NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	138.1
Volume:	159.181
LogP:	1.546
LogD:	0.99
LogS:	-1.129
# Rotatable Bonds:	0
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.502
Synthetic Accessibility Score:	2.737
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.563
MDCK Permeability:	3.0091056032688357e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.959
Plasma Protein Binding (PPB):	69.4067611694336%
Volume Distribution (VD):	0.73
Pgp-substrate:	47.941898345947266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.145
CYP1A2-substrate:	0.751
CYP2C19-inhibitor:	0.801
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.276
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.292

ADMET: Excretion

Clearance (CL):	6.648
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.309
Drug-inuced Liver Injury (DILI):	0.173
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.908
Carcinogencity:	0.861
Eye Corrosion:	0.903
Eye Irritation:	0.947
Respiratory Toxicity:	0.544

Download Data

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

Natural Product: NPC64866

Natural Product ID:	NPC64866
*Common Name:**	3,5,5-Trimethylcyclohex-2-En-1-One
IUPAC Name:	3,5,5-trimethylcyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	HJOVHMDZYOCNQW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3
SMILES:	CC1=CC(=O)CC(C)(C)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1882894
PubChem CID:	6544
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/hlca.19270100148]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Petals	n.a.	n.a.	PMID[15043425]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	feces	n.a.	n.a.	PMID[20402524]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24014097]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24128451]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24338885]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11045	Paederia scandens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO420	Eucheuma muricatum	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11045	Paederia scandens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO420	Eucheuma muricatum	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11045	Paederia scandens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11045	Paederia scandens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO420	Eucheuma muricatum	Species	Solieriaceae	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
NPO7576	NPC64866	Other	Stem	0.006	0.006	0.006	mg/100g	Database [DUKE]

☑ 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	10

Activity Type	# Activity
Individual Protein	2
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[487556]
NPT2	Others	Unspecified		Potency	n.a.	173.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1266.5	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	14210.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	25269.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2503.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	4005	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	4994.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	39671.7	nM	PubChem BioAssay data set

☑ 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 NPC64866 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	220
0.1-0.2	4490
0.2-0.3	18655
0.3-0.4	11224
0.4-0.5	5777
0.5-0.6	1841
0.6-0.7	358
0.7-0.8	100
0.8-0.85	16
0.85-0.9	14
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.898	High Similarity	NPC32351
0.8723	High Similarity	NPC25771
0.8704	High Similarity	NPC170799
0.8704	High Similarity	NPC311852
0.8704	High Similarity	NPC308108
0.86	High Similarity	NPC163984
0.86	High Similarity	NPC58970
0.86	High Similarity	NPC176819
0.8571	High Similarity	NPC91962
0.8511	High Similarity	NPC292463
0.8462	Intermediate Similarity	NPC268564
0.8462	Intermediate Similarity	NPC37644
0.8462	Intermediate Similarity	NPC23117
0.8393	Intermediate Similarity	NPC127582
0.8333	Intermediate Similarity	NPC473733
0.8246	Intermediate Similarity	NPC213152
0.8235	Intermediate Similarity	NPC228776
0.8113	Intermediate Similarity	NPC14002
0.8103	Intermediate Similarity	NPC288253
0.8036	Intermediate Similarity	NPC56905
0.8036	Intermediate Similarity	NPC27610
0.8	Intermediate Similarity	NPC236355
0.8	Intermediate Similarity	NPC4079
0.8	Intermediate Similarity	NPC14917
0.7966	Intermediate Similarity	NPC212210
0.7966	Intermediate Similarity	NPC6697
0.7966	Intermediate Similarity	NPC475124
0.7966	Intermediate Similarity	NPC285371
0.7963	Intermediate Similarity	NPC5626
0.7895	Intermediate Similarity	NPC472304
0.7895	Intermediate Similarity	NPC276764
0.7885	Intermediate Similarity	NPC116906
0.7885	Intermediate Similarity	NPC118788
0.7857	Intermediate Similarity	NPC115385
0.7833	Intermediate Similarity	NPC251118
0.7833	Intermediate Similarity	NPC470329
0.78	Intermediate Similarity	NPC166788
0.7797	Intermediate Similarity	NPC165695
0.7797	Intermediate Similarity	NPC32285
0.7778	Intermediate Similarity	NPC296311
0.7719	Intermediate Similarity	NPC266295
0.7719	Intermediate Similarity	NPC94991
0.7667	Intermediate Similarity	NPC4638
0.7647	Intermediate Similarity	NPC262558
0.7647	Intermediate Similarity	NPC8610
0.7636	Intermediate Similarity	NPC209431
0.7636	Intermediate Similarity	NPC100809
0.7593	Intermediate Similarity	NPC471751
0.7586	Intermediate Similarity	NPC285594
0.7586	Intermediate Similarity	NPC259261
0.7586	Intermediate Similarity	NPC96551
0.7581	Intermediate Similarity	NPC269985
0.7581	Intermediate Similarity	NPC475523
0.75	Intermediate Similarity	NPC275472
0.75	Intermediate Similarity	NPC202118
0.75	Intermediate Similarity	NPC197238
0.746	Intermediate Similarity	NPC87141
0.746	Intermediate Similarity	NPC310992
0.746	Intermediate Similarity	NPC188292
0.746	Intermediate Similarity	NPC155198
0.746	Intermediate Similarity	NPC260474
0.7458	Intermediate Similarity	NPC25853
0.7455	Intermediate Similarity	NPC295777
0.7455	Intermediate Similarity	NPC69898
0.7455	Intermediate Similarity	NPC474141
0.7455	Intermediate Similarity	NPC45283
0.7451	Intermediate Similarity	NPC191337
0.7414	Intermediate Similarity	NPC30215
0.7407	Intermediate Similarity	NPC30433
0.7407	Intermediate Similarity	NPC27438
0.74	Intermediate Similarity	NPC216921
0.74	Intermediate Similarity	NPC301972
0.7377	Intermediate Similarity	NPC469662
0.7358	Intermediate Similarity	NPC145311
0.7344	Intermediate Similarity	NPC256846
0.7344	Intermediate Similarity	NPC139397
0.7344	Intermediate Similarity	NPC136473
0.7333	Intermediate Similarity	NPC60565
0.7333	Intermediate Similarity	NPC97322
0.7321	Intermediate Similarity	NPC250539
0.7308	Intermediate Similarity	NPC100380
0.7255	Intermediate Similarity	NPC477686
0.7241	Intermediate Similarity	NPC49575
0.7241	Intermediate Similarity	NPC193695
0.7241	Intermediate Similarity	NPC192427
0.7241	Intermediate Similarity	NPC267626
0.7241	Intermediate Similarity	NPC230823
0.7241	Intermediate Similarity	NPC55004
0.7231	Intermediate Similarity	NPC265782
0.7231	Intermediate Similarity	NPC307176
0.7231	Intermediate Similarity	NPC260040
0.7231	Intermediate Similarity	NPC159577
0.7231	Intermediate Similarity	NPC251929
0.7231	Intermediate Similarity	NPC35734
0.7231	Intermediate Similarity	NPC2634
0.7231	Intermediate Similarity	NPC282593
0.7222	Intermediate Similarity	NPC15325
0.7213	Intermediate Similarity	NPC167256
0.7193	Intermediate Similarity	NPC200258
0.7143	Intermediate Similarity	NPC111474
0.7143	Intermediate Similarity	NPC113082
0.7121	Intermediate Similarity	NPC474562
0.7121	Intermediate Similarity	NPC54123
0.7121	Intermediate Similarity	NPC190035
0.7121	Intermediate Similarity	NPC115023
0.7119	Intermediate Similarity	NPC60772
0.7097	Intermediate Similarity	NPC150162
0.7097	Intermediate Similarity	NPC473902
0.7091	Intermediate Similarity	NPC236623
0.7069	Intermediate Similarity	NPC20603
0.7049	Intermediate Similarity	NPC475795
0.7031	Intermediate Similarity	NPC4370
0.7031	Intermediate Similarity	NPC290350
0.7021	Intermediate Similarity	NPC38497
0.7018	Intermediate Similarity	NPC63396
0.7018	Intermediate Similarity	NPC202850
0.7015	Intermediate Similarity	NPC474228
0.7015	Intermediate Similarity	NPC303613
0.7015	Intermediate Similarity	NPC186042
0.7015	Intermediate Similarity	NPC180015
0.7015	Intermediate Similarity	NPC109576
0.7015	Intermediate Similarity	NPC201562
0.7015	Intermediate Similarity	NPC153660
0.7015	Intermediate Similarity	NPC130016
0.7015	Intermediate Similarity	NPC29542
0.7015	Intermediate Similarity	NPC251705
0.7015	Intermediate Similarity	NPC470045
0.7015	Intermediate Similarity	NPC323437
0.7015	Intermediate Similarity	NPC56747
0.7015	Intermediate Similarity	NPC276336
0.7015	Intermediate Similarity	NPC470044
0.7	Intermediate Similarity	NPC143834
0.6981	Remote Similarity	NPC276009
0.6981	Remote Similarity	NPC22098
0.6981	Remote Similarity	NPC471752
0.6981	Remote Similarity	NPC195246
0.697	Remote Similarity	NPC151045
0.697	Remote Similarity	NPC246722
0.6964	Remote Similarity	NPC22182
0.6935	Remote Similarity	NPC472306
0.6923	Remote Similarity	NPC20610
0.6923	Remote Similarity	NPC39157
0.6923	Remote Similarity	NPC296697
0.6923	Remote Similarity	NPC82477
0.6923	Remote Similarity	NPC142754
0.6912	Remote Similarity	NPC215050
0.6912	Remote Similarity	NPC309852
0.6875	Remote Similarity	NPC185839
0.6875	Remote Similarity	NPC323005
0.6866	Remote Similarity	NPC5701
0.6866	Remote Similarity	NPC181204
0.6866	Remote Similarity	NPC21944
0.6866	Remote Similarity	NPC133253
0.6866	Remote Similarity	NPC225467
0.6866	Remote Similarity	NPC234707
0.6852	Remote Similarity	NPC324812
0.6818	Remote Similarity	NPC182815
0.6818	Remote Similarity	NPC286814
0.6818	Remote Similarity	NPC474060
0.6812	Remote Similarity	NPC169056
0.6812	Remote Similarity	NPC114236
0.6812	Remote Similarity	NPC166018
0.6812	Remote Similarity	NPC65650
0.6812	Remote Similarity	NPC293803
0.6812	Remote Similarity	NPC473171
0.6812	Remote Similarity	NPC225665
0.6812	Remote Similarity	NPC476346
0.6774	Remote Similarity	NPC260573
0.6769	Remote Similarity	NPC20181
0.6769	Remote Similarity	NPC220210
0.6769	Remote Similarity	NPC106613
0.6765	Remote Similarity	NPC247586
0.6735	Remote Similarity	NPC180840
0.6735	Remote Similarity	NPC155880
0.6735	Remote Similarity	NPC92863
0.6724	Remote Similarity	NPC95581
0.6721	Remote Similarity	NPC473494
0.6714	Remote Similarity	NPC69408
0.6714	Remote Similarity	NPC470525
0.6714	Remote Similarity	NPC263582
0.6714	Remote Similarity	NPC1254
0.6714	Remote Similarity	NPC110725
0.6714	Remote Similarity	NPC180886
0.6667	Remote Similarity	NPC208749
0.6667	Remote Similarity	NPC474796
0.6667	Remote Similarity	NPC255021
0.6667	Remote Similarity	NPC469688
0.6667	Remote Similarity	NPC20025
0.6667	Remote Similarity	NPC474797
0.6667	Remote Similarity	NPC321568
0.6667	Remote Similarity	NPC469679
0.6667	Remote Similarity	NPC281986
0.6667	Remote Similarity	NPC22019
0.6667	Remote Similarity	NPC329866
0.662	Remote Similarity	NPC257666
0.662	Remote Similarity	NPC165711
0.662	Remote Similarity	NPC266193
0.662	Remote Similarity	NPC472300
0.662	Remote Similarity	NPC97377
0.6618	Remote Similarity	NPC470078

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 NPC64866 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	3646
0.2-0.3	3955
0.3-0.4	921
0.4-0.5	292
0.5-0.6	95
0.6-0.7	20
0.7-0.8	1
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
0.8704	High Similarity	NPD287	Approved
0.7344	Intermediate Similarity	NPD4137	Phase 3
0.7231	Intermediate Similarity	NPD4691	Approved
0.7231	Intermediate Similarity	NPD4747	Approved
0.7121	Intermediate Similarity	NPD5276	Approved
0.6923	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5733	Approved
0.6912	Remote Similarity	NPD4687	Approved
0.6912	Remote Similarity	NPD4058	Approved
0.6875	Remote Similarity	NPD7331	Phase 2
0.66	Remote Similarity	NPD5783	Phase 3
0.6351	Remote Similarity	NPD4695	Discontinued
0.6333	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4193	Approved
0.625	Remote Similarity	NPD4192	Approved
0.625	Remote Similarity	NPD4194	Approved
0.625	Remote Similarity	NPD4191	Approved
0.6212	Remote Similarity	NPD7341	Phase 2
0.62	Remote Similarity	NPD319	Phase 1
0.6184	Remote Similarity	NPD4223	Phase 3
0.6184	Remote Similarity	NPD4221	Approved
0.6154	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD8028	Phase 2
0.6026	Remote Similarity	NPD3666	Approved
0.6026	Remote Similarity	NPD3133	Approved
0.6026	Remote Similarity	NPD3665	Phase 1
0.6026	Remote Similarity	NPD4197	Approved
0.5949	Remote Similarity	NPD5329	Approved
0.5875	Remote Similarity	NPD7146	Approved
0.5875	Remote Similarity	NPD4693	Phase 3
0.5875	Remote Similarity	NPD4688	Approved
0.5875	Remote Similarity	NPD4519	Discontinued
0.5875	Remote Similarity	NPD4694	Approved
0.5875	Remote Similarity	NPD6684	Approved
0.5875	Remote Similarity	NPD5690	Phase 2
0.5875	Remote Similarity	NPD7521	Approved
0.5875	Remote Similarity	NPD5330	Approved
0.5875	Remote Similarity	NPD4689	Approved
0.5875	Remote Similarity	NPD3618	Phase 1
0.5875	Remote Similarity	NPD7334	Approved
0.5875	Remote Similarity	NPD5279	Phase 3
0.5875	Remote Similarity	NPD4623	Approved
0.5875	Remote Similarity	NPD6409	Approved
0.5875	Remote Similarity	NPD5280	Approved
0.5875	Remote Similarity	NPD4138	Approved
0.5875	Remote Similarity	NPD4690	Approved
0.5875	Remote Similarity	NPD5205	Approved
0.5873	Remote Similarity	NPD8779	Phase 3
0.5867	Remote Similarity	NPD3617	Approved
0.5802	Remote Similarity	NPD3573	Approved
0.5769	Remote Similarity	NPD3667	Approved
0.5732	Remote Similarity	NPD6903	Approved
0.5732	Remote Similarity	NPD5208	Approved
0.5732	Remote Similarity	NPD5737	Approved
0.5732	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD6672	Approved
0.5714	Remote Similarity	NPD4219	Approved
0.5679	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD8039	Approved
0.5663	Remote Similarity	NPD6080	Approved
0.5663	Remote Similarity	NPD5328	Approved
0.5663	Remote Similarity	NPD4753	Phase 2
0.5663	Remote Similarity	NPD6673	Approved
0.5663	Remote Similarity	NPD6904	Approved
0.5645	Remote Similarity	NPD539	Approved
0.5625	Remote Similarity	NPD3668	Phase 3
0.5625	Remote Similarity	NPD4786	Approved
0.5614	Remote Similarity	NPD3174	Discontinued

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