NPASS Compound

Structure

CID205765 OpenBabel06191715592D 28 31 0 0 1 0 0 0 0 0999 V2000 -2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7516 -0.0286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6176 -0.5286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4152 -1.6113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 -0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0303 -0.4898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0685 1.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3612 -1.2330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4097 -1.5068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 19 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 22 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 28 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 28 1 0 0 0 0 16 23 1 0 0 0 0 16 26 2 0 0 0 0 17 18 1 0 0 0 0 18 27 1 1 0 0 0 19 22 1 0 0 0 0 19 24 1 1 0 0 0 20 23 1 1 0 0 0 20 25 1 0 0 0 0 21 24 1 1 0 0 0 21 25 1 0 0 0 0 23 3 1 1 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.28
Volume:	425.192
LogP:	4.872
LogD:	4.577
LogS:	-4.448
# Rotatable Bonds:	4
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	4.834
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.839
MDCK Permeability:	1.6210624380619265e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.913
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.958
Plasma Protein Binding (PPB):	80.71231842041016%
Volume Distribution (VD):	1.8
Pgp-substrate:	13.68057918548584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.212
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.63
CYP2C9-inhibitor:	0.273
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.828
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.935
CYP3A4-substrate:	0.513

ADMET: Excretion

Clearance (CL):	13.607
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.689
Carcinogencity:	0.805
Eye Corrosion:	0.923
Eye Irritation:	0.781
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC205765

Natural Product ID:	NPC205765
*Common Name:**	Hyrtiosal
IUPAC Name:	(2S,3S,3aR,5aS,9aS,9bR)-3-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-3,4,5,5a,7,8,9,9b-octahydro-1H-cyclopenta[a]naphthalene-2-carbaldehyde
Synonyms:	Hyrtiosal
Standard InCHIKey:	PUTJFIQGLGDLIT-RNDOZLNUSA-N
Standard InCHI:	InChI=1S/C25H38O3/c1-22(2)9-6-10-24(4)19(22)7-11-25(5)20(23(3,16-26)14-21(24)25)13-18(27)17-8-12-28-15-17/h8,12,15-16,18-21,27H,6-7,9-11,13-14H2,1-5H3/t18-,19-,20+,21+,23+,24-,25-/m0/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@]1(C)[C@H](C[C@@H](c3ccoc3)O)[C@](C)(C[C@H]21)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078661
PubChem CID:	11361184
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001565] Iridoids and derivatives

*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
NPO4034	Albizia adinocephala	Species	Fabaceae	Eukaryota	Stem bark and leaves	n.a.	n.a.	PMID[19299148]
NPO670	Hyrtios gumminae	Species	Thorectidae	Eukaryota	n.a.	Thai	n.a.	PMID[19788270]
NPO4034	Albizia adinocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5186	Pimpinella aurea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO670	Hyrtios gumminae	Species	Thorectidae	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
IC50	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	7800.0	nM	PMID[475779]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	18000.0	nM	PMID[475779]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	5400.0	nM	PMID[475779]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	9100.0	nM	PMID[475779]
NPT1396	Cell Line	NCI-H69	Homo sapiens	IC50	=	31000.0	nM	PMID[475779]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9100.0	nM	PMID[475779]

☑ 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 NPC205765 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	320
0.1-0.2	1223
0.2-0.3	2644
0.3-0.4	5736
0.4-0.5	12453
0.5-0.6	10211
0.6-0.7	9004
0.7-0.8	854
0.8-0.85	210
0.85-0.9	36
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9078	High Similarity	NPC476944
0.9028	High Similarity	NPC472654
0.9007	High Similarity	NPC476946
0.8926	High Similarity	NPC116639
0.8897	High Similarity	NPC470998
0.8889	High Similarity	NPC250228
0.8873	High Similarity	NPC267632
0.8819	High Similarity	NPC346
0.8786	High Similarity	NPC476943
0.8767	High Similarity	NPC195325
0.875	High Similarity	NPC185456
0.8731	High Similarity	NPC23086
0.8716	High Similarity	NPC33938
0.8714	High Similarity	NPC310830
0.8707	High Similarity	NPC470997
0.8693	High Similarity	NPC261184
0.8686	High Similarity	NPC61788
0.8671	High Similarity	NPC62103
0.8671	High Similarity	NPC20578
0.8662	High Similarity	NPC67003
0.8643	High Similarity	NPC46896
0.863	High Similarity	NPC302987
0.86	High Similarity	NPC35000
0.8592	High Similarity	NPC90953
0.8591	High Similarity	NPC469503
0.8591	High Similarity	NPC75906
0.8571	High Similarity	NPC158525
0.8571	High Similarity	NPC92941
0.8571	High Similarity	NPC476947
0.8561	High Similarity	NPC214097
0.8552	High Similarity	NPC142113
0.8533	High Similarity	NPC282445
0.8533	High Similarity	NPC178932
0.8533	High Similarity	NPC30222
0.8521	High Similarity	NPC220094
0.8521	High Similarity	NPC472376
0.8514	High Similarity	NPC234494
0.8506	High Similarity	NPC663
0.8506	High Similarity	NPC224394
0.8503	High Similarity	NPC471174
0.8503	High Similarity	NPC216755
0.8493	Intermediate Similarity	NPC5676
0.8483	Intermediate Similarity	NPC243577
0.8477	Intermediate Similarity	NPC281258
0.8477	Intermediate Similarity	NPC469336
0.8467	Intermediate Similarity	NPC470996
0.8467	Intermediate Similarity	NPC112706
0.8467	Intermediate Similarity	NPC207294
0.8456	Intermediate Similarity	NPC156189
0.8456	Intermediate Similarity	NPC196846
0.8456	Intermediate Similarity	NPC138139
0.8456	Intermediate Similarity	NPC46536
0.8451	Intermediate Similarity	NPC470742
0.8446	Intermediate Similarity	NPC476942
0.8446	Intermediate Similarity	NPC476941
0.8442	Intermediate Similarity	NPC472767
0.8433	Intermediate Similarity	NPC263870
0.8433	Intermediate Similarity	NPC477967
0.8431	Intermediate Similarity	NPC475226
0.8429	Intermediate Similarity	NPC471006
0.8429	Intermediate Similarity	NPC218838
0.8425	Intermediate Similarity	NPC251865
0.8417	Intermediate Similarity	NPC89133
0.8414	Intermediate Similarity	NPC52412
0.8414	Intermediate Similarity	NPC121158
0.8411	Intermediate Similarity	NPC57998
0.8403	Intermediate Similarity	NPC56197
0.8397	Intermediate Similarity	NPC214600
0.8389	Intermediate Similarity	NPC470790
0.8389	Intermediate Similarity	NPC470791
0.8387	Intermediate Similarity	NPC165218
0.8378	Intermediate Similarity	NPC476937
0.8378	Intermediate Similarity	NPC221809
0.8378	Intermediate Similarity	NPC476938
0.8377	Intermediate Similarity	NPC470789
0.8369	Intermediate Similarity	NPC471998
0.8367	Intermediate Similarity	NPC41182
0.8366	Intermediate Similarity	NPC472772
0.8366	Intermediate Similarity	NPC249021
0.8356	Intermediate Similarity	NPC470741
0.8356	Intermediate Similarity	NPC64568
0.8356	Intermediate Similarity	NPC223415
0.8355	Intermediate Similarity	NPC92979
0.8345	Intermediate Similarity	NPC20500
0.8333	Intermediate Similarity	NPC477040
0.8323	Intermediate Similarity	NPC470792
0.8323	Intermediate Similarity	NPC200782
0.8322	Intermediate Similarity	NPC4764
0.8322	Intermediate Similarity	NPC186626
0.8322	Intermediate Similarity	NPC471007
0.8313	Intermediate Similarity	NPC471437
0.8312	Intermediate Similarity	NPC474611
0.8312	Intermediate Similarity	NPC475967
0.8311	Intermediate Similarity	NPC262198
0.8311	Intermediate Similarity	NPC471292
0.8299	Intermediate Similarity	NPC199044
0.8299	Intermediate Similarity	NPC238843
0.8288	Intermediate Similarity	NPC473152
0.828	Intermediate Similarity	NPC149945
0.828	Intermediate Similarity	NPC478178
0.8278	Intermediate Similarity	NPC472787
0.8278	Intermediate Similarity	NPC272590
0.8278	Intermediate Similarity	NPC18135
0.8267	Intermediate Similarity	NPC125182
0.8267	Intermediate Similarity	NPC69647
0.8267	Intermediate Similarity	NPC329180
0.8261	Intermediate Similarity	NPC319140
0.8261	Intermediate Similarity	NPC290955
0.8261	Intermediate Similarity	NPC95567
0.8261	Intermediate Similarity	NPC83178
0.8258	Intermediate Similarity	NPC477402
0.8258	Intermediate Similarity	NPC335761
0.8255	Intermediate Similarity	NPC470941
0.8255	Intermediate Similarity	NPC255414
0.8252	Intermediate Similarity	NPC146872
0.8248	Intermediate Similarity	NPC179354
0.8248	Intermediate Similarity	NPC303010
0.8247	Intermediate Similarity	NPC261597
0.8247	Intermediate Similarity	NPC299038
0.8247	Intermediate Similarity	NPC472778
0.8247	Intermediate Similarity	NPC45101
0.8247	Intermediate Similarity	NPC472777
0.8247	Intermediate Similarity	NPC472776
0.8235	Intermediate Similarity	NPC214541
0.8235	Intermediate Similarity	NPC155939
0.8235	Intermediate Similarity	NPC44675
0.8235	Intermediate Similarity	NPC264943
0.8235	Intermediate Similarity	NPC272899
0.8235	Intermediate Similarity	NPC16922
0.8235	Intermediate Similarity	NPC296807
0.8235	Intermediate Similarity	NPC141538
0.8231	Intermediate Similarity	NPC103134
0.8228	Intermediate Similarity	NPC478179
0.8228	Intermediate Similarity	NPC472764
0.8227	Intermediate Similarity	NPC471995
0.8224	Intermediate Similarity	NPC246164
0.8224	Intermediate Similarity	NPC44577
0.8224	Intermediate Similarity	NPC472672
0.8217	Intermediate Similarity	NPC123088
0.8214	Intermediate Similarity	NPC476925
0.8214	Intermediate Similarity	NPC21460
0.8212	Intermediate Similarity	NPC159927
0.8212	Intermediate Similarity	NPC476122
0.8212	Intermediate Similarity	NPC469335
0.8212	Intermediate Similarity	NPC477404
0.8212	Intermediate Similarity	NPC46551
0.8212	Intermediate Similarity	NPC196864
0.8205	Intermediate Similarity	NPC329938
0.8205	Intermediate Similarity	NPC207978
0.8205	Intermediate Similarity	NPC69028
0.8205	Intermediate Similarity	NPC472771
0.8205	Intermediate Similarity	NPC193798
0.8205	Intermediate Similarity	NPC82851
0.8205	Intermediate Similarity	NPC263432
0.8205	Intermediate Similarity	NPC5079
0.8201	Intermediate Similarity	NPC477123
0.8201	Intermediate Similarity	NPC329707
0.8201	Intermediate Similarity	NPC476917
0.8201	Intermediate Similarity	NPC327527
0.8201	Intermediate Similarity	NPC477966
0.82	Intermediate Similarity	NPC93666
0.8194	Intermediate Similarity	NPC477403
0.8194	Intermediate Similarity	NPC262872
0.8194	Intermediate Similarity	NPC307383
0.8188	Intermediate Similarity	NPC470999
0.8188	Intermediate Similarity	NPC74612
0.8188	Intermediate Similarity	NPC97904
0.8187	Intermediate Similarity	NPC285227
0.8182	Intermediate Similarity	NPC469485
0.8182	Intermediate Similarity	NPC204663
0.8176	Intermediate Similarity	NPC472765
0.8176	Intermediate Similarity	NPC137295
0.8176	Intermediate Similarity	NPC472766
0.817	Intermediate Similarity	NPC114880
0.817	Intermediate Similarity	NPC302054
0.817	Intermediate Similarity	NPC237259
0.817	Intermediate Similarity	NPC253201
0.817	Intermediate Similarity	NPC34421
0.817	Intermediate Similarity	NPC98206
0.8156	Intermediate Similarity	NPC298190
0.8153	Intermediate Similarity	NPC51568
0.8153	Intermediate Similarity	NPC134254
0.8153	Intermediate Similarity	NPC198047
0.8153	Intermediate Similarity	NPC302369
0.8153	Intermediate Similarity	NPC39986
0.8153	Intermediate Similarity	NPC234660
0.8153	Intermediate Similarity	NPC472773
0.8153	Intermediate Similarity	NPC477405
0.8151	Intermediate Similarity	NPC90296
0.8146	Intermediate Similarity	NPC211625
0.8141	Intermediate Similarity	NPC472653
0.8141	Intermediate Similarity	NPC25255
0.8129	Intermediate Similarity	NPC475066
0.8129	Intermediate Similarity	NPC470119
0.8129	Intermediate Similarity	NPC470118
0.8129	Intermediate Similarity	NPC195131
0.8129	Intermediate Similarity	NPC36655
0.8129	Intermediate Similarity	NPC173544
0.8129	Intermediate Similarity	NPC214495
0.8125	Intermediate Similarity	NPC470995

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 NPC205765 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	850
0.2-0.3	1866
0.3-0.4	2731
0.4-0.5	2135
0.5-0.6	1043
0.6-0.7	229
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.911	High Similarity	NPD5760	Phase 2
0.911	High Similarity	NPD5761	Phase 2
0.7485	Intermediate Similarity	NPD8434	Phase 2
0.7483	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6273	Approved
0.7396	Intermediate Similarity	NPD6764	Approved
0.7396	Intermediate Similarity	NPD6765	Approved
0.7368	Intermediate Similarity	NPD2344	Approved
0.7338	Intermediate Similarity	NPD4628	Phase 3
0.7256	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6784	Approved
0.7225	Intermediate Similarity	NPD6785	Approved
0.7179	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7044	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2799	Discontinued
0.7007	Intermediate Similarity	NPD1876	Approved
0.6986	Remote Similarity	NPD3972	Approved
0.6975	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2796	Approved
0.6957	Remote Similarity	NPD920	Approved
0.6943	Remote Similarity	NPD2800	Approved
0.6937	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6832	Phase 2
0.6923	Remote Similarity	NPD6005	Phase 3
0.6923	Remote Similarity	NPD6002	Phase 3
0.6923	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6004	Phase 3
0.6918	Remote Similarity	NPD7236	Approved
0.6909	Remote Similarity	NPD7819	Suspended
0.6897	Remote Similarity	NPD6559	Discontinued
0.6879	Remote Similarity	NPD1549	Phase 2
0.6864	Remote Similarity	NPD8127	Discontinued
0.6863	Remote Similarity	NPD4140	Approved
0.6859	Remote Similarity	NPD1551	Phase 2
0.6859	Remote Similarity	NPD6100	Approved
0.6859	Remote Similarity	NPD2935	Discontinued
0.6859	Remote Similarity	NPD6099	Approved
0.6846	Remote Similarity	NPD2797	Approved
0.6842	Remote Similarity	NPD2313	Discontinued
0.6832	Remote Similarity	NPD2534	Approved
0.6832	Remote Similarity	NPD2532	Approved
0.6832	Remote Similarity	NPD2533	Approved
0.6829	Remote Similarity	NPD6599	Discontinued
0.6829	Remote Similarity	NPD4380	Phase 2
0.6818	Remote Similarity	NPD5735	Approved
0.6815	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5494	Approved
0.6803	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2798	Approved
0.68	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5647	Approved
0.6797	Remote Similarity	NPD8032	Phase 2
0.6795	Remote Similarity	NPD7033	Discontinued
0.6792	Remote Similarity	NPD7003	Approved
0.6786	Remote Similarity	NPD3749	Approved
0.6786	Remote Similarity	NPD7075	Discontinued
0.6781	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6353	Approved
0.6774	Remote Similarity	NPD1607	Approved
0.6768	Remote Similarity	NPD7458	Discontinued
0.6768	Remote Similarity	NPD3226	Approved
0.6757	Remote Similarity	NPD9717	Approved
0.6753	Remote Similarity	NPD1240	Approved
0.6733	Remote Similarity	NPD1203	Approved
0.6732	Remote Similarity	NPD3268	Approved
0.673	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3882	Suspended
0.6711	Remote Similarity	NPD5327	Phase 3
0.671	Remote Similarity	NPD6355	Discontinued
0.6707	Remote Similarity	NPD7239	Suspended
0.6688	Remote Similarity	NPD1510	Phase 2
0.6688	Remote Similarity	NPD6663	Approved
0.6688	Remote Similarity	NPD4308	Phase 3
0.6687	Remote Similarity	NPD7411	Suspended
0.6687	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2296	Approved
0.6667	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD6653	Approved
0.6647	Remote Similarity	NPD6279	Approved
0.6647	Remote Similarity	NPD6801	Discontinued
0.6647	Remote Similarity	NPD1934	Approved
0.6647	Remote Similarity	NPD6280	Approved
0.6644	Remote Similarity	NPD1608	Approved
0.6629	Remote Similarity	NPD5844	Phase 1
0.6627	Remote Similarity	NPD7768	Phase 2
0.6626	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1243	Approved
0.6623	Remote Similarity	NPD6362	Approved
0.6622	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5763	Approved
0.6604	Remote Similarity	NPD5762	Approved
0.6603	Remote Similarity	NPD447	Suspended
0.6603	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4110	Phase 3
0.6571	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.657	Remote Similarity	NPD1247	Approved
0.6564	Remote Similarity	NPD6799	Approved
0.6562	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6844	Discontinued
0.6536	Remote Similarity	NPD5736	Approved
0.6536	Remote Similarity	NPD9494	Approved
0.6536	Remote Similarity	NPD8312	Approved
0.6536	Remote Similarity	NPD8313	Approved
0.6534	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6808	Phase 2
0.6528	Remote Similarity	NPD1241	Discontinued
0.6527	Remote Similarity	NPD7028	Phase 2
0.6516	Remote Similarity	NPD411	Approved
0.6516	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7473	Discontinued
0.6509	Remote Similarity	NPD2801	Approved
0.6497	Remote Similarity	NPD8404	Phase 2
0.6486	Remote Similarity	NPD5585	Approved
0.6481	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3750	Approved
0.648	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7799	Discontinued
0.6474	Remote Similarity	NPD7199	Phase 2
0.6471	Remote Similarity	NPD5402	Approved
0.6471	Remote Similarity	NPD1019	Discontinued
0.6464	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.646	Remote Similarity	NPD2424	Discontinued
0.6457	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6166	Phase 2
0.6456	Remote Similarity	NPD6651	Approved
0.6453	Remote Similarity	NPD919	Approved
0.645	Remote Similarity	NPD7577	Discontinued
0.6447	Remote Similarity	NPD1283	Approved
0.6446	Remote Similarity	NPD5403	Approved
0.6443	Remote Similarity	NPD3019	Approved
0.6443	Remote Similarity	NPD2932	Approved
0.6443	Remote Similarity	NPD17	Approved
0.6437	Remote Similarity	NPD7315	Approved
0.6437	Remote Similarity	NPD6232	Discontinued
0.6434	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4966	Approved
0.6433	Remote Similarity	NPD4307	Phase 2
0.6433	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4967	Phase 2
0.6433	Remote Similarity	NPD4965	Approved
0.6425	Remote Similarity	NPD7685	Pre-registration
0.6424	Remote Similarity	NPD4662	Approved
0.6424	Remote Similarity	NPD4661	Approved
0.641	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.641	Remote Similarity	NPD3764	Approved
0.6405	Remote Similarity	NPD3266	Approved
0.6405	Remote Similarity	NPD3267	Approved
0.6404	Remote Similarity	NPD7074	Phase 3
0.64	Remote Similarity	NPD3926	Phase 2
0.6395	Remote Similarity	NPD9493	Approved
0.6378	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD2649	Approved
0.6369	Remote Similarity	NPD2651	Approved
0.6364	Remote Similarity	NPD1511	Approved
0.6364	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4624	Approved
0.6353	Remote Similarity	NPD37	Approved
0.6348	Remote Similarity	NPD7286	Phase 2
0.6348	Remote Similarity	NPD7054	Approved
0.6346	Remote Similarity	NPD7008	Discontinued
0.6343	Remote Similarity	NPD7229	Phase 3
0.6343	Remote Similarity	NPD5710	Approved
0.6343	Remote Similarity	NPD5711	Approved
0.6337	Remote Similarity	NPD7057	Phase 3
0.6337	Remote Similarity	NPD7058	Phase 2
0.6335	Remote Similarity	NPD4477	Approved
0.6335	Remote Similarity	NPD4476	Approved
0.6335	Remote Similarity	NPD5712	Approved
0.6333	Remote Similarity	NPD1778	Approved
0.6329	Remote Similarity	NPD3620	Phase 2
0.6329	Remote Similarity	NPD2979	Phase 3
0.6329	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD3142	Approved
0.6329	Remote Similarity	NPD3140	Approved
0.6327	Remote Similarity	NPD7157	Approved
0.6325	Remote Similarity	NPD5401	Approved
0.6323	Remote Similarity	NPD2861	Phase 2
0.6313	Remote Similarity	NPD7472	Approved
0.6309	Remote Similarity	NPD7741	Discontinued
0.6309	Remote Similarity	NPD9545	Approved
0.6307	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7440	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