NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	260.554
LogP:	4.139
LogD:	2.997
LogS:	-3.202
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	4.089
Fsp3:	0.667
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:	-4.659
MDCK Permeability:	1.5923298633424565e-05
Pgp-inhibitor:	0.071
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	98.07072448730469%
Volume Distribution (VD):	0.483
Pgp-substrate:	2.5726704597473145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.654
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.777
CYP2C9-inhibitor:	0.149
CYP2C9-substrate:	0.474
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.35

ADMET: Excretion

Clearance (CL):	1.81
Half-life (T1/2):	0.561

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.456
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.143
Skin Sensitization:	0.907
Carcinogencity:	0.456
Eye Corrosion:	0.025
Eye Irritation:	0.632
Respiratory Toxicity:	0.799

Download Data

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

Natural Product: NPC81907

Natural Product ID:	NPC81907
*Common Name:**	Valerenic Acid
IUPAC Name:	(E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid
Synonyms:	Valerenic Acid
Standard InCHIKey:	FEBNTWHYQKGEIQ-SUKRRCERSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8+/t9-,12+,13-/m1/s1
SMILES:	C[C@@H]1CC[C@H](C2=C(CC[C@H]12)C)/C=C(/C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1545045
PubChem CID:	6440940
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
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	roots	n.a.	n.a.	PMID[12398547]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[18164718]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO17333.1	Valeriana officinalis var. latifolia	Varieties	Caprifoliaceae	Eukaryota	roots	n.a.	n.a.	PMID[20812738]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[547813]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27015	Valeriana hardwickii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17333.1	Valeriana officinalis var. latifolia	Varieties	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17333.1	Valeriana officinalis var. latifolia	Varieties	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27015	Valeriana hardwickii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27015	Valeriana hardwickii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	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
EC50	4
Others	11
Potency	29

Activity Type	# Activity
Cell Line	3
Individual Protein	20
Organism	1
Others	15
Protein Complex	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	63375.3	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	20216.3	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	56977.2	nM	PubChem BioAssay data set
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	39810.7	nM	PMID[524477]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	50118.7	nM	PMID[524477]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	12589.3	nM	PMID[524477]
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[524477]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	0.8	nM	PMID[524477]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[524477]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[524477]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	74978.0	nM	PMID[524477]
NPT102	Individual Protein	Interleukin-8	Homo sapiens	Potency	n.a.	74978.0	nM	PMID[524477]
NPT103	Individual Protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	37578.0	nM	PMID[524477]
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	EC50	=	27000.0	nM	PMID[524481]
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	FC	=	9.0	n.a.	PMID[524481]
NPT5983	Individual Protein	Retinoid X receptor beta	Homo sapiens	EC50	=	5200.0	nM	PMID[524481]
NPT5983	Individual Protein	Retinoid X receptor beta	Homo sapiens	FC	=	69.0	n.a.	PMID[524481]
NPT5981	Individual Protein	Retinoid X receptor gamma	Homo sapiens	EC50	=	43000.0	nM	PMID[524481]
NPT5981	Individual Protein	Retinoid X receptor gamma	Homo sapiens	FC	=	4.0	n.a.	PMID[524481]
NPT2	Others	Unspecified		Potency	n.a.	3595	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	20041	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	28308.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	56977.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	45258.6	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	14312	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	71108.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	35638.6	nM	PubChem BioAssay data set
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	17782.8	nM	PMID[524477]
NPT2	Others	Unspecified		Activity	=	400.0	%	PMID[524478]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[524477]
NPT2	Others	Unspecified		Potency	n.a.	2238.7	nM	PMID[524477]
NPT2	Others	Unspecified		Imax	=	15.0	%	PMID[524479]
NPT2	Others	Unspecified		Imax	=	4.0	%	PMID[524479]
NPT617	Organism	Danio rerio	Danio rerio	MTD	=	10.0	uM	PMID[524480]
NPT999	Protein Complex	GABA-A receptor; alpha-1/beta-3/gamma-2	Homo sapiens	Activity	=	536.0	%	PMID[524482]
NPT999	Protein Complex	GABA-A receptor; alpha-1/beta-3/gamma-2	Homo sapiens	Activity	=	344.0	%	PMID[524482]
NPT999	Protein Complex	GABA-A receptor; alpha-1/beta-3/gamma-2	Homo sapiens	EC50	=	19000.0	nM	PMID[524482]
NPT999	Protein Complex	GABA-A receptor; alpha-1/beta-3/gamma-2	Homo sapiens	Emax	=	670.0	%	PMID[524482]
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	Activity	=	-115.0	pA	PMID[524482]

☑ 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 NPC81907 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	117
0.1-0.2	1344
0.2-0.3	10397
0.3-0.4	15866
0.4-0.5	8578
0.5-0.6	5313
0.6-0.7	966
0.7-0.8	104
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8472	Intermediate Similarity	NPC172066
0.8209	Intermediate Similarity	NPC259156
0.8209	Intermediate Similarity	NPC242945
0.8209	Intermediate Similarity	NPC255781
0.806	Intermediate Similarity	NPC107258
0.8026	Intermediate Similarity	NPC472867
0.7887	Intermediate Similarity	NPC21944
0.7821	Intermediate Similarity	NPC248758
0.7821	Intermediate Similarity	NPC19849
0.7821	Intermediate Similarity	NPC472865
0.7821	Intermediate Similarity	NPC472864
0.7808	Intermediate Similarity	NPC476346
0.7792	Intermediate Similarity	NPC142253
0.7792	Intermediate Similarity	NPC469799
0.7792	Intermediate Similarity	NPC469806
0.7792	Intermediate Similarity	NPC472239
0.7792	Intermediate Similarity	NPC3511
0.7778	Intermediate Similarity	NPC35656
0.7778	Intermediate Similarity	NPC56747
0.7778	Intermediate Similarity	NPC180015
0.7778	Intermediate Similarity	NPC130016
0.7778	Intermediate Similarity	NPC109576
0.7703	Intermediate Similarity	NPC19907
0.7692	Intermediate Similarity	NPC279639
0.7692	Intermediate Similarity	NPC97913
0.7692	Intermediate Similarity	NPC3856
0.7639	Intermediate Similarity	NPC133253
0.7625	Intermediate Similarity	NPC472869
0.7595	Intermediate Similarity	NPC178025
0.7595	Intermediate Similarity	NPC164577
0.7595	Intermediate Similarity	NPC16287
0.7595	Intermediate Similarity	NPC87552
0.7595	Intermediate Similarity	NPC181743
0.7571	Intermediate Similarity	NPC254886
0.7568	Intermediate Similarity	NPC476795
0.7568	Intermediate Similarity	NPC469803
0.7564	Intermediate Similarity	NPC469804
0.7564	Intermediate Similarity	NPC469805
0.7532	Intermediate Similarity	NPC469798
0.7532	Intermediate Similarity	NPC469797
0.75	Intermediate Similarity	NPC60350
0.75	Intermediate Similarity	NPC198240
0.75	Intermediate Similarity	NPC169095
0.75	Intermediate Similarity	NPC8571
0.7439	Intermediate Similarity	NPC472870
0.7407	Intermediate Similarity	NPC186975
0.7397	Intermediate Similarity	NPC29328
0.7368	Intermediate Similarity	NPC97377
0.7368	Intermediate Similarity	NPC61952
0.7368	Intermediate Similarity	NPC132542
0.7353	Intermediate Similarity	NPC317177
0.7353	Intermediate Similarity	NPC317025
0.7353	Intermediate Similarity	NPC326645
0.7353	Intermediate Similarity	NPC329416
0.7317	Intermediate Similarity	NPC236618
0.7317	Intermediate Similarity	NPC476293
0.7308	Intermediate Similarity	NPC233352
0.7308	Intermediate Similarity	NPC138492
0.7308	Intermediate Similarity	NPC824
0.7308	Intermediate Similarity	NPC271104
0.7262	Intermediate Similarity	NPC472866
0.725	Intermediate Similarity	NPC215893
0.7229	Intermediate Similarity	NPC117122
0.72	Intermediate Similarity	NPC75485
0.72	Intermediate Similarity	NPC168975
0.7183	Intermediate Similarity	NPC322035
0.7183	Intermediate Similarity	NPC100719
0.7183	Intermediate Similarity	NPC185587
0.7183	Intermediate Similarity	NPC166791
0.7179	Intermediate Similarity	NPC190211
0.7143	Intermediate Similarity	NPC472240
0.7143	Intermediate Similarity	NPC146554
0.7143	Intermediate Similarity	NPC66344
0.7143	Intermediate Similarity	NPC262858
0.7125	Intermediate Similarity	NPC224455
0.7123	Intermediate Similarity	NPC67608
0.7105	Intermediate Similarity	NPC472327
0.7105	Intermediate Similarity	NPC68624
0.7093	Intermediate Similarity	NPC472871
0.7077	Intermediate Similarity	NPC474127
0.7059	Intermediate Similarity	NPC309825
0.7051	Intermediate Similarity	NPC105197
0.7037	Intermediate Similarity	NPC42476
0.7037	Intermediate Similarity	NPC49019
0.7037	Intermediate Similarity	NPC57370
0.7027	Intermediate Similarity	NPC235586
0.7024	Intermediate Similarity	NPC249889
0.7024	Intermediate Similarity	NPC193843
0.7013	Intermediate Similarity	NPC7629
0.7013	Intermediate Similarity	NPC4509
0.7013	Intermediate Similarity	NPC472305
0.7013	Intermediate Similarity	NPC473223
0.7013	Intermediate Similarity	NPC474463
0.7013	Intermediate Similarity	NPC151622
0.7013	Intermediate Similarity	NPC180886
0.7	Intermediate Similarity	NPC477372
0.6986	Remote Similarity	NPC476614
0.6977	Remote Similarity	NPC470113
0.6977	Remote Similarity	NPC110923
0.6977	Remote Similarity	NPC74296
0.6977	Remote Similarity	NPC23217
0.6977	Remote Similarity	NPC212948
0.6977	Remote Similarity	NPC474018
0.6977	Remote Similarity	NPC473986
0.6974	Remote Similarity	NPC20025
0.6974	Remote Similarity	NPC213223
0.6962	Remote Similarity	NPC472013
0.6962	Remote Similarity	NPC476624
0.6962	Remote Similarity	NPC170394
0.6951	Remote Similarity	NPC470800
0.6951	Remote Similarity	NPC302360
0.6944	Remote Similarity	NPC308294
0.6944	Remote Similarity	NPC142423
0.6941	Remote Similarity	NPC310236
0.6941	Remote Similarity	NPC262043
0.6933	Remote Similarity	NPC67076
0.6933	Remote Similarity	NPC160817
0.6933	Remote Similarity	NPC319163
0.6923	Remote Similarity	NPC34110
0.6923	Remote Similarity	NPC472014
0.6914	Remote Similarity	NPC2524
0.6914	Remote Similarity	NPC320514
0.6912	Remote Similarity	NPC471619
0.6905	Remote Similarity	NPC136948
0.6901	Remote Similarity	NPC212210
0.6901	Remote Similarity	NPC234767
0.6901	Remote Similarity	NPC150162
0.6901	Remote Similarity	NPC329698
0.6897	Remote Similarity	NPC38232
0.6897	Remote Similarity	NPC214697
0.6897	Remote Similarity	NPC476304
0.6883	Remote Similarity	NPC65650
0.6875	Remote Similarity	NPC10636
0.6875	Remote Similarity	NPC281880
0.6875	Remote Similarity	NPC472301
0.6867	Remote Similarity	NPC65661
0.6867	Remote Similarity	NPC142649
0.6867	Remote Similarity	NPC42586
0.6867	Remote Similarity	NPC86316
0.6867	Remote Similarity	NPC473251
0.6867	Remote Similarity	NPC329630
0.6867	Remote Similarity	NPC269638
0.6867	Remote Similarity	NPC29447
0.6867	Remote Similarity	NPC106416
0.6867	Remote Similarity	NPC217394
0.6867	Remote Similarity	NPC109528
0.6854	Remote Similarity	NPC190713
0.6849	Remote Similarity	NPC472875
0.6842	Remote Similarity	NPC321017
0.6835	Remote Similarity	NPC19443
0.6835	Remote Similarity	NPC239098
0.6835	Remote Similarity	NPC192006
0.6835	Remote Similarity	NPC59436
0.6835	Remote Similarity	NPC179028
0.6835	Remote Similarity	NPC476627
0.6835	Remote Similarity	NPC74410
0.6829	Remote Similarity	NPC474976
0.6829	Remote Similarity	NPC41539
0.6829	Remote Similarity	NPC474790
0.6829	Remote Similarity	NPC65350
0.6829	Remote Similarity	NPC311070
0.6829	Remote Similarity	NPC476927
0.6829	Remote Similarity	NPC297398
0.6829	Remote Similarity	NPC79945
0.6824	Remote Similarity	NPC72397
0.6824	Remote Similarity	NPC48107
0.6818	Remote Similarity	NPC476186
0.6812	Remote Similarity	NPC276764
0.6812	Remote Similarity	NPC472304
0.68	Remote Similarity	NPC251929
0.68	Remote Similarity	NPC2634
0.68	Remote Similarity	NPC265782
0.68	Remote Similarity	NPC316029
0.679	Remote Similarity	NPC6663
0.679	Remote Similarity	NPC78677
0.679	Remote Similarity	NPC40228
0.679	Remote Similarity	NPC59994
0.679	Remote Similarity	NPC278459
0.679	Remote Similarity	NPC159148
0.6786	Remote Similarity	NPC476043
0.6786	Remote Similarity	NPC194417
0.6782	Remote Similarity	NPC204341
0.6782	Remote Similarity	NPC476187
0.6782	Remote Similarity	NPC473675
0.6778	Remote Similarity	NPC476253
0.6765	Remote Similarity	NPC11130
0.6765	Remote Similarity	NPC283502
0.6761	Remote Similarity	NPC124112
0.6761	Remote Similarity	NPC322457
0.6761	Remote Similarity	NPC174956
0.6757	Remote Similarity	NPC117804
0.6753	Remote Similarity	NPC241854
0.6753	Remote Similarity	NPC251970
0.6753	Remote Similarity	NPC476046
0.675	Remote Similarity	NPC477371
0.675	Remote Similarity	NPC158846
0.6747	Remote Similarity	NPC194937
0.6747	Remote Similarity	NPC476038
0.6747	Remote Similarity	NPC165064
0.6747	Remote Similarity	NPC474693

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 NPC81907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	108
0.1-0.2	1803
0.2-0.3	4633
0.3-0.4	1933
0.4-0.5	414
0.5-0.6	243
0.6-0.7	16
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
0.7353	Intermediate Similarity	NPD4192	Approved
0.7353	Intermediate Similarity	NPD4193	Approved
0.7353	Intermediate Similarity	NPD4194	Approved
0.7353	Intermediate Similarity	NPD4191	Approved
0.68	Remote Similarity	NPD4691	Approved
0.6667	Remote Similarity	NPD4137	Phase 3
0.6588	Remote Similarity	NPD4519	Discontinued
0.6588	Remote Similarity	NPD4623	Approved
0.6579	Remote Similarity	NPD4747	Approved
0.6543	Remote Similarity	NPD4195	Approved
0.6538	Remote Similarity	NPD4058	Approved
0.6506	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6404	Discontinued
0.6329	Remote Similarity	NPD4687	Approved
0.6329	Remote Similarity	NPD5733	Approved
0.631	Remote Similarity	NPD4221	Approved
0.631	Remote Similarity	NPD4223	Phase 3
0.6308	Remote Similarity	NPD4220	Pre-registration
0.6282	Remote Similarity	NPD5276	Approved
0.6279	Remote Similarity	NPD5363	Approved
0.6279	Remote Similarity	NPD1696	Phase 3
0.6277	Remote Similarity	NPD7639	Approved
0.6277	Remote Similarity	NPD7640	Approved
0.6235	Remote Similarity	NPD5362	Discontinued
0.6222	Remote Similarity	NPD5284	Approved
0.6222	Remote Similarity	NPD5281	Approved
0.622	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5690	Phase 2
0.6197	Remote Similarity	NPD287	Approved
0.617	Remote Similarity	NPD4225	Approved
0.617	Remote Similarity	NPD7638	Approved
0.6164	Remote Similarity	NPD368	Approved
0.6163	Remote Similarity	NPD3665	Phase 1
0.6163	Remote Similarity	NPD3133	Approved
0.6163	Remote Similarity	NPD4197	Approved
0.6163	Remote Similarity	NPD3666	Approved
0.6104	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD5329	Approved
0.6071	Remote Similarity	NPD4821	Approved
0.6071	Remote Similarity	NPD4695	Discontinued
0.6071	Remote Similarity	NPD4822	Approved
0.6071	Remote Similarity	NPD4820	Approved
0.6071	Remote Similarity	NPD4819	Approved
0.6047	Remote Similarity	NPD7154	Phase 3
0.6047	Remote Similarity	NPD5332	Approved
0.6047	Remote Similarity	NPD5331	Approved
0.6044	Remote Similarity	NPD7637	Suspended
0.6024	Remote Similarity	NPD3617	Approved
0.6024	Remote Similarity	NPD4268	Approved
0.6024	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD4271	Approved
0.6023	Remote Similarity	NPD4689	Approved
0.6023	Remote Similarity	NPD5205	Approved
0.6023	Remote Similarity	NPD4688	Approved
0.6023	Remote Similarity	NPD4694	Approved
0.6023	Remote Similarity	NPD7521	Approved
0.6023	Remote Similarity	NPD5330	Approved
0.6023	Remote Similarity	NPD7334	Approved
0.6023	Remote Similarity	NPD6409	Approved
0.6023	Remote Similarity	NPD3618	Phase 1
0.6023	Remote Similarity	NPD5280	Approved
0.6023	Remote Similarity	NPD4693	Phase 3
0.6023	Remote Similarity	NPD7146	Approved
0.6023	Remote Similarity	NPD4690	Approved
0.6023	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4138	Approved
0.6023	Remote Similarity	NPD6684	Approved
0.6022	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD342	Phase 1
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4790	Discontinued
0.5977	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5785	Approved
0.593	Remote Similarity	NPD3667	Approved
0.593	Remote Similarity	NPD4270	Approved
0.593	Remote Similarity	NPD4269	Approved
0.5921	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD4219	Approved
0.5909	Remote Similarity	NPD1694	Approved
0.5909	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6084	Phase 2
0.5895	Remote Similarity	NPD6083	Phase 2
0.5889	Remote Similarity	NPD5737	Approved
0.5889	Remote Similarity	NPD6672	Approved
0.5889	Remote Similarity	NPD5208	Approved
0.5889	Remote Similarity	NPD6903	Approved
0.5889	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7332	Phase 2
0.5882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4252	Approved
0.5875	Remote Similarity	NPD4243	Approved
0.587	Remote Similarity	NPD5693	Phase 1
0.587	Remote Similarity	NPD7515	Phase 2
0.587	Remote Similarity	NPD6079	Approved
0.5862	Remote Similarity	NPD3971	Phase 1
0.5862	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD6049	Phase 2
0.5851	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD7331	Phase 2
0.5843	Remote Similarity	NPD5279	Phase 3
0.5833	Remote Similarity	NPD5696	Approved
0.5824	Remote Similarity	NPD6080	Approved
0.5824	Remote Similarity	NPD6673	Approved
0.5824	Remote Similarity	NPD5328	Approved
0.5824	Remote Similarity	NPD4753	Phase 2
0.5824	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD6904	Approved
0.5806	Remote Similarity	NPD6399	Phase 3
0.5795	Remote Similarity	NPD4786	Approved
0.5783	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD9411	Phase 1
0.5778	Remote Similarity	NPD3573	Approved
0.5761	Remote Similarity	NPD5207	Approved
0.5761	Remote Similarity	NPD5692	Phase 3
0.5747	Remote Similarity	NPD5209	Approved
0.5745	Remote Similarity	NPD7748	Approved
0.5732	Remote Similarity	NPD4784	Approved
0.5732	Remote Similarity	NPD4785	Approved
0.573	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5776	Phase 2
0.5714	Remote Similarity	NPD4756	Discovery
0.5714	Remote Similarity	NPD6925	Approved
0.5699	Remote Similarity	NPD5694	Approved
0.5699	Remote Similarity	NPD6050	Approved
0.5698	Remote Similarity	NPD7514	Phase 3
0.5684	Remote Similarity	NPD5210	Approved
0.5684	Remote Similarity	NPD4629	Approved
0.5667	Remote Similarity	NPD6098	Approved
0.5667	Remote Similarity	NPD5786	Approved
0.5663	Remote Similarity	NPD6942	Approved
0.5663	Remote Similarity	NPD5275	Approved
0.5663	Remote Similarity	NPD4190	Phase 3
0.5663	Remote Similarity	NPD9716	Approved
0.5663	Remote Similarity	NPD8264	Approved
0.5663	Remote Similarity	NPD7339	Approved
0.5657	Remote Similarity	NPD7632	Discontinued
0.5657	Remote Similarity	NPD5211	Phase 2
0.5652	Remote Similarity	NPD6051	Approved
0.5647	Remote Similarity	NPD7145	Approved
0.5638	Remote Similarity	NPD4202	Approved
0.5632	Remote Similarity	NPD857	Phase 3
0.5632	Remote Similarity	NPD6898	Phase 1
0.5632	Remote Similarity	NPD6902	Approved
0.5625	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7614	Phase 1
0.5625	Remote Similarity	NPD6922	Approved
0.5625	Remote Similarity	NPD6923	Approved
0.5625	Remote Similarity	NPD5222	Approved
0.5625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5221	Approved
0.5606	Remote Similarity	NPD39	Approved
0.5604	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6647	Phase 2

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