NPASS Compound

Structure

CID291078 OpenBabel06191716102D 23 24 0 0 0 0 0 0 0 0999 V2000 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 7 1 0 0 0 0 4 5 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 17 2 0 0 0 0 8 12 1 0 0 0 0 8 13 2 0 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 19 2 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.09
Volume:	311.256
LogP:	2.558
LogD:	0.901
LogS:	-2.65
# Rotatable Bonds:	4
TPSA:	138.45
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	3.146
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.525
MDCK Permeability:	8.010248166101519e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.856
20% Bioavailability (F20%):	0.881
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	97.4842758178711%
Volume Distribution (VD):	0.487
Pgp-substrate:	6.3843183517456055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.555
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.415
CYP2C9-substrate:	0.294
CYP2D6-inhibitor:	0.083
CYP2D6-substrate:	0.189
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.032

ADMET: Excretion

Clearance (CL):	9.97
Half-life (T1/2):	0.945

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.633
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.728
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.458
Skin Sensitization:	0.969
Carcinogencity:	0.345
Eye Corrosion:	0.004
Eye Irritation:	0.907
Respiratory Toxicity:	0.177

Download Data

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

Natural Product: NPC291078

Natural Product ID:	NPC291078
*Common Name:**	XBDMOGQOBVXWTC-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	11,12-Dihydrolindbladione
Standard InCHIKey:	XBDMOGQOBVXWTC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O7/c1-2-3-7(17)4-5-8-12(19)11-9(14(21)13(8)20)6-10(18)15(22)16(11)23/h6,18,20,22-23H,2-5H2,1H3
SMILES:	CCCC(=O)CCC1=C(O)C(=O)c2c(C1=O)c(O)c(c(c2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460436
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO9271	Lindbladia tubulina	Species	Cribrariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880324]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9271	Lindbladia tubulina	Species	Cribrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	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

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	12.1	ug.mL-1	PMID[495778]
NPT168	Cell Line	P388	Mus musculus	IC50	=	14.0	ug.mL-1	PMID[495778]
NPT168	Cell Line	P388	Mus musculus	IC50	=	12.6	ug.mL-1	PMID[495778]

☑ 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 NPC291078 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	393
0.1-0.2	1705
0.2-0.3	4698
0.3-0.4	11877
0.4-0.5	6781
0.5-0.6	5215
0.6-0.7	6225
0.7-0.8	5347
0.8-0.85	382
0.85-0.9	62
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9247	High Similarity	NPC127172
0.9184	High Similarity	NPC234485
0.9065	High Similarity	NPC290030
0.9058	High Similarity	NPC129752
0.9058	High Similarity	NPC14377
0.9007	High Similarity	NPC203063
0.8936	High Similarity	NPC472903
0.8912	High Similarity	NPC48949
0.8889	High Similarity	NPC324209
0.8857	High Similarity	NPC264112
0.8857	High Similarity	NPC65005
0.8857	High Similarity	NPC194764
0.8832	High Similarity	NPC117609
0.8824	High Similarity	NPC179898
0.8819	High Similarity	NPC238629
0.8811	High Similarity	NPC472904
0.8777	High Similarity	NPC4170
0.8776	High Similarity	NPC471907
0.875	High Similarity	NPC193555
0.875	High Similarity	NPC477410
0.8732	High Similarity	NPC123714
0.8716	High Similarity	NPC134293
0.8714	High Similarity	NPC282780
0.8714	High Similarity	NPC166480
0.8705	High Similarity	NPC135801
0.8671	High Similarity	NPC138099
0.8671	High Similarity	NPC242994
0.8662	High Similarity	NPC471452
0.8662	High Similarity	NPC471905
0.8658	High Similarity	NPC280295
0.8633	High Similarity	NPC34070
0.8633	High Similarity	NPC469526
0.8611	High Similarity	NPC181560
0.8611	High Similarity	NPC169452
0.8603	High Similarity	NPC477454
0.8601	High Similarity	NPC61398
0.8601	High Similarity	NPC416
0.8601	High Similarity	NPC230811
0.8592	High Similarity	NPC254847
0.8592	High Similarity	NPC223836
0.8582	High Similarity	NPC44437
0.8561	High Similarity	NPC26697
0.8561	High Similarity	NPC233056
0.8561	High Similarity	NPC244441
0.8553	High Similarity	NPC472048
0.8542	High Similarity	NPC162939
0.854	High Similarity	NPC231774
0.854	High Similarity	NPC473691
0.8531	High Similarity	NPC147418
0.8531	High Similarity	NPC53414
0.8531	High Similarity	NPC53206
0.8526	High Similarity	NPC476822
0.8521	High Similarity	NPC72918
0.8521	High Similarity	NPC290803
0.8511	High Similarity	NPC48036
0.8511	High Similarity	NPC294226
0.8503	High Similarity	NPC471906
0.8503	High Similarity	NPC244691
0.8493	Intermediate Similarity	NPC135524
0.8489	Intermediate Similarity	NPC92624
0.8487	Intermediate Similarity	NPC107109
0.8477	Intermediate Similarity	NPC35
0.8472	Intermediate Similarity	NPC175552
0.8462	Intermediate Similarity	NPC191976
0.8462	Intermediate Similarity	NPC86524
0.8456	Intermediate Similarity	NPC476821
0.8451	Intermediate Similarity	NPC474519
0.8446	Intermediate Similarity	NPC28632
0.8442	Intermediate Similarity	NPC37543
0.8442	Intermediate Similarity	NPC199463
0.844	Intermediate Similarity	NPC175738
0.8429	Intermediate Similarity	NPC259942
0.8425	Intermediate Similarity	NPC246638
0.8425	Intermediate Similarity	NPC92079
0.8425	Intermediate Similarity	NPC290550
0.8425	Intermediate Similarity	NPC305845
0.8425	Intermediate Similarity	NPC204045
0.8421	Intermediate Similarity	NPC312338
0.8421	Intermediate Similarity	NPC149889
0.8417	Intermediate Similarity	NPC41263
0.8417	Intermediate Similarity	NPC24869
0.8414	Intermediate Similarity	NPC143438
0.8411	Intermediate Similarity	NPC103509
0.8403	Intermediate Similarity	NPC170742
0.8392	Intermediate Similarity	NPC258502
0.8389	Intermediate Similarity	NPC136878
0.838	Intermediate Similarity	NPC267205
0.838	Intermediate Similarity	NPC180261
0.838	Intermediate Similarity	NPC37299
0.8377	Intermediate Similarity	NPC77807
0.8377	Intermediate Similarity	NPC14561
0.8377	Intermediate Similarity	NPC5379
0.8369	Intermediate Similarity	NPC17083
0.8367	Intermediate Similarity	NPC73061
0.8366	Intermediate Similarity	NPC93552
0.8356	Intermediate Similarity	NPC156872
0.8355	Intermediate Similarity	NPC46882
0.8355	Intermediate Similarity	NPC132990
0.8345	Intermediate Similarity	NPC165191
0.8345	Intermediate Similarity	NPC297797
0.8345	Intermediate Similarity	NPC245760
0.8345	Intermediate Similarity	NPC157284
0.8345	Intermediate Similarity	NPC477849
0.8345	Intermediate Similarity	NPC289358
0.8345	Intermediate Similarity	NPC42384
0.8345	Intermediate Similarity	NPC107672
0.8345	Intermediate Similarity	NPC51531
0.8345	Intermediate Similarity	NPC23667
0.8345	Intermediate Similarity	NPC473779
0.8345	Intermediate Similarity	NPC149773
0.8345	Intermediate Similarity	NPC469857
0.8345	Intermediate Similarity	NPC91887
0.8345	Intermediate Similarity	NPC50615
0.8345	Intermediate Similarity	NPC114333
0.8345	Intermediate Similarity	NPC46242
0.8345	Intermediate Similarity	NPC473479
0.8345	Intermediate Similarity	NPC5014
0.8345	Intermediate Similarity	NPC28592
0.8333	Intermediate Similarity	NPC10842
0.8333	Intermediate Similarity	NPC10926
0.8333	Intermediate Similarity	NPC315275
0.8333	Intermediate Similarity	NPC474311
0.8333	Intermediate Similarity	NPC118919
0.8323	Intermediate Similarity	NPC179732
0.8323	Intermediate Similarity	NPC474637
0.8323	Intermediate Similarity	NPC178976
0.8323	Intermediate Similarity	NPC201127
0.8322	Intermediate Similarity	NPC34482
0.8312	Intermediate Similarity	NPC38898
0.831	Intermediate Similarity	NPC478190
0.8309	Intermediate Similarity	NPC226275
0.8299	Intermediate Similarity	NPC110810
0.8298	Intermediate Similarity	NPC17840
0.8298	Intermediate Similarity	NPC247477
0.8289	Intermediate Similarity	NPC85131
0.8288	Intermediate Similarity	NPC294330
0.8288	Intermediate Similarity	NPC471819
0.8288	Intermediate Similarity	NPC190457
0.8276	Intermediate Similarity	NPC474771
0.8276	Intermediate Similarity	NPC53001
0.8276	Intermediate Similarity	NPC149372
0.8276	Intermediate Similarity	NPC65837
0.8276	Intermediate Similarity	NPC474849
0.8276	Intermediate Similarity	NPC178467
0.8273	Intermediate Similarity	NPC1991
0.8273	Intermediate Similarity	NPC15837
0.8273	Intermediate Similarity	NPC8745
0.8269	Intermediate Similarity	NPC245891
0.8269	Intermediate Similarity	NPC104876
0.8267	Intermediate Similarity	NPC470570
0.8267	Intermediate Similarity	NPC476535
0.8261	Intermediate Similarity	NPC310540
0.8258	Intermediate Similarity	NPC475799
0.8258	Intermediate Similarity	NPC13779
0.8255	Intermediate Similarity	NPC193703
0.8255	Intermediate Similarity	NPC21599
0.8255	Intermediate Similarity	NPC48762
0.8252	Intermediate Similarity	NPC138472
0.8252	Intermediate Similarity	NPC254603
0.825	Intermediate Similarity	NPC107009
0.8248	Intermediate Similarity	NPC91105
0.8247	Intermediate Similarity	NPC477048
0.8247	Intermediate Similarity	NPC477047
0.8247	Intermediate Similarity	NPC472211
0.8247	Intermediate Similarity	NPC155686
0.8243	Intermediate Similarity	NPC248068
0.8243	Intermediate Similarity	NPC474961
0.8235	Intermediate Similarity	NPC149246
0.8231	Intermediate Similarity	NPC473527
0.8227	Intermediate Similarity	NPC474998
0.8227	Intermediate Similarity	NPC278928
0.8227	Intermediate Similarity	NPC109123
0.8221	Intermediate Similarity	NPC245975
0.8219	Intermediate Similarity	NPC13715
0.8219	Intermediate Similarity	NPC475974
0.8219	Intermediate Similarity	NPC472403
0.8219	Intermediate Similarity	NPC9121
0.8219	Intermediate Similarity	NPC177307
0.8219	Intermediate Similarity	NPC4214
0.8219	Intermediate Similarity	NPC87723
0.8217	Intermediate Similarity	NPC84571
0.8214	Intermediate Similarity	NPC156539
0.8214	Intermediate Similarity	NPC100067
0.8214	Intermediate Similarity	NPC103356
0.8214	Intermediate Similarity	NPC266689
0.8214	Intermediate Similarity	NPC23126
0.8214	Intermediate Similarity	NPC30501
0.8214	Intermediate Similarity	NPC98254
0.8214	Intermediate Similarity	NPC105157
0.8214	Intermediate Similarity	NPC214620
0.8214	Intermediate Similarity	NPC72158
0.8214	Intermediate Similarity	NPC190043
0.8214	Intermediate Similarity	NPC169250
0.8214	Intermediate Similarity	NPC162612
0.8212	Intermediate Similarity	NPC77598
0.8212	Intermediate Similarity	NPC37709
0.8207	Intermediate Similarity	NPC7464
0.8205	Intermediate Similarity	NPC273843
0.8201	Intermediate Similarity	NPC262671
0.8201	Intermediate Similarity	NPC201728

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 NPC291078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	1036
0.2-0.3	1893
0.3-0.4	3017
0.4-0.5	1637
0.5-0.6	878
0.6-0.7	269
0.7-0.8	60
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8857	High Similarity	NPD651	Clinical (unspecified phase)
0.8705	High Similarity	NPD943	Approved
0.8592	High Similarity	NPD1509	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7390	Discontinued
0.7943	Intermediate Similarity	NPD1470	Approved
0.7911	Intermediate Similarity	NPD3882	Suspended
0.7857	Intermediate Similarity	NPD9269	Phase 2
0.7792	Intermediate Similarity	NPD1512	Approved
0.7785	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6232	Discontinued
0.7744	Intermediate Similarity	NPD7473	Discontinued
0.7737	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2801	Approved
0.7662	Intermediate Similarity	NPD1511	Approved
0.766	Intermediate Similarity	NPD1201	Approved
0.7635	Intermediate Similarity	NPD230	Phase 1
0.761	Intermediate Similarity	NPD1934	Approved
0.7597	Intermediate Similarity	NPD3300	Phase 2
0.7571	Intermediate Similarity	NPD9268	Approved
0.7566	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5406	Approved
0.755	Intermediate Similarity	NPD5408	Approved
0.755	Intermediate Similarity	NPD5405	Approved
0.755	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2533	Approved
0.747	Intermediate Similarity	NPD6166	Phase 2
0.747	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1607	Approved
0.745	Intermediate Similarity	NPD1240	Approved
0.7403	Intermediate Similarity	NPD2800	Approved
0.7368	Intermediate Similarity	NPD1510	Phase 2
0.7368	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7819	Suspended
0.7346	Intermediate Similarity	NPD1465	Phase 2
0.7317	Intermediate Similarity	NPD7075	Discontinued
0.7301	Intermediate Similarity	NPD3817	Phase 2
0.7289	Intermediate Similarity	NPD6959	Discontinued
0.7278	Intermediate Similarity	NPD3818	Discontinued
0.7267	Intermediate Similarity	NPD6599	Discontinued
0.7267	Intermediate Similarity	NPD4380	Phase 2
0.7256	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6651	Approved
0.7215	Intermediate Similarity	NPD6799	Approved
0.7205	Intermediate Similarity	NPD3226	Approved
0.7203	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3926	Phase 2
0.7195	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1247	Approved
0.7178	Intermediate Similarity	NPD6801	Discontinued
0.717	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6797	Phase 2
0.7134	Intermediate Similarity	NPD3750	Approved
0.7126	Intermediate Similarity	NPD5494	Approved
0.7117	Intermediate Similarity	NPD7411	Suspended
0.7115	Intermediate Similarity	NPD1549	Phase 2
0.711	Intermediate Similarity	NPD7251	Discontinued
0.7101	Intermediate Similarity	NPD4750	Phase 3
0.7097	Intermediate Similarity	NPD2935	Discontinued
0.7095	Intermediate Similarity	NPD1164	Approved
0.7093	Intermediate Similarity	NPD7074	Phase 3
0.7069	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1471	Phase 3
0.7035	Intermediate Similarity	NPD7054	Approved
0.7035	Intermediate Similarity	NPD5844	Phase 1
0.7034	Intermediate Similarity	NPD2932	Approved
0.7025	Intermediate Similarity	NPD8166	Discontinued
0.7025	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3749	Approved
0.7006	Intermediate Similarity	NPD8150	Discontinued
0.6994	Remote Similarity	NPD7472	Approved
0.6987	Remote Similarity	NPD2796	Approved
0.6981	Remote Similarity	NPD6190	Approved
0.6971	Remote Similarity	NPD7808	Phase 3
0.6964	Remote Similarity	NPD919	Approved
0.6959	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2344	Approved
0.6941	Remote Similarity	NPD5711	Approved
0.6941	Remote Similarity	NPD5710	Approved
0.6932	Remote Similarity	NPD5035	Approved
0.6927	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3019	Approved
0.6905	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD9494	Approved
0.6879	Remote Similarity	NPD6100	Approved
0.6879	Remote Similarity	NPD6099	Approved
0.6875	Remote Similarity	NPD5032	Approved
0.6864	Remote Similarity	NPD6234	Discontinued
0.686	Remote Similarity	NPD2403	Approved
0.6857	Remote Similarity	NPD3021	Approved
0.6857	Remote Similarity	NPD3022	Approved
0.6839	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD447	Suspended
0.6835	Remote Similarity	NPD2346	Discontinued
0.6818	Remote Similarity	NPD5027	Approved
0.6818	Remote Similarity	NPD5031	Approved
0.6818	Remote Similarity	NPD5029	Approved
0.6815	Remote Similarity	NPD2799	Discontinued
0.6815	Remote Similarity	NPD3748	Approved
0.6786	Remote Similarity	NPD9266	Approved
0.6786	Remote Similarity	NPD74	Approved
0.6786	Remote Similarity	NPD5402	Approved
0.6782	Remote Similarity	NPD3751	Discontinued
0.678	Remote Similarity	NPD4955	Approved
0.678	Remote Similarity	NPD4954	Approved
0.678	Remote Similarity	NPD5034	Approved
0.678	Remote Similarity	NPD5026	Approved
0.678	Remote Similarity	NPD36	Approved
0.678	Remote Similarity	NPD5028	Approved
0.6776	Remote Similarity	NPD6535	Approved
0.6776	Remote Similarity	NPD6534	Approved
0.677	Remote Similarity	NPD2309	Approved
0.6768	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD37	Approved
0.676	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD9493	Approved
0.6753	Remote Similarity	NPD3764	Approved
0.675	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1243	Approved
0.6746	Remote Similarity	NPD7768	Phase 2
0.6743	Remote Similarity	NPD6020	Phase 2
0.6723	Remote Similarity	NPD6559	Discontinued
0.6723	Remote Similarity	NPD5030	Phase 2
0.6722	Remote Similarity	NPD5038	Approved
0.6722	Remote Similarity	NPD8434	Phase 2
0.6722	Remote Similarity	NPD5037	Approved
0.6715	Remote Similarity	NPD846	Approved
0.6715	Remote Similarity	NPD940	Approved
0.6714	Remote Similarity	NPD9267	Approved
0.6714	Remote Similarity	NPD9264	Approved
0.6714	Remote Similarity	NPD9263	Approved
0.6714	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6781	Approved
0.6684	Remote Similarity	NPD6780	Approved
0.6684	Remote Similarity	NPD6782	Approved
0.6684	Remote Similarity	NPD6777	Approved
0.6684	Remote Similarity	NPD6778	Approved
0.6684	Remote Similarity	NPD6776	Approved
0.6684	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD5953	Discontinued
0.6667	Remote Similarity	NPD7700	Phase 2
0.6667	Remote Similarity	NPD5036	Approved
0.6647	Remote Similarity	NPD4965	Approved
0.6647	Remote Similarity	NPD4966	Approved
0.6647	Remote Similarity	NPD4967	Phase 2
0.6623	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD4628	Phase 3
0.6601	Remote Similarity	NPD2798	Approved
0.6591	Remote Similarity	NPD7228	Approved
0.6581	Remote Similarity	NPD3027	Phase 3
0.658	Remote Similarity	NPD8151	Discontinued
0.6579	Remote Similarity	NPD7435	Discontinued
0.6558	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6836	Approved
0.6556	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD9545	Approved
0.6554	Remote Similarity	NPD7286	Phase 2
0.6545	Remote Similarity	NPD8319	Approved
0.6545	Remote Similarity	NPD8320	Phase 1
0.6545	Remote Similarity	NPD5401	Approved
0.6543	Remote Similarity	NPD2654	Approved
0.6534	Remote Similarity	NPD5033	Approved
0.6533	Remote Similarity	NPD3026	Approved
0.6533	Remote Similarity	NPD3023	Approved
0.6517	Remote Similarity	NPD4956	Approved
0.6516	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.651	Remote Similarity	NPD3024	Approved
0.651	Remote Similarity	NPD3025	Approved
0.6507	Remote Similarity	NPD9281	Approved
0.6494	Remote Similarity	NPD7199	Phase 2
0.6492	Remote Similarity	NPD7696	Phase 3
0.6492	Remote Similarity	NPD7697	Approved
0.6492	Remote Similarity	NPD7698	Approved
0.6486	Remote Similarity	NPD5968	Phase 3
0.6474	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7870	Phase 2
0.6458	Remote Similarity	NPD7871	Phase 2
0.6457	Remote Similarity	NPD3787	Discontinued
0.6447	Remote Similarity	NPD3972	Approved
0.6447	Remote Similarity	NPD9717	Approved
0.6446	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5039	Approved
0.6443	Remote Similarity	NPD7701	Phase 2
0.6433	Remote Similarity	NPD6859	Clinical (unspecified phase)

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