NPASS Compound

Structure

CID29697 OpenBabel06191715352D 24 23 0 0 1 0 0 0 0 0999 V2000 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -2.5981 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 -2.5981 2.5000 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 3.4641 1.0000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 -5.1962 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 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 15 2 0 0 0 0 11 12 1 0 0 0 0 11 14 3 0 0 0 0 12 16 3 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 20 1 0 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 22 1 1 0 0 0 20 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	373.818
LogP:	3.829
LogD:	3.455
LogS:	-3.843
# Rotatable Bonds:	12
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.264
Synthetic Accessibility Score:	3.897
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.696
MDCK Permeability:	4.163885023444891e-05
Pgp-inhibitor:	0.043
Pgp-substrate:	0.124
Human Intestinal Absorption (HIA):	0.501
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.748
Plasma Protein Binding (PPB):	99.37753295898438%
Volume Distribution (VD):	1.391
Pgp-substrate:	2.395280361175537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.485
CYP1A2-substrate:	0.249
CYP2C19-inhibitor:	0.884
CYP2C19-substrate:	0.246
CYP2C9-inhibitor:	0.841
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.831
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	7.35
Half-life (T1/2):	0.824

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.631
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.918
Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.954
Carcinogencity:	0.199
Eye Corrosion:	0.917
Eye Irritation:	0.923
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC29697

Natural Product ID:	NPC29697
*Common Name:**	Oplopandiol Acetate
IUPAC Name:	[(Z,11S,16S)-11,16-dihydroxyoctadec-9-en-12,14-diynyl] acetate
Synonyms:	Oplopandiol Acetate
Standard InCHIKey:	SBFJUILRJBSVAL-HAGSVXFXSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-3-19(22)14-11-12-16-20(23)15-10-8-6-4-5-7-9-13-17-24-18(2)21/h10,15,19-20,22-23H,3-9,13,17H2,1-2H3/b15-10-/t19-,20-/m0/s1
SMILES:	CC[C@@H](C#CC#C[C@H](/C=CCCCCCCCCOC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463808
PubChem CID:	6474835
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain fatty alcohols

*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
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO25695	Oplopanax horridus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20218656]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO25695	Oplopanax horridus	Species	Araliaceae	Eukaryota	Tubers	n.a.	n.a.	PMID[23356207]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO25695	Oplopanax horridus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO25695	Oplopanax horridus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392889]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25663	Piscidia piscipula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23679	Streptomyces roseiscleroticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25695	Oplopanax horridus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24374	Brunsvigia orientalis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23922	Helichrysum oxyphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25131	Parmelia weberi	Species	Parmeliaceae	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
MIC	8
Others	1

Activity Type	# Activity
Individual Protein	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[481319]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[481319]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50.0	ug.mL-1	PMID[481319]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[481319]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[481319]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50.0	ug.mL-1	PMID[481319]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	FC	=	4.2	n.a.	PMID[481320]

☑ 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 NPC29697 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	151
0.1-0.2	2265
0.2-0.3	11523
0.3-0.4	16322
0.4-0.5	7918
0.5-0.6	3379
0.6-0.7	842
0.7-0.8	235
0.8-0.85	42
0.85-0.9	12
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC325929
0.9828	High Similarity	NPC66460
0.9828	High Similarity	NPC271282
0.9167	High Similarity	NPC475984
0.9016	High Similarity	NPC470965
0.8833	High Similarity	NPC474267
0.8621	High Similarity	NPC49059
0.8621	High Similarity	NPC256209
0.8571	High Similarity	NPC470320
0.8571	High Similarity	NPC226592
0.85	High Similarity	NPC212730
0.85	High Similarity	NPC44542
0.85	High Similarity	NPC265551
0.85	High Similarity	NPC472445
0.8387	Intermediate Similarity	NPC471278
0.8361	Intermediate Similarity	NPC469373
0.8226	Intermediate Similarity	NPC222852
0.8209	Intermediate Similarity	NPC470436
0.8197	Intermediate Similarity	NPC48968
0.8197	Intermediate Similarity	NPC594
0.8197	Intermediate Similarity	NPC470970
0.8167	Intermediate Similarity	NPC474513
0.8167	Intermediate Similarity	NPC477726
0.8167	Intermediate Similarity	NPC477725
0.8167	Intermediate Similarity	NPC146551
0.8167	Intermediate Similarity	NPC470963
0.8103	Intermediate Similarity	NPC129263
0.8103	Intermediate Similarity	NPC151782
0.8095	Intermediate Similarity	NPC299730
0.8033	Intermediate Similarity	NPC470964
0.8033	Intermediate Similarity	NPC470968
0.8033	Intermediate Similarity	NPC311648
0.8033	Intermediate Similarity	NPC471960
0.8033	Intermediate Similarity	NPC477661
0.8033	Intermediate Similarity	NPC470969
0.8033	Intermediate Similarity	NPC473847
0.8033	Intermediate Similarity	NPC475384
0.8033	Intermediate Similarity	NPC470966
0.8033	Intermediate Similarity	NPC161838
0.8033	Intermediate Similarity	NPC470967
0.8	Intermediate Similarity	NPC110732
0.7969	Intermediate Similarity	NPC113293
0.7969	Intermediate Similarity	NPC477829
0.7969	Intermediate Similarity	NPC26810
0.7931	Intermediate Similarity	NPC72699
0.791	Intermediate Similarity	NPC26500
0.791	Intermediate Similarity	NPC99619
0.7903	Intermediate Similarity	NPC471277
0.7903	Intermediate Similarity	NPC193975
0.7903	Intermediate Similarity	NPC471279
0.7879	Intermediate Similarity	NPC136164
0.7879	Intermediate Similarity	NPC245947
0.7879	Intermediate Similarity	NPC255863
0.7869	Intermediate Similarity	NPC473725
0.7869	Intermediate Similarity	NPC475353
0.7869	Intermediate Similarity	NPC473910
0.7869	Intermediate Similarity	NPC152668
0.7869	Intermediate Similarity	NPC473721
0.7869	Intermediate Similarity	NPC52264
0.7869	Intermediate Similarity	NPC473896
0.7869	Intermediate Similarity	NPC473735
0.7857	Intermediate Similarity	NPC470435
0.7857	Intermediate Similarity	NPC329890
0.7833	Intermediate Similarity	NPC34577
0.7826	Intermediate Similarity	NPC4299
0.7812	Intermediate Similarity	NPC327112
0.7759	Intermediate Similarity	NPC153538
0.7759	Intermediate Similarity	NPC248884
0.7759	Intermediate Similarity	NPC207815
0.7759	Intermediate Similarity	NPC85079
0.7759	Intermediate Similarity	NPC31194
0.7705	Intermediate Similarity	NPC473532
0.7705	Intermediate Similarity	NPC137538
0.7692	Intermediate Similarity	NPC328776
0.7692	Intermediate Similarity	NPC321838
0.7692	Intermediate Similarity	NPC320305
0.7692	Intermediate Similarity	NPC201939
0.7681	Intermediate Similarity	NPC143396
0.7681	Intermediate Similarity	NPC101622
0.7667	Intermediate Similarity	NPC142092
0.7647	Intermediate Similarity	NPC22101
0.7647	Intermediate Similarity	NPC330426
0.7647	Intermediate Similarity	NPC473752
0.7647	Intermediate Similarity	NPC148192
0.7647	Intermediate Similarity	NPC127091
0.7647	Intermediate Similarity	NPC104537
0.7647	Intermediate Similarity	NPC271921
0.7647	Intermediate Similarity	NPC25298
0.7612	Intermediate Similarity	NPC326268
0.7612	Intermediate Similarity	NPC318420
0.7606	Intermediate Similarity	NPC329914
0.7606	Intermediate Similarity	NPC477085
0.7606	Intermediate Similarity	NPC327383
0.7606	Intermediate Similarity	NPC185186
0.7581	Intermediate Similarity	NPC474913
0.7571	Intermediate Similarity	NPC476037
0.7541	Intermediate Similarity	NPC477724
0.7541	Intermediate Similarity	NPC187361
0.7541	Intermediate Similarity	NPC26102
0.7538	Intermediate Similarity	NPC328311
0.7538	Intermediate Similarity	NPC243532
0.7536	Intermediate Similarity	NPC473559
0.7536	Intermediate Similarity	NPC141481
0.7536	Intermediate Similarity	NPC324981
0.7536	Intermediate Similarity	NPC48218
0.7534	Intermediate Similarity	NPC188860
0.75	Intermediate Similarity	NPC93639
0.75	Intermediate Similarity	NPC71053
0.75	Intermediate Similarity	NPC55383
0.75	Intermediate Similarity	NPC59408
0.75	Intermediate Similarity	NPC146811
0.7465	Intermediate Similarity	NPC477086
0.7465	Intermediate Similarity	NPC477087
0.7463	Intermediate Similarity	NPC68343
0.7463	Intermediate Similarity	NPC328089
0.746	Intermediate Similarity	NPC472808
0.746	Intermediate Similarity	NPC179764
0.746	Intermediate Similarity	NPC187777
0.746	Intermediate Similarity	NPC324224
0.7458	Intermediate Similarity	NPC471280
0.7458	Intermediate Similarity	NPC471275
0.7458	Intermediate Similarity	NPC471276
0.7458	Intermediate Similarity	NPC125122
0.7432	Intermediate Similarity	NPC233071
0.7429	Intermediate Similarity	NPC236208
0.7429	Intermediate Similarity	NPC130618
0.7429	Intermediate Similarity	NPC475004
0.7424	Intermediate Similarity	NPC55376
0.7419	Intermediate Similarity	NPC269615
0.7419	Intermediate Similarity	NPC48058
0.7414	Intermediate Similarity	NPC35141
0.7414	Intermediate Similarity	NPC55063
0.7414	Intermediate Similarity	NPC19834
0.7414	Intermediate Similarity	NPC124183
0.7397	Intermediate Similarity	NPC260396
0.7397	Intermediate Similarity	NPC327041
0.7397	Intermediate Similarity	NPC285840
0.7391	Intermediate Similarity	NPC473829
0.7391	Intermediate Similarity	NPC478097
0.7391	Intermediate Similarity	NPC475443
0.7385	Intermediate Similarity	NPC318306
0.7353	Intermediate Similarity	NPC476655
0.7353	Intermediate Similarity	NPC478098
0.7353	Intermediate Similarity	NPC478099
0.7353	Intermediate Similarity	NPC476654
0.7353	Intermediate Similarity	NPC19769
0.7353	Intermediate Similarity	NPC96414
0.7353	Intermediate Similarity	NPC476657
0.7344	Intermediate Similarity	NPC474577
0.7333	Intermediate Similarity	NPC473913
0.7333	Intermediate Similarity	NPC328784
0.7333	Intermediate Similarity	NPC477727
0.7333	Intermediate Similarity	NPC199286
0.7333	Intermediate Similarity	NPC248775
0.7333	Intermediate Similarity	NPC474642
0.7333	Intermediate Similarity	NPC471281
0.7333	Intermediate Similarity	NPC249670
0.7333	Intermediate Similarity	NPC291437
0.7324	Intermediate Similarity	NPC476660
0.7324	Intermediate Similarity	NPC476012
0.7324	Intermediate Similarity	NPC42526
0.7302	Intermediate Similarity	NPC473863
0.7302	Intermediate Similarity	NPC274290
0.7302	Intermediate Similarity	NPC471239
0.7302	Intermediate Similarity	NPC317899
0.7302	Intermediate Similarity	NPC54766
0.7286	Intermediate Similarity	NPC474823
0.7273	Intermediate Similarity	NPC81896
0.7273	Intermediate Similarity	NPC321919
0.726	Intermediate Similarity	NPC227396
0.7258	Intermediate Similarity	NPC474496
0.7246	Intermediate Similarity	NPC476659
0.7246	Intermediate Similarity	NPC476656
0.7246	Intermediate Similarity	NPC201356
0.7241	Intermediate Similarity	NPC269074
0.7237	Intermediate Similarity	NPC470148
0.7237	Intermediate Similarity	NPC55304
0.7237	Intermediate Similarity	NPC180725
0.7237	Intermediate Similarity	NPC1180
0.7237	Intermediate Similarity	NPC226226
0.7237	Intermediate Similarity	NPC470149
0.7222	Intermediate Similarity	NPC472254
0.7213	Intermediate Similarity	NPC294278
0.7213	Intermediate Similarity	NPC474495
0.7213	Intermediate Similarity	NPC170776
0.7213	Intermediate Similarity	NPC9273
0.7213	Intermediate Similarity	NPC76198
0.7213	Intermediate Similarity	NPC165447
0.7213	Intermediate Similarity	NPC197272
0.7213	Intermediate Similarity	NPC475477
0.7213	Intermediate Similarity	NPC471959
0.7213	Intermediate Similarity	NPC329608
0.7213	Intermediate Similarity	NPC89824
0.7213	Intermediate Similarity	NPC473672
0.7213	Intermediate Similarity	NPC256656
0.7213	Intermediate Similarity	NPC224148
0.7213	Intermediate Similarity	NPC477723
0.7206	Intermediate Similarity	NPC476658
0.72	Intermediate Similarity	NPC474026
0.72	Intermediate Similarity	NPC40049

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 NPC29697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	122
0.1-0.2	2849
0.2-0.3	3899
0.3-0.4	1777
0.4-0.5	378
0.5-0.6	77
0.6-0.7	44
0.7-0.8	4
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
0.7812	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3197	Phase 1
0.7143	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5331	Approved
0.7089	Intermediate Similarity	NPD5332	Approved
0.6984	Remote Similarity	NPD3172	Approved
0.6914	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4268	Approved
0.6883	Remote Similarity	NPD4271	Approved
0.6875	Remote Similarity	NPD7154	Phase 3
0.6875	Remote Similarity	NPD4266	Approved
0.6875	Remote Similarity	NPD3195	Phase 2
0.6875	Remote Similarity	NPD3196	Approved
0.6875	Remote Similarity	NPD3194	Approved
0.6716	Remote Similarity	NPD6109	Phase 1
0.6709	Remote Similarity	NPD4820	Approved
0.6709	Remote Similarity	NPD4821	Approved
0.6709	Remote Similarity	NPD4822	Approved
0.6709	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4249	Approved
0.662	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD3173	Approved
0.6548	Remote Similarity	NPD4251	Approved
0.6548	Remote Similarity	NPD4250	Approved
0.6543	Remote Similarity	NPD4269	Approved
0.6543	Remote Similarity	NPD4270	Approved
0.65	Remote Similarity	NPD4252	Approved
0.6452	Remote Similarity	NPD5343	Approved
0.6429	Remote Similarity	NPD5786	Approved
0.642	Remote Similarity	NPD4790	Discontinued
0.6406	Remote Similarity	NPD28	Approved
0.6406	Remote Similarity	NPD29	Approved
0.6393	Remote Similarity	NPD4265	Approved
0.6393	Remote Similarity	NPD39	Approved
0.6393	Remote Similarity	NPD4222	Approved
0.6341	Remote Similarity	NPD6435	Approved
0.6329	Remote Similarity	NPD4756	Discovery
0.631	Remote Similarity	NPD5363	Approved
0.625	Remote Similarity	NPD7983	Approved
0.6232	Remote Similarity	NPD585	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6096	Approved
0.623	Remote Similarity	NPD6097	Approved
0.622	Remote Similarity	NPD5369	Approved
0.6207	Remote Similarity	NPD5370	Suspended
0.619	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.619	Remote Similarity	NPD622	Approved
0.618	Remote Similarity	NPD5778	Approved
0.618	Remote Similarity	NPD5779	Approved
0.6154	Remote Similarity	NPD6927	Phase 3
0.6136	Remote Similarity	NPD5785	Approved
0.6136	Remote Similarity	NPD7838	Discovery
0.6129	Remote Similarity	NPD3174	Discontinued
0.6111	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD5368	Approved
0.6094	Remote Similarity	NPD4220	Pre-registration
0.6067	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7637	Suspended
0.6066	Remote Similarity	NPD5326	Phase 3
0.6029	Remote Similarity	NPD342	Phase 1
0.5978	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD7839	Suspended
0.5972	Remote Similarity	NPD368	Approved
0.5955	Remote Similarity	NPD46	Approved
0.5955	Remote Similarity	NPD6698	Approved
0.5882	Remote Similarity	NPD3730	Approved
0.5882	Remote Similarity	NPD3728	Approved
0.5875	Remote Similarity	NPD8039	Approved
0.5851	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6051	Approved
0.5843	Remote Similarity	NPD6101	Approved
0.5811	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD7750	Discontinued
0.5769	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD5209	Approved
0.5753	Remote Similarity	NPD4193	Approved
0.5753	Remote Similarity	NPD4191	Approved
0.5753	Remote Similarity	NPD4194	Approved
0.5753	Remote Similarity	NPD4192	Approved
0.5729	Remote Similarity	NPD5344	Discontinued
0.5714	Remote Similarity	NPD6411	Approved
0.5684	Remote Similarity	NPD4225	Approved
0.5679	Remote Similarity	NPD8264	Approved
0.5663	Remote Similarity	NPD3732	Approved
0.5658	Remote Similarity	NPD3704	Approved
0.5625	Remote Similarity	NPD4732	Discontinued
0.5625	Remote Similarity	NPD7640	Approved
0.5625	Remote Similarity	NPD7639	Approved
0.5612	Remote Similarity	NPD6647	Phase 2
0.5604	Remote Similarity	NPD8522	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