download Data

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

Natural Product: NPC472470

Natural Product ID:	NPC472470
*Common Name:**	XJSUFPRPSVYSPS-UUNGEATQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XJSUFPRPSVYSPS-UUNGEATQSA-N
Standard InCHI:	InChI=1S/C24H36O4/c1-13(2)10-18(27-16(5)25)11-15(4)19-12-21(28-17(6)26)24(7)20-9-8-14(3)22(20)23(19)24/h10,14,18-23H,4,8-9,11-12H2,1-3,5-7H3/t14-,18?,19+,20+,21-,22-,23+,24+/m1/s1
SMILES:	CC1CCC2C1C3C2(C(CC3C(=C)CC(C=C(C)C)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3425790
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	=	67.12	ug.mL-1	PMID[551914]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	77.85	ug.mL-1	PMID[551914]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	400.0	ug.mL-1	PMID[551914]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	12.33	mm	PMID[551914]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	12.33	mm	PMID[551914]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	11.33	mm	PMID[551914]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	0.0	mm	PMID[551914]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	84.91	ug.mL-1	PMID[551914]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29.04	ug.mL-1	PMID[551914]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	40.12	ug.mL-1	PMID[551914]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	400.0	ug.mL-1	PMID[551914]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	400.0	ug.mL-1	PMID[551914]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	400.0	ug.mL-1	PMID[551914]

☑ 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 NPC472470 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	212
0.1-0.2	1666
0.2-0.3	9340
0.3-0.4	15023
0.4-0.5	8418
0.5-0.6	6159
0.6-0.7	1763
0.7-0.8	107
0.8-0.85	5
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC472473
0.8861	High Similarity	NPC472471
0.8649	High Similarity	NPC22301
0.8506	High Similarity	NPC472467
0.8372	Intermediate Similarity	NPC472466
0.8276	Intermediate Similarity	NPC472468
0.8228	Intermediate Similarity	NPC472472
0.8118	Intermediate Similarity	NPC137253
0.8	Intermediate Similarity	NPC476317
0.7975	Intermediate Similarity	NPC474524
0.7975	Intermediate Similarity	NPC475517
0.7907	Intermediate Similarity	NPC286153
0.7901	Intermediate Similarity	NPC476439
0.7901	Intermediate Similarity	NPC186109
0.7875	Intermediate Similarity	NPC113639
0.7865	Intermediate Similarity	NPC221282
0.7865	Intermediate Similarity	NPC290651
0.7821	Intermediate Similarity	NPC469660
0.7816	Intermediate Similarity	NPC471657
0.7816	Intermediate Similarity	NPC45957
0.7805	Intermediate Similarity	NPC474005
0.7778	Intermediate Similarity	NPC310643
0.7727	Intermediate Similarity	NPC473879
0.7701	Intermediate Similarity	NPC477668
0.7692	Intermediate Similarity	NPC281775
0.7692	Intermediate Similarity	NPC101622
0.7662	Intermediate Similarity	NPC472266
0.7647	Intermediate Similarity	NPC472465
0.764	Intermediate Similarity	NPC177141
0.7619	Intermediate Similarity	NPC80622
0.7609	Intermediate Similarity	NPC472469
0.7595	Intermediate Similarity	NPC4299
0.7558	Intermediate Similarity	NPC477667
0.7558	Intermediate Similarity	NPC12283
0.7558	Intermediate Similarity	NPC474193
0.7558	Intermediate Similarity	NPC30502
0.7527	Intermediate Similarity	NPC113433
0.75	Intermediate Similarity	NPC469620
0.75	Intermediate Similarity	NPC469690
0.75	Intermediate Similarity	NPC474045
0.75	Intermediate Similarity	NPC153987
0.75	Intermediate Similarity	NPC477084
0.75	Intermediate Similarity	NPC325869
0.75	Intermediate Similarity	NPC261253
0.75	Intermediate Similarity	NPC44083
0.7473	Intermediate Similarity	NPC177641
0.7473	Intermediate Similarity	NPC234335
0.7471	Intermediate Similarity	NPC96055
0.7444	Intermediate Similarity	NPC473647
0.7442	Intermediate Similarity	NPC471218
0.7416	Intermediate Similarity	NPC474832
0.7412	Intermediate Similarity	NPC469802
0.7412	Intermediate Similarity	NPC233332
0.7407	Intermediate Similarity	NPC222244
0.7407	Intermediate Similarity	NPC16349
0.7381	Intermediate Similarity	NPC184737
0.7363	Intermediate Similarity	NPC273199
0.7356	Intermediate Similarity	NPC23748
0.7356	Intermediate Similarity	NPC49208
0.7349	Intermediate Similarity	NPC301525
0.7333	Intermediate Similarity	NPC470613
0.7333	Intermediate Similarity	NPC471956
0.7333	Intermediate Similarity	NPC470612
0.7326	Intermediate Similarity	NPC25554
0.7312	Intermediate Similarity	NPC90453
0.7312	Intermediate Similarity	NPC471994
0.7312	Intermediate Similarity	NPC166143
0.7312	Intermediate Similarity	NPC120351
0.7294	Intermediate Similarity	NPC242767
0.7294	Intermediate Similarity	NPC182550
0.7292	Intermediate Similarity	NPC290802
0.7284	Intermediate Similarity	NPC472254
0.7273	Intermediate Similarity	NPC140233
0.7273	Intermediate Similarity	NPC477575
0.7273	Intermediate Similarity	NPC287744
0.7273	Intermediate Similarity	NPC477576
0.7273	Intermediate Similarity	NPC238197
0.7273	Intermediate Similarity	NPC100391
0.7263	Intermediate Similarity	NPC477949
0.7263	Intermediate Similarity	NPC231751
0.7262	Intermediate Similarity	NPC53581
0.7262	Intermediate Similarity	NPC103987
0.7253	Intermediate Similarity	NPC288699
0.725	Intermediate Similarity	NPC269841
0.7241	Intermediate Similarity	NPC35556
0.7234	Intermediate Similarity	NPC476487
0.7234	Intermediate Similarity	NPC476488
0.7234	Intermediate Similarity	NPC281134
0.7234	Intermediate Similarity	NPC67584
0.7234	Intermediate Similarity	NPC33473
0.7222	Intermediate Similarity	NPC476600
0.7216	Intermediate Similarity	NPC25177
0.7216	Intermediate Similarity	NPC295110
0.7216	Intermediate Similarity	NPC298233
0.7216	Intermediate Similarity	NPC247701
0.7216	Intermediate Similarity	NPC268829
0.7216	Intermediate Similarity	NPC222875
0.7209	Intermediate Similarity	NPC474739
0.7209	Intermediate Similarity	NPC276356
0.7195	Intermediate Similarity	NPC477085
0.7195	Intermediate Similarity	NPC470237
0.7195	Intermediate Similarity	NPC234527
0.7195	Intermediate Similarity	NPC14352
0.7191	Intermediate Similarity	NPC475860
0.7191	Intermediate Similarity	NPC474694
0.7191	Intermediate Similarity	NPC474013
0.7191	Intermediate Similarity	NPC235792
0.7191	Intermediate Similarity	NPC78089
0.7191	Intermediate Similarity	NPC473659
0.7188	Intermediate Similarity	NPC471610
0.7179	Intermediate Similarity	NPC238352
0.7179	Intermediate Similarity	NPC477009
0.7174	Intermediate Similarity	NPC302280
0.7174	Intermediate Similarity	NPC37607
0.7174	Intermediate Similarity	NPC306168
0.7174	Intermediate Similarity	NPC49946
0.7174	Intermediate Similarity	NPC301969
0.7159	Intermediate Similarity	NPC170862
0.7159	Intermediate Similarity	NPC108045
0.7159	Intermediate Similarity	NPC193198
0.7159	Intermediate Similarity	NPC474809
0.7159	Intermediate Similarity	NPC222358
0.7159	Intermediate Similarity	NPC471340
0.7159	Intermediate Similarity	NPC475622
0.7158	Intermediate Similarity	NPC322063
0.7158	Intermediate Similarity	NPC213078
0.7158	Intermediate Similarity	NPC307164
0.7143	Intermediate Similarity	NPC28227
0.7126	Intermediate Similarity	NPC475944
0.7126	Intermediate Similarity	NPC471325
0.7126	Intermediate Similarity	NPC471661
0.7125	Intermediate Similarity	NPC224532
0.7111	Intermediate Similarity	NPC64153
0.7111	Intermediate Similarity	NPC107787
0.7111	Intermediate Similarity	NPC469676
0.7111	Intermediate Similarity	NPC470051
0.7111	Intermediate Similarity	NPC474970
0.7111	Intermediate Similarity	NPC470050
0.7108	Intermediate Similarity	NPC477204
0.7108	Intermediate Similarity	NPC140287
0.7108	Intermediate Similarity	NPC474758
0.71	Intermediate Similarity	NPC220217
0.71	Intermediate Similarity	NPC119855
0.7093	Intermediate Similarity	NPC55304
0.7093	Intermediate Similarity	NPC170561
0.7093	Intermediate Similarity	NPC226226
0.7083	Intermediate Similarity	NPC475894
0.7083	Intermediate Similarity	NPC161493
0.7083	Intermediate Similarity	NPC202705
0.7083	Intermediate Similarity	NPC69385
0.7079	Intermediate Similarity	NPC474693
0.7079	Intermediate Similarity	NPC53011
0.7079	Intermediate Similarity	NPC37005
0.7079	Intermediate Similarity	NPC16887
0.7079	Intermediate Similarity	NPC154893
0.7079	Intermediate Similarity	NPC475100
0.7073	Intermediate Similarity	NPC477087
0.7073	Intermediate Similarity	NPC477086
0.7071	Intermediate Similarity	NPC280566
0.7071	Intermediate Similarity	NPC10232
0.7071	Intermediate Similarity	NPC196471
0.7071	Intermediate Similarity	NPC97487
0.7071	Intermediate Similarity	NPC189588
0.7071	Intermediate Similarity	NPC160583
0.7071	Intermediate Similarity	NPC474775
0.7071	Intermediate Similarity	NPC187302
0.7071	Intermediate Similarity	NPC183570
0.7065	Intermediate Similarity	NPC477215
0.7065	Intermediate Similarity	NPC474679
0.7065	Intermediate Similarity	NPC283409
0.7065	Intermediate Similarity	NPC476388
0.7065	Intermediate Similarity	NPC293044
0.7059	Intermediate Similarity	NPC470240
0.7059	Intermediate Similarity	NPC476794
0.7059	Intermediate Similarity	NPC84360
0.7059	Intermediate Similarity	NPC189206
0.7053	Intermediate Similarity	NPC52044
0.7053	Intermediate Similarity	NPC20546
0.7053	Intermediate Similarity	NPC470978
0.7053	Intermediate Similarity	NPC470974
0.7051	Intermediate Similarity	NPC329698
0.7051	Intermediate Similarity	NPC469723
0.7041	Intermediate Similarity	NPC477950
0.7033	Intermediate Similarity	NPC167877
0.7033	Intermediate Similarity	NPC24728
0.7033	Intermediate Similarity	NPC166857
0.7027	Intermediate Similarity	NPC96663
0.7024	Intermediate Similarity	NPC313185
0.7021	Intermediate Similarity	NPC472954
0.7021	Intermediate Similarity	NPC37816
0.7021	Intermediate Similarity	NPC470187
0.7021	Intermediate Similarity	NPC473678
0.7011	Intermediate Similarity	NPC47747
0.701	Intermediate Similarity	NPC176845
0.701	Intermediate Similarity	NPC181147
0.701	Intermediate Similarity	NPC470188
0.701	Intermediate Similarity	NPC222011
0.701	Intermediate Similarity	NPC98868
0.701	Intermediate Similarity	NPC252295
0.7	Intermediate Similarity	NPC287015

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 NPC472470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	2222
0.2-0.3	4239
0.3-0.4	1835
0.4-0.5	381
0.5-0.6	229
0.6-0.7	50
0.7-0.8	6
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
0.8	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6051	Approved
0.7558	Intermediate Similarity	NPD5331	Approved
0.7558	Intermediate Similarity	NPD5332	Approved
0.7558	Intermediate Similarity	NPD5362	Discontinued
0.7529	Intermediate Similarity	NPD4790	Discontinued
0.7209	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5785	Approved
0.7143	Intermediate Similarity	NPD6903	Approved
0.7011	Intermediate Similarity	NPD4821	Approved
0.7011	Intermediate Similarity	NPD4820	Approved
0.7011	Intermediate Similarity	NPD4822	Approved
0.7011	Intermediate Similarity	NPD4819	Approved
0.6977	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4268	Approved
0.6977	Remote Similarity	NPD4271	Approved
0.6962	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5330	Approved
0.6923	Remote Similarity	NPD7521	Approved
0.6923	Remote Similarity	NPD6684	Approved
0.6923	Remote Similarity	NPD6409	Approved
0.6923	Remote Similarity	NPD7146	Approved
0.6923	Remote Similarity	NPD7334	Approved
0.6854	Remote Similarity	NPD5209	Approved
0.6854	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4269	Approved
0.6854	Remote Similarity	NPD4270	Approved
0.6848	Remote Similarity	NPD4250	Approved
0.6848	Remote Similarity	NPD4251	Approved
0.6837	Remote Similarity	NPD7638	Approved
0.6778	Remote Similarity	NPD7154	Phase 3
0.6774	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7640	Approved
0.6768	Remote Similarity	NPD7639	Approved
0.6742	Remote Similarity	NPD5369	Approved
0.6739	Remote Similarity	NPD5786	Approved
0.6739	Remote Similarity	NPD4249	Approved
0.6737	Remote Similarity	NPD7637	Suspended
0.6737	Remote Similarity	NPD5693	Phase 1
0.6702	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.663	Remote Similarity	NPD5363	Approved
0.6629	Remote Similarity	NPD4252	Approved
0.6628	Remote Similarity	NPD8039	Approved
0.6625	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6672	Approved
0.6596	Remote Similarity	NPD5737	Approved
0.6593	Remote Similarity	NPD6695	Phase 3
0.6559	Remote Similarity	NPD6098	Approved
0.6542	Remote Similarity	NPD6053	Discontinued
0.6531	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6904	Approved
0.6526	Remote Similarity	NPD6673	Approved
0.6526	Remote Similarity	NPD6080	Approved
0.6522	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6926	Approved
0.6512	Remote Similarity	NPD6924	Approved
0.6465	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1694	Approved
0.6444	Remote Similarity	NPD5368	Approved
0.64	Remote Similarity	NPD6083	Phase 2
0.64	Remote Similarity	NPD6084	Phase 2
0.6392	Remote Similarity	NPD6050	Approved
0.6381	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6933	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6364	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6371	Approved
0.6337	Remote Similarity	NPD4225	Approved
0.6333	Remote Similarity	NPD6929	Approved
0.6321	Remote Similarity	NPD7320	Approved
0.6316	Remote Similarity	NPD7750	Discontinued
0.6316	Remote Similarity	NPD7524	Approved
0.6289	Remote Similarity	NPD5692	Phase 3
0.6289	Remote Similarity	NPD5207	Approved
0.6289	Remote Similarity	NPD7838	Discovery
0.6286	Remote Similarity	NPD6008	Approved
0.6264	Remote Similarity	NPD6930	Phase 2
0.6264	Remote Similarity	NPD6931	Approved
0.625	Remote Similarity	NPD5208	Approved
0.625	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD7328	Approved
0.625	Remote Similarity	NPD7327	Approved
0.625	Remote Similarity	NPD6942	Approved
0.6235	Remote Similarity	NPD6923	Approved
0.6235	Remote Similarity	NPD6922	Approved
0.6228	Remote Similarity	NPD8033	Approved
0.6224	Remote Similarity	NPD5694	Approved
0.6195	Remote Similarity	NPD7516	Approved
0.6176	Remote Similarity	NPD5696	Approved
0.617	Remote Similarity	NPD4786	Approved
0.6163	Remote Similarity	NPD7143	Approved
0.6163	Remote Similarity	NPD7144	Approved
0.6154	Remote Similarity	NPD7632	Discontinued
0.6146	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.614	Remote Similarity	NPD8294	Approved
0.614	Remote Similarity	NPD8377	Approved
0.6136	Remote Similarity	NPD4785	Approved
0.6136	Remote Similarity	NPD4784	Approved
0.6132	Remote Similarity	NPD5739	Approved
0.6132	Remote Similarity	NPD6675	Approved
0.6132	Remote Similarity	NPD7128	Approved
0.6132	Remote Similarity	NPD6402	Approved
0.6122	Remote Similarity	NPD6698	Approved
0.6122	Remote Similarity	NPD46	Approved
0.6111	Remote Similarity	NPD5776	Phase 2
0.6111	Remote Similarity	NPD6925	Approved
0.61	Remote Similarity	NPD6001	Approved
0.6092	Remote Similarity	NPD7151	Approved
0.6092	Remote Similarity	NPD4243	Approved
0.6092	Remote Similarity	NPD7152	Approved
0.6092	Remote Similarity	NPD7150	Approved
0.6087	Remote Similarity	NPD8379	Approved
0.6087	Remote Similarity	NPD8335	Approved
0.6087	Remote Similarity	NPD7525	Registered
0.6087	Remote Similarity	NPD7514	Phase 3
0.6087	Remote Similarity	NPD8378	Approved
0.6087	Remote Similarity	NPD8380	Approved
0.6087	Remote Similarity	NPD8296	Approved
0.6061	Remote Similarity	NPD6411	Approved
0.6061	Remote Similarity	NPD7087	Discontinued
0.6044	Remote Similarity	NPD7145	Approved
0.6044	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6902	Approved
0.6019	Remote Similarity	NPD6899	Approved
0.6019	Remote Similarity	NPD6881	Approved
0.6018	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD3133	Approved
0.5978	Remote Similarity	NPD4195	Approved
0.5963	Remote Similarity	NPD6373	Approved
0.5963	Remote Similarity	NPD6372	Approved
0.5962	Remote Similarity	NPD6648	Approved
0.5957	Remote Similarity	NPD3667	Approved
0.5948	Remote Similarity	NPD7503	Approved
0.5943	Remote Similarity	NPD6052	Approved
0.5941	Remote Similarity	NPD5707	Approved
0.5938	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6893	Approved
0.5934	Remote Similarity	NPD6932	Approved
0.5926	Remote Similarity	NPD5697	Approved
0.5926	Remote Similarity	NPD5701	Approved
0.5921	Remote Similarity	NPD6927	Phase 3
0.5914	Remote Similarity	NPD7332	Phase 2
0.5914	Remote Similarity	NPD7509	Discontinued
0.5909	Remote Similarity	NPD6883	Approved
0.5909	Remote Similarity	NPD7102	Approved
0.5909	Remote Similarity	NPD7290	Approved
0.5905	Remote Similarity	NPD5344	Discontinued
0.59	Remote Similarity	NPD5281	Approved
0.59	Remote Similarity	NPD8034	Phase 2
0.59	Remote Similarity	NPD8035	Phase 2
0.59	Remote Similarity	NPD5284	Approved
0.5882	Remote Similarity	NPD5654	Approved
0.5882	Remote Similarity	NPD7507	Approved
0.5872	Remote Similarity	NPD6686	Approved
0.5872	Remote Similarity	NPD6011	Approved
0.5859	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6101	Approved
0.5859	Remote Similarity	NPD4753	Phase 2
0.5859	Remote Similarity	NPD5370	Suspended
0.5856	Remote Similarity	NPD6649	Approved
0.5856	Remote Similarity	NPD6869	Approved
0.5856	Remote Similarity	NPD8130	Phase 1
0.5856	Remote Similarity	NPD6650	Approved
0.5856	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6617	Approved
0.5856	Remote Similarity	NPD6847	Approved
0.5818	Remote Similarity	NPD6013	Approved
0.5818	Remote Similarity	NPD6012	Approved
0.5818	Remote Similarity	NPD6014	Approved
0.5806	Remote Similarity	NPD6683	Phase 2
0.5804	Remote Similarity	NPD6882	Approved
0.5804	Remote Similarity	NPD8297	Approved
0.5789	Remote Similarity	NPD4221	Approved
0.5789	Remote Similarity	NPD4223	Phase 3
0.5784	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD7748	Approved
0.5784	Remote Similarity	NPD7900	Approved
0.5773	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5329	Approved
0.5769	Remote Similarity	NPD5959	Approved
0.5766	Remote Similarity	NPD6420	Discontinued
0.5745	Remote Similarity	NPD4748	Discontinued
0.5743	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD7983	Approved
0.5738	Remote Similarity	NPD7319	Approved
0.573	Remote Similarity	NPD5777	Approved
0.5714	Remote Similarity	NPD5275	Approved
0.5714	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8264	Approved
0.5714	Remote Similarity	NPD4190	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