NPASS Compound

Structure

CID229655 OpenBabel06191716022D 23 23 0 0 1 0 0 0 0 0999 V2000 -0.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 -0.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 1.4641 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 -3.2321 0.5981 0.0000 C 0 0 0 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 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 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2321 2.3301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -2.5981 -0.5000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 2 10 1 0 0 0 0 4 16 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 11 9 1 1 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 6 0 0 0 13 14 1 0 0 0 0 13 20 1 1 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 22 1 0 0 0 0 15 23 1 1 0 0 0 16 3 1 1 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.18
Volume:	332.994
LogP:	-0.294
LogD:	-0.086
LogS:	-1.207
# Rotatable Bonds:	8
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	4.429
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.198
MDCK Permeability:	0.00027190084801986814
Pgp-inhibitor:	0.087
Pgp-substrate:	0.05
Human Intestinal Absorption (HIA):	0.821
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.269
Plasma Protein Binding (PPB):	48.769222259521484%
Volume Distribution (VD):	0.504
Pgp-substrate:	55.16969680786133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.423
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.706
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	1.7
Half-life (T1/2):	0.859

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.236
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.82
Carcinogencity:	0.012
Eye Corrosion:	0.013
Eye Irritation:	0.469
Respiratory Toxicity:	0.508

Download Data

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

Natural Product: NPC229655

Natural Product ID:	NPC229655
*Common Name:**	(2S,3R,4S,5S,6R)-2-[(3S,6E)-8-Hydroxy-3,7-Dimethylocta-1,6-Dien-3-Yl]Oxy-6-(Hydroxymethyl)Oxane-3,4,5-Triol
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[(3S,6E)-8-hydroxy-3,7-dimethylocta-1,6-dien-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	NEZCMGYOACDFPH-ZQMBXQQMSA-N
Standard InCHI:	InChI=1S/C16H28O7/c1-4-16(3,7-5-6-10(2)8-17)23-15-14(21)13(20)12(19)11(9-18)22-15/h4,6,11-15,17-21H,1,5,7-9H2,2-3H3/b10-6+/t11-,12-,13+,14-,15+,16-/m1/s1
SMILES:	OC/C(=C/CC[C@](O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)(C=C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469619
PubChem CID:	44559174
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO32690	salsola tetrandra	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989538]
NPO9771	Aka coralliphagum	Species	Niphatidae	Eukaryota	n.a.	San Salvador in the Bahamas (12-26 m depth)	2001-MAR; 2003-JUL	PMID[17309298]
NPO11402	Tithonia rotundifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11166	Sclerodoris tanya	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11758	Parmelia pokornyi	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9771	Aka coralliphagum	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14637	Saussurea cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11402	Tithonia rotundifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2684	Cortinarius vinosipes	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14310	Tecoma heptaphylla	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13119	Hymenoxys microcephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4385	Aconitum zuccarini	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14222	Schefflera divaricata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	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
ED50	1
MIC	5
Others	3

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	ED50	=	21.8	uM	PMID[484591]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	700.0	ug.mL-1	PMID[484591]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	700.0	ug.mL-1	PMID[484591]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	>	700.0	ug ml-1	PMID[484591]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	700.0	ug.mL-1	PMID[484591]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	600.0	ug.mL-1	PMID[484591]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MBC	>	700.0	ug ml-1	PMID[484591]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	700.0	ug.mL-1	PMID[484591]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	>	700.0	ug ml-1	PMID[484591]

☑ 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 NPC229655 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	163
0.1-0.2	2017
0.2-0.3	6203
0.3-0.4	15941
0.4-0.5	10907
0.5-0.6	6098
0.6-0.7	1169
0.7-0.8	168
0.8-0.85	22
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8974	High Similarity	NPC475035
0.8904	High Similarity	NPC472174
0.8649	High Similarity	NPC472173
0.8642	High Similarity	NPC475037
0.8514	High Similarity	NPC132938
0.85	High Similarity	NPC266718
0.8429	Intermediate Similarity	NPC31496
0.8415	Intermediate Similarity	NPC125142
0.8395	Intermediate Similarity	NPC475034
0.8395	Intermediate Similarity	NPC470658
0.8228	Intermediate Similarity	NPC127295
0.8228	Intermediate Similarity	NPC163362
0.8169	Intermediate Similarity	NPC294813
0.8169	Intermediate Similarity	NPC13143
0.8095	Intermediate Similarity	NPC248312
0.8	Intermediate Similarity	NPC474078
0.8	Intermediate Similarity	NPC104129
0.8	Intermediate Similarity	NPC249408
0.8	Intermediate Similarity	NPC477748
0.8	Intermediate Similarity	NPC100697
0.7952	Intermediate Similarity	NPC73166
0.7949	Intermediate Similarity	NPC326661
0.7931	Intermediate Similarity	NPC280390
0.7927	Intermediate Similarity	NPC142111
0.7927	Intermediate Similarity	NPC473315
0.7907	Intermediate Similarity	NPC327253
0.7907	Intermediate Similarity	NPC202886
0.7901	Intermediate Similarity	NPC469469
0.7831	Intermediate Similarity	NPC136699
0.7831	Intermediate Similarity	NPC220167
0.7831	Intermediate Similarity	NPC473308
0.7816	Intermediate Similarity	NPC477749
0.7805	Intermediate Similarity	NPC251026
0.7805	Intermediate Similarity	NPC20072
0.7791	Intermediate Similarity	NPC309310
0.7765	Intermediate Similarity	NPC475186
0.7765	Intermediate Similarity	NPC118077
0.7746	Intermediate Similarity	NPC155457
0.7738	Intermediate Similarity	NPC470124
0.7738	Intermediate Similarity	NPC471494
0.7727	Intermediate Similarity	NPC238090
0.7727	Intermediate Similarity	NPC472195
0.7727	Intermediate Similarity	NPC320552
0.7727	Intermediate Similarity	NPC67398
0.7727	Intermediate Similarity	NPC320089
0.7727	Intermediate Similarity	NPC474792
0.7727	Intermediate Similarity	NPC91654
0.7727	Intermediate Similarity	NPC472196
0.7701	Intermediate Similarity	NPC118078
0.7692	Intermediate Similarity	NPC307517
0.7692	Intermediate Similarity	NPC61630
0.7692	Intermediate Similarity	NPC81483
0.7692	Intermediate Similarity	NPC169468
0.7674	Intermediate Similarity	NPC137368
0.7654	Intermediate Similarity	NPC321728
0.7647	Intermediate Similarity	NPC311163
0.7647	Intermediate Similarity	NPC208473
0.764	Intermediate Similarity	NPC25701
0.764	Intermediate Similarity	NPC159698
0.764	Intermediate Similarity	NPC2003
0.7632	Intermediate Similarity	NPC472947
0.7614	Intermediate Similarity	NPC302584
0.7614	Intermediate Similarity	NPC9447
0.7568	Intermediate Similarity	NPC147292
0.7564	Intermediate Similarity	NPC55652
0.7534	Intermediate Similarity	NPC277570
0.7531	Intermediate Similarity	NPC477089
0.7529	Intermediate Similarity	NPC477747
0.7529	Intermediate Similarity	NPC477746
0.7528	Intermediate Similarity	NPC61201
0.75	Intermediate Similarity	NPC6414
0.75	Intermediate Similarity	NPC303451
0.7471	Intermediate Similarity	NPC470137
0.747	Intermediate Similarity	NPC246621
0.747	Intermediate Similarity	NPC280367
0.7447	Intermediate Similarity	NPC195510
0.7447	Intermediate Similarity	NPC13171
0.7444	Intermediate Similarity	NPC294293
0.7416	Intermediate Similarity	NPC472199
0.7416	Intermediate Similarity	NPC472197
0.7407	Intermediate Similarity	NPC110813
0.7391	Intermediate Similarity	NPC309503
0.7391	Intermediate Similarity	NPC96597
0.7391	Intermediate Similarity	NPC125551
0.7391	Intermediate Similarity	NPC239547
0.7391	Intermediate Similarity	NPC91197
0.7391	Intermediate Similarity	NPC155319
0.7391	Intermediate Similarity	NPC474194
0.7386	Intermediate Similarity	NPC285588
0.7363	Intermediate Similarity	NPC170204
0.7349	Intermediate Similarity	NPC190008
0.734	Intermediate Similarity	NPC154127
0.7326	Intermediate Similarity	NPC34581
0.7317	Intermediate Similarity	NPC133377
0.7317	Intermediate Similarity	NPC4436
0.7312	Intermediate Similarity	NPC40182
0.7312	Intermediate Similarity	NPC198422
0.7312	Intermediate Similarity	NPC312325
0.7294	Intermediate Similarity	NPC263087
0.7294	Intermediate Similarity	NPC2379
0.7294	Intermediate Similarity	NPC27314
0.7294	Intermediate Similarity	NPC31019
0.7294	Intermediate Similarity	NPC106912
0.7284	Intermediate Similarity	NPC256720
0.7284	Intermediate Similarity	NPC236228
0.7283	Intermediate Similarity	NPC54731
0.7283	Intermediate Similarity	NPC306041
0.7283	Intermediate Similarity	NPC90583
0.726	Intermediate Similarity	NPC258788
0.7253	Intermediate Similarity	NPC472198
0.7241	Intermediate Similarity	NPC472379
0.7241	Intermediate Similarity	NPC470836
0.7234	Intermediate Similarity	NPC255677
0.7234	Intermediate Similarity	NPC306344
0.7234	Intermediate Similarity	NPC22149
0.7222	Intermediate Similarity	NPC110072
0.7204	Intermediate Similarity	NPC240372
0.7204	Intermediate Similarity	NPC472290
0.7191	Intermediate Similarity	NPC299527
0.7174	Intermediate Similarity	NPC469543
0.7162	Intermediate Similarity	NPC55376
0.7159	Intermediate Similarity	NPC471056
0.7159	Intermediate Similarity	NPC471055
0.7158	Intermediate Similarity	NPC298255
0.7158	Intermediate Similarity	NPC20673
0.7158	Intermediate Similarity	NPC285231
0.7158	Intermediate Similarity	NPC280991
0.7158	Intermediate Similarity	NPC198992
0.7158	Intermediate Similarity	NPC21568
0.7158	Intermediate Similarity	NPC28304
0.7143	Intermediate Similarity	NPC254538
0.7143	Intermediate Similarity	NPC474285
0.7143	Intermediate Similarity	NPC474835
0.7113	Intermediate Similarity	NPC86095
0.7111	Intermediate Similarity	NPC117596
0.7111	Intermediate Similarity	NPC473311
0.7108	Intermediate Similarity	NPC13823
0.7108	Intermediate Similarity	NPC68119
0.7108	Intermediate Similarity	NPC248775
0.7105	Intermediate Similarity	NPC476586
0.7093	Intermediate Similarity	NPC44261
0.7093	Intermediate Similarity	NPC231601
0.7083	Intermediate Similarity	NPC201191
0.7079	Intermediate Similarity	NPC471755
0.7079	Intermediate Similarity	NPC471756
0.7067	Intermediate Similarity	NPC476584
0.7065	Intermediate Similarity	NPC35269
0.7065	Intermediate Similarity	NPC70323
0.7065	Intermediate Similarity	NPC192066
0.7065	Intermediate Similarity	NPC17290
0.7065	Intermediate Similarity	NPC262312
0.7065	Intermediate Similarity	NPC3568
0.7065	Intermediate Similarity	NPC256368
0.7065	Intermediate Similarity	NPC256570
0.7065	Intermediate Similarity	NPC23454
0.7059	Intermediate Similarity	NPC16090
0.7059	Intermediate Similarity	NPC236649
0.7059	Intermediate Similarity	NPC21693
0.7053	Intermediate Similarity	NPC324667
0.7053	Intermediate Similarity	NPC244878
0.7053	Intermediate Similarity	NPC130792
0.7041	Intermediate Similarity	NPC239961
0.7037	Intermediate Similarity	NPC474280
0.7033	Intermediate Similarity	NPC472125
0.7033	Intermediate Similarity	NPC472126
0.7033	Intermediate Similarity	NPC469410
0.7033	Intermediate Similarity	NPC472124
0.7027	Intermediate Similarity	NPC469694
0.7024	Intermediate Similarity	NPC470149
0.7024	Intermediate Similarity	NPC476701
0.7024	Intermediate Similarity	NPC470148
0.7024	Intermediate Similarity	NPC180725
0.7024	Intermediate Similarity	NPC86971
0.7011	Intermediate Similarity	NPC78673
0.7011	Intermediate Similarity	NPC166279
0.7011	Intermediate Similarity	NPC160517
0.7011	Intermediate Similarity	NPC186155
0.701	Intermediate Similarity	NPC118761
0.701	Intermediate Similarity	NPC151516
0.701	Intermediate Similarity	NPC197541
0.701	Intermediate Similarity	NPC284929
0.701	Intermediate Similarity	NPC267869
0.701	Intermediate Similarity	NPC234304
0.7	Intermediate Similarity	NPC477086
0.7	Intermediate Similarity	NPC477087
0.6989	Remote Similarity	NPC101051
0.6988	Remote Similarity	NPC475711
0.6988	Remote Similarity	NPC474026
0.6988	Remote Similarity	NPC474278
0.6988	Remote Similarity	NPC476703
0.6979	Remote Similarity	NPC154132
0.6979	Remote Similarity	NPC475157
0.6979	Remote Similarity	NPC57586
0.6979	Remote Similarity	NPC475655
0.6979	Remote Similarity	NPC471637
0.6979	Remote Similarity	NPC2313
0.6977	Remote Similarity	NPC477390
0.6977	Remote Similarity	NPC477385
0.697	Remote Similarity	NPC33053
0.6966	Remote Similarity	NPC316138

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 NPC229655 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	2307
0.2-0.3	4050
0.3-0.4	1983
0.4-0.5	490
0.5-0.6	141
0.6-0.7	30
0.7-0.8	0
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
0.6947	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6698	Approved
0.6739	Remote Similarity	NPD46	Approved
0.6569	Remote Similarity	NPD6686	Approved
0.6559	Remote Similarity	NPD7838	Discovery
0.6538	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD905	Approved
0.6479	Remote Similarity	NPD904	Phase 3
0.6465	Remote Similarity	NPD5344	Discontinued
0.6444	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2269	Approved
0.6316	Remote Similarity	NPD7983	Approved
0.631	Remote Similarity	NPD4732	Discontinued
0.6306	Remote Similarity	NPD8517	Approved
0.6306	Remote Similarity	NPD8513	Phase 3
0.6306	Remote Similarity	NPD8515	Approved
0.6306	Remote Similarity	NPD8516	Approved
0.6301	Remote Similarity	NPD888	Phase 3
0.6301	Remote Similarity	NPD891	Phase 3
0.6301	Remote Similarity	NPD894	Approved
0.6301	Remote Similarity	NPD892	Phase 3
0.6301	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD895	Approved
0.6301	Remote Similarity	NPD887	Approved
0.6301	Remote Similarity	NPD889	Approved
0.6301	Remote Similarity	NPD893	Approved
0.6282	Remote Similarity	NPD368	Approved
0.6182	Remote Similarity	NPD7327	Approved
0.6182	Remote Similarity	NPD7328	Approved
0.6161	Remote Similarity	NPD7503	Approved
0.6154	Remote Similarity	NPD6110	Phase 1
0.6126	Remote Similarity	NPD7516	Approved
0.6071	Remote Similarity	NPD8294	Approved
0.6071	Remote Similarity	NPD8377	Approved
0.6064	Remote Similarity	NPD7524	Approved
0.6053	Remote Similarity	NPD2267	Suspended
0.604	Remote Similarity	NPD6648	Approved
0.6018	Remote Similarity	NPD8296	Approved
0.6018	Remote Similarity	NPD8380	Approved
0.6018	Remote Similarity	NPD8335	Approved
0.6018	Remote Similarity	NPD8379	Approved
0.6018	Remote Similarity	NPD8378	Approved
0.6018	Remote Similarity	NPD8033	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD8997	Approved
0.6	Remote Similarity	NPD8998	Phase 2
0.6	Remote Similarity	NPD8993	Phase 1
0.6	Remote Similarity	NPD9000	Phase 3
0.6	Remote Similarity	NPD8999	Phase 3
0.5957	Remote Similarity	NPD4249	Approved
0.5949	Remote Similarity	NPD6123	Approved
0.5914	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.59	Remote Similarity	NPD7839	Suspended
0.5895	Remote Similarity	NPD4250	Approved
0.5895	Remote Similarity	NPD4251	Approved
0.5877	Remote Similarity	NPD8444	Approved
0.5876	Remote Similarity	NPD3168	Discontinued
0.5872	Remote Similarity	NPD6429	Approved
0.5872	Remote Similarity	NPD6430	Approved
0.5854	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8966	Approved
0.5833	Remote Similarity	NPD8965	Approved
0.5824	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD7514	Phase 3
0.5824	Remote Similarity	NPD7332	Phase 2
0.5812	Remote Similarity	NPD7507	Approved
0.5812	Remote Similarity	NPD8451	Approved
0.5806	Remote Similarity	NPD6695	Phase 3
0.5776	Remote Similarity	NPD7829	Approved
0.5776	Remote Similarity	NPD7830	Approved
0.5776	Remote Similarity	NPD7642	Approved
0.5775	Remote Similarity	NPD4265	Approved
0.5763	Remote Similarity	NPD8074	Phase 3
0.5763	Remote Similarity	NPD8448	Approved
0.5726	Remote Similarity	NPD8341	Approved
0.5726	Remote Similarity	NPD8299	Approved
0.5726	Remote Similarity	NPD8340	Approved
0.5726	Remote Similarity	NPD8342	Approved
0.5726	Remote Similarity	NPD1091	Approved
0.5714	Remote Similarity	NPD342	Phase 1
0.5714	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.569	Remote Similarity	NPD5125	Phase 3
0.569	Remote Similarity	NPD5126	Approved
0.5688	Remote Similarity	NPD6371	Approved
0.5676	Remote Similarity	NPD8133	Approved
0.5676	Remote Similarity	NPD3731	Phase 3
0.5667	Remote Similarity	NPD7319	Approved
0.5657	Remote Similarity	NPD7637	Suspended
0.5652	Remote Similarity	NPD4819	Approved
0.5652	Remote Similarity	NPD4822	Approved
0.5652	Remote Similarity	NPD4821	Approved
0.5652	Remote Similarity	NPD4820	Approved
0.5638	Remote Similarity	NPD7154	Phase 3
0.5631	Remote Similarity	NPD4225	Approved
0.562	Remote Similarity	NPD8392	Approved
0.562	Remote Similarity	NPD8390	Approved
0.562	Remote Similarity	NPD8391	Approved
0.5614	Remote Similarity	NPD7641	Discontinued
0.561	Remote Similarity	NPD847	Phase 1
0.5604	Remote Similarity	NPD7145	Approved
0.5604	Remote Similarity	NPD4268	Approved
0.5604	Remote Similarity	NPD4271	Approved
0.56	Remote Similarity	NPD5778	Approved
0.56	Remote Similarity	NPD5779	Approved

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