NPASS Compound

Structure

CID80875 OpenBabel06191715422D 26 28 0 0 1 0 0 0 0 0999 V2000 -3.5604 -3.6946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4014 -4.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2257 -2.8452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1160 -1.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6970 -2.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0854 -1.3404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7957 -1.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2782 -1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6093 -4.0036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 -1.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1970 -1.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3309 -1.6872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5823 -1.1226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4538 -0.5181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8662 -3.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4483 -0.6226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9151 -3.6435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4265 -0.4147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3693 -0.6424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0741 -2.3563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -0.2091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 23 1 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 6 0 0 0 15 13 1 1 0 0 0 15 17 1 0 0 0 0 16 12 1 6 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 25 1 6 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 20 23 1 6 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.16
Volume:	365.729
LogP:	2.488
LogD:	2.661
LogS:	-3.878
# Rotatable Bonds:	4
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	6.124
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.637
MDCK Permeability:	4.927557893097401e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.263
20% Bioavailability (F20%):	0.141
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.547
Plasma Protein Binding (PPB):	75.52021026611328%
Volume Distribution (VD):	1.933
Pgp-substrate:	25.097347259521484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.086
CYP1A2-substrate:	0.443
CYP2C19-inhibitor:	0.226
CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.653
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.636
CYP3A4-substrate:	0.352

ADMET: Excretion

Clearance (CL):	13.646
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.743
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.907
Maximum Recommended Daily Dose:	0.132
Skin Sensitization:	0.71
Carcinogencity:	0.164
Eye Corrosion:	0.454
Eye Irritation:	0.208
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC80875

Natural Product ID:	NPC80875
*Common Name:**	CSIBMGLPBAXXSG-MKOUKINSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CSIBMGLPBAXXSG-MKOUKINSSA-N
Standard InCHI:	InChI=1S/C20H24O6/c1-10(2)18(21)24-14-7-11(3)8-20(23-6)9-12(4)16(26-20)17-15(14)13(5)19(22)25-17/h8-9,14-17H,1,5,7H2,2-4,6H3/b11-8-/t14-,15+,16-,17-,20-/m0/s1
SMILES:	C=C(C)C(=O)O[C@H]1C/C(=C[C@]2(C=C(C)[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)O2)OC)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2368404
PubChem CID:	73354392
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075766]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[18239317]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[18239317]
NPO3141	Saracha punctata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834160]
NPO7088	Staphylea bumalda	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7088	Staphylea bumalda	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7088	Staphylea bumalda	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4439	Epaltes mexicana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8855	Fromia milleporella	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7088	Staphylea bumalda	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24759	Schotia brachypetala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6503	Marsdenia rostrata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7641	Petunia hybr	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3325	Cineraria parvifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7278	Astragalus caprinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5586	Kickxia elatine	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12443	Torrubiella hemipterigena	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4881	Senecio kilimanjari	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4076	Lubomirskia baicalensis	Species	Lubomirskiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8580	Caloplaca ferruginea	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5991	Arcopilus aureus	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5318	Rotheca serrata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5195	Odontites vernus	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3141	Saracha punctata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4618	Ilex oldhami	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO343	Cryptosphaeria eunomia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3657	Hyalis argentea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO171	Relbunium hypocarpium	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5789	Ocotea acutangula	Species	Lauraceae	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
Others	3

Activity Type	# Activity
Individual Protein	1
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	10.0	uM	PMID[544020]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	pIC100	=	-1.0	n.a.	PMID[544020]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	10.0	uM	PMID[544021]

☑ 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 NPC80875 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	235
0.1-0.2	1535
0.2-0.3	5700
0.3-0.4	12573
0.4-0.5	12293
0.5-0.6	6970
0.6-0.7	2577
0.7-0.8	757
0.8-0.85	55
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8817	High Similarity	NPC279561
0.8587	High Similarity	NPC473316
0.8587	High Similarity	NPC473330
0.8539	High Similarity	NPC231889
0.8462	Intermediate Similarity	NPC475748
0.8427	Intermediate Similarity	NPC284902
0.8421	Intermediate Similarity	NPC187268
0.8387	Intermediate Similarity	NPC474338
0.8352	Intermediate Similarity	NPC151770
0.8333	Intermediate Similarity	NPC475703
0.828	Intermediate Similarity	NPC81419
0.828	Intermediate Similarity	NPC179746
0.828	Intermediate Similarity	NPC475912
0.828	Intermediate Similarity	NPC476300
0.8261	Intermediate Similarity	NPC51004
0.8261	Intermediate Similarity	NPC473619
0.8191	Intermediate Similarity	NPC140543
0.8191	Intermediate Similarity	NPC471147
0.8172	Intermediate Similarity	NPC12172
0.8172	Intermediate Similarity	NPC473321
0.8172	Intermediate Similarity	NPC184463
0.8172	Intermediate Similarity	NPC208886
0.8172	Intermediate Similarity	NPC30515
0.8152	Intermediate Similarity	NPC307411
0.8152	Intermediate Similarity	NPC295312
0.8152	Intermediate Similarity	NPC474032
0.8152	Intermediate Similarity	NPC166919
0.8125	Intermediate Similarity	NPC471462
0.8118	Intermediate Similarity	NPC123360
0.8111	Intermediate Similarity	NPC21469
0.8111	Intermediate Similarity	NPC50362
0.8111	Intermediate Similarity	NPC38468
0.8111	Intermediate Similarity	NPC319795
0.8105	Intermediate Similarity	NPC475659
0.8105	Intermediate Similarity	NPC270013
0.8105	Intermediate Similarity	NPC14961
0.8105	Intermediate Similarity	NPC36954
0.809	Intermediate Similarity	NPC170286
0.809	Intermediate Similarity	NPC475947
0.809	Intermediate Similarity	NPC272814
0.8085	Intermediate Similarity	NPC295204
0.8085	Intermediate Similarity	NPC273579
0.8085	Intermediate Similarity	NPC288240
0.8085	Intermediate Similarity	NPC162205
0.8085	Intermediate Similarity	NPC212486
0.8065	Intermediate Similarity	NPC312042
0.8043	Intermediate Similarity	NPC473715
0.8043	Intermediate Similarity	NPC202672
0.8041	Intermediate Similarity	NPC208233
0.8041	Intermediate Similarity	NPC473326
0.8023	Intermediate Similarity	NPC476028
0.8023	Intermediate Similarity	NPC141789
0.8023	Intermediate Similarity	NPC97516
0.8023	Intermediate Similarity	NPC171204
0.8022	Intermediate Similarity	NPC50637
0.8022	Intermediate Similarity	NPC112685
0.8021	Intermediate Similarity	NPC306041
0.8021	Intermediate Similarity	NPC473859
0.8021	Intermediate Similarity	NPC35498
0.8021	Intermediate Similarity	NPC301596
0.8021	Intermediate Similarity	NPC476315
0.8021	Intermediate Similarity	NPC299396
0.8	Intermediate Similarity	NPC81386
0.8	Intermediate Similarity	NPC303942
0.8	Intermediate Similarity	NPC57405
0.8	Intermediate Similarity	NPC476267
0.8	Intermediate Similarity	NPC474035
0.7979	Intermediate Similarity	NPC470373
0.7979	Intermediate Similarity	NPC473707
0.7979	Intermediate Similarity	NPC470379
0.7978	Intermediate Similarity	NPC173609
0.7959	Intermediate Similarity	NPC469402
0.7957	Intermediate Similarity	NPC477011
0.7917	Intermediate Similarity	NPC477922
0.7917	Intermediate Similarity	NPC471141
0.7917	Intermediate Similarity	NPC471142
0.7912	Intermediate Similarity	NPC215364
0.7895	Intermediate Similarity	NPC11456
0.7895	Intermediate Similarity	NPC473663
0.7895	Intermediate Similarity	NPC475173
0.7895	Intermediate Similarity	NPC473723
0.7895	Intermediate Similarity	NPC473561
0.7889	Intermediate Similarity	NPC318468
0.7882	Intermediate Similarity	NPC476355
0.7882	Intermediate Similarity	NPC140287
0.7872	Intermediate Similarity	NPC49342
0.7872	Intermediate Similarity	NPC206614
0.7872	Intermediate Similarity	NPC251385
0.7872	Intermediate Similarity	NPC473904
0.7872	Intermediate Similarity	NPC476004
0.7872	Intermediate Similarity	NPC474323
0.7872	Intermediate Similarity	NPC474761
0.7865	Intermediate Similarity	NPC301477
0.7865	Intermediate Similarity	NPC25684
0.7865	Intermediate Similarity	NPC141810
0.7865	Intermediate Similarity	NPC281949
0.7864	Intermediate Similarity	NPC38154
0.7857	Intermediate Similarity	NPC163003
0.7849	Intermediate Similarity	NPC280621
0.7849	Intermediate Similarity	NPC48338
0.7849	Intermediate Similarity	NPC233551
0.7849	Intermediate Similarity	NPC89001
0.7849	Intermediate Similarity	NPC21208
0.7849	Intermediate Similarity	NPC20339
0.7849	Intermediate Similarity	NPC40376
0.7841	Intermediate Similarity	NPC270126
0.7835	Intermediate Similarity	NPC17585
0.7835	Intermediate Similarity	NPC172998
0.7835	Intermediate Similarity	NPC477921
0.7826	Intermediate Similarity	NPC231096
0.7826	Intermediate Similarity	NPC162071
0.7826	Intermediate Similarity	NPC114694
0.7826	Intermediate Similarity	NPC142117
0.7826	Intermediate Similarity	NPC475581
0.7826	Intermediate Similarity	NPC62118
0.7826	Intermediate Similarity	NPC171174
0.7826	Intermediate Similarity	NPC107717
0.7826	Intermediate Similarity	NPC232555
0.7826	Intermediate Similarity	NPC240695
0.7822	Intermediate Similarity	NPC305157
0.7822	Intermediate Similarity	NPC307846
0.7812	Intermediate Similarity	NPC71589
0.7789	Intermediate Similarity	NPC20713
0.7778	Intermediate Similarity	NPC288876
0.7767	Intermediate Similarity	NPC475960
0.7766	Intermediate Similarity	NPC139418
0.7766	Intermediate Similarity	NPC280612
0.7766	Intermediate Similarity	NPC473564
0.7766	Intermediate Similarity	NPC477016
0.7766	Intermediate Similarity	NPC477017
0.7753	Intermediate Similarity	NPC281132
0.7745	Intermediate Similarity	NPC469401
0.7742	Intermediate Similarity	NPC160138
0.7742	Intermediate Similarity	NPC5130
0.7742	Intermediate Similarity	NPC186148
0.7742	Intermediate Similarity	NPC178215
0.7732	Intermediate Similarity	NPC273197
0.7732	Intermediate Similarity	NPC224689
0.7732	Intermediate Similarity	NPC234339
0.7717	Intermediate Similarity	NPC82795
0.7717	Intermediate Similarity	NPC66346
0.7717	Intermediate Similarity	NPC283085
0.7717	Intermediate Similarity	NPC477018
0.7717	Intermediate Similarity	NPC473669
0.7717	Intermediate Similarity	NPC286338
0.7717	Intermediate Similarity	NPC99395
0.7717	Intermediate Similarity	NPC100921
0.7717	Intermediate Similarity	NPC107986
0.7717	Intermediate Similarity	NPC120398
0.7717	Intermediate Similarity	NPC471567
0.7717	Intermediate Similarity	NPC231009
0.7717	Intermediate Similarity	NPC197903
0.7717	Intermediate Similarity	NPC473478
0.7717	Intermediate Similarity	NPC473651
0.7717	Intermediate Similarity	NPC223871
0.7717	Intermediate Similarity	NPC110710
0.7717	Intermediate Similarity	NPC132496
0.7717	Intermediate Similarity	NPC103284
0.7717	Intermediate Similarity	NPC1083
0.77	Intermediate Similarity	NPC477511
0.77	Intermediate Similarity	NPC473332
0.77	Intermediate Similarity	NPC264477
0.7684	Intermediate Similarity	NPC469718
0.7684	Intermediate Similarity	NPC239517
0.7684	Intermediate Similarity	NPC62815
0.7684	Intermediate Similarity	NPC329857
0.7677	Intermediate Similarity	NPC471144
0.7667	Intermediate Similarity	NPC471325
0.766	Intermediate Similarity	NPC242364
0.766	Intermediate Similarity	NPC274446
0.766	Intermediate Similarity	NPC320569
0.766	Intermediate Similarity	NPC81045
0.766	Intermediate Similarity	NPC191929
0.766	Intermediate Similarity	NPC169511
0.766	Intermediate Similarity	NPC39754
0.766	Intermediate Similarity	NPC234077
0.766	Intermediate Similarity	NPC172821
0.766	Intermediate Similarity	NPC133730
0.766	Intermediate Similarity	NPC171135
0.766	Intermediate Similarity	NPC177629
0.766	Intermediate Similarity	NPC100454
0.766	Intermediate Similarity	NPC287164
0.766	Intermediate Similarity	NPC61257
0.766	Intermediate Similarity	NPC261952
0.766	Intermediate Similarity	NPC151403
0.766	Intermediate Similarity	NPC58219
0.7653	Intermediate Similarity	NPC279621
0.7647	Intermediate Similarity	NPC100487
0.7647	Intermediate Similarity	NPC203659
0.764	Intermediate Similarity	NPC178277
0.764	Intermediate Similarity	NPC617
0.7634	Intermediate Similarity	NPC309211
0.7634	Intermediate Similarity	NPC134865
0.7634	Intermediate Similarity	NPC473687
0.7634	Intermediate Similarity	NPC134885
0.7634	Intermediate Similarity	NPC107787
0.7634	Intermediate Similarity	NPC134807
0.7634	Intermediate Similarity	NPC308412
0.7634	Intermediate Similarity	NPC219498
0.7634	Intermediate Similarity	NPC69082

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 NPC80875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	2144
0.2-0.3	3906
0.3-0.4	1992
0.4-0.5	641
0.5-0.6	205
0.6-0.7	47
0.7-0.8	3
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
0.8111	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1695	Approved
0.732	Intermediate Similarity	NPD46	Approved
0.732	Intermediate Similarity	NPD6698	Approved
0.717	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6686	Approved
0.7071	Intermediate Similarity	NPD7983	Approved
0.703	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7838	Discovery
0.6735	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6476	Remote Similarity	NPD7839	Suspended
0.6465	Remote Similarity	NPD1694	Approved
0.6446	Remote Similarity	NPD7507	Approved
0.6429	Remote Similarity	NPD7154	Phase 3
0.6404	Remote Similarity	NPD6053	Discontinued
0.6393	Remote Similarity	NPD8074	Phase 3
0.6355	Remote Similarity	NPD4225	Approved
0.6346	Remote Similarity	NPD5778	Approved
0.6346	Remote Similarity	NPD5779	Approved
0.6327	Remote Similarity	NPD6435	Approved
0.6327	Remote Similarity	NPD5209	Approved
0.6311	Remote Similarity	NPD5785	Approved
0.6306	Remote Similarity	NPD6008	Approved
0.63	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7319	Approved
0.6289	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5282	Discontinued
0.6281	Remote Similarity	NPD7830	Approved
0.6281	Remote Similarity	NPD7642	Approved
0.6281	Remote Similarity	NPD7829	Approved
0.6271	Remote Similarity	NPD7641	Discontinued
0.6263	Remote Similarity	NPD5362	Discontinued
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5786	Approved
0.618	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6648	Approved
0.6139	Remote Similarity	NPD5363	Approved
0.6122	Remote Similarity	NPD5368	Approved
0.6116	Remote Similarity	NPD8444	Approved
0.6105	Remote Similarity	NPD8039	Approved
0.6098	Remote Similarity	NPD7492	Approved
0.6091	Remote Similarity	NPD5344	Discontinued
0.6087	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4271	Approved
0.6082	Remote Similarity	NPD4268	Approved
0.6077	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8451	Approved
0.6048	Remote Similarity	NPD6616	Approved
0.604	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD2204	Approved
0.6033	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7078	Approved
0.5984	Remote Similarity	NPD6015	Approved
0.5984	Remote Similarity	NPD6016	Approved
0.5965	Remote Similarity	NPD6412	Phase 2
0.596	Remote Similarity	NPD4819	Approved
0.596	Remote Similarity	NPD4820	Approved
0.596	Remote Similarity	NPD4252	Approved
0.596	Remote Similarity	NPD4822	Approved
0.596	Remote Similarity	NPD4821	Approved
0.5952	Remote Similarity	NPD7736	Approved
0.5948	Remote Similarity	NPD2067	Discontinued
0.5935	Remote Similarity	NPD6370	Approved
0.5935	Remote Similarity	NPD5988	Approved
0.5922	Remote Similarity	NPD6422	Discontinued
0.5917	Remote Similarity	NPD6009	Approved
0.5909	Remote Similarity	NPD7638	Approved
0.5905	Remote Similarity	NPD6101	Approved
0.5905	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6059	Approved
0.59	Remote Similarity	NPD5369	Approved
0.5873	Remote Similarity	NPD8293	Discontinued
0.5868	Remote Similarity	NPD7327	Approved
0.5868	Remote Similarity	NPD7328	Approved
0.5859	Remote Similarity	NPD8390	Approved
0.5859	Remote Similarity	NPD8392	Approved
0.5859	Remote Similarity	NPD8391	Approved
0.5856	Remote Similarity	NPD7639	Approved
0.5856	Remote Similarity	NPD7640	Approved
0.5854	Remote Similarity	NPD8268	Approved
0.5854	Remote Similarity	NPD8269	Approved
0.5854	Remote Similarity	NPD8033	Approved
0.5854	Remote Similarity	NPD8266	Approved
0.5854	Remote Similarity	NPD8267	Approved
0.584	Remote Similarity	NPD8341	Approved
0.584	Remote Similarity	NPD8340	Approved
0.584	Remote Similarity	NPD8342	Approved
0.584	Remote Similarity	NPD8299	Approved
0.582	Remote Similarity	NPD7516	Approved
0.5814	Remote Similarity	NPD7260	Phase 2
0.5794	Remote Similarity	NPD6411	Approved
0.5785	Remote Similarity	NPD7115	Discovery
0.5785	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7500	Approved
0.5784	Remote Similarity	NPD5331	Approved
0.5784	Remote Similarity	NPD6110	Phase 1
0.5784	Remote Similarity	NPD5332	Approved
0.5772	Remote Similarity	NPD8294	Approved
0.5772	Remote Similarity	NPD8377	Approved
0.5769	Remote Similarity	NPD6845	Suspended
0.576	Remote Similarity	NPD8328	Phase 3
0.5758	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4790	Discontinued
0.5741	Remote Similarity	NPD6399	Phase 3
0.5726	Remote Similarity	NPD8378	Approved
0.5726	Remote Similarity	NPD8379	Approved
0.5726	Remote Similarity	NPD8335	Approved
0.5726	Remote Similarity	NPD8380	Approved
0.5726	Remote Similarity	NPD8296	Approved
0.5714	Remote Similarity	NPD6882	Approved
0.5703	Remote Similarity	NPD8336	Approved
0.5703	Remote Similarity	NPD8337	Approved
0.5699	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.568	Remote Similarity	NPD8080	Discontinued
0.5667	Remote Similarity	NPD8133	Approved
0.5667	Remote Similarity	NPD4632	Approved
0.566	Remote Similarity	NPD6903	Approved
0.5657	Remote Similarity	NPD4756	Discovery
0.5656	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD7637	Suspended
0.5645	Remote Similarity	NPD6319	Approved
0.5641	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD5330	Approved
0.5619	Remote Similarity	NPD7521	Approved
0.5619	Remote Similarity	NPD7334	Approved
0.5619	Remote Similarity	NPD7146	Approved
0.5619	Remote Similarity	NPD6684	Approved
0.5619	Remote Similarity	NPD6409	Approved
0.5607	Remote Similarity	NPD5370	Suspended
0.56	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7503	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