NPASS Compound

Structure

NPC469871 OpenBabel07101719252D 41 43 0 0 1 0 0 0 0 0999 V2000 0.5991 2.5373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6039 -0.1734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 3.3686 2.3595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3283 3.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5234 1.8250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1735 3.8931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0983 1.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5981 1.0647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5637 0.8258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1333 4.8923 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5446 0.8918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6231 -1.0503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5187 1.5405 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1116 1.3426 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1981 -0.8053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7185 0.2914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2478 5.3570 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.6460 2.1878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7989 -1.6047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4753 -1.8798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5935 -0.3211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 35 1 0 0 0 0 5 36 1 0 0 0 0 6 37 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 13 29 1 0 0 0 0 14 31 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 22 1 0 0 0 0 16 30 1 0 0 0 0 17 23 1 0 0 0 0 17 29 1 0 0 0 0 18 24 1 0 0 0 0 18 30 1 0 0 0 0 19 1 1 1 0 0 0 19 23 1 0 0 0 0 20 2 1 1 0 0 0 20 25 1 0 0 0 0 20 38 1 0 0 0 0 21 12 1 6 0 0 0 21 40 1 0 0 0 0 22 39 1 6 0 0 0 23 32 1 6 0 0 0 24 33 2 0 0 0 0 24 41 1 0 0 0 0 25 26 1 0 0 0 0 25 35 1 6 0 0 0 26 27 1 0 0 0 0 26 36 1 1 0 0 0 27 28 1 0 0 0 0 27 37 1 1 0 0 0 28 38 1 0 0 0 0 28 39 1 6 0 0 0 29 3 1 6 0 0 0 29 41 1 0 0 0 0 30 34 1 1 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	648.25
Volume:	601.043
LogP:	3.455
LogD:	3.223
LogS:	-4.785
# Rotatable Bonds:	9
TPSA:	122.14
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.278
Synthetic Accessibility Score:	6.757
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.92
MDCK Permeability:	8.706118387635797e-05
Pgp-inhibitor:	0.776
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.246

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	76.59247589111328%
Volume Distribution (VD):	0.644
Pgp-substrate:	14.37713623046875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.762
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.551
CYP3A4-substrate:	0.828

ADMET: Excretion

Clearance (CL):	6.985
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.897
Human Hepatotoxicity (H-HT):	0.785
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.797
Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.933
Carcinogencity:	0.107
Eye Corrosion:	0.009
Eye Irritation:	0.021
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC469871

Natural Product ID:	NPC469871
*Common Name:**	18Z-Lyngbyaloside C
IUPAC Name:	(1S,4R,5R,7R,11S,13R)-7-[(3E,5Z)-6-bromohexa-3,5-dienyl]-5,11-dihydroxy-4,7-dimethyl-13-[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy-8,15-dioxabicyclo[9.3.1]pentadecan-9-one
Synonyms:	18Z-Lyngbyaloside C
Standard InCHIKey:	CKTXZFBKOQGTIC-NVXQDTFASA-N
Standard InCHI:	InChI=1S/C30H49BrO10/c1-19-11-12-21-15-22(39-28-27(37-6)26(36-5)25(35-4)20(2)38-28)16-30(34,40-21)18-24(33)41-29(3,17-23(19)32)13-9-7-8-10-14-31/h7-8,10,14,19-23,25-28,32,34H,9,11-13,15-18H2,1-6H3/b8-7+,14-10-/t19-,20+,21+,22-,23-,25+,26-,27-,28+,29-,30+/m1/s1
SMILES:	CC1CCC2CC(CC(O2)(CC(=O)OC(CC1O)(C)CCC=CC=CBr)O)OC3C(C(C(C(O3)C)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223737
PubChem CID:	46939690
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO30186	Lyngbya bouillonii	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18461997]
NPO30186	Lyngbya bouillonii	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[20131814]
NPO30186	Lyngbya bouillonii	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20704304]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	100000.0	nM	PMID[499316]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	53000.0	nM	PMID[499316]

☑ 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 NPC469871 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	215
0.1-0.2	1136
0.2-0.3	4986
0.3-0.4	9939
0.4-0.5	13503
0.5-0.6	9164
0.6-0.7	3506
0.7-0.8	237
0.8-0.85	5
0.85-0.9	0
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469870
0.9381	High Similarity	NPC469869
0.8351	Intermediate Similarity	NPC478036
0.8351	Intermediate Similarity	NPC478037
0.7979	Intermediate Similarity	NPC470313
0.7979	Intermediate Similarity	NPC156089
0.7979	Intermediate Similarity	NPC473500
0.7979	Intermediate Similarity	NPC38295
0.7941	Intermediate Similarity	NPC308567
0.7941	Intermediate Similarity	NPC261377
0.7941	Intermediate Similarity	NPC255592
0.7879	Intermediate Similarity	NPC472199
0.7857	Intermediate Similarity	NPC13710
0.783	Intermediate Similarity	NPC478038
0.78	Intermediate Similarity	NPC320089
0.7788	Intermediate Similarity	NPC476611
0.7778	Intermediate Similarity	NPC313670
0.7778	Intermediate Similarity	NPC313668
0.7778	Intermediate Similarity	NPC315836
0.7767	Intermediate Similarity	NPC83895
0.7767	Intermediate Similarity	NPC187761
0.7766	Intermediate Similarity	NPC21693
0.7766	Intermediate Similarity	NPC236649
0.7732	Intermediate Similarity	NPC477993
0.7732	Intermediate Similarity	NPC477994
0.7723	Intermediate Similarity	NPC472198
0.77	Intermediate Similarity	NPC472197
0.7685	Intermediate Similarity	NPC193765
0.7685	Intermediate Similarity	NPC473807
0.767	Intermediate Similarity	NPC278506
0.767	Intermediate Similarity	NPC476612
0.767	Intermediate Similarity	NPC472290
0.767	Intermediate Similarity	NPC476613
0.767	Intermediate Similarity	NPC40812
0.7664	Intermediate Similarity	NPC476738
0.7664	Intermediate Similarity	NPC476740
0.7653	Intermediate Similarity	NPC477959
0.7653	Intermediate Similarity	NPC86005
0.7652	Intermediate Similarity	NPC170880
0.7652	Intermediate Similarity	NPC183353
0.7652	Intermediate Similarity	NPC470829
0.7652	Intermediate Similarity	NPC473228
0.7652	Intermediate Similarity	NPC469812
0.7642	Intermediate Similarity	NPC473816
0.7642	Intermediate Similarity	NPC309398
0.7642	Intermediate Similarity	NPC475367
0.7642	Intermediate Similarity	NPC474581
0.7632	Intermediate Similarity	NPC477515
0.7632	Intermediate Similarity	NPC67917
0.7632	Intermediate Similarity	NPC314268
0.7632	Intermediate Similarity	NPC313802
0.7629	Intermediate Similarity	NPC477746
0.7629	Intermediate Similarity	NPC477747
0.7573	Intermediate Similarity	NPC165332
0.7573	Intermediate Similarity	NPC180722
0.7573	Intermediate Similarity	NPC195645
0.757	Intermediate Similarity	NPC470519
0.757	Intermediate Similarity	NPC231271
0.7549	Intermediate Similarity	NPC71589
0.7525	Intermediate Similarity	NPC470379
0.7525	Intermediate Similarity	NPC470373
0.75	Intermediate Similarity	NPC256902
0.75	Intermediate Similarity	NPC118193
0.7458	Intermediate Similarity	NPC313333
0.7458	Intermediate Similarity	NPC314451
0.7458	Intermediate Similarity	NPC314512
0.7458	Intermediate Similarity	NPC313342
0.7436	Intermediate Similarity	NPC275343
0.7429	Intermediate Similarity	NPC70733
0.7429	Intermediate Similarity	NPC56071
0.7423	Intermediate Similarity	NPC69469
0.7404	Intermediate Similarity	NPC54731
0.74	Intermediate Similarity	NPC201046
0.7391	Intermediate Similarity	NPC475309
0.7387	Intermediate Similarity	NPC472508
0.7379	Intermediate Similarity	NPC5418
0.7374	Intermediate Similarity	NPC475753
0.7373	Intermediate Similarity	NPC314629
0.7373	Intermediate Similarity	NPC315783
0.7368	Intermediate Similarity	NPC263574
0.7368	Intermediate Similarity	NPC469747
0.7364	Intermediate Similarity	NPC475960
0.7364	Intermediate Similarity	NPC472507
0.734	Intermediate Similarity	NPC474003
0.734	Intermediate Similarity	NPC110813
0.7333	Intermediate Similarity	NPC314282
0.7327	Intermediate Similarity	NPC97577
0.7308	Intermediate Similarity	NPC108141
0.7297	Intermediate Similarity	NPC118225
0.7292	Intermediate Similarity	NPC103634
0.7292	Intermediate Similarity	NPC469920
0.729	Intermediate Similarity	NPC2313
0.729	Intermediate Similarity	NPC475655
0.729	Intermediate Similarity	NPC57586
0.729	Intermediate Similarity	NPC154127
0.729	Intermediate Similarity	NPC475157
0.729	Intermediate Similarity	NPC154132
0.729	Intermediate Similarity	NPC471637
0.7263	Intermediate Similarity	NPC133377
0.7257	Intermediate Similarity	NPC1046
0.7257	Intermediate Similarity	NPC80843
0.7257	Intermediate Similarity	NPC1111
0.7257	Intermediate Similarity	NPC261750
0.7257	Intermediate Similarity	NPC174836
0.7255	Intermediate Similarity	NPC473311
0.7238	Intermediate Similarity	NPC143446
0.7234	Intermediate Similarity	NPC469514
0.7234	Intermediate Similarity	NPC239127
0.7232	Intermediate Similarity	NPC83005
0.7228	Intermediate Similarity	NPC473151
0.7228	Intermediate Similarity	NPC137368
0.7222	Intermediate Similarity	NPC313569
0.7217	Intermediate Similarity	NPC473126
0.7213	Intermediate Similarity	NPC316205
0.7213	Intermediate Similarity	NPC315387
0.7212	Intermediate Similarity	NPC294293
0.7207	Intermediate Similarity	NPC473288
0.7203	Intermediate Similarity	NPC75417
0.7196	Intermediate Similarity	NPC324667
0.7193	Intermediate Similarity	NPC311592
0.7193	Intermediate Similarity	NPC475208
0.7193	Intermediate Similarity	NPC75167
0.7193	Intermediate Similarity	NPC238935
0.7184	Intermediate Similarity	NPC36491
0.7179	Intermediate Similarity	NPC114441
0.7179	Intermediate Similarity	NPC6377
0.7179	Intermediate Similarity	NPC39211
0.7179	Intermediate Similarity	NPC180550
0.7179	Intermediate Similarity	NPC135849
0.7179	Intermediate Similarity	NPC475171
0.7179	Intermediate Similarity	NPC469945
0.7179	Intermediate Similarity	NPC473884
0.7179	Intermediate Similarity	NPC214484
0.7179	Intermediate Similarity	NPC35405
0.7179	Intermediate Similarity	NPC51564
0.7179	Intermediate Similarity	NPC25663
0.7179	Intermediate Similarity	NPC11551
0.7179	Intermediate Similarity	NPC472949
0.7179	Intermediate Similarity	NPC157868
0.7179	Intermediate Similarity	NPC309780
0.7179	Intermediate Similarity	NPC208381
0.717	Intermediate Similarity	NPC266842
0.7168	Intermediate Similarity	NPC31839
0.7158	Intermediate Similarity	NPC281296
0.7156	Intermediate Similarity	NPC197736
0.7155	Intermediate Similarity	NPC6531
0.7143	Intermediate Similarity	NPC20072
0.713	Intermediate Similarity	NPC181145
0.713	Intermediate Similarity	NPC164389
0.713	Intermediate Similarity	NPC116024
0.713	Intermediate Similarity	NPC475486
0.7129	Intermediate Similarity	NPC314364
0.7128	Intermediate Similarity	NPC255060
0.7119	Intermediate Similarity	NPC476991
0.7117	Intermediate Similarity	NPC254538
0.7117	Intermediate Similarity	NPC293512
0.7117	Intermediate Similarity	NPC474285
0.7115	Intermediate Similarity	NPC472196
0.7115	Intermediate Similarity	NPC61201
0.7115	Intermediate Similarity	NPC472195
0.7115	Intermediate Similarity	NPC238090
0.7113	Intermediate Similarity	NPC100697
0.7105	Intermediate Similarity	NPC48249
0.7105	Intermediate Similarity	NPC161434
0.7105	Intermediate Similarity	NPC60432
0.7105	Intermediate Similarity	NPC195132
0.7103	Intermediate Similarity	NPC472015
0.7103	Intermediate Similarity	NPC203627
0.7097	Intermediate Similarity	NPC167145
0.7097	Intermediate Similarity	NPC326024
0.7094	Intermediate Similarity	NPC286347
0.7091	Intermediate Similarity	NPC472748
0.7091	Intermediate Similarity	NPC239162
0.7091	Intermediate Similarity	NPC474917
0.7087	Intermediate Similarity	NPC202886
0.7083	Intermediate Similarity	NPC11796
0.7083	Intermediate Similarity	NPC218817
0.7083	Intermediate Similarity	NPC121200
0.708	Intermediate Similarity	NPC270667
0.708	Intermediate Similarity	NPC475296
0.708	Intermediate Similarity	NPC29069
0.708	Intermediate Similarity	NPC127056
0.708	Intermediate Similarity	NPC90856
0.708	Intermediate Similarity	NPC242611
0.708	Intermediate Similarity	NPC174679
0.708	Intermediate Similarity	NPC269095
0.708	Intermediate Similarity	NPC279554
0.708	Intermediate Similarity	NPC164194
0.708	Intermediate Similarity	NPC56713
0.708	Intermediate Similarity	NPC136877
0.708	Intermediate Similarity	NPC59804
0.708	Intermediate Similarity	NPC46407
0.708	Intermediate Similarity	NPC474589
0.708	Intermediate Similarity	NPC78046
0.7075	Intermediate Similarity	NPC306041
0.7075	Intermediate Similarity	NPC469369
0.7075	Intermediate Similarity	NPC256230
0.7075	Intermediate Similarity	NPC469528
0.7069	Intermediate Similarity	NPC37134
0.7069	Intermediate Similarity	NPC75287

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 NPC469871 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1525
0.2-0.3	3969
0.3-0.4	2271
0.4-0.5	744
0.5-0.6	357
0.6-0.7	75
0.7-0.8	23
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
0.7879	Intermediate Similarity	NPD7983	Approved
0.7652	Intermediate Similarity	NPD8517	Approved
0.7652	Intermediate Similarity	NPD8515	Approved
0.7652	Intermediate Similarity	NPD8513	Phase 3
0.7652	Intermediate Similarity	NPD8516	Approved
0.7573	Intermediate Similarity	NPD7839	Suspended
0.7458	Intermediate Similarity	NPD8342	Approved
0.7458	Intermediate Similarity	NPD8340	Approved
0.7458	Intermediate Similarity	NPD8299	Approved
0.7458	Intermediate Similarity	NPD8341	Approved
0.7429	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD8451	Approved
0.7373	Intermediate Similarity	NPD7830	Approved
0.7373	Intermediate Similarity	NPD7829	Approved
0.7333	Intermediate Similarity	NPD8448	Approved
0.7327	Intermediate Similarity	NPD6101	Approved
0.7327	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5779	Approved
0.7282	Intermediate Similarity	NPD5778	Approved
0.7203	Intermediate Similarity	NPD8444	Approved
0.7184	Intermediate Similarity	NPD6411	Approved
0.7154	Intermediate Similarity	NPD8392	Approved
0.7154	Intermediate Similarity	NPD8390	Approved
0.7154	Intermediate Similarity	NPD8391	Approved
0.7094	Intermediate Similarity	NPD7641	Discontinued
0.7087	Intermediate Similarity	NPD6698	Approved
0.7087	Intermediate Similarity	NPD46	Approved
0.7054	Intermediate Similarity	NPD6686	Approved
0.7049	Intermediate Similarity	NPD8074	Phase 3
0.7018	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8137	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD8328	Phase 3
0.6864	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7642	Approved
0.68	Remote Similarity	NPD6435	Approved
0.6777	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8080	Discontinued
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6607	Remote Similarity	NPD8085	Approved
0.6607	Remote Similarity	NPD8084	Approved
0.6607	Remote Similarity	NPD8139	Approved
0.6607	Remote Similarity	NPD8083	Approved
0.6607	Remote Similarity	NPD8086	Approved
0.6607	Remote Similarity	NPD8082	Approved
0.6607	Remote Similarity	NPD8138	Approved
0.6604	Remote Similarity	NPD7838	Discovery
0.66	Remote Similarity	NPD5368	Approved
0.6587	Remote Similarity	NPD7736	Approved
0.6585	Remote Similarity	NPD6370	Approved
0.656	Remote Similarity	NPD7507	Approved
0.6552	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8276	Approved
0.6549	Remote Similarity	NPD8275	Approved
0.6535	Remote Similarity	NPD5369	Approved
0.6508	Remote Similarity	NPD8293	Discontinued
0.6491	Remote Similarity	NPD8081	Approved
0.648	Remote Similarity	NPD7492	Approved
0.6471	Remote Similarity	NPD8133	Approved
0.6466	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD8393	Approved
0.6429	Remote Similarity	NPD6616	Approved
0.6423	Remote Similarity	NPD6054	Approved
0.6389	Remote Similarity	NPD7637	Suspended
0.6381	Remote Similarity	NPD5786	Approved
0.6379	Remote Similarity	NPD8307	Discontinued
0.6379	Remote Similarity	NPD8140	Approved
0.6378	Remote Similarity	NPD7078	Approved
0.629	Remote Similarity	NPD6059	Approved
0.629	Remote Similarity	NPD6319	Approved
0.6273	Remote Similarity	NPD5282	Discontinued
0.6271	Remote Similarity	NPD8305	Approved
0.6271	Remote Similarity	NPD8306	Approved
0.625	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD7154	Phase 3
0.624	Remote Similarity	NPD6016	Approved
0.624	Remote Similarity	NPD6015	Approved
0.624	Remote Similarity	NPD7503	Approved
0.6239	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD8087	Discontinued
0.6197	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5988	Approved
0.6179	Remote Similarity	NPD6009	Approved
0.6176	Remote Similarity	NPD7329	Approved
0.6172	Remote Similarity	NPD8273	Phase 1
0.6168	Remote Similarity	NPD4251	Approved
0.6168	Remote Similarity	NPD4250	Approved
0.6154	Remote Similarity	NPD4270	Approved
0.6154	Remote Similarity	NPD4269	Approved
0.6132	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4820	Approved
0.6117	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4822	Approved
0.6117	Remote Similarity	NPD4821	Approved
0.6117	Remote Similarity	NPD4819	Approved
0.6116	Remote Similarity	NPD8297	Approved
0.6083	Remote Similarity	NPD6371	Approved
0.6077	Remote Similarity	NPD8336	Approved
0.6077	Remote Similarity	NPD8337	Approved
0.6075	Remote Similarity	NPD4249	Approved
0.6075	Remote Similarity	NPD6422	Discontinued
0.6071	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD3181	Approved
0.6045	Remote Similarity	NPD8415	Approved
0.6042	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD898	Approved
0.6042	Remote Similarity	NPD897	Approved
0.6042	Remote Similarity	NPD896	Approved
0.6034	Remote Similarity	NPD8300	Approved
0.6034	Remote Similarity	NPD8301	Approved
0.6032	Remote Similarity	NPD8377	Approved
0.6032	Remote Similarity	NPD8294	Approved
0.6017	Remote Similarity	NPD5048	Discontinued
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7328	Approved
0.5984	Remote Similarity	NPD6053	Discontinued
0.5984	Remote Similarity	NPD8380	Approved
0.5984	Remote Similarity	NPD8269	Approved
0.5984	Remote Similarity	NPD8379	Approved
0.5984	Remote Similarity	NPD8378	Approved
0.5984	Remote Similarity	NPD8268	Approved
0.5984	Remote Similarity	NPD8033	Approved
0.5984	Remote Similarity	NPD8296	Approved
0.5984	Remote Similarity	NPD8267	Approved
0.5984	Remote Similarity	NPD8335	Approved
0.5984	Remote Similarity	NPD6921	Approved
0.5984	Remote Similarity	NPD8266	Approved
0.5981	Remote Similarity	NPD5363	Approved
0.5962	Remote Similarity	NPD4252	Approved
0.5952	Remote Similarity	NPD7516	Approved
0.5943	Remote Similarity	NPD3669	Approved
0.5943	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5362	Discontinued
0.5935	Remote Similarity	NPD4632	Approved
0.5922	Remote Similarity	NPD4271	Approved
0.5922	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4268	Approved
0.592	Remote Similarity	NPD7500	Approved
0.5917	Remote Similarity	NPD6899	Approved
0.5917	Remote Similarity	NPD6881	Approved
0.5905	Remote Similarity	NPD1780	Approved
0.5905	Remote Similarity	NPD1779	Approved
0.5902	Remote Similarity	NPD6650	Approved
0.5902	Remote Similarity	NPD6649	Approved
0.5896	Remote Similarity	NPD8338	Approved
0.5895	Remote Similarity	NPD3197	Phase 1
0.5882	Remote Similarity	NPD7128	Approved
0.5882	Remote Similarity	NPD6675	Approved
0.5882	Remote Similarity	NPD5739	Approved
0.5882	Remote Similarity	NPD6402	Approved
0.5868	Remote Similarity	NPD6373	Approved
0.5868	Remote Similarity	NPD6372	Approved
0.5862	Remote Similarity	NPD6648	Approved
0.5856	Remote Similarity	NPD5785	Approved
0.5833	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD6033	Approved
0.582	Remote Similarity	NPD7290	Approved
0.582	Remote Similarity	NPD7102	Approved
0.582	Remote Similarity	NPD6883	Approved
0.582	Remote Similarity	NPD6421	Discontinued
0.5812	Remote Similarity	NPD5344	Discontinued
0.5798	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7320	Approved
0.5784	Remote Similarity	NPD8039	Approved
0.5781	Remote Similarity	NPD8347	Approved
0.5781	Remote Similarity	NPD8345	Approved
0.5781	Remote Similarity	NPD8346	Approved
0.5773	Remote Similarity	NPD7331	Phase 2
0.5772	Remote Similarity	NPD6869	Approved
0.5772	Remote Similarity	NPD6847	Approved
0.5772	Remote Similarity	NPD6617	Approved
0.5772	Remote Similarity	NPD8130	Phase 1
0.5769	Remote Similarity	NPD7604	Phase 2
0.5769	Remote Similarity	NPD3732	Approved
0.5752	Remote Similarity	NPD6399	Phase 3
0.5741	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6013	Approved
0.5738	Remote Similarity	NPD6014	Approved
0.5738	Remote Similarity	NPD6012	Approved
0.5736	Remote Similarity	NPD5983	Phase 2
0.5727	Remote Similarity	NPD7524	Approved
0.5714	Remote Similarity	NPD6274	Approved
0.5714	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5704	Remote Similarity	NPD7260	Phase 2
0.5702	Remote Similarity	NPD5701	Approved
0.5702	Remote Similarity	NPD6685	Approved
0.5691	Remote Similarity	NPD4634	Approved
0.569	Remote Similarity	NPD6084	Phase 2
0.569	Remote Similarity	NPD6083	Phase 2
0.5682	Remote Similarity	NPD6336	Discontinued
0.5674	Remote Similarity	NPD8384	Approved
0.5669	Remote Similarity	NPD7115	Discovery
0.5664	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6011	Approved
0.5649	Remote Similarity	NPD6067	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data