NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.1
Volume:	264.305
LogP:	1.014
LogD:	0.914
LogS:	-2.744
# Rotatable Bonds:	1
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	4.926
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.699
MDCK Permeability:	1.7875092453323305e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	66.77918243408203%
Volume Distribution (VD):	1.271
Pgp-substrate:	37.57740020751953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.249
CYP1A2-substrate:	0.214
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.146
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.3
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	7.27
Half-life (T1/2):	0.712

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.751
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.35
Maximum Recommended Daily Dose:	0.273
Skin Sensitization:	0.936
Carcinogencity:	0.179
Eye Corrosion:	0.049
Eye Irritation:	0.165
Respiratory Toxicity:	0.608

Download Data

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

Natural Product: NPC268298

Natural Product ID:	NPC268298
*Common Name:**	Deoxylactucin
IUPAC Name:	(3aS,9aS,9bS)-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
Synonyms:	Deoxylactucin
Standard InCHIKey:	NIYXMGSLECQTQT-BPNCWPANSA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-7-3-4-10-8(2)15(18)19-14(10)13-9(6-16)5-11(17)12(7)13/h5,10,13-14,16H,2-4,6H2,1H3/t10-,13-,14-/m0/s1
SMILES:	OCC1=CC(=O)C2=C(C)CC[C@@H]3[C@@H]([C@@H]12)OC(=O)C3=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL365239
PubChem CID:	442196
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542368]
NPO2465	Justicia glauca	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1667412]
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24784222]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28139925]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29182349]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184894]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO28635	Cephalotaxus harringtonia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12407	Herba cichorii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28635	Cephalotaxus harringtonia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4151	Rhamnus wightii	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28635	Cephalotaxus harringtonia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1584	Tolypothrix tjipanasensis	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2465	Justicia glauca	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2161	Strychnos ledermannii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17549	Polemonium caeruleum	Species	Polemoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11801	Strychnos axillaris	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO245	Euphorbia biglandulosa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7872	Buxus madagascarica	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4892	Viburnum davidii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9787	Krameria grayi	Species	Krameriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8864	Ceratostomella fimbriata	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11501	Carphephorus corymbosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2434	Lipotriche scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28557	Cacalia hastata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13123	Balanophora harlandii	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3927	Callyspongia fistularis	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO513	Agathosma scaberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
Others	4

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	1
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.1	umol/L	PMID[502425]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	50.0	uM	PMID[502423]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	pIC100	=	-1.69	n.a.	PMID[502423]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	50.0	uM	PMID[502424]
NPT4924	Organism	Haemonchus contortus	Haemonchus contortus	EC	=	4.99	mM	PMID[502426]

☑ 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 NPC268298 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	183
0.1-0.2	1112
0.2-0.3	4766
0.3-0.4	10837
0.4-0.5	14020
0.5-0.6	6607
0.6-0.7	3809
0.7-0.8	1136
0.8-0.85	174
0.85-0.9	49
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC129419
0.9524	High Similarity	NPC237540
0.9286	High Similarity	NPC165162
0.8953	High Similarity	NPC107787
0.8941	High Similarity	NPC115786
0.8941	High Similarity	NPC165287
0.8916	High Similarity	NPC302426
0.8837	High Similarity	NPC78089
0.881	High Similarity	NPC35089
0.881	High Similarity	NPC10276
0.8795	High Similarity	NPC470244
0.8795	High Similarity	NPC470239
0.8778	High Similarity	NPC135776
0.8736	High Similarity	NPC305475
0.8736	High Similarity	NPC475461
0.8721	High Similarity	NPC141193
0.8721	High Similarity	NPC96259
0.8721	High Similarity	NPC114979
0.8721	High Similarity	NPC191476
0.871	High Similarity	NPC141191
0.8706	High Similarity	NPC89555
0.8667	High Similarity	NPC261607
0.8667	High Similarity	NPC300312
0.8667	High Similarity	NPC111114
0.8652	High Similarity	NPC295312
0.8646	High Similarity	NPC100487
0.8621	High Similarity	NPC255307
0.8602	High Similarity	NPC169205
0.8588	High Similarity	NPC301477
0.8588	High Similarity	NPC470241
0.8588	High Similarity	NPC25684
0.8588	High Similarity	NPC281949
0.8587	High Similarity	NPC48803
0.8587	High Similarity	NPC90121
0.8587	High Similarity	NPC193645
0.8587	High Similarity	NPC275960
0.8587	High Similarity	NPC304886
0.8556	High Similarity	NPC106510
0.8556	High Similarity	NPC77337
0.8556	High Similarity	NPC71533
0.8554	High Similarity	NPC65603
0.8495	Intermediate Similarity	NPC185553
0.8488	Intermediate Similarity	NPC229825
0.8478	Intermediate Similarity	NPC470010
0.8478	Intermediate Similarity	NPC470013
0.8478	Intermediate Similarity	NPC262133
0.8478	Intermediate Similarity	NPC477131
0.8478	Intermediate Similarity	NPC167219
0.8478	Intermediate Similarity	NPC323008
0.8471	Intermediate Similarity	NPC69271
0.8471	Intermediate Similarity	NPC74673
0.8462	Intermediate Similarity	NPC131209
0.8452	Intermediate Similarity	NPC299235
0.8452	Intermediate Similarity	NPC108816
0.8452	Intermediate Similarity	NPC93763
0.8444	Intermediate Similarity	NPC32922
0.8391	Intermediate Similarity	NPC131669
0.8391	Intermediate Similarity	NPC473390
0.8391	Intermediate Similarity	NPC40746
0.8391	Intermediate Similarity	NPC169575
0.8391	Intermediate Similarity	NPC39588
0.8387	Intermediate Similarity	NPC52044
0.8387	Intermediate Similarity	NPC170120
0.8372	Intermediate Similarity	NPC39411
0.8372	Intermediate Similarity	NPC255580
0.8372	Intermediate Similarity	NPC24417
0.8353	Intermediate Similarity	NPC182550
0.8333	Intermediate Similarity	NPC7563
0.8333	Intermediate Similarity	NPC15975
0.8333	Intermediate Similarity	NPC470240
0.8333	Intermediate Similarity	NPC195785
0.8333	Intermediate Similarity	NPC150923
0.8333	Intermediate Similarity	NPC320630
0.8333	Intermediate Similarity	NPC476794
0.8333	Intermediate Similarity	NPC116177
0.8315	Intermediate Similarity	NPC236692
0.8315	Intermediate Similarity	NPC309757
0.8315	Intermediate Similarity	NPC150755
0.8313	Intermediate Similarity	NPC193351
0.8313	Intermediate Similarity	NPC226669
0.8313	Intermediate Similarity	NPC138408
0.8295	Intermediate Similarity	NPC476804
0.8295	Intermediate Similarity	NPC472957
0.8295	Intermediate Similarity	NPC472958
0.8295	Intermediate Similarity	NPC156485
0.828	Intermediate Similarity	NPC198853
0.8276	Intermediate Similarity	NPC173609
0.8261	Intermediate Similarity	NPC475925
0.8261	Intermediate Similarity	NPC133698
0.8256	Intermediate Similarity	NPC223904
0.8256	Intermediate Similarity	NPC276356
0.8247	Intermediate Similarity	NPC86077
0.8242	Intermediate Similarity	NPC212664
0.8235	Intermediate Similarity	NPC471465
0.8235	Intermediate Similarity	NPC196653
0.8222	Intermediate Similarity	NPC72513
0.8222	Intermediate Similarity	NPC160138
0.8211	Intermediate Similarity	NPC161493
0.8202	Intermediate Similarity	NPC161957
0.8202	Intermediate Similarity	NPC470755
0.8191	Intermediate Similarity	NPC213698
0.8191	Intermediate Similarity	NPC67584
0.8182	Intermediate Similarity	NPC59097
0.8182	Intermediate Similarity	NPC215294
0.8182	Intermediate Similarity	NPC243998
0.8172	Intermediate Similarity	NPC228451
0.8172	Intermediate Similarity	NPC469692
0.8172	Intermediate Similarity	NPC81419
0.8172	Intermediate Similarity	NPC179746
0.8172	Intermediate Similarity	NPC475302
0.8172	Intermediate Similarity	NPC125674
0.8172	Intermediate Similarity	NPC273579
0.8172	Intermediate Similarity	NPC475912
0.8172	Intermediate Similarity	NPC295204
0.8172	Intermediate Similarity	NPC162205
0.8172	Intermediate Similarity	NPC475838
0.8172	Intermediate Similarity	NPC288240
0.8172	Intermediate Similarity	NPC469645
0.8161	Intermediate Similarity	NPC52861
0.8152	Intermediate Similarity	NPC144133
0.8152	Intermediate Similarity	NPC469368
0.8152	Intermediate Similarity	NPC179394
0.8152	Intermediate Similarity	NPC37607
0.8152	Intermediate Similarity	NPC301969
0.8152	Intermediate Similarity	NPC475855
0.8144	Intermediate Similarity	NPC46998
0.8144	Intermediate Similarity	NPC128733
0.8144	Intermediate Similarity	NPC133907
0.8144	Intermediate Similarity	NPC110443
0.8144	Intermediate Similarity	NPC185141
0.814	Intermediate Similarity	NPC89128
0.814	Intermediate Similarity	NPC264227
0.814	Intermediate Similarity	NPC167881
0.814	Intermediate Similarity	NPC98557
0.814	Intermediate Similarity	NPC472965
0.814	Intermediate Similarity	NPC63649
0.8132	Intermediate Similarity	NPC476805
0.8132	Intermediate Similarity	NPC91248
0.8132	Intermediate Similarity	NPC202672
0.8132	Intermediate Similarity	NPC136879
0.8125	Intermediate Similarity	NPC221615
0.8111	Intermediate Similarity	NPC284902
0.8111	Intermediate Similarity	NPC261721
0.8111	Intermediate Similarity	NPC67493
0.8105	Intermediate Similarity	NPC213078
0.809	Intermediate Similarity	NPC158756
0.8085	Intermediate Similarity	NPC81386
0.8085	Intermediate Similarity	NPC474035
0.8085	Intermediate Similarity	NPC121825
0.8085	Intermediate Similarity	NPC127019
0.8085	Intermediate Similarity	NPC469632
0.8085	Intermediate Similarity	NPC474247
0.8085	Intermediate Similarity	NPC474338
0.8081	Intermediate Similarity	NPC203659
0.8065	Intermediate Similarity	NPC12172
0.8065	Intermediate Similarity	NPC74103
0.8065	Intermediate Similarity	NPC208886
0.8065	Intermediate Similarity	NPC30515
0.8065	Intermediate Similarity	NPC123177
0.8065	Intermediate Similarity	NPC70595
0.8065	Intermediate Similarity	NPC150978
0.8065	Intermediate Similarity	NPC284185
0.8043	Intermediate Similarity	NPC168679
0.8043	Intermediate Similarity	NPC117405
0.8043	Intermediate Similarity	NPC474032
0.8043	Intermediate Similarity	NPC52198
0.8043	Intermediate Similarity	NPC12872
0.8043	Intermediate Similarity	NPC206001
0.8043	Intermediate Similarity	NPC218927
0.8023	Intermediate Similarity	NPC472960
0.8023	Intermediate Similarity	NPC267231
0.8022	Intermediate Similarity	NPC118601
0.8021	Intermediate Similarity	NPC474343
0.8	Intermediate Similarity	NPC14961
0.8	Intermediate Similarity	NPC261380
0.8	Intermediate Similarity	NPC235906
0.8	Intermediate Similarity	NPC223450
0.8	Intermediate Similarity	NPC21469
0.8	Intermediate Similarity	NPC166115
0.8	Intermediate Similarity	NPC21471
0.8	Intermediate Similarity	NPC270013
0.8	Intermediate Similarity	NPC125290
0.8	Intermediate Similarity	NPC36954
0.8	Intermediate Similarity	NPC33570
0.8	Intermediate Similarity	NPC123360
0.798	Intermediate Similarity	NPC110989
0.7978	Intermediate Similarity	NPC250315
0.7978	Intermediate Similarity	NPC318468
0.7976	Intermediate Similarity	NPC114727
0.7976	Intermediate Similarity	NPC476590
0.7976	Intermediate Similarity	NPC476355
0.7976	Intermediate Similarity	NPC472966
0.7959	Intermediate Similarity	NPC171759
0.7957	Intermediate Similarity	NPC474761
0.7957	Intermediate Similarity	NPC476004
0.7957	Intermediate Similarity	NPC62815
0.7957	Intermediate Similarity	NPC51004
0.7957	Intermediate Similarity	NPC253144
0.7955	Intermediate Similarity	NPC141810
0.7955	Intermediate Similarity	NPC325031

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 NPC268298 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1639
0.2-0.3	3751
0.3-0.4	2415
0.4-0.5	767
0.5-0.6	292
0.6-0.7	96
0.7-0.8	20
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
0.8587	High Similarity	NPD1698	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD5785	Approved
0.766	Intermediate Similarity	NPD1695	Approved
0.7609	Intermediate Similarity	NPD5363	Approved
0.7582	Intermediate Similarity	NPD5362	Discontinued
0.7582	Intermediate Similarity	NPD7154	Phase 3
0.7573	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD6371	Approved
0.734	Intermediate Similarity	NPD5786	Approved
0.7283	Intermediate Similarity	NPD4270	Approved
0.7283	Intermediate Similarity	NPD4269	Approved
0.7234	Intermediate Similarity	NPD1694	Approved
0.7234	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6698	Approved
0.7216	Intermediate Similarity	NPD46	Approved
0.7097	Intermediate Similarity	NPD6435	Approved
0.7065	Intermediate Similarity	NPD4252	Approved
0.7065	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4225	Approved
0.7053	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5369	Approved
0.6979	Remote Similarity	NPD4249	Approved
0.6915	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6053	Discontinued
0.6907	Remote Similarity	NPD4250	Approved
0.6907	Remote Similarity	NPD4251	Approved
0.6882	Remote Similarity	NPD4819	Approved
0.6882	Remote Similarity	NPD4822	Approved
0.6882	Remote Similarity	NPD5368	Approved
0.6882	Remote Similarity	NPD4821	Approved
0.6882	Remote Similarity	NPD4820	Approved
0.6869	Remote Similarity	NPD7838	Discovery
0.6848	Remote Similarity	NPD4271	Approved
0.6848	Remote Similarity	NPD4268	Approved
0.6842	Remote Similarity	NPD5331	Approved
0.6842	Remote Similarity	NPD5332	Approved
0.6832	Remote Similarity	NPD5282	Discontinued
0.6809	Remote Similarity	NPD4790	Discontinued
0.68	Remote Similarity	NPD7983	Approved
0.6737	Remote Similarity	NPD5209	Approved
0.6733	Remote Similarity	NPD6399	Phase 3
0.6733	Remote Similarity	NPD5778	Approved
0.6733	Remote Similarity	NPD5779	Approved
0.6731	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6571	Remote Similarity	NPD7638	Approved
0.6559	Remote Similarity	NPD4756	Discovery
0.6545	Remote Similarity	NPD6686	Approved
0.6518	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5697	Approved
0.6437	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5370	Suspended
0.6436	Remote Similarity	NPD6101	Approved
0.6429	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6899	Approved
0.6396	Remote Similarity	NPD6011	Approved
0.6396	Remote Similarity	NPD6881	Approved
0.6396	Remote Similarity	NPD7320	Approved
0.6381	Remote Similarity	NPD7839	Suspended
0.6372	Remote Similarity	NPD6649	Approved
0.6372	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD6675	Approved
0.6364	Remote Similarity	NPD7128	Approved
0.6364	Remote Similarity	NPD6402	Approved
0.6364	Remote Similarity	NPD5739	Approved
0.6339	Remote Similarity	NPD6012	Approved
0.6339	Remote Similarity	NPD6373	Approved
0.6339	Remote Similarity	NPD6014	Approved
0.6339	Remote Similarity	NPD6013	Approved
0.6339	Remote Similarity	NPD6372	Approved
0.6337	Remote Similarity	NPD6903	Approved
0.6321	Remote Similarity	NPD6084	Phase 2
0.6321	Remote Similarity	NPD7902	Approved
0.6321	Remote Similarity	NPD6083	Phase 2
0.6311	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6411	Approved
0.6306	Remote Similarity	NPD5701	Approved
0.63	Remote Similarity	NPD7146	Approved
0.63	Remote Similarity	NPD3618	Phase 1
0.63	Remote Similarity	NPD6409	Approved
0.63	Remote Similarity	NPD7334	Approved
0.63	Remote Similarity	NPD7521	Approved
0.63	Remote Similarity	NPD5330	Approved
0.63	Remote Similarity	NPD6684	Approved
0.6296	Remote Similarity	NPD5344	Discontinued
0.6286	Remote Similarity	NPD5695	Phase 3
0.6283	Remote Similarity	NPD7290	Approved
0.6283	Remote Similarity	NPD6883	Approved
0.6283	Remote Similarity	NPD7102	Approved
0.6263	Remote Similarity	NPD3665	Phase 1
0.6263	Remote Similarity	NPD3666	Approved
0.6263	Remote Similarity	NPD3133	Approved
0.6262	Remote Similarity	NPD5696	Approved
0.6239	Remote Similarity	NPD5211	Phase 2
0.6228	Remote Similarity	NPD6617	Approved
0.6228	Remote Similarity	NPD8130	Phase 1
0.6228	Remote Similarity	NPD6869	Approved
0.6228	Remote Similarity	NPD6847	Approved
0.6224	Remote Similarity	NPD3667	Approved
0.62	Remote Similarity	NPD1696	Phase 3
0.619	Remote Similarity	NPD7748	Approved
0.6182	Remote Similarity	NPD6647	Phase 2
0.618	Remote Similarity	NPD7331	Phase 2
0.6176	Remote Similarity	NPD6672	Approved
0.6176	Remote Similarity	NPD5737	Approved
0.6176	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD8297	Approved
0.6174	Remote Similarity	NPD6882	Approved
0.617	Remote Similarity	NPD8039	Approved
0.6167	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5693	Phase 1
0.6154	Remote Similarity	NPD7637	Suspended
0.6154	Remote Similarity	NPD5281	Approved
0.6154	Remote Similarity	NPD6079	Approved
0.6154	Remote Similarity	NPD5284	Approved
0.6154	Remote Similarity	NPD7515	Phase 2
0.6139	Remote Similarity	NPD5279	Phase 3
0.6132	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5141	Approved
0.6117	Remote Similarity	NPD5328	Approved
0.61	Remote Similarity	NPD4786	Approved
0.6091	Remote Similarity	NPD7632	Discontinued
0.6087	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5221	Approved
0.6075	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5222	Approved
0.6075	Remote Similarity	NPD4697	Phase 3
0.6067	Remote Similarity	NPD7341	Phase 2
0.6061	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5207	Approved
0.6055	Remote Similarity	NPD5286	Approved
0.6055	Remote Similarity	NPD6648	Approved
0.6055	Remote Similarity	NPD5285	Approved
0.6055	Remote Similarity	NPD4696	Approved
0.6038	Remote Similarity	NPD7900	Approved
0.6038	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD8516	Approved
0.6033	Remote Similarity	NPD8517	Approved
0.6033	Remote Similarity	NPD8515	Approved
0.6033	Remote Similarity	NPD8513	Phase 3
0.602	Remote Similarity	NPD4695	Discontinued
0.6019	Remote Similarity	NPD4755	Approved
0.6019	Remote Similarity	NPD5173	Approved
0.6017	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD6110	Phase 1
0.6	Remote Similarity	NPD5223	Approved
0.5984	Remote Similarity	NPD7260	Phase 2
0.5983	Remote Similarity	NPD4632	Approved
0.5981	Remote Similarity	NPD5210	Approved
0.5981	Remote Similarity	NPD4629	Approved
0.598	Remote Similarity	NPD4623	Approved
0.598	Remote Similarity	NPD6422	Discontinued
0.598	Remote Similarity	NPD4519	Discontinued
0.5968	Remote Similarity	NPD7507	Approved
0.5966	Remote Similarity	NPD6317	Approved
0.5962	Remote Similarity	NPD4753	Phase 2
0.5948	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4633	Approved
0.5946	Remote Similarity	NPD5225	Approved
0.5946	Remote Similarity	NPD5224	Approved
0.5946	Remote Similarity	NPD5226	Approved
0.5943	Remote Similarity	NPD4202	Approved
0.5938	Remote Similarity	NPD6845	Suspended
0.5934	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6314	Approved
0.5917	Remote Similarity	NPD6313	Approved
0.5917	Remote Similarity	NPD6335	Approved
0.5913	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4700	Approved
0.5893	Remote Similarity	NPD5174	Approved
0.5893	Remote Similarity	NPD5175	Approved
0.5888	Remote Similarity	NPD6001	Approved
0.5887	Remote Similarity	NPD7492	Approved
0.5882	Remote Similarity	NPD6868	Approved
0.5877	Remote Similarity	NPD6412	Phase 2
0.5868	Remote Similarity	NPD7101	Approved
0.5868	Remote Similarity	NPD7100	Approved
0.5862	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6420	Discontinued
0.5849	Remote Similarity	NPD8035	Phase 2
0.5849	Remote Similarity	NPD8034	Phase 2
0.5843	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.584	Remote Similarity	NPD6616	Approved
0.5833	Remote Similarity	NPD6009	Approved
0.5827	Remote Similarity	NPD7319	Approved
0.5825	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD3704	Approved
0.582	Remote Similarity	NPD6054	Approved
0.582	Remote Similarity	NPD6319	Approved
0.581	Remote Similarity	NPD6673	Approved
0.581	Remote Similarity	NPD6904	Approved
0.581	Remote Similarity	NPD6080	Approved
0.5806	Remote Similarity	NPD7642	Approved
0.5795	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7078	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data