NPASS Compound

Structure

CID233763 OpenBabel06191716032D 24 27 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 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 1.7321 2.0000 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 5.2812 1.8090 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 1.0000 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 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 23 1 0 0 0 0 4 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 6 16 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 5 1 1 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 19 1 6 0 0 0 15 24 1 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 1 1 6 0 0 0 20 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	344.865
LogP:	3.623
LogD:	3.63
LogS:	-5.076
# Rotatable Bonds:	2
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	4.288
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.827
MDCK Permeability:	3.157410174026154e-05
Pgp-inhibitor:	0.949
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.661

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	93.63720703125%
Volume Distribution (VD):	1.697
Pgp-substrate:	4.1133856773376465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.718
CYP1A2-substrate:	0.736
CYP2C19-inhibitor:	0.703
CYP2C19-substrate:	0.792
CYP2C9-inhibitor:	0.681
CYP2C9-substrate:	0.637
CYP2D6-inhibitor:	0.402
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.919
CYP3A4-substrate:	0.5

ADMET: Excretion

Clearance (CL):	6.132
Half-life (T1/2):	0.224

ADMET: Toxicity

hERG Blockers:	0.128
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.347
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.684
Maximum Recommended Daily Dose:	0.668
Skin Sensitization:	0.292
Carcinogencity:	0.184
Eye Corrosion:	0.006
Eye Irritation:	0.064
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC233763

Natural Product ID:	NPC233763
*Common Name:**	Nortaepeenin A
IUPAC Name:	methyl (4R,4aR,6aR,11aS,11bR)-4,11b-dimethyl-7-oxo-2,3,4a,5,6,6a,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-4-carboxylate
Synonyms:
Standard InCHIKey:	YSMSCOUXKWVCGA-HRPNNTJESA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-19-8-4-9-20(2,18(22)23-3)16(19)6-5-12-14(19)11-15-13(17(12)21)7-10-24-15/h7,10,12,14,16H,4-6,8-9,11H2,1-3H3/t12-,14+,16-,19-,20-/m1/s1
SMILES:	C[C@@]12CCC[C@](C)([C@@H]2CC[C@@H]2[C@@H]1Cc1c(cco1)C2=O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358072
PubChem CID:	11587964
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO32931	pterolobium macropterum	Species	Fabaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[25337628]
NPO529	Thalictrum glaucum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18156	Andrographis lineata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO529	Thalictrum glaucum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3816	Aspergillus sulphureus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22703	Lithoplocamia lithistoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19115	Hoya australis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO529	Thalictrum glaucum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18970	Baccharis patagonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7358	Xanthoparmelia verrucigera	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18156	Andrographis lineata	Species	Acanthaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	147690.0	nM	PMID[490514]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34830.0	nM	PMID[490514]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23240.0	nM	PMID[490514]

☑ 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 NPC233763 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	397
0.1-0.2	1556
0.2-0.3	3162
0.3-0.4	7446
0.4-0.5	11777
0.5-0.6	7178
0.6-0.7	8522
0.7-0.8	2419
0.8-0.85	174
0.85-0.9	58
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9371	High Similarity	NPC224418
0.9324	High Similarity	NPC81405
0.9262	High Similarity	NPC140952
0.9247	High Similarity	NPC144010
0.9071	High Similarity	NPC307401
0.9071	High Similarity	NPC42400
0.902	High Similarity	NPC56358
0.8973	High Similarity	NPC281398
0.8947	High Similarity	NPC287559
0.8944	High Similarity	NPC202260
0.8933	High Similarity	NPC25351
0.8903	High Similarity	NPC270312
0.8896	High Similarity	NPC472664
0.8873	High Similarity	NPC177262
0.8851	High Similarity	NPC192069
0.8844	High Similarity	NPC71821
0.8808	High Similarity	NPC88958
0.8808	High Similarity	NPC179170
0.88	High Similarity	NPC145830
0.8792	High Similarity	NPC472298
0.8776	High Similarity	NPC62799
0.8767	High Similarity	NPC199044
0.8767	High Similarity	NPC238843
0.8766	High Similarity	NPC18986
0.875	High Similarity	NPC104736
0.875	High Similarity	NPC41880
0.8718	High Similarity	NPC121995
0.8707	High Similarity	NPC93241
0.8707	High Similarity	NPC27798
0.8693	High Similarity	NPC304692
0.8667	High Similarity	NPC228842
0.8667	High Similarity	NPC212257
0.8652	High Similarity	NPC470740
0.8649	High Similarity	NPC262198
0.8649	High Similarity	NPC471292
0.8639	High Similarity	NPC142113
0.8639	High Similarity	NPC117674
0.8636	High Similarity	NPC474611
0.863	High Similarity	NPC263337
0.8611	High Similarity	NPC236532
0.8611	High Similarity	NPC476943
0.8601	High Similarity	NPC146872
0.86	High Similarity	NPC95526
0.8581	High Similarity	NPC290038
0.8571	High Similarity	NPC221992
0.8553	High Similarity	NPC294511
0.8553	High Similarity	NPC121615
0.8552	High Similarity	NPC474722
0.8552	High Similarity	NPC265181
0.8543	High Similarity	NPC196864
0.8543	High Similarity	NPC159927
0.8543	High Similarity	NPC477404
0.8543	High Similarity	NPC469335
0.8533	High Similarity	NPC19747
0.8526	High Similarity	NPC68848
0.8526	High Similarity	NPC188649
0.8521	High Similarity	NPC293253
0.85	High Similarity	NPC59502
0.8497	Intermediate Similarity	NPC10429
0.8493	Intermediate Similarity	NPC18904
0.8493	Intermediate Similarity	NPC148374
0.8493	Intermediate Similarity	NPC56197
0.8477	Intermediate Similarity	NPC211625
0.8471	Intermediate Similarity	NPC285567
0.8471	Intermediate Similarity	NPC283209
0.8471	Intermediate Similarity	NPC288602
0.8471	Intermediate Similarity	NPC88841
0.8456	Intermediate Similarity	NPC245522
0.8456	Intermediate Similarity	NPC56731
0.8456	Intermediate Similarity	NPC114513
0.8446	Intermediate Similarity	NPC267632
0.8442	Intermediate Similarity	NPC75310
0.8428	Intermediate Similarity	NPC473753
0.8428	Intermediate Similarity	NPC473766
0.8418	Intermediate Similarity	NPC276735
0.8414	Intermediate Similarity	NPC310830
0.8405	Intermediate Similarity	NPC472665
0.8397	Intermediate Similarity	NPC299094
0.8397	Intermediate Similarity	NPC10051
0.8397	Intermediate Similarity	NPC473368
0.8389	Intermediate Similarity	NPC476944
0.8389	Intermediate Similarity	NPC84479
0.8378	Intermediate Similarity	NPC52412
0.8377	Intermediate Similarity	NPC44606
0.8377	Intermediate Similarity	NPC178932
0.8366	Intermediate Similarity	NPC272590
0.8365	Intermediate Similarity	NPC475779
0.8356	Intermediate Similarity	NPC220094
0.8345	Intermediate Similarity	NPC179354
0.8344	Intermediate Similarity	NPC167340
0.8344	Intermediate Similarity	NPC333139
0.8344	Intermediate Similarity	NPC472299
0.8333	Intermediate Similarity	NPC194499
0.8333	Intermediate Similarity	NPC88007
0.8333	Intermediate Similarity	NPC7059
0.8333	Intermediate Similarity	NPC185456
0.8333	Intermediate Similarity	NPC195954
0.8323	Intermediate Similarity	NPC469850
0.8323	Intermediate Similarity	NPC472786
0.8323	Intermediate Similarity	NPC469336
0.8322	Intermediate Similarity	NPC205071
0.8312	Intermediate Similarity	NPC246164
0.8312	Intermediate Similarity	NPC475777
0.8301	Intermediate Similarity	NPC46551
0.8291	Intermediate Similarity	NPC471003
0.8289	Intermediate Similarity	NPC93666
0.8286	Intermediate Similarity	NPC74612
0.8278	Intermediate Similarity	NPC478166
0.8273	Intermediate Similarity	NPC178382
0.8261	Intermediate Similarity	NPC296558
0.8258	Intermediate Similarity	NPC24232
0.8258	Intermediate Similarity	NPC114880
0.8239	Intermediate Similarity	NPC198904
0.8228	Intermediate Similarity	NPC8389
0.8224	Intermediate Similarity	NPC10088
0.8224	Intermediate Similarity	NPC216755
0.8224	Intermediate Similarity	NPC221809
0.8219	Intermediate Similarity	NPC46896
0.8217	Intermediate Similarity	NPC472283
0.8217	Intermediate Similarity	NPC167142
0.8217	Intermediate Similarity	NPC472772
0.821	Intermediate Similarity	NPC302392
0.821	Intermediate Similarity	NPC44602
0.821	Intermediate Similarity	NPC473945
0.8205	Intermediate Similarity	NPC23559
0.8201	Intermediate Similarity	NPC16922
0.82	Intermediate Similarity	NPC103134
0.8194	Intermediate Similarity	NPC75906
0.8194	Intermediate Similarity	NPC471817
0.8188	Intermediate Similarity	NPC20500
0.8182	Intermediate Similarity	NPC156189
0.8182	Intermediate Similarity	NPC476122
0.8176	Intermediate Similarity	NPC79571
0.8176	Intermediate Similarity	NPC197596
0.8176	Intermediate Similarity	NPC263432
0.8176	Intermediate Similarity	NPC470939
0.8165	Intermediate Similarity	NPC123153
0.8163	Intermediate Similarity	NPC310043
0.8163	Intermediate Similarity	NPC470742
0.816	Intermediate Similarity	NPC294512
0.8158	Intermediate Similarity	NPC276676
0.8158	Intermediate Similarity	NPC346
0.8153	Intermediate Similarity	NPC60973
0.8153	Intermediate Similarity	NPC107646
0.8153	Intermediate Similarity	NPC263265
0.8146	Intermediate Similarity	NPC251865
0.8141	Intermediate Similarity	NPC471863
0.8141	Intermediate Similarity	NPC30222
0.8133	Intermediate Similarity	NPC121158
0.8133	Intermediate Similarity	NPC473152
0.8125	Intermediate Similarity	NPC476197
0.8125	Intermediate Similarity	NPC476035
0.8125	Intermediate Similarity	NPC663
0.8125	Intermediate Similarity	NPC14499
0.8125	Intermediate Similarity	NPC475039
0.8125	Intermediate Similarity	NPC224394
0.8125	Intermediate Similarity	NPC298190
0.8117	Intermediate Similarity	NPC195325
0.8117	Intermediate Similarity	NPC471001
0.8117	Intermediate Similarity	NPC234494
0.8117	Intermediate Similarity	NPC472654
0.8113	Intermediate Similarity	NPC191828
0.8112	Intermediate Similarity	NPC208389
0.8108	Intermediate Similarity	NPC471542
0.8105	Intermediate Similarity	NPC471174
0.8105	Intermediate Similarity	NPC470941
0.8105	Intermediate Similarity	NPC302987
0.8101	Intermediate Similarity	NPC469847
0.8095	Intermediate Similarity	NPC214572
0.8089	Intermediate Similarity	NPC35000
0.8089	Intermediate Similarity	NPC264943
0.8089	Intermediate Similarity	NPC92979
0.8089	Intermediate Similarity	NPC281258
0.8079	Intermediate Similarity	NPC470273
0.8079	Intermediate Similarity	NPC223415
0.8077	Intermediate Similarity	NPC476201
0.8077	Intermediate Similarity	NPC471613
0.8077	Intermediate Similarity	NPC469503
0.8065	Intermediate Similarity	NPC470997
0.8065	Intermediate Similarity	NPC5180
0.8063	Intermediate Similarity	NPC472771
0.8063	Intermediate Similarity	NPC329938
0.8063	Intermediate Similarity	NPC69028
0.8058	Intermediate Similarity	NPC97566
0.8054	Intermediate Similarity	NPC233707
0.8052	Intermediate Similarity	NPC252208
0.805	Intermediate Similarity	NPC237155
0.805	Intermediate Similarity	NPC84349
0.805	Intermediate Similarity	NPC472823
0.8049	Intermediate Similarity	NPC475641
0.8049	Intermediate Similarity	NPC475237
0.8042	Intermediate Similarity	NPC476917
0.8042	Intermediate Similarity	NPC327527
0.8041	Intermediate Similarity	NPC215109
0.8041	Intermediate Similarity	NPC170604
0.8038	Intermediate Similarity	NPC209364
0.8028	Intermediate Similarity	NPC46536
0.8028	Intermediate Similarity	NPC138139
0.8027	Intermediate Similarity	NPC158525
0.8027	Intermediate Similarity	NPC92941

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 NPC233763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	944
0.2-0.3	1556
0.3-0.4	2694
0.4-0.5	2153
0.5-0.6	1060
0.6-0.7	332
0.7-0.8	65
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
0.8552	High Similarity	NPD1471	Phase 3
0.8344	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD8434	Phase 2
0.7834	Intermediate Similarity	NPD3226	Approved
0.7821	Intermediate Similarity	NPD920	Approved
0.7815	Intermediate Similarity	NPD2344	Approved
0.78	Intermediate Similarity	NPD2799	Discontinued
0.7771	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5760	Phase 2
0.775	Intermediate Similarity	NPD5761	Phase 2
0.7744	Intermediate Similarity	NPD6808	Phase 2
0.7712	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2346	Discontinued
0.7643	Intermediate Similarity	NPD6273	Approved
0.7613	Intermediate Similarity	NPD2309	Approved
0.7588	Intermediate Similarity	NPD6765	Approved
0.7588	Intermediate Similarity	NPD6764	Approved
0.7584	Intermediate Similarity	NPD8032	Phase 2
0.758	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3972	Approved
0.7564	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7819	Suspended
0.7517	Intermediate Similarity	NPD2313	Discontinued
0.7516	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7469	Intermediate Similarity	NPD6280	Approved
0.7469	Intermediate Similarity	NPD6279	Approved
0.7453	Intermediate Similarity	NPD6599	Discontinued
0.7436	Intermediate Similarity	NPD4628	Phase 3
0.7415	Intermediate Similarity	NPD3266	Approved
0.7415	Intermediate Similarity	NPD3267	Approved
0.7414	Intermediate Similarity	NPD6784	Approved
0.7414	Intermediate Similarity	NPD6785	Approved
0.7403	Intermediate Similarity	NPD2796	Approved
0.7394	Intermediate Similarity	NPD3749	Approved
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7379	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1243	Approved
0.7365	Intermediate Similarity	NPD2798	Approved
0.7361	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD919	Approved
0.7347	Intermediate Similarity	NPD1876	Approved
0.7325	Intermediate Similarity	NPD7003	Approved
0.7305	Intermediate Similarity	NPD5494	Approved
0.7285	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1247	Approved
0.7255	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6799	Approved
0.7179	Intermediate Similarity	NPD2935	Discontinued
0.7178	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3926	Phase 2
0.7152	Intermediate Similarity	NPD2800	Approved
0.7152	Intermediate Similarity	NPD6801	Discontinued
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7123	Intermediate Similarity	NPD17	Approved
0.7115	Intermediate Similarity	NPD3748	Approved
0.7093	Intermediate Similarity	NPD7473	Discontinued
0.7091	Intermediate Similarity	NPD5890	Approved
0.7091	Intermediate Similarity	NPD5889	Approved
0.7086	Intermediate Similarity	NPD6559	Discontinued
0.7083	Intermediate Similarity	NPD7075	Discontinued
0.7078	Intermediate Similarity	NPD2979	Phase 3
0.7078	Intermediate Similarity	NPD4307	Phase 2
0.7078	Intermediate Similarity	NPD4140	Approved
0.707	Intermediate Similarity	NPD1551	Phase 2
0.7066	Intermediate Similarity	NPD2296	Approved
0.7055	Intermediate Similarity	NPD5585	Approved
0.7037	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1933	Approved
0.7027	Intermediate Similarity	NPD1281	Approved
0.7024	Intermediate Similarity	NPD7768	Phase 2
0.702	Intermediate Similarity	NPD1019	Discontinued
0.7019	Intermediate Similarity	NPD7236	Approved
0.7018	Intermediate Similarity	NPD6232	Discontinued
0.6993	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1241	Discontinued
0.6981	Remote Similarity	NPD1549	Phase 2
0.6981	Remote Similarity	NPD970	Clinical (unspecified phase)
0.698	Remote Similarity	NPD9717	Approved
0.698	Remote Similarity	NPD1608	Approved
0.6964	Remote Similarity	NPD3817	Phase 2
0.6959	Remote Similarity	NPD8127	Discontinued
0.6959	Remote Similarity	NPD6959	Discontinued
0.6957	Remote Similarity	NPD3887	Approved
0.6954	Remote Similarity	NPD1203	Approved
0.6954	Remote Similarity	NPD2797	Approved
0.6951	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3764	Approved
0.6939	Remote Similarity	NPD5691	Approved
0.6933	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5327	Phase 3
0.6928	Remote Similarity	NPD6585	Discontinued
0.6923	Remote Similarity	NPD3882	Suspended
0.6923	Remote Similarity	NPD6355	Discontinued
0.6918	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1510	Phase 2
0.6899	Remote Similarity	NPD4308	Phase 3
0.6894	Remote Similarity	NPD3750	Approved
0.6894	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD8166	Discontinued
0.6894	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4110	Phase 3
0.6887	Remote Similarity	NPD1283	Approved
0.6855	Remote Similarity	NPD2531	Phase 2
0.6855	Remote Similarity	NPD2438	Suspended
0.6842	Remote Similarity	NPD1470	Approved
0.6839	Remote Similarity	NPD411	Approved
0.6839	Remote Similarity	NPD6798	Discontinued
0.6824	Remote Similarity	NPD1651	Approved
0.6821	Remote Similarity	NPD4359	Approved
0.6818	Remote Similarity	NPD5844	Phase 1
0.6816	Remote Similarity	NPD8312	Approved
0.6816	Remote Similarity	NPD8313	Approved
0.6815	Remote Similarity	NPD447	Suspended
0.6815	Remote Similarity	NPD4622	Approved
0.6815	Remote Similarity	NPD4618	Approved
0.6813	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2353	Approved
0.6807	Remote Similarity	NPD7239	Suspended
0.6806	Remote Similarity	NPD5535	Approved
0.6792	Remote Similarity	NPD7033	Discontinued
0.679	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1778	Approved
0.6774	Remote Similarity	NPD7095	Approved
0.6772	Remote Similarity	NPD1607	Approved
0.6768	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5402	Approved
0.6761	Remote Similarity	NPD3818	Discontinued
0.6761	Remote Similarity	NPD7177	Discontinued
0.6761	Remote Similarity	NPD2182	Approved
0.6752	Remote Similarity	NPD3140	Approved
0.6752	Remote Similarity	NPD1240	Approved
0.6752	Remote Similarity	NPD3142	Approved
0.6751	Remote Similarity	NPD8404	Phase 2
0.675	Remote Similarity	NPD4476	Approved
0.675	Remote Similarity	NPD4477	Approved
0.675	Remote Similarity	NPD6099	Approved
0.675	Remote Similarity	NPD6100	Approved
0.6747	Remote Similarity	NPD5403	Approved
0.6746	Remote Similarity	NPD1934	Approved
0.6742	Remote Similarity	NPD5953	Discontinued
0.6739	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5689	Approved
0.673	Remote Similarity	NPD5688	Approved
0.673	Remote Similarity	NPD7097	Phase 1
0.6727	Remote Similarity	NPD5401	Approved
0.6726	Remote Similarity	NPD4380	Phase 2
0.6725	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7229	Phase 3
0.6711	Remote Similarity	NPD3024	Approved
0.6711	Remote Similarity	NPD3025	Approved
0.6706	Remote Similarity	NPD2801	Approved
0.6702	Remote Similarity	NPD8285	Discontinued
0.6688	Remote Similarity	NPD5647	Approved
0.6688	Remote Similarity	NPD6663	Approved
0.6687	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD6651	Approved
0.6648	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2403	Approved
0.6647	Remote Similarity	NPD6844	Discontinued
0.6646	Remote Similarity	NPD2354	Approved
0.6646	Remote Similarity	NPD4060	Phase 1
0.6645	Remote Similarity	NPD5736	Approved
0.663	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5710	Approved
0.6629	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5711	Approved
0.6629	Remote Similarity	NPD7286	Phase 2
0.6627	Remote Similarity	NPD7028	Phase 2
0.6624	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3496	Discontinued
0.6623	Remote Similarity	NPD3026	Approved
0.6623	Remote Similarity	NPD3023	Approved
0.6623	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3134	Approved
0.6606	Remote Similarity	NPD7440	Discontinued
0.6588	Remote Similarity	NPD6873	Phase 2
0.6582	Remote Similarity	NPD6233	Phase 2
0.6582	Remote Similarity	NPD4870	Approved
0.6579	Remote Similarity	NPD1611	Approved
0.6579	Remote Similarity	NPD1201	Approved
0.6579	Remote Similarity	NPD6287	Discontinued
0.6575	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7199	Phase 2

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