NPASS Compound

Structure

CID257404 OpenBabel06191716062D 25 29 0 0 1 0 0 0 0 0999 V2000 0.8430 -3.3950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5191 -0.4920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6776 -2.9141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5200 -1.4549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0080 -2.9129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6841 -0.0099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3274 -1.9967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4801 -2.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7030 0.9384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8558 0.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 -1.9409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3450 -1.0285 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5328 0.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6504 -1.9663 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0024 -1.9441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8400 -0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5152 -0.5292 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6679 -0.9981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8382 -0.4988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1923 -0.5596 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3801 0.9080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8031 -2.4353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8424 -1.4591 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 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 11 1 0 0 0 0 4 11 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 12 18 1 0 0 0 0 12 21 1 6 0 0 0 13 22 2 0 0 0 0 14 19 1 0 0 0 0 14 23 1 6 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 18 13 1 1 0 0 0 18 19 1 0 0 0 0 19 20 1 6 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.1
Volume:	334.553
LogP:	1.711
LogD:	1.375
LogS:	-3.629
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.72
Synthetic Accessibility Score:	4.86
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.953
MDCK Permeability:	3.240795194869861e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.955
Plasma Protein Binding (PPB):	93.31346893310547%
Volume Distribution (VD):	0.932
Pgp-substrate:	7.150191307067871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.296
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.372
CYP2C19-substrate:	0.274
CYP2C9-inhibitor:	0.457
CYP2C9-substrate:	0.775
CYP2D6-inhibitor:	0.774
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	8.122
Half-life (T1/2):	0.458

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.576
Drug-inuced Liver Injury (DILI):	0.309
AMES Toxicity:	0.868
Rat Oral Acute Toxicity:	0.898
Maximum Recommended Daily Dose:	0.61
Skin Sensitization:	0.146
Carcinogencity:	0.773
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC257404

Natural Product ID:	NPC257404
*Common Name:**	Decaspirone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LLKZNSIXLPVPBZ-JUUKFZBDSA-N
Standard InCHI:	InChI=1S/C20H16O5/c21-12-7-8-14(23)19-18(12)13(22)9-10-20(19)24-15-5-1-3-11-4-2-6-16(25-20)17(11)15/h1-10,12,14,18-19,21,23H/t12-,14+,18-,19+/m0/s1
SMILES:	O[C@@H]1C=C[C@@H]([C@@H]2[C@@H]1C1(C=CC2=O)Oc2cccc3c2c(O1)ccc3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465749
PubChem CID:	16099371
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10923847]
NPO22513	Decaisnella thyridioides	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17190439]
NPO27979	Guatteria friesiana	Species	Annonaceae	Eukaryota	Stems	n.a.	n.a.	PMID[19639965]
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23859780]
NPO27979	Guatteria friesiana	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[27300257]
NPO20220	Coccus citri	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22387	Guettarda speciosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21877	Aplysilla violacea	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22585	Thymus striatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22001	Delphinus longirostris	Species	Delphinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21512	Salvia cardiophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19400	Cussonia natalensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10812	Beaucarnea hookeri	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27979	Guatteria friesiana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23179	Penicillium paraherquei	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22513	Decaisnella thyridioides	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2283	Epichloe uncinata	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20542	Vellozia phalocarpa	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8904	Oreocnide frutescens	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22325	Caesalpinia sepiaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18233	Capparis sepiaria	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21115	Crepidiastrum keiskeanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17178	Labisia pumila	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26602	Ranunculus cantoniensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28371	Echinodontium japonicum	Species	Echinodontiaceae	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
MIC	2
Others	5

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	39.0	mm	PMID[483283]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	41.0	mm	PMID[483283]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	30.0	mm	PMID[483283]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	IZ	=	20.0	mm	PMID[483283]
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	IZ	=	20.0	mm	PMID[483283]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	=	10.0	ug.mL-1	PMID[483283]
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	MIC	=	5.0	ug.mL-1	PMID[483283]

☑ 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 NPC257404 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	357
0.1-0.2	1411
0.2-0.3	3489
0.3-0.4	8291
0.4-0.5	10873
0.5-0.6	3983
0.6-0.7	8679
0.7-0.8	5563
0.8-0.85	26
0.85-0.9	12
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9784	High Similarity	NPC11800
0.9784	High Similarity	NPC206579
0.9638	High Similarity	NPC133585
0.9571	High Similarity	NPC97662
0.9496	High Similarity	NPC197461
0.9118	High Similarity	NPC284232
0.9065	High Similarity	NPC92932
0.8897	High Similarity	NPC47152
0.8767	High Similarity	NPC469408
0.8699	High Similarity	NPC306816
0.8639	High Similarity	NPC473951
0.8582	High Similarity	NPC138940
0.8581	High Similarity	NPC301949
0.8552	High Similarity	NPC473499
0.8483	Intermediate Similarity	NPC193920
0.8481	Intermediate Similarity	NPC472150
0.8452	Intermediate Similarity	NPC472156
0.8365	Intermediate Similarity	NPC175082
0.8344	Intermediate Similarity	NPC73148
0.8288	Intermediate Similarity	NPC472151
0.8217	Intermediate Similarity	NPC193749
0.8199	Intermediate Similarity	NPC63470
0.8148	Intermediate Similarity	NPC472152
0.8141	Intermediate Similarity	NPC267242
0.8113	Intermediate Similarity	NPC472153
0.811	Intermediate Similarity	NPC85368
0.8101	Intermediate Similarity	NPC183402
0.8089	Intermediate Similarity	NPC469507
0.8086	Intermediate Similarity	NPC103633
0.8079	Intermediate Similarity	NPC472154
0.8077	Intermediate Similarity	NPC60084
0.8077	Intermediate Similarity	NPC185103
0.8075	Intermediate Similarity	NPC297404
0.8075	Intermediate Similarity	NPC11608
0.8065	Intermediate Similarity	NPC39819
0.8063	Intermediate Similarity	NPC146837
0.8063	Intermediate Similarity	NPC278329
0.8063	Intermediate Similarity	NPC101116
0.8063	Intermediate Similarity	NPC212099
0.8063	Intermediate Similarity	NPC216752
0.8054	Intermediate Similarity	NPC477537
0.8038	Intermediate Similarity	NPC177742
0.8037	Intermediate Similarity	NPC246274
0.8037	Intermediate Similarity	NPC222455
0.8026	Intermediate Similarity	NPC288531
0.8025	Intermediate Similarity	NPC57141
0.8025	Intermediate Similarity	NPC178173
0.8013	Intermediate Similarity	NPC474843
0.8012	Intermediate Similarity	NPC120677
0.8012	Intermediate Similarity	NPC74371
0.7987	Intermediate Similarity	NPC57072
0.7987	Intermediate Similarity	NPC231475
0.7987	Intermediate Similarity	NPC186113
0.7975	Intermediate Similarity	NPC164244
0.7963	Intermediate Similarity	NPC75944
0.7963	Intermediate Similarity	NPC178281
0.7952	Intermediate Similarity	NPC307754
0.7952	Intermediate Similarity	NPC223735
0.7952	Intermediate Similarity	NPC3718
0.7939	Intermediate Similarity	NPC315619
0.7937	Intermediate Similarity	NPC271479
0.7937	Intermediate Similarity	NPC292863
0.7937	Intermediate Similarity	NPC328093
0.7937	Intermediate Similarity	NPC184326
0.7933	Intermediate Similarity	NPC477535
0.7925	Intermediate Similarity	NPC474441
0.7925	Intermediate Similarity	NPC474398
0.7925	Intermediate Similarity	NPC476026
0.7925	Intermediate Similarity	NPC474401
0.7922	Intermediate Similarity	NPC472339
0.7922	Intermediate Similarity	NPC71055
0.7917	Intermediate Similarity	NPC114257
0.7917	Intermediate Similarity	NPC153578
0.7917	Intermediate Similarity	NPC277710
0.7917	Intermediate Similarity	NPC299149
0.7904	Intermediate Similarity	NPC475246
0.7902	Intermediate Similarity	NPC470841
0.7901	Intermediate Similarity	NPC127415
0.7901	Intermediate Similarity	NPC290160
0.7898	Intermediate Similarity	NPC281272
0.7895	Intermediate Similarity	NPC151704
0.7895	Intermediate Similarity	NPC472155
0.7892	Intermediate Similarity	NPC154986
0.7892	Intermediate Similarity	NPC203751
0.7888	Intermediate Similarity	NPC137232
0.7888	Intermediate Similarity	NPC18380
0.7888	Intermediate Similarity	NPC472157
0.7885	Intermediate Similarity	NPC475890
0.7885	Intermediate Similarity	NPC131874
0.7885	Intermediate Similarity	NPC473966
0.7875	Intermediate Similarity	NPC195167
0.7875	Intermediate Similarity	NPC226287
0.7875	Intermediate Similarity	NPC308265
0.7871	Intermediate Similarity	NPC35150
0.7871	Intermediate Similarity	NPC22137
0.7871	Intermediate Similarity	NPC106328
0.7862	Intermediate Similarity	NPC261866
0.7857	Intermediate Similarity	NPC211565
0.7857	Intermediate Similarity	NPC469758
0.7857	Intermediate Similarity	NPC299011
0.7853	Intermediate Similarity	NPC474591
0.7853	Intermediate Similarity	NPC99216
0.7853	Intermediate Similarity	NPC280923
0.7848	Intermediate Similarity	NPC279281
0.7848	Intermediate Similarity	NPC299761
0.7848	Intermediate Similarity	NPC230439
0.7848	Intermediate Similarity	NPC92153
0.7848	Intermediate Similarity	NPC135522
0.7844	Intermediate Similarity	NPC470667
0.7843	Intermediate Similarity	NPC173630
0.7843	Intermediate Similarity	NPC271076
0.784	Intermediate Similarity	NPC473961
0.784	Intermediate Similarity	NPC56735
0.784	Intermediate Similarity	NPC61594
0.784	Intermediate Similarity	NPC22324
0.7838	Intermediate Similarity	NPC291119
0.7838	Intermediate Similarity	NPC51087
0.7838	Intermediate Similarity	NPC161856
0.7838	Intermediate Similarity	NPC281169
0.7831	Intermediate Similarity	NPC5029
0.7831	Intermediate Similarity	NPC30432
0.7831	Intermediate Similarity	NPC271385
0.7831	Intermediate Similarity	NPC111536
0.7831	Intermediate Similarity	NPC76128
0.7826	Intermediate Similarity	NPC472618
0.7821	Intermediate Similarity	NPC146014
0.7818	Intermediate Similarity	NPC137460
0.7818	Intermediate Similarity	NPC470207
0.7818	Intermediate Similarity	NPC259905
0.7818	Intermediate Similarity	NPC470206
0.7812	Intermediate Similarity	NPC161749
0.7812	Intermediate Similarity	NPC258035
0.7812	Intermediate Similarity	NPC156457
0.7812	Intermediate Similarity	NPC313163
0.7812	Intermediate Similarity	NPC197896
0.7808	Intermediate Similarity	NPC141549
0.7806	Intermediate Similarity	NPC61284
0.7806	Intermediate Similarity	NPC4958
0.7806	Intermediate Similarity	NPC113428
0.7806	Intermediate Similarity	NPC140722
0.7806	Intermediate Similarity	NPC92054
0.7805	Intermediate Similarity	NPC178851
0.7798	Intermediate Similarity	NPC232818
0.7798	Intermediate Similarity	NPC66820
0.7798	Intermediate Similarity	NPC170018
0.7798	Intermediate Similarity	NPC102053
0.7798	Intermediate Similarity	NPC76112
0.7798	Intermediate Similarity	NPC46958
0.7798	Intermediate Similarity	NPC92403
0.7798	Intermediate Similarity	NPC289876
0.7798	Intermediate Similarity	NPC314489
0.7798	Intermediate Similarity	NPC198893
0.7792	Intermediate Similarity	NPC469764
0.7792	Intermediate Similarity	NPC303185
0.7792	Intermediate Similarity	NPC184649
0.7792	Intermediate Similarity	NPC311144
0.7791	Intermediate Similarity	NPC147596
0.7791	Intermediate Similarity	NPC168822
0.7791	Intermediate Similarity	NPC88043
0.7791	Intermediate Similarity	NPC475183
0.7791	Intermediate Similarity	NPC17432
0.7785	Intermediate Similarity	NPC88484
0.7785	Intermediate Similarity	NPC87708
0.7785	Intermediate Similarity	NPC215811
0.7785	Intermediate Similarity	NPC115861
0.7785	Intermediate Similarity	NPC259767
0.7785	Intermediate Similarity	NPC166067
0.7785	Intermediate Similarity	NPC473967
0.7784	Intermediate Similarity	NPC213052
0.7778	Intermediate Similarity	NPC71780
0.7778	Intermediate Similarity	NPC175513
0.7778	Intermediate Similarity	NPC303913
0.7778	Intermediate Similarity	NPC231254
0.7771	Intermediate Similarity	NPC470107
0.7771	Intermediate Similarity	NPC477573
0.7771	Intermediate Similarity	NPC93619
0.7771	Intermediate Similarity	NPC251144
0.7771	Intermediate Similarity	NPC477572
0.7771	Intermediate Similarity	NPC477571
0.7771	Intermediate Similarity	NPC241387
0.7771	Intermediate Similarity	NPC295036
0.7765	Intermediate Similarity	NPC477860
0.7765	Intermediate Similarity	NPC475161
0.7765	Intermediate Similarity	NPC170203
0.7764	Intermediate Similarity	NPC73511
0.7763	Intermediate Similarity	NPC145319
0.7763	Intermediate Similarity	NPC31081
0.7763	Intermediate Similarity	NPC245219
0.7763	Intermediate Similarity	NPC145673
0.7758	Intermediate Similarity	NPC45400
0.7758	Intermediate Similarity	NPC472660
0.7756	Intermediate Similarity	NPC228012
0.7756	Intermediate Similarity	NPC39195
0.7756	Intermediate Similarity	NPC191634
0.7756	Intermediate Similarity	NPC146388
0.7755	Intermediate Similarity	NPC470160
0.775	Intermediate Similarity	NPC309648
0.775	Intermediate Similarity	NPC170475
0.775	Intermediate Similarity	NPC45165
0.7748	Intermediate Similarity	NPC477408

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 NPC257404 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	872
0.2-0.3	1603
0.3-0.4	2578
0.4-0.5	2000
0.5-0.6	1173
0.6-0.7	497
0.7-0.8	118
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
0.8313	Intermediate Similarity	NPD3751	Discontinued
0.8063	Intermediate Similarity	NPD3787	Discontinued
0.8052	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2346	Discontinued
0.7798	Intermediate Similarity	NPD8312	Approved
0.7798	Intermediate Similarity	NPD8313	Approved
0.7688	Intermediate Similarity	NPD5402	Approved
0.7677	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3750	Approved
0.7639	Intermediate Similarity	NPD2797	Approved
0.7625	Intermediate Similarity	NPD7819	Suspended
0.7619	Intermediate Similarity	NPD3268	Approved
0.7605	Intermediate Similarity	NPD7054	Approved
0.7586	Intermediate Similarity	NPD2798	Approved
0.7561	Intermediate Similarity	NPD6959	Discontinued
0.756	Intermediate Similarity	NPD7472	Approved
0.756	Intermediate Similarity	NPD7074	Phase 3
0.7545	Intermediate Similarity	NPD3818	Discontinued
0.7516	Intermediate Similarity	NPD1549	Phase 2
0.7515	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD2313	Discontinued
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7251	Discontinued
0.7471	Intermediate Similarity	NPD6559	Discontinued
0.7468	Intermediate Similarity	NPD5403	Approved
0.7453	Intermediate Similarity	NPD6844	Discontinued
0.7451	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3225	Approved
0.7438	Intermediate Similarity	NPD4380	Phase 2
0.7434	Intermediate Similarity	NPD2799	Discontinued
0.7434	Intermediate Similarity	NPD3748	Approved
0.7427	Intermediate Similarity	NPD7808	Phase 3
0.7427	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1203	Approved
0.7396	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7386	Intermediate Similarity	NPD2935	Discontinued
0.7378	Intermediate Similarity	NPD3749	Approved
0.7375	Intermediate Similarity	NPD3226	Approved
0.7368	Intermediate Similarity	NPD7097	Phase 1
0.7365	Intermediate Similarity	NPD6832	Phase 2
0.7365	Intermediate Similarity	NPD4908	Phase 1
0.7362	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1091	Approved
0.7351	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1933	Approved
0.7346	Intermediate Similarity	NPD37	Approved
0.7346	Intermediate Similarity	NPD1934	Approved
0.7342	Intermediate Similarity	NPD5401	Approved
0.7321	Intermediate Similarity	NPD6166	Phase 2
0.7321	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7033	Discontinued
0.7317	Intermediate Similarity	NPD4965	Approved
0.7317	Intermediate Similarity	NPD4966	Approved
0.7317	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4967	Phase 2
0.7315	Intermediate Similarity	NPD4625	Phase 3
0.7301	Intermediate Similarity	NPD8455	Phase 2
0.7297	Intermediate Similarity	NPD2861	Phase 2
0.7296	Intermediate Similarity	NPD6273	Approved
0.7292	Intermediate Similarity	NPD3496	Discontinued
0.7289	Intermediate Similarity	NPD5494	Approved
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4060	Phase 1
0.7284	Intermediate Similarity	NPD7411	Suspended
0.7279	Intermediate Similarity	NPD3267	Approved
0.7279	Intermediate Similarity	NPD3266	Approved
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD2796	Approved
0.7273	Intermediate Similarity	NPD5585	Approved
0.7273	Intermediate Similarity	NPD6099	Approved
0.7273	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1610	Phase 2
0.7237	Intermediate Similarity	NPD447	Suspended
0.7235	Intermediate Similarity	NPD7228	Approved
0.7233	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7768	Phase 2
0.7208	Intermediate Similarity	NPD1510	Phase 2
0.7205	Intermediate Similarity	NPD1653	Approved
0.7197	Intermediate Similarity	NPD7003	Approved
0.7195	Intermediate Similarity	NPD2801	Approved
0.7195	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD9717	Approved
0.719	Intermediate Similarity	NPD6653	Approved
0.7179	Intermediate Similarity	NPD2424	Discontinued
0.7179	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1613	Approved
0.717	Intermediate Similarity	NPD1511	Approved
0.7169	Intermediate Similarity	NPD7075	Discontinued
0.716	Intermediate Similarity	NPD7458	Discontinued
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD4749	Approved
0.7134	Intermediate Similarity	NPD6674	Discontinued
0.7126	Intermediate Similarity	NPD6234	Discontinued
0.7124	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5124	Phase 1
0.7124	Intermediate Similarity	NPD6355	Discontinued
0.7115	Intermediate Similarity	NPD2344	Approved
0.7114	Intermediate Similarity	NPD5647	Approved
0.711	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3882	Suspended
0.7097	Intermediate Similarity	NPD4308	Phase 3
0.7091	Intermediate Similarity	NPD1465	Phase 2
0.7081	Intermediate Similarity	NPD1512	Approved
0.7076	Intermediate Similarity	NPD7473	Discontinued
0.7063	Intermediate Similarity	NPD6799	Approved
0.7062	Intermediate Similarity	NPD8150	Discontinued
0.7059	Intermediate Similarity	NPD4140	Approved
0.7051	Intermediate Similarity	NPD6032	Approved
0.7048	Intermediate Similarity	NPD3817	Phase 2
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.7039	Intermediate Similarity	NPD411	Approved
0.703	Intermediate Similarity	NPD6801	Discontinued
0.7027	Intermediate Similarity	NPD4359	Approved
0.7025	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6778	Approved
0.7011	Intermediate Similarity	NPD6782	Approved
0.7011	Intermediate Similarity	NPD6780	Approved
0.7011	Intermediate Similarity	NPD6777	Approved
0.7011	Intermediate Similarity	NPD6776	Approved
0.7011	Intermediate Similarity	NPD6779	Approved
0.7011	Intermediate Similarity	NPD6781	Approved
0.7007	Intermediate Similarity	NPD1611	Approved
0.7006	Intermediate Similarity	NPD7266	Discontinued
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD7229	Phase 3
0.6993	Remote Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD6671	Approved
0.6993	Remote Similarity	NPD709	Approved
0.6987	Remote Similarity	NPD4108	Discontinued
0.6986	Remote Similarity	NPD1778	Approved
0.6986	Remote Similarity	NPD4626	Approved
0.6981	Remote Similarity	NPD4628	Phase 3
0.698	Remote Similarity	NPD1283	Approved
0.6972	Remote Similarity	NPD1241	Discontinued
0.6971	Remote Similarity	NPD7240	Approved
0.697	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1548	Phase 1
0.6959	Remote Similarity	NPD1608	Approved
0.6959	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2235	Phase 2
0.6959	Remote Similarity	NPD2231	Phase 2
0.6951	Remote Similarity	NPD2649	Approved
0.6951	Remote Similarity	NPD2651	Approved
0.6948	Remote Similarity	NPD2979	Phase 3
0.6948	Remote Similarity	NPD1240	Approved
0.6944	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2309	Approved
0.6935	Remote Similarity	NPD6823	Phase 2
0.6933	Remote Similarity	NPD6362	Approved
0.6933	Remote Similarity	NPD1470	Approved
0.6923	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5691	Approved
0.6918	Remote Similarity	NPD1651	Approved
0.6914	Remote Similarity	NPD2533	Approved
0.6914	Remote Similarity	NPD2532	Approved
0.6914	Remote Similarity	NPD2534	Approved
0.6913	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.691	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6599	Discontinued
0.6909	Remote Similarity	NPD7028	Phase 2
0.6908	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4622	Approved
0.6903	Remote Similarity	NPD4618	Approved
0.6899	Remote Similarity	NPD6004	Phase 3
0.6899	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6005	Phase 3
0.6899	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6002	Phase 3
0.6898	Remote Similarity	NPD7435	Discontinued
0.6898	Remote Similarity	NPD7698	Approved
0.6898	Remote Similarity	NPD7697	Approved
0.6898	Remote Similarity	NPD7696	Phase 3
0.6887	Remote Similarity	NPD1019	Discontinued
0.6887	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4870	Approved
0.6875	Remote Similarity	NPD3892	Phase 2
0.6875	Remote Similarity	NPD8166	Discontinued
0.6863	Remote Similarity	NPD7095	Approved
0.6862	Remote Similarity	NPD7870	Phase 2
0.6862	Remote Similarity	NPD7871	Phase 2
0.6859	Remote Similarity	NPD1607	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