NPASS Compound

Structure

CID127824 OpenBabel06191715482D 23 24 0 0 1 0 0 0 0 0999 V2000 -4.3317 2.4990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5972 -3.5009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9289 -1.6815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9736 -1.9760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8670 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5817 0.6866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7332 1.9996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5990 2.4994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4652 0.9995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4644 -2.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7322 -2.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3307 0.4992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4647 -1.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7324 -1.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7330 0.9999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4655 1.9991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5977 -2.5008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3305 -0.5015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8665 -0.5006 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -1.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8667 0.5001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8762 -0.2687 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 16 1 0 0 0 0 2 17 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 18 2 0 0 0 0 14 19 1 0 0 0 0 15 21 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 6 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 21 5 1 1 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.26
Volume:	364.33
LogP:	4.545
LogD:	3.891
LogS:	-4.389
# Rotatable Bonds:	2
TPSA:	21.76
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	4.565
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.697
MDCK Permeability:	2.965733983728569e-05
Pgp-inhibitor:	0.737
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	97.00257873535156%
Volume Distribution (VD):	2.413
Pgp-substrate:	2.8163912296295166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.389
CYP2C19-inhibitor:	0.183
CYP2C19-substrate:	0.958
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.544
CYP2D6-inhibitor:	0.152
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.513
CYP3A4-substrate:	0.385

ADMET: Excretion

Clearance (CL):	4.924
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.797
Carcinogencity:	0.142
Eye Corrosion:	0.006
Eye Irritation:	0.052
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC127824

Natural Product ID:	NPC127824
*Common Name:**	(1E,3E,7R,8R,11E)-1-(2-Methoxypropan-2-Yl)-4,8,12-Trimethyloxabicyclo[12.1.0]-Pentadeca-1,3,11-Triene
IUPAC Name:	(1R,4E,6E,10E,14S)-7-(2-methoxypropan-2-yl)-4,10,14-trimethyl-15-oxabicyclo[12.1.0]pentadeca-4,6,10-triene
Synonyms:
Standard InCHIKey:	IVESFYBFQSGMDH-YMYVTDHFSA-N
Standard InCHI:	InChI=1S/C21H34O2/c1-16-8-7-15-21(5)19(23-21)14-11-17(2)10-13-18(12-9-16)20(3,4)22-6/h8,10,13,19H,7,9,11-12,14-15H2,1-6H3/b16-8+,17-10+,18-13+/t19-,21+/m1/s1
SMILES:	COC(/C/1=C/C=C(C)/CC[C@H]2O[C@]2(CC/C=C(/CC1)C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1761952
PubChem CID:	54584323
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000008] Cembrane diterpenoids

*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
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29	Laburnum alpinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5562	Armillaria novae-zelandiae	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6518	Aspilia laevissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2783	Lobophytum sarcophytoides	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4638	Cynoglossum gansuense	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1860	Ceratium reticulatum	Species	Ceratiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO943	Carex nigra	Species	Cyperaceae	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
EC50	1
IC50	1

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3973	Individual Protein	Endothelial PAS domain-containing protein 1	Homo sapiens	EC50	=	148900.0	nM	PMID[549137]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	134200.0	nM	PMID[549137]

☑ 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 NPC127824 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	2100
0.2-0.3	11465
0.3-0.4	17818
0.4-0.5	7837
0.5-0.6	2820
0.6-0.7	425
0.7-0.8	39
0.8-0.85	7
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9138	High Similarity	NPC83838
0.9138	High Similarity	NPC143810
0.8448	Intermediate Similarity	NPC223604
0.8182	Intermediate Similarity	NPC239373
0.8182	Intermediate Similarity	NPC269841
0.8182	Intermediate Similarity	NPC329989
0.8095	Intermediate Similarity	NPC217940
0.803	Intermediate Similarity	NPC276290
0.8	Intermediate Similarity	NPC301525
0.7941	Intermediate Similarity	NPC477084
0.7879	Intermediate Similarity	NPC259299
0.7797	Intermediate Similarity	NPC165755
0.7794	Intermediate Similarity	NPC129630
0.7778	Intermediate Similarity	NPC474005
0.7761	Intermediate Similarity	NPC305698
0.7714	Intermediate Similarity	NPC471525
0.7671	Intermediate Similarity	NPC471537
0.7647	Intermediate Similarity	NPC329656
0.7612	Intermediate Similarity	NPC472266
0.7576	Intermediate Similarity	NPC308844
0.7536	Intermediate Similarity	NPC64234
0.7536	Intermediate Similarity	NPC475310
0.7536	Intermediate Similarity	NPC37929
0.75	Intermediate Similarity	NPC271070
0.7467	Intermediate Similarity	NPC474894
0.7424	Intermediate Similarity	NPC287744
0.7424	Intermediate Similarity	NPC140233
0.7419	Intermediate Similarity	NPC96663
0.7397	Intermediate Similarity	NPC84360
0.7391	Intermediate Similarity	NPC74722
0.7391	Intermediate Similarity	NPC101622
0.7391	Intermediate Similarity	NPC232812
0.7391	Intermediate Similarity	NPC304690
0.7344	Intermediate Similarity	NPC122239
0.7344	Intermediate Similarity	NPC475931
0.7324	Intermediate Similarity	NPC329763
0.7297	Intermediate Similarity	NPC477089
0.7286	Intermediate Similarity	NPC4299
0.7286	Intermediate Similarity	NPC469660
0.7273	Intermediate Similarity	NPC170377
0.7273	Intermediate Similarity	NPC475989
0.7246	Intermediate Similarity	NPC272961
0.7231	Intermediate Similarity	NPC469694
0.7206	Intermediate Similarity	NPC327815
0.7188	Intermediate Similarity	NPC23418
0.7183	Intermediate Similarity	NPC472254
0.7164	Intermediate Similarity	NPC34883
0.7164	Intermediate Similarity	NPC226066
0.7143	Intermediate Similarity	NPC472947
0.7121	Intermediate Similarity	NPC294304
0.7121	Intermediate Similarity	NPC228574
0.7105	Intermediate Similarity	NPC474739
0.7067	Intermediate Similarity	NPC474341
0.7042	Intermediate Similarity	NPC473361
0.7042	Intermediate Similarity	NPC329904
0.7027	Intermediate Similarity	NPC236228
0.7027	Intermediate Similarity	NPC256720
0.7015	Intermediate Similarity	NPC283247
0.7013	Intermediate Similarity	NPC475481
0.7013	Intermediate Similarity	NPC79277
0.7	Intermediate Similarity	NPC61527
0.6986	Remote Similarity	NPC474758
0.6984	Remote Similarity	NPC281590
0.6984	Remote Similarity	NPC329686
0.6974	Remote Similarity	NPC325869
0.697	Remote Similarity	NPC154908
0.697	Remote Similarity	NPC226872
0.697	Remote Similarity	NPC19241
0.697	Remote Similarity	NPC252851
0.697	Remote Similarity	NPC158368
0.6957	Remote Similarity	NPC191233
0.6933	Remote Similarity	NPC476703
0.6933	Remote Similarity	NPC471454
0.6933	Remote Similarity	NPC476439
0.6923	Remote Similarity	NPC181872
0.6923	Remote Similarity	NPC226848
0.6912	Remote Similarity	NPC477457
0.6912	Remote Similarity	NPC477456
0.6901	Remote Similarity	NPC477449
0.6901	Remote Similarity	NPC261398
0.6901	Remote Similarity	NPC477448
0.6892	Remote Similarity	NPC228978
0.6885	Remote Similarity	NPC474495
0.6885	Remote Similarity	NPC473672
0.6883	Remote Similarity	NPC474510
0.6883	Remote Similarity	NPC190008
0.6866	Remote Similarity	NPC475251
0.6857	Remote Similarity	NPC474477
0.6849	Remote Similarity	NPC222244
0.6849	Remote Similarity	NPC476709
0.6849	Remote Similarity	NPC16349
0.6849	Remote Similarity	NPC477085
0.6842	Remote Similarity	NPC4436
0.6835	Remote Similarity	NPC475842
0.6812	Remote Similarity	NPC220766
0.68	Remote Similarity	NPC469880
0.68	Remote Similarity	NPC268111
0.6795	Remote Similarity	NPC246621
0.6795	Remote Similarity	NPC141810
0.679	Remote Similarity	NPC122502
0.6774	Remote Similarity	NPC294358
0.6774	Remote Similarity	NPC40417
0.6769	Remote Similarity	NPC52012
0.6765	Remote Similarity	NPC155849
0.6761	Remote Similarity	NPC224532
0.6761	Remote Similarity	NPC476945
0.6761	Remote Similarity	NPC310210
0.6757	Remote Similarity	NPC190859
0.6757	Remote Similarity	NPC144995
0.6757	Remote Similarity	NPC474551
0.6757	Remote Similarity	NPC470686
0.6757	Remote Similarity	NPC227814
0.6757	Remote Similarity	NPC477204
0.6753	Remote Similarity	NPC233295
0.6753	Remote Similarity	NPC476701
0.6753	Remote Similarity	NPC271632
0.6753	Remote Similarity	NPC617
0.675	Remote Similarity	NPC78673
0.675	Remote Similarity	NPC186155
0.675	Remote Similarity	NPC160517
0.6721	Remote Similarity	NPC26960
0.6721	Remote Similarity	NPC329773
0.6721	Remote Similarity	NPC182102
0.6719	Remote Similarity	NPC227135
0.6716	Remote Similarity	NPC240506
0.6716	Remote Similarity	NPC299730
0.6712	Remote Similarity	NPC477087
0.6712	Remote Similarity	NPC477086
0.6711	Remote Similarity	NPC470751
0.6711	Remote Similarity	NPC315394
0.6711	Remote Similarity	NPC470750
0.6709	Remote Similarity	NPC475936
0.6667	Remote Similarity	NPC265574
0.6667	Remote Similarity	NPC99395
0.6667	Remote Similarity	NPC474496
0.6667	Remote Similarity	NPC107130
0.6667	Remote Similarity	NPC155025
0.6667	Remote Similarity	NPC470693
0.6667	Remote Similarity	NPC329698
0.6667	Remote Similarity	NPC16964
0.6667	Remote Similarity	NPC300593
0.6667	Remote Similarity	NPC197903
0.6667	Remote Similarity	NPC329852
0.6667	Remote Similarity	NPC233332
0.6667	Remote Similarity	NPC474592
0.6625	Remote Similarity	NPC231601
0.6625	Remote Similarity	NPC53867
0.6622	Remote Similarity	NPC92909
0.6622	Remote Similarity	NPC107783
0.6622	Remote Similarity	NPC130665
0.6622	Remote Similarity	NPC238425
0.6622	Remote Similarity	NPC472018
0.6622	Remote Similarity	NPC474543
0.662	Remote Similarity	NPC278895
0.662	Remote Similarity	NPC21998
0.662	Remote Similarity	NPC73603
0.6618	Remote Similarity	NPC207007
0.6618	Remote Similarity	NPC64971
0.6618	Remote Similarity	NPC321867
0.6618	Remote Similarity	NPC225342
0.6618	Remote Similarity	NPC68679
0.6615	Remote Similarity	NPC210316
0.6585	Remote Similarity	NPC261253
0.6585	Remote Similarity	NPC137253
0.6585	Remote Similarity	NPC474045
0.6585	Remote Similarity	NPC281316
0.6582	Remote Similarity	NPC315731
0.6582	Remote Similarity	NPC471661
0.6582	Remote Similarity	NPC184208
0.6582	Remote Similarity	NPC112868
0.6582	Remote Similarity	NPC8538
0.6579	Remote Similarity	NPC170148
0.6579	Remote Similarity	NPC476317
0.6579	Remote Similarity	NPC477202
0.6575	Remote Similarity	NPC69462
0.6575	Remote Similarity	NPC315285
0.6575	Remote Similarity	NPC316029
0.6571	Remote Similarity	NPC19569
0.6571	Remote Similarity	NPC182794
0.6567	Remote Similarity	NPC474267
0.6567	Remote Similarity	NPC278202
0.6548	Remote Similarity	NPC106040
0.6548	Remote Similarity	NPC115179
0.6538	Remote Similarity	NPC477088
0.6538	Remote Similarity	NPC242767
0.6533	Remote Similarity	NPC140287
0.6533	Remote Similarity	NPC15499
0.6533	Remote Similarity	NPC259599
0.6533	Remote Similarity	NPC167049
0.6533	Remote Similarity	NPC117746
0.6533	Remote Similarity	NPC469691
0.6533	Remote Similarity	NPC294434
0.6528	Remote Similarity	NPC474823
0.6522	Remote Similarity	NPC179087
0.6522	Remote Similarity	NPC473508
0.6522	Remote Similarity	NPC210303
0.6522	Remote Similarity	NPC44343
0.6515	Remote Similarity	NPC7491
0.6515	Remote Similarity	NPC27853
0.6515	Remote Similarity	NPC101285

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 NPC127824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	2414
0.2-0.3	4240
0.3-0.4	1886
0.4-0.5	336
0.5-0.6	75
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8413	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD8039	Approved
0.6618	Remote Similarity	NPD368	Approved
0.65	Remote Similarity	NPD5209	Approved
0.6471	Remote Similarity	NPD7838	Discovery
0.6447	Remote Similarity	NPD8264	Approved
0.641	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4219	Approved
0.6349	Remote Similarity	NPD6927	Phase 3
0.6316	Remote Similarity	NPD6926	Approved
0.6316	Remote Similarity	NPD6924	Approved
0.625	Remote Similarity	NPD7514	Phase 3
0.625	Remote Similarity	NPD7332	Phase 2
0.622	Remote Similarity	NPD6695	Phase 3
0.6216	Remote Similarity	NPD6922	Approved
0.6216	Remote Similarity	NPD6923	Approved
0.6184	Remote Similarity	NPD4732	Discontinued
0.6173	Remote Similarity	NPD6902	Approved
0.6154	Remote Similarity	NPD6933	Approved
0.6145	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7144	Approved
0.6133	Remote Similarity	NPD7143	Approved
0.6092	Remote Similarity	NPD6698	Approved
0.6092	Remote Similarity	NPD46	Approved
0.6087	Remote Similarity	NPD6648	Approved
0.6076	Remote Similarity	NPD6925	Approved
0.6076	Remote Similarity	NPD5776	Phase 2
0.6076	Remote Similarity	NPD6932	Approved
0.6071	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD4265	Approved
0.6053	Remote Similarity	NPD7150	Approved
0.6053	Remote Similarity	NPD7151	Approved
0.6053	Remote Similarity	NPD7152	Approved
0.6049	Remote Similarity	NPD6930	Phase 2
0.6049	Remote Similarity	NPD6931	Approved
0.6032	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD6051	Approved
0.5976	Remote Similarity	NPD6898	Phase 1
0.597	Remote Similarity	NPD342	Phase 1
0.5952	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.593	Remote Similarity	NPD7524	Approved
0.593	Remote Similarity	NPD7750	Discontinued
0.5926	Remote Similarity	NPD6683	Phase 2
0.5926	Remote Similarity	NPD6929	Approved
0.5854	Remote Similarity	NPD7509	Discontinued
0.5833	Remote Similarity	NPD7154	Phase 3
0.5811	Remote Similarity	NPD7331	Phase 2
0.5806	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD1695	Approved
0.5775	Remote Similarity	NPD1145	Discontinued
0.5714	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD6893	Approved
0.5694	Remote Similarity	NPD4194	Approved
0.5694	Remote Similarity	NPD4191	Approved
0.5694	Remote Similarity	NPD4193	Approved
0.5694	Remote Similarity	NPD4192	Approved
0.5692	Remote Similarity	NPD2268	Discontinued
0.5684	Remote Similarity	NPD5344	Discontinued
0.5667	Remote Similarity	NPD7087	Discontinued
0.5667	Remote Similarity	NPD7637	Suspended
0.5667	Remote Similarity	NPD7983	Approved
0.5663	Remote Similarity	NPD4820	Approved
0.5663	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD4822	Approved
0.5663	Remote Similarity	NPD4821	Approved
0.5663	Remote Similarity	NPD4819	Approved
0.5647	Remote Similarity	NPD5362	Discontinued
0.561	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD5779	Approved
0.5604	Remote Similarity	NPD5778	Approved
0.56	Remote Similarity	NPD616	Clinical (unspecified phase)

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