NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.2
Volume:	262.957
LogP:	5.511
LogD:	3.854
LogS:	-3.957
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.706
Synthetic Accessibility Score:	3.673
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.384
MDCK Permeability:	1.6821119061205536e-05
Pgp-inhibitor:	0.763
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.876
30% Bioavailability (F30%):	0.159

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.392
Plasma Protein Binding (PPB):	93.52823638916016%
Volume Distribution (VD):	2.361
Pgp-substrate:	5.359309196472168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.577
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.301
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.161
CYP2C9-substrate:	0.526
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.173
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	17.417
Half-life (T1/2):	0.129

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.839
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.066
Skin Sensitization:	0.929
Carcinogencity:	0.563
Eye Corrosion:	0.52
Eye Irritation:	0.953
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC306195

Natural Product ID:	NPC306195
*Common Name:**	Bisabolol
IUPAC Name:	(2S)-6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol
Synonyms:
Standard InCHIKey:	RGZSQWQPBWRIAQ-LOACHALJSA-N
Standard InCHI:	InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14?,15-/m0/s1
SMILES:	CC(=CCC[C@@](C)(C1CC=C(C)CC1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1561544
PubChem CID:	6097621
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17125224]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21875098]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24868863]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25089845]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	Buds	n.a.	n.a.	PMID[25927817]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[27400231]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28682072]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29883114]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO355	Peperomia sui	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO355	Peperomia sui	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9546	Cinamomum cassia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21410	Populus balsamifera	Species	Salicaceae	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
Potency	7

Activity Type	# Activity
Individual Protein	5
Organism	1
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	5011.9	nM	PMID[456111]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	39810.7	nM	PMID[456111]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[456111]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	12589.3	nM	PMID[456111]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	562.3	nM	PMID[456111]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	601.2	nM	PMID[456111]

☑ 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 NPC306195 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	144
0.1-0.2	2600
0.2-0.3	16821
0.3-0.4	12618
0.4-0.5	7203
0.5-0.6	2715
0.6-0.7	488
0.7-0.8	89
0.8-0.85	8
0.85-0.9	0
0.9-0.95	4
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC181255
1.0	High Similarity	NPC35519
1.0	High Similarity	NPC157781
1.0	High Similarity	NPC179169
0.9792	High Similarity	NPC26906
0.9792	High Similarity	NPC214584
0.92	High Similarity	NPC71506
0.92	High Similarity	NPC177112
0.88	High Similarity	NPC329773
0.8421	Intermediate Similarity	NPC79576
0.8421	Intermediate Similarity	NPC194208
0.8421	Intermediate Similarity	NPC282694
0.84	Intermediate Similarity	NPC100445
0.8276	Intermediate Similarity	NPC174956
0.8246	Intermediate Similarity	NPC135648
0.8246	Intermediate Similarity	NPC66020
0.8182	Intermediate Similarity	NPC179024
0.8113	Intermediate Similarity	NPC294358
0.8113	Intermediate Similarity	NPC40417
0.8103	Intermediate Similarity	NPC207007
0.8103	Intermediate Similarity	NPC321867
0.8103	Intermediate Similarity	NPC68679
0.8036	Intermediate Similarity	NPC278550
0.8	Intermediate Similarity	NPC471200
0.7931	Intermediate Similarity	NPC240506
0.7917	Intermediate Similarity	NPC188596
0.7869	Intermediate Similarity	NPC279434
0.7857	Intermediate Similarity	NPC39068
0.7857	Intermediate Similarity	NPC274396
0.7857	Intermediate Similarity	NPC141699
0.7778	Intermediate Similarity	NPC68014
0.7759	Intermediate Similarity	NPC5698
0.7759	Intermediate Similarity	NPC469321
0.7719	Intermediate Similarity	NPC165808
0.7679	Intermediate Similarity	NPC130209
0.7679	Intermediate Similarity	NPC218525
0.7679	Intermediate Similarity	NPC148216
0.7679	Intermediate Similarity	NPC232247
0.7679	Intermediate Similarity	NPC148163
0.7679	Intermediate Similarity	NPC251666
0.7667	Intermediate Similarity	NPC81615
0.7647	Intermediate Similarity	NPC210560
0.7647	Intermediate Similarity	NPC165651
0.7647	Intermediate Similarity	NPC24824
0.7636	Intermediate Similarity	NPC192962
0.7627	Intermediate Similarity	NPC252809
0.7627	Intermediate Similarity	NPC323153
0.76	Intermediate Similarity	NPC15162
0.7593	Intermediate Similarity	NPC244038
0.7581	Intermediate Similarity	NPC267027
0.7581	Intermediate Similarity	NPC202017
0.7581	Intermediate Similarity	NPC326310
0.7544	Intermediate Similarity	NPC264779
0.7541	Intermediate Similarity	NPC290367
0.75	Intermediate Similarity	NPC475251
0.75	Intermediate Similarity	NPC63111
0.75	Intermediate Similarity	NPC210346
0.746	Intermediate Similarity	NPC114651
0.7458	Intermediate Similarity	NPC475931
0.7385	Intermediate Similarity	NPC475728
0.7377	Intermediate Similarity	NPC474480
0.7344	Intermediate Similarity	NPC208999
0.7344	Intermediate Similarity	NPC96484
0.7344	Intermediate Similarity	NPC94192
0.7308	Intermediate Similarity	NPC87439
0.7302	Intermediate Similarity	NPC222366
0.7302	Intermediate Similarity	NPC286669
0.7302	Intermediate Similarity	NPC476039
0.7292	Intermediate Similarity	NPC297643
0.7292	Intermediate Similarity	NPC229262
0.7292	Intermediate Similarity	NPC139717
0.7288	Intermediate Similarity	NPC189290
0.7288	Intermediate Similarity	NPC474769
0.7288	Intermediate Similarity	NPC155025
0.7273	Intermediate Similarity	NPC23954
0.7273	Intermediate Similarity	NPC164022
0.7273	Intermediate Similarity	NPC242992
0.7258	Intermediate Similarity	NPC107540
0.7258	Intermediate Similarity	NPC300593
0.7258	Intermediate Similarity	NPC225415
0.7258	Intermediate Similarity	NPC96793
0.7258	Intermediate Similarity	NPC323424
0.7241	Intermediate Similarity	NPC48891
0.7231	Intermediate Similarity	NPC471560
0.7231	Intermediate Similarity	NPC473893
0.7231	Intermediate Similarity	NPC474248
0.7231	Intermediate Similarity	NPC476431
0.7213	Intermediate Similarity	NPC225342
0.7213	Intermediate Similarity	NPC469728
0.7213	Intermediate Similarity	NPC274704
0.7188	Intermediate Similarity	NPC82337
0.7188	Intermediate Similarity	NPC171225
0.7188	Intermediate Similarity	NPC197805
0.7167	Intermediate Similarity	NPC122239
0.7164	Intermediate Similarity	NPC265485
0.7164	Intermediate Similarity	NPC220939
0.7143	Intermediate Similarity	NPC163678
0.7143	Intermediate Similarity	NPC205618
0.7143	Intermediate Similarity	NPC469326
0.7143	Intermediate Similarity	NPC261782
0.7121	Intermediate Similarity	NPC92801
0.7121	Intermediate Similarity	NPC34834
0.7115	Intermediate Similarity	NPC202189
0.7115	Intermediate Similarity	NPC248411
0.7097	Intermediate Similarity	NPC279200
0.7097	Intermediate Similarity	NPC474155
0.7097	Intermediate Similarity	NPC473759
0.7097	Intermediate Similarity	NPC473508
0.7091	Intermediate Similarity	NPC131623
0.7083	Intermediate Similarity	NPC76145
0.7083	Intermediate Similarity	NPC34764
0.7083	Intermediate Similarity	NPC190810
0.7077	Intermediate Similarity	NPC216460
0.7069	Intermediate Similarity	NPC223604
0.7069	Intermediate Similarity	NPC67508
0.7069	Intermediate Similarity	NPC84824
0.7069	Intermediate Similarity	NPC281590
0.7069	Intermediate Similarity	NPC227135
0.7059	Intermediate Similarity	NPC209279
0.7059	Intermediate Similarity	NPC194586
0.7059	Intermediate Similarity	NPC68889
0.7059	Intermediate Similarity	NPC180871
0.7059	Intermediate Similarity	NPC177470
0.7059	Intermediate Similarity	NPC108494
0.7059	Intermediate Similarity	NPC88079
0.7059	Intermediate Similarity	NPC67761
0.7059	Intermediate Similarity	NPC51758
0.7049	Intermediate Similarity	NPC99487
0.7049	Intermediate Similarity	NPC176621
0.7031	Intermediate Similarity	NPC250977
0.7031	Intermediate Similarity	NPC197089
0.7018	Intermediate Similarity	NPC268564
0.7015	Intermediate Similarity	NPC167706
0.7	Intermediate Similarity	NPC475830
0.7	Intermediate Similarity	NPC10017
0.7	Intermediate Similarity	NPC181872
0.6984	Remote Similarity	NPC234767
0.6984	Remote Similarity	NPC309300
0.6981	Remote Similarity	NPC296337
0.697	Remote Similarity	NPC469914
0.6935	Remote Similarity	NPC41160
0.6923	Remote Similarity	NPC472255
0.6923	Remote Similarity	NPC136813
0.6923	Remote Similarity	NPC269862
0.6923	Remote Similarity	NPC472253
0.6912	Remote Similarity	NPC130665
0.6912	Remote Similarity	NPC474140
0.6912	Remote Similarity	NPC471799
0.6912	Remote Similarity	NPC182717
0.6909	Remote Similarity	NPC62755
0.6897	Remote Similarity	NPC168518
0.6897	Remote Similarity	NPC105780
0.6875	Remote Similarity	NPC64123
0.6875	Remote Similarity	NPC238352
0.6875	Remote Similarity	NPC477009
0.6875	Remote Similarity	NPC19569
0.6875	Remote Similarity	NPC308844
0.6875	Remote Similarity	NPC61503
0.6866	Remote Similarity	NPC145498
0.6863	Remote Similarity	NPC144023
0.6857	Remote Similarity	NPC151622
0.6857	Remote Similarity	NPC186554
0.6857	Remote Similarity	NPC76966
0.6857	Remote Similarity	NPC472305
0.6857	Remote Similarity	NPC265588
0.6857	Remote Similarity	NPC7629
0.6833	Remote Similarity	NPC52012
0.6825	Remote Similarity	NPC211291
0.6825	Remote Similarity	NPC133368
0.6818	Remote Similarity	NPC224532
0.6818	Remote Similarity	NPC160209
0.6818	Remote Similarity	NPC32055
0.6812	Remote Similarity	NPC201048
0.6812	Remote Similarity	NPC471797
0.6812	Remote Similarity	NPC476366
0.6812	Remote Similarity	NPC100334
0.6786	Remote Similarity	NPC182102
0.6786	Remote Similarity	NPC26960
0.678	Remote Similarity	NPC298299
0.6769	Remote Similarity	NPC272125
0.6769	Remote Similarity	NPC311736
0.6769	Remote Similarity	NPC149680
0.6765	Remote Similarity	NPC242001
0.6765	Remote Similarity	NPC110799
0.6765	Remote Similarity	NPC160817
0.6761	Remote Similarity	NPC318495
0.6761	Remote Similarity	NPC477426
0.6761	Remote Similarity	NPC325946
0.6761	Remote Similarity	NPC40049
0.6761	Remote Similarity	NPC474826
0.6761	Remote Similarity	NPC257666
0.6761	Remote Similarity	NPC477425
0.6761	Remote Similarity	NPC198968
0.6761	Remote Similarity	NPC155986
0.6761	Remote Similarity	NPC266193
0.6761	Remote Similarity	NPC34110
0.6761	Remote Similarity	NPC477427
0.6727	Remote Similarity	NPC91962
0.6724	Remote Similarity	NPC165755
0.6721	Remote Similarity	NPC226848

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 NPC306195 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	2908
0.2-0.3	4110
0.3-0.4	1460
0.4-0.5	361
0.5-0.6	136
0.6-0.7	20
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8103	Intermediate Similarity	NPD368	Approved
0.7679	Intermediate Similarity	NPD342	Phase 1
0.7273	Intermediate Similarity	NPD4243	Approved
0.7083	Intermediate Similarity	NPD319	Phase 1
0.7059	Intermediate Similarity	NPD4784	Approved
0.7059	Intermediate Similarity	NPD4785	Approved
0.7031	Intermediate Similarity	NPD7331	Phase 2
0.6957	Remote Similarity	NPD5275	Approved
0.6957	Remote Similarity	NPD4190	Phase 3
0.6716	Remote Similarity	NPD6923	Approved
0.6716	Remote Similarity	NPD6922	Approved
0.6714	Remote Similarity	NPD7339	Approved
0.6714	Remote Similarity	NPD6942	Approved
0.662	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7143	Approved
0.6618	Remote Similarity	NPD7144	Approved
0.6615	Remote Similarity	NPD7341	Phase 2
0.6575	Remote Similarity	NPD4195	Approved
0.6571	Remote Similarity	NPD6924	Approved
0.6571	Remote Similarity	NPD6926	Approved
0.6522	Remote Similarity	NPD7152	Approved
0.6522	Remote Similarity	NPD7150	Approved
0.6522	Remote Similarity	NPD7151	Approved
0.6479	Remote Similarity	NPD8264	Approved
0.6393	Remote Similarity	NPD4219	Approved
0.6389	Remote Similarity	NPD6933	Approved
0.6364	Remote Similarity	NPD388	Approved
0.6364	Remote Similarity	NPD386	Approved
0.6351	Remote Similarity	NPD7645	Phase 2
0.6316	Remote Similarity	NPD4223	Phase 3
0.6316	Remote Similarity	NPD4221	Approved
0.6301	Remote Similarity	NPD6932	Approved
0.6267	Remote Similarity	NPD7525	Registered
0.6232	Remote Similarity	NPD791	Approved
0.6232	Remote Similarity	NPD15	Approved
0.6216	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.619	Remote Similarity	NPD287	Approved
0.6154	Remote Similarity	NPD4197	Approved
0.6133	Remote Similarity	NPD6683	Phase 2
0.6111	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD3667	Approved
0.6081	Remote Similarity	NPD6925	Approved
0.6081	Remote Similarity	NPD5776	Phase 2
0.6076	Remote Similarity	NPD5329	Approved
0.6053	Remote Similarity	NPD6931	Approved
0.6053	Remote Similarity	NPD6930	Phase 2
0.6053	Remote Similarity	NPD7509	Discontinued
0.6053	Remote Similarity	NPD7514	Phase 3
0.6053	Remote Similarity	NPD7332	Phase 2
0.6053	Remote Similarity	NPD4695	Discontinued
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD1082	Approved
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD4138	Approved
0.6	Remote Similarity	NPD1145	Discontinued
0.6	Remote Similarity	NPD4694	Approved
0.6	Remote Similarity	NPD5205	Approved
0.6	Remote Similarity	NPD4688	Approved
0.6	Remote Similarity	NPD5280	Approved
0.6	Remote Similarity	NPD4693	Phase 3
0.6	Remote Similarity	NPD4690	Approved
0.6	Remote Similarity	NPD4623	Approved
0.6	Remote Similarity	NPD4689	Approved
0.6	Remote Similarity	NPD5690	Phase 2
0.5974	Remote Similarity	NPD6898	Phase 1
0.5965	Remote Similarity	NPD384	Approved
0.5965	Remote Similarity	NPD385	Approved
0.5949	Remote Similarity	NPD3133	Approved
0.5949	Remote Similarity	NPD4786	Approved
0.5949	Remote Similarity	NPD3666	Approved
0.5949	Remote Similarity	NPD3665	Phase 1
0.5946	Remote Similarity	NPD1346	Approved
0.5926	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD6929	Approved
0.5909	Remote Similarity	NPD4194	Approved
0.5909	Remote Similarity	NPD4191	Approved
0.5909	Remote Similarity	NPD4193	Approved
0.5909	Remote Similarity	NPD4192	Approved
0.5882	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4722	Approved
0.5854	Remote Similarity	NPD4723	Approved
0.5844	Remote Similarity	NPD4748	Discontinued
0.5823	Remote Similarity	NPD6695	Phase 3
0.5821	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD3618	Phase 1
0.5789	Remote Similarity	NPD4265	Approved
0.5789	Remote Similarity	NPD3617	Approved
0.5783	Remote Similarity	NPD4753	Phase 2
0.5775	Remote Similarity	NPD4137	Phase 3
0.5769	Remote Similarity	NPD6902	Approved
0.5769	Remote Similarity	NPD4139	Approved
0.5769	Remote Similarity	NPD4692	Approved
0.5763	Remote Similarity	NPD8262	Approved
0.5753	Remote Similarity	NPD4732	Discontinued
0.575	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD367	Approved
0.5694	Remote Similarity	NPD4691	Approved
0.5694	Remote Similarity	NPD4747	Approved
0.5679	Remote Similarity	NPD1696	Phase 3
0.5679	Remote Similarity	NPD6893	Approved
0.5672	Remote Similarity	NPD834	Approved
0.5672	Remote Similarity	NPD835	Approved
0.5663	Remote Similarity	NPD4518	Approved
0.5647	Remote Similarity	NPD5281	Approved
0.5647	Remote Similarity	NPD5284	Approved
0.5645	Remote Similarity	NPD3172	Approved
0.5641	Remote Similarity	NPD4822	Approved
0.5641	Remote Similarity	NPD4820	Approved
0.5641	Remote Similarity	NPD4821	Approved
0.5641	Remote Similarity	NPD4819	Approved
0.561	Remote Similarity	NPD5279	Phase 3

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