NPASS Compound

Structure

NPC178949 OpenBabel07101719252D 35 37 0 0 1 0 0 0 0 0999 V2000 -2.5000 -4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3660 -6.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9641 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9641 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2321 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2321 -4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0981 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2321 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3660 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3660 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0981 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0981 -2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2321 -1.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2321 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3660 -0.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -0.0000 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 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 5 19 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 16 2 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 28 1 0 0 0 0 14 17 2 0 0 0 0 15 33 1 0 0 0 0 18 4 1 1 0 0 0 19 29 2 0 0 0 0 19 33 1 0 0 0 0 20 18 1 1 0 0 0 20 21 1 0 0 0 0 21 14 1 6 0 0 0 21 22 1 0 0 0 0 22 28 1 6 0 0 0 23 15 1 1 0 0 0 23 24 1 0 0 0 0 23 34 1 0 0 0 0 24 25 1 0 0 0 0 24 30 1 1 0 0 0 25 26 1 0 0 0 0 25 31 1 1 0 0 0 26 27 1 0 0 0 0 26 32 1 6 0 0 0 27 34 1 0 0 0 0 27 35 1 1 0 0 0 28 6 1 6 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.32
Volume:	520.797
LogP:	5.701
LogD:	4.383
LogS:	-4.195
# Rotatable Bonds:	9
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.347
Synthetic Accessibility Score:	4.955
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.786
MDCK Permeability:	3.799773185164668e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.743
20% Bioavailability (F20%):	0.076
30% Bioavailability (F30%):	0.164

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	88.63980865478516%
Volume Distribution (VD):	1.242
Pgp-substrate:	4.4956889152526855%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.75
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.187
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	2.638
Half-life (T1/2):	0.458

ADMET: Toxicity

hERG Blockers:	0.376
Human Hepatotoxicity (H-HT):	0.683
Drug-inuced Liver Injury (DILI):	0.341
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.091
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.619
Carcinogencity:	0.082
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC178949

Natural Product ID:	NPC178949
*Common Name:**	Lemnaloside A
IUPAC Name:	[(2R,3R,4S,5R,6S)-6-[[(1S,4S,4aR,8aS)-1,6-dimethyl-4-[(2R)-6-methylhept-5-en-2-yl]-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
Synonyms:
Standard InCHIKey:	NUFWENCOYDWSEV-FTWLUMHOSA-N
Standard InCHI:	InChI=1S/C28H46O7/c1-16(2)8-7-9-18(4)20-12-13-28(6,22-11-10-17(3)14-21(20)22)35-27-26(32)25(31)24(30)23(34-27)15-33-19(5)29/h8,14,18,20-27,30-32H,7,9-13,15H2,1-6H3/t18-,20+,21+,22+,23-,24+,25+,26-,27+,28+/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@@H]1CC[C@@](C)([C@H]2CCC(=C[C@@H]12)C)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](COC(=O)C)O1)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226094
PubChem CID:	16737221
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO33496	lemnalia sp.	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17506585]
NPO33496	lemnalia sp.	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18247571]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	11.0	mm	PMID[448495]

☑ 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 NPC178949 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	203
0.1-0.2	1429
0.2-0.3	4862
0.3-0.4	10788
0.4-0.5	11402
0.5-0.6	6296
0.6-0.7	5349
0.7-0.8	2226
0.8-0.85	107
0.85-0.9	32
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC96736
0.9333	High Similarity	NPC211238
0.914	High Similarity	NPC477928
0.9032	High Similarity	NPC96597
0.9032	High Similarity	NPC309503
0.9032	High Similarity	NPC125551
0.9032	High Similarity	NPC155319
0.9032	High Similarity	NPC239547
0.9032	High Similarity	NPC91197
0.8969	High Similarity	NPC470763
0.8969	High Similarity	NPC470767
0.8913	High Similarity	NPC305160
0.8866	High Similarity	NPC470768
0.8866	High Similarity	NPC31430
0.8866	High Similarity	NPC85593
0.8866	High Similarity	NPC173583
0.8854	High Similarity	NPC470571
0.8776	High Similarity	NPC473199
0.875	High Similarity	NPC280991
0.8723	High Similarity	NPC90583
0.871	High Similarity	NPC477927
0.871	High Similarity	NPC72817
0.8696	High Similarity	NPC302584
0.8687	High Similarity	NPC293512
0.866	High Similarity	NPC154452
0.8652	High Similarity	NPC477747
0.8652	High Similarity	NPC477746
0.8617	High Similarity	NPC230347
0.8617	High Similarity	NPC286612
0.8617	High Similarity	NPC275310
0.8602	High Similarity	NPC474792
0.8602	High Similarity	NPC91654
0.8602	High Similarity	NPC67398
0.86	High Similarity	NPC472988
0.86	High Similarity	NPC38217
0.8557	High Similarity	NPC21064
0.8557	High Similarity	NPC121072
0.8556	High Similarity	NPC470836
0.8542	High Similarity	NPC5358
0.8542	High Similarity	NPC216260
0.8539	High Similarity	NPC166279
0.8515	High Similarity	NPC167383
0.8515	High Similarity	NPC125361
0.8515	High Similarity	NPC57362
0.8515	High Similarity	NPC137917
0.8515	High Similarity	NPC51925
0.8515	High Similarity	NPC204407
0.8515	High Similarity	NPC237503
0.8515	High Similarity	NPC43976
0.8515	High Similarity	NPC296761
0.8515	High Similarity	NPC306746
0.8515	High Similarity	NPC154085
0.8506	High Similarity	NPC100697
0.85	High Similarity	NPC283849
0.85	High Similarity	NPC234160
0.85	High Similarity	NPC472390
0.8485	Intermediate Similarity	NPC470060
0.8485	Intermediate Similarity	NPC470057
0.8485	Intermediate Similarity	NPC470064
0.8485	Intermediate Similarity	NPC470061
0.8485	Intermediate Similarity	NPC470062
0.8485	Intermediate Similarity	NPC470043
0.8485	Intermediate Similarity	NPC470058
0.8485	Intermediate Similarity	NPC470059
0.8454	Intermediate Similarity	NPC64348
0.8447	Intermediate Similarity	NPC37739
0.8447	Intermediate Similarity	NPC46388
0.8438	Intermediate Similarity	NPC240372
0.8431	Intermediate Similarity	NPC279554
0.8431	Intermediate Similarity	NPC476881
0.8431	Intermediate Similarity	NPC59804
0.8431	Intermediate Similarity	NPC476886
0.8431	Intermediate Similarity	NPC475296
0.8431	Intermediate Similarity	NPC129340
0.8431	Intermediate Similarity	NPC90856
0.8431	Intermediate Similarity	NPC476887
0.8431	Intermediate Similarity	NPC7870
0.8431	Intermediate Similarity	NPC476880
0.8431	Intermediate Similarity	NPC110139
0.8431	Intermediate Similarity	NPC127056
0.8431	Intermediate Similarity	NPC78046
0.8431	Intermediate Similarity	NPC274507
0.8431	Intermediate Similarity	NPC101450
0.8431	Intermediate Similarity	NPC476882
0.8431	Intermediate Similarity	NPC476883
0.8431	Intermediate Similarity	NPC75747
0.8431	Intermediate Similarity	NPC474589
0.8431	Intermediate Similarity	NPC102914
0.8431	Intermediate Similarity	NPC270667
0.8431	Intermediate Similarity	NPC220984
0.8431	Intermediate Similarity	NPC476884
0.8431	Intermediate Similarity	NPC56713
0.8431	Intermediate Similarity	NPC136877
0.8431	Intermediate Similarity	NPC164194
0.8431	Intermediate Similarity	NPC199457
0.8431	Intermediate Similarity	NPC29069
0.8431	Intermediate Similarity	NPC476885
0.8431	Intermediate Similarity	NPC269095
0.8431	Intermediate Similarity	NPC68419
0.8431	Intermediate Similarity	NPC108709
0.8431	Intermediate Similarity	NPC174679
0.8416	Intermediate Similarity	NPC28198
0.8416	Intermediate Similarity	NPC476123
0.8416	Intermediate Similarity	NPC284807
0.8416	Intermediate Similarity	NPC177246
0.8404	Intermediate Similarity	NPC474835
0.8387	Intermediate Similarity	NPC202886
0.8367	Intermediate Similarity	NPC309425
0.8367	Intermediate Similarity	NPC88000
0.8367	Intermediate Similarity	NPC470054
0.8367	Intermediate Similarity	NPC117714
0.8367	Intermediate Similarity	NPC129372
0.8367	Intermediate Similarity	NPC472023
0.8367	Intermediate Similarity	NPC160734
0.8367	Intermediate Similarity	NPC4831
0.8367	Intermediate Similarity	NPC263756
0.8367	Intermediate Similarity	NPC47566
0.8365	Intermediate Similarity	NPC47063
0.8365	Intermediate Similarity	NPC138334
0.8365	Intermediate Similarity	NPC271138
0.8365	Intermediate Similarity	NPC269315
0.8365	Intermediate Similarity	NPC204458
0.8365	Intermediate Similarity	NPC189884
0.8351	Intermediate Similarity	NPC477875
0.8351	Intermediate Similarity	NPC234287
0.8351	Intermediate Similarity	NPC280825
0.8351	Intermediate Similarity	NPC477876
0.835	Intermediate Similarity	NPC263827
0.835	Intermediate Similarity	NPC179434
0.835	Intermediate Similarity	NPC65167
0.835	Intermediate Similarity	NPC297208
0.835	Intermediate Similarity	NPC250481
0.835	Intermediate Similarity	NPC114188
0.835	Intermediate Similarity	NPC31839
0.835	Intermediate Similarity	NPC191763
0.835	Intermediate Similarity	NPC285410
0.835	Intermediate Similarity	NPC30397
0.835	Intermediate Similarity	NPC235841
0.835	Intermediate Similarity	NPC211798
0.835	Intermediate Similarity	NPC164419
0.835	Intermediate Similarity	NPC473481
0.835	Intermediate Similarity	NPC108748
0.8333	Intermediate Similarity	NPC265655
0.8333	Intermediate Similarity	NPC127853
0.8317	Intermediate Similarity	NPC473538
0.8315	Intermediate Similarity	NPC20072
0.83	Intermediate Similarity	NPC470885
0.83	Intermediate Similarity	NPC187400
0.83	Intermediate Similarity	NPC221562
0.8283	Intermediate Similarity	NPC470053
0.8283	Intermediate Similarity	NPC30289
0.8283	Intermediate Similarity	NPC76497
0.8283	Intermediate Similarity	NPC136816
0.8283	Intermediate Similarity	NPC256133
0.8283	Intermediate Similarity	NPC213674
0.828	Intermediate Similarity	NPC473058
0.828	Intermediate Similarity	NPC477748
0.8269	Intermediate Similarity	NPC116794
0.8269	Intermediate Similarity	NPC104400
0.8269	Intermediate Similarity	NPC79718
0.8269	Intermediate Similarity	NPC139044
0.8269	Intermediate Similarity	NPC475504
0.8269	Intermediate Similarity	NPC109079
0.8269	Intermediate Similarity	NPC10320
0.8269	Intermediate Similarity	NPC104071
0.8269	Intermediate Similarity	NPC292677
0.8269	Intermediate Similarity	NPC174836
0.8269	Intermediate Similarity	NPC276093
0.8269	Intermediate Similarity	NPC139894
0.8269	Intermediate Similarity	NPC471967
0.8269	Intermediate Similarity	NPC473125
0.8269	Intermediate Similarity	NPC475516
0.8269	Intermediate Similarity	NPC257468
0.8269	Intermediate Similarity	NPC128925
0.8269	Intermediate Similarity	NPC1046
0.8269	Intermediate Similarity	NPC48249
0.8269	Intermediate Similarity	NPC102439
0.8269	Intermediate Similarity	NPC469946
0.8269	Intermediate Similarity	NPC473373
0.8269	Intermediate Similarity	NPC80843
0.8269	Intermediate Similarity	NPC256798
0.8269	Intermediate Similarity	NPC473383
0.8269	Intermediate Similarity	NPC471383
0.8269	Intermediate Similarity	NPC101744
0.8269	Intermediate Similarity	NPC324875
0.8265	Intermediate Similarity	NPC324598
0.8265	Intermediate Similarity	NPC473200
0.8265	Intermediate Similarity	NPC317019
0.8265	Intermediate Similarity	NPC7341
0.8252	Intermediate Similarity	NPC242611
0.8247	Intermediate Similarity	NPC471770
0.8247	Intermediate Similarity	NPC278939
0.8247	Intermediate Similarity	NPC243728
0.8247	Intermediate Similarity	NPC473555
0.8247	Intermediate Similarity	NPC473890
0.8235	Intermediate Similarity	NPC135015
0.8235	Intermediate Similarity	NPC295980
0.8235	Intermediate Similarity	NPC295389
0.8235	Intermediate Similarity	NPC195708
0.8235	Intermediate Similarity	NPC48548

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 NPC178949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1740
0.2-0.3	3964
0.3-0.4	2107
0.4-0.5	706
0.5-0.6	240
0.6-0.7	191
0.7-0.8	21
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
0.7981	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.789	Intermediate Similarity	NPD7328	Approved
0.789	Intermediate Similarity	NPD7327	Approved
0.7818	Intermediate Similarity	NPD7516	Approved
0.7788	Intermediate Similarity	NPD6412	Phase 2
0.7748	Intermediate Similarity	NPD8294	Approved
0.7748	Intermediate Similarity	NPD8377	Approved
0.7714	Intermediate Similarity	NPD6686	Approved
0.7679	Intermediate Similarity	NPD8033	Approved
0.7679	Intermediate Similarity	NPD8379	Approved
0.7679	Intermediate Similarity	NPD8378	Approved
0.7679	Intermediate Similarity	NPD8296	Approved
0.7679	Intermediate Similarity	NPD8335	Approved
0.7679	Intermediate Similarity	NPD8380	Approved
0.7679	Intermediate Similarity	NPD7503	Approved
0.7544	Intermediate Similarity	NPD8328	Phase 3
0.7477	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7507	Approved
0.7364	Intermediate Similarity	NPD8133	Approved
0.7308	Intermediate Similarity	NPD5344	Discontinued
0.7227	Intermediate Similarity	NPD7319	Approved
0.7217	Intermediate Similarity	NPD8517	Approved
0.7217	Intermediate Similarity	NPD8516	Approved
0.7217	Intermediate Similarity	NPD8513	Phase 3
0.7217	Intermediate Similarity	NPD8515	Approved
0.7203	Intermediate Similarity	NPD8293	Discontinued
0.7155	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD7736	Approved
0.7115	Intermediate Similarity	NPD7638	Approved
0.7083	Intermediate Similarity	NPD3669	Approved
0.7083	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7639	Approved
0.7048	Intermediate Similarity	NPD7640	Approved
0.7034	Intermediate Similarity	NPD7492	Approved
0.7033	Intermediate Similarity	NPD1811	Approved
0.7033	Intermediate Similarity	NPD1810	Approved
0.7021	Intermediate Similarity	NPD7645	Phase 2
0.7018	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6054	Approved
0.6983	Remote Similarity	NPD6059	Approved
0.6975	Remote Similarity	NPD6616	Approved
0.6964	Remote Similarity	NPD6882	Approved
0.6947	Remote Similarity	NPD7525	Registered
0.6931	Remote Similarity	NPD3168	Discontinued
0.6917	Remote Similarity	NPD7078	Approved
0.6909	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4632	Approved
0.6893	Remote Similarity	NPD7748	Approved
0.6887	Remote Similarity	NPD6648	Approved
0.6881	Remote Similarity	NPD6402	Approved
0.6881	Remote Similarity	NPD5739	Approved
0.6881	Remote Similarity	NPD7128	Approved
0.6881	Remote Similarity	NPD6675	Approved
0.6863	Remote Similarity	NPD7515	Phase 2
0.6857	Remote Similarity	NPD7902	Approved
0.6838	Remote Similarity	NPD6319	Approved
0.6832	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6101	Approved
0.6814	Remote Similarity	NPD8297	Approved
0.6807	Remote Similarity	NPD6067	Discontinued
0.6796	Remote Similarity	NPD6399	Phase 3
0.6792	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4225	Approved
0.678	Remote Similarity	NPD6015	Approved
0.678	Remote Similarity	NPD6016	Approved
0.6765	Remote Similarity	NPD46	Approved
0.6765	Remote Similarity	NPD6698	Approved
0.6757	Remote Similarity	NPD6899	Approved
0.6757	Remote Similarity	NPD7320	Approved
0.6757	Remote Similarity	NPD6881	Approved
0.6726	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5988	Approved
0.6703	Remote Similarity	NPD2254	Approved
0.6703	Remote Similarity	NPD2687	Approved
0.6703	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD2686	Approved
0.6699	Remote Similarity	NPD6411	Approved
0.6696	Remote Similarity	NPD6373	Approved
0.6696	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6639	Remote Similarity	NPD8074	Phase 3
0.6637	Remote Similarity	NPD7102	Approved
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6883	Approved
0.6637	Remote Similarity	NPD7290	Approved
0.6635	Remote Similarity	NPD5779	Approved
0.6635	Remote Similarity	NPD5778	Approved
0.6634	Remote Similarity	NPD7524	Approved
0.6602	Remote Similarity	NPD7838	Discovery
0.6581	Remote Similarity	NPD7115	Discovery
0.6579	Remote Similarity	NPD6869	Approved
0.6579	Remote Similarity	NPD6847	Approved
0.6579	Remote Similarity	NPD6649	Approved
0.6579	Remote Similarity	NPD8130	Phase 1
0.6579	Remote Similarity	NPD6650	Approved
0.6579	Remote Similarity	NPD6617	Approved
0.6571	Remote Similarity	NPD7900	Approved
0.6571	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6014	Approved
0.6549	Remote Similarity	NPD6012	Approved
0.6549	Remote Similarity	NPD6013	Approved
0.6542	Remote Similarity	NPD6083	Phase 2
0.6542	Remote Similarity	NPD6084	Phase 2
0.6531	Remote Similarity	NPD1779	Approved
0.6531	Remote Similarity	NPD1780	Approved
0.6529	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5983	Phase 2
0.65	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD8171	Discontinued
0.646	Remote Similarity	NPD6011	Approved
0.6455	Remote Similarity	NPD7632	Discontinued
0.6452	Remote Similarity	NPD6033	Approved
0.6435	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5357	Phase 1
0.6429	Remote Similarity	NPD6008	Approved
0.6423	Remote Similarity	NPD6336	Discontinued
0.6421	Remote Similarity	NPD6942	Approved
0.6421	Remote Similarity	NPD7339	Approved
0.6404	Remote Similarity	NPD371	Approved
0.64	Remote Similarity	NPD6695	Phase 3
0.6389	Remote Similarity	NPD4755	Approved
0.6381	Remote Similarity	NPD8035	Phase 2
0.6381	Remote Similarity	NPD8034	Phase 2
0.6381	Remote Similarity	NPD7983	Approved
0.6379	Remote Similarity	NPD6053	Discontinued
0.6373	Remote Similarity	NPD3618	Phase 1
0.6372	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5695	Phase 3
0.6354	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4634	Approved
0.6346	Remote Similarity	NPD5328	Approved
0.6346	Remote Similarity	NPD6051	Approved
0.6337	Remote Similarity	NPD4786	Approved
0.6321	Remote Similarity	NPD4202	Approved
0.6311	Remote Similarity	NPD3573	Approved
0.6306	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3667	Approved
0.6275	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5285	Approved
0.6273	Remote Similarity	NPD5286	Approved
0.6273	Remote Similarity	NPD4700	Approved
0.6273	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD8449	Approved
0.625	Remote Similarity	NPD7625	Phase 1
0.623	Remote Similarity	NPD6921	Approved
0.6226	Remote Similarity	NPD7637	Suspended
0.6226	Remote Similarity	NPD6079	Approved
0.6218	Remote Similarity	NPD6274	Approved
0.6214	Remote Similarity	NPD7334	Approved
0.6214	Remote Similarity	NPD5330	Approved
0.6214	Remote Similarity	NPD7146	Approved
0.6214	Remote Similarity	NPD6409	Approved
0.6214	Remote Similarity	NPD7521	Approved
0.6214	Remote Similarity	NPD6684	Approved
0.6202	Remote Similarity	NPD8450	Suspended
0.6198	Remote Similarity	NPD7100	Approved
0.6198	Remote Similarity	NPD7101	Approved
0.6195	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6933	Approved
0.6182	Remote Similarity	NPD5696	Approved
0.6167	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5226	Approved
0.6161	Remote Similarity	NPD4633	Approved
0.6161	Remote Similarity	NPD5224	Approved
0.6161	Remote Similarity	NPD5211	Phase 2
0.6161	Remote Similarity	NPD5225	Approved
0.6154	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7750	Discontinued
0.6116	Remote Similarity	NPD7641	Discontinued
0.6116	Remote Similarity	NPD6335	Approved
0.6106	Remote Similarity	NPD5175	Approved
0.6106	Remote Similarity	NPD5174	Approved
0.61	Remote Similarity	NPD6931	Approved
0.61	Remote Similarity	NPD6928	Phase 2
0.61	Remote Similarity	NPD6930	Phase 2
0.6098	Remote Similarity	NPD6908	Approved
0.6098	Remote Similarity	NPD6909	Approved
0.6095	Remote Similarity	NPD6672	Approved
0.6095	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6903	Approved
0.6095	Remote Similarity	NPD5737	Approved
0.608	Remote Similarity	NPD8341	Approved
0.608	Remote Similarity	NPD8340	Approved
0.608	Remote Similarity	NPD8342	Approved
0.608	Remote Similarity	NPD8299	Approved
0.6071	Remote Similarity	NPD5223	Approved
0.6067	Remote Similarity	NPD1145	Discontinued
0.6063	Remote Similarity	NPD8337	Approved
0.6063	Remote Similarity	NPD8336	Approved
0.6055	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5141	Approved
0.6038	Remote Similarity	NPD4753	Phase 2
0.6033	Remote Similarity	NPD6317	Approved
0.6032	Remote Similarity	NPD8451	Approved
0.6019	Remote Similarity	NPD3666	Approved
0.6019	Remote Similarity	NPD3133	Approved
0.6019	Remote Similarity	NPD3665	Phase 1

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